Amended and restated warrant to purchase common stock



 EXHIBIT 4.4 
 THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, AND MAY NOT BE SOLD, PLEDGED OR OTHERWISE TRANSFERRED WITHOUT AN EFFECTIVE REGISTRATION THEREOF UNDER SUCH ACT OR PURSUANT
TO RULE 144 OR AN OPINION OF COUNSEL REASONABLY SATISFACTORY TO THE CORPORATION AND ITS COUNSEL THAT SUCH REGISTRATION IS NOT REQUIRED. 
 AMENDED AND RESTATED WARRANT TO PURCHASE STOCK 
  

			
	Corporation:	  	PHENOMIX CORPORATION, a Delaware Corporation
	Number of Shares:	  	42,857
	Class of Stock:	  	Common Stock
	Initial Exercise Price:	  	$7.00 per share
	Original Issue Date:	  	December 23, 2004
	Expiration Date:	  	December 23, 2014 (Subject to Section 5.1)

 THIS AMENDED AND RESTATED WARRANT entered into as of July 19, 2007 certifies that, for good
and valuable consideration, the receipt of which is hereby acknowledged, COMERICA, INCORPORATED or its assignee (“Holder”) is entitled to purchase the number of fully paid and nonassessable shares of the class of securities (the
“Shares”) of the corporation (the “Company”) at the initial exercise price per Share (the “Warrant Price”) all as set forth above and as adjusted pursuant to Article 2 of this warrant, subject to the provisions and upon
the terms and conditions set forth in this warrant. 
 WHEREAS, on or about December 23, 2004, the Company issued to Comerica Bank,
later assigned to Comerica, Incorporated, a warrant to purchase shares of Common Stock of the Company (as the same has been amended prior to the date hereof, the “Prior Warrant”); and 
 WHEREAS, the Company and Holder desire to amend and restate the Prior Warrant in its entirety to read as set forth below, and to accept the terms and
conditions set forth below in lieu of any and all terms and conditions of the Prior Warrant as may have been agreed upon between the Company and Holder prior to the date hereof. 
 ARTICLE 1. EXERCISE. 
 1.1 Method of Exercise. Holder may exercise this warrant by delivering
this warrant and a duly executed Notice of Exercise in substantially the form attached as Appendix 1 to the principal office of the Company. Unless Holder is exercising the conversion right set forth in Section 1.2, Holder shall also deliver to
the Company a check for the aggregate Warrant Price for the Shares being purchased. 
 1.2 Conversion Right. In lieu of exercising
this warrant as specified in Section 1.1, Holder may from time to time convert this warrant, in whole or in part, into a number of Shares determined by dividing (a) the aggregate fair market value of the Shares or other securities
otherwise issuable upon exercise of this warrant minus the aggregate Warrant Price of such Shares by (b) the fair market value of one Share. The fair market value of the Shares shall be determined pursuant to Section 1.4. 
 1.3 Intentionally Omitted. 
 1.4
Fair Market Value. If the Shares are traded regularly in a public market, the fair market value of the Shares shall be the average of the closing prices of the Shares (or the closing price of the Company’s stock into which the Shares are
convertible) reported over the ten trading days immediately before Holder delivers its Notice of Exercise to the Company. If the Shares are not regularly traded in a public market, the Board of Directors of the Company shall determine fair market
value in its reasonable good faith judgment. 
  

 1 








 1.5 Delivery of Certificate and New Warrant. Promptly after Holder exercises or converts this
warrant, the Company shall deliver to Holder certificates for the Shares acquired and, if this warrant has not been fully exercised or converted and has not expired, a new warrant representing the Shares not so acquired. 
 1.6 Replacement of Warrants. On receipt of evidence reasonably satisfactory to the Company of the loss, theft, destruction or mutilation of this
warrant and, in the case of loss, theft or destruction, on delivery of an indemnity agreement reasonably satisfactory in form and amount to the Company or, in the case of mutilation, on surrender and cancellation of this warrant, the Company at its
expense shall execute and deliver, in lieu of this warrant, a new warrant of like tenor. 
 1.7 Repurchase on Sale, Merger, or
Consolidation of the Company. 
 1.7.1 “Acquisition.” For the purpose of this warrant,
“Acquisition” means (a) any sale, license, or other disposition of all or substantially all of the assets (including intellectual property) of the Company, or (b) any reorganization, consolidation, merger or sale of the voting
securities of the Company or any other transaction where the holders of the Company’s securities before the transaction beneficially own less than 50% of the outstanding voting securities of the surviving entity after the transaction.

 1.7.2 Assumption of Warrant. If upon the closing of any Acquisition the successor entity assumes the obligations of
this warrant, then this warrant shall be exercisable for the same securities, cash, and property as would be payable for the Shares issuable upon exercise of the unexercised portion of this warrant as if such Shares were outstanding on the record
date for the Acquisition and subsequent closing. The Warrant Price shall be adjusted accordingly. The Company shall use reasonable efforts to cause the surviving corporation to assume the obligations of this warrant. 
 1.7.3 Nonassumption. If upon the closing of any Acquisition the successor entity does not assume the obligations of this warrant
and Holder has not otherwise exercised this warrant in full, then this warrant shall be deemed to have been automatically converted pursuant to Section 1.2 and thereafter Holder shall participate in the Acquisition on the same terms as other
holders of the same class of securities of the Company. 
 ARTICLE 2. ADJUSTMENTS TO THE SHARES. 
 2.1 Stock Dividends, Splits, Etc. If the Company declares or pays a dividend on its common stock payable in common stock, or other securities,
subdivides the outstanding common stock into a greater amount of common stock, then upon exercise of this warrant, for each Share acquired, Holder shall receive, without cost to Holder, the total number and kind of securities to which Holder would
have been entitled had Holder owned the Shares of record as of the date the dividend or subdivision occurred. 
 2.2 Reclassification,
Exchange or Substitution. Upon any reclassification, exchange, substitution, or other event that results in a change of the number and/or class of the securities issuable upon exercise or conversion of this warrant, Holder shall be entitled to
receive, upon exercise or conversion of this warrant, the number and kind of securities and property that Holder would have received for the Shares if this warrant had been exercised immediately before such reclassification, exchange, substitution,
or other event. The Company or its successor shall promptly issue to Holder a new warrant for such new securities or other property. The new warrant shall provide for adjustments which shall be as nearly equivalent as may be practicable to the
adjustments provided for in this Article 2 including, without limitation, adjustments to the Warrant Price and to the number of securities or property issuable upon exercise of the new warrant. The provisions of this Section 2.2 shall similarly
apply to successive reclassifications, exchanges, substitutions, or other events. 
 2.3 Adjustments for Combinations, Etc. If the
outstanding Shares are combined or consolidated, by reclassification or otherwise, into a lesser number of shares, the Warrant Price shall be proportionately increased. If the outstanding Shares are combined or consolidated, by reclassification or
otherwise, into a greater number of shares, the Warrant Price shall be proportionately decreased. 
  

 2 








 2.4 Intentionally Omitted. 
 2.5 No Impairment. The Company shall not, by amendment of its Certificate of Incorporation or through a reorganization, transfer of assets,
consolidation, merger, dissolution, issue, or sale of securities or any other voluntary action, avoid or seek to avoid the observance or performance of any of the terms to be observed or performed under this warrant by the Company, but shall at all
times in good faith assist in carrying out all the provisions of this Article 2 and in taking all such action as may be necessary or appropriate to protect Holder’s rights under this Article against impairment. 
 2.6 Certificate as to Adjustments. Upon each adjustment of the Warrant Price, the Company at its expense shall promptly compute such adjustment,
and furnish Holder with a certificate of its Chief Financial Officer setting forth such adjustment and the facts upon which such adjustment is based. The Company shall, upon written request, furnish Holder a certificate setting forth the Warrant
Price in effect upon the date thereof and the series of adjustments leading to such Warrant Price. 
 2.7 Fractional Shares. No
fractional Shares shall be issuable upon exercise or conversion of the Warrant and the Number of Shares to be issued shall be rounded down to the nearest whole Share. If a fractional share interest arises upon any exercise or conversion of the
Warrant, the Company shall eliminate such fractional share interest by paying Holder amount computed by multiplying the fractional interest by the fair market value of a full Share. 
 ARTICLE 3. REPRESENTATIONS AND COVENANTS OF THE COMPANY. 
 3.1 Representations and Warranties.
The Company hereby represents and warrants to the Holder as follows: 
 (a) All Shares which may be issued upon the exercise
of the purchase right represented by this warrant, and all securities, if any, issuable upon conversion of the Shares, shall, upon issuance, be duly authorized, validly issued, fully paid and nonassessable, and free of any liens and encumbrances
except for restrictions on transfer provided for herein or under applicable federal and state securities laws. 
 (b) The
Company’s capitalization table attached to this warrant is true and complete as of the July 19, 2007. 
 3.2 Notice of Certain
Events. If the Company proposes at any time (a) to declare any dividend or distribution upon its common stock, whether in cash, property, stock, or other securities and whether or not a regular cash dividend; (b) to offer for
subscription pro rata to the holders of any class or series of its stock any additional shares of stock of any class or series or other rights; (c) to effect any reclassification or recapitalization of common stock; or (d) to merge or
consolidate with or into any other corporation, or sell, lease, license, or convey all or substantially all of its assets, or to liquidate, dissolve or wind up, then, in connection with each such event, the Company shall give Holder (1) at
least 20 days prior written notice of the date on which a record will be taken for such dividend, distribution, or subscription rights (and specifying the date on which the holders of common stock will be entitled thereto) or for determining rights
to vote, if any, in respect of the matters referred to in (a) and (b) above; and (2) in the case of the matters referred to in (c) and (d) above at least 20 days prior written notice of the date when the same will take place
(and specifying the date on which the holders of common stock will be entitled to exchange their common stock for securities or other property deliverable upon the occurrence of such event). 
 3.3 Information Rights. So long as the Holder holds this warrant and/or any of the Shares, the Company shall deliver to the Holder
(a) promptly after mailing, copies of all communiques to the shareholders of the Company, (b) within one hundred twenty (120) days after the end of each fiscal year of the Company, the annual audited financial statements of the
Company certified by independent public accountants of recognized standing and (c) within forty-five (45) days after the end of each of the first three quarters of each fiscal year, the Company’s quarterly, unaudited financial
statements. 
 3.4 Registration Under Securities Act of 1933, as amended. The Company acknowledges and agrees that Holder is entitled
to the piggyback registration rights set forth in Section 3 of that certain Amended and 

  

 3 








 
Restated Registration Rights Agreement dated February 28, 2007, as the same may be amended from time to time, with respect to all of the Shares issuable
upon exercise of this Warrant. 
 REPRESENTATIONS, WARRANTIES AND COVENANTS OF HOLDER. Holder hereby represents and warrants to and for the
benefit of the Company, with knowledge that the Company is relying thereon in issuing this Warrant to Holder, as follows: 
 3.5 Purchase
Entirely for Own Account. Holder hereby confirms that this Warrant and the Shares issuable upon exercise of this Warrant (collectively, the “Securities”) shall be acquired for investment for Holder’s own account, not as a
nominee or agent, and not with a view to the resale or distribution of any part thereof, and that Holder has no present intention of selling, granting any participation in, or otherwise distributing the same; provided, however, that Holder may
transfer all or part of this Warrant and the Shares issuable upon exercise of this Warrant to its affiliates. By executing this Warrant, Holder further represents that Holder does not have any contract, undertaking, agreement or arrangement with any
person to sell, transfer or grant participation to such person or to any third person, with respect to any of the Securities. Holder represents that it has full power and authority to enter into this Warrant. 
 3.6 Investment Experience. Holder regularly lends money to companies in the development stage and acknowledges that it is able to fend for itself
and has such knowledge and experience in financial or business matters that it is capable of evaluating the merits and risks of holding this Warrant. 
 3.7 Accredited Investor. Holder is an “accredited investor” within the meaning of Securities and Exchange Commission Rule 501 of Regulation D, as now in effect. 
 3.8 Restricted Securities. Holder understands that the Securities are characterized as “restricted securities” under the federal
securities laws inasmuch as they are being acquired from the Company in a transaction not involving a public offering and that under such laws and applicable regulations such securities may be resold without registration under the Securities Act of
1933, as amended (the “Act”), only in certain limited circumstances. Holder represents that it is familiar with Rule 144 promulgated under the Act, as now in effect, and understands the resale limitations imposed thereby and by the
Act. 
 3.9 Market Stand-off. Holder hereby agrees that, during the period of duration specified by the Company and an underwriter of
common stock or other securities of the Company (such period not to exceed one hundred eighty (l80) calendar days), following the effective date of a registration statement of the Company filed under the Act, it shall not, to the extent requested by
the Company and such underwriter, directly or indirectly sell, offer to sell, contract to sell (including, without limitation, any short sale), grant any option to purchase or otherwise transfer or dispose of any securities of the Company held by it
at any time during such period except common stock included in such registration. The foregoing covenants shall apply only to the Company’s initial public offering of equity securities, shall not apply to the sale of any shares by Holder to an
underwriter pursuant to an underwriting agreement and shall only be applicable to Holder if all the Company’s executive officers, directors and stockholders holding at least five percent (5%) of the Company’s voting securities enter
into similar agreements. In order to enforce the foregoing covenant, the Company may impose stop-transfer instructions with respect to the securities of Holder (and the shares or securities of every other person subject to the foregoing restriction)
until the end of such period. 
 MISCELLANEOUS. 
 3.10 Term: Notice of Expiration. This warrant is exercisable in whole or in part, at any time and from time to time on or before the Expiration Date set forth above; provided, however, that if the Company
completes its initial public offering within the three-year period immediately prior to the Expiration Date, the Expiration Date shall automatically be extended until the third anniversary of the effective date of the Company’s initial public
offering. If this warrant has not been exercised prior to the Expiration Date, this warrant shall be deemed to have been automatically exercised on the Expiration Date by “cashless” conversion pursuant to Section 1.2. 
  

 4 








 3.11 Legends. This warrant and the Shares (and the securities issuable, directly or indirectly,
upon conversion of the Shares, if any) shall be imprinted with a legend in substantially the following form: 
 THIS SECURITY HAS NOT BEEN
REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, AND MAY NOT BE SOLD, PLEDGED OR OTHERWISE TRANSFERRED WITHOUT AN EFFECTIVE REGISTRATION THEREOF UNDER SUCH ACT OR PURSUANT TO RULE 144 OR AN OPINION OF COUNSEL REASONABLY SATISFACTORY TO THE
CORPORATION AND ITS COUNSEL THAT SUCH REGISTRATION IS NOT REQUIRED. 
 THIS SECURITY IS SUBJECT TO THE RESTRICTIONS ON TRANSFER OF A CERTAIN
WARRANT DATED DECEMBER 23, 2004, AS AMENDED AND RESTATED, BY AND BETWEEN THE COMPANY AND THE HOLDER THEREOF, INCLUDING WITHOUT LIMITATION CERTAIN MARKET STAND-OFF RESTRICTIONS CONTAINED IN SECTION 4.5 THEREOF. 
 3.12 Compliance with Securities Laws on Transfer. This warrant and the Shares issuable upon exercise of this warrant (and the securities issuable,
directly or indirectly, upon conversion of the Shares, if any) may not be transferred or assigned in whole or in part (i) unless and until the transferee has agreed in writing for the benefit of the Company to be bound by all of the provisions
of this Warrant as if such transferee were the original Holder hereof, and (ii) without compliance with applicable federal and state securities laws by the transferor and the transferee (including, without limitation, the delivery of investment
representation letters and legal opinions reasonably satisfactory to the Company). The Company shall not require Holder to provide an opinion of counsel if the transfer is to an affiliate (as such term is defined under the Act) of Holder or if there
is no material question as to the availability of current information as referenced in Rule 144(c), Holder represents that it has complied with Rule 144(d) and (e) in reasonable detail, the selling broker represents that it has complied with
Rule 144(f), and the Company is provided with a copy of Holder’s notice of proposed sale. 
 3.13 Transfer Procedure. Subject to
the provisions of Section 4.3, Holder may transfer all or part of this warrant or the Shares issuable upon exercise of this warrant (or the securities issuable, directly or indirectly, upon conversion of the Shares, if any) by giving the
Company notice of the portion of the warrant being transferred setting forth the name, address and taxpayer identification number of the transferee and surrendering this warrant to the Company for reissuance to the transferee(s) (and Holder, if
applicable); provided, however, that Holder may transfer all or part of this warrant to its affiliates, including, without limitation, Comerica Incorporated, at any time without notice to the Company, and such affiliate shall then be entitled to all
the rights of Holder under this warrant and any related agreements, and the Company shall cooperate fully in ensuring that any stock issued upon exercise of this warrant is issued in the name of the affiliate that exercises the warrant. The terms
and conditions of this warrant shall inure to the benefit of, and be binding upon, the Company and the holders hereof and their respective permitted successors and assigns. Unless the Company is filing financial information with the SEC pursuant to
the Securities Exchange Act of 1934, the Company shall have the right to refuse to transfer any portion of this warrant to any person who directly competes with the Company. 
 3.14 Notices. All notices and other communications from the Company to the Holder, or vice versa, shall be deemed delivered and effective when
given personally or mailed by first-class registered or certified mail, postage prepaid, at such address as may have been furnished to the Company or the Holder, as the case may be, in writing by the Company or such Holder from time to time. All
notices to the Holder shall be addressed as follows: 
 Comerica, Incorporated 
 Attn: Warrant Administrator 
 500 Woodward Avenue, 32nd Floor, MC 3379 
 Detroit, MI 48226 
 3.15 Amendments. This warrant and any term hereof may be changed, waived, discharged or terminated only by an instrument in writing signed by the
party against which enforcement of such change, waiver, discharge or termination is sought. 
  

 5 








 3.16 Attorneys’ Fees. In the event of any dispute between the parties concerning the terms
and provisions of this warrant, the party prevailing in such dispute shall be entitled to collect from the other party all costs incurred in such dispute, including reasonable attorneys’ fees. 
 3.17 Governing Law. This warrant shall be governed by and construed in accordance with the laws of the State of California, without giving effect
to its principles regarding conflicts of law. 
 3.18 No Stockholder Rights. Except as expressly set forth herein, this warrant in and
of itself shall not entitle the Holder to any voting rights or other rights as a stockholder of the Company. 
 3.19 Amendment and
Restatement of Prior Warrant. The Prior Warrant is hereby amended in its entirety and restated herein. Such amendment and restatement is effective upon the execution and delivery of this Amended and Restated Warrant by the Company and Holder.
Upon such execution, all provisions of, rights granted and covenants made in the Prior Warrant are hereby waived, released and superseded in their entirety and shall have no further force or effect. 
  

			
	PHENOMIX CORPORATION
		
	By:	 	/s/ Chris Burnley
		
	Name:	 	Chris Burnley
		
	Title:	 	EVP & CBO


  

			
		
	By:	 	 
		
	Name:	 	 
		
	Title:	 	 


 Authorized signatories under Corporate Resolutions to Borrow or an authorized signer(s) under a resolution
covering warrants must sign the warrant. 
 Acknowledged and accepted: 
  

			
	COMERICA INCORPORATED
		
	By:	 	/s/ Ann M. Schwer
		
	Name:	 	Ann M. Schwer
		
	Title:	 	Vice President

  

 6 








 APPENDIX 1 
 NOTICE OF EXERCISE 
 1. The undersigned hereby elects to purchase
             shares of the              stock of PHENOMIX CORPORATION pursuant to the terms of the attached
warrant, and tenders herewith payment of the purchase price of such shares in full. 
 1. The undersigned hereby elects to convert the
attached warrant into shares in the manner specified in the warrant. This conversion is exercised with respect to              of the shares covered by the warrant. 
 [Strike paragraph that does not apply.] 
 2. Please issue a certificate or certificates representing said shares in the name of the undersigned or in such other name as is specified below: 
 Comerica, Incorporated 
 Attn: Warrant Administrator 
 500 Woodward Avenue, 32nd Floor, MC 3379 
 Detroit, MI 48226 
 3. The undersigned represents it is acquiring the shares solely for its own account and not as a nominee for
any other party and not with a view toward the resale or distribution thereof except in compliance with applicable securities laws. 
 COMERICA,
INCORPORATED or Registered Assignee 
  

	
	
	  
	(Signature)

  

	
	
	  
	(Date)