Document:

Certificate of Designation of Series B Convertible Preferred Stock

 EXHIBIT 4.8 
 CERTIFICATE OF DESIGNATION 
 OF 

SERIES B CONVERTIBLE PREFERRED STOCK 
 OF 
 BIODEL INC. 

PURSUANT TO SECTION 151 OF THE 
 DELAWARE GENERAL CORPORATION LAW 
 BIODEL INC., a Delaware corporation (the
“Corporation”), in accordance with the provisions of Section 103 of the Delaware General Corporation Law (the “DGCL”) does hereby certify that, in accordance with Sections 141(c) and 151 of the DGCL, the
following resolution was duly adopted by a duly authorized committee of the Board of Directors of the Corporation by the unanimous written consent of that committee duly effected on June 21, 2012: 

RESOLVED, that pursuant to the authority granted to and vested in the Board of Directors of the Corporation in accordance with the
provisions of the Second Amended and Restated Certificate of Incorporation of the Corporation, as amended (the “Certificate of Incorporation”), there is hereby established a series of the Corporation’s authorized
Preferred Stock, par value $.01 per share, which series shall be designated as the Series B Convertible Preferred Stock, par value $.01 per share, of the Corporation, with the designation, number of shares, powers, preferences, rights,
qualifications, limitations and restrictions thereof (in addition to any provisions set forth in the Certificate of Incorporation of the Corporation which are applicable to the Preferred Stock of all classes and series) as follows: 

SERIES B CONVERTIBLE PREFERRED STOCK 
 SECTION 1. DEFINITIONS. For the purposes hereof, the following terms shall have the following meanings: 
 “Affiliate” means any person or entity that, directly or indirectly through one or more intermediaries, controls or is controlled by or is under common control with a person or
entity, as such terms are used in and construed under Rule 144 under the Securities Act. With respect to a Holder, any investment fund or managed account that is managed on a discretionary basis by the same investment manager as such Holder
will be deemed to be an Affiliate of such Holder. 
 “Alternate Consideration” shall have the meaning
set forth in Section 7(b). 

 “Business Day” means any day except Saturday, Sunday, any day which
shall be a federal legal holiday in the United States or any day on which banking institutions in the State of New York are authorized or required by law or other governmental action to close. 

“Buy-In” shall have the meaning set forth in Section 6(d)(iii). 

“Closing Sale Price” means, for any security as of any date, the last closing trade price for such security prior
to 4:00 p.m., New York City time, on the principal securities exchange or trading market where such security is listed or traded, as reported by Bloomberg, L.P. (or an equivalent, reliable reporting service mutually acceptable to and hereafter
designated by Holders of a majority of the then-outstanding Series B Preferred Stock and the Corporation), or if the foregoing do not apply, the last trade price of such security in the over-the-counter market on the electronic bulletin board
for such security as reported by Bloomberg, L.P., or, if no last trade price is reported for such security by Bloomberg, L.P., the average of the bid prices of any market makers for such security as reported on the OTC Pink Market by OTC Markets
Group, Inc. If the Closing Sale Price cannot be calculated for a security on a particular date on any of the foregoing bases, the Closing Sale Price of such security on such date shall be the fair market value as determined in good faith by the
Board of Directors of the Corporation. 
 “Commission” means the Securities and Exchange Commission.

 “Common Stock” means the Corporation’s Common Stock, par value $.01 per share, and stock of any
other class of securities into which such securities may hereafter be reclassified or changed into. 
 “Conversion
Date” shall have the meaning set forth in Section 6(a). 
 “Conversion Price” shall
mean $2.36, as adjusted pursuant to paragraph 7 hereof. 
 “Conversion Ratio” shall have the meaning set
forth in Section 6(b). 
 “Conversion Shares” means, collectively, the shares of Common Stock
issuable upon conversion of the shares of Series B Preferred Stock in accordance with the terms hereof. 

“Daily Failure Amount” means the product of (x) .005 multiplied by (y) the Closing Sale Price of the
Common Stock on the applicable Share Delivery Date. 
 “DGCL” shall mean the Delaware General
Corporation Law. 
 “Distribution” shall have the meaning set forth in Section 7(b). 

  
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 “DWAC Delivery” shall have the meaning set forth in
Section 6(a). 
 “Exchange Act” means the Securities Exchange Act of 1934, as amended, and the
rules and regulations promulgated thereunder. 
 “Fundamental Transaction” shall have the meaning set
forth in Section 7(c). 
 “Holder” means any holder of Series B Preferred Stock. 

“Junior Securities” shall have the meaning set forth in Section 5(a). 

“Notice of Conversion” shall have the meaning set forth in Section 6(a). 

“Parity Securities” shall have the meaning set forth in Section 5(a). 

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

“Senior Securities” shall have the meaning set forth in Section 5(a). 

“Series B Preferred Stock Register” shall have the meaning set forth in Section 2(b). 

“Share Delivery Date” shall have the meaning set forth in Section 6(d). 

“Stated Value” shall mean $2.36. 
 “Trading Day” means a day on which the Common Sock is traded for any period on the principal securities exchange or if the Common Stock is not traded on a principal securities
exchange, on a day that the Common Stock is traded on another securities market on which the Common Stock is then being traded. 

SECTION 2. DESIGNATION, AMOUNT AND PAR VALUE; ASSIGNMENT. 

(a) The series of preferred stock designated by this Certificate shall be designated as the Corporation’s “Series B
Convertible Preferred Stock” (the “Series B Preferred Stock”) and the number of shares so designated shall be 4,000,000. Each share of Series B Preferred Stock shall have a par value of $.01 per share.

  
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 (b) The Corporation shall register shares of the Series B Preferred Stock, upon records
to be maintained by the Corporation for that purpose (the “Series B Preferred Stock Register”), in the name of the Holders thereof from time to time. The Corporation may deem and treat the registered Holder of shares of
Series B Preferred Stock as the absolute owner thereof for the purpose of any conversion thereof and for all other purposes. The Corporation shall register, or cause the Corporation’s transfer agent to register, the transfer of any shares
of Series B Preferred Stock in the Series B Preferred Stock Register, upon surrender of the certificates evidencing such shares to be transferred, duly endorsed by the Holder thereof, to the Corporation at its principal place of business.
Upon any such registration or transfer, a new certificate evidencing the shares of Series B Preferred Stock so transferred shall be issued to the transferee and a new certificate evidencing the remaining portion of the shares not so
transferred, if any, shall be issued to the transferring Holder, in each case, within three Business Days. The provisions of this Certificate are intended to be for the benefit of all Holders from time to time and shall be enforceable by any such
Holder. 
 SECTION 3. DIVIDENDS. Holders shall be entitled to receive, and the Corporation shall pay, dividends on
shares of the Series B Preferred Stock equal (on an as-if-converted-to-Common-Stock basis) to and in the same form as dividends (other than dividends in the form of Common Stock) actually paid on shares of the Common Stock when, as and if such
dividends (other than dividends in the form of Common Stock) are paid on shares of the Common Stock. 
 SECTION 4. VOTING
RIGHTS. Except as otherwise provided herein or as otherwise required by the DGCL, the Series B Preferred Stock shall have no voting rights. However, as long as any shares of Series B Preferred Stock are outstanding, the
Corporation shall not, without the affirmative vote of the Holders of a majority of the then outstanding shares of the Series B Preferred Stock, (a) alter or change adversely the powers, preferences or rights given to the Series B
Preferred Stock or alter or amend this Certificate of Designation, (b) increase the number of authorized shares of Series B Preferred Stock, or (c) enter into any agreement with respect to any of the foregoing. 

SECTION 5. RANK; LIQUIDATION. 
 (a) The Series B Preferred Stock shall rank (i) senior to all of the Common Stock; (ii) senior to any class or series of capital stock of the Corporation hereafter created specifically
ranking by its terms junior to any Series B Preferred Stock (“Junior Securities”); (iii) on parity with the Corporation’s Series A Convertible Preferred Stock, $0.01 par value per share (the
“Series A Preferred Stock”) and with any class or series of capital stock of the Corporation hereafter created specifically ranking by its terms on parity with the Series B Preferred Stock (“Parity
Securities”); and (iv) junior to any class or series of capital stock of the Corporation 

  
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hereafter created specifically ranking by its terms senior to any Series B Preferred Stock (“Senior Securities”), in each case, as to dividends, distributions of
assets upon liquidation, dissolution or winding up of the Corporation, whether voluntarily or involuntarily. 
 (b) Subject to
the prior and superior rights of the holders of any Senior Securities of the Corporation, upon liquidation, dissolution or winding up of the Corporation, whether voluntary or involuntary (each, a “Liquidation Event”), each
holder of shares of Series B Preferred Stock shall be entitled to receive, in preference to any distributions of any of the assets or surplus funds of the Corporation to the holders of the Common Stock and Junior Securities and pari passu with
any distribution to the holders of Parity Securities, an amount equal to $.01 per share of Series B Preferred Stock, plus an additional amount equal to any dividends declared but unpaid on such shares, before any payments shall be made or any
assets distributed to holders of any class of Common Stock or Junior Securities. If, upon any such Liquidation Event, the assets of the Corporation shall be insufficient to pay the holders of shares of the Series B Preferred Stock the amount
required under the preceding sentence, then all remaining assets of the Corporation shall be distributed ratably to holders of the shares of the Series B Preferred Stock and Parity Securities. 

(c) After payment to the holders of shares of the Series B Preferred Stock of the amount required under Section 5(b) and
subject to the prior and superior rights of the holders of any Senior Securities of the Corporation, the remaining assets or surplus funds of the Corporation, if any, available for distribution to stockholders shall be distributed ratably among the
holders of the Series A Preferred Stock, the Series B Preferred Stock, any other class or series of capital stock that participates with the Common Stock in the distribution of assets upon any Liquidation Event and the Common Stock, with the
holders of the Series B Preferred Stock deemed to hold that number of shares of Common Stock into which such shares of Series B Preferred Stock are then convertible (without giving effect for such purposes to any limitations on the
beneficial ownership of Series B Preferred Stock to which any holders are subject). 
 SECTION 6.
CONVERSION. 
 (a) Conversions at Option of Holder. Each share of Series B Preferred Stock shall be
convertible, at any time and from time to time from and after the date of the issuance thereof, at the option of the Holder thereof, into a number of shares of Common Stock equal to the Conversion Ratio in effect at the time of such conversion.
Holders shall effect conversions by providing the Corporation with the form of conversion notice (via overnight courier, facsimile or email) attached hereto as Annex A (a “Notice of Conversion”), duly completed
and executed. For purposes of clarification, unless required pursuant to industry standard stock transfer procedures, the Corporation’s transfer agent shall not require a Holder to obtain a medallion

  
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guaranty, notary attestation or any similar deliverable in order to effectuate the conversion of all or a portion of such Holder’s shares of Series B Preferred Stock. Other than a conversion
following a Fundamental Transaction or following a notice provided for under Section 7(d)(ii) hereof, the Notice of Conversion must specify at least a number of shares of Series B Preferred Stock to be converted equal to the lesser of
(x) 100 shares (such number subject to appropriate adjustment following the occurrence of an event specified in Section 7(a) hereof) and (y) the number of shares of Series B Preferred Stock then held by the Holder. Provided the
Corporation’s transfer agent is participating in the Depository Trust Company (“DTC”) Fast Automated Securities Transfer program, the Notice of Conversion may specify, at the Holder’s election, whether the
applicable Conversion Shares shall be credited to the account of the Holder’s prime broker with DTC through its Deposit Withdrawal Agent Commission system (a “DWAC Delivery”). The “Conversion
Date”, or the date on which a conversion shall be deemed effective, shall be defined as the Trading Day that the Notice of Conversion, completed and executed, is sent by facsimile to, and received during regular business hours by, the
Corporation; provided that the original certificate(s) representing such shares of Series B Preferred Stock being converted, duly endorsed, and the accompanying Notice of Conversion, are received by the Corporation within two (2) Trading
Days thereafter. In all other cases, the Conversion Date shall be defined as the Trading Day on which the original stock certificates representing the shares of Series B Preferred Stock being converted, duly endorsed, and the accompanying
Notice of Conversion, are received by the Corporation. The calculations set forth in the Notice of Conversion shall control in the absence of manifest or mathematical error. 
 (b) Conversion Ratio. The “Conversion Ratio” for each share of Series B Preferred Stock shall be equal to the Stated Value divided by the Conversion Price. 

(c) [INTENTIONALLY OMITTED] 
 (d) Mechanics of Conversion 
 (i) Delivery of Certificate or Electronic
Issuance Upon Conversion. Not later than three Trading Days after the applicable Conversion Date, or if the Holder requests the issuance of physical certificate(s), two Trading Days after receipt by the Corporation of the original certificate(s)
representing such shares of Series B Preferred Stock being converted, duly endorsed, and the accompanying Notice of Conversion (the “Share Delivery Date”), the Corporation shall (a) deliver, or cause to be
delivered, to the converting Holder a physical certificate or certificates representing the number of Conversion Shares being acquired upon the conversion of shares of Series B Preferred Stock (which certificate or certificates shall not have
any legends on it) or (b) in the case of a DWAC Delivery, electronically transfer such Conversion Shares by crediting the account of the Holder’s prime broker with DTC through its 

  
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DWAC system. If in the case of any Notice of Conversion such certificate or certificates are not delivered to or as directed by or, in the case of a DWAC Delivery, such shares are not
electronically delivered to or as directed by, the applicable Holder by the Share Delivery Date, the applicable Holder shall be entitled to elect to rescind such Conversion Notice by written notice to the Corporation at any time on or before its
receipt of such certificate or certificates for Conversion Shares or electronic receipt of such shares, as applicable, in which event the Corporation shall promptly return to such Holder any original Series B Preferred Stock certificate
delivered to the Corporation and such Holder shall promptly return to the Corporation any Common Stock certificates or otherwise direct the return of any shares of Common Stock delivered to the Holder through the DWAC system, representing the shares
of Series B Preferred Stock unsuccessfully tendered for conversion to the Corporation. 
 (ii) Obligation Absolute.
Subject to any limitations on the beneficial ownership of Series B Preferred Stock to which a Holder may be subject and subject to such Holder’s right to rescind a Conversion Notice pursuant to Section 6(d)(i) above, the Corporation’s
obligation to issue and deliver the Conversion Shares upon conversion of Series B Preferred Stock in accordance with the terms hereof are absolute and unconditional, irrespective of any action or inaction by a Holder to enforce the same, any
waiver or consent with respect to any provision hereof, the recovery of any judgment against any Person or any action to enforce the same, or any setoff, counterclaim, recoupment, limitation or termination, or any breach or alleged breach by such
Holder or any other Person of any obligation to the Corporation or any violation or alleged violation of law by such Holder or any other Person, and irrespective of any other circumstance which might otherwise limit such obligation of the
Corporation to such Holder in connection with the issuance of such Conversion Shares. Subject to any limitations on the beneficial of ownership of Series B Preferred Stock to which a Holder may be subject and subject to such Holder’s right to
rescind a Conversion Notice pursuant to Section 6(d)(i) above, in the event a Holder shall elect to convert any or all of its Series B Preferred Stock, the Corporation may not refuse conversion based on any claim that such Holder or any
one associated or affiliated with such Holder has been engaged in any violation of law, agreement or for any other reason, unless an injunction from a court, on notice to such Holder, restraining and/or enjoining conversion of all or part of the
Series B Preferred Stock of such Holder shall have been sought and obtained by the Corporation, and the Corporation posts a surety bond for the benefit of such Holder in the amount of 150% of the value of the Conversion Shares into which would
be converted the Series B Preferred Stock which is subject to such injunction, which bond shall remain in effect until the completion of arbitration/litigation of the underlying dispute and the proceeds of which shall be payable to such Holder
to the extent it obtains judgment. In the absence of such injunction, the Corporation shall, subject to any limitations on the beneficial ownership of Series B Preferred Stock to which a Holder may be subject and subject to such Holder’s right
to rescind a Conversion Notice pursuant to Section 6(d)(i) above, 

  
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issue Conversion Shares upon a properly noticed conversion. If the Corporation fails to deliver to a Holder such certificate or certificates, or electronically deliver (or cause its transfer
agent to electronically deliver) such shares in the case of a DWAC Delivery, pursuant to Section 6(d)(i) on or prior to the third (3rd) Trading Day after the Share Delivery Date applicable to such conversion (other than a failure caused by
incorrect or incomplete information provided by such Holder to the Corporation), then, unless the Holder has rescinded the applicable Conversion Notice pursuant to Section 6(d)(i) above, the Corporation shall pay (as liquidated damages and not
as a penalty) to such Holder an amount payable in cash equal to the product of (x) the number of Conversion Shares required to have been issued by the Corporation on such Share Delivery Date, (y) an amount equal to the Daily Failure Amount
and (z) the number of Trading Days actually lapsed after such third (3rd) Trading Day after the Share Delivery Date during which such certificates have not been delivered, or, in the case of a DWAC Delivery, such shares have not been
electronically delivered; provided, however, the Holder shall only receive up to such amount of shares of Common Stock such that Holder and any other persons or entities whose beneficial ownership of Common Stock would be aggregated with the
Holder’s for purposes of Section 13(d) of the Exchange Act (including shares held by any “group” of which the Holder is a member, but excluding shares beneficially owned by virtue of the ownership of securities or rights to
acquire securities that have limitations on the right to convert, exercise or purchase similar to the limitation set forth herein) shall not collectively beneficially own greater than the percentage of the total number of shares of Common Stock of
the Corporation then issued and outstanding applicable to any limitation on beneficial ownership to which such Holder may be subject. Nothing herein shall limit a Holder’s right to pursue actual damages for the Corporation’s failure to
deliver Conversion Shares within the period specified herein and such Holder shall have the right to pursue all remedies available to it hereunder, at law or in equity including, without limitation, a decree of specific performance and/or injunctive
relief; provided that Holder shall not receive duplicate damages for the Corporation’s failure to deliver Conversion Shares within the period specified herein. The exercise of any such rights shall not prohibit a Holder from seeking to enforce
damages pursuant to any other Section hereof or under applicable law. 
 (iii) Compensation for Buy-In on Failure to Timely
Deliver Certificates Upon Conversion. If the Corporation fails to deliver to a Holder the applicable certificate or certificates or to effect a DWAC Delivery, as applicable, by the Share Delivery Date pursuant to Section 6(d)(i) (other than
a failure caused by incorrect or incomplete information provided by such Holder to the Corporation), and if after such Share Delivery Date such Holder is required by its brokerage firm to purchase (in an open market transaction or otherwise), or the
Holder’s brokerage firm otherwise purchases, shares of Common Stock to deliver in satisfaction of a sale by such Holder of the Conversion Shares which such Holder was entitled to receive upon the conversion relating to such Share Delivery Date
(a “Buy-In”), then the Corporation shall (A) pay 

  
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in cash to such Holder (in addition to any other remedies available to or elected by such Holder) the amount by which (x) such Holder’s total purchase price (including any brokerage
commissions) for the shares of Common Stock so purchased exceeds (y) the product of (1) the aggregate number of shares of Common Stock that such Holder was entitled to receive from the conversion at issue multiplied by (2) the actual
sale price at which the sell order giving rise to such purchase obligation was executed (including any brokerage commissions) and (B) at the option of such Holder, either reissue (if surrendered) the shares of Series B Preferred Stock
equal to the number of shares of Series B Preferred Stock submitted for conversion or deliver to such Holder the number of shares of Common Stock that would have been issued if the Corporation had timely complied with its delivery requirements
under Section 6(d)(i). For example, if a Holder purchases shares of Common Stock having a total purchase price of $11,000 to cover a Buy-In with respect to an attempted conversion of shares of Series B Preferred Stock with respect to which
the actual sale price (including any brokerage commissions) giving rise to such purchase obligation was a total of $10,000 under clause (A) of the immediately preceding sentence, the Corporation shall be required to pay such Holder $1,000. The
Holder shall provide the Corporation written notice, within three (3) Trading Days after the occurrence of a Buy-In, indicating the amounts payable to such Holder in respect of such Buy-In together with applicable confirmations and other
evidence reasonably requested by the Corporation. Nothing herein shall limit a Holder’s right to pursue any other remedies available to it hereunder, at law or in equity including, without limitation, a decree of specific performance and/or
injunctive relief with respect to the Corporation’s failure to timely deliver certificates representing shares of Common Stock upon conversion of the shares of Series B Preferred Stock as required pursuant to the terms hereof; provided,
however, that the Holder shall not be entitled to both (i) require the reissuance of the shares of Series B Preferred Stock submitted for conversion for which such conversion was not timely honored and (ii) receive the number of
shares of Common Stock that would have been issued if the Corporation had timely complied with its delivery requirements under Section 6(d)(i). 
 (iv) Reservation of Shares Issuable Upon Conversion. The Corporation covenants that it will at all times reserve and keep available out of its authorized and unissued shares of Common Stock for the
sole purpose of issuance upon conversion of the Series B Preferred Stock, free from preemptive rights or any other actual contingent purchase rights of Persons other than the Holders of the Series B Preferred Stock, not less than such
aggregate number of shares of the Common Stock as shall be issuable (taking into account the adjustments of Section 7) upon the conversion of all outstanding shares of Series B Preferred Stock. The Corporation covenants that all shares of
Common Stock that shall be so issuable shall, upon issue, be duly authorized, validly issued, fully paid and nonassessable. 

  
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 (v) Fractional Shares. No fractional shares or scrip representing fractional shares
of Common Stock shall be issued upon the conversion of the Series B Preferred Stock. As to any fraction of a share which a Holder would otherwise be entitled to receive upon such conversion, the Corporation shall at its election, either pay a
cash adjustment in respect of such final fraction in an amount equal to such fraction multiplied by the Conversion Price or round up to the next whole share. 
 (vi) Transfer Taxes. The issuance of certificates for shares of the Common Stock upon conversion of the Series B Preferred Stock shall be made without charge to any Holder for any documentary
stamp or similar taxes that may be payable in respect of the issue or delivery of such certificates, provided that the Corporation shall not be required to pay any tax that may be payable in respect of any transfer involved in the issuance and
delivery of any such certificate upon conversion in a name other than that of the registered Holder(s) of such shares of Series B Preferred Stock and the Corporation shall not be required to issue or deliver such certificates unless or until
the Person or Persons requesting the issuance thereof shall have paid to the Corporation the amount of such tax or shall have established to the satisfaction of the Corporation that such tax has been paid. 

(e) Status as Stockholder. Upon each Conversion Date, (i) the shares of Series B Preferred Stock being converted shall
be deemed converted into shares of Common Stock and (ii) the Holder’s rights as a holder of such converted shares of Series B Preferred Stock shall cease and terminate, excepting only the right to receive certificates for such shares
of Common Stock and to any remedies provided herein or otherwise available at law or in equity to such Holder because of a failure by the Corporation to comply with the terms of this Certificate of Designation. In all cases, the holder shall retain
all of its rights and remedies for the Corporation’s failure to convert Series B Preferred Stock. 
 SECTION 7.
CERTAIN ADJUSTMENTS. 
 (a) Stock Dividends and Stock Splits. If the Corporation, at any time while the
Series B Preferred Stock is outstanding: (A) pays a stock dividend or otherwise makes a distribution or distributions payable in shares of Common Stock (which, for avoidance of doubt, shall not include any shares of Common Stock issued by
the Corporation upon conversion of shares of Series B Preferred Stock) with respect to the then outstanding shares of Common Stock; (B) subdivides outstanding shares of Common Stock into a larger number of shares; or (C) combines
(including by way of a reverse stock split) outstanding shares of Common Stock into a smaller number of shares, then the Conversion Price shall be multiplied by a fraction of which the numerator shall be the number of shares of Common Stock
(excluding any treasury shares of the Corporation) outstanding immediately before such event and of which the 

  
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denominator shall be the number of shares of Common Stock outstanding immediately after such event (excluding any treasury shares of the Corporation). Any adjustment made pursuant to this
Section 7(a) shall become effective immediately after the record date for the determination of stockholders entitled to receive such dividend or distribution and shall become effective immediately after the effective date in the case of a
subdivision or combination. 
 (b) Rights Upon Distribution of Assets. If the Company shall declare or make any dividend
or other distribution of its assets (or rights to acquire its assets) to holders of shares of Common Stock, by way of return of capital or otherwise (including, without limitation, any distribution of cash, stock or other securities, property or
options by way of a dividend, spin off, reclassification, corporate rearrangement, scheme of arrangement or other similar transaction) (a “Distribution”), a Holder shall be entitled to receive the dividend or distribution of assets
that would have been payable to such Holder pursuant to the Distribution had such Holder converted his or her shares of Series B Preferred Stock (or, if he or she had partially converted such shares prior to the Distribution, any unconverted portion
thereof) immediately prior to such record date. 
 (c) Fundamental Transaction. If, at any time while the Series B
Preferred Stock is outstanding, (A) the Corporation effects any merger or consolidation of the Corporation with or into another Person (other than a merger in which the Corporation is the surviving or continuing entity and its Common Stock is
not exchanged for or converted into other securities, cash or property), (B) the Corporation effects any sale of all or substantially all of its assets in one transaction or a series of related transactions, (C) any tender offer or
exchange offer (whether by the Corporation or another Person) is completed pursuant to which all of the Common Stock is exchanged for or converted into other securities, cash or property, or (D) the Corporation effects any reclassification of
the Common Stock or any compulsory share exchange pursuant (other than as a result of a dividend, subdivision or combination covered by Section 7(a) above) to which the Common Stock is effectively converted into or exchanged for other
securities, cash or property (in any such case, a “Fundamental Transaction”), then, upon any subsequent conversion of this Series B Preferred Stock the Holders shall have the right to receive, in lieu of the right to
receive Conversion Shares, for each Conversion Share that would have been issuable upon such conversion immediately prior to the occurrence of such Fundamental Transaction, the same kind and amount of securities, cash or property as it would have
been entitled to receive upon the occurrence of such Fundamental Transaction if it had been, immediately prior to such Fundamental Transaction, the holder of one share of Common Stock (the “Alternate Consideration”). For
purposes of any such subsequent conversion, the determination of the Conversion Ratio shall be appropriately adjusted to apply to such Alternate Consideration based on the amount of Alternate Consideration issuable in respect of one share of Common
Stock in such Fundamental Transaction, and the Corporation shall adjust the Conversion Ratio in a reasonable manner reflecting the relative value of any different components of the Alternate 

  
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Consideration. If holders of Common Stock are given any choice as to the securities, cash or property to be received in a Fundamental Transaction, then the Holders shall be given the same choice
as to the Alternate Consideration it receives upon any conversion of this Series B Preferred Stock following such Fundamental Transaction. To the extent necessary to effectuate the foregoing provisions, any successor to the Corporation or
surviving entity in such Fundamental Transaction shall file a new Certificate of Designation with the same terms and conditions and issue to the Holders new preferred stock consistent with the foregoing provisions and evidencing the Holders’
right to convert such preferred stock into Alternate Consideration. The terms of any agreement to which the Corporation is a party and pursuant to which a Fundamental Transaction is effected shall include terms requiring any such successor or
surviving entity to comply with the provisions of this Section 7(b) and ensuring that the Series B Preferred Stock (or any such replacement security) will be similarly adjusted upon any subsequent transaction analogous to a Fundamental
Transaction. The Corporation shall cause to be delivered to each Holder, at its last address as it shall appear upon the stock books of the Corporation, written notice of any Fundamental Transaction at least 20 calendar days prior to the date on
which such Fundamental Transaction is expected to become effective or close. 
 (d) Calculations. All calculations under
this Section 7 shall be made to the nearest cent or the nearest 1/100th of a share, as the case may be. For purposes of this Section 7, the number of shares of Common Stock deemed to be issued and outstanding as of a given date shall be
the sum of the number of shares of Common Stock (excluding any treasury shares of the Corporation) issued and outstanding. 

(e) Notice to the Holders. 
 (i) Adjustment to Conversion Price. Whenever the Conversion Price is adjusted pursuant to any provision of this Section 7, the Corporation shall promptly deliver to each Holder a notice
setting forth the Conversion Ratio after such adjustment and setting forth a brief statement of the facts requiring such adjustment. 
 (ii) Other Notices. If (A) the Corporation shall declare a dividend (or any other distribution in whatever form) on the Common Stock, (B) the Corporation shall declare a special
nonrecurring cash dividend on or a redemption of the Common Stock, (C) the Corporation shall authorize the granting to all holders of the Common Stock of rights or warrants to subscribe for or purchase any shares of capital stock of any class
or of any rights, (D) the approval of any stockholders of the Corporation shall be required in connection with any reclassification of the Common Stock, any consolidation or merger to which the Corporation is a party, any sale or transfer of
all or substantially all of the assets of the Corporation, of any compulsory share exchange whereby the Common Stock is converted into other securities, cash 

  
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or property or (E) the Corporation shall authorize the voluntary or involuntary dissolution, liquidation or winding up of the affairs of the Corporation, then, in each case, the Corporation
shall cause to be filed at each office or agency maintained for the purpose of conversion of this Series B Preferred Stock, and shall cause to be delivered to each Holder at its last address as it shall appear upon the stock books of the
Corporation, at least 20 calendar days prior to the applicable record or effective date hereinafter specified, a notice stating (x) the date on which a record is to be taken for the purpose of such dividend, distribution, redemption, rights or
warrants, or if a record is not to be taken, the date as of which the holders of the Common Stock of record to be entitled to such dividend, distributions, redemption, rights or warrants are to be determined or (y) the date on which such
reclassification, consolidation, merger, sale, transfer or share exchange is expected to become effective or close, and the date as of which it is expected that holders of the Common Stock of record shall be entitled to exchange their shares of the
Common Stock for securities, cash or other property deliverable upon such reclassification, consolidation, merger, sale, transfer or share exchange, provided that the failure to deliver such notice or any defect therein or in the delivery thereof
shall not affect the validity of the corporate action required to be specified in such notice. 
 SECTION 8.
MISCELLANEOUS. 
 (a) Notices. Any and all notices or other communications or deliveries to be provided by
the Holders hereunder including, without limitation, any Notice of Conversion, shall be in writing and delivered personally, by email, facsimile, or sent by a nationally recognized overnight courier service, addressed to the Corporation, at 100 Saw
Mill Road, Danbury, Connecticut 06810, facsimile number (203) 796-5002, or such other facsimile number or address as the Corporation may specify for such purposes by notice to the Holders delivered in accordance with this Section. Any and all
notices or other communications or deliveries to be provided by the Corporation hereunder shall be in writing and delivered personally, by facsimile, or sent by a nationally recognized overnight courier service addressed to each Holder at the
facsimile number or address of such Holder appearing on the books of the Corporation, or if no such facsimile number or address appears on the books of the Corporation, at the principal place of business of such Holder. Any notice or other
communication or deliveries hereunder shall be deemed given and effective on the earliest of (i) the date of transmission, if such notice or communication is delivered via facsimile at the facsimile number specified in this Section prior to
5:30 p.m. (New York City time) on any date, (ii) the date immediately following the date of transmission, if such notice or communication is delivered via facsimile at the facsimile number specified in this Section between 5:30 p.m. and
11:59 p.m. (New York City time) on any date, (iii) the second Business Day following the date of mailing, if sent by nationally recognized overnight courier service, or (iv) upon actual receipt by the party to whom such notice is
required to be given. 

  
 13 

 (b) Lost or Mutilated Series B Preferred Stock Certificate. If a Holder’s
Series B Preferred Stock certificate shall be mutilated, lost, stolen or destroyed, the Corporation shall execute and deliver, in exchange and substitution for and upon cancellation of a mutilated certificate, or in lieu of or in substitution
for a lost, stolen or destroyed certificate, a new certificate for the shares of Series B Preferred Stock so mutilated, lost, stolen or destroyed, but only upon receipt of evidence of such loss, theft or destruction of such certificate, and of
the ownership thereof, reasonably satisfactory to the Corporation and, in each case, customary and reasonable indemnity, if requested. Applicants for a new certificate under such circumstances shall also comply with such other reasonable regulations
and procedures and pay such other reasonable third-party costs as the Corporation may prescribe. 
 (c) Waiver. Any
waiver by the Corporation or a Holder of a breach of any provision of this Certificate of Designation shall not operate as or be construed to be a waiver of any other breach of such provision or of any breach of any other provision of this
Certificate of Designation or a waiver by any other Holders. The failure of the Corporation or a Holder to insist upon strict adherence to any term of this Certificate of Designation on one or more occasions shall not be considered a waiver or
deprive that party (or any other Holder) of the right thereafter to insist upon strict adherence to that term or any other term of this Certificate of Designation. Any waiver by the Corporation or a Holder must be in writing. 

(d) Severability. If any provision of this Certificate of Designation is invalid, illegal or unenforceable, the balance of this
Certificate of Designation shall remain in effect, and if any provision is inapplicable to any Person or circumstance, it shall nevertheless remain applicable to all other Persons and circumstances. If it shall be found that any interest or other
amount deemed interest due hereunder violates the applicable law governing usury, the applicable rate of interest due hereunder shall automatically be lowered to equal the maximum rate of interest permitted under applicable law. 

(e) Next Business or Trading Day. Whenever any payment or other obligation hereunder shall be due on a day other than a Business
Day or a Trading Day, such payment shall be made on the next succeeding Business Day or Trading Day, as the case may be. 
 (f)
Headings. The headings contained herein are for convenience only, do not constitute a part of this Certificate of Designation and shall not be deemed to limit or affect any of the provisions hereof. 

(g) Status of Converted Series B Preferred Stock. If any shares of Series B Preferred Stock shall be converted or
reacquired by the Corporation, such shares shall resume the status of authorized but unissued shares of preferred stock and shall no longer be designated as Series B Preferred Stock. 

  
 14 

 IN WITNESS WHEREOF, the Corporation has caused this Certificate of Designation to be
signed by its duly authorized officer this 26th day of June 2012. 
 BIODEL INC. 

By: /s/ Errol De Souza             

      Name: Errol De Souza 

      Title: President and CEO 

 ANNEX A 
 NOTICE OF CONVERSION 
 (TO BE EXECUTED BY THE REGISTERED HOLDER IN ORDER TO CONVERT
SHARES OF SERIES A PREFERRED STOCK) 
 The undersigned Holder hereby irrevocably elects to convert the number of shares of Series B
Convertible Preferred Stock indicated below, represented by stock certificate No(s). _______________ (the “Preferred Stock Certificates”), into shares of common stock, par value $0.01 per share (the “Common Stock”),
of Biodel Inc., a Delaware corporation (the “Corporation”), as of the date written below. If securities are to be issued in the name of a person other than the undersigned, the undersigned will pay all transfer taxes payable with
respect thereto. Capitalized terms utilized but not defined herein shall have the meaning ascribed to such terms in that certain Certificate of Designation of Preferences, Rights and Limitations of Series B Convertible Preferred Stock (the
“Certificate of Designation”) filed by the Corporation on June 26, 2012. 
 [INCLUDE THIS PARAGRAPH IF APPLICABLE.]

 As of the date hereof, the number of shares of Common Stock beneficially owned by the undersigned Holder (together with such Holder’s
Affiliates, and any other Person whose beneficial ownership of Common Stock would be aggregated with the Holder’s for purposes of Section 13(d) of the Exchange Act and the applicable regulations of the Commission, including any
“group” of which the Holder is a member), including the number of shares of Common Stock issuable upon conversion of the Series B Preferred Stock subject to this Notice of Conversion, but excluding the number of shares of Common Stock
which are issuable upon (A) conversion of the remaining, unconverted Series B Preferred Stock beneficially owned by such Holder or any of its Affiliates, and (B) exercise or conversion of the unexercised or unconverted portion of any
other securities of the Corporation (including any warrants) beneficially owned by such Holder or any of its Affiliates that are subject to any limitations on the beneficial ownership of the Corporation’s capital stock to which a Holder may be
subject, is _______________. For purposes hereof, beneficial ownership shall be calculated in accordance with Section 13(d) of the Exchange Act and the applicable regulations of the Commission. In addition, for purposes hereof,
“group” has the meaning set forth in Section 13(d) of the Exchange Act and the applicable regulations of the Commission. 

Conversion calculations: 
 Date
to Effect Conversion: _______________ 
 Number of shares of Series B Preferred Stock owned prior to Conversion:
_______________ 
 Number of shares of Series B Preferred Stock to be Converted: _______________ 

Number of shares of Common Stock to be Issued: _______________ 
 Address for delivery of physical certificates: ________________________________________ 
 Or for
DWAC Delivery: 
 DWAC Instructions: 
 Broker no: _______________ 
 Account no: ______________ 

 
			
	[HOLDER]
		
	 By:
	 	 
		 	Name:
		 	Title:
		
	 Date:exhibit_4-1.htm

EXHIBIT 4.1

 

U.S. $303,200,00

 

Poughkeepsie, New York 

December 26, 2007

 

PROMISSORY NOTE

 

FOR VALUE RECEIVED, Gilman + Ciocia, Inc., a Delaware corporation ("Maker") promises to pay to Prime Partners, Inc., a New York corporation (the "Payee"), during regular business hours at whatever place the Holder may from time to time designate, the principal sum of $303,200.00 plus interest thereon at Ten percent (10%) per annum, as follows:

 

	
1.  

	
The $303,200.00 principal balance plus interest shall be paid pursuant to the annexed amortization schedule in thirty-one (31) monthly payments of $11,138.78 on the first day of each month commencing on January 1, 2008 and continuing through and including July 1, 2010.

 

	
2.  

	
The Maker shall pay to the Payee a late fee equal to five (5%) percent of the payment due for each payment that is paid more than ten (10) days after it is due.

 

All amounts payable hereunder shall be payable to Payee in United States dollars at such bank account as shall be designated by the Payee in immediately available funds or as otherwise specified to Maker in writing. Payment on this note shall be applied first to any expenses of collection, then to accrued interest, and thereafter to the outstanding principal balance hereof.

 

This. Note may be prepaid in whole or in part at any time without penalty.

 

The following events shall each be an "Event of Default" under this Note:

 

	 	
(a) 

	
The Maker becomes insolvent or generally fails to pay, or admits inwriting its inability or refusal to pay, debts as they become due; or Maker applies for, consents to or acquiesces in the appointment of a trustee, receiver or other custodian for the Maker or any substantial part of its property, or makes a general assignment for the benefit of creditors; or, in the absence of such application, consent or acquiescence, a trustee, receiver or other custodian is appointed for the Maker, or for a substantial part of its property, and is not discharged within 60 days; or any bankruptcy, reorganization, debt arrangement or other case or proceeding under any bankruptcy or insolvency law, or any dissolution or liquidation proceeding, is commenced in respect of the Maker, and if such case or proceeding is not commenced by the Maker, it is consented to or acquiesced in by the Maker, or remains for 60 days undismissed; and

  

1

  

 

	
(b)  

	
Maker's failure to make any payment under this Note within thirty (30) days from the date the same becomes due and payable.

 

	
(c)  

	
If Maker sells or merges or transfers ownership and control of the corporation (meaning greater than 50% of outstanding common shares are transferred or sold).

 

 

Upon the occurrence of an Event of Default, the unpaid principal, all unpaid accrued interest thereon and all other amounts owing hereunder shall automatically become immediately clue and payable. Effective upon an Event of Default, the interest rate on this Note shall increase tol6%, or to such lesser interest rate as is permitted by applicable law. This Note may be prepaid at any time in whole or in part without penalty.

 

This Note is made with full recourse to the Maker including without limitation with full recourse to all assets of the Maker and pursuant to and upon all warranties, representations, covenants and agreements on the part of the Maker as contained herein. This Note is not secured.

 

Maker waives presentment and written demand for payment, notice of dishonor, protest and notice of protest of this Note, and shall pay all costs of collection when incurred, including, without limitation, reasonable attorneys' fees, costs and other expenses. Maker waives its rights to a jury trial in connection with any claims arising under this Note to the fullest extent permitted by law. If there has been an Event of Default by Maker hereunder, Payee shall be entitled to receive and Maker agrees to pay all costs of enforcement and collection incurred by Payee, including, without limitation, reasonable attorneys' fees relating thereto.

 

The provisions of this Note shall be binding on any successor to Maker and shall extend to any holder hereof.

 

This Note may not be changed, modified or terminated orally.

 

This note shall be governed by and construed in accordance with the laws of the State of New York without regard to any principles of conflicts of law. The Maker submits to the jurisdiction of the New York State Supreme Court, Dutchess County, for any collection lawsuits.

 

IN WITNESS WHEREOF, Maker has executed this instrument as of December 26, 2007. 

 

Gilman + Ciocia, Inc.

 

 

	 	 By:	 /s/Michael P. Ryan
	 	 	 Michael P. Ryan, President

 

 

  

2

  

 

$303,200 PRIME PARTNERS, INC. 

Principal borrowed: $303200.00

Annual Payments: 12 Total Payments: 32

Annual interest rate: 10.00% Periodic interest rate: 0.8333% 

Regular Payment amount: $11138.78

 

	
Pmt

	Principal 	
Interest

	
Cum Prin

	
Cum Int

	
Prin Bal

	
1

	
8612.11

	
2526.67

	
8612.11

	
2526.67

	
294587.89

	
2

	
8683.88

	
2454.90

	
17295.99

	
4981.57

	
285904.01

	
3

	
8756,25

	
2382.53

	
26052.24

	
7364.10

	
277147.76

	
4

	
8829.22

	
2309.56

	
34881,46

	
9673.66

	
268318.54

	
5

	
8902.79

	
2235.99

	
43784.25

	
11909.65

	
259415.75

	
6

	
8976.98

	
2161.80

	
52761.23

	
14071.45

	
250438.77

	
7

	
9051.79

	
2086.99

	
61813.02

	
16158.44

	
241386.98

	
8

	
9127.22

	
2011.56

	
70940.24

	
18170.00

	
232259.76

	
9

	
9203.28

	
1935.50

	
80143.52

	
20105.50

	
223056.48

	
10

	
9279.98

	
1858.80

	
89423.50

	
21964.30

	
213776.50

	
11

	
9357.31

	
1781A7

	
98780.81

	
23745.77

	
204419.19

	
12

	
9435.29

	
1703.49

	
108216.10

	
25449.26

	
194983.90

	
13

	
9513.91

	
1624.87

	
117730.01

	
27074.13

	
185469.99

	
14

	
9593.20

	
1545.58

	
127323.21

	
28619.71

	
175876.79

	
15

	
9673,14

	
1465.64

	
136996.35

	
30085.35

	
166203.65

	
16

	
9753.75

	
1385.03

	
146750.10

	
31470.38

	
156449.90

	
17

	
9835.03

	
1303.75

	
156585,13

	
32774.13

	
146614.87

	
18

	
9916.99

	
1221.79

	
166502.12

	
33995.92

	
136697.88

	
19

	
9999.63

	
1139.15

	
176501.75

	
35135.07

	
126698.25

	
20

	
10082.96

	
1055.82

	
186584.71

	
36190.89

	
116615.29

	
21

	
10166.99

	
971.79

	
196751.70

	
37162.68

	
106448.30

	
22

	
10251,71

	
887.07

	
207003.41

	
38049.75

	
96196.59

	
23

	
10337.14

	
801.64

	
217340.55

	
38851 .39

	
85859.45

	
24

	
10423.28

	
715.50

	
227763.83

	
39566.89

	
75436.17

	
25

	
10510.15

	
628.63

	
238273.98

	
40195.52

	
64926.02

	
26

	
10597.73

	
541.05

	
248871.71

	
40736.57

	
54328.29

	
27

	
10686.04

	
452.T4

	
259557.75

	
411'89.31

	
4364225

	
28

	
10775.09

	
363.69

	
270332.84

	
41553.00

	
32867.16

	
29

	
10864.89

	
273.89

	
281197.73

	
41826.89

	
22002.27

	
30

	
10955.43

	
183.35

	
292153.16

	
42010.24

	
11046.84

	
31

	
11046.72

	
92.06

	
303199.88

	
42102.30

	
0

 

 

 

 

 3

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