Exhibit
4.22


 


THE SECURITIES
REPRESENTED HEREBY HAVE BEEN ACQUIRED FOR INVESTMENT AND HAVE NOT BEEN
REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”).  SUCH SECURITIES MAY NOT BE SOLD OR
TRANSFERRED IN THE ABSENCE OF REGISTRATION OR AN EXEMPTION THEREFROM. RIGEL
PHARMACEUTICALS, INC. MAY REQUIRE AN OPINION OF COUNSEL REASONABLY ACCEPTABLE
TO IT THAT A PROPOSED TRANSFER OR SALE IS IN COMPLIANCE WITH THE ACT.


 


THE SALE, TRANSFER
OR VOTING OF THE SECURITIES REPRESENTED HEREBY IS RESTRICTED BY THE TERMS OF A
SECOND INVESTOR RIGHTS AGREEMENT BY AND AMONG RIGEL PHARMACEUTICALS, INC. AND
THE INVESTORS NAMED THEREIN. COPIES OF THE AGREEMENT MAY BE OBTAINED AT NO COST
BY WRITTEN REQUEST MADE BY THE HOLDERS OF RECORD OF THIS CERTIFICATE TO THE
SECRETARY OF RIGEL PHARMACEUTICALS, INC. AT THE PRINCIPAL EXECUTIVE OFFICES OF
RIGEL PHARMACEUTICALS, INC.


 


RIGEL
PHARMACEUTICALS, INC.


 


COMMON
STOCK PURCHASE WARRANT


 


	
  Warrant No. CS-14

  	
   

  	
  34,722 Shares

  
	
  June 26, 2003

  	
   

  	
   

  



 


1.     Issuance.  For value received, this Warrant is issued
to MPM BioEquities
Master Fund, L.P., by Rigel Pharmaceuticals, Inc.,
a Delaware corporation (hereinafter with its successors called the “Company”),
pursuant to the terms and conditions of that certain Common Stock and Warrant
Purchase Agreement, dated as of April 29, 2003, by and among the Company and
the investors listed on Schedule A thereto (the “Purchase Agreement”).


 


2.     Purchase
Price; Number of Shares.  The
registered holder of this Warrant (the “Holder”), commencing on the date hereof,
is entitled upon surrender of this Warrant, with the subscription form annexed
hereto duly executed, at the principal office of the Company, to purchase from
the Company thirty-four thousand seven hundred twenty-two (34,722) fully paid
and nonassessable shares (the “Shares”) of common stock, $.001 par value
per share, of the Company (the “Common Stock”), at a price per share of
$5.76 (the “Warrant
Price”).  Until such time as
this Warrant is exercised in full or expires, the Warrant Price and the
securities issuable upon exercise of this Warrant are subject to adjustment as
hereinafter provided.  The person or
persons under whose name or names any certificate representing Shares shall be
deemed to have become the holder of record of the Shares represented thereby as
at the close of business on the date this Warrant is exercised with respect to
such Shares, whether or not the transfer books of the Company shall be closed.


 


3.     Payment
of Purchase Price.  The Purchase
Price (as defined below) may be paid: (i) by certified or bank check or by wire
transfer of immediately available funds to an account


 


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designated by the Company; (ii)
by the surrender by the Holder to the Company of any promissory notes or other
obligations issued by the Company, with all such notes and obligations so
surrendered being credited against the Purchase Price in an amount equal to the
principal amount thereof plus accrued interest to the date of surrender; (iii)
exercise of the “net issue election” right provided for in Section 4; or (iv)
by any combination of the foregoing. The “Purchase
Price” shall mean the amount equal to the then applicable Warrant
Price multiplied by the number of Shares then being purchased.


 


4.     Net
Issue Election.  The Holder may
elect to receive, without the payment by the Holder of any additional
consideration, shares of Common Stock equal to the value of this Warrant or any
portion hereof by the surrender of this Warrant or such portion to the Company,
with the net issue election notice annexed hereto duly executed, at the
principal office of the Company. 
Thereupon, the Company shall issue to the Holder such number of fully
paid and nonassessable shares of Common Stock as is computed using the
following formula:


 




	
  X =

  	
  Y (A – B)

  
	
  A

  






 


	
  where:

  	
   

  	
  X =

  	
   

  	
  the number
  of shares of Common Stock to be issued to the Holder pursuant to this Section
  4.

  
	
   

  	
   

  	
   

  	
   

  	
   

  
	
   

  	
   

  	
  Y =

  	
   

  	
  the number
  of shares of Common Stock covered by this Warrant in respect of which the net
  issue election is made pursuant to this Section 4.

  
	
   

  	
   

  	
   

  	
   

  	
   

  
	
   

  	
   

  	
  A =

  	
   

  	
  the Fair
  Market Value (defined below) of one share of Common Stock, as determined at
  the time the net issue election is made pursuant to this Section 4.

  
	
   

  	
   

  	
   

  	
   

  	
   

  
	
   

  	
   

  	
  B =

  	
   

  	
  the Warrant
  Price in effect under this Warrant at the time the net issue election is made
  pursuant to this Section 4.

  



 


“Fair Market Value” of a share of Common Stock as of a
particular date (the “Determination Date”)
shall mean the average of the closing or last reported sale prices of the
Common Stock as reported on the Nasdaq National Market over the 30-day period
ending five business days prior to the Determination Date; provided, however,
that if (i) the Common Stock is neither traded on the Nasdaq National Market
nor on a national securities exchange, then Fair Market Value shall be the
average of the closing or last reported sale prices of the Common Stock over
the 30-day period ending five business days prior to the Determination Date
reflected in the over-the-counter market, as reported by the National Quotation
Bureau, Inc. or any organization performing a similar function, or if closing
prices are not then routinely reported for the over-the-counter market, the
average of the last bid and asked prices of the Common Stock over the 30-day
period ending five business days prior to the Determination Date and (ii) if
there is no public market for the Common Stock, then Fair Market Value shall be
determined in good faith by the Company’s Board of Directors.


 


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5.     Partial
Exercise.  This Warrant may be
exercised in part, and the Holder shall be entitled to receive a new warrant,
which shall be dated as of the date of this Warrant, covering the number of
Shares in respect of which this Warrant shall not have been exercised.


 


6.     Fractional
Shares.  In no event shall any
fractional share of Common Stock be issued upon any exercise of this
Warrant.  If, upon exercise of this
Warrant as an entirety, the Holder would, except as provided in this Section 6,
be entitled to receive a fractional share of Common Stock, then the Company
shall pay in lieu thereof, the Fair Market Value of such fractional share in
cash.


 


7.     Expiration
Date; Early Termination.  This
Warrant or any Successor Warrant (as defined in Section 10 below) shall expire
on the close of business on June 26, 2008 (the “Expiration Date”), and shall be void thereafter.


 


8.     Reserved
Shares; Valid Issuance.  The Company
covenants that it will at all times from and after the date hereof reserve and
keep available such number of its authorized shares of Common Stock, free from
all preemptive or similar rights therein, as will be sufficient to permit the
exercise of this Warrant in full into shares of Common Stock upon such
exercise.  If at any time prior to the
Expiration Date the number of authorized but unissued shares of Common Stock
shall not be sufficient to permit exercise of this Warrant, the Company shall
take such corporate action as may, in the opinion of its counsel, be necessary
to increase its authorized but unissued shares of Common Stock to such number
of shares as shall be sufficient for such purposes. The Company further
covenants that such shares as may be issued pursuant to such exercise will,
upon issuance, be duly and validly issued, fully paid and nonassessable and
free from all taxes, liens and charges with respect to the issuance thereof.


 


9.     Stock
Splits and Dividends.  If after the
date hereof the Company shall subdivide the Common Stock, by split-up or
otherwise, combine the Common Stock or issue additional shares of Common Stock
in payment of a stock dividend on the Common Stock, then the number of Shares
issuable upon the exercise of this Warrant shall forthwith be proportionately
increased in the case of a subdivision or stock dividend, or proportionately
decreased in the case of a combination, and the Warrant Price shall forthwith
be proportionately decreased in the case of a subdivision or stock dividend, or
proportionately increased in the case of a combination.


 


10.  Mergers and Reclassifications.


 


(a)   If
after the date hereof the Company shall enter into any Reorganization (as
hereinafter defined), then, as a condition of such Reorganization, lawful
provisions shall be made, and duly executed documents evidencing the same from
the Company or its successor shall be delivered to the Holder (a “Successor Warrant”), so that the Holder
shall thereafter have the right to purchase, at a total price not to exceed
that payable upon the exercise of this Warrant in full, the kind and amount of
shares of stock and other securities and property receivable upon such
Reorganization by a holder of the number of shares of Common Stock that might
have been purchased by the Holder immediately prior to such Reorganization, and
in any such case appropriate provisions shall be made with respect to the
rights and interest of the Holder to the end that the provisions hereof
(including without limitation, provisions for the adjustment of the


 


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Warrant Price and the number of shares issuable hereunder and the
provisions relating to the net issue election) shall thereafter be applicable
in relation to any shares of stock or other securities and property thereafter
deliverable upon exercise hereof.


 


(b)   For
the purposes of this Section 10, the term “Reorganization” shall include
without limitation any reclassification, capital reorganization or change of
the Common Stock (other than as a result of a subdivision, combination or stock
dividend provided for in Section 9 hereof), any consolidation of the Company
with, or merger of the Company into, another corporation or other business
organization (other than a merger in which the Company is the surviving
corporation and which does not result in any reclassification or change of the
outstanding Common Stock), or any sale or conveyance to another corporation or
other business organization of all or substantially all of the assets of the
Company


 


11.  Certificate
of Adjustment. Whenever the Warrant Price is adjusted, as herein provided,
the Company shall promptly deliver to the Holder a certificate of the Company’s
Chief Financial Officer setting forth the Warrant Price after such adjustment
and setting forth a brief statement of the facts requiring such adjustment.


 


12.  Notices
of Record Date, Etc.  In the event
of:


 


(a)   any
taking by the Company of a record of the holders of any class of securities for
the purpose of determining the holders thereof who are entitled to receive any
dividend or other distribution, or any right to subscribe for, purchase, sell
or otherwise acquire or dispose of any shares of stock of any class or any
other securities or property, or to receive any other right;


 


(b)   any
reclassification of the capital stock of the Company, capital reorganization of
the Company, consolidation or merger involving the Company or sale or
conveyance of all or substantially all of its assets; or


 


(c)   any
voluntary or involuntary dissolution, liquidation or winding-up of the Company;


 


then in each such event the Company will provide or cause to be
provided to the Holder a written notice thereof.  Such notice shall be provided at least 15 calendar days prior to
the date specified in such notice on which any such action is to be taken.


 


13.  Representations,
Warranties and Covenants.  This
Warrant is issued and delivered by the Company and accepted by each Holder on
the basis of the following representations, warranties and covenants made by
the Company:


 


(a)   The
Company has all necessary authority to issue, execute and deliver this Warrant
and to perform its obligations hereunder. 
This Warrant has been duly authorized, issued, executed and delivered by
the Company and is the valid and binding obligation of the Company, enforceable
in accordance with its terms, except as enforceability may be limited by
bankruptcy, insolvency, reorganization or other similar laws of general
application affecting the enforcement of the Holder’s rights or by general
equity principals or public policy concerns.


 


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(b)   The
Shares have been duly authorized and reserved for issuance by the Company and,
when issued in accordance with the terms hereof, will be validly issued, fully
paid and nonassessable.


 


14.  Amendment
and Waiver.  The terms of this
Warrant may be amended, modified or waived only with the written consent of the
party against which enforcement of the same is sought.


 


15.  Representations
and Covenants of the Holder.  This
Warrant has been entered into by the Company in reliance upon the following
representations and covenants of the Holder, which by its execution hereof the
Holder hereby confirms:


 


(a)   The
Holder is an “accredited investor” as defined in Regulation D under the
Securities Act of 1933, as amended (the “Securities
Act”), and the Holder is knowledgeable, sophisticated and
experienced in making, and is qualified to make decisions with respect to,
investments in shares presenting an investment decision like that involved in
the purchase of the Shares and the Warrant, including investments in securities
issued by the Company and investments in comparable companies, and has
requested, received, reviewed and considered all information it deemed relevant
in making an informed decision to purchase the Warrant;


 


(b)   The
Holder is acquiring the Warrant in the ordinary course of its business and for
its own account for investment only and with no present intention of
distributing the Warrant or any of the Shares or any arrangement or
understanding with any other persons regarding the distribution of the Warrant
or the Shares; and


 


(c)   The
Holder will not, directly or indirectly, offer, sell, pledge, transfer or
otherwise dispose of (or solicit any offers to buy, purchase or otherwise
acquire or take a pledge of) the Warrant or any of the Shares except in
compliance with the Securities Act, applicable state securities laws and the
respective rules and regulations promulgated thereunder.


 


16.  Notices,
Transfers, Etc.


 


(a)   Any
notice or written communication required or permitted to be given to the Holder
may be given by certified mall or delivered to the Holder at the address most
recently provided by the Holder to the Company.


 


(b)   Subject
to compliance with applicable federal and state securities laws and any other
contractual restrictions between the Company and the Holder contained in the
Purchase Agreement or that certain Second Investor Rights Agreement, dated as
of the date hereof, by and among the Company and the investors named therein,
this Warrant may be transferred by the Holder with respect to any or all of the
Shares purchasable hereunder.  Upon
surrender of this Warrant to the Company, together with the assignment notice
annexed hereto duly executed, for transfer of this Warrant as an entirety by
the Holder, the Company shall issue a new warrant of the same denomination to
the assignee.  Upon surrender of this
Warrant to the Company, together with the assignment hereof properly endorsed,
by the Holder for transfer with respect to a portion of the Shares, the Company
shall issue a new warrant to the assignee, in such


 


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denomination as shall be requested by the Holder hereof, and shall
issue to such Holder a new warrant covering the number of Shares in respect of
which this Warrant shall not have been transferred.


 


(c)   The
Company acknowledges and agrees that an opinion of counsel shall not be
required upon the transfer by the Holder of any securities to an “Affiliate”
(as defined in Rule 12b-2 of the rules and regulations promulgated under the
Securities and Exchange Act of 1934, as amended) of such Holder.


 


(d)   In
case this Warrant shall be mutilated, lost, stolen or destroyed, the Company
shall issue a new warrant of like tenor and denomination and deliver the same
(i) in exchange and substitution for and upon surrender and cancellation of any
mutilated Warrant or (ii) in lieu of any Warrant lost, stolen or destroyed,
upon receipt of an affidavit of the Holder or other evidence reasonably
satisfactory to the Company of the loss, theft or destruction of such Warrant
and an indemnification of loss by the Holder in favor of the Company.


 


17.  Transfer
to Comply with the Securities Act.   This Warrant may not be exercised and neither this Warrant nor any
of the Shares, nor any interest in either, may be offered, sold, assigned,
pledged, hypothecated, encumbered or in any other manner transferred or
disposed of, in whole or in part, except in compliance with applicable United
States federal and state securities laws and the terms and conditions
hereof.  Each Warrant shall bear a
legend in substantially the same form as the legend set forth on the first page
of this Warrant.  Each certificate for
Shares issued upon exercise of this Warrant, unless at the time of exercise
such Shares are acquired pursuant to a registration statement that has been
declared effective under the Securities Act and applicable blue sky laws, shall
bear legends substantially in the following form:


 


“THE SHARES REPRESENTED
BY THIS CERTIFICATE HAVE BEEN ACQUIRED FOR INVESTMENT AND HAVE NOT BEEN
REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”).  SUCH SHARES MAY NOT BE SOLD OR TRANSFERRED
IN THE ABSENCE OF REGISTRATION OR AN EXEMPTION THEREFROM. RIGEL PHARMACEUTICALS,
INC. MAY REQUIRE AN OPINION OF COUNSEL REASONABLY ACCEPTABLE TO IT THAT A
PROPOSED TRANSFER OR SALE IS IN COMPLIANCE WITH THE ACT.”


 


“THE SALE, TRANSFER OR
VOTING OF THE SHARES REPRESENTED BY THIS CERTIFICATE IS RESTRICTED BY THE TERMS
OF A SECOND INVESTOR RIGHTS AGREEMENT BY AND AMONG RIGEL PHARMACEUTICALS, INC.
AND THE INVESTORS NAMED THEREIN. COPIES OF THE AGREEMENT MAY BE OBTAINED AT NO
COST BY WRITTEN REQUEST MADE BY THE HOLDERS OF RECORD OF THIS CERTIFICATE TO


 


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THE SECRETARY OF RIGEL PHARMACEUTICALS,
INC. AT THE PRINCIPAL EXECUTIVE OFFICES OF RIGEL PHARMACEUTICALS, INC.”


 


Any certificate
for any Shares issued at any time in exchange or substitution for any
certificate for any Shares bearing such legends (except a new certificate for
any Shares issued after the acquisition of such Shares pursuant to a
registration statement that has been declared effective under the Securities
Act) shall also bear such legends unless, in the opinion of counsel for the
Company, the Shares represented thereby need no longer be subject to the
restriction contained herein.  The
provisions of this Section 17 shall be binding upon all subsequent holders of
certificates for Shares bearing the above legends and all subsequent holders of
this Warrant, if any.


 


18.  Rights
of the Holder.  The Holder shall not, by virtue hereof, be
entitled to any rights of a stockholder of the Company, either at law or
equity, and the rights of the Holder are limited to those expressed in this
Warrant.  Nothing contained in this Warrant
shall be construed as conferring upon the Holder hereof the right to vote, to
consent or to receive notice as a stockholder of the Company on any matters or
with respect to any rights whatsoever as a stockholder of the Company.  No dividends or interest shall be payable or
accrued in respect of this Warrant or the interest represented hereby or the
Shares purchasable hereunder until, and only to the extent that, this Warrant
shall have been exercised in accordance with its terms.


 


19.  No
Impairment.  The Company will not,
by amendment of its Amended and Restated Certificate of Incorporation or
through any reclassification, capital reorganization, consolidation, merger,
sale or conveyance of assets, dissolution, liquidation, issue or sale of
securities or any other voluntary action, avoid or seek to avoid the observance
of performance of any of the terms of this Warrant, but will at all times in
good faith assist in the carrying out of all such terms and in the taking of
all such action as may be necessary or appropriate in order to protect the
rights of the Holder.


 


20.  Governing
Law.  The provisions and terms of
this Warrant shall be governed by and construed in accordance with the internal
laws of the State of California.


 


21.  Successors
and Assigns.  This Warrant shall be
binding upon the Company’s successors and assigns and shall inure to the
benefit of the Holder’s successors, legal representatives and permitted
assigns.


 


22.  Business
Days.  If the last or appointed day
for the taking of any action required or the expiration of any rights granted
herein shall be a Saturday or Sunday or a legal holiday in California, then
such action may be taken or right may be exercised on the next succeeding day
that is not a Saturday or Sunday or such a legal holiday.


 


23.  Severability.  If one or more provisions of this Warrant are
held to be unenforceable under applicable law, such provision shall be excluded
from this Warrant, and the balance of the Warrant shall be interpreted as if
such provision were so excluded and shall be enforceable in accordance with its
terms.


 


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In Witness Whereof, the Company has duly
caused this Warrant to be signed by its duly authorized officer and to be dated
as of the date first written above.


 


	
   

  	
  Company:

  
	
   

  	
   

  
	
   

  	
  Rigel Pharmaceuticals, Inc.

  
	
   

  	
   

  
	
   

  	
  By:

  	
   /s/
  James M. Gower

  	
   

  
	
   

  	
   

  	
   James
  M. Gower

  
	
   

  	
   

  	
   Chairman
  and Chief Executive Officer

  



 


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Notice of Exercise


 


(1)           The undersigned hereby:


 


[             ]                elects to purchase
             
shares of Common Stock of the Company pursuant to the terms of the attached
Warrant, and tenders herewith payment of the purchase price of such shares in
full, together with all applicable transfer taxes, if any.


 


[             ]                elects to exercise
its net issuance rights pursuant to Section 4 of the attached Warrant with
respect to
             
shares of Common Stock, and shall tender payment of all applicable transfer
taxes, if any.


 


(2)           Please
issue a certificate or certificates representing said shares of Common Stock in
the name of the undersigned or in such other name as is specified below:


 


(Name)


 


 


(Address)


 


(3)           The undersigned represents that the
aforesaid shares are being acquired for the account of the undersigned for
investment and not with a view to, or for resale in connection with, the
distribution thereof and that the undersigned has no present intention of
distributing or reselling such shares, all except as in compliance with
applicable securities laws. 


 


	
   

  	
   

  	
   

  	
   

  
	
  (Date)

  	
  (Signature)  

  
	
   

  	
   

  
	
   

  	
   

  	
   

  
	
   

  	
  (Print name)

  



 

















 


Assignment


 


For value received
                                                                        
hereby sells, assigns and transfers unto                                                                                                               


 


[Please print or type the name
and address of Assignee]


 


 


the within Warrant, and does hereby irrevocably constitute and appoint
                                                                        
its attorney to transfer the within Warrant on the books of the within named
Company with full power of substitution on the premises.


 


	
  Dated:

  	
   

  	
   

  	
   

  	
   

  
	
   

  
	
   

  
	
  In the Presence of: