Securities Purchase Agreement, dated as of April 16, 2012



 Exhibit 10.1 
 SECURITIES PURCHASE AGREEMENT 
 This Securities Purchase Agreement (this
“Agreement”) is dated as of April 16, 2012, between EnteroMedics Inc., a Delaware corporation (the “Company”), and Kevin Douglas through his family trusts identified on Schedule A hereto (the “Purchaser”).

 WHEREAS, subject to the terms and conditions set forth in this Agreement and pursuant to an effective registration statement
under the Securities Act, the Company desires to issue and sell to the Purchaser, and the Purchaser desires to purchase from the Company, securities of the Company as more fully described in this Agreement. 

NOW, THEREFORE, IN CONSIDERATION of the mutual covenants contained in this Agreement, and for other good and valuable consideration the
receipt and adequacy of which are hereby acknowledged, the Company and the Purchaser agree as follows: 
 ARTICLE I.

 DEFINITIONS 
 1.1 Definitions. In addition to the terms defined elsewhere in this Agreement, for all purposes of this Agreement, the following terms have the meanings set forth in this Section 1.1:

 “Action” shall have the meaning ascribed to such term in Section 3.1(j). 

“Activities to Date” shall have the meaning ascribed to such term in Section 3.1(ee). 

“Affiliate” means any Person that, directly or indirectly through one or more intermediaries, controls or is controlled by or is under common
control with a Person as such terms are used in and construed under Rule 405 under the Securities Act. 
 “Board of Directors” means
the board of directors of the Company. 
 “Business Day” means any day except any Saturday, any Sunday, any day which is a federal
legal holiday in the United States or any day on which banking institutions in the State of New York are closed. 
 “Closing” means
the closing of the purchase and sale of the Securities pursuant to Section 2.1. 
 “Closing Date” means the Trading Day on which
all of the Transaction Documents have been executed and delivered by the applicable parties thereto, and all conditions precedent to (i) the Purchaser’s obligation to pay the Subscription Amount and (ii) the Company’s obligations
to deliver the Securities, in each case, have been satisfied or waived. 
 “Commission” means the United States Securities and
Exchange Commission. 
 “Common Stock” means the common shares of the Company, par value $0.01 per share, and any other class of
securities into which such securities may hereafter be reclassified or changed. 







 “Common Stock Equivalents” means any securities of the Company or the Subsidiaries which would
entitle the holder thereof to acquire at any time Common Stock, including, without limitation, any debt, preferred stock, rights, options, warrants or other instrument that is at any time convertible into or exercisable or exchangeable for, or
otherwise entitles the holder thereof to receive, Common Stock. 
 “Company Counsel” means Dorsey & Whitney LLP. 

“Company Intellectual Property Rights” shall have the meaning ascribed to such term in Section 3.1(o). 

“Company Patent Applications” shall have the meaning ascribed to such term in Section 3.1(o). 

“DWAC” shall have the meaning ascribed to such term in Section 2.2(a)(iii). 
 “Disclosure Schedules” means the Disclosure Schedules of the Company delivered concurrently herewith. 
 “Effective Date” shall have the meaning ascribed to such term in Section 3.1(f). 

“Evaluation Date” shall have the meaning ascribed to such term in Section 3.1(r). 

“Exchange Act” means the Securities Exchange Act of 1934, as amended, and the rules and regulations promulgated thereunder. 

“FDA” shall have the meaning ascribed to such term in Section 3.1(dd). 
 “FDCA” shall have the meaning ascribed to such term in Section 3.1(dd). 

“GAAP” shall have the meaning ascribed to such term in Section 3.1(h). 
 “Intellectual Property Rights” shall have the meaning ascribed to such term in Section 3.1(o). 
 “IP Counsel” means Merchant & Gould P.C. 
 “Liens” means a lien,
charge, security interest, encumbrance, right of first refusal, preemptive right or other restriction. 
 “Material Adverse Effect”
shall have the meaning assigned to such term in Section 3.1(b). 
 “NASDAQ Approval” means the approval by the NASDAQ of the
Company’s additional listing application with regard to the issuance of the Securities. 

  
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 “Per Share Purchase Price” equals $2.223, subject to adjustment for reverse and forward stock
splits, stock dividends, stock combinations and other similar transactions of the Common Stock that occur after the date of this Agreement. 

“Person” means an individual or corporation, partnership, trust, incorporated or unincorporated association, joint venture, limited liability
company, joint stock company, government (or an agency or subdivision thereof) or other entity of any kind. 
 “Product” shall have
the meaning ascribed to such term in Section 3.1(dd). 
 “Placement Agent” means Craig-Hallum Capital Group LLC. 

“Proceeding” means an action, claim, suit, investigation or proceeding (including, without limitation, an informal investigation or partial
proceeding, such as a deposition), whether commenced or threatened. 
 “Prospectus” means the final prospectus filed for the
Registration Statement. 
 “Prospectus Supplement” means the supplement to the Prospectus complying with Rule 424(b) of the Securities
Act that is filed with the Commission and delivered by the Company to the Purchaser prior to the Closing. 
 “PTO” shall have the
meaning ascribed to such term in Section 3.1(o). 
 “Purchaser Party” shall have the meaning ascribed to such term in
Section 4.5. 
 “Registration Statement” means the effective registration statement with Commission file No. 333-166011.

 “Regulatory Counsel” means Fredrikson & Byron P.A. 
 “Regulatory Licenses” shall have the meaning ascribed to such term in Section 3.1(ee). 
 “Required Approvals” shall have the meaning ascribed to such term in Section 3.1(e). 
 “Rule 144” means Rule 144 promulgated by the Commission pursuant to the Securities Act, as such Rule may be amended from time to time, or any similar rule or regulation hereafter adopted by the
Commission having substantially the same effect as such Rule. 
 “Rule 424” means Rule 424 promulgated by the Commission pursuant to
the Securities Act, as such Rule may be amended or interpreted from time to time, or any similar rule or regulation hereafter adopted by the Commission having substantially the same purpose and effect as such Rule. 

“Sarbanes-Oxley Act” shall have the meaning ascribed to such term in Section 3.1(aa). 

  
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 “SEC Reports” shall have the meaning ascribed to such term in Section 3.1(h). 

“Securities” means the Shares. 

“Securities Act” means the Securities Act of 1933, as amended, and the rules and regulations promulgated thereunder. 

“Shares” shall have the meaning ascribed to such term in Section 2.1. 
 “Short Sales” means all “short sales” as defined in Rule 200 of Regulation SHO under the Exchange Act (but shall not be deemed to include the location and/or reservation of borrowable
shares of Common Stock). 
 “Subscription Amount” shall have the meaning ascribed to such term in Section 2.1. 

“Subsidiary” means any subsidiary of the Company as set forth on Schedule 3.1(a), and shall, where applicable, also include any direct or
indirect subsidiary of the Company formed or acquired after the date hereof. 
 “Trading Day” means a day on which the principal
Trading Market is open for trading. 
 “TGA” shall have the meaning ascribed to such term in Section 3.1(ee). 

“Trading Market” means any of the following markets or exchanges on which the Common Stock is listed or quoted for trading on the date in
question: the NYSE, the AMEX, the NASDAQ Capital Market, the NASDAQ Global Market, the NASDAQ Global Select Market, or the New York Stock Exchange (or any successors to any of the foregoing). 
 “Transaction Documents” means this Agreement and any other documents or agreements executed in connection with the transactions contemplated hereunder. 

“Transfer Agent” means Wells Fargo Bank, National Association, the current transfer agent of the Company, with a mailing address of Wells Fargo
Shareowner Services, 161 North Concord Exchange, South St. Paul, MN 55075 and a facsimile number of (651) 450-4078, and any successor transfer agent of the Company. 
 ARTICLE II. 
 PURCHASE AND SALE 

2.1 Closing. On the Closing Date, upon the terms and subject to the conditions set forth herein, substantially concurrent with the execution and
delivery of this Agreement by the parties hereto, the Company agrees to sell, and the Purchaser agrees to purchase 2,271,705 shares of Common Stock (the “Shares”) at the Per Share Purchase Price for an aggregate purchase price of
$5,050,000.22 (the “Subscription Amount”). The Shares shall be sold pursuant to the Registration Statement. The Purchaser shall deliver the Subscription Amount to the Company 

  
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and the Company shall deliver the Shares to the Purchaser as set forth in Section 2.2(a). The Company and the Purchaser shall deliver the other items set forth in Section 2.2
deliverable at the Closing. Upon satisfaction of the covenants and conditions set forth in Sections 2.2 and 2.3, the Closing shall occur at the offices of Company Counsel, 50 South Sixth Street, Suite 1500, Minneapolis, Minnesota 55402 or such other
location as the parties shall mutually agree. This transaction will close in accordance with Rule 15c6-1 of the Exchange Act. 
 2.2
Deliveries. 
 (a) On or prior to the Closing Date, the Company shall deliver or cause to be delivered to the Purchaser the
following: 
 (i) this Agreement duly executed by the Company; 

(ii) legal opinions of Company Counsel, IP Counsel and Regulatory Counsel delivered and addressed to the Purchaser and the
Placement Agent, in each case in the form provided to and accepted by or on behalf of the Purchaser prior to the signing of this Agreement; 
 (iii) a copy of the irrevocable instructions to the Transfer Agent instructing the Transfer Agent to deliver the Shares registered in the name of the Purchaser via the Depository Trust Company Deposit
Withdrawal Agent Commission System (“DWAC”); 
 (iv) the Prospectus and Prospectus Supplement (which
may be delivered in accordance with Rule 172 under the Securities Act); and 
 (v) a letter of
Deloitte & Touche LLP, delivered and addressed to the Placement Agent, confirming that it is an independent public accounting firm within the meaning of the Securities Act and is in compliance with the applicable requirements relating to
the qualifications of accountants under Rule 2-01 of Regulation S-X of the Commission, and stating, as of the date of such letter (or, with respect to matters involving changes or developments since the respective dates as of which specified
financial information is given in the Registration Statement, Prospectus and Prospectus Supplement, as of a date not prior to the date hereof or more than five days prior to the date of such letter), the conclusions and findings of said firm with
respect to the financial information and other matters covered by its letter delivered concurrently with the execution of this Agreement, and the effect of the letter so to be delivered on such Closing Date shall be to confirm the conclusions and
findings set forth in such prior letter. 
 (b) On or prior to the Closing Date, the Purchaser shall deliver or cause to be
delivered to the Company the following: 
 (i) this Agreement duly executed by the Purchaser; and 

  
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 (ii) the Subscription Amount by wire transfer of immediately available funds
to the account as specified in writing by the Company and delivered to the Purchaser prior to the Closing. 
 2.3 Closing Conditions.

 (a) The obligations of the Company hereunder in connection with the Closing are subject to the following conditions being
met: 
 (i) the accuracy in all material respects on the Closing Date of the representations and warranties of
the Purchaser contained herein (unless as of a specific date therein); 
 (ii) all obligations, covenants and
agreements of the Purchaser required to be performed at or prior to the Closing Date shall have been performed; and 
 (iii) the delivery by the Purchaser of the items set forth in Section 2.2(b) of this Agreement. 
 (b) The obligations of the Purchaser hereunder in connection with the Closing are subject to the following conditions being met: 

(i) the accuracy in all material respects when made and on the Closing Date of the representations and warranties of the
Company contained herein (unless as of a specific date therein); 
 (ii) all obligations, covenants and
agreements of the Company required to be performed at or prior to the Closing Date shall have been performed; 

(iii) the delivery by the Company of the items set forth in Section 2.2(a) of this Agreement; 

(iv) there shall have been no Material Adverse Effect with respect to the Company since the date hereof; 

(v) the NASDAQ Approval shall have been obtained; and 

(vi) from the date hereof to the Closing Date, trading in the Common Stock shall not have been suspended by the Commission
or the Company’s principal Trading Market (except for any suspension of trading of limited duration agreed to by the Company, which suspension shall be terminated prior to the Closing), and, at any time prior to the Closing Date, trading in
securities generally as reported by Bloomberg L.P. shall not have been suspended or limited, or minimum prices shall not have been established on securities whose trades are reported by such service, or on any Trading Market, nor shall a banking
moratorium have been declared either by the United States or New York State authorities nor shall there have occurred any material outbreak or 

  
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escalation of hostilities or other national or international calamity of such magnitude in its effect on, or any material adverse change in, any financial market which, in each case, in the
reasonable judgment of the Purchaser, makes it impracticable or inadvisable to purchase the Securities at the Closing. 

ARTICLE III. 
 REPRESENTATIONS AND WARRANTIES 
 3.1 Representations and Warranties of the Company.
Except as set forth in the SEC Reports or the Disclosure Schedules, which Disclosure Schedules shall be deemed a part hereof and shall qualify any representation or otherwise made herein to the extent of the disclosure contained in the corresponding
section of the Disclosure Schedules, the Company hereby makes the following representations and warranties to the Purchaser: 

(a) Subsidiaries. All of the direct and indirect subsidiaries of the Company are set forth on Schedule 3.1(a). Except as set forth
on Schedule 3.1(a), the Company owns, directly or indirectly, all of the capital stock or other equity interests of each Subsidiary free and clear of any Liens, and all of the issued and outstanding shares of capital stock of each Subsidiary are
validly issued and are fully paid, non-assessable and free of preemptive and similar rights to subscribe for or purchase securities. No Subsidiary of the Company is currently prohibited, directly or indirectly, from paying any dividends to the
Company, from making any other distribution on such Subsidiary’s capital stock, from repaying to the Company any loans or advances to such subsidiary from the Company or from transferring any of such Subsidiary’s property or assets to the
Company or any other Subsidiary of the Company, except as described in or contemplated by the Prospectus. 
 (b) Organization
and Qualification. The Company and each of the Subsidiaries is an entity duly incorporated or otherwise organized, validly existing and in good standing under the laws of the jurisdiction of its incorporation or organization, with the requisite
power and authority to own and use its properties and assets and to carry on its business as currently conducted. Neither the Company nor any Subsidiary is in violation nor default of any of the provisions of its respective certificate or articles
of incorporation, bylaws or other organizational or charter documents. Each of the Company and the Subsidiaries is duly qualified to conduct business and is in good standing as a foreign corporation or other entity in each jurisdiction in which the
nature of the business conducted or property owned by it makes such qualification necessary, except where the failure to be so qualified or in good standing, as the case may be, could not have or reasonably be expected to result in a Material
Adverse Effect (as defined below). A “Material Adverse Effect” means: (i) an adverse effect on the legality, validity or enforceability of any Transaction Document which materially adversely affects Purchaser’s rights under such
Transaction Document, (ii) a material adverse effect on the historical, near-term or long-term projected business, assets, properties, results of operations, condition (financial or otherwise) or prospects of the Company and its Subsidiaries,
taken as a whole, or (iii) a material adverse effect on the Company’s ability to perform in any material respect on a timely basis its obligations under any Transaction Document, or (iv) changes in general economic, regulatory or
political conditions, or securities markets in the United States or worldwide or any outbreak of hostilities, terrorist activities or war, or any material worsening of 

  
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any such hostilities, activities or war underway as of the date hereof, which changes adversely affect the Company and its Subsidiaries taken as a whole in a disproportionate manner relative to
the other participants in the industries in which the Company and its Subsidiaries operate. 
 (c) Authorization;
Enforcement. The Company has the requisite corporate power and authority to enter into and to consummate the transactions contemplated by each of the Transaction Documents and otherwise to carry out its obligations hereunder and thereunder. The
execution and delivery of each of the Transaction Documents by the Company and the consummation by it of the transactions contemplated hereby and thereby have been duly authorized by all necessary action on the part of the Company and no further
action is required by the Company, the Board of Directors or the Company’s stockholders in connection therewith other than in connection with the Required Approvals. Each Transaction Document to which it is a party has been (or upon delivery
will have been) duly executed by the Company and, when delivered in accordance with the terms hereof and thereof, will constitute the valid and binding obligation of the Company enforceable against the Company in accordance with its terms, except
(i) as limited by general equitable principles and applicable bankruptcy, insolvency, reorganization, moratorium and other laws of general application affecting enforcement of creditors’ rights generally, (ii) as limited by laws
relating to the availability of specific performance, injunctive relief or other equitable remedies and (iii) insofar as indemnification and contribution provisions may be limited by applicable law. 

(d) No Conflicts. The execution, delivery and performance by the Company of the Transaction Documents, the issuance and sale of
the Securities and the consummation by it of the transactions contemplated hereby and thereby to which it is a party do not and will not (i) conflict with or violate any provision of the Company’s or any Subsidiary’s certificate or
articles of incorporation, bylaws or other organizational or charter documents, or (ii) conflict with, or constitute a default (or an event that with notice or lapse of time or both would become a default) under, result in the creation of any
Lien upon any of the properties or assets of the Company or any Subsidiary, or give to others any rights of termination, amendment, acceleration or cancellation (with or without notice, lapse of time or both) of, any agreement, credit facility, debt
or other instrument (evidencing a Company or Subsidiary debt or otherwise) or other understanding to which the Company or any Subsidiary is a party or by which any property or asset of the Company or any Subsidiary is bound or affected, or
(iii) subject to the Required Approvals, conflict with or result in a violation of any law, rule, regulation, order, judgment, injunction, decree or other restriction of any court or governmental authority to which the Company or a Subsidiary
is subject (including federal and state securities laws and regulations), or by which any property or asset of the Company or a Subsidiary is bound or affected; except in the case of each of clauses (ii) and (iii), such as could not have or
reasonably be expected to result in a Material Adverse Effect. 
 (e) Filings, Consents and Approvals. The Company is not
required to obtain any consent, waiver, authorization or order of, give any notice to, or make any filing or registration with, any court or other federal, state, local or other governmental authority or other Person in connection with the
execution, delivery and performance by the Company of the Transaction Documents, other than: (i) the filings required pursuant to Section 4.2 of this Agreement, (ii) the filing with the Commission of the Prospectus Supplement,
(iii) application(s) to each applicable 

  
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Trading Market for the listing of the Securities for trading thereon in the time and manner required thereby and (iv) such filings as are required to be made under applicable state
securities laws (collectively, the “Required Approvals”). 
 (f) Issuance of the Securities; Registration. The
Securities are duly authorized and, when issued and paid for in accordance with the applicable Transaction Documents, will be duly and validly issued, fully paid and nonassessable, free and clear of all Liens imposed by the Company. The Company has
prepared and filed the Registration Statement in conformity with the requirements of the Securities Act, which became effective on May 6, 2010 (the “Effective Date”), including the Prospectus, and such amendments and supplements
thereto as may have been required to the date of this Agreement. The Registration Statement is effective under the Securities Act and no stop order preventing or suspending the effectiveness of the Registration Statement or suspending or preventing
the use of the Prospectus has been issued by the Commission and no proceedings for that purpose have been instituted or, to the knowledge of the Company, are threatened by the Commission. The Company, if required by the rules and regulations of the
Commission, proposes to file the Prospectus Supplement, with the Commission pursuant to Rule 424(b). At the time the Registration Statement and any amendments thereto became effective, at the date of this Agreement and at the Closing Date, the
Registration Statement and any amendments thereto conformed and will conform in all material respects to the requirements of the Securities Act and did not and will not contain any untrue statement of a material fact or omit to state any material
fact required to be stated therein or necessary to make the statements therein not misleading; and the Prospectus and any amendments or supplements thereto, at time the Prospectus or any amendment or supplement thereto was issued and first used and
at the Closing Date, conformed and will conform in all material respects to the requirements of the Securities Act and did not and will not contain an untrue statement of a material fact or omit to state a material fact necessary in order to make
the statements therein, in light of the circumstances under which they were made, not misleading. At the earliest time after the filing of the Registration Statement that the Company or another offering participant made a bona fide offer
(within the meaning of Rule 164(h)(2) under the Securities Act) of the Shares and at the date hereof, the Company was not and is not an “ineligible issuer,” as defined in Rule 405 under the Securities Act, including the Company or any
Subsidiary in the preceding three years not having been convicted of a felony or misdemeanor or having been made the subject of a judicial or administrative decree or order as described in Rule 405 (without taking account of any determination by the
Commission pursuant to Rule 405 that it is not necessary that the Company be considered an ineligible issuer), nor an “excluded issuer” as defined in Rule 164 under the Securities Act. 

(g) Capitalization. The capitalization of the Company as of December 31, 2011 is as set forth in the Company’s Annual
Report on Form 10-K for the fiscal year ended December 31, 2011. Except as set forth on Schedule 3.1(g), the Company has not issued any capital stock since its most recently filed periodic report under the Exchange Act, other than pursuant to
the exercise of employee stock options under the Company’s 2003 Stock Incentive Plan and pursuant to the conversion and/or exercise of Common Stock Equivalents outstanding as of the date of the most recently filed periodic report under the
Exchange Act. No Person has any right of first refusal, preemptive right, right of participation, or any similar right to participate in the transactions contemplated by the Transaction Documents, except as may have been waived by such Person


  
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prior to the date hereof. Except as a result of the purchase and sale of the Securities and except as set forth on Schedule 3.1(g), there are no outstanding options, warrants, scrip rights to
subscribe to, calls or commitments of any character whatsoever relating to, or securities, rights or obligations convertible into or exercisable or exchangeable for, or giving any Person any right to subscribe for or acquire, any shares of Common
Stock, or contracts, commitments, understandings or arrangements by which the Company or any Subsidiary is or may become bound to issue additional shares of Common Stock or Common Stock Equivalents. The issuance and sale of the Securities will not
obligate the Company to issue shares of Common Stock or other securities to any Person (other than the Purchaser) and, except as set forth on Schedule 3.1(g), will not result in a right of any holder of Company securities to adjust the exercise,
conversion, exchange or reset price under any of such securities or require the registration of any additional securities of the Company or its Subsidiaries. All of the outstanding shares of capital stock of the Company are validly issued, fully
paid and nonassessable, have been issued in compliance with all federal and state securities laws, and none of such outstanding shares was issued in violation of any preemptive rights or similar rights to subscribe for or purchase securities. No
further approval or authorization of any stockholder, the Board of Directors or others (except as set forth on Schedule 3.1(g)) is required for the issuance and sale of the Securities. Except for agreements filed as exhibits to the SEC Reports,
there are no stockholders agreements, voting agreements or other similar agreements with respect to the Company’s capital stock to which the Company is a party or, to the knowledge of the Company, between or among any of the Company’s
stockholders. 
 (h) SEC Reports; Financial Statements. The Company has filed all reports, schedules, forms, statements
and other documents required to be filed by the Company under the Securities Act and the Exchange Act, including pursuant to Section 13(a) or 15(d) thereof, for the two years preceding the date hereof (or such shorter period as the Company was
required by law or regulation to file such material) (the foregoing materials, including the exhibits thereto and documents incorporated by reference therein, together with the Registration Statement, Prospectus and the Prospectus Supplement, being
collectively referred to herein as the “SEC Reports”) on a timely basis or has received a valid extension of such time of filing and has filed any such SEC Reports prior to the expiration of any such extension. As of their respective
dates, the SEC Reports complied in all material respects with the requirements of the Securities Act and the Exchange Act, as applicable, and none of the SEC Reports, when filed, contained any untrue statement of a material fact or omitted to state
a material fact required to be stated therein or necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading. The Company has never been an issuer subject to Rule 144(i) under the
Securities Act. The financial statements of the Company included in the SEC Reports comply in all material respects with applicable accounting requirements and the rules and regulations of the Commission with respect thereto as in effect at the time
of filing. Such financial statements have been prepared in accordance with United States generally accepted accounting principles applied on a consistent basis during the periods involved (“GAAP”), except as may be otherwise specified in
such financial statements or the notes thereto and except that unaudited financial statements may not contain all footnotes required by GAAP, and fairly present in all material respects the financial position of the Company and its consolidated
Subsidiaries as of and for the dates thereof and the results of operations and cash flows for the periods then ended, subject, in the case of unaudited statements, to normal, immaterial, year-end


  
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audit adjustments. All non-GAAP financial information included in the SEC Reports complies with the requirements of Regulation G and Item 10 of Regulation S-K under the Securities Act; and,
there are no material off-balance sheet arrangements (as defined in Regulation S-K under the Securities Act, Item 303(a)(4)(ii)) or any other relationships with unconsolidated entities or other persons, that may have a material current or, to
the Company’s knowledge, material future effect on the Company’s financial condition, results of operations, liquidity, capital expenditures, capital resources or significant components of revenue or expenses. No other financial statements
or schedules are required to be included in the Registration Statement or the Prospectus. 
 (i) Material Changes;
Undisclosed Events, Liabilities or Developments. Since the date of the latest audited financial statements included within the SEC Reports, except as specifically disclosed in a subsequent SEC Report filed prior to the date hereof,
(i) there has been no event, occurrence or development that has had or that could reasonably be expected to result in a Material Adverse Effect, (ii) the Company has not incurred any liabilities (contingent or otherwise) other than
(A) trade payables and accrued expenses incurred in the ordinary course of business consistent with past practice and (B) liabilities not required to be reflected in the Company’s financial statements pursuant to GAAP or disclosed in
filings made with the Commission, (iii) the Company has not altered its method of accounting, (iv) the Company has not declared or made any dividend or distribution of cash or other property to its stockholders or purchased, redeemed or
made any agreements to purchase or redeem any shares of its capital stock and (v) the Company has not issued any equity securities to any officer, director or Affiliate, except pursuant to existing Company stock option plans. Except for the
issuance of the Securities contemplated by this Agreement or as set forth on Schedule 3.1(i), no event, liability, fact, circumstance, occurrence or development has occurred or exists or is reasonably expected to occur or exist with respect to the
Company or its Subsidiaries or their respective business, properties, operations, assets or financial condition that would be required to be disclosed by the Company under applicable securities laws at the time this representation is made or deemed
made that has not been publicly disclosed at least one Trading Day prior to the date that this representation is made. 
 (j)
Litigation. Except as disclosed in the SEC Reports, there is no action, suit, inquiry, notice of violation, proceeding or investigation pending or, to the knowledge of the Company, threatened against or affecting the Company, any Subsidiary
or any of their respective properties, officers or directors before or by any court, arbitrator, governmental or administrative agency or regulatory authority (federal, state, county, local or foreign) (collectively, an “Action”) which
(i) adversely affects or challenges the legality, validity or enforceability of any of the Transaction Documents or the Securities or (ii) could, if there were an unfavorable decision, have or reasonably be expected to result in a Material
Adverse Effect. Neither the Company nor any Subsidiary, nor any director or officer thereof, is or has been within the last five (5) years the subject of any Action involving a claim of violation of or liability under federal or state
securities laws or a claim of breach of fiduciary duty. There are no current or, to the knowledge of the Company, pending, legal, governmental or regulatory actions, suits or proceedings (x) to which the Company or its Subsidiaries are subject
or (y) which has as the subject thereof any officer or director of the Company, any employee plan sponsored by the Company or any property or assets owned or leased by the Company, that are required to be described in the Registration


  
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Statement and Prospectus by the Securities Act and that have not been so described. There has not been, and to the knowledge of the Company, there is not pending or contemplated, any
investigation by the Commission targeting the Company or any current or former director or officer of the Company. The Commission has not issued any stop order or other order suspending the effectiveness of any registration statement filed by the
Company or any Subsidiary under the Exchange Act or the Securities Act. 
 (k) Labor Relations. No material labor dispute
exists or, to the knowledge of the Company, is imminent with respect to any of the employees of the Company, which could reasonably be expected to result in a Material Adverse Effect. None of the Company’s or its Subsidiaries’ employees is
a member of a union that relates to such employee’s relationship with the Company or such Subsidiary, and neither the Company nor any of its Subsidiaries is a party to a collective bargaining agreement, and the Company and its Subsidiaries
believe that their relationships with their employees are good. No executive officer, to the knowledge of the Company, is, or is now expected to be, in violation of any material term of any employment contract, confidentiality, disclosure or
proprietary information agreement or non-competition agreement, or any other contract or agreement or any restrictive covenant in favor of any third party, and the continued employment of each such executive officer does not subject the Company or
any of its Subsidiaries to any liability with respect to any of the foregoing matters. The Company and its Subsidiaries are in compliance with all U.S. federal, state, local and foreign laws and regulations relating to employment and employment
practices, terms and conditions of employment and wages and hours, except where the failure to be in compliance could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect. To the knowledge of the Company,
no “prohibited transaction” as defined under Section 406 of ERISA or Section 4975 of the Internal Revenue Code and not exempt under ERISA Section 408 and the regulations and published interpretations thereunder has occurred
with respect to any employee benefit plan. At no time has the Company or any ERISA Affiliate maintained, sponsored, participated in, contributed to or has or had any liability or obligation in respect of any employee benefit plan subject to Part 3
of Subtitle B of Title I of ERISA, Title IV of ERISA, or Section 412 of the Internal Revenue Code or any “multiemployer plan” as defined in Section 3(37) of ERISA or any multiple employer plan for which the Company or any ERISA
Affiliate has incurred or could incur liability under Section 4063 or 4064 of ERISA. No employee benefit plan provides or promises, or at any time provided or promised, retiree health, life insurance, or other retiree welfare benefits except as
may be required by the Consolidated Omnibus Budget Reconciliation Act of 1985 or similar state law. Each employee benefit plan is and has been operated in material compliance with its terms and all applicable laws, including but not limited to ERISA
and the Internal Revenue Code and, to the knowledge of the Company, no event has occurred (including a “reportable event” as such term is defined in Section 4043 of ERISA) and no condition exists that would subject the Company or any
ERISA Affiliate to any material tax, fine, lien, penalty or liability imposed by ERISA, the Internal Revenue Code or other applicable law. Each employee benefit plan intended to be qualified under Internal Revenue Code Section 401(a) is so
qualified and has a favorable determination or opinion letter from the Internal Revenue Service upon which it can rely, and any such determination or opinion letter remains in effect and has not been revoked; to the knowledge of the Company, nothing
has occurred since the date of any such determination or opinion letter that is reasonably likely to adversely affect such qualification; (ii) with respect to each foreign benefit plan, such foreign


  
 12 









 
benefit plan (A) if intended to qualify for special tax treatment, meets, in all material respects, the requirements for such treatment, and (B) if required to be funded, is funded to
the extent required by applicable law, and with respect to all other foreign benefit plans, adequate reserves therefore have been established on the accounting statements of the applicable Company or subsidiary; (iii) the Company does not have
any obligations under any collective bargaining agreement with any union and no organization efforts are underway with respect to Company employees. “Employee benefit plan” means any “employee benefit plan” within the meaning of
Section 3(3) of ERISA, including, without limitation, all stock purchase, stock option, stock-based severance, employment, change-in-control, medical, disability, fringe benefit, bonus, incentive, deferred compensation, employee loan and all
other employee benefit plans, agreements, programs, policies or other arrangements, whether or not subject to ERISA, under which (A) any current or former employee, director or independent contractor of the Company or its subsidiary has any
present or future right to benefits and which are contributed to, sponsored by or maintained by the Company or its subsidiary or (B) the Company or its subsidiary has had or has any present or future obligation or liability; “ERISA”
means the Employee Retirement Income Security Act of 1974, as amended; “ERISA Affiliate” means any member of the company’s controlled group as defined in Code Section 414(b), (c), (m) or (o); and “Foreign benefit
plan” means any employee benefit plan established, maintained or contributed to outside of the United States of America or which covers any employee working or residing outside of the United States. 

(l) Compliance. Neither the Company nor any Subsidiary: (i) is in default under or in violation of (and no event has occurred
that has not been waived that, with notice or lapse of time or both, would result in a default by the Company or any Subsidiary under), nor has the Company or any Subsidiary received notice of a claim that it is in default under or that it is in
violation of, any indenture, loan or credit agreement or any other agreement or instrument to which it is a party or by which it or any of its properties is bound (whether or not such default or violation has been waived), (ii) is in violation
of any judgment, decree or order of any court, arbitrator or governmental body or (iii) is or has been in violation of any statute, rule, ordinance or regulation of any governmental authority, including without limitation all foreign, federal,
state and local laws applicable to its business and all such laws that affect the environment, except in each case as could not have or reasonably be expected to result in a Material Adverse Effect. 

(m) Regulatory Permits. The Company and the Subsidiaries possess all certificates, authorizations and permits issued by the
appropriate federal, state, local or foreign regulatory authorities necessary to conduct their respective businesses as described in the SEC Reports, except where the failure to possess such permits could not reasonably be expected to result in a
Material Adverse Effect, and neither the Company nor any Subsidiary has received any notice of proceedings relating to the revocation or modification of any such permit. 
 (n) Title to Assets. Except as set forth on Schedule 3.1(n), the Company and the Subsidiaries have good and marketable title in fee simple to all real and personal property owned by them and good
and marketable title in all personal property owned by them that is material to the business of the Company and the Subsidiaries, in each case free and clear of all Liens, except for Liens as do not materially affect the value of such property and
do not materially interfere 

  
 13 









 
with the use made and proposed to be made of such property by the Company and the Subsidiaries and Liens for the payment of federal, state or other taxes, the payment of which is neither
delinquent nor subject to penalties. Any property and facilities held under lease by the Company and the Subsidiaries are held by them under valid, subsisting and enforceable leases with which the Company and the Subsidiaries are in compliance.

 (o) Patents and Trademarks. The Company and the Subsidiaries have, or have rights under, all patents, patent
applications, trademarks, trademark applications, service marks, trade names, trade secrets, inventions, copyrights, licenses and other intellectual property rights and similar rights (“Intellectual Property Rights”) necessary or material
for use in connection with their respective businesses as described in the SEC Reports (collectively, the “Company Intellectual Property Rights”). To the knowledge of the Company, neither the Company nor any Subsidiary violates or
infringes upon the Intellectual Property Rights of any other Person. Neither the Company nor any Subsidiary has received a notice (written or otherwise) that the Company or any Subsidiary violates or infringes upon the Intellectual Property Rights
of any Person; and the Company and its Subsidiaries are not aware of any fact that would form a reasonable basis for any such claim. To the knowledge of the Company, all of the Company Intellectual Property Rights are enforceable and there is no
existing infringement by another Person of any of the Company Intellectual Property Rights. The Company and its Subsidiaries have taken reasonable security measures to protect the secrecy, confidentiality and value of all of their intellectual
properties. To the Company’s knowledge, no employee of the Company or its subsidiary is in or has ever been in violation of any term of any employment contract, patent disclosure agreement, invention assignment agreement, non-competition
agreement, non-solicitation agreement, nondisclosure agreement or any restrictive covenant to or with a former employer where the basis of such violation relates to such employee’s employment with the Company or its Subsidiaries or actions
undertaken by the employee while employed with the Company or its Subsidiaries, except as such violation would not result in a Material Adverse Effect. All patent applications owned by the Company or its subsidiary and filed with the U.S. Patent and
Trademark Office (the “PTO”) or any foreign or international patent authority that have resulted in patents or currently pending applications that describe inventions necessary to conduct the business of the Company or its Subsidiaries in
the manner described in the Registration Statement (collectively, the “Company Patent Applications”) have been or were duly and properly filed. The Company and its Subsidiaries have complied with their duty of candor and disclosure to the
PTO for the Company Patent Applications. The Company is not aware of any facts required to be disclosed to the PTO that were not disclosed to the PTO and which would preclude the grant of a patent for the Company Patent Applications. The Company has
no knowledge of any facts which would preclude it from having clear title to the Company Patent Applications that have been identified by the Company as being exclusively owned by the Company. 

(p) Insurance. The Company and the Subsidiaries are insured by insurers of recognized financial responsibility against such losses
and risks and in such amounts as are prudent and customary in the businesses in which the Company and the Subsidiaries are engaged, including, but not limited to, directors and officers insurance coverage at least equal to the aggregate Subscription
Amount. There are no claims by the Company or its Subsidiaries under any such policy or instrument as to which any insurance company is denying liability or 

  
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defending under a reservation of rights clause. Neither the Company nor any Subsidiary has any reason to believe that it will not be able to renew its existing insurance coverage as and when such
coverage expires or to obtain similar coverage from similar insurers as may be necessary to continue its business without a significant increase in cost. 
 (q) Transactions With Affiliates and Employees. Except as set forth in the SEC Reports, none of the officers or directors of the Company and, to the knowledge of the Company, none of the employees
of the Company is presently a party to any transaction with the Company or any Subsidiary (other than for services as employees, officers and directors), including any contract, agreement or other arrangement providing for the furnishing of services
to or by, providing for rental of real or personal property to or from, or otherwise requiring payments to or from any officer, director or such employee or, to the knowledge of the Company, any entity in which any officer, director, or any such
employee has a substantial interest or is an officer, director, trustee or partner, in each case in excess of $120,000, and collectively in excess of $500,000, other than for (i) payment of salary or consulting fees for services rendered,
(ii) reimbursement for expenses incurred on behalf of the Company and (iii) other employee benefits, including stock option agreements under any stock option plan of the Company. 

(r) Sarbanes-Oxley; Internal Accounting Controls. The Company is in compliance with all provisions of the Sarbanes-Oxley Act of
2002 which are applicable to it as of the Closing Date. The Company and the Subsidiaries maintain a system of internal accounting controls sufficient to provide reasonable assurance that: (i) transactions are executed in accordance with
management’s general or specific authorizations, (ii) transactions are recorded as necessary to permit preparation of financial statements in conformity with GAAP and to maintain asset accountability, (iii) access to assets is
permitted only in accordance with management’s general or specific authorization, and (iv) the recorded accountability for assets is compared with the existing assets at reasonable intervals and appropriate action is taken with respect to
any differences. The Company has established disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) for the Company and designed such disclosure controls and procedures to ensure that information required to be
disclosed by the Company in the SEC Reports and the reports it files or submits under the Exchange Act is recorded, processed, summarized and reported, within the time periods specified in the Commission’s rules and forms. The Company’s
certifying officers have evaluated the effectiveness of the Company’s disclosure controls and procedures as of the end of the period covered by the Company’s most recently filed periodic report under the Exchange Act (such date, the
“Evaluation Date”). The Company presented in its most recently filed periodic report under the Exchange Act the conclusions of the certifying officers about the effectiveness of the disclosure controls and procedures based on their
evaluations as of the Evaluation Date. Since the Evaluation Date, there have been no changes in the Company’s internal control over financial reporting (as such term is defined in the Exchange Act) that has materially affected, or is reasonably
likely to materially affect, the Company’s internal control over financial reporting. The Company’s board of directors has, subject to the exceptions, cure periods and the phase-in periods specified in the applicable Trading Market rules,
validly appointed an audit committee to oversee internal accounting controls whose composition satisfies the applicable requirements of the Trading Market rules and the Company’s board of directors and/or the audit committee has adopted a
charter that satisfies the requirements of the Trading Market rules. 

  
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 (s) Certain Fees. Except as set forth in the Prospectus Supplement, no brokerage or
finder’s fees or commissions are or will be payable by the Company to any broker, financial advisor or consultant, finder, placement agent, investment banker, bank or other Person with respect to the transactions contemplated by the Transaction
Documents. The Purchaser shall have no obligation with respect to any fees or with respect to any claims made by or on behalf of other Persons for fees of a type contemplated in this Section that may be due in connection with the transactions
contemplated by the Transaction Documents. 
 (t) Investment Company. The Company is not, and is not an Affiliate of, and
immediately after receipt of payment for the Securities, will not be or be an Affiliate of, an “investment company” within the meaning of the Investment Company Act of 1940, as amended. The Company shall conduct its business in a manner so
that it will not become an “investment company” subject to registration under the Investment Company Act of 1940, as amended. 
 (u) Registration Rights. Except as set forth on Schedule 3.1(u), no Person has any right to cause the Company to effect the registration under the Securities Act of any securities of the Company.

 (v) Listing and Maintenance Requirements. The Common Stock is registered pursuant to Section 12(b) or 12(g) of
the Exchange Act, and the Company has taken no action designed to, or which to its knowledge is likely to have the effect of, terminating the registration of the Common Stock under the Exchange Act nor has the Company received any notification that
the Commission is contemplating terminating such registration. The Common Stock is included or approved for listing on the Nasdaq Capital Market and the Company has not received any notification that the Commission or the Nasdaq Capital Market is
currently contemplating terminating such registration or listing. The applicable conditions for the use of Form S-3 in connection with the offering contemplated by this Agreement, as set forth in the General Instructions thereto, have been
satisfied. The Company has not, in the 12 months preceding the date hereof, received notice from any Trading Market on which the Common Stock is or has been listed or quoted to the effect that the Company is not in compliance with the listing or
maintenance requirements of such Trading Market. The Company is, and has no reason to believe that it will not in the foreseeable future continue to be, in compliance with all such listing and maintenance requirements. 

(w) Disclosure. All of the disclosure furnished by or on behalf of the Company to the Purchaser regarding the Company, its
business and the transactions contemplated hereby, including the Disclosure Schedules to this Agreement, is true and correct and does not contain any untrue statement of a material fact or omit to state any material fact necessary in order to make
the statements made therein, in light of the circumstances under which they were made, not misleading. The press releases disseminated by the Company during the twelve months preceding the date of this Agreement taken as a whole do not contain any
untrue statement of a material fact or omit to state a material fact required to be stated therein or necessary in order to make the statements therein, in light of the circumstances under which they were made and when made, not misleading. The
Company acknowledges and agrees that the Purchaser does not make 

  
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or has not made any representations or warranties with respect to the transactions contemplated hereby other than those specifically set forth in Section 3.2 hereof. There are no statutes,
regulations, contracts or documents that are required to be described in the Registration Statement and in the Prospectus or required to be filed as exhibits to the Registration Statement by the Securities Act that have not been so described or
filed. The documents incorporated by reference in the Registration Statement and in the Prospectus, when they became effective or were filed with the Commission, as the case may be, conformed in all material respects to the requirements of the
Securities Act or the Exchange Act, as applicable, and were filed on a timely basis with the Commission. Any further documents so filed and incorporated by reference in the Registration Statement or in the Prospectus, when such documents are filed
with the Commission, will conform in all material respects to the requirements of the Exchange Act, and will not contain an untrue statement of a material fact or omit to state a material fact necessary to make the statements therein, in the light
of the circumstances under which they were made, not misleading. Any certificate signed by any officer of the Company and delivered to you or to your counsel shall be deemed a representation and warranty by the Company to you as to the matters
covered thereby. 
 (x) No Integrated Offering. Assuming the accuracy of the Purchaser’s representations and
warranties set forth in Section 3.2 and the NASDAQ Approval, neither the Company, nor any of its Affiliates, nor any Person acting on its or their behalf has, directly or indirectly, made any offers or sales of any security or solicited any
offers to buy any security, under circumstances that would cause this offering of the Securities to be integrated with prior offerings by the Company for purposes of any applicable shareholder approval provisions of any Trading Market on which any
of the securities of the Company are listed or designated. 
 (y) Tax Status. Except for matters that would not,
individually or in the aggregate, have or reasonably be expected to result in a Material Adverse Effect, the Company and each Subsidiary has filed all necessary federal, state and foreign income and franchise tax returns and has paid or accrued all
taxes shown as due thereon, and the Company has no knowledge of a tax dispute or deficiency which has been asserted or threatened against the Company or any Subsidiary. 
 (z) Foreign Corrupt Practices. Neither the Company, nor to the knowledge of the Company, any agent or other person acting on behalf of the Company, has (i) directly or indirectly, used any
funds for unlawful contributions, gifts, entertainment or other unlawful expenses related to foreign or domestic political activity, (ii) made any unlawful payment to foreign or domestic government officials or employees or to any foreign or
domestic political parties or campaigns from corporate funds, (iii) failed to disclose fully any contribution made by the Company (or made by any person acting on its behalf of which the Company is aware) which is in violation of law, or
(iv) violated in any material respect any provision of the Foreign Corrupt Practices Act of 1977, as amended. Each of the Company, its Subsidiaries, its Affiliates and any of their respective officers, directors, supervisors, managers, agents,
or employees, has not violated, its participation in the transactions contemplated by this Agreement will not violate, and the Company has instituted and maintains policies and procedures designed to ensure continued compliance with, each of the
following laws: (a) anti-bribery laws, including but not limited to, any applicable law, rule, or regulation of any locality, including but not limited to any 

  
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law, rule, or regulation promulgated to implement the OECD Convention on Combating Bribery of Foreign Public Officials in International Business Transactions, signed December 17, 1997,
including the U.S. Foreign Corrupt Practices Act of 1977, as amended, or any other law, rule or regulation of similar purposes and scope, (b) anti-money laundering laws, including but not limited to, applicable federal, state, international,
foreign or other laws, regulations or government guidance regarding anti-money laundering, including, without limitation, Title 18 US. Code section 1956 and 1957, the Patriot Act, the Bank Secrecy Act, and international anti-money laundering
principles or procedures by an intergovernmental group or organization, such as the Financial Action Task Force on Money Laundering, of which the United States is a member and with which designation the United States representative to the group or
organization continues to concur, all as amended, and any Executive order, directive, or regulation pursuant to the authority of any of the foregoing, or any orders or licenses issued thereunder or (c) laws and regulations imposing U.S.
economic sanctions measures, including, but not limited to, the International Emergency Economic Powers Act, the Trading with the Enemy Act, the United Nations Participation Act and the Syria Accountability and Lebanese Sovereignty Act, all as
amended, and any Executive Order, directive, or regulation pursuant to the authority of any of the foregoing, including the regulations of the United States Treasury Department set forth under 31 CFR, Subtitle B, Chapter V, as amended, or any orders
or licenses issued thereunder. Neither the Company nor its Subsidiaries nor, to the knowledge of the Company, any director, officer or employee of the Company or its Subsidiaries is currently subject to any U.S. sanctions administered by the Office
of Foreign Assets Control of the U.S. Department of the Treasury. 
 (aa) Accountants. To the knowledge and belief of the
Company, Deloitte & Touche LLP, which has expressed its opinion with respect to the financial statements filed as a part of the Registration Statement and included in the Registration Statement and the Prospectus, is (x) an independent
public accounting firm within the meaning of the Securities Act and the Rules and Regulations, (y) a registered public accounting firm (as defined in Section 2(a)(12) of the Sarbanes-Oxley Act of 2002 (the “Sarbanes-Oxley Act”))
and (z) not in violation of the auditor independence requirements of the Sarbanes-Oxley Act. Deloitte & Touche LLP has expressed its opinion with respect to the financial statements included in the Company’s Annual Report on Form
10-K for the year ended December 31, 2011. 
 (bb) Acknowledgment Regarding Purchaser’s Purchase of Securities.
The Company acknowledges and agrees that the Purchaser is acting solely in the capacity of an arm’s length purchaser with respect to the Transaction Documents and the transactions contemplated thereby. The Company further acknowledges that the
Purchaser is not acting as a financial advisor or fiduciary of the Company (or in any similar capacity) with respect to the Transaction Documents and the transactions contemplated thereby and any advice given by the Purchaser or any of its
respective representatives or agents in connection with the Transaction Documents and the transactions contemplated thereby is merely incidental to the Purchaser’s purchase of the Securities. The Company further represents to the Purchaser that
the Company’s decision to enter into this Agreement and the other Transaction Documents has been based solely on the independent evaluation of the transactions contemplated hereby by the Company and its representatives. 

  
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 (cc) Regulation M Compliance. The Company has not, and to its knowledge no one acting
on its behalf has, (i) taken, directly or indirectly, any action designed to cause or to result in the stabilization or manipulation of the price of any security of the Company to facilitate the sale or resale of any of the Securities,
(ii) sold, bid for, purchased, or, paid any compensation for soliciting purchases of, any of the Securities, or (iii) paid or agreed to pay to any Person any compensation for soliciting another to purchase any other securities of the
Company, other than, in the case of clauses (ii) and (iii), compensation paid to the Company’s Placement Agent in connection with the placement of the Securities. 
 (dd) FDA. As to each product subject to the jurisdiction of the U.S. Food and Drug Administration (“FDA”) under the Federal Food, Drug and Cosmetic Act, as amended, and the regulations
thereunder (“FDCA”) that is manufactured, packaged, labeled, tested, distributed, sold, and/or marketed by the Company or any of its Subsidiaries (each such product, a “Product”), such Product is being manufactured, packaged,
labeled, tested, distributed, sold and/or marketed by the Company in compliance with all applicable requirements under FDCA and similar laws, rules and regulations relating to registration, investigational use, premarket clearance, licensure, or
application approval, good manufacturing practices, good laboratory practices, good clinical practices, product listing, quotas, labeling, advertising, record keeping and filing of reports, except where the failure to be in compliance would not have
a Material Adverse Effect. There is no pending, completed or, to the Company’s knowledge, threatened, action (including any lawsuit, arbitration, or legal or administrative or regulatory proceeding, charge, complaint, or investigation) against
the Company or any of its Subsidiaries, and none of the Company or any of its Subsidiaries has received any notice, warning letter or other communication from the FDA or any other governmental entity, which (i) contests the premarket clearance,
licensure, registration, or approval of, the uses of, the distribution of, the manufacturing or packaging of, the testing of, the sale of, or the labeling and promotion of any Product, (ii) withdraws its approval of, requests the recall,
suspension, or seizure of, or withdraws or orders the withdrawal of advertising or sales promotional materials relating to, any Product, (iii) imposes a clinical hold on any clinical investigation by the Company or any of its Subsidiaries,
(iv) enjoins production at any facility of the Company or any of its Subsidiaries, (v) enters or proposes to enter into a consent decree of permanent injunction with the Company or any of its Subsidiaries, or (vi) otherwise alleges
any violation of any laws, rules or regulations by the Company or any of its Subsidiaries, and which, either individually or in the aggregate, would have a Material Adverse Effect. The properties, business and operations of the Company have been and
are being conducted in all material respects in accordance with all applicable laws, rules and regulations of the FDA. The Company has not been informed by the FDA that the FDA will prohibit the marketing, sale, license or use in the United States
of any product proposed to be developed, produced or marketed by the Company nor has the FDA expressed any concern as to approving or clearing for marketing any product being developed or proposed to be developed by the Company. 

(ee) Foreign Device Regulatory Matters. To the knowledge of the Company, the Company’s distributors have obtained all
necessary approvals, clearances, authorizations, licenses and registrations required by the Australian or other non-United States governmental authorities, to permit all activities (including without limitation, pre-clinical testing and commercial
sales in Australia) undertaken by the distributor, if any, to date (the “Activities to 

  
 19 









 
Date”) in jurisdictions where the distributor currently conducts or in the past has conducted such activities on behalf of the Company (collectively, the “Regulatory Licenses”). To
the knowledge of the Company, the Company’s distributors are in compliance in all material respects with all terms and conditions of each Regulatory License and with all applicable laws, rules and regulations pertaining to the Activities to
Date including, without limitation, (i) requirements governing investigational drugs and devices, (ii) regulations related to good laboratory practices and good clinical practices issued by the Australian Therapeutic Goods Administration
(“TGA”) and (iii) the applicable animal welfare laws, the regulations issued thereunder, and any related foreign statutes and regulations. To the knowledge of the Company, the Company’s distributors are in compliance in all
material respects with all applicable reporting requirements for all Regulatory Licenses. To the knowledge of the Company, the Company’s distributors have not received any notice or other communication from the TGA or any other governmental
authority (i) contesting the premarket approval of, the uses of or the labeling and promotion of any product relating to the Company’s products including, without limitation, those products currently under research and/or development by
the Company or (ii) otherwise alleging any violation by the distributor of any law, regulation or other legal provision applicable to any such product. to the Company’s knowledge, the Company’s products are being researched,
developed, manufactured, tested, distributed and/or marketed in compliance in all material respects with all applicable requirements under the Australian medical device laws and similar foreign laws and regulations applicable to such products,
including those relating to investigational use, premarket approval, good manufacturing practices, labeling, advertising, record keeping, filing of reports and security. Neither the Company nor, to the knowledge of the Company, the Company’s
distributors have made an untrue statement of a material fact or fraudulent statement to the TGA or any other governmental authority performing similar functions or failed to disclose a material fact required to be disclosed to the TGA or such other
governmental authority. Research involving human subjects conducted by or on behalf of the Company (i) has been conducted in compliance in all material respects with all applicable federal, state, and foreign statutes and regulations governing
the protection of human subjects, (ii) was approved by an institutional review board, if required, (iii) had the informed consent of the subjects, (iv) complied in all material respects with all applicable foreign statutes and
regulations and (v) did not involve any investigator who has been disqualified as a clinical investigator by the FDA or any other agency or has been found by any agency with jurisdiction to have engaged in scientific misconduct. 

(ff) Clinical Trials. The studies, tests and preclinical and clinical trials conducted by or on behalf of the Company or its
Subsidiaries, or in which the Company or its Subsidiaries have participated, that are described in the SEC Reports were and, if still pending, are, to its knowledge, being conducted in all material respects in accordance with experimental protocols,
procedures and controls pursuant to, where applicable, accepted professional and scientific standards and applicable laws, and the descriptions of the results of such studies, tests and trials contained in the SEC Reports are accurate and complete
in all material respects and fairly present the data derived from such studies, tests or trials in all material respects. The Company has no knowledge of any studies, tests or trials not described in the SEC Reports the results of which reasonably
call into question in any material respect the results of the studies, tests and trials described in the SEC Reports. Neither the Company nor any Subsidiary has received any notices or correspondence from the FDA or any other governmental authority
exercising comparable authority requiring or requesting the termination, suspension or material 

  
 20 









 
modification of any such study, test or trial. The Company and its Subsidiaries have operated and currently are in compliance in all material respects with all applicable FDA rules and
regulations and the Company and its Subsidiaries have not received any notice or other correspondence from the FDA or any other governmental authority requiring the termination, suspension or modification of any of the above referenced feasibility,
pre-clinical or clinical studies or tests. 
 (gg) Third-Party Data. Any third-party statistical and market-related data
included in the Registration Statement and the Prospectus are based on or derived from sources that the Company believes to be reliable and accurate in all material respects. 
 3.2 Representations and Warranties of the Purchaser. The Purchaser hereby represents and warrants as of the date hereof and as of the Closing Date to the Company as follows (unless as of a specific
date therein): 
 (a) Organization; Authority. Such Purchaser is either an individual or an entity duly organized,
validly existing and in good standing under the laws of the jurisdiction of its organization with full right, corporate or partnership power and authority to enter into and to consummate the transactions contemplated by this Agreement and otherwise
to carry out its obligations hereunder and thereunder. The execution and delivery of this Agreement and performance by the Purchaser of the transactions contemplated by this Agreement have been duly authorized by all necessary corporate,
partnership, limited liability company or similar action, as applicable, on the part of the Purchaser. Each Transaction Document to which it is a party has been duly executed by the Purchaser, and when delivered by the Purchaser in accordance with
the terms hereof, will constitute the valid and legally binding obligation of the Purchaser, enforceable against it in accordance with its terms, except: (i) as limited by general equitable principles and applicable bankruptcy, insolvency,
reorganization, moratorium and other laws of general application affecting enforcement of creditors’ rights generally, (ii) as limited by laws relating to the availability of specific performance, injunctive relief or other equitable
remedies and (iii) insofar as indemnification and contribution provisions may be limited by applicable law. 
 (b) Own
Account. The Purchaser is acquiring the Securities as principal for its own account and not with a view to or for distributing or reselling such Securities or any part thereof in violation of the Securities Act or any applicable state securities
law, has no present intention of distributing any of such Securities in violation of the Securities Act or any applicable state securities law and has no direct or indirect arrangement or understandings with any other persons to distribute or
regarding the distribution of such Securities in violation of the Securities Act or any applicable state securities law (this representation and warranty not limiting the Purchaser’s right to sell the Securities pursuant to the Registration
Statement or otherwise in compliance with applicable federal and state securities laws). 
 (c) Certain Transactions and
Confidentiality. Other than consummating the transactions contemplated hereunder, the Purchaser has not, nor has any Person acting on behalf of or pursuant to any understanding with the Purchaser, directly or indirectly executed any purchases or
sales, including Short Sales, of the securities of the Company during the period 

  
 21 









 
commencing as of the time that the Purchaser first received a term sheet (written or oral) as of the Company or any other Person representing the Company setting forth the material terms of the
transactions contemplated hereunder and ending immediately prior to the execution hereof. Other than to other Persons party to this Agreement, the Purchaser has maintained the confidentiality of all disclosures made to it in connection with this
transaction (including the existence and terms of this transaction). Notwithstanding the foregoing, for avoidance of doubt, nothing contained herein shall constitute a representation or warranty, or preclude any actions, with respect to the
identification of the availability of, or securing of, available shares to borrow in order to effect Short Sales or similar transactions in the future. 
 (d) Beneficial Ownership. The Purchaser, together with its affiliates, will not beneficially hold or have the right to acquire greater than 19.99% of the number of shares of the Company’s
outstanding Common Stock immediately after the closing of the transactions contemplated by this Agreement. 
 ARTICLE IV.

 OTHER AGREEMENTS OF THE PARTIES 
 4.1 Integration. The Company shall not sell, offer for sale or solicit offers to buy or otherwise negotiate in respect of any security (as defined in Section 2 of the Securities Act) that
would be integrated with the offer or sale of the Securities for purposes of the rules and regulations of any Trading Market such that it would require shareholder approval prior to the closing of such other transaction unless shareholder approval
is obtained before the closing of such subsequent transaction. 
 4.2 Securities Laws Disclosure; Publicity. The Company shall on the
Trading Day immediately following the date hereof, issue a press release disclosing the material terms of the transactions contemplated hereby, and file a Current Report on Form 8-K, including the Transaction Documents as exhibits thereto, with the
Commission. The Company and the Purchaser shall consult with each other in issuing any other press releases with respect to the transactions contemplated hereby, and neither the Company nor the Purchaser shall issue any such press release nor
otherwise make any such public statement without the prior consent of the Company, with respect to any press release of the Purchaser, or without the prior consent of the Purchaser, with respect to any press release of the Company, which consent
shall not unreasonably be withheld or delayed, except if such disclosure is required by law, in which case the disclosing party shall promptly provide the other party with prior notice of such public statement or communication. 

4.3 Non-Public Information. The Purchaser hereby acknowledges that it has been provided with material non-public information concerning the
Company in connection with the sale of the Securities hereunder, including, without limitation, information regarding the material terms and conditions of the transactions contemplated by the Transaction Documents and information regarding the
Company’s financial performance since December 31, 2011. The Purchaser covenants that neither it nor any Affiliate acting on its behalf or pursuant to any understanding with it will execute any purchases or sales, including Short Sales of
any of the Company’s 

  
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securities during the period commencing with the execution of this Agreement and ending at such time that the material non-public information provided to it hereunder is made public or is no
longer material to the Company. The Purchaser also covenants that until such time as the material non-public information provided to it hereunder is made public or is no longer material to the Company, the Purchaser will maintain the confidentiality
of such information. 
 4.4 Use of Proceeds. Except as set forth on Schedule 4.4 attached hereto, the Company shall use the net proceeds
from the sale of the Securities hereunder for working capital purposes and shall not use such proceeds for: (a) the satisfaction of any portion of the Company’s debt (other than scheduled payments of principal and interest and payment of
trade payables in the ordinary course of the Company’s business and prior practices), (b) the redemption of any Common Stock or Common Stock Equivalents or (c) the settlement of any outstanding litigation. 

4.5 Indemnification of Purchaser. Subject to the provisions of this Section 4.5, the Company will indemnify and hold the Purchaser and, if
applicable, its directors, officers, shareholders, members, partners, employees and agents (and any other Persons with a functionally equivalent role of a Person holding such titles notwithstanding a lack of such title or any other title), each
Person who controls the Purchaser (within the meaning of Section 15 of the Securities Act and Section 20 of the Exchange Act), and the directors, officers, shareholders, agents, members, partners or employees (and any other Persons with a
functionally equivalent role of a Person holding such titles notwithstanding a lack of such title or any other title) of such controlling persons (each, a “Purchaser Party”) harmless from any and all losses, liabilities, obligations,
claims, contingencies, damages, costs and expenses, including all judgments, amounts paid in settlements, court costs and reasonable attorneys’ fees and costs of investigation that any such Purchaser Party may suffer or incur as a result of or
relating to (a) any breach of any of the representations, warranties, covenants or agreements made by the Company in this Agreement or in the other Transaction Documents or (b) any action instituted against the Purchaser in any capacity or
their respective Affiliates, by any stockholder of the Company who is not an Affiliate of the Purchaser, with respect to any of the transactions contemplated by the Transaction Documents (unless such action is based upon a breach of the
Purchaser’s representations, warranties or covenants under the Transaction Documents or any agreements or understandings the Purchaser may have with any such stockholder or any violations by the Purchaser of state or federal securities laws or
any conduct by the Purchaser which constitutes fraud, gross negligence, willful misconduct or malfeasance). If any action shall be brought against any Purchaser Party in respect of which indemnity may be sought pursuant to this Agreement, such
Purchaser Party shall promptly notify the Company in writing, and the Company shall have the right to assume the defense thereof with counsel of its own choosing reasonably acceptable to the Purchaser Party. Any Purchaser Party shall have the right
to employ separate counsel in any such action and participate in the defense thereof, but the fees and expenses of such counsel shall be at the expense of such Purchaser Party except to the extent that (i) the employment thereof has been
specifically authorized by the Company in writing, (ii) the Company has failed after a reasonable period of time to assume such defense and to employ counsel or (iii) in such action there is, in the reasonable opinion of counsel, a
material conflict on any material issue between the position of the Company and the position of such Purchaser Party, in which case the Company shall be responsible for the reasonable fees and expenses of no more than one such separate counsel. The
Company will not be liable to any Purchaser Party 

  
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under this Agreement (y) for any settlement by a Purchaser Party effected without the Company’s prior written consent, which shall not be unreasonably withheld or delayed; or
(z) to the extent, but only to the extent that a loss, claim, damage or liability is attributable to any Purchaser Party’s breach of any of the representations, warranties, covenants or agreements made by such Purchaser Party in this
Agreement or in the other Transaction Documents. 
 4.6 Reservation of Common Stock. As of the date hereof, the Company has reserved and
the Company shall continue to reserve and keep available at all times, free of preemptive rights, a sufficient number of shares of Common Stock for the purpose of enabling the Company to issue Shares pursuant to this Agreement. 

4.7 Listing of Common Stock. The Company hereby agrees to use best efforts to maintain the listing or quotation of the Common Stock on the NASDAQ
Capital Market, and the Company shall promptly apply for the NASDAQ Approval and promptly secure the NASDAQ Approval of the listing of the Shares on such Trading Market. The Company further agrees, if the Company applies to have the Common Stock
traded on any other Trading Market, it will then include the Shares in such application, and will take such other action as is necessary to cause the Shares to be listed or quoted on such other Trading Market as promptly as possible. The Company
will then take all action reasonably necessary to continue the listing and trading of its Common Stock on a Trading Market and will comply in all respects with the Company’s reporting, filing and other obligations under the bylaws or rules of
the Trading Market. 
 ARTICLE V. 
 MISCELLANEOUS 
 5.1 Fees and Expenses. Except as expressly set forth in the
Transaction Documents to the contrary, each party shall pay the fees and expenses of its advisers, counsel, accountants and other experts, if any, and all other expenses incurred by such party incident to the negotiation, preparation, execution,
delivery and performance of this Agreement. The Company shall pay all Transfer Agent fees, stamp taxes and other taxes and duties levied in connection with the delivery of any Securities to the Purchaser. The Placement Agent shall be paid a fee
equal to 5.0% of the purchase price plus reimbursement of its expenses up to $20,000. 
 5.2 Entire Agreement. The Transaction Documents,
together with the exhibits and schedules thereto, the Prospectus and the Prospectus Supplement, contain the entire understanding of the parties with respect to the subject matter hereof and supersede all prior agreements and understandings, oral or
written, with respect to such matters, which the parties acknowledge have been merged into such documents, exhibits and schedules. 
 5.3
Notices. Any and all notices or other communications or deliveries required or permitted to be provided hereunder shall be in writing and shall be deemed given and effective on the earliest of: (a) the date of transmission, if such notice
or communication is delivered via facsimile at the facsimile number set forth on the signature pages attached hereto prior to 5:30 p.m. (New York City time) on a Trading Day, (b) the next Trading Day after the date of transmission, if such
notice or communication is delivered via facsimile at the facsimile number 

  
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set forth on the signature pages attached hereto on a day that is not a Trading Day or later than 5:30 p.m. (New York City time) on any Trading Day, (c) the second (2nd) Trading Day
following the date of mailing, if sent by U.S. nationally recognized overnight courier service or (d) upon actual receipt by the party to whom such notice is required to be given. The address for such notices and communications shall be as
follows until such time as it may be changed by written notice delivered to the other party: 
  

	If to the Company:	EnteroMedics Inc. 

 2800 Patton
Road 
 St. Paul, MN 55113 
 Fax: 651-634-3212 
 With a copy to (which shall not constitute notice): 

Dorsey & Whitney LLP 
 50 South Sixth Street, Suite 1500 
 Minneapolis, Minnesota 55402-1498 

Attn: Kenneth L. Cutler, Esq. 
 Telephone: 612-340-2600 
 Fax: 612-340-2868 

 

	If to the Purchaser:	Kevin Douglas 

 c/o Douglas
Telecommunications, Inc. 
 125 E. Sir Francis Drake Blvd., Suite 400 

Larkspur, CA 94939 
 Fax: 415-526-2013 
 With a copy to (which shall not constitute notice): 

Davis Wright Tremaine LLP 
 505 Montgomery Street, Suite 800 
 San Francisco, California 94111 

Attn: James R. Black, Esq. 
 Telephone: 415-276-6500 
 Fax: 415-276-6599 

5.4 Amendments; Waivers. No provision of this Agreement may be waived, modified, supplemented or amended except in a written instrument signed, in
the case of an amendment, by the Company and the Purchaser or, in the case of a waiver, by the party against whom enforcement of any such waived provision is sought. No waiver of any default with respect to any provision, condition or requirement of
this Agreement shall be deemed to be a continuing waiver in the future or a waiver of any subsequent default or a waiver of any other provision, condition or requirement hereof, nor shall any delay or omission of any party to exercise any right
hereunder in any manner impair the exercise of any such right. 

  
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 5.5 Headings. The headings herein are for convenience only, do not constitute a part of this
Agreement and shall not be deemed to limit or affect any of the provisions hereof. 
 5.6 No Third-Party Beneficiaries. This Agreement is
intended for the benefit of the parties hereto and their respective successors and permitted assigns and is not for the benefit of, nor may any provision hereof be enforced by, any other Person, except as otherwise set forth in Section 4.6 and
except that the Placement Agent may rely on the representations and warranties made by each of the parties hereto. 
 5.7 Governing Law.
All questions concerning the construction, validity, enforcement and interpretation of the Transaction Documents shall be governed by and construed and enforced in accordance with the internal laws of the State of New York, without regard to the
principles of conflicts of law thereof. Each party agrees that all legal proceedings concerning the interpretations, enforcement and defense of the transactions contemplated by this Agreement and any other Transaction Documents (whether brought
against a party hereto or its respective affiliates, directors, officers, shareholders, employees or agents) shall be commenced exclusively in the state and federal courts sitting in the Borough of Manhattan, City of New York, State of New York.
Each party hereby irrevocably submits to the exclusive jurisdiction of the state and federal courts sitting in the Borough of Manhattan, City of New York, State of New York, for the adjudication of any dispute hereunder or in connection herewith or
with any transaction contemplated hereby or discussed herein (including with respect to the enforcement of any of the Transaction Documents), and hereby irrevocably waives, and agrees not to assert in any suit, action or proceeding, any claim that
it is not personally subject to the jurisdiction of any such court, that such suit, action or proceeding is improper or is an inconvenient venue for such proceeding. Each party hereby irrevocably waives personal service of process and consents to
process being served in any such suit, action or proceeding by mailing a copy thereof via registered or certified mail or overnight delivery (with evidence of delivery) to such party at the address in effect for notices to it under this Agreement
and agrees that such service shall constitute good and sufficient service of process and notice thereof. Nothing contained herein shall be deemed to limit in any way any right to serve process in any other manner permitted by law. 

5.8 Survival. The representations and warranties contained herein shall survive the Closing and the delivery of the Securities. 

5.9 Execution. This Agreement may be executed in two or more counterparts, all of which when taken together shall be considered one and the same
agreement and shall become effective when counterparts have been signed by each party and delivered to the other party, it being understood that both parties need not sign the same counterpart. In the event that any signature is delivered by
facsimile transmission or by e-mail delivery of a “.pdf” format data file, such signature shall create a valid and binding obligation of the party executing (or on whose behalf such signature is executed) with the same force and effect as
if such facsimile or “.pdf” signature page were an original thereof. 

  
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 5.10 Severability. If any term, provision, covenant or restriction of this Agreement is held by a
court of competent jurisdiction to be invalid, illegal, void or unenforceable, the remainder of the terms, provisions, covenants and restrictions set forth herein shall remain in full force and effect and shall in no way be affected, impaired or
invalidated, and the parties hereto shall use their commercially reasonable efforts to find and employ an alternative means to achieve the same or substantially the same result as that contemplated by such term, provision, covenant or restriction.
It is hereby stipulated and declared to be the intention of the parties that they would have executed the remaining terms, provisions, covenants and restrictions without including any of such that may be hereafter declared invalid, illegal, void or
unenforceable. 
 5.11 Remedies. In addition to being entitled to exercise all rights provided herein or granted by law, including
recovery of damages, the Purchaser and the Company will be entitled to specific performance under the Transaction Documents. The parties agree that monetary damages may not be adequate compensation for any loss incurred by reason of any breach of
obligations contained in the Transaction Documents and hereby agree to waive and not to assert in any action for specific performance of any such obligation the defense that a remedy at law would be adequate. 

5.12 Saturdays, Sundays, Holidays, etc. If the last or appointed day for the taking of any action or the expiration of any right required or
granted herein shall not be a Business Day, then such action may be taken or such right may be exercised on the next succeeding Business Day. 

5.13 Construction. The parties agree that each of them and/or their respective counsel has reviewed and had an opportunity to revise the
Transaction Documents and, therefore, the normal rule of construction to the effect that any ambiguities are to be resolved against the drafting party shall not be employed in the interpretation of the Transaction Documents or any amendments hereto.
In addition, each and every reference to share prices and shares of Common Stock in any Transaction Document shall be subject to adjustment for reverse and forward stock splits, stock dividends, stock combinations and other similar transactions of
the Common Stock that occur after the date of this Agreement. 
 5.14 WAIVER OF JURY TRIAL. IN ANY ACTION, SUIT, OR PROCEEDING IN ANY
JURISDICTION BROUGHT BY ANY PARTY AGAINST ANY OTHER PARTY, THE PARTIES EACH KNOWINGLY AND INTENTIONALLY, TO THE GREATEST EXTENT PERMITTED BY APPLICABLE LAW, HEREBY ABSOLUTELY, UNCONDITIONALLY, IRREVOCABLY AND EXPRESSLY WAIVE TRIAL BY JURY.

 (Signature Page Follows) 

  
 27 









 IN WITNESS WHEREOF, the parties hereto have caused this Securities Purchase Agreement to be duly executed by
their respective authorized signatories as of the date first indicated above. 
 ENTEROMEDICS INC. 

 

			
	By:	 	/s/ Mark B. Knudson
		 	 Name: Mark B. Knudson

Title: President and CEO


 PURCHASER: 
 K&M Douglas Trust 
  

			
	By:	 	/s/ Kevin Douglas
		 	 Name: Kevin Douglas
 Title:
Trustee


 Douglas Irrevocable Descendant’s Trust 

 

			
	By:	 	/s/ Kevin Douglas
		 	 Name: Kevin Douglas
 Title:
Trustee


 Douglas Family Trust 
  

			
	By:	 	/s/ James Douglas, Jr.
		 	 Name: James Douglas, Jr.

Title: Trustee









 SCHEDULE A 

 

			
	Purchaser	  	Percentage of Shares
	 K&M Douglas Trust
	  	50%
	 Douglas Irrevocable Descendant’s Trust
	  	30%
	 Douglas Family Trust
	  	20%