Document:

exv10w7

Exhibit 10.7

THIS WARRANT AND THE SECURITIES ISSUABLE UPON EXERCISE HEREOF HAVE NOT BEEN REGISTERED UNDER THE
SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), OR ANY OTHER SECURITIES LAWS AND MAY NOT
BE OFFERED FOR SALE, SOLD, TRANSFERRED, PLEDGED OR HYPOTHECATED IN THE ABSENCE OF (1) AN EFFECTIVE
REGISTRATION STATEMENT COVERING SUCH SECURITIES UNDER THE SECURITIES ACT AND ANY OTHER APPLICABLE
SECURITIES LAWS, OR (2) AN OPINION OF COUNSEL REASONABLY SATISFACTORY TO THE COMPANY THAT SUCH
REGISTRATION IS NOT REQUIRED.

EMISPHERE TECHNOLOGIES, INC.

WARRANT

			
	Warrant No. A-26
	 	Original Issue Date: August 21, 2009

     EMISPHERE TECHNOLOGIES, INC., a Delaware corporation (the “Company”), hereby certifies
that, for value received, MHR Capital Partners (100) LP or its permitted registered assigns (the
“Holder”), is entitled to purchase from the Company up to a total of 101,821 shares of
common stock, $0.01 par value (the “Common Stock”), of the Company (each such share, a
“Warrant Share” and all such shares, the “Warrant Shares”) at an exercise price
equal to $0.70 per share (as adjusted from time to time as provided herein, the “Exercise
Price”), at any time and from time to time on or after the Original Issue Date and through and
including August 21, 2014 (the “Expiration Date” ), and subject to the following terms and
conditions:

     This Warrant is one of a series of warrants issued pursuant to that certain Securities
Purchase Agreement dated August 19, 2009, by and between the Company and each the purchasers
identified therein (the “Purchase Agreement”). All such warrants are referred to herein,
collectively, as the “Warrants.”

     1. Definitions. In addition to the terms defined elsewhere in this Warrant,
capitalized terms that are not otherwise defined herein have the meanings given to such terms in
the Purchase Agreement.

     2. List of Warrant Holders. The Company shall register this Warrant, upon records to
be maintained by the Company for that purpose (the “Warrant Register”), in the name of the
record Holder (which shall include the initial Holder or, as the case may be, any registered
assignee to which this Warrant is permissibly assigned hereunder from time to time). The Company
may deem and treat the registered Holder of this Warrant as the absolute owner hereof for the
purpose of any exercise hereof or any distribution to the Holder, and for all other purposes,
absent actual notice to the contrary.

 

 

     3. List of Transfers; Restrictions on Transfer.

     (a) This Warrant and the Warrant Shares are subject to the restrictions on transfer set forth
in this Section 3.

     (b) The Company shall register any such transfer of all or any portion of this Warrant in the
Warrant Register, upon surrender of this Warrant, with the Form of Assignment attached hereto duly
completed and signed, to the Company at its address specified herein. Upon any such registration
or transfer, a new Warrant to purchase Common Stock, in substantially the form of this Warrant (any
such new Warrant, a “New Warrant”), evidencing the portion of this Warrant so transferred
shall be issued to the transferee and a New Warrant evidencing the remaining portion of this
Warrant not so transferred, if any, shall be issued to the transferring Holder. The acceptance of
the New Warrant by the transferee thereof shall be deemed the acceptance by such transferee of all
of the rights and obligations in respect of the New Warrant that the Holder has in respect of this
Warrant.

     (c) If, but only if, at the time of the surrender of this Warrant in connection with any
transfer of this Warrant, the Holder is an Affiliate of the Company, and transfer of this Warrant
shall not be registered pursuant to an effective registration statement under the Securities Act
and under applicable state securities or blue sky laws, the Company may require, as a condition of
allowing such transfer (i) that the Holder or transferee of this Warrant, as the case may be,
furnish to the Company a written opinion of counsel (which opinion shall be in form, substance and
scope customary for opinions of counsel in comparable transactions) to the effect that such
transfer may be made without registration under the Securities Act and under applicable state
securities or blue sky laws, (ii) that the holder or transferee execute and deliver to the Company
an investment letter in form and substance acceptable to the Company and (iii) that the transferee
be an “accredited investor” as defined in Rule 501(a) promulgated under the Securities Act.

     4. Exercise and Duration of Warrants.

     (a) All or any part of this Warrant shall be exercisable by the registered Holder in any
manner permitted by Section 10 of this Warrant at any time and from time to time on or after the
Original Issue Date and through and including the Expiration Date. Subject to Section 11 hereof,
at 5:00 p.m., New York City time, on the Expiration Date, the portion of this Warrant not exercised
prior thereto shall be and become void and of no value and this Warrant shall be terminated and no
longer outstanding. In addition, if cashless exercise would be permitted under Section 10(b) of
this Warrant, then all or part of this Warrant may be exercised by the registered Holder utilizing
such cashless exercise provisions at any time, or from time to time, on or after the Original Issue
Date and through and including the Expiration Date.

     (b) The Holder may exercise this Warrant by delivering to the Company (i) an exercise notice,
in the form attached hereto (the “Exercise Notice”), completed and duly signed, and (ii) if
such Holder is not utilizing the cashless exercise provisions set forth in this Warrant, payment of
the Exercise Price for the number of Warrant Shares as to which this Warrant is being exercised.
The date such items are delivered to the Company (as determined in accordance with the notice
provisions hereof) is an “Exercise Date.” The Holder shall not be required to

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deliver the original Warrant in order to effect an exercise hereunder. Execution and delivery
of the Exercise Notice shall have the same effect as cancellation of the original Warrant and
issuance of a New Warrant evidencing the right to purchase the remaining number of Warrant Shares.
Additionally, at the request of the Holder, if this Warrant shall have been exercised in part and
the Holder shall have surrendered this Warrant certificate, the Company shall, at the time of
delivery of the certificate or certificates representing Warrant Shares, deliver to Holder a new
Warrant evidencing the rights of Holder to purchase the unpurchased Warrant Shares called for by
this Warrant, which new Warrant shall in all other respects be identical with this Warrant.

     5. Delivery of Warrant Shares.

     (a) Upon exercise of this Warrant, the Company shall promptly (but in no event later than
three Trading Days after the Exercise Date) issue or cause to be issued and cause to be delivered
to or upon the written order of the Holder and in such name or names as the Holder may designate
(provided that, if a registration statement is not then effective and the Holder directs the
Company to deliver a certificate for the Warrant Shares in a name other than that of the Holder or
an Affiliate of the Holder, it shall deliver to the Company on the Exercise Date an opinion of
counsel reasonably satisfactory to the Company to the effect that the issuance of such Warrant
Shares in such other name may be made pursuant to an available exemption from the registration
requirements of the Securities Act and all applicable state securities or blue sky laws), a
certificate for the Warrant Shares issuable upon such exercise, free of restrictive legends unless
a registration statement is not then effective or the Warrant Shares are not freely transferable
without volume restrictions or current public information requirements pursuant to Rule 144 under
the Securities Act. The Holder, or any Person permissibly so designated by the Holder to receive
Warrant Shares, shall be deemed to have become the holder of record of such Warrant Shares as of
the Exercise Date. If the Warrant Shares can be issued without restrictive legends, the Company
shall, upon the written request of the Holder, use its best efforts to deliver, or cause to be
delivered, Warrant Shares hereunder electronically through the Depository Trust and Clearing
Corporation DWAC system or another established clearing corporation performing similar functions,
if available; provided, that, the Company may, but will not be required to, change its transfer
agent if its current transfer agent cannot deliver Warrant Shares electronically through the
Depository Trust and Clearing Corporation.

     (b) If by the close of the third Trading Day after delivery of an Exercise Notice, the Company
fails to deliver to the Holder a certificate representing the required number of Warrant Shares in
the manner required pursuant to Section 5(a), and if after such third Trading Day and prior to the
receipt of such Warrant Shares, the Holder purchases (in an open market transaction or otherwise)
shares of Common Stock to deliver in satisfaction of a sale by the Holder of the Warrant Shares
which the Holder anticipated receiving upon such exercise (a “Buy-In”), then the Company
shall, within three Trading Days after the Holder’s request and in the Holder’s sole discretion,
either (1) pay in cash to the Holder an amount equal to the Holder’s total purchase price
(including brokerage commissions, if any) for the shares of Common Stock so purchased (the
“Buy-In Price”), at which point the Company’s obligation to deliver such certificate (and
to issue such Warrant Shares) shall terminate or (ii) promptly honor its obligation to deliver to
the Holder a certificate or certificates representing such Warrant Shares and pay cash to the
Holder in an amount equal to the excess (if any) of the Buy-In Price over the product of (A) such
number of Warrant Shares, times (B) the closing bid price on the date of the event giving rise to the Company’s obligation to deliver such certificate.

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     (c) To the extent permitted by law, the Company’s obligations to issue and deliver Warrant
Shares in accordance with the terms hereof are absolute and unconditional, irrespective of any
action or inaction by the 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 the Holder or any other Person of any obligation to the Company or any violation or
alleged violation of law by the Holder or any other Person, and irrespective of any other
circumstance that might otherwise limit such obligation of the Company to the Holder in connection
with the issuance of Warrant Shares. 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 Company’s failure to
timely deliver certificates representing shares of Common Stock upon exercise of the Warrant as
required pursuant to the terms hereof.

     6. Charges, Taxes and Expenses. Issuance and delivery of certificates for shares of
Common Stock upon exercise of this Warrant shall be made without charge to the Holder for any issue
or transfer tax, withholding tax, transfer agent fee or other incidental tax or expense in respect
of the issuance of such certificates, all of which taxes and expenses shall be paid by the Company;
provided, however, that the Company shall not be required to pay any tax that may be payable in
respect of any transfer involved in the registration of any certificates for Warrant Shares or
Warrants in a name other than that of the Holder. The Holder shall be responsible for all other
tax liability that may arise as a result of holding or transferring this Warrant or receiving
Warrant Shares upon exercise hereof.

     7. Replacement of Warrant. If this Warrant is mutilated, lost, stolen or destroyed,
the Company shall issue or cause to be issued in exchange and substitution for and upon
cancellation hereof, or in lieu of and substitution for this Warrant, a New Warrant, but only upon
receipt of evidence reasonably satisfactory to the Company of such loss, theft or destruction and
customary and reasonable indemnity (which shall not include a surety bond), if requested.
Applicants for a New Warrant under such circumstances shall also comply with such other reasonable
regulations and procedures and pay such other reasonable third-party costs as the Company may
prescribe. If a New Warrant is requested as a result of a mutilation of this Warrant, then the
Holder shall deliver such mutilated Warrant to the Company as a condition precedent to the
Company’s obligation to issue the New Warrant.

     8. Reservation of Warrant Shares. The Company covenants that it will at all times
reserve and keep available out of the aggregate of its authorized but unissued and otherwise
unreserved Common Stock, solely for the purpose of enabling it to issue Warrant Shares upon
exercise of this Warrant as herein provided, the number of Warrant Shares that are then issuable
and deliverable upon the exercise of this entire Warrant, free from preemptive rights or any other
contingent purchase rights of persons other than the Holder (taking into account the adjustments
and restrictions of Section 9). The Company covenants that all Warrant Shares so issuable and
deliverable shall, upon issuance and the payment of the applicable Exercise Price in accordance
with the terms hereof, be duly and validly authorized, issued and fully paid and nonassessable.

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     9. Certain Adjustments. The Exercise Price and number of Warrant Shares issuable upon
exercise of this Warrant are subject to adjustment from time to time as set forth in this Section
9.

     a) Stock Dividends and Splits. If the Company, at any time while this Warrant
is outstanding, (i) pays a stock dividend on its Common Stock or otherwise makes a
distribution on any class of capital stock that is payable in shares of Common Stock, (ii)
subdivides outstanding shares of Common Stock into a larger number of shares, or (iii)
combines outstanding shares of Common Stock into a smaller number of shares, then in each
such case the Exercise Price shall be multiplied by a fraction of which the numerator shall
be the number of shares of Common Stock outstanding immediately before such event and of
which the denominator shall be the number of shares of Common Stock outstanding immediately
after such event. Any adjustment made pursuant to clause (i) of this paragraph shall become
effective immediately after the record date for the determination of stockholders entitled
to receive such dividend or distribution, and any adjustment pursuant to clause (ii) or
(iii) of this paragraph shall become effective immediately after the effective date of such
subdivision or combination.

     b) Pro Rata Distributions. If the Company, at any time while this Warrant is
outstanding, distributes to all holders of Common Stock for no consideration (i) evidences
of its indebtedness, (ii) any security (other than a distribution of Common Stock covered by
the preceding paragraph), (iii) rights or warrants to subscribe for or purchase any
security, or (iv) any other asset (in each case, “Distributed Property”), then, upon
any exercise of this Warrant that occurs after the record date fixed for determination of
stockholders entitled to receive such distribution, the Holder shall be entitled to receive,
in addition to the Warrant Shares otherwise issuable upon such exercise (if applicable), the
Distributed Property that such Holder would have been entitled to receive in respect of such
number of Warrant Shares had the Holder been the record holder of such Warrant Shares
immediately prior to such record date.

     c) Fundamental Transactions. If, at any time while this Warrant is outstanding
(i) the Company effects any merger or consolidation of the Company with or into another
Person, in which the shareholders of the Company as of immediately prior to the transaction
own less than a majority of the outstanding stock of the surviving entity, (ii) the Company
effects any sale of all or substantially all of its assets in one or a series of related
transactions, (iii) any tender offer or exchange offer (whether by the Company or another
Person) is completed pursuant to which holders of Common Stock are permitted to tender or
exchange their shares for other securities, cash or property, or (iv) the Company effects
any reclassification of the Common Stock or any compulsory share exchange pursuant to which
the Common Stock is effectively converted into or exchanged for other securities, cash or
property (each, a “Fundamental Transaction”), then the Holder shall have the right
thereafter to receive, upon exercise of this Warrant, the same amount and kind 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 the number of Warrant Shares then issuable upon exercise in full
of this Warrant (the “Alternate Consideration”). The

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Company shall not effect any such Fundamental Transaction unless prior to or
simultaneously with the consummation thereof, any successor to the Company, surviving entity
or the corporation purchasing or otherwise acquiring such assets or other appropriate
corporation or entity shall assume the obligation to deliver to the Holder, such Alternate
Consideration as, in accordance with the foregoing provisions, the Holder may be entitled to
purchase, and the other obligations under this Warrant. The provisions of this paragraph
(c) shall similarly apply to subsequent transactions analogous to a Fundamental Transaction.
Notwithstanding anything to the contrary, in the event of a Fundamental Transaction that is
(1) an all cash transaction or (2) a “Rule 13e-3 transaction” as defined in Rule 13e-3 under
the Exchange Act, the Company or any Successor Entity (as defined below) shall, at the
Holder’s option, exercisable at any time concurrently with, or within 30 days after, the
consummation of the Fundamental Transaction, purchase this Warrant from the Holder by paying
to the Holder an amount of cash equal to the Black Scholes Value of the remaining
unexercised portion of this Warrant on the date of the consummation of such Fundamental
Transaction. “Black Scholes Value” means the value of this Warrant based on the
Black and Scholes Option Pricing Model obtained from the “OV” function on Bloomberg, L.P.
(“Bloomberg”) determined as of the day of consummation of the applicable Fundamental
Transaction for pricing purposes and reflecting (A) a risk-free interest rate corresponding
to the U.S. Treasury rate for a period equal to the time between the date of the public
announcement of the applicable Fundamental Transaction and the Termination Date, (B) an
expected volatility equal to the greater of 100% and the 100 day volatility obtained from
the HVT function on Bloomberg as of the Trading Day immediately following the public
announcement of the applicable Fundamental Transaction, (C) the underlying price per share
used in such calculation shall be the sum of the price per share being offered in cash, if
any, plus the value of any non-cash consideration, if any, being offered in such Fundamental
Transaction and (D) a remaining option time equal to the time between the date of the public
announcement of the applicable Fundamental Transaction and the Termination Date.

     d) Number of Warrant Shares. Simultaneously with any adjustment to the
Exercise Price pursuant to paragraph (a) of this Section 9, the number of Warrant Shares
that may be purchased upon exercise of this Warrant shall be increased or decreased
proportionately, so that after such adjustment the aggregate Exercise Price payable
hereunder for the adjusted number of Warrant Shares shall be the same as the aggregate
Exercise Price in effect immediately prior to such adjustment.

     e) Calculations. All calculations under this Section 9 shall be made
to the nearest cent or the nearest 1/100th of a share, as applicable. The number of shares
of Common Stock outstanding at any given time shall not include shares owned or held by or
for the account of the Company, and the disposition of any such shares shall be considered
an issue or sale of Common Stock.

     f) Notice of Adjustments. Upon the occurrence of each adjustment pursuant to
this Section 9, the Company at its expense will, at the written request of the
Holder, promptly compute such adjustment in accordance with the terms of this Warrant and
prepare a certificate setting forth such adjustment, including a statement of the adjusted

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Exercise Price and adjusted number or type of Warrant Shares or other securities
issuable upon exercise of this Warrant (as applicable), describing the transactions giving
rise to such adjustments and showing in detail the facts upon which such adjustment is
based. Upon written request, the Company will promptly deliver a copy of each such
certificate to the Holder and to the Company’s Transfer Agent.

     g) Notice of Corporate Events. If, while this Warrant is outstanding, the
Company (i) declares a dividend or any other distribution of cash, securities or other
property in respect of its Common Stock, including without limitation any granting of rights
or warrants to subscribe for or purchase any capital stock of the Company or any Subsidiary,
(ii) authorizes or approves, enters into any agreement contemplating or solicits stockholder
approval for any Fundamental Transaction or (iii) authorizes the voluntary dissolution,
liquidation or winding up of the affairs of the Company, then, except if such notice and the
contents thereof shall be deemed to constitute material non-public information, the Company
shall deliver to the Holder a notice describing the material terms and conditions of such
transaction at least 10 Trading Days prior to the applicable record or effective date on
which a Person would need to hold Common Stock in order to participate in or vote with
respect to such transaction, and the Company will take all reasonable steps to give Holder
the practical opportunity to exercise this Warrant prior to such time; provided, however ,
that the failure to deliver such notice or any defect therein shall not affect the validity
of the corporate action required to be described in such notice.

     10. Payment of Exercise Price. The Holder may pay the Exercise Price in one of the
following manners:

     (a) Cash Exercise. The Holder may deliver immediately available funds; or

     (b) Cashless Exercise. If an Exercise Notice is delivered at a time when a resale
registration statement on Form S-3 covering the resale of the Warrant Shares is not then effective,
then the Holder may notify the Company in an Exercise Notice of its election to utilize cashless
exercise, in which event the Company shall issue to the Holder the number of Warrant Shares
determined as follows:

     X = Y [(A-B)/A]

     where:

X = the number of Warrant Shares to be issued to the Holder.

Y = the number of Warrant Shares with respect to which this Warrant is being exercised.

A = the average of the Closing Prices for the five Trading Days immediately prior to (but not including) the Exercise Date.

B = the Exercise Price.

     For purposes of Rule 144 promulgated under the Securities Act, it is intended, understood and
acknowledged that the Warrant Shares issued in a cashless exercise transaction shall be

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deemed to have been acquired by the Holder, and the holding period for the Warrant Shares
shall be deemed to have commenced, on the date this Warrant was originally issued.

     If, but only if, at any time after the Original Issue Date there is no effective registration
statement registering the Warrant Shares, the Company shall use its best efforts to file a new
registration statement on Form S-3 pursuant to General Instruction I.B.4(a)(3) (including
compliance with General Instruction I.B.4(b) and I.B.4(c) as required thereby) registering the
Warrant Shares issuable upon exercise of the Warrant.

     11. Limitations on Exercise.

     (a) Notwithstanding anything to the contrary contained herein, the number of Warrant Shares
that may be acquired by the Holder upon any exercise of this Warrant (or otherwise in respect
hereof) shall be limited to the extent necessary to insure that, following such exercise (or other
issuance), the total number of shares of Common Stock then beneficially owned by such Holder and
its Affiliates and any other Persons whose beneficial ownership of Common Stock would be aggregated
with the Holder’s for purposes of Section 13(d) of the Exchange Act, does not exceed 4.999% of the
total number of issued and outstanding shares of Common Stock (including for such purpose the
shares of Common Stock issuable upon such exercise). For such purposes, beneficial ownership shall
be determined in accordance with Section 13(d) of the Exchange Act and the rules and regulations
promulgated thereunder. Each delivery of an Exercise Notice hereunder will constitute a
representation by the Holder that it has evaluated the limitation set forth in this Section and
determined that issuance of the full number of Warrant Shares requested in such Exercise Notice is
permitted under this Section. The Company’s obligation to issue shares of Common Stock in excess
of the limitation referred to in this Section shall be suspended (and, except as provided below,
shall not terminate or expire notwithstanding any contrary provisions hereof) until such time, if
any, as such shares of Common Stock may be issued in compliance with such limitation; provided,
that, if, as of 5:00 p.m., New York City time, on the Expiration Date, the Company has not received
written notice that the shares of Common Stock may be issued in compliance with such limitation,
the Company’s obligation to issue such shares shall terminate. This provision shall not restrict
the number of shares of Common Stock that a Holder may receive or beneficially own in order to
determine the amount of securities or other consideration that such Holder may receive in the event
of a Fundamental Transaction as contemplated in Section 9 of this Warrant. By written notice to
the Company, the Holder may waive the provisions of this Section but any such waiver will not be
effective until the 61st day after such notice is delivered to the Company, nor will any such
waiver effect any other Holder. This provision shall not apply to Holders who, together with
Affiliates, as of the Closing Date beneficially own (as determined in accordance with Section 13(d)
of the Exchange Act and the rules and regulations promulgated thereunder) in excess of 5% of the
total number of issued and outstanding shares of Common Stock.

     (b) Notwithstanding anything to the contrary contained herein, the number of Warrant Shares
that may be acquired by the Holder upon any exercise of this Warrant (or otherwise in respect
hereof) shall be limited to the extent necessary to insure that, following such exercise (or other
issuance), the total number of shares of Common Stock then beneficially owned by such Holder and
its Affiliates and any other Persons whose beneficial ownership of Common Stock would be aggregated
with the Holder’s for purposes of Section 13(d) of the

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Exchange Act, does not exceed 9.999% of the total number of issued and outstanding shares of
Common Stock (including for such purpose the shares of Common Stock issuable upon such exercise).
For such purposes, beneficial ownership shall be determined in accordance with Section 13(d) of the
Exchange Act and the rules and regulations promulgated thereunder. Each delivery of an Exercise
Notice hereunder will constitute a representation by the Holder that it has evaluated the
limitation set forth in this Section and determined that issuance of the full number of Warrant
Shares requested in such Exercise Notice is permitted under this Section. The Company’s obligation
to issue shares of Common Stock in excess of the limitation referred to in this Section shall be
suspended (and, except as provided below, shall not terminate or expire notwithstanding any
contrary provisions hereof) until such time, if any, as such shares of Common Stock may be issued
in compliance with such limitation; provided, that, if, as of 5:00 p.m., New York City time, on the
Expiration Date, the Company has not received written notice that the shares of Common Stock may be
issued in compliance with such limitation, the Company’s obligation to issue such shares shall
terminate. This provision shall not restrict the number of shares of Common Stock that a Holder
may receive or beneficially own in order to determine the amount of securities or other
consideration that such Holder may receive in the event of a Fundamental Transaction as
contemplated in Section 9 of this Warrant. This provision shall not apply to Holders who, together
with Affiliates, as of the Closing Date beneficially own (as determined in accordance with Section
13(d) of the Exchange Act and the rules and regulations promulgated thereunder) in excess of 10% of
the total number of issued and outstanding shares of Common Stock.

     12. No Fractional Shares. No fractional Warrant Shares will be issued in connection
with any exercise of this Warrant. In lieu of any fractional shares that would otherwise be
issuable, the Company shall pay cash equal to the product of such fraction multiplied by the
closing price of one Warrant Share as reported by the applicable Trading Market on the Exercise
Date.

     13. Notices. Any and all notices or other communications or deliveries hereunder
(including, without limitation, any Exercise Notice) shall be in writing and 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 at or prior to 5:00 p.m.
(New York City time) on a Trading Day, (ii) the next Trading Day after the date of transmission, if
such notice or communication is delivered via facsimile at the facsimile number specified in this
Section on a day that is not a Trading Day or later than 5:00 p.m. (New York City time) on any
Trading Day, (iii) the Trading 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. The addresses for such notices or communications shall be: if to the Company, to
Emisphere Technologies, Inc., 240 Cedar Knolls Road, Suite 200, Cedar Knolls, New Jersey 07927.
Attention: Chief Executive Officer, Facsimile No.: (973) 532-8121 (or such other address as the
Company shall indicate in writing in accordance with this Section) or (ii) if to the Holder, to the
address or facsimile number appearing on the Warrant Register (or such other address as the Company
shall indicate in writing in accordance with this Section).

     14. Warrant Agent. The Company shall serve as warrant agent under this Warrant. Upon
30 days’ notice to the Holder, the Company may appoint a new warrant agent. Any

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corporation into which the Company or any new warrant agent may be merged or any corporation
resulting from any consolidation to which the Company or any new warrant agent shall be a party or
any corporation to which the Company or any new warrant agent transfers substantially all of its
corporate trust or shareholders services business shall be a successor warrant agent under this
Warrant without any further act. Any such successor warrant agent shall promptly cause notice of
its succession as warrant agent to be mailed (by first class mail, postage prepaid) to the Holder
at the Holder’s last address as shown on the Warrant Register.

     15. Miscellaneous.

     (a) This Warrant shall be binding on and inure to the benefit of the parties hereto and their
respective successors and assigns. Subject to the preceding sentence, nothing in this Warrant
shall be construed to give to any Person other than the Company and the Holder any legal or
equitable right, remedy or cause of action under this Warrant. This Warrant may be amended only in
writing signed by the Company and the Holder, or their successors and assigns.

     (b) All questions concerning the construction, validity, enforcement and interpretation of
this Warrant shall be governed by and construed and enforced in accordance with the internal laws
of the State of New York, without regard to the principles of conflicts of law thereof. Each party
agrees that all legal proceedings concerning the interpretations, enforcement and defense of this
Warrant and the transactions herein contemplated (“Proceedings”) (whether brought against a
party hereto or its respective Affiliates, employees or agents) shall be commenced exclusively in
the New York Courts. Each party hereto hereby irrevocably submits to the exclusive jurisdiction of
the New York Courts for the adjudication of any dispute hereunder or in connection herewith or with
any transaction contemplated hereby or discussed herein, and hereby irrevocably waives, and agrees
not to assert in any Proceeding, any claim that it is not personally subject to the jurisdiction of
any New York Court, or that such Proceeding has been commenced in an improper or inconvenient
forum. Each party hereto hereby irrevocably waives personal service of process and consents to
process being served in any such Proceeding by mailing a copy thereof via registered or certified
mail or overnight delivery (with evidence of delivery) to such party at the address in effect for
notices to it under this Warrant and agrees that such service shall constitute good and sufficient
service of process and notice thereof. Nothing contained herein shall be deemed to limit in any
way any right to serve process in any manner permitted by law. Each party hereto hereby
irrevocably waives, to the fullest extent permitted by applicable law, any and all right to trial
by jury in any legal proceeding arising out of or relating to this Warrant or the transactions
contemplated hereby. If either party shall commence a Proceeding to enforce any provisions of this
Warrant, then the prevailing party in such Proceeding shall be reimbursed by the other party for
its attorney’s fees and other costs and expenses incurred with the investigation, preparation and
prosecution of such Proceeding.

     (c) The headings herein are for convenience only, do not constitute a part of this Warrant and
shall not be deemed to limit or affect any of the provisions hereof.

     (d) In case any one or more of the provisions of this Warrant shall be invalid or
unenforceable in any respect, the validity and enforceability of the remaining terms and provisions
of this Warrant shall not in any way be affected or impaired thereby and the parties

10

 

will attempt in good faith to agree upon a valid and enforceable provision which shall be a
commercially reasonable substitute therefore, and upon so agreeing, shall incorporate such
substitute provision in this Warrant.

     (e) Prior to exercise of this Warrant, the Holder hereof shall not, by reason of by being a
Holder, be entitled to any rights of a stockholder with respect to the Warrant Shares.

[REMAINDER OF PAGE INTENTIONALLY LEFT BLANK,

SIGNATURE PAGE FOLLOWS]

11

 

     IN WITNESS WHEREOF, the Company has caused this Warrant to be duly executed by its authorized
officer as of the date first indicated above.

	 	 	 	 	 
	 	EMISPHERE TECHNOLOGIES, INC.

 	 
	 	By:  	/s/
Michael R. Garone
 	 
	 	 	Name:  	Michael R. Garone 	 
	 	 	Title:  	Chief Financial Officer 	 

12

 

	 	 	 	 	 

EXERCISE NOTICE

EMISPHERE TECHNOLOGIES, INC.

WARRANT NO. A-26 DATED AUGUST 21, 2009

Ladies and Gentlemen:

     (1) The undersigned hereby elects to exercise the above-referenced Warrant with respect to
shares of Common Stock. Capitalized terms used herein and not otherwise defined herein have the
respective meanings set forth in the Warrant.

     (2) The Holder intends that payment of the Exercise Price shall be made as (check one):

	 	•	 	Cash Exercise under Section 10(a)
	 
	 	•	 	Cashless Exercise under Section 10(b)

     (3) If the Holder has elected a Cash Exercise, the holder
 shall pay the sum of $___________to the Company in accordance with the terms of the Warrant.

     (4) Pursuant to this Exercise Notice, the Company shall deliver to the Holder the number of
Warrant Shares determined in accordance with the terms of the Warrant.

     (5) By its delivery of this Exercise Notice, the undersigned represents and warrants to the
Company that in giving effect to the exercise evidenced hereby the Holder will not beneficially own
in excess of the number of shares of Common Stock (as determined in accordance with Section 13(d)
of the Securities Exchange Act of 1934) permitted to be owned under Section 11 of this Warrant to
which this notice relates.

	 	 	 	 	 	 	 
	 	 	HOLDER	 	 
	 
	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	 
	 	 	(Print name)	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

	 	 
	 

	 	Title:	 	 	 	 
	 

	 	 	 	 

	 	 

13

 

WARRANT ORIGINALLY ISSUED AUGUST 21, 2009

WARRANT NO. A-26

FORM OF ASSIGNMENT

To be completed and signed only upon transfer of Warrant

     FOR VALUE RECEIVED, the
 undersigned hereby sells, assigns and transfers unto ___________
the right represented by the within Warrant to purchase ___________shares of Common
Stock to which the within Warrant relates and appoints ___________attorney to transfer said
right on the books of the Company with full power of substitution in the premises.

	 	 	 	 	 	 	 	 	 
	Dated:

	 	 	 	TRANSFEROR:	 	 
	 

	 	 

	 	 	 	 	 	 
	 	 	 	 	 	 	 
	 	 	 	 	(Print name)	 	 
	 
	 	 	 	 	 	 	 	 
	 

	 	 	 	By:
	 	 

	 	 
	 
	 	 	 	 	 	 	 	 
	 

	 	 	 	Title:
	 	 

	 	 
	 
	 	 	 	 	 	 	 	 
	 

	 	 	 	TRANSFEREE:	 	 
	 
	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 
	 	 	 	 	(Print name)	 	 
	 
	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 
	 	 	 	 	(Address of Transferee)	 	 
	 
	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	In the presence of:
	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 

14exv10w8

Exhibit 10.8

THIS WARRANT AND THE SECURITIES ISSUABLE UPON EXERCISE HEREOF HAVE NOT BEEN REGISTERED UNDER THE
SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), OR ANY OTHER SECURITIES LAWS AND MAY NOT
BE OFFERED FOR SALE, SOLD, TRANSFERRED, PLEDGED OR HYPOTHECATED IN THE ABSENCE OF (1) AN EFFECTIVE
REGISTRATION STATEMENT COVERING SUCH SECURITIES UNDER THE SECURITIES ACT AND ANY OTHER APPLICABLE
SECURITIES LAWS, OR (2) AN OPINION OF COUNSEL REASONABLY SATISFACTORY TO THE COMPANY THAT SUCH
REGISTRATION IS NOT REQUIRED.

EMISPHERE TECHNOLOGIES, INC.

WARRANT

	 	 	 	 	 
	Warrant No. A-27
	 	Original Issue Date: August 21, 2009

     EMISPHERE TECHNOLOGIES, INC., a Delaware corporation (the “Company”), hereby certifies
that, for value received, MHR Institutional Partners II LP or its permitted registered assigns (the
“Holder”), is entitled to purchase from the Company up to a total of 818,011 shares of
common stock, $0.01 par value (the “Common Stock”), of the Company (each such share, a
“Warrant Share” and all such shares, the “Warrant Shares”) at an exercise price
equal to $0.70 per share (as adjusted from time to time as provided herein, the “Exercise
Price”), at any time and from time to time on or after the Original Issue Date and through and
including August 21, 2014 (the “Expiration Date” ), and subject to the following terms and
conditions:

     This Warrant is one of a series of warrants issued pursuant to that certain Securities
Purchase Agreement dated August 19, 2009, by and between the Company and each the purchasers
identified therein (the “Purchase Agreement”). All such warrants are referred to herein,
collectively, as the “Warrants.”

     1. Definitions. In addition to the terms defined elsewhere in this Warrant,
capitalized terms that are not otherwise defined herein have the meanings given to such terms in
the Purchase Agreement.

     2. List of Warrant Holders. The Company shall register this Warrant, upon records to
be maintained by the Company for that purpose (the “Warrant Register”), in the name of the
record Holder (which shall include the initial Holder or, as the case may be, any registered
assignee to which this Warrant is permissibly assigned hereunder from time to time). The Company
may deem and treat the registered Holder of this Warrant as the absolute owner hereof for the
purpose of any exercise hereof or any distribution to the Holder, and for all other purposes,
absent actual notice to the contrary.

 

 

     3. List of Transfers; Restrictions on Transfer.

     (a) This Warrant and the Warrant Shares are subject to the restrictions on transfer set forth
in this Section 3.

     (b) The Company shall register any such transfer of all or any portion of this Warrant in the
Warrant Register, upon surrender of this Warrant, with the Form of Assignment attached hereto duly
completed and signed, to the Company at its address specified herein. Upon any such registration
or transfer, a new Warrant to purchase Common Stock, in substantially the form of this Warrant (any
such new Warrant, a “New Warrant”), evidencing the portion of this Warrant so transferred
shall be issued to the transferee and a New Warrant evidencing the remaining portion of this
Warrant not so transferred, if any, shall be issued to the transferring Holder. The acceptance of
the New Warrant by the transferee thereof shall be deemed the acceptance by such transferee of all
of the rights and obligations in respect of the New Warrant that the Holder has in respect of this
Warrant.

     (c) If, but only if, at the time of the surrender of this Warrant in connection with any
transfer of this Warrant, the Holder is an Affiliate of the Company, and transfer of this Warrant
shall not be registered pursuant to an effective registration statement under the Securities Act
and under applicable state securities or blue sky laws, the Company may require, as a condition of
allowing such transfer (i) that the Holder or transferee of this Warrant, as the case may be,
furnish to the Company a written opinion of counsel (which opinion shall be in form, substance and
scope customary for opinions of counsel in comparable transactions) to the effect that such
transfer may be made without registration under the Securities Act and under applicable state
securities or blue sky laws, (ii) that the holder or transferee execute and deliver to the Company
an investment letter in form and substance acceptable to the Company and (iii) that the transferee
be an “accredited investor” as defined in Rule 501(a) promulgated under the Securities Act.

     4. Exercise and Duration of Warrants.

     (a) All or any part of this Warrant shall be exercisable by the registered Holder in any
manner permitted by Section 10 of this Warrant at any time and from time to time on or after the
Original Issue Date and through and including the Expiration Date. Subject to Section 11 hereof,
at 5:00 p.m., New York City time, on the Expiration Date, the portion of this Warrant not exercised
prior thereto shall be and become void and of no value and this Warrant shall be terminated and no
longer outstanding. In addition, if cashless exercise would be permitted under Section 10(b) of
this Warrant, then all or part of this Warrant may be exercised by the registered Holder utilizing
such cashless exercise provisions at any time, or from time to time, on or after the Original Issue
Date and through and including the Expiration Date.

     (b) The Holder may exercise this Warrant by delivering to the Company (i) an exercise notice,
in the form attached hereto (the “Exercise Notice”), completed and duly signed, and (ii) if
such Holder is not utilizing the cashless exercise provisions set forth in this Warrant, payment of
the Exercise Price for the number of Warrant Shares as to which this Warrant is being exercised.
The date such items are delivered to the Company (as determined in accordance with the notice
provisions hereof) is an “Exercise Date.” The Holder shall not be required to

2

 

deliver the original Warrant in order to effect an exercise hereunder. Execution and delivery
of the Exercise Notice shall have the same effect as cancellation of the original Warrant and
issuance of a New Warrant evidencing the right to purchase the remaining number of Warrant Shares.
Additionally, at the request of the Holder, if this Warrant shall have been exercised in part and
the Holder shall have surrendered this Warrant certificate, the Company shall, at the time of
delivery of the certificate or certificates representing Warrant Shares, deliver to Holder a new
Warrant evidencing the rights of Holder to purchase the unpurchased Warrant Shares called for by
this Warrant, which new Warrant shall in all other respects be identical with this Warrant.

     5. Delivery of Warrant Shares.

     (a) Upon exercise of this Warrant, the Company shall promptly (but in no event later than
three Trading Days after the Exercise Date) issue or cause to be issued and cause to be delivered
to or upon the written order of the Holder and in such name or names as the Holder may designate
(provided that, if a registration statement is not then effective and the Holder directs the
Company to deliver a certificate for the Warrant Shares in a name other than that of the Holder or
an Affiliate of the Holder, it shall deliver to the Company on the Exercise Date an opinion of
counsel reasonably satisfactory to the Company to the effect that the issuance of such Warrant
Shares in such other name may be made pursuant to an available exemption from the registration
requirements of the Securities Act and all applicable state securities or blue sky laws), a
certificate for the Warrant Shares issuable upon such exercise, free of restrictive legends unless
a registration statement is not then effective or the Warrant Shares are not freely transferable
without volume restrictions or current public information requirements pursuant to Rule 144 under
the Securities Act. The Holder, or any Person permissibly so designated by the Holder to receive
Warrant Shares, shall be deemed to have become the holder of record of such Warrant Shares as of
the Exercise Date. If the Warrant Shares can be issued without restrictive legends, the Company
shall, upon the written request of the Holder, use its best efforts to deliver, or cause to be
delivered, Warrant Shares hereunder electronically through the Depository Trust and Clearing
Corporation DWAC system or another established clearing corporation performing similar functions,
if available; provided, that, the Company may, but will not be required to, change its transfer
agent if its current transfer agent cannot deliver Warrant Shares electronically through the
Depository Trust and Clearing Corporation.

     (b) If by the close of the third Trading Day after delivery of an Exercise Notice, the Company
fails to deliver to the Holder a certificate representing the required number of Warrant Shares in
the manner required pursuant to Section 5(a), and if after such third Trading Day and prior to the
receipt of such Warrant Shares, the Holder purchases (in an open market transaction or otherwise)
shares of Common Stock to deliver in satisfaction of a sale by the Holder of the Warrant Shares
which the Holder anticipated receiving upon such exercise (a “Buy-In”), then the Company
shall, within three Trading Days after the Holder’s request and in the Holder’s sole discretion,
either (1) pay in cash to the Holder an amount equal to the Holder’s total purchase price
(including brokerage commissions, if any) for the shares of Common Stock so purchased (the
“Buy-In Price”), at which point the Company’s obligation to deliver such certificate (and
to issue such Warrant Shares) shall terminate or (ii) promptly honor its obligation to deliver to
the Holder a certificate or certificates representing such Warrant Shares and pay cash to the
Holder in an amount equal to the excess (if any) of the Buy-In Price over the product of (A) such
number of Warrant Shares, times (B) the closing bid price on the date of the event giving rise to the Company’s obligation to deliver such certificate.

3

 

     (c) To the extent permitted by law, the Company’s obligations to issue and deliver Warrant
Shares in accordance with the terms hereof are absolute and unconditional, irrespective of any
action or inaction by the 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 the Holder or any other Person of any obligation to the Company or any violation or
alleged violation of law by the Holder or any other Person, and irrespective of any other
circumstance that might otherwise limit such obligation of the Company to the Holder in connection
with the issuance of Warrant Shares. 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 Company’s failure to
timely deliver certificates representing shares of Common Stock upon exercise of the Warrant as
required pursuant to the terms hereof.

     6. Charges, Taxes and Expenses. Issuance and delivery of certificates for shares of
Common Stock upon exercise of this Warrant shall be made without charge to the Holder for any issue
or transfer tax, withholding tax, transfer agent fee or other incidental tax or expense in respect
of the issuance of such certificates, all of which taxes and expenses shall be paid by the Company;
provided, however, that the Company shall not be required to pay any tax that may be payable in
respect of any transfer involved in the registration of any certificates for Warrant Shares or
Warrants in a name other than that of the Holder. The Holder shall be responsible for all other
tax liability that may arise as a result of holding or transferring this Warrant or receiving
Warrant Shares upon exercise hereof.

     7. Replacement of Warrant. If this Warrant is mutilated, lost, stolen or destroyed,
the Company shall issue or cause to be issued in exchange and substitution for and upon
cancellation hereof, or in lieu of and substitution for this Warrant, a New Warrant, but only upon
receipt of evidence reasonably satisfactory to the Company of such loss, theft or destruction and
customary and reasonable indemnity (which shall not include a surety bond), if requested.
Applicants for a New Warrant under such circumstances shall also comply with such other reasonable
regulations and procedures and pay such other reasonable third-party costs as the Company may
prescribe. If a New Warrant is requested as a result of a mutilation of this Warrant, then the
Holder shall deliver such mutilated Warrant to the Company as a condition precedent to the
Company’s obligation to issue the New Warrant.

     8. Reservation of Warrant Shares. The Company covenants that it will at all times
reserve and keep available out of the aggregate of its authorized but unissued and otherwise
unreserved Common Stock, solely for the purpose of enabling it to issue Warrant Shares upon
exercise of this Warrant as herein provided, the number of Warrant Shares that are then issuable
and deliverable upon the exercise of this entire Warrant, free from preemptive rights or any other
contingent purchase rights of persons other than the Holder (taking into account the adjustments
and restrictions of Section 9). The Company covenants that all Warrant Shares so issuable and
deliverable shall, upon issuance and the payment of the applicable Exercise Price in accordance
with the terms hereof, be duly and validly authorized, issued and fully paid and nonassessable.

4

 

     9. Certain Adjustments. The Exercise Price and number of Warrant Shares issuable upon
exercise of this Warrant are subject to adjustment from time to time as set forth in this Section
9.

     a) Stock Dividends and Splits. If the Company, at any time while this Warrant
is outstanding, (i) pays a stock dividend on its Common Stock or otherwise makes a
distribution on any class of capital stock that is payable in shares of Common Stock, (ii)
subdivides outstanding shares of Common Stock into a larger number of shares, or (iii)
combines outstanding shares of Common Stock into a smaller number of shares, then in each
such case the Exercise Price shall be multiplied by a fraction of which the numerator shall
be the number of shares of Common Stock outstanding immediately before such event and of
which the denominator shall be the number of shares of Common Stock outstanding immediately
after such event. Any adjustment made pursuant to clause (i) of this paragraph shall become
effective immediately after the record date for the determination of stockholders entitled
to receive such dividend or distribution, and any adjustment pursuant to clause (ii) or
(iii) of this paragraph shall become effective immediately after the effective date of such
subdivision or combination.

     b) Pro Rata Distributions. If the Company, at any time while this Warrant is
outstanding, distributes to all holders of Common Stock for no consideration (i) evidences
of its indebtedness, (ii) any security (other than a distribution of Common Stock covered by
the preceding paragraph), (iii) rights or warrants to subscribe for or purchase any
security, or (iv) any other asset (in each case, “Distributed Property”), then, upon
any exercise of this Warrant that occurs after the record date fixed for determination of
stockholders entitled to receive such distribution, the Holder shall be entitled to receive,
in addition to the Warrant Shares otherwise issuable upon such exercise (if applicable), the
Distributed Property that such Holder would have been entitled to receive in respect of such
number of Warrant Shares had the Holder been the record holder of such Warrant Shares
immediately prior to such record date.

     c) Fundamental Transactions. If, at any time while this Warrant is outstanding
(i) the Company effects any merger or consolidation of the Company with or into another
Person, in which the shareholders of the Company as of immediately prior to the transaction
own less than a majority of the outstanding stock of the surviving entity, (ii) the Company
effects any sale of all or substantially all of its assets in one or a series of related
transactions, (iii) any tender offer or exchange offer (whether by the Company or another
Person) is completed pursuant to which holders of Common Stock are permitted to tender or
exchange their shares for other securities, cash or property, or (iv) the Company effects
any reclassification of the Common Stock or any compulsory share exchange pursuant to which
the Common Stock is effectively converted into or exchanged for other securities, cash or
property (each, a “Fundamental Transaction”), then the Holder shall have the right
thereafter to receive, upon exercise of this Warrant, the same amount and kind 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 the number of Warrant Shares then issuable upon exercise in full
of this Warrant (the “Alternate Consideration”). The

5

 

Company shall not effect any such Fundamental Transaction unless prior to or
simultaneously with the consummation thereof, any successor to the Company, surviving entity
or the corporation purchasing or otherwise acquiring such assets or other appropriate
corporation or entity shall assume the obligation to deliver to the Holder, such Alternate
Consideration as, in accordance with the foregoing provisions, the Holder may be entitled to
purchase, and the other obligations under this Warrant. The provisions of this paragraph
(c) shall similarly apply to subsequent transactions analogous to a Fundamental Transaction.
Notwithstanding anything to the contrary, in the event of a Fundamental Transaction that is
(1) an all cash transaction or (2) a “Rule 13e-3 transaction” as defined in Rule 13e-3 under
the Exchange Act, the Company or any Successor Entity (as defined below) shall, at the
Holder’s option, exercisable at any time concurrently with, or within 30 days after, the
consummation of the Fundamental Transaction, purchase this Warrant from the Holder by paying
to the Holder an amount of cash equal to the Black Scholes Value of the remaining
unexercised portion of this Warrant on the date of the consummation of such Fundamental
Transaction. “Black Scholes Value” means the value of this Warrant based on the
Black and Scholes Option Pricing Model obtained from the “OV” function on Bloomberg, L.P.
(“Bloomberg”) determined as of the day of consummation of the applicable Fundamental
Transaction for pricing purposes and reflecting (A) a risk-free interest rate corresponding
to the U.S. Treasury rate for a period equal to the time between the date of the public
announcement of the applicable Fundamental Transaction and the Termination Date, (B) an
expected volatility equal to the greater of 100% and the 100 day volatility obtained from
the HVT function on Bloomberg as of the Trading Day immediately following the public
announcement of the applicable Fundamental Transaction, (C) the underlying price per share
used in such calculation shall be the sum of the price per share being offered in cash, if
any, plus the value of any non-cash consideration, if any, being offered in such Fundamental
Transaction and (D) a remaining option time equal to the time between the date of the public
announcement of the applicable Fundamental Transaction and the Termination Date.

     d) Number of Warrant Shares. Simultaneously with any adjustment to the
Exercise Price pursuant to paragraph (a) of this Section 9, the number of Warrant Shares
that may be purchased upon exercise of this Warrant shall be increased or decreased
proportionately, so that after such adjustment the aggregate Exercise Price payable
hereunder for the adjusted number of Warrant Shares shall be the same as the aggregate
Exercise Price in effect immediately prior to such adjustment.

     e) Calculations. All calculations under this Section 9 shall be made
to the nearest cent or the nearest 1/100th of a share, as applicable. The number of shares
of Common Stock outstanding at any given time shall not include shares owned or held by or
for the account of the Company, and the disposition of any such shares shall be considered
an issue or sale of Common Stock.

     f) Notice of Adjustments. Upon the occurrence of each adjustment pursuant to
this Section 9, the Company at its expense will, at the written request of the
Holder, promptly compute such adjustment in accordance with the terms of this Warrant and
prepare a certificate setting forth such adjustment, including a statement of the adjusted

6

 

Exercise Price and adjusted number or type of Warrant Shares or other securities
issuable upon exercise of this Warrant (as applicable), describing the transactions giving
rise to such adjustments and showing in detail the facts upon which such adjustment is
based. Upon written request, the Company will promptly deliver a copy of each such
certificate to the Holder and to the Company’s Transfer Agent.

     g) Notice of Corporate Events. If, while this Warrant is outstanding, the
Company (i) declares a dividend or any other distribution of cash, securities or other
property in respect of its Common Stock, including without limitation any granting of rights
or warrants to subscribe for or purchase any capital stock of the Company or any Subsidiary,
(ii) authorizes or approves, enters into any agreement contemplating or solicits stockholder
approval for any Fundamental Transaction or (iii) authorizes the voluntary dissolution,
liquidation or winding up of the affairs of the Company, then, except if such notice and the
contents thereof shall be deemed to constitute material non-public information, the Company
shall deliver to the Holder a notice describing the material terms and conditions of such
transaction at least 10 Trading Days prior to the applicable record or effective date on
which a Person would need to hold Common Stock in order to participate in or vote with
respect to such transaction, and the Company will take all reasonable steps to give Holder
the practical opportunity to exercise this Warrant prior to such time; provided, however ,
that the failure to deliver such notice or any defect therein shall not affect the validity
of the corporate action required to be described in such notice.

     10. Payment of Exercise Price. The Holder may pay the Exercise Price in one of the
following manners:

     (a) Cash Exercise. The Holder may deliver immediately available funds; or

     (b) Cashless Exercise. If an Exercise Notice is delivered at a time when a resale
registration statement on Form S-3 covering the resale of the Warrant Shares is not then effective,
then the Holder may notify the Company in an Exercise Notice of its election to utilize cashless
exercise, in which event the Company shall issue to the Holder the number of Warrant Shares
determined as follows:

     X = Y [(A-B)/A]

   where:

X = the number of Warrant Shares to be issued to the Holder.

Y = the number of Warrant Shares with respect to which this Warrant is being exercised.

A = the average of the Closing Prices for the five Trading Days immediately prior to (but not including) the Exercise Date.

B = the Exercise Price.

     For purposes of Rule 144 promulgated under the Securities Act, it is intended, understood and
acknowledged that the Warrant Shares issued in a cashless exercise transaction shall be

7

 

deemed to have been acquired by the Holder, and the holding period for the Warrant Shares
shall be deemed to have commenced, on the date this Warrant was originally issued.

     If, but only if, at any time after the Original Issue Date there is no effective registration
statement registering the Warrant Shares, the Company shall use its best efforts to file a new
registration statement on Form S-3 pursuant to General Instruction I.B.4(a)(3) (including
compliance with General Instruction I.B.4(b) and I.B.4(c) as required thereby) registering the
Warrant Shares issuable upon exercise of the Warrant.

     11. Limitations on Exercise.

     (a) Notwithstanding anything to the contrary contained herein, the number of Warrant Shares
that may be acquired by the Holder upon any exercise of this Warrant (or otherwise in respect
hereof) shall be limited to the extent necessary to insure that, following such exercise (or other
issuance), the total number of shares of Common Stock then beneficially owned by such Holder and
its Affiliates and any other Persons whose beneficial ownership of Common Stock would be aggregated
with the Holder’s for purposes of Section 13(d) of the Exchange Act, does not exceed 4.999% of the
total number of issued and outstanding shares of Common Stock (including for such purpose the
shares of Common Stock issuable upon such exercise). For such purposes, beneficial ownership shall
be determined in accordance with Section 13(d) of the Exchange Act and the rules and regulations
promulgated thereunder. Each delivery of an Exercise Notice hereunder will constitute a
representation by the Holder that it has evaluated the limitation set forth in this Section and
determined that issuance of the full number of Warrant Shares requested in such Exercise Notice is
permitted under this Section. The Company’s obligation to issue shares of Common Stock in excess
of the limitation referred to in this Section shall be suspended (and, except as provided below,
shall not terminate or expire notwithstanding any contrary provisions hereof) until such time, if
any, as such shares of Common Stock may be issued in compliance with such limitation; provided,
that, if, as of 5:00 p.m., New York City time, on the Expiration Date, the Company has not received
written notice that the shares of Common Stock may be issued in compliance with such limitation,
the Company’s obligation to issue such shares shall terminate. This provision shall not restrict
the number of shares of Common Stock that a Holder may receive or beneficially own in order to
determine the amount of securities or other consideration that such Holder may receive in the event
of a Fundamental Transaction as contemplated in Section 9 of this Warrant. By written notice to
the Company, the Holder may waive the provisions of this Section but any such waiver will not be
effective until the 61st day after such notice is delivered to the Company, nor will any such
waiver effect any other Holder. This provision shall not apply to Holders who, together with
Affiliates, as of the Closing Date beneficially own (as determined in accordance with Section 13(d)
of the Exchange Act and the rules and regulations promulgated thereunder) in excess of 5% of the
total number of issued and outstanding shares of Common Stock.

     (b) Notwithstanding anything to the contrary contained herein, the number of Warrant Shares
that may be acquired by the Holder upon any exercise of this Warrant (or otherwise in respect
hereof) shall be limited to the extent necessary to insure that, following such exercise (or other
issuance), the total number of shares of Common Stock then beneficially owned by such Holder and
its Affiliates and any other Persons whose beneficial ownership of Common Stock would be aggregated
with the Holder’s for purposes of Section 13(d) of the

8

 

Exchange Act, does not exceed 9.999% of the total number of issued and outstanding shares of
Common Stock (including for such purpose the shares of Common Stock issuable upon such exercise).
For such purposes, beneficial ownership shall be determined in accordance with Section 13(d) of the
Exchange Act and the rules and regulations promulgated thereunder. Each delivery of an Exercise
Notice hereunder will constitute a representation by the Holder that it has evaluated the
limitation set forth in this Section and determined that issuance of the full number of Warrant
Shares requested in such Exercise Notice is permitted under this Section. The Company’s obligation
to issue shares of Common Stock in excess of the limitation referred to in this Section shall be
suspended (and, except as provided below, shall not terminate or expire notwithstanding any
contrary provisions hereof) until such time, if any, as such shares of Common Stock may be issued
in compliance with such limitation; provided, that, if, as of 5:00 p.m., New York City time, on the
Expiration Date, the Company has not received written notice that the shares of Common Stock may be
issued in compliance with such limitation, the Company’s obligation to issue such shares shall
terminate. This provision shall not restrict the number of shares of Common Stock that a Holder
may receive or beneficially own in order to determine the amount of securities or other
consideration that such Holder may receive in the event of a Fundamental Transaction as
contemplated in Section 9 of this Warrant. This provision shall not apply to Holders who, together
with Affiliates, as of the Closing Date beneficially own (as determined in accordance with Section
13(d) of the Exchange Act and the rules and regulations promulgated thereunder) in excess of 10% of
the total number of issued and outstanding shares of Common Stock.

     12. No Fractional Shares. No fractional Warrant Shares will be issued in connection
with any exercise of this Warrant. In lieu of any fractional shares that would otherwise be
issuable, the Company shall pay cash equal to the product of such fraction multiplied by the
closing price of one Warrant Share as reported by the applicable Trading Market on the Exercise
Date.

     13. Notices. Any and all notices or other communications or deliveries hereunder
(including, without limitation, any Exercise Notice) shall be in writing and 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 at or prior to 5:00 p.m.
(New York City time) on a Trading Day, (ii) the next Trading Day after the date of transmission, if
such notice or communication is delivered via facsimile at the facsimile number specified in this
Section on a day that is not a Trading Day or later than 5:00 p.m. (New York City time) on any
Trading Day, (iii) the Trading 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. The addresses for such notices or communications shall be: if to the Company, to
Emisphere Technologies, Inc., 240 Cedar Knolls Road, Suite 200, Cedar Knolls, New Jersey 07927.
Attention: Chief Executive Officer, Facsimile No.: (973) 532-8121 (or such other address as the
Company shall indicate in writing in accordance with this Section) or (ii) if to the Holder, to the
address or facsimile number appearing on the Warrant Register (or such other address as the Company
shall indicate in writing in accordance with this Section).

     14. Warrant Agent. The Company shall serve as warrant agent under this Warrant. Upon
30 days’ notice to the Holder, the Company may appoint a new warrant agent. Any

9

 

corporation into which the Company or any new warrant agent may be merged or any corporation
resulting from any consolidation to which the Company or any new warrant agent shall be a party or
any corporation to which the Company or any new warrant agent transfers substantially all of its
corporate trust or shareholders services business shall be a successor warrant agent under this
Warrant without any further act. Any such successor warrant agent shall promptly cause notice of
its succession as warrant agent to be mailed (by first class mail, postage prepaid) to the Holder
at the Holder’s last address as shown on the Warrant Register.

     15. Miscellaneous.

     (a) This Warrant shall be binding on and inure to the benefit of the parties hereto and their
respective successors and assigns. Subject to the preceding sentence, nothing in this Warrant
shall be construed to give to any Person other than the Company and the Holder any legal or
equitable right, remedy or cause of action under this Warrant. This Warrant may be amended only in
writing signed by the Company and the Holder, or their successors and assigns.

     (b) All questions concerning the construction, validity, enforcement and interpretation of
this Warrant shall be governed by and construed and enforced in accordance with the internal laws
of the State of New York, without regard to the principles of conflicts of law thereof. Each party
agrees that all legal proceedings concerning the interpretations, enforcement and defense of this
Warrant and the transactions herein contemplated (“Proceedings”) (whether brought against a
party hereto or its respective Affiliates, employees or agents) shall be commenced exclusively in
the New York Courts. Each party hereto hereby irrevocably submits to the exclusive jurisdiction of
the New York Courts for the adjudication of any dispute hereunder or in connection herewith or with
any transaction contemplated hereby or discussed herein, and hereby irrevocably waives, and agrees
not to assert in any Proceeding, any claim that it is not personally subject to the jurisdiction of
any New York Court, or that such Proceeding has been commenced in an improper or inconvenient
forum. Each party hereto hereby irrevocably waives personal service of process and consents to
process being served in any such Proceeding by mailing a copy thereof via registered or certified
mail or overnight delivery (with evidence of delivery) to such party at the address in effect for
notices to it under this Warrant and agrees that such service shall constitute good and sufficient
service of process and notice thereof. Nothing contained herein shall be deemed to limit in any
way any right to serve process in any manner permitted by law. Each party hereto hereby
irrevocably waives, to the fullest extent permitted by applicable law, any and all right to trial
by jury in any legal proceeding arising out of or relating to this Warrant or the transactions
contemplated hereby. If either party shall commence a Proceeding to enforce any provisions of this
Warrant, then the prevailing party in such Proceeding shall be reimbursed by the other party for
its attorney’s fees and other costs and expenses incurred with the investigation, preparation and
prosecution of such Proceeding.

     (c) The headings herein are for convenience only, do not constitute a part of this Warrant and
shall not be deemed to limit or affect any of the provisions hereof.

     (d) In case any one or more of the provisions of this Warrant shall be invalid or
unenforceable in any respect, the validity and enforceability of the remaining terms and provisions
of this Warrant shall not in any way be affected or impaired thereby and the parties

10

 

will attempt in good faith to agree upon a valid and enforceable provision which shall be a
commercially reasonable substitute therefore, and upon so agreeing, shall incorporate such
substitute provision in this Warrant.

     (e) Prior to exercise of this Warrant, the Holder hereof shall not, by reason of by being a
Holder, be entitled to any rights of a stockholder with respect to the Warrant Shares.

[REMAINDER OF PAGE INTENTIONALLY LEFT BLANK,

SIGNATURE PAGE FOLLOWS]

11

 

          IN WITNESS WHEREOF, the Company has caused this Warrant to be duly executed by its authorized
officer as of the date first indicated above.

	 	 	 	 	 
	 	EMISPHERE TECHNOLOGIES, INC.

 	 
	 	By:  	/s/
Michael R. Garone 	 
	 	 	Name:  	Michael R. Garone 	 
	 	 	Title:  	Chief Financial Officer 	 

12

 

	 	 	 	 	 

EXERCISE NOTICE

EMISPHERE TECHNOLOGIES, INC.

WARRANT NO. A-27 DATED AUGUST 21, 2009

Ladies and Gentlemen:

     (1) The undersigned hereby elects to exercise the above-referenced Warrant with respect to
shares of Common Stock. Capitalized terms used herein and not otherwise defined herein have the
respective meanings set forth in the Warrant.

     (2) The Holder intends that payment of the Exercise Price shall be made as (check one):

	 	•	 	Cash Exercise under Section 10(a)
	 
	 	•	 	Cashless Exercise under Section 10(b)

     (3) If the Holder has elected a Cash Exercise, the holder shall pay the sum of $                    
to the Company in accordance with the terms of the Warrant.

     (4) Pursuant to this Exercise Notice, the Company shall deliver to the Holder the number of
Warrant Shares determined in accordance with the terms of the Warrant.

     (5) By its delivery of this Exercise Notice, the undersigned represents and warrants to the
Company that in giving effect to the exercise evidenced hereby the Holder will not beneficially own
in excess of the number of shares of Common Stock (as determined in accordance with Section 13(d)
of the Securities Exchange Act of 1934) permitted to be owned under Section 11 of this Warrant to
which this notice relates.

	 	 	 	 	 
	 
	 	HOLDER	 	 
	 
	 	 	 
	 	 	(Print name)
	 
	 	 	 	 
	 
	 	By:	 	 
	 	 	 	 	 
	 
	 	 	 	 
	 
	 	Title:	 	 
	 	 	 	 	 

13

 

WARRANT ORIGINALLY ISSUED AUGUST 21, 2009

WARRANT NO. A-27

FORM OF ASSIGNMENT

To be completed and signed only upon transfer of Warrant

     FOR VALUE RECEIVED, the undersigned hereby sells, assigns and transfers unto                                         
the right represented by the within Warrant to purchase
                                         shares of Common
Stock to which the within Warrant relates and appoints                                          attorney to transfer said
right on the books of the Company with full power of substitution in the premises.

	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	Dated:	 	 	 	 	 	 	 	TRANSFEROR:
 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	 	(Print name)
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	By:	 	 	 	 
	 	 	 	 	 	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	Title:	 	 	 	 
	 	 	 	 	 	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	 	TRANSFEREE:
	 
	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	 	(Print name)
	 
	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	 	(Address of Transferee)
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	 	 
	In the presence of:	 	 	 	 	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	 	 	 	 	 	 

14

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