exv10w6






Exhibit 10.6




SECURED SUBORDINATED CONVERTIBLE NOTE AND WARRANT




PURCHASE AGREEMENT




NUPATHE INC.




April 9, 2010









 









 








SCHEDULES AND EXHIBITS

TO

SECURED SUBORDINATED CONVERTIBLE NOTE AND WARRANT

PURCHASE AGREEMENT




	 	 	 	 	 
	Schedules:
	 	3.3	 	 	Capitalization; Voting Rights

	 	3.5	 	 	Financial Statements

	 	3.6	 	 	Liabilities







	 	 	 
	Exhibits:
	Exhibit A
	 	Schedule of Purchasers

	Exhibit B
	 	Form of Secured Subordinated Convertible Promissory Note

	Exhibit C
	 	Form of Warrant

	Exhibit D
	 	Knowledge Persons

	Exhibit E-1 and E-2 
	 	Capitalization












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NUPATHE INC.




SECURED SUBORDINATED CONVERTIBLE NOTE AND WARRANT




PURCHASE AGREEMENT




          THIS SECURED SUBORDINATED CONVERTIBLE NOTE AND WARRANT PURCHASE AGREEMENT (the “Agreement”) is
entered into on April 9, 2010 by and among NuPathe Inc., a Delaware corporation (the “Company”),
and the purchasers identified on Exhibit A on the date hereof (the “Purchasers”).




BACKGROUND



          A. The Company currently is in the business of developing therapeutic products for the
treatment of neurological and psychiatric disorders (such products developed, manufactured or
distributed by the Company, the “Products,” and the development, manufacture or distribution of the
Products being the “Business”).




          B. The Company has authorized the sale and issuance of secured subordinated convertible
promissory notes substantially in the form attached hereto as Exhibit B (each, as executed
by the Company, a “Note” and collectively, the “Notes”) having an aggregate principal amount of up
to $10,062,500.




          C. As an inducement to each Purchaser to purchase a Note (or Notes), the Company has
authorized the issuance of a warrant to each Purchaser to purchase stock in substantially the form
attached hereto as Exhibit C (each, as executed by the Company, a “Warrant” and
collectively, the “Warrants”).




          D. Each Purchaser desires to purchase the Notes and the Warrants on the terms and conditions
set forth herein.




          E. The Company desires to issue and sell the Notes and the Warrants to each Purchaser on the
terms and conditions set forth herein.




          NOW, THEREFORE, in consideration of the representations, warranties, covenants and agreements
herein contained and for other good and valuable consideration, the receipt and sufficiency of
which are hereby acknowledged, the parties hereto, intending to be legally bound, hereby agree as
follows:




     1. AGREEMENT TO SELL AND PURCHASE.



          1.1. Authorization of Notes, Shares and Conversion Shares. The Company has authorized
(i) the sale and issuance to the Purchasers of the Notes, (ii) the reservation of shares (the
"Shares”) of the Company’s Series B Preferred Stock, $0.001 par value per share (“Series B
Preferred Stock”), issuable upon conversion of the Notes and (iii) the reservation of shares of the
Company’s common stock, par value $0.001 per share (the “Common Stock”), issuable upon conversion
of the Shares (the “Conversion Shares”). The Shares and the Conversion Shares shall have the
rights, preferences, privileges and restrictions set forth in the Third Amended and Restated
Certificate of Incorporation of the Company, as amended (the “Certificate”).







 









 








          1.2. Authorization of Warrants and Warrant Shares. The Company has authorized (i) the
issuance to the Purchasers of the Warrants, (ii) the reservation of shares of Series B Preferred
Stock (the “Warrant Shares”), issuable upon exercise of the Warrants and (iii) the reservation of
shares of Common Stock issuable upon exercise of the Warrants, and/or conversion of the Warrant
Shares, as applicable (the “Warrant Conversion Shares”). The Warrant Shares and the Warrant
Conversion Shares will have the rights, preferences, privileges and restrictions set forth in the
Certificate. The Company, on the one hand, and each Purchaser, on the other hand, having adverse
interests and as a result of arm’s length bargaining, agree that: (a) neither the Purchaser nor any
individual or entity affiliated with the Purchaser has rendered any services to the Company in
connection with this Agreement; (b) the Warrants are not being issued as compensation; and (c) all
tax returns and other information of each party relative to this Agreement and the Notes and
Warrants issued pursuant hereto shall consistently reflect the matters agreed to in (a) and (b)
above.




          1.3. Sale and Purchase. Subject to the terms and conditions hereof, and in reliance
upon the representations, warranties and covenants contained herein, (i) at the Initial Closing (as
defined below) the Company shall issue and sell to each Purchaser, severally and not jointly, and
each Purchaser shall purchase from the Company, severally and not jointly, a Note having an
original principal amount equal to the amount set forth opposite such Purchaser’s name on
Exhibit A under Column B (collectively, the “Initial Closing Notes”), and (ii) at the
Second Closing (as defined below) the Company shall issue and sell to certain Purchasers, severally
and not jointly, and such Purchasers shall purchase from the Company, severally and not jointly, a
Note having an original principal amount equal to the amount set forth opposite such Purchaser’s
name on Exhibit A under Column C (collectively, the “Second Closing Notes”).




          1.4. Issuance of Warrants. The Company shall issue to each Purchaser a Warrant
determined as follows:




               (a) Upon conversion of the Note (or Notes) issued to such Purchaser pursuant to Section 4(b)
thereof in connection with an Acquisition Transaction (as defined in the Note), the Company shall
issue a Warrant to subscribe for and purchase up to a number of shares of Series B Preferred Stock
equal to (i) the outstanding principal amount of the Note (or Notes) at the date of such conversion
multiplied by twenty-five percent (25%), divided by (ii) the Acquisition Conversion Price (as
defined in the Note). The per share exercise price under the Warrant shall initially be equal to
the Acquisition Conversion Price.



               (b) Upon conversion of the Note (or Notes) issued to such Purchaser pursuant to Section 4(c)
thereof in connection with a Qualified Financing (as defined in the Note), the Company shall issue
a Warrant to subscribe for and purchase up to a number of shares of Equity Securities (as defined
in the Note) equal to (i) the outstanding principal amount of the Note (or Notes) at the date of
such conversion multiplied by twenty-five percent (25%), divided by (ii) the Qualified Financing
Conversion Price (as defined in the Note). The per share exercise price under the Warrant shall
initially be equal to the Qualified Financing Conversion Price.



               (c) If the Note (or Notes) issued to such Purchaser is not converted pursuant to Section 4 of
the Note, at the Maturity Date (as defined in the Note), the Company shall issue a Warrant to
subscribe for and purchase up to a number of shares of Series B Preferred Stock equal to (i) the
outstanding principal amount of the Note (or Notes) at the date of such conversion multiplied by
twenty-five percent (25%), divided by (ii) the Optional Conversion Price (as defined in the Note).
The per share exercise price under the Warrant shall initially be equal to the Optional Conversion
Price.



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     2. CLOSINGS, DELIVERY AND PAYMENT.



          2.1. Closings. The closing of the sale and purchase of the Initial Closing Notes
under this Agreement (the “Initial Closing”) shall take place at 10:00 a.m. on the date hereof, at
the offices of Morgan Lewis & Bockius LLP, 1701 Market Street, Philadelphia, PA 19103, or at such
other time or place as the Company and the Purchasers may mutually agree (such date is hereinafter
referred to as the “Initial Closing Date”). The closing of the sale and purchase of the Second
Closing Notes under this Agreement (the “Second Closing,” and together with the Initial Closing,
the “Closings”) shall take place at 10:00 a.m. on April 20, 2010, at the offices of Morgan Lewis &
Bockius LLP, 1701 Market Street, Philadelphia, PA 19103, or at such other time or place as the
Company and the Majority Holders (as defined in the Note) may mutually agree (such date is
hereinafter referred to as the “Second Closing Date”); provided, that upon the satisfaction of the
conditions set forth in Section 5.1 at the Initial Closing, there shall be no additional conditions
with respect to the consummation of the Second Closing.




          2.2. Delivery; Payment. At the Initial Closing and the Second Closing, subject to the
terms and conditions hereof, the Company will deliver to each Purchaser a fully executed Initial
Closing Note or Second Closing Note, as applicable, against payment for such securities in cash by
wire transfer of immediately available funds made payable to the order of the Company or as it
shall direct.




          2.3. Use of Proceeds. The proceeds received by the Company from the sale of the Notes
and the Warrants shall be used for general corporate purposes including working capital.




     3. REPRESENTATIONS AND WARRANTIES OF THE COMPANY.



          The Company represents and warrants to each of the Purchasers that the statements made in this
Section 3, together with the disclosure set forth on the disclosure schedules referenced herein and
attached hereto (the “Schedules”), are true and correct on the date hereof. The Schedules shall be
arranged to correspond to the numbered paragraphs contained in this Section 3, and the disclosure
in any paragraph of the Schedules shall qualify other subsections in Section 3 only to the extent
that it is readily apparent from a reading of the disclosure that such disclosure is applicable to
such other subsections. As used herein, the term “Knowledge” means the actual knowledge, following
such inquiries and investigations as would be deemed appropriate by a reasonable businessperson
engaged in a business similar to the Business in the prudent management of his or her business
affairs, of the persons set forth on Exhibit D and the term “Actual Knowledge” means the
actual knowledge of the persons set forth on Exhibit D.




          3.1. Organization, Good Standing and Qualification. The Company is a corporation duly
incorporated, validly existing and in good standing under the laws of the State of Delaware. The
Company has all requisite corporate power and authority to own and operate its properties and
assets, to execute and deliver this Agreement, to issue and sell each of the Notes and to issue
each of the Warrants and, upon conversion of the Notes, to issue the Shares and, upon conversion of
the Shares, to issue the Conversion Shares, and, upon exercise of the Warrants, to issue the
Warrant Shares and, upon conversion of the Warrant Shares, to issue the Warrant Conversion Shares
(the Notes, Shares, Conversion Shares, Warrants, Warrant Shares and Warrant Conversion Shares are
sometimes referred to herein, collectively or separately as the context may require, as the
"Securities”), and to carry out the provisions of this Agreement, the Notes and the Warrants and to
carry on its Business as currently conducted and as currently proposed to be conducted. The
Company is duly qualified, is authorized to do business and is in good standing as a foreign
corporation in each jurisdiction in which the nature of its activities and of its properties (both
owned and leased) makes such qualification necessary, except where the failure to so qualify would
not have a material adverse effect on the assets, liabilities, financial condition, operations or
prospects of the Company (a “Material Adverse Effect”).







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          3.2. Subsidiaries. The Company does not have any Subsidiaries (as defined below). The
Company does not own any ownership interest or profits interest in any other corporation, limited
liability company, limited partnership or other entity. The Company is not a participant in any
joint venture, partnership or similar arrangement. For the purposes of this Agreement,
"Subsidiaries” means, with respect to any Person (as defined below) (including the Company), any
corporation, partnership, association or other business entity of which more than 50% of the issued
and outstanding stock or equivalent thereof having ordinary voting power is owned or controlled by
such Person, by one or more Subsidiaries or by such Person and one or more Subsidiaries of such
Person. For purposes of this Agreement, “Person” means any individual, corporation, partnership,
firm, joint venture, association, limited liability company, limited liability partnership,
joint-stock company, trust, unincorporated organization or governmental entity.




          3.3. Capitalization; Voting Rights. The authorized capital stock of the Company,
immediately prior to the Closing, consists of: (i) 73,050,000 shares of Common Stock, par value
$0.001 per share, of which 3,131,250 shares are issued and outstanding and an aggregate of
8,366,095 shares are reserved for future issuance pursuant to the NuPathe Inc. 2005 Equity
Compensation Plan, as amended (the “Company Equity Incentive Plan”), and (ii) 53,967,262 shares of
preferred stock, par value $0.001 per share (the “Preferred Stock”), 17,056,914 of which are
designated Series A Preferred Stock, $0.001 par value per share (“Series A Preferred Stock”),
16,922,506 of which are issued and outstanding, and 36,910,348 of which are designated Series B
Preferred Stock, 36,173,834 of which are issued and outstanding; and immediately prior to the
Closing, all issued and outstanding shares of the Company’s Common Stock, Series A Preferred Stock
and Series B Preferred Stock (1) have been duly authorized and validly issued to the persons listed
on Exhibit E-1 hereto in the amounts set forth thereon, (2) are fully paid and
nonassessable, and (3) were issued in compliance with all applicable state and federal laws
concerning the issuance of securities. When issued in compliance with this Agreement, the Notes,
the Warrants and the Certificate, the Securities will be, except as set forth on Schedule
3.3, free of any liens or encumbrances other than liens and encumbrances created by or imposed
upon the Purchasers; provided, however, that the Shares, the Warrant Shares, the Conversion Shares
and the Warrant Conversion Shares may be subject to restrictions on transfer under the Related
Agreements (as defined below) and state and/or federal securities laws. The Shares and the
Conversion Shares have been duly and validly reserved for issuance. The rights, preferences,
privileges and restrictions of the Series B Preferred Stock and the Common Stock are as stated in
the Certificate. Except as set forth on Schedule 3.3, and except as may be granted
pursuant to the Related Agreements, there are no outstanding options, warrants, rights (including
conversion or preemptive rights and rights of first refusal), or other agreements of any kind for
the purchase or acquisition from the Company of any of its securities. Except as set forth on
Schedule 3.3 and except as may be granted pursuant to the Related Agreements, there are no
proxies, stockholder agreements or any other agreements between the Company and any stockholder of
the Company or, to the Company’s Knowledge, between any stockholders of the Company, related to the
capital stock of the Company, including agreements relating to the voting of the capital stock of
the Company. Except as set forth in the Company Equity Incentive Plan or on Schedule 3.3,
no stock plan, stock purchase agreement, stock option agreement or other equity-based agreement or
understanding between the Company and any holder of any equity securities or rights to purchase
equity securities provides for acceleration or other changes in the vesting provisions or other
terms of such agreement or understanding as the result of any merger, consolidation, sale of stock
or assets, change in control or other similar transaction by the Company. The total outstanding
capital stock of the Company on a fully diluted basis immediately following the Closing on a pro
forma basis will be as set forth as Exhibit E-2. For purposes of this Agreement, “Related
Agreements” means the Amended and Restated Investor Rights Agreement, dated as of July 8, 2008, by
and among the Company and the other parties named therein (the “Investor Rights Agreement”) and the
Amended and Restated Stockholders Agreement, dated as of July 8, 2008, by and among the Company and
the other parties named therein (the “Stockholders Agreement”).







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          3.4. Authorization; Binding Obligations. All actions by or on behalf of the Company
or the stockholders necessary for the authorization of this Agreement, the Notes and the Warrants,
the performance of all obligations of the Company hereunder and thereunder at the Closing and the
authorization, sale, issuance and delivery of the Notes and the Warrants pursuant hereto and the
authorization and reservation of the Shares, the Warrant Shares, the Conversion Shares and the
Warrant Conversion Shares pursuant to the Certificate have been taken or will be taken prior to the
Closing. This Agreement (assuming due execution and delivery by the Purchasers), the Notes and the
Warrants, when executed and delivered, will be valid and binding obligations of the Company,
enforceable against the Company in accordance with their respective terms, except (a) as limited by
applicable bankruptcy, insolvency, reorganization, moratorium or other laws of general application
affecting enforcement of creditors’ rights, (b) as limited by general principles of equity that
restrict the availability of equitable remedies, and (c) to the extent that the enforceability of
the indemnification provisions of Sections 2.9 or 3.14 of the Investor Rights Agreement may be
limited by applicable law.




          3.5. Financial Statements. The Company has delivered, or will deliver, to the
Purchasers (a) the unaudited financial statements (balance sheet, statement of operations, and
statement of cash flows) of the Company as of and for the year ended December 31, 2009 and (b) the
unaudited financial statements (balance sheet, statement of operations, and statement of cash
flows) of the Company as of and for the two (2) months ended February 28, 2010, copies of which are
attached hereto as part of Schedule 3.5 (collectively, the “Financial Statements”). The
Financial Statements, together with the notes thereto, have been prepared in accordance with
generally accepted accounting principles applied on a consistent basis throughout the periods
indicated, and are complete and correct in all material respects and present fairly, in all
material respects, the results of operations, financial condition and position of the Company as of
the dates presented, subject (in the case of unaudited financial statements) to normal year-end
adjustments, which adjustments will not be materially adverse to the Company, and an absence of
footnotes.




          3.6. Liabilities. The Company does not have any direct or indirect liabilities,
indebtedness or obligations, known or unknown, asserted or unasserted and whether accrued,
absolute, contingent, matured or unmatured (collectively, “Liabilities”), that are not disclosed in
the Financial Statements, incurred in the ordinary course of business since the date thereof or set
forth on Schedule 3.6 attached hereto, other than Liabilities incurred in the ordinary
course of business after February 28, 2010 (the “Statement Date”) that are not individually in
excess of $25,000 or in excess of $100,000 in the aggregate. The Company is not a guarantor or
indemnitor of any indebtedness of any other Person.




          3.7. Litigation. There is no action, suit or proceeding pending or, to the Company’s
Actual Knowledge, any threatened action, suit or proceeding against the Company or any
investigation of the Company.




          3.8. Tax Returns and Payments. The Company has timely filed all tax returns, or
timely filed appropriate extensions for such returns, required to be filed by it, and the Company
has timely paid all taxes owed by it (whether or not shown on any tax return).




          3.9. Real Property Holding Corporation. The Company is not, and has not ever been, a
“United States real property holding corporation” as that term is defined in Section 897 of the
Internal Revenue Code of 1986, as amended.




          3.10. Consents; Approvals. No consent, approval, waivers or authorization of, or
designation, declaration or filing with any court, governmental authority or instrumentality or
arbitrator or any other Person is required in connection with the valid execution, delivery and
performance of this Agreement, the Notes and the Warrants (including, without limitation, the
issuance of the Shares, the






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Warrant Shares or the Conversion Shares), except such filings that have been duly and validly
obtained or filed, or with respect to any filings that must be made after the Closings as will be
filed in a timely manner.




          3.11. Offering Valid. Assuming the accuracy of the representations and warranties of
the Purchasers contained in Section 4.2 hereof, the offer, sale and issuance of the Securities will
be exempt from the registration requirements of the Securities Act of 1933, as amended (the
"Securities Act”) and will have been registered or qualified (or are exempt from registration and
qualification) under the registration, permit or qualification requirements of all applicable state
securities laws.




          3.12. Compliance with Laws; Permits. The Company is not in violation of any
applicable statute, rule, regulation, order or restriction of any domestic or foreign government of
any instrumentality or agency thereof in respect of the conduct of the Business or the ownership of
its properties which violation would have a Material Adverse Effect.




          3.13. Investment Company Act. The Company is not an “investment company”, or a
company “controlled” by an “investment company”, within the meaning of the Investment Company Act
of 1940, as amended.




          3.14. No Broker. The Company has not employed any broker or finder, or incurred any
liability for any brokerage or finders fees or any similar fees or commissions in connection with
the transactions contemplated by this Agreement.




     4. REPRESENTATIONS AND WARRANTIES OF THE PURCHASERS.



          Each Purchaser hereby represents and warrants to the Company, severally, individually and not
jointly, as follows, as of the date hereof:




          4.1. Requisite Power and Authority. Purchaser has all necessary power and authority
under all applicable provisions of law to execute and deliver this Agreement, to consummate the
transactions contemplated hereby and thereby and to perform its obligations hereunder and
thereunder. All actions on Purchaser’s part required for the lawful execution and delivery of this
Agreement, the consummation of the transactions contemplated hereby and thereby and the performance
of all obligations of Purchaser hereunder and thereunder, have been or will be effectively taken
prior to the Closing. Upon their execution and delivery, this Agreement will be a valid and
binding obligation of Purchaser, enforceable in accordance with their terms, except (a) as limited
by applicable bankruptcy, insolvency, reorganization, moratorium or other laws of general
application affecting enforcement of creditors’ rights, (b) as limited by general principles of
equity that restrict the availability of equitable remedies, and (c) to the extent that the
enforceability of the indemnification provisions of Section 2.9 or 3.14 of the Investor Rights
Agreement may be limited by applicable laws.




          4.2. Investment Representations. Purchaser understands that none of the Securities
have been registered under the Securities Act, under any state securities laws or under securities
laws of any other jurisdiction. Purchaser also understands that the Securities are being offered
and sold pursuant to an exemption from registration contained in the Securities Act based in part
upon Purchaser’s representations contained in this Agreement. Purchaser hereby represents and
warrants as follows:




               (a) Purchasers Bear Economic Risk. Purchaser understands that the Securities will be
“restricted securities” under applicable securities laws inasmuch as they are being acquired from
the Company in a transaction not involving a public offering and that under such laws and
applicable regulations the Securities may be resold without registration and/or qualification under
the



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Securities Act only in certain limited circumstances. Purchaser has substantial experience in
evaluating and participating in private placement transactions of securities in companies similar
to the Company so that it is capable of evaluating the merits and risks of its purchase of
securities in the Company and has the capacity to protect its own interests. Purchaser is capable
of bearing the economic risk of this purchase indefinitely and is able to bear a complete loss of
its holdings in the Company. Purchaser also represents that it has not been organized for the
purpose of acquiring the Securities.




               (b) Acquisition for Own Account. Purchaser is acquiring the Securities for its own
account, not as nominee or agent, and not with a view towards their resale or distribution or any
part thereof, and Purchaser has no present intention of selling, granting any participation in or
otherwise distributing the same. By executing this Agreement, Purchaser further represents that
Purchaser does not have any contract, undertaking, agreement or arrangement with any Person to
sell, transfer or grant participations to such Person or to any third Person, with respect to any
of the Securities.



               (c) Accredited Investor. Purchaser is an “accredited investor” within the meaning of
Regulation D under the Securities Act.



               (d) Discussions with the Company; Access to Information. Purchaser has had an
opportunity to discuss the Company’s Business, management and financial affairs with the Company’s
management. Purchaser has had an opportunity to ask questions of and receive answers from,
officers of the Company. Purchaser has made, either alone or together with its advisors, such
independent investigation of the Company, its management and related matters as it deems to be, or
as such advisors have advised to be, necessary or advisable in connection with the purchase of the
Securities; and to Purchasers knowledge, Purchaser and its advisors have received all information
and data that they, and such advisors, believe to be necessary in order to reach an informed
decision as to the advisability of the purchase of the Securities, bearing in mind (among other
factors, without limitation) that Purchaser may not be able to dispose of the Securities for the
indefinite future.



          4.3. Transfer Restrictions. Purchaser acknowledges and agrees that the Shares and the
Warrant Shares and, if issued, the Conversion Shares, are subject to restrictions on transfer as
set forth in the Related Agreements and/or applicable state and/or federal securities laws.




          4.4. Litigation. There is no action, suit, proceeding or investigation pending, or to
each Purchaser’s knowledge, currently threatened against Purchaser which, if adversely determined,
would, individually or in the aggregate, have a material adverse effect on the ability of Purchaser
to perform its obligations under this Agreement and to consummate the transactions contemplated
hereby.




          4.5. No Broker. Purchaser has not employed any broker or finder, or incurred any
liability for any brokerage or finders fees or any similar fees or commissions in connection with
the transactions contemplated by this Agreement.




          4.6. Residence. The office or offices of Purchaser in which it made its decision to
purchase the Securities is located at Purchaser’s respective address set forth beneath Purchaser’s
name on the signature pages hereto.




     5. CONDITIONS TO CLOSING.



          5.1. Conditions to Purchasers’ Obligations at the Closings. The obligations of the
Purchasers to consummate the transactions contemplated herein is subject to the satisfaction, on or
prior to the date of the Closing, of the conditions set forth below.







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               (a) Representations and Warranties; Performance of Obligations. Each of the
representations and warranties of the Company contained herein shall be true and correct on and as
of the Initial Closing Date. As of the Initial Closing, the Company shall have performed and
complied with the covenants and provisions of this Agreement required to be performed or complied
with by it at or prior to the Initial Closing Date. At the Initial Closing, the Purchasers shall
have received certificates of the Company dated as of the date of the Initial Closing, signed by an
officer of the Company, certifying as to the fulfillment of the conditions set forth in this
Section 5.1 and the truth and accuracy of the representations and warranties of the Company
contained herein (as qualified by the Schedules) as of the Initial Closing Date.



               (b) Issuance in Compliance with Laws. The sale and issuance of the Notes and the
Warrants and the proposed issuance of the Shares, Warrant Shares and Conversion Shares shall be
legally permitted by all laws and regulations to which any of the Purchasers and the Company are
subject.



               (c) Filings, Consents, Permits, and Waivers. The Company and the Purchasers shall
have made all filings and obtained any and all consents, permits and waivers necessary for
consummation of the transactions contemplated by the Agreement.



               (d) Reservation of Shares, Warrant Shares and Conversion Shares. The Shares issuable
upon conversion of the Notes and the Conversion Shares shall have been duly authorized and reserved
for issuance upon such conversion. The Warrant Shares issuable upon the exercise of the Warrants
and the Conversion Shares shall have been duly authorized and reserved for issuance upon such
exercise or conversion, as applicable.



               (e) Proceedings and Documents. All corporate and other proceedings in connection with
the transactions contemplated at the applicable Closing and all documents and instruments incident
to such transactions shall be reasonably satisfactory in substance and form to the Purchasers and
their counsel, and the Purchasers and their counsel shall have received all such counterpart
originals or certified or other copies of such documents as they may reasonably request.



               (f) Proceedings and Litigation. No action, suit or proceeding shall have been
commenced by any governmental authority against any party hereto seeking to restrain or delay the
purchase and sale of Shares or the other transactions contemplated by this Agreement.



               (g) No Material Adverse Effect. There shall have occurred no event or condition that
has had, or reasonably could be expected to have, a Material Adverse Effect or which could
adversely affect the Company’s ability to perform its obligations under this Agreement.



               (h) Purchaser Approvals. As of the Initial Closing, all requisite approvals of the
general partners or investment committees, as applicable, of each Purchaser necessary for the
performance of the transactions contemplated by this Agreement shall have been obtained.



               (i) Approval of Safeguard. As of the Initial Closing, all approvals of Safeguard
Delaware, Inc., necessary for the performance of the transactions contemplated by this Agreement
shall have been obtained.



               (j) Secretary’s Certificate. The Company shall have executed and delivered to the
Purchasers a certificate of the Secretary of the Company attaching (A) the Certificate as in effect
at the Initial Closing, (B) the Bylaws of the Company in effect at the Initial Closing, (C) copies
of resolutions by the Board of Directors authorizing and approving this Agreement, the issuance and
delivery of the Notes, Warrants, Shares, Warrant Shares and the Conversion Shares, and an amendment
to



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the Certificate required thereby (the “Amendment”), and copies of resolutions by the
stockholders of the Company authorizing and approving the transactions contemplated by this
Agreement and the Amendment (collectively, the “Resolutions”); and (D) certifying as to the
incumbency of the officers executing this Agreement, the Notes, the Warrants and any other
documents contemplated by this Agreement.




               (k) Security Agreement. The Company shall have executed and delivered a Security
Agreement in form and substance reasonably acceptable to the Purchasers and their counsel (the
“Security Agreement”).



               (l) Subordination Agreement. The Company and Oxford Finance Corporation shall have
executed and delivered a Subordination Agreement with respect to the subordination of the
indebtedness evidenced by the Notes (the “Subordination Agreement”).



          5.2. Conditions to Obligations of the Company. The obligation of the Company to
consummate the transactions contemplated herein to be consummated at each Closing is subject to the
satisfaction, on or prior to such Closing of the conditions set forth below.




               (a) Representations and Warranties; Performance of Obligations. Each of the
representations and warranties of the Purchasers contained herein shall be true and correct on and
as of the date of such Closing. As of the date of such Closing, the Purchasers shall have
performed and complied with the covenants and provisions of this Agreement required to be performed
or complied with by them at or prior to the date of such Closing.



               (b) Proceedings and Litigation. No action, suit or proceeding shall have been
commenced by any governmental authority against any party hereto seeking to restrain or delay the
purchase and sale of the Securities or the other transactions contemplated by this Agreement.



               (c) Subordination Agreement. The Purchasers and Oxford Finance Corporation shall have
executed and delivered the Subordination Agreement.



     6. COVENANTS OF THE PARTIES.



          6.1. Directors’ and Officers’ Insurance. The Company shall maintain the Directors’
and Officers’ insurance described in Section 3.11 of the Investor Rights Agreement.




          6.2. Key Person Life Insurance. The Company shall maintain a key person life
insurance policy on the life of each of Jane H. Hollingsworth and Terri B. Sebree in an aggregate
amount of $2,000,000 per individual, the proceeds of which shall be payable to the Company.




          6.3. Reservation of Stock. As of or prior to Initial Closing, the Company shall, and
shall cause its stockholders to, take any and all action necessary to reserve for issuance the
number of Shares, Warrant Shares, Conversion Shares and Warrant Conversion Shares into which all of
the Notes and Warrants to be sold or issued hereunder are convertible or exercisable, as
applicable, and shall take (or cause to be taken) such further action from time to time thereafter
to increase the number of Conversion Shares or Warrant Conversion Shares reserved for issuance as
required by any increase in the number of Conversion Shares into which the Shares and Warrant
Shares may then be converted.




          6.4. Commercially Reasonable Efforts. Upon the terms and subject to the conditions
set forth in this Agreement, the parties shall use their good faith commercially reasonable efforts
to take, or cause to be taken, without any party being obligated to incur any material internal
costs or make any






-9-









 







payment or payments to any third party or parties which, individually or in the aggregate, are
material and are not otherwise legally required to be made, all actions, and to do or cause to be
done, and to assist and cooperate with the other parties in doing, all things necessary, proper or
advisable to consummate and make effective, in the most expeditious manner practicable, the Closing
and the other transactions contemplated hereunder, including (a) obtaining all required consents,
and (b) the execution and delivery of any additional documents, agreements and instruments (in form
and substance reasonably satisfactory to the parties) necessary to consummate the transactions
contemplated hereunder and to fully carry out the purposes of this Agreement.




          6.5. Post-Closing Filings. In connection with the Closing, the Company and the
Purchasers, if required, agree to file all required forms or filings under applicable laws within
the time required by such laws, including the filing of any UCC financing statements required
pursuant to the Security Agreement.




          6.6. Amendment of Certificate. The Company shall, immediately prior to the exercise
of the Warrants, take all necessary actions to amend the Certificate to authorize, solely for the
purpose of issuance upon exercise of such Warrants, such number and kind of shares of capital stock
as may then be issuable upon the exercise of the Warrants, including, without limitation, the
Warrant Shares. The Company covenants that all shares of capital stock which shall be so issuable
will, upon the exercise of the Warrant, be duly and validly issued and fully paid and nonassessable
by the Company.




          6.7. Affixation of Legend. The Company shall affix a legend to each Note stating that
such Note is subject to the terms of the Subordination Agreement, as it may be amended, restated or
modified from time to time.




     7. MISCELLANEOUS.



          7.1. Indemnification.




               (a) The Company agrees to indemnify, defend and hold harmless the Purchasers and their
affiliates and their respective officers, directors, trustees, agents, representatives, employees,
partners and controlling persons (each, an “Indemnified Party”) against any and all Losses (as
hereinafter defined) arising out of or relating to any legal, administrative or other actions
(including actions brought by the Purchasers or the Company or any equity holders of the Company or
any derivative actions brought by any Person claiming through or in the Company’s name),
proceedings or investigations (whether formal or informal), or written threats thereof, based upon,
resulting from, relating to or arising out of any misrepresentation or breach of any
representation, warranty, covenant or agreement by the Company in this Agreement or in any of the
Notes and the Warrants.



               (b) The Company shall indemnify, defend and hold harmless each Indemnified Party against any
and all Losses of such Indemnified Party resulting from or arising out of any third party or
governmental action or claim based upon the Indemnified Party’s status as a security holder of the
Company (including, without limitation, any and all Losses arising under the Securities Act, the
Securities Exchange Act of 1934, as amended, or similar securities law, any other federal or state
statute, rule, regulation or law, or otherwise, which relate directly or indirectly to the
registration, purchase, sale or ownership of any securities of the Company or to any fiduciary
obligation owed with respect thereto), including, without limitation, in connection with any third
party or governmental action or claim relating to any action taken or omitted to be taken or
alleged to have been taken or omitted to have been taken by such Indemnified Party as a security
holder. Notwithstanding the foregoing, the Company shall not be obligated to indemnify or hold
harmless any Indemnified Party under this Section 7.1(b) against any Losses resulting from or
arising out of any third party or governmental action or claim



-10-









 




if it has been finally determined by a court or other trier of fact of competent jurisdiction
that such Losses were the result of (i) a breach of such Indemnified Party’s fiduciary duty, (ii)
any action or omission made by the Indemnified Party in bad faith or (iii) any criminal action on
the part of such Indemnified Party.




               (c) In connection with the obligation of the Company to indemnify for expenses as set forth in
Sections 7.1(a) and 7.1(b) above, the Company shall reimburse each Indemnified Party for all such
expenses (including reasonable expenses of investigation and reasonable fees, disbursements and
other charges of counsel in connection with any claim, action, suit or proceeding) as they are
incurred by such Indemnified Party. “Losses” means all losses (including the diminution in the
value of the Shares purchased by Purchaser), claims (including any claim by a third party),
damages, expenses (including reasonable fees, disbursements and other charges of counsel incurred
by the Indemnified Party in connection with any claim, action, suit or proceeding, including any
action between the Indemnified Party and the Company or between the Indemnified Party and any third
party) or other Liabilities.



          7.2. Governing Law. This Agreement shall be governed in all respects by the laws of
the State of Delaware without regard to the conflicts of laws principles of any jurisdiction. No
suit, action or proceeding with respect to this Agreement or any of the Notes or Warrants may be
brought in any court or before any similar authority other than in a court of competent
jurisdiction in the State of Delaware, and the parties hereby submits to the exclusive jurisdiction
of such courts for the purpose of such suit, proceeding or judgment. Each of the parties hereto
hereby irrevocably waives any right which it may have had to bring such an action in any other
court, domestic or foreign, or before any similar domestic or foreign authority and agreed not to
claim or plead the same. Each of the parties hereto hereby irrevocably and unconditionally waives
trial by jury in any legal action or proceeding in relation to this Agreement or any of the Notes
or Warrants and for any counterclaim therein.




          7.3. Survival. The representations, warranties, covenants and agreements made herein
shall survive the Closings and any investigation made by the Purchasers for a period of two (2)
years. All statements as to factual matters contained in any certificate delivered by or on behalf
of the Company pursuant hereto in connection with the transactions contemplated hereby shall be
deemed to be representations and warranties made by the Company hereunder solely as of the date of
such certificate.




          7.4. Successors and Assigns. Except as otherwise expressly provided herein, the
provisions hereof shall inure to the benefit of, and be binding upon, the successors and permitted
assigns of the parties hereto. This Agreement may not be assigned without the prior written
consent of the other parties hereto, except that each Purchaser may assign its rights and
obligations hereunder to any affiliate or affiliates without such prior written consent provided
that any such affiliate agrees to be subject to the terms of the Investor Rights Agreement to the
same extent as if such affiliate was an original Holder (as defined in the Investor Rights
Agreement) with respect to any Registrable Securities (as defined in the Investor Rights Agreement)
that may be issued to such affiliate.




          7.5. Entire Agreement. This Agreement, including the Exhibits and Schedules hereto,
and the Notes and Warrants and each of the Exhibits delivered pursuant thereto constitute the full
and entire understanding and agreement between the parties hereto with regard to the subject matter
hereof and thereof and no party hereto shall be liable or bound to any other party hereto in any
manner by any representations, warranties, covenants and agreements except as specifically set
forth herein and therein.




          7.6. Severability. If any provision of the Agreement is held to be invalid, illegal
or unenforceable, the validity, legality and enforceability of the remaining provisions of this
Agreement shall not in any way be affected or impaired thereby.







-11-









 








          7.7. Amendment and Waiver. This Agreement may be amended or modified only upon the
approval of the Company and the written consent of the Purchasers purchasing a majority of the
outstanding principal amount of the Notes including any Notes that have been transferred to
affiliates of the Purchasers.




          7.8. Delays or Omissions. No delay or omission to exercise any right, power or remedy
accruing to any party, upon any breach, default or noncompliance by another party under this
Agreement, the Notes, the Warrants or the Certificate, shall impair any such right, power or
remedy, nor shall it be construed to be a waiver of any such breach, default or noncompliance, or
any acquiescence therein, or of or in any similar breach, default or noncompliance thereafter
occurring. Any waiver, permit, consent or approval of any kind or character on any Purchaser’s
part of any breach, default or noncompliance under this Agreement, the Notes, the Warrants or under
the Certificate or any waiver on such party’s part of any provisions or conditions of the
Agreement, the Notes, the Warrants or the Certificate must be in writing and shall be effective
only to the extent specifically set forth in such writing. All remedies, either under this
Agreement, the Notes, the Warrants, the Certificate, Bylaws of the Company, or otherwise afforded
to any party, shall be cumulative and not alternative.




          7.9. Notices. All notices required or permitted hereunder shall be in writing and
shall be deemed effectively given: (a) upon personal delivery to the party to be notified; (b) when
sent by confirmed telex or facsimile if sent during normal business hours of the recipient, and if
not, then on the next business day; (c) three (3) days after having been sent by registered or
certified mail, return receipt requested, postage prepaid; (d) one (1) day after deposit with a
nationally recognized overnight courier, specifying next day delivery, with written verification of
receipt or (e) when sent by electronic mail, upon confirmation of receipt by the recipient via
electronic mail. All communications shall be sent to the Company at the address as set forth on
the signature page hereof and to the Purchasers at the address set forth on the signature pages
hereto or at such other address as the Company or the Purchasers may designate by ten (10) days
advance written notice to the other parties hereto.




          7.10. Expenses.




               (a) The Company shall pay all costs and expenses that it incurs with respect to the
negotiation, execution, delivery and performance of this Agreement, including, without limitation,
any costs and expenses of its counsel.



               (b) The Company shall pay all of the reasonable fees and expenses incurred by the Purchasers
with respect to the negotiation and execution of this Agreement and the Notes and the Warrants,
including the reasonable fees and expenses of accounting, consulting and legal counsel to the
Purchasers and related due diligence expenses incurred by the Purchasers.



          7.11. Titles and Subtitles. The titles of the sections and subsections of the
Agreement are for convenience of reference only and are not to be considered in construing this
Agreement.




          7.12. Counterparts; Execution by Facsimile Signature. This Agreement may be executed
in any number of counterparts (including execution by facsimile), each of which shall be an
original, but all of which together shall constitute one instrument. This Agreement may be
executed by facsimile signature(s) which shall be binding on the party delivering same, to be
followed by delivery of originally executed signature pages.




          7.13. Acknowledgment. Any investigation or other examination that may have been made
at any time by or on behalf of a party to whom representations and warranties are made in this
Agreement or in any other Notes or Warrants shall not limit, diminish, supersede, act as a waiver
of, or in






-12-









 







any other way affect the representations, warranties and indemnities contained in this
Agreement and the Notes and Warrants, and the respective parties may rely on the representations,
warranties and indemnities made to them in this Agreement and the Notes and Warrants irrespective
of and notwithstanding any information obtained by them in the course of any investigation,
examination or otherwise, whether before or after the Closing.




          7.14. Publicity. Except as otherwise required by law or applicable stock exchange
rules, no announcement or other disclosure, public or otherwise, concerning the transactions
contemplated by this Agreement shall be made, either directly or indirectly, by any party hereto
which mentions another party (or parties) hereto without the prior written consent of such other
party (or parties), which consent shall not be unreasonably withheld, delayed or conditioned.




          7.15. Exculpation by Purchasers. Each Purchaser acknowledges that it is not relying
upon the representations or warranties of any person, firm or corporation, other than the Company
and its officers and directors, in making its investment or decision to invest in the Company. In
addition, each Purchaser acknowledges that the obligations of each Purchaser hereunder are several,
and such Purchaser is not entering into this Agreement in reliance upon the covenants of the other
Purchasers party hereto.




          7.16. No Third Party Beneficiaries. Nothing in this Agreement, express or implied, is
intended to confer on any Person other than the parties hereto or their respective successors and
assigns any rights, remedies, obligations or liabilities under or by reason of this Agreement.




          7.17. Pronouns. All pronouns contained herein, and any variations thereof shall be
deemed to refer to the masculine, feminine or neutral, singular or plural, as to the identity of
the parties hereto may require.




          7.18. Pari Passu Notes. The Purchasers and the Company acknowledge and agree that the
right of payment of all or any portion of the outstanding principal amounts of each of the Notes
and all interest thereon shall be pari passu in right of payment and in all other respects to all
of the other Notes. In the event a Purchaser receives payments in excess of its pro rata share of
the Company’s payments to all of the Purchasers, then such Purchaser shall hold in trust all such
excess payments for the benefit of the other Purchasers and shall pay such amounts held in trust to
such other Purchasers upon demand by such Purchasers.




[Signature Pages Follow]






-13-









 








          IN WITNESS WHEREOF, the parties hereto have executed this Subordinated Convertible Note and
Warrant Purchase Agreement as of the date set forth in the first paragraph hereof.




	 	 	 	 	 
	 	COMPANY:



NUPATHE INC.

 	 
	 	By:  	/s/  Jane H. Hollingsworth
 	 
	 	 	Name:  	Jane H. Hollingsworth 	 
	 	 	Title:  	Chief Executive Officer
	 	

227 Washington Street, Suite 200

Conshohocken, PA 19428

Attention: Chief Executive Officer

Telephone: (484) 567-0130

Facsimile: (484) 567-0136





with a copy to:





Morgan Lewis & Bockius LLP

1701 Market Street

Philadelphia, PA 19103

Attention:    Michael N. Peterson

Telephone:  (215) 963-5025

Facsimile: (215) 963-5001

Email:         mpeterson@morganlewis.com
 
	 



— Subordinated Convertible Note and Warrant Purchase Agreement Signature Pages —






 









 








	 	 	 	 	 
	 	PURCHASERS:



SR ONE, LIMITED

 	 
	 	By:  	/s/  [ILLEGIBLE]
 	 
	 	 	Name:  	 	 
	 	 	Title:  	 
	 	

SR One, Limited

161 Washington Street, Suite 500

Conshohocken, PA  19428

Attention:    General Partner

Telephone: (610) 567 1000

Facsimile:  (610) 567 1039

with a copy to:



Pepper Hamilton LLP

3000 Two Logan Square

Eighteenth and Arch Streets

Philadelphia, PA  19103

Attention: Christopher S. Miller,
Esquire

Telephone: (610) 640-7837

Facsimile: (267) 200-0854

Email: millerc@pepperlaw.com
 
	 





— Subordinated Convertible Note and Warrant Purchase Agreement Signature Pages —



 











 





	 	 	 	 	 	 	 

	 	 	QUAKER BIOVENTURES II, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	QUAKER BIOVENTURES CAPITAL II, L.P.,	 	 
	 

	 	 	 	its general partner	 	 
	 

	 	By:
	 	QUAKER BIOVENTURES CAPITAL II, LLC,	 	 
	 

	 	 	 	its general partner	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Richard S. Kollender	 	 
	 

	 	 	 	 

Name: Richard S. Kollender
	 	 
	 

	 	 	 	Title:   Vice President	 	 






	 	 	 

	 

	 	Quaker BioVentures II, L.P.

Cira Centre

2929 Arch Street

Philadelphia, PA 19104-2868

Attention: Vice President

Telephone: (215) 988-6800

Facsimile:  (215) 988-6801

with a copy to:
	 
	 	 
	 

	 	Pepper Hamilton LLP

3000 Two Logan Square

Eighteenth and Arch Streets

Philadelphia, PA 19103

Attention: Christopher S. Miller, Esquire

Telephone: (610) 640-7837

Facsimile:  (267) 200-0854

Email:        millerc@pepperlaw.com





— Subordinated Convertible Note and Warrant Purchase Agreement Signature Pages —






 









 








	 	 	 	 	 	 	 

	 	 	BIRCHMERE VENTURES III L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	BV3 Management LP, general partner	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	BV3 LLC, general partner	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	BV3GP Investors, LLC,	 	 
	 

	 	 	 	Managing Member	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	Bay City Capital LLC, Manager	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Jeanne Cunicelli	 	 
	 

	 	 	 	 

Jeanne Cunicelli
	 	 
	 

	 	 	 	Authorized Signatory	 	 
	 
	 	 	 	 	 	 
	 	 	One North Shore Center

Suite 201, 12 Federal Street

Pittsburgh, PA 15212

Attention:

Facsimile: (412) 322-3226	 	 
	 
	 	 	 	 	 	 
	 	 	BIRCHMERE VENTURES III TSIB L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	BV3 Management LP, general partner	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	BV3 LLC, general partner	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	BV3GP Investors, LLC,	 	 
	 

	 	 	 	Managing Member	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	Bay City Capital LLC, Manager	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Jeanne Cunicelli	 	 
	 

	 	 	 	 

Jeanne Cunicelli
	 	 
	 

	 	 	 	Authorized Signatory	 	 
	 
	 	 	 	 	 	 
	 	 	One North Shore Center

Suite 201, 12 Federal Street

Pittsburgh, PA 15212

Attention:

Facsimile: (412) 322-3226	 	 






— Subordinated Convertible Note and Warrant Purchase Agreement Signature Pages —






 









 








	 	 	 	 	 	 	 

	 	 	SAFEGUARD DELAWARE, INC.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Stephen T. Zarrilli	 	 
	 

	 	 	 	 

Name: Stephen T. Zarrilli
	 	 
	 

	 	 	 	Title:   SVP/CFO	 	 
	 
	 	 	 	 	 	 
	 	 	1 1105 N. Market St.

Suite 1300

Wilmington, DE 19801

Attention: Dee Blackburn	 	 
	 
	 	 	 	 	 	 
	 	 	with a copy to:	 	 
	 
	 	 	 	 	 	 
	 	 	Safeguard Delaware, Inc. 

435 Devon Park Drive

Building 800

Wayne, PA 19087

Attention: General Counsel

Fax: 610-293-0601	 	 






— Subordinated Convertible Note and Warrant Purchase Agreement Signature Pages —






 









 








	 	 	 	 	 	 	 

	 	 	BATTELLE VENTURES, LP	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	BVP GP, LLC, its General Partner	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Tracy S. Warren	 	 
	 

	 	 	 	 

Name: Tracy S. Warren
	 	 
	 

	 	 	 	Title:    Member	 	 
	 
	 	 	 	 	 	 
	 	 	103 Carnegie Center, Suite 100

Princeton, NJ 08540

Attention: Tracy Warren, General Partner

Facsimile No: (609) 921-8703	 	 
	 
	 	 	 	 	 	 
	 	 	INNOVATION VALLEY PARTNERS, LP	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	IVP GP, LLC, its General Partner	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Tracy S. Warren	 	 
	 

	 	 	 	 

Name: Tracy S. Warren
	 	 
	 

	 	 	 	Title:    Member	 	 
	 
	 	 	 	 	 	 
	 	 	103 Carnegie Center, Suite 100

Princeton, NJ 08540

Attention: Tracy Warren, General Partner

Facsimile No: (609) 921-8703	 	 






— Subordinated Convertible Note and Warrant Purchase Agreement Signature Pages —






 









 








	 	 	 	 	 	 	 

	 

	 	By:
	 	/s/ Jane H. Hollingsworth	 	 
	 

	 	 	 	Jane H. Hollingsworth

	 	 
	 
	 	 	 	 	 	 
	 	 	
NuPathe Inc.

227 Washington Street, Suite 200

Conshohocken, PA 19428	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Suzanne M. Hanlon	 	 
	 

	 	 	 	 

Suzanne M. Hanlon
	 	 
	 
	 	 	 	 	 	 
	 	 	NuPathe Inc.

227 Washington Street, Suite 200

Conshohocken, PA 19428	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Keith A. Goldan	 	 
	 

	 	 	 	 

Keith Goldan
	 	 
	 
	 	 	 	 	 	 
	 	 	NuPathe Inc.

227 Washington Street, Suite 200

Conshohocken, PA 19428	 	 





— Subordinated Convertible Note and Warrant Purchase Agreement Signature Pages —



 









 








EXHIBIT A — SCHEDULE OF PURCHASERS




	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	Column A	 	Column B	 	Column C	 	Column D
	 	 	Pro Rata Share of	 	Principal Amount	 	Principal Amount	 	Aggregate Principal
	Name of Purchaser	 	the Notes	 	for Initial Closing	 	for Second Closing	 	Amount
	SR One, Limited
	 	 	11.25	%	 	$	1,132,075	 	 	 	—	 	 	$	1,132,075	 
	Quaker BioVentures II, L.P.
	 	 	33.75	%	 	$	3,396,226	 	 	 	—	 	 	$	3,396,226	 
	Safeguard Delaware, Inc.
	 	 	27.00	%	 	$	2,716,981	 	 	 	—	 	 	$	2,716,981	 
	Birchmere Ventures III, L.P.
	 	 	8.88	%	 	$	794,771	 	 	$	98,814	 	 	$	893,585	 
	Birchmere Ventures III TSIB, L.P.
	 	 	5.00	%	 	$	447,059	 	 	$	55,583	 	 	$	502,642	 
	Battelle Ventures, LP
	 	 	12.15	%	 	$	1,222,642	 	 	 	—	 	 	$	1,222,642	 
	Innovation Valley Partners, LP
	 	 	1.35	%	 	$	135,849	 	 	 	—	 	 	$	135,849	 
	Jane H. Hollingsworth
	 	 	0.50	%	 	$	50,000	 	 	 	—	 	 	$	50,000	 
	Suzanne Hanlon
	 	 	0.05	%	 	$	5,000	 	 	 	—	 	 	$	5,000	 
	Keith Goldan
	 	 	0.07	%	 	$	7,500	 	 	 	—	 	 	$	7,500	 
	Total
	 	 	100	%	 	$	9,908,103	 	 	$	154,397	 	 	$	10,062,500	 






 









 






EXHIBIT B




FORM OF SECURED SUBORDINATED CONVERTIBLE PROMISSORY NOTE





 










 






THIS NOTE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR UNDER
ANY STATE OR FEDERAL SECURITIES LAWS AND MAY NOT BE SOLD, TRANSFERRED, OR ASSIGNED EXCEPT: (1)
PURSUANT TO THE EFFECTIVE REGISTRATION THEREOF UNDER SUCH ACT; OR (2) IF, IN THE OPINION OF COUNSEL
FOR THE REGISTERED OWNER HEREOF, WHICH OPINION IS REASONABLY SATISFACTORY TO THE COMPANY, THE
PROPOSED SALE, TRANSFER OR ASSIGNMENT MAY BE EFFECTED WITHOUT SUCH REGISTRATION AND WILL NOT BE IN
VIOLATION OF APPLICABLE STATE AND/OR FEDERAL SECURITIES LAWS.



IN ACCORDANCE WITH THE TERMS OF A SUBORDINATION AGREEMENT, DATED AS OF APRIL 9, 2010 (THE
“SUBORDINATION AGREEMENT”), BY AND AMONG THE PURCHASERS (AS DEFINED HEREIN), THE COMPANY (AS
DEFINED HEREIN) AND OXFORD FINANCE CORPORATION (THE “SENIOR LENDER”), THE PURCHASER HAS
SUBORDINATED THE INDEBTEDNESS EVIDENCED BY THIS SECURED SUBORDINATED CONVERTIBLE PROMISSORY NOTE
(THE “NOTE”) AND ANY SECURITY INTEREST OR LIEN THAT THE PURCHASER MAY HAVE IN ANY PROPERTY OF THE
COMPANY TO THE INDEBTEDNESS OWED BY THE COMPANY TO SENIOR LENDER AND THE SECURITY INTEREST OF
SENIOR LENDER IN THE ASSETS OF THE COMPANY, NOTWITHSTANDING THE RESPECTIVE DATES OF ATTACHMENT OR
PERFECTION OF THE SECURITY INTEREST OF THE PURCHASER AND SENIOR LENDER. IN THE EVENT OF ANY
INCONSISTENCY BETWEEN THE NOTE AND THE SUBORDINATION AGREEMENT, THE TERMS OF THE SUBORDINATION
AGREEMENT SHALL CONTROL.




SECURED SUBORDINATED CONVERTIBLE PROMISSORY NOTE




			
	 	 	 
	$                    
	 	Issue Date: April 9, 2010






     For Value Received, NuPathe Inc., a Delaware corporation (the “Company”), promises to
pay to                
               
           or its assigns (the “Purchaser”) the principal sum of
               
               
           Dollars ($   
               
  ) together with interest on the outstanding principal amount
at the annual rate of 8%, compounding monthly. Interest shall commence on the date hereof and
shall continue on the outstanding principal until paid in full or converted in accordance with the
provisions hereof. Interest shall be computed on the basis of a year of 365 days for the actual
number of days elapsed. This Note is one of a series of secured subordinated convertible
promissory notes issued by the Company pursuant to that certain Subordinated Convertible Note and
Warrant Purchase Agreement, dated as of April 9, 2010, by and among the Company, the Purchaser and
the other parties named therein (as the same may be amended from time to time, the “Purchase
Agreement”), and is entitled to the benefits of the Purchase Agreement. Such secured subordinated
convertible promissory notes are collectively referred to as “Notes” and the holders of the Notes
are collectively referred to as “Purchasers.” Terms used, but not otherwise defined herein, shall
have the meanings ascribed to such terms in the Purchase Agreement.



 








 





     1. Payments. All payments of interest and principal shall be in lawful money of the United
States of America. All payments shall be applied first to costs of collection, if any (but only if
such costs of collection are incurred after an Event of Default), then to the payment of accrued
interest, and thereafter to principal. Payments of principal and interest shall be made, at the
election of the Purchaser, by check or wire transfer of immediately available lawful money of the
United States of America sent to the holder at the address or bank account, as the case may be,
furnished to the Company for such purpose.



     2. No Prepayment. Subject to the terms of the Subordination Agreement, the Company may not
prepay, redeem or otherwise acquire this Note prior to the Maturity Date (as defined below) without
the prior written consent of the holders of Notes representing at least a majority of the then
outstanding aggregate principal amount of the Notes (the “Majority Holders”).



     3. Security. The indebtedness of the Company arising under this Note is secured by the
Security Documents. “Security Documents” shall mean all mortgages, instruments, pledge agreements,
assignments, acceptance agreements, financing statements, stock powers and any other agreements,
documents and instruments, now or hereafter existing, creating, perfecting or relating to the
obligations under this Note, together with all amendments, modifications, renewals, extensions or
restatements thereof, in each case subject to the terms of the Subordination Agreement.



     4. Mandatory Conversion.



          (a) Public Offering Conversion. In the event that the Company consummates an initial firm
commitment underwritten offering of the Company’s Common Stock pursuant to an effective
registration statement under the Securities Act of 1933, as amended (the “Securities Act”) (such
offering, an “IPO”) on or before the Maturity Date, then simultaneous with the initial closing of
the IPO, the outstanding principal balance of this Note, together with all accrued and unpaid
interest under this Note, shall automatically convert without any further action by the Purchaser
into shares of the Company’s Common Stock at a conversion price equal to eighty percent (80%) of
the price per share at which shares of the Company’s Common Stock are sold to the public in the
IPO. Upon issuance, such shares shall not be registered under the Securities Act but the Purchaser
shall have the registration rights with respect thereto set forth in the Company’s Amended and
Restated Investor Rights Agreement, dated as of July 8, 2008, as amended.




          (b) Acquisition Conversion. In the event that the Company enters into a definitive agreement
to effect a Liquidity Event (as defined in the Company’s Third Amended and Restated Certificate of
Incorporation, as amended from time to time) on or before the Maturity Date (an “Acquisition
Transaction”) then, immediately prior to the closing of the Acquisition Transaction, the
outstanding principal balance of this Note, together with all accrued and unpaid interest under
this Note, shall convert in whole without any further action by the Purchaser into shares of the
Company’s Series B Preferred Stock at a per share conversion price equal to eighty percent (80%) of
the price for which the Company’s Series B Preferred Stock was last sold (currently $0.93) (the
“Acquisition Conversion Price”).







 2.









 








          (c) Financing Conversion. In the event that on or before the Maturity Date the Company issues
and sells Equity Securities (as defined below) to investors acceptable to the Majority Holders (the
“Investors”) in an equity financing with total proceeds to the Company of not less than Ten Million
Dollars ($10,000,000) (excluding the conversion of the amounts outstanding under the Notes) (a
“Qualified Financing”), then the outstanding principal balance of this Note, together with all
accrued and unpaid interest under this Note, shall automatically convert without any further action
by the Purchaser into shares of such Equity Securities sold in the Qualified Financing at a
conversion price equal to the price per share paid by the Investors purchasing such Equity
Securities (the “Qualified Financing Conversion Price”), and the issuance of such Equity Securities
to the Purchaser shall have the same terms and conditions as given to the Investors in the
Qualified Financing. For purposes of this Note, the term “Equity Securities” shall mean Preferred
Stock of the Company (“Preferred Stock”) that has a liquidation preference, dividend rights and
other similar rights that are senior to, or pari passu with, the most senior existing series of
Preferred Stock.




     5. Optional Conversion. If this Note is outstanding on the Maturity Date and the Company has
not (i) filed an effective registration statement under the Securities Act with respect to an IPO
or (ii) entered into a definitive agreement with respect to an Acquisition Transaction, the
Majority Holders may elect by written consent to convert the outstanding principal balance of all
Notes (including this Note), together with all accrued and unpaid interest under all Notes
(including this Note), without any further action by any Purchaser, into shares of the Company’s
Series B Preferred Stock at a per share conversion price equal to eighty percent (80%) of the price
for which the Company’s Series B Preferred Stock was last sold (currently $0.93) (the “Optional
Conversion Price”).



     6. Maturity Date. If this Note has not previously been converted in accordance with the terms
of Sections 4 or 5 above, and the Company has not (i) filed an effective registration
statement under the Securities Act with respect to an IPO or (ii) entered into a definitive
agreement with respect to an Acquisition Transaction, then the entire outstanding principal balance
together with all accrued and unpaid interest under this Note shall be due and payable on December
31, 2010 (the “Maturity Date”).



     7. Event of Default. Subject to the terms of the Subordination Agreement, the outstanding
principal amount of this Note plus all accrued and unpaid interest thereon shall, at the election
of the Majority Holders, become immediately due and payable without notice or demand, upon the
happening of any one of the following specified events, whatever the reason for such event and
whether it shall be voluntary or involuntary, or within or without the control of the Company, or
be effected by operation of law or pursuant to any judgment or order of any court or any order,
rule or regulation of any governmental authority (each, an “Event of Default”):



          (a) the Company’s failure to pay any amount as herein set forth and such nonpayment shall
continue uncured for a period of five (5) business days after written notice by the Purchaser
thereof;




          (b) the making of a general assignment for the benefit of creditors by the Company;







 3.









 








          (c) the filing of any petition or the commencement of any proceeding against the Company or
any endorser or guarantor of this Note for any relief under any bankruptcy or insolvency laws, or
any laws relating to the relief of debtors, readjustment of indebtedness, reorganizations,
compositions, or extensions, which proceeding is not dismissed within sixty (60) days;




          (d) the failure to observe or perform any covenant or agreement required to be observed or
performed by the Company under this Note or the Purchase Agreement or under any document,
instrument or agreement executed and delivered in connection with this Note (collectively, the
“Related Documents”), and such failure shall continue after the expiration of ten (10) business
days following notice from the Purchaser of such failure;




          (e) any representation or warranty of the Company under any Related Document shall have been
false or misleading in any material respect when made; or




          (f) the Company defaults in the payment of any other obligation for borrowed money, which
default is not (i) cured within any grace or cure period applicable thereto or (ii) otherwise
waived by the applicable lender.




     8. Default Rate. Beginning on the occurrence of any Event of Default and during the
continuance thereof, this Note shall bear interest at a rate that shall be five percentage points
(5.0%) in excess of the interest rate in effect from time to time under this Note, but in no event
shall such rate exceed the maximum rate then allowable by law (the “Default Rate”). The Default
Rate shall continue to apply whether or not judgment shall be entered on this Note. The Company
agrees that the Default Rate is imposed as liquidated damages for the purpose of defraying the
Purchaser’s expenses incident to the handling of delinquent payments, but is in addition to, and
not in lieu of, the Purchaser’s exercise of any rights and remedies hereunder, or under applicable
law, and any fees and expenses of any agents or attorneys which the Purchaser may employ. In
addition, the Company acknowledges that the Default Rate reflects the increased credit risk to the
Purchaser of carrying a loan that is in default. The Company agrees that the Default Rate is a
reasonable forecast of just compensation for anticipated and actual harm incurred by the Purchaser,
and that the actual harm incurred by the Purchaser cannot be estimated with certainty and without
difficulty.



     9. Remedies Cumulative, etc.



          (a) No right or remedy conferred upon or reserved to the Purchaser is intended to be exclusive
of any other right or remedy, and each and every such right or remedy shall be cumulative and
concurrent, and in addition to every other such right or remedy, and may be pursued singly,
concurrently, successively or otherwise, at the sole discretion of the Purchaser; and shall not be
exhausted by any one exercise thereof but may be exercised as often as occasion therefor shall
occur.




          (b) The Company hereby waives presentment, demand, notice of nonpayment, protest, notice of
protest, notice of dishonor and any and all other notices in connection with any default in the
payment of, or any enforcement of the payment of, all amounts due under this Note. With respect to
any final, nonappealable order, judgment or decree of a court of






 4.









 







competent jurisdiction, to the extent permitted by law, the Company waives the right to any
stay of execution and the benefit of all exemption laws now or hereafter in effect.




     10. Warrants. Upon any conversion of this Note pursuant to Sections 4(b), 4(c) or 5
above, or, in the absence of such conversion, at the Maturity Date, the Company shall issue to the
Purchaser a Warrant substantially in the form attached hereto as Exhibit A in accordance
with Section 1.4 of the Purchase Agreement.



     11. Pari Passu Notes. By accepting this Note, the Purchaser acknowledges and agrees that the
right of payment of all or any portion of the outstanding principal amounts of each of the Notes
and all interest thereon shall be pari passu in right of payment and in all other respects to all
of the other Notes. In the event the Purchaser receives payments in excess of its pro rata share
of the Company’s payments to all of the Purchasers in respect of the Notes, then such Purchaser
shall hold in trust all such excess payments for the benefit of the other Purchasers and shall pay
such amounts held in trust to such other Purchasers upon demand by such Purchasers.



     12. Waiver by Holder. No waiver of any obligation of the Company under this Note shall be
effective unless it is in a writing signed by the holder hereof. A waiver by the holder hereof of
any right or remedy under this Note on any occasion shall not be a bar to exercise of the same
right or remedy on any subsequent occasion or of any other right or remedy at any time.



     13. Notice. Any notice required or permitted under this Note shall be in writing and shall be
deemed to have been given on the date of delivery, if personally delivered to the party to whom
notice is to be given, or on the fifth (5th) business day after mailing, if mailed to
the party to whom notice is to be given, by certified mail, return receipt requested, postage
prepaid, and addressed as follows:



     if to the Company, at


NuPathe Inc.

227 Washington Street, Suite 200

Conshohocken, PA 19428

Attention:   Chief Executive Officer

Telephone: (484) 567-0130

Facsimile:  (484) 567-01362




     with a copy to,


Morgan Lewis & Bockius LLP

1701 Market Street

Philadelphia, PA 19103

Attention:   Michael N. Peterson

Telephone: (215) 963-5025

Facsimile:  (215) 963-5001

Email:         mpeterson@morganlewis.com









 5.









 










and, if to the holder, at the most recent address provided to the Company by the holder for such
purpose; or, in each case, to the most recent address, specified by written notice, given to the
sender pursuant to this paragraph.




     14. Assignment. This Note will be registered on the books of the Company or its agent as to
principal and interest. The Purchaser may assign or otherwise transfer this Note to any affiliate
of such Purchaser that is an “accredited investor” without the prior written consent of the
Company; provided that (i) any such transferee agrees to be subject to the terms of the Amended and
Restated Investor Rights Agreement, dated as of July 8, 2008, by and among the Company and the
other parties named therein (the “Investor Rights Agreement”) to the same extent as if such
transferee was an original Holder (as defined in the Investor Rights Agreement) with respect to
any Registrable Securities (as defined in the Investor Rights Agreement) that may be issued to such
transferee and (ii) any transfer of this Note will be effected only by surrender of this Note to
the Company and reissuance of a new note to the transferee. Any other assignment or transfer of
this Note by the Purchaser shall require the prior written consent of the Company.



     15. Severability. In the event any one or more of the provisions of this Note shall for any
reason be held to be invalid, illegal or unenforceable, in whole or in part or in any respect, or
in the event that any one or more of the provisions of this Note operate or would prospectively
operate to invalidate this Note, then and in any such event, such provision(s) only shall be deemed
null and void and shall not affect any other provision of this Note and the remaining provisions of
this Note shall remain operative and in full force and effect and in no way shall be affected,
prejudiced, or disturbed thereby.



     16. Governing Law. This Note shall be governed by and construed and enforced in accordance
with the laws of the State of Delaware without regard to the application of the principles of
conflicts of law of any jurisdiction.



     17. Attorneys’ Fees. In the event of any Event of Default hereunder pursuant to which the
Majority Holders elect to accelerate this Note, the Company shall pay all reasonable attorneys’
fees and court costs incurred by the Purchaser in enforcing and collecting this Note.



     18. Amendment. Except as otherwise provided in this Note, no modification or amendment hereof
shall be effective unless (i) made in a writing signed by appropriate officers of the Company,
(ii) such amendment or modification is approved by the Majority Holders, (iii) such amendment or
modification is made to all of the Notes issued pursuant to the Purchase Agreement, and (iv) such
amendment or modification is made in accordance with the terms of the Subordination Agreement.



     19. Reservation of Securities. The Company shall take all necessary actions to reserve and
keep available out of its authorized capital stock, solely for the purpose of issuance upon
conversion of this Note, such number and kind of shares of capital stock as may then be issuable
upon the direct and indirect conversion of all amounts owing under this Note. The Company
covenants that all shares of capital stock which shall be so issuable will, upon the conversion of
this Note as herein provided, be duly and validly issued and fully paid and nonassessable by the
Company.



 6.









 





     20. Waiver of Jury Trial. The Company irrevocably waives any and all rights the Company may
have to a trial by jury in any action, proceeding or claim arising from or relating to this Note,
any documents executed in connection with this Note or any transaction contemplated by this Note or
such documents. The Company acknowledges that the foregoing waiver is knowing and voluntary.



     21. Stockholders, Officers and Directors Not Liable. In no event shall any stockholder,
officer or director of the Company be liable for any amounts due or payable pursuant to this Note.



[Signature Page Follows]






 7.









 








     This Secured Subordinated Convertible Promissory Note has been executed and delivered
as of the Issue Date by the undersigned as duly authorized representative of the Company.



	 	 	 	 	 
	 	NuPathe Inc.

 	 
	 	By:  	 	 
	 	 	Name:  	Jane H. Hollingsworth 	 
	 	 	Title:  	Chief Executive Officer 	 
	 



[Signature Page to NuPathe Inc. Secured Subordinated Convertible Promissory Note]









 









 








Exhibit A




Form of Warrant



(Please see attached)



[Exhibit A to NuPathe Inc. Secured Subordinated Convertible Promissory Note]





 











 





EXHIBIT C




FORM OF WARRANT




 









 







THE SECURITIES REPRESENTED BY THIS WARRANT HAVE BEEN ACQUIRED FOR INVESTMENT, HAVE NOT BEEN
REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR UNDER ANY STATE OR FEDERAL SECURITIES
LAWS AND MAY NOT BE SOLD, TRANSFERRED, OR ASSIGNED EXCEPT: (1) PURSUANT TO THE EFFECTIVE
REGISTRATION THEREOF UNDER SUCH ACT; OR (2) IF, IN THE OPINION OF COUNSEL FOR THE REGISTERED OWNER
HEREOF, WHICH OPINION IS REASONABLY SATISFACTORY TO THE COMPANY, THE PROPOSED SALE, TRANSFER OR
ASSIGNMENT MAY BE EFFECTED WITHOUT SUCH REGISTRATION AND WILL NOT BE IN VIOLATION OF APPLICABLE
STATE AND/OR FEDERAL SECURITIES LAWS




NUPATHE INC.

WARRANT TO PURCHASE SHARES

OF PREFERRED STOCK




			
	 	 	 
	Warrant No.                     
	 	Issue Date:                           , 20          






     THIS CERTIFIES THAT, for value received,                      (“Holder”), is entitled to subscribe for
and purchase up to                      shares of                                          (as applicable, the “Shares”) of
NuPathe Inc., a Delaware corporation (the “Company”), at the Warrant Price (as defined
below), subject to the provisions and upon the terms and conditions set forth herein. As used
herein, “Note” shall mean that certain Secured Subordinated Convertible Promissory Note, dated as
of April                     , 2010, made by the Company in favor of the Holder. This Warrant is one of a series
of Warrants to purchase Shares of Preferred Stock issued by the Company pursuant to that certain
Subordinated Convertible Note and Warrant Purchase Agreement, dated as of April                     , 2010, by and
among the Company, the Holder and the other parties named therein (as the same may be amended from
time to time, the “Purchase Agreement”). Terms used, but not otherwise defined herein, shall have
the meanings ascribed to such terms in the Purchase Agreement.



     1. Warrant Price. The per share exercise price (the “Warrant Price”)
initially shall be equal to $                     per share as set forth in the Note. The Warrant Price shall
be subject to adjustment as provided in Section 6 below.



     2. Conditions to Exercise. The purchase right represented by this Warrant
may be exercised at any time, or from time to time, in whole or in part, during the term commencing
on the date hereof and ending on the earlier to occur of (i) the seventh (7th)
anniversary of such date and (ii) the consummation of an IPO (as defined in the Note).



     3. Method of Exercise; Payment; Issuance of Shares.



          (a) Cash Exercise. Subject to Section 2 hereof, the purchase right
represented by this Warrant may be exercised by the Holder hereof, in whole or in part, by the
surrender of this Warrant (with a duly executed Notice of Exercise in the form attached hereto) at
the principal office of the Company (as set forth in Section 11 below) and by payment to the
Company, by cashier’s or other check acceptable to the Company representing immediately available
funds, of an amount equal to the then applicable Warrant Price multiplied by the number of Shares
then being purchased. In the event of any exercise of the rights represented by this Warrant,
certificates for the Shares so purchased shall be in the name of, and delivered to, the Holder
hereof, or as such Holder may direct (subject to the terms of transfer contained herein and upon
payment by such Holder hereof of any applicable transfer taxes).




 








 




          (b) Net Issue Exercise. If the Fair Market Value of one Share is greater
than the Warrant Price (at the date of such calculation), then in lieu of exercising this Warrant
pursuant to Section 3(a), the Holder may elect to receive Shares equal to the value of this Warrant
(or of any portion thereof remaining unexercised) by surrender of this Warrant at the principal
office of the Company together with notice of such election, in which event the Company shall issue
to Holder the number of Shares computed using the following formula:









	 	 	 	 	 

	Where X

	 	=
	 	the number of Shares to be issued to Holder.
	Y

	 	=
	 	the number of Shares purchasable under this Warrant (at the date of such calculation).
	A

	 	=
	 	the Fair Market Value of one Share issuable under this Warrant (at the date of such calculation).
	B

	 	=
	 	Warrant Price (as adjusted to the date of such calculation).






          (c) Fair Market Value. For purposes of this Section 3, “Fair Market Value”
of one Share issuable under this Warrant shall mean: the fair market value of such security
determined by a third party appraiser designated by a majority of the members of the Company’s
Board of Directors (the “Board”) who are not affiliated with any Purchaser (the “Independent
Directors”) and reasonably acceptable to the Requisite Holders (the “Appraiser”); provided,
however, that if the parties fail to agree on an Appraiser, then the Independent Directors, on the
one hand, and the Majority Holders (as defined in the Note), on the other hand, shall each select
its own independent appraiser, which appraisers shall then select an independent appraiser to
finally determine the Fair Market Value. If either the Independent Directors, on the one hand, or
the Majority Holders, on the other hand, fails to select an independent appraiser, then the
successfully selected independent appraiser shall finally determine the Fair Market Value. The
Company shall bear all fees and expenses in connection with the selection and engagement of the
Appraiser




     4. Legends. Each certificate representing the Shares shall be endorsed
with the following legend:




“THE SECURITIES REPRESENTED HEREBY HAVE NOT BEEN REGISTERED UNDER
THE SECURITIES ACT OF 1933 (THE “ACT”), AND MAY NOT BE OFFERED, SOLD
OR OTHERWISE TRANSFERRED, ASSIGNED, PLEDGED OR HYPOTHECATED UNLESS
AND UNTIL REGISTERED UNDER THE ACT OR UNLESS THE COMPANY HAS
RECEIVED AN OPINION OF COUNSEL OR OTHER EVIDENCE SATISFACTORY TO THE
COMPANY AND ITS COUNSEL THAT SUCH REGISTRATION IS NOT REQUIRED.”



     The Company need not enter into its stock register a transfer of Shares unless the conditions
specified in the foregoing legend are satisfied. The Company may also instruct its transfer agent
not to register the transfer of any of the Shares unless the conditions specified in the foregoing
legend are satisfied.



-2-









 





     5. Stock Fully Paid; Reservation of Shares. All Shares that may be issued
upon the exercise of the rights represented by this Warrant, will, upon issuance, be fully paid and
nonassessable, and free from all taxes, liens, and charges with respect to the issue thereof.
During the period within which the rights represented by this Warrant may be exercised, the Company
will at all times have authorized, and reserved for issuance upon exercise of the purchase rights
evidenced by this Warrant, a sufficient number of Shares to provide for the exercise of the rights
represented by this Warrant.



     6. Adjustment for Certain Events. In the event of changes in the
outstanding Shares (or the Company’s Common Stock in the event the Shares have been converted into
Common Stock) by reason of stock dividends, split-ups, recapitalizations, reclassifications,
mergers, consolidations, combinations or exchanges of shares, separations, reorganizations,
liquidations, or the like, the number and class of shares available for purchase pursuant to this
Warrant in the aggregate and the Warrant Price shall be correspondingly adjusted, as appropriate,
by the Board. The adjustment shall be such as will give the Holder of this Warrant upon exercise
for the same aggregate Warrant Price the total number, class and kind of shares as he would have
owned had the Warrant been exercised prior to the event and had he continued to hold such shares
until after the event requiring adjustment.



     7. Notice of Adjustments. Whenever any Warrant Price shall be adjusted
pursuant to Section 6 hereof, the Company shall prepare a certificate signed by the Company’s chief
executive officer setting forth, in reasonable detail, the event requiring the adjustment, the
amount of the adjustment, the method by which such adjustment was calculated, and the Warrant Price
and number of Shares issuable upon exercise of the Warrant after giving effect to such adjustment,
and shall cause copies of such certificate to be mailed (by certified or registered mail, return
receipt required, postage prepaid) within thirty (30) days of such adjustment to the Holder of this
Warrant as set forth in Section 11 hereof.



     8. No Fractional Shares. No fractional Shares will be issued in connection
with any exercise hereunder, but in lieu of such fractional share the Company shall make a cash
payment therefore upon the basis of the Warrant Price then in effect.



     9. Charges, Taxes and Expenses. Issuance of certificates for Shares upon
the exercise of this Warrant shall be made without charge to the Holder for any United States or
state of the United States documentary stamp tax or other incidental expense within respect to the
issuance of such certificate, all of which taxes and expenses shall be paid by the Company, and
such certificates shall be issued in the name of the Holder.



     10. Miscellaneous.



          (a) Successors. This Warrant shall be binding upon any successors or
assigns of the Company.




          (b) Assignment. The Holder may assign or otherwise transfer this Warrant to
any affiliate of such Holder that is an “accredited investor” without the prior written consent of
the Company; provided that (i) any such transferee agrees to be subject to the terms of the
Amended and Restated Investor Rights Agreement, dated as of July 8, 2008, by and among the Company
and the other parties named therein (the “Investor Rights Agreement”) to the same extent as if such
transferee was an original Holder (as defined in the Investor Rights Agreement) with respect to any
Registrable Securities (as defined in the Investor Rights Agreement) that may be issued to such
transferee and (ii) any transfer of this Warrant will be effected only by surrender of this
Warrant to the Company and reissuance of a new warrant to the transferee. Any other assignment or
transfer of this Warrant by the Holder shall require the prior written consent of the Company.




-3-









 





          (c) Amendment. Except as otherwise provided in this Warrant, no
modification or amendment hereof shall be effective unless (i) made in a writing signed by
appropriate officers of the Company, (ii) such amendment or modification is approved by the
Majority Holders (as defined in the Note), and (iii) such amendment or modification is made to all
of the Warrants issued pursuant to the Purchase Agreement.




          (d) Governing Law. This Warrant shall be governed by, and construed and
enforced in accordance with, the substantive laws of the State of Delaware, without regard to the
conflicts of laws principles of any jurisdiction.




          (e) Headings. The headings used in this Warrant are used for convenience
only and are not to be considered in construing or interpreting this Warrant.




          (f) Saturdays, Sundays, Holidays. If the last or appointed day for the
taking of any action or the expiration of any right required or granted herein shall be a Saturday
or a Sunday or shall be a legal holiday in the State of Delaware, then such action may be taken or
such right may be exercised on the next succeeding day not a legal holiday




          (g) No Rights as Stockholder. Prior to the exercise of this Warrant, the
Holder shall not be entitled to any rights of a stockholder of the Company with respect to shares
for which this Warrant shall be exercisable, including, without limitation, the right to vote, to
receive dividends or other distributions (other than as expressly provided for in this Warrant) or
to exercise any preemptive rights, and shall not be entitled to receive any notice of any
proceedings of the Company




          (h) Compliance with Securities Laws. The Holder, by acceptance hereof,
acknowledges that this Warrant and the Shares to be issued upon exercise hereof are being acquired
solely for the Holder’s own account and not as a nominee for any other party, and for investment,
and that the Holder will not offer, sell or otherwise dispose of this Warrant or any Shares to be
issued upon exercise hereof except under circumstances that will not result in a violation of
applicable federal and state securities laws.




     11. Notices. Any notice required or permitted hereunder shall be in writing
and shall be mailed by overnight courier, registered or certified mail, return receipt required,
and postage pre-paid, or otherwise delivered by hand or by messenger, addressed as set forth below,
or at such other address as the Company or the Holder hereof shall have furnished to the other
party.


     If to the Company:




NuPathe Inc.

227 Washington Street, Suite 200

Conshohocken, PA 19428

Attention: Chief Executive Officer

Telephone: (484) 567-0130

Facsimile: (484) 567-01362



with a copy to:



Morgan Lewis & Bockius LLP

1701 Market Street

Philadelphia, PA 19103

Attention: Michael N. Peterson

Telephone: (215) 963-5025



-4-









 





Facsimile: (215) 963-5001

Email: mpeterson@morganlewis.com



and, if to the Holder, at the most recent address provided to the Company by the Holder for
such purpose; or, in each case, to the most recent address, specified by written notice, given to
the sender pursuant to this paragraph.




[Signature Page Follows]




-5-









 





     IN WITNESS WHEREOF, NuPathe Inc. has caused this Warrant to Purchase Shares of Preferred
Stock to be executed by its officers thereunto duly authorized.



Dated as of this       day of                     , 20     .




	 	 	 	 	 
	 	NuPathe Inc.

 	 
	 	By:  	 	 
	 	Name:  	 	 
	 	Title:  	 	 
	 




 









 








NOTICE OF EXERCISE





			
	TO:	 	NuPathe Inc.

227 Washington Street, Suite 200

Conshohocken, PA 19428

Attention: Chief Executive Officer






     The undersigned,                                          (“Holder”) elects to acquire shares of
                                        
of NuPathe Inc. (the “Company”), pursuant to the terms of the Warrant to Purchase Shares of
Preferred Stock dated                                          (the “Warrant”).



     The Holder exercises its rights under the Warrant as set forth below:



     1. The Holder elects to purchase                     shares of the Company’s
                                         and tenders herewith a check in the amount of $                     as payment of
the purchase price.



     2. The Holder surrenders the Warrant with this Notice of Exercise.



     3. The Holder represents that it is acquiring the aforesaid shares of
                                         for investment and not with a view to or for resale in connection with,
distribution and that the Holder has no present intention of distributing or reselling the shares.



     Please issue a certificate representing the shares of                                          in the name of the
Holder or in such other name as is specified below:




			
	Name:	 	 







			
	Address:	 	 







			
	Taxpayer I.D.	 	 





By:





			
	Name:	 	 







			
	Title:	 	 







			
	Date:	 	 







 











 





EXHIBIT D




KNOWLEDGE PERSONS


Each of Jane Hollingsworth, Terri Sebree, Suzanne Hanlon and Keith Goldan.










 









 









EXHIBITS E-1 AND E-2




CAPITALIZATION



 











 







     



					
	Capitalization by Owner Report-Actual

NuPathe, Inc.

Period End: 3/31/2010 

Grouped
by Participant Type
	 	Exhibit E-1
	 	 






	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	Financing Rounds	 	 	 	Outstanding Shares by Plan	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	NuPathe Inc	 	 	 	 	 	 	Outside of	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	Common	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	2005 Equity	 	 	 	 	 	 	Option Plan-	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	Stock- RSA,	 	 	Common Stock-	 	 	 	 	 	 	 	 	 	 	 	Compensation	 	 	Outside of ’05	 	 	Series B	 	 	Outstanding	 	 	 	 	 	 	 	 
	Participant Name	 	 	Common Stock	 	 	unvested	 	 	total	 	 	Series A	 	 	Series B	 	 	 	Plan	 	 	Equity Plan	 	 	warrants	 	 	Total	 	 	 	Total	 	 	%	 
	Ben Franklin Technology Partners of SE Pa
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	374,268	 	 	 	516,129	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	890,397	 	 	 	1.36	%
	Biotechnology Greenhouse Corp of SE Pa
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	988,261	 	 	 	268,817	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	1,257,078	 	 	 	1.92	%
	Climax, John
	 	 	 	50,000	 	 	 	 	 	 	 	50,000	 	 	 	987,724	 	 	 	537,634	 	 	 	 	15,000	 	 	 	 	 	 	 	 	 	 	 	15,000	 	 	 	 	1,590,358	 	 	 	2.43	%
	Coulaloglou, Michele
	 	 	 	1,250	 	 	 	 	 	 	 	1,250	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	1,250	 	 	 	0.00	%
	Dillon, John
	 	 	 	50,000	 	 	 	 	 	 	 	50,000	 	 	 	 	 	 	 	 	 	 	 	 	90,000	 	 	 	 	 	 	 	 	 	 	 	90,000	 	 	 	 	140,000	 	 	 	0.21	%
	Felker, Ezra
	 	 	 	45,000	 	 	 	15,000	 	 	 	60,000	 	 	 	 	 	 	 	 	 	 	 	 	615,289	 	 	 	 	 	 	 	 	 	 	 	615,289	 	 	 	 	675,289	 	 	 	1.03	%
	Felker, Ezra H., IRA
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	 	 	 	48,387	 	 	 	 	 	 	 	 	 	 	 	 	1,128	 	 	 	1,128	 	 	 	 	49,515	 	 	 	0.08	%
	Goldan, Keith
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	 	 	 	26,882	 	 	 	 	799,122	 	 	 	 	 	 	 	 	 	 	 	799,122	 	 	 	 	826,004	 	 	 	1.26	%
	Hanlon, Suzanne
	 	 	 	135,000	 	 	 	5,000	 	 	 	140,000	 	 	 	 	 	 	 	26,882	 	 	 	 	298,038	 	 	 	 	 	 	 	627	 	 	 	298,665	 	 	 	 	465,547	 	 	 	0.71	%
	Hollingsworth, Bradford Irrevocable Trust
	 	 	 	50,000	 	 	 	 	 	 	 	50,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	50,000	 	 	 	0.08	%
	Hollingsworth, Jane
	 	 	 	1,225,000	 	 	 	25,000	 	 	 	1,250,000	 	 	 	143,668	 	 	 	53,763	 	 	 	 	2,046,877	 	 	 	 	 	 	 	1,253	 	 	 	2,048,130	 	 	 	 	3,495,561	 	 	 	5.34	%
	Hollingsworth, Jane Irrevocable Trust
	 	 	 	50,000	 	 	 	 	 	 	 	50,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	50,000	 	 	 	0.08	%
	O’Neill, Carol
	 	 	 	118,750	 	 	 	1,250	 	 	 	120,000	 	 	 	 	 	 	 	 	 	 	 	 	154,000	 	 	 	 	 	 	 	 	 	 	 	154,000	 	 	 	 	274,000	 	 	 	0.42	%
	Pierce, Mark
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	 	 	 	107,527	 	 	 	 	351,645	 	 	 	 	 	 	 	2,506	 	 	 	354,151	 	 	 	 	461,678	 	 	 	0.71	%
	Sebree, Terri
	 	 	 	1,325,000	 	 	 	25,000	 	 	 	1,350,000	 	 	 	 	 	 	 	 	 	 	 	 	1,214,086	 	 	 	 	 	 	 	 	 	 	 	1,214,086	 	 	 	 	2,564,086	 	 	 	3.92	%
	Jackson, David
	 	 	 	10,000	 	 	 	 	 	 	 	10,000	 	 	 	 	 	 	 	 	 	 	 	 	10,000	 	 	 	 	 	 	 	 	 	 	 	10,000	 	 	 	 	20,000	 	 	 	0.03	%
	Battelle Ventures L.P.
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	2,274,194	 	 	 	3,387,097	 	 	 	 	 	 	 	 	 	 	 	 	67,670	 	 	 	67,670	 	 	 	 	5,728,961	 	 	 	8.75	%
	BioAdvance Ventures, L.P.
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	1,792,115	 	 	 	1,433,692	 	 	 	 	 	 	 	 	 	 	 	 	25,063	 	 	 	25,063	 	 	 	 	3,250,870	 	 	 	4.97	%
	Birchmere Ventures III L.P.
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	2,293,907	 	 	 	1,949,820	 	 	 	 	 	 	 	 	 	 	 	 	34,754	 	 	 	34,754	 	 	 	 	4,278,481	 	 	 	6.54	%
	Birchmere Ventures III TSIB, L.P.
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	1,290,323	 	 	 	1,096,775	 	 	 	 	 	 	 	 	 	 	 	 	19,549	 	 	 	19,549	 	 	 	 	2,406,647	 	 	 	3.68	%
	Innovation Valley Partners, L.P.
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	413,978	 	 	 	376,344	 	 	 	 	 	 	 	 	 	 	 	 	7,519	 	 	 	7,519	 	 	 	 	797,841	 	 	 	1.22	%
	Lambe, Ronan
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	987,724	 	 	 	537,634	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	1,525,358	 	 	 	2.33	%
	Quaker Bio Ventures II
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	 	 	 	12,903,226	 	 	 	 	 	 	 	 	 	 	 	 	300,754	 	 	 	300,754	 	 	 	 	13,203,980	 	 	 	20.17	%
	Safeguard Delaware Inc
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	5,376,344	 	 	 	7,526,881	 	 	 	 	 	 	 	 	 	 	 	 	150,377	 	 	 	150,377	 	 	 	 	13,053,602	 	 	 	19.94	%
	SR One Ltd.
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	 	 	 	5,376,344	 	 	 	 	 	 	 	 	 	 	 	 	125,314	 	 	 	125,314	 	 	 	 	5,501,658	 	 	 	8.40	%
	Angelov. Angel
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	215,000	 	 	 	 	 	 	 	 	 	 	 	215,000	 	 	 	 	215,000	 	 	 	0.33	%
	Arnold, Susan
	 	 	 	12,655	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	14,917	 	 	 	 	 	 	 	 	 	 	 	14,917	 	 	 	 	14,917	 	 	 	0.02	%
	Barb, Tracey
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	34,464	 	 	 	 	 	 	 	 	 	 	 	34,464	 	 	 	 	34,464	 	 	 	0.05	%
	Beg, Jamil
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	10,000	 	 	 	 	 	 	 	 	 	 	 	10,000	 	 	 	 	10,000	 	 	 	0.02	%
	Brown, Charles G.
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	48,000	 	 	 	 	 	 	 	 	 	 	 	48,000	 	 	 	 	48,000	 	 	 	0.07	%
	Cardillo, Marco
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	5,000	 	 	 	 	 	 	 	 	 	 	 	5,000	 	 	 	 	5,000	 	 	 	0.01	%
	Cassidy, L. Wayne
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	25,000	 	 	 	 	 	 	 	 	 	 	 	25,000	 	 	 	 	25,000	 	 	 	0.04	%
	Chandler-Skerkis, Amy
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	30,000	 	 	 	 	 	 	 	 	 	 	 	30,000	 	 	 	 	30,000	 	 	 	0.05	%
	Cola, Michael
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	265,000	 	 	 	 	 	 	 	 	 	 	 	265,000	 	 	 	 	265,000	 	 	 	0.40	%
	Curtin, Theresa
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	36,164	 	 	 	 	 	 	 	 	 	 	 	36,164	 	 	 	 	36,164	 	 	 	0.06	%
	Higgins, Donna
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	35,000	 	 	 	 	 	 	 	 	 	 	 	35,000	 	 	 	 	35,000	 	 	 	0.05	%
	Jones, Mary
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	31,964	 	 	 	 	 	 	 	 	 	 	 	31,964	 	 	 	 	31,964	 	 	 	0.05	%
	Klos, Monica
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	145,858	 	 	 	 	 	 	 	 	 	 	 	145,858	 	 	 	 	145,858	 	 	 	0.22	%
	Kolbush-Jackson, Donna
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	35,464	 	 	 	 	 	 	 	 	 	 	 	35,464	 	 	 	 	35,464	 	 	 	0.05	%
	Logan, Honora
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	10,000	 	 	 	 	 	 	 	 	 	 	 	10,000	 	 	 	 	10,000	 	 	 	0.02	%
	McLaughlin, Gerald
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	687,289	 	 	 	 	 	 	 	 	 	 	 	687,289	 	 	 	 	687,289	 	 	 	1.05	%
	Milan, Pola
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	15,786	 	 	 	 	 	 	 	 	 	 	 	15,786	 	 	 	 	15,786	 	 	 	0.02	%
	Nett, Erica L._assignee of Robert Nett
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	72,000	 	 	 	 	 	 	 	 	 	 	 	72,000	 	 	 	 	72,000	 	 	 	0.11	%
	Nett, Nicholas E._assignee of Robert Nett
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	72,000	 	 	 	 	 	 	 	 	 	 	 	72,000	 	 	 	 	72,000	 	 	 	0.11	%
	Richardson, Lauren
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	25,572	 	 	 	 	 	 	 	 	 	 	 	25,572	 	 	 	 	25,572	 	 	 	0.04	%
	Siegel, Steven
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	20,000	 	 	 	 	 	 	 	 	 	 	 	20,000	 	 	 	 	20,000	 	 	 	0.03	%
	Stiles, Deborah
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	5,000	 	 	 	 	 	 	 	 	 	 	 	5,000	 	 	 	 	5,000	 	 	 	0.01	%
	Sussman, Joel
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	26,457	 	 	 	 	 	 	 	 	 	 	 	26,457	 	 	 	 	26,457	 	 	 	0.04	%
	Whetstone, Robert
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	75,000	 	 	 	 	 	 	 	 	 	 	 	75,000	 	 	 	 	75,000	 	 	 	0.11	%
	Oxford Finance Corp
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	134,408	 	 	 	 	 	 	 	134,408	 	 	 	 	134,408	 	 	 	0.21	%
	Outstanding Shares Pool
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	 	 	 	 	 	 	 	 	831,103	 	 	 	 	 	 	 	 	 	 	 	831,103	 	 	 	 	831,103	 	 	 	1.27	%
	Totals
	 	 	 	3,072,655	 	 	 	71,250	 	 	 	3,131,250	 	 	 	16,922,506	 	 	 	36,173,834	 	 	 	 	8,366,095	 	 	 	134,408	 	 	 	736,514	 	 	 	9,237,017	 	 	 	 	65,464,607	 	 	 	100.00	%








 








 







					
	 	 	 	 	 
	Capitalization by Owner Report- PROFORMA , POST DEBT CONVERSION

NuPathe, Inc.

Period End: 3/31/2010

Grouped by Participant Type
	 	Exhibit E-2

Assumptions: (1) notes convert on 9/30/2010 and (2) notes convert at 80% of the Series B price of $0.93/share ($0.74/share)

	 	 
	 	 	 	 	 






	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	Financing Rounds	 	 	 	 	 	 	 	Outstanding Shares by Plan	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	 	 	 	 	NuPathe Inc	 	 	 	 	 	 	Outside of	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	Common	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	2005 Equity	 	 	 	 	 	 	Option Plan-	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	Stock- RSA,	 	 	Common Stock-	 	 	 	 	 	 	 	 	 	 	PROFORMA	 	 	 	Compensation	 	 	Outside of ’05	 	 	Series B	 	 	PROFORMA	 	 	Outstanding	 	 	 	PROFORMA	 	 	 	 
	Participant Name	 	 	Common Stock	 	 	unvested	 	 	total	 	 	Series A	 	 	Series B	 	 	Series B-2	 	 	 	Plan	 	 	Equity Plan	 	 	warrants	 	 	Warrants	 	 	Total	 	 	 	Total	 	 	%	 
	Ben Franklin Technology Partners of SE Pa
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	374,268	 	 	 	516,129	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	890,397	 	 	 	1.07	%
	Biotechnology Greenhouse Corp of SE Pa
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	988,261	 	 	 	268,817	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	1,257,078	 	 	 	1.51	%
	Climax, John
	 	 	 	50,000	 	 	 	 	 	 	 	50,000	 	 	 	987,724	 	 	 	537,634	 	 	 	 	 	 	 	 	15,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	15,000	 	 	 	 	1,590,358	 	 	 	1.92	%
	Coulaloglou, Michele
	 	 	 	1,250	 	 	 	 	 	 	 	1,250	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	1,250	 	 	 	0.00	%
	Dillon, John
	 	 	 	50,000	 	 	 	 	 	 	 	50,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	90,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	90,000	 	 	 	 	140,000	 	 	 	0.17	%
	Felker, Ezra
	 	 	 	45,000	 	 	 	15,000	 	 	 	60,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	615,289	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	615,289	 	 	 	 	675,289	 	 	 	0.81	%
	Felker, Ezra H., IRA
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	 	 	 	48,387	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	1,128	 	 	 	 	 	 	 	1,128	 	 	 	 	49,515	 	 	 	0.06	%
	Goldan, Keith
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	 	 	 	26,882	 	 	 	10,526	 	 	 	 	799,122	 	 	 	 	 	 	 	 	 	 	 	2,534	 	 	 	801,656	 	 	 	 	839,064	 	 	 	1.01	%
	Hanlon, Suzanne
	 	 	 	135,000	 	 	 	5,000	 	 	 	140,000	 	 	 	 	 	 	 	26,882	 	 	 	7,018	 	 	 	 	298,038	 	 	 	 	 	 	 	627	 	 	 	1,689	 	 	 	300,354	 	 	 	 	474,254	 	 	 	0.57	%
	Hollingsworth, Bradford Irrevocable Trust
	 	 	 	50,000	 	 	 	 	 	 	 	50,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	50,000	 	 	 	0.06	%
	Hollingsworth, Jane
	 	 	 	1,225,000	 	 	 	25,000	 	 	 	1,250,000	 	 	 	143,668	 	 	 	53,763	 	 	 	70,176	 	 	 	 	2,046,877	 	 	 	 	 	 	 	1,253	 	 	 	16,892	 	 	 	2,065,022	 	 	 	 	3,582,629	 	 	 	4.32	%
	Hollingsworth, Jane Irrevocable Trust
	 	 	 	50,000	 	 	 	 	 	 	 	50,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	50,000	 	 	 	0.06	%
	O’Neill, Carol
	 	 	 	118,750	 	 	 	1,250	 	 	 	120,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	154,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	154,000	 	 	 	 	274,000	 	 	 	0.33	%
	Pierce, Mark
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	 	 	 	107,527	 	 	 	 	 	 	 	 	351,645	 	 	 	 	 	 	 	2,506	 	 	 	 	 	 	 	354,151	 	 	 	 	461,678	 	 	 	0.56	%
	Sebree, Terri
	 	 	 	1,325,000	 	 	 	25,000	 	 	 	1,350,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	1,214,086	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	1,214,086	 	 	 	 	2,564,086	 	 	 	3.09	%
	Jackson, David
	 	 	 	10,000	 	 	 	 	 	 	 	10,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	10,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	10,000	 	 	 	 	20,000	 	 	 	0.02	%
	Battelle Ventures L.P.
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	2,274,194	 	 	 	3,387,097	 	 	 	1,716,003	 	 	 	 	 	 	 	 	 	 	 	 	67,670	 	 	 	413,055	 	 	 	480,725	 	 	 	 	7,858,019	 	 	 	9.47	%
	BioAdvance Ventures, L.P.
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	1,792,115	 	 	 	1,433,692	 	 	 	—	 	 	 	 	 	 	 	 	 	 	 	 	25,063	 	 	 	—	 	 	 	25,063	 	 	 	 	3,250,870	 	 	 	3.92	%
	Birchmere Ventures III L.P.
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	2,293,907	 	 	 	1,949,820	 	 	 	1,254,165	 	 	 	 	 	 	 	 	 	 	 	 	34,754	 	 	 	301,887	 	 	 	336,641	 	 	 	 	5,834,533	 	 	 	7.03	%
	Birchmere Ventures III TSIB, L.P.
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	1,290,323	 	 	 	1,096,775	 	 	 	705,468	 	 	 	 	 	 	 	 	 	 	 	 	19,549	 	 	 	169,811	 	 	 	189,360	 	 	 	 	3,281,927	 	 	 	3.95	%
	Innovation Valley Partners, L.P.
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	413,978	 	 	 	376,344	 	 	 	190,667	 	 	 	 	 	 	 	 	 	 	 	 	7,519	 	 	 	45,895	 	 	 	53,414	 	 	 	 	1,034,403	 	 	 	1.25	%
	Lambe, Ronan
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	987,724	 	 	 	537,634	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	1,525,358	 	 	 	1.84	%
	Quaker Bio Ventures II
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	 	 	 	12,903,226	 	 	 	4,766,672	 	 	 	 	 	 	 	 	 	 	 	 	300,754	 	 	 	1,147,374	 	 	 	1,448,128	 	 	 	 	19,118,026	 	 	 	23.04	%
	Safeguard Delaware Inc
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	5,376,344	 	 	 	7,526,881	 	 	 	3,813,338	 	 	 	 	 	 	 	 	 	 	 	 	150,377	 	 	 	917,899	 	 	 	1,068,276	 	 	 	 	17,784,839	 	 	 	21.43	%
	SR One Ltd.
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	 	 	 	5,376,344	 	 	 	1,588,890	 	 	 	 	 	 	 	 	 	 	 	 	125,314	 	 	 	382,458	 	 	 	507,772	 	 	 	 	7,473,006	 	 	 	9.01	%
	Angelov. Angel
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	215,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	215,000	 	 	 	 	215,000	 	 	 	0.26	%
	Arnold, Susan
	 	 	 	12,655	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	14,917	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	14,917	 	 	 	 	14,917	 	 	 	0.02	%
	Barb, Tracey
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	34,464	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	34,464	 	 	 	 	34,464	 	 	 	0.04	%
	Beg, Jamil
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	10,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	10,000	 	 	 	 	10,000	 	 	 	0.01	%
	Brown, Charles G.
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	48,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	48,000	 	 	 	 	48,000	 	 	 	0.06	%
	Cardillo, Marco
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	5,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	5,000	 	 	 	 	5,000	 	 	 	0.01	%
	Cassidy, L. Wayne
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	25,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	25,000	 	 	 	 	25,000	 	 	 	0.03	%
	Chandler-Skerkis, Amy
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	30,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	30,000	 	 	 	 	30,000	 	 	 	0.04	%
	Cola, Michael
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	265,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	265,000	 	 	 	 	265,000	 	 	 	0.32	%
	Curtin, Theresa
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	36,164	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	36,164	 	 	 	 	36,164	 	 	 	0.04	%
	Higgins, Donna
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	35,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	35,000	 	 	 	 	35,000	 	 	 	0.04	%
	Jones, Mary
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	31,964	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	31,964	 	 	 	 	31,964	 	 	 	0.04	%
	Klos, Monica
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	145,858	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	145,858	 	 	 	 	145,858	 	 	 	0.18	%
	Kolbush-Jackson, Donna
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	35,464	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	35,464	 	 	 	 	35,464	 	 	 	0.04	%
	Logan, Honora
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	10,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	10,000	 	 	 	 	10,000	 	 	 	0.01	%
	McLaughlin, Gerald
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	687,289	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	687,289	 	 	 	 	687,289	 	 	 	0.83	%
	Milan, Pola
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	15,786	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	15,786	 	 	 	 	15,786	 	 	 	0.02	%
	Nett, Erica L._assignee of Robert Nett
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	72,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	72,000	 	 	 	 	72,000	 	 	 	0.09	%
	Nett, Nicholas E._assignee of Robert Nett
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	72,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	72,000	 	 	 	 	72,000	 	 	 	0.09	%
	Richardson, Lauren
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	25,572	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	25,572	 	 	 	 	25,572	 	 	 	0.03	%
	Siegel, Steven
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	20,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	20,000	 	 	 	 	20,000	 	 	 	0.02	%
	Stiles, Deborah
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	5,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	5,000	 	 	 	 	5,000	 	 	 	0.01	%
	Sussman, Joel
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	26,457	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	26,457	 	 	 	 	26,457	 	 	 	0.03	%
	Whetstone, Robert
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	75,000	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	75,000	 	 	 	 	75,000	 	 	 	0.09	%
	Oxford Finance Corp
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	134,408	 	 	 	 	 	 	 	 	 	 	 	134,408	 	 	 	 	134,408	 	 	 	0.16	%
	Outstanding Shares Pool
	 	 	 	 	 	 	 	 	 	 	 	0	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	831,103	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	831,103	 	 	 	 	831,103	 	 	 	1.00	%
	Totals
	 	 	 	3,072,655	 	 	 	71,250	 	 	 	3,131,250	 	 	 	16,922,506	 	 	 	36,173,834	 	 	 	14,122,924	 	 	 	 	8,366,095	 	 	 	134,408	 	 	 	736,514	 	 	 	3,399,493	 	 	 	12,636,510	 	 	 	 	82,987,024	 	 	 	100.00	%