Document:

exv10w1

Exhibit 10.1

THE MEDICINES COMPANY

2000 EMPLOYEE STOCK PURCHASE PLAN1

     The following constitute the provisions of the 2000 Employee Stock Purchase Plan of The
Medicines Company.

     1. PURPOSE. The purpose of the Plan is to provide employees of the Company and its Designated
Subsidiaries with an opportunity to purchase Common Stock of the Company through accumulated
payroll deductions. It is the intention of the Company to have the Plan qualify as an “Employee
Stock Purchase Plan” under Section 423 of the Internal Revenue Code of 1986, as amended. The
provisions of the Plan, accordingly, shall be construed so as to extend and limit participation in
a manner consistent with the requirements of that section of the Code.

     2. DEFINITIONS.

          a. “BOARD” shall mean the Board of Directors of the Company.

          b. “CODE” shall mean the Internal Revenue Code of 1986, as amended.

          c. “COMMON STOCK” shall mean the Common Stock of the Company.

          d. “COMPANY” shall mean The Medicines Company and any Designated Subsidiary of the Company.

          e. “COMPENSATION” means the amount of money reportable on an Employee’s Federal Income Tax
Withholding Statement (Form W-2) before any withholdings for health insurance or under a Section
401(k), 125, 129 or similar plan, including without limitation, salary, wages, overtime, shift
differentials, bonuses and incentive compensation, but excluding third party sick or disability
pay, allowances and reimbursements for expenses such as relocation allowances or travel expenses,
whether specifically designated as such or designated as signing bonuses, income or gains
attributable to restricted stock, stock options, stock appreciation rights or other similar equity
based compensation, imputed income for non cash items, such as life insurance premiums, and similar
items, whether or not specifically itemized on the Form W-2.

          f. “DESIGNATED SUBSIDIARY” shall mean any Subsidiary which has been designated by the Board
from time to time in its sole discretion as eligible to participate in the Plan.

          g. “EMPLOYEE” shall mean any individual who is an employee of the Company for tax purposes
whose customary employment with the Company is more than five (5) months in any calendar year. For
purposes of the Plan, the employment relationship shall be treated as continuing intact while the
individual is on sick leave or other bona fide leave of absence approved by the Company. If a sick
leave or other leave of absence exceeds 90 days and the individual’s right to reemployment is not
guaranteed either by statute or by contract, the individual’s employment relationship with the
Company shall be deemed to have terminated on the 91st day of such leave.

          h. “ENROLLMENT DATE” shall mean the first day of each Offering Period.

          i. “EXERCISE DATE” shall mean the last Trading Day of each Offering Period.

 

			
	1	 	The Plan is restated to reflect the amendment to
Section 12(a) approved by the board of directors on April 21, 2009 and by
stockholders at the 2009 annual meeting.

 

 

          j. “FAIR MARKET VALUE” shall mean the value of the Common Stock on any given date of
determination, determined as follows:

               (1) If the Common Stock is listed on any established stock exchange or a national market
system, including without limitation The Nasdaq National Market or The Nasdaq Small Cap Market of
The Nasdaq Stock Market, its Fair Market Value shall be the closing sales price for such stock (or
the closing bid, if no sales were reported) as quoted on such exchange or system on the date of
such determination, as reported in The Wall Street Journal or such other source as the Board deems
reliable; or

               (2) If the Common Stock is regularly quoted on the over-the- counter market, its Fair Market
Value shall be the mean of the closing bid and asked price for such stock as quoted on such market
on the date of such determination, as reported in The Wall Street Journal or such other source as
the Board deems reliable; or

               (3) In the absence of an established market for the Common Stock, the Fair Market Value of the
Common Stock shall be determined in good faith by the Board.

          k. “OFFERING PERIODS” shall mean the periods of approximately six (6) months during which
payroll deductions will be made and held for the purchase of Common Stock at the end of the
Offering Period, commencing on the first Trading Day on or after September 1 and March 1 of each
year and terminating on the last Trading Day in the periods ending six (6) months later; provided,
however, that the first Offering Period under the Plan shall commence with the first Trading Day of
the month first commencing after the date on which the Common Stock is first traded on the Nasdaq
National Market (such date referred to as the “First Offering Commencement Date”); and provided
further that if the number of days between the date the Common Stock is first traded and the First
Offering Commencement Date is less than 15 days, then the first Offering Period shall commence on
the first Trading Day of the following month. The duration and timing of Offering Periods may be
changed pursuant to Section 4 of this Plan.

          l. “PLAN” shall mean this Employee Stock Purchase Plan.

          m. “PURCHASE PRICE” shall mean eighty-five percent (85%) of the Fair Market Value of a share
of Common Stock on the Enrollment Date on an Offering Period or on the Exercise Date for such
Offering Period, whichever is lower.

          n. “RESERVES” shall mean the number of shares of Common Stock covered by each outstanding
option under the Plan which has not yet been exercised and the number of shares of Common Stock
which have been authorized for issuance under the Plan but not yet placed under option.

          o. “SUBSIDIARY” shall mean a corporation, partnership, limited liability company or similar
entity, whether domestic or foreign, of which not less than 50% of the voting interests are held by
the Company or a Subsidiary, whether or not such entity now exists or is hereafter organized or
acquired by the Company or a Subsidiary.

          p. “TRADING DAY” shall mean a day on which the established stock exchange, the national market
system or the over-the-counter market on which the Common Stock is traded is open for trading.

     3. ELIGIBILITY.

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          a. Any Employee who shall be employed by the Company at least seven (7) calendar days prior to
a given Enrollment Date shall be eligible to participate in the Offering Period commencing on such
Enrollment Date.

          b. Any provisions of the Plan to the contrary notwithstanding, no Employee shall be granted an
option under the Plan (i) to the extent that, immediately after the grant, such Employee (or any
other person whose stock would be attributed to such Employee pursuant to Section 424(d) of the
Code) would own capital stock of the Company and/or hold outstanding options to purchase such stock
possessing five percent (5%) or more of the total combined voting power or value of all classes of
the capital stock of the Company or of any Subsidiary, or (ii) to the extent that his or her rights
to purchase stock under all employee stock purchase plans of the Company and its Subsidiaries
accrues at a rate which exceeds Twenty-Five Thousand Dollars ($25,000) worth of stock (determined
at the Fair Market Value of a share of Common Stock at the time such option is granted) for each
calendar year in which such option is outstanding at any time. In the event that an Employee may
not be granted an option under the Plan because of the foregoing restrictions, the Employee shall
be granted an option to purchase the maximum number of shares that would not violate the foregoing
restrictions.

     4. OFFERING PERIODS AND PURCHASE PERIODS. The Board shall have the power to change the
duration of Offering Periods (including the commencement dates thereof) with respect to future
offerings without stockholder approval if such change is announced at least five (5) days prior to
the scheduled beginning of the Offering Period to be affected thereafter.

     5. PARTICIPATION.

          a. An eligible Employee may become a participant in the Plan by completing a subscription
agreement in the form as the Company may deem satisfactory and filing it with the Company’s payroll
office or such other office as the Company may direct prior to the Enrollment Date for the
applicable Offering Period.

          b. Payroll deductions for a participant shall commence on the first payroll following the
Enrollment Date for the applicable Offering Period and shall end on the last payroll in such
Offering Period, unless sooner terminated by the participant as provided in Section 9 hereof.

     6. PAYROLL DEDUCTIONS.

          a. At the time a participant files his or her subscription agreement, he or she shall elect to
have payroll deductions made on each payday during the Offering Period in an amount not exceeding
ten percent (10%) of the Compensation which he or she receives on each payday during the Offering
Period.

          b. All payroll deductions made for a participant shall be credited to his or her account under
the Plan and shall be withheld in whole percentages only. A participant may not make any additional
payments into such account.

          c. A participant may discontinue his or her participation in the Plan as provided in Section 9
hereof, or may increase or decrease the rate of his or her payroll deductions to not more than ten
percent (10%) or less than zero percent (0%) not more than one (1) time during each Offering Period
by completing or filing with the Company a new subscription agreement authorizing such change in
payroll deduction rate. The Board may, in its discretion, increase or decrease the number of
participation rate changes that may be made by a participant during any Offering Period. The change
in rate shall be effective with the first full payroll period following the fifth (5th) business
day after the Company’s

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receipt of the new subscription agreement. A participant’s subscription agreement shall remain
in effect for successive Offering Periods unless terminated as provided in Section 9 hereof.

          d. At the time the option is exercised, in whole or in part, or at the time any of the
Company’s Common Stock issued under the Plan is disposed of, the participant must make adequate
provision for the Company’s federal, state, or other tax withholding obligations, if any, which
arise upon the exercise of the option or the disposition of the Common Stock. At any time, the
Company may, but shall not be obligated to, withhold from the participant’s compensation the amount
necessary for the Company to meet applicable withholding obligations, including any withholding
required to make available to the Company any tax deductions or benefits attributable to sale or
early disposition of Common Stock by the Employee.

     7. GRANT OF OPTION. On the Enrollment Date for each Offering Period, each eligible Employee
participating in such Offering Period shall be granted an option to purchase (at the applicable
Purchase Price) up to a whole number of shares of the Company’s Common Stock (the “Option Shares”)
determined by multiplying $2,083 by the number of full months in the Offering Period and dividing
the result by the Fair Market Value of a share of Common Stock on the Enrollment Date (subject to
any adjustment pursuant to Section 16), and provided that such purchase shall be subject to the
limitations set forth in Sections 3(b) and 12 hereof. Exercise of the option shall occur as
provided in Section 8 hereof, unless the participant has withdrawn pursuant to Section 9 hereof.
The option shall expire on the last day of the Offering Period.

     8. EXERCISE OF OPTION. Unless a participant withdraws from the Plan as provided in Section 9
hereof, his or her option for the purchase of shares shall be exercised automatically on the
Exercise Date applicable to the particular Offering Period, and a number of full shares not
exceeding the number of shares as to which such participant’s option is exercisable on such
Exercise Date shall be purchased for such participant at the applicable Purchase Price with the
accumulated payroll deductions in his or her account. No fractional shares shall be purchased. Any
balance remaining in the participant’s payroll deduction account after such Exercise Date shall be
automatically refunded to the participant, except that any balance that is less than the Purchase
Price of one share of Common Stock will be carried forward into the participant’s payroll deduction
account for the following Offering Period, unless the participant elects not to participate in the
following Offering Period under the Plan, in which case the balance in the participant’s account
shall be refunded. During a participant’s lifetime, a participant’s option to purchase shares
hereunder is exercisable only by him or her.

     9. WITHDRAWAL.

          a. A participant may withdraw all but not less than all the payroll deductions credited to his
or her account and not yet used to exercise his or her option under the Plan at any time by giving
written notice to the Company in the form as the Company may deem satisfactory and filing it with
the Company’s payroll office or such other office as the Company may direct; provided that no
Employee may withdraw his or her payroll deductions less than ten (10) Trading Days prior to an
Exercise Date. All of the participant’s payroll deductions credited to his or her account shall be
paid to such participant promptly after receipt of notice of withdrawal and such participant’s
option for the Offering Period shall be automatically terminated upon receipt of such notice, and
no further payroll deductions from such participant for the purchase of shares shall be made for
such Offering Period. If a participant withdraws from an Offering Period, payroll deductions shall
not resume at the beginning of the succeeding Offering Period unless the participant delivers to
the Company a new subscription agreement.

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          b. A participant’s withdrawal from an Offering Period shall not have any effect upon his or
her eligibility to participate in any similar plan which may hereafter be adopted by the Company or
in succeeding Offering Periods.

     10. TERMINATION OF EMPLOYMENT. Upon a participant’s ceasing to be an Employee, for any reason,
he or she shall be deemed to have elected to withdraw from the Plan, such participant’s option
shall be automatically terminated and the accumulated payroll deductions credited to such
participant’s account during the Offering Period but not yet used to exercise his or her option
shall be returned to such participant or, in the case of his or her death, to the executor or
administrator of the Employee’s estate or if no such executor or administrator has been appointed
to the knowledge of the Company, to such other person(s) as the Company may, in its discretion,
designate. If, prior to the last day of the Offering Period, the Designated Subsidiary by which an
Employee is employed shall cease to be a Subsidiary of the Company, or if the Employee is
transferred to a Subsidiary of the Company that is not a Designated Subsidiary, the Employee shall
be deemed to have terminated employment for the purposes of this Plan.

     11. INTEREST. No interest shall accrue on the payroll deductions of a participant in the
Plan.

     12. STOCK.

          a. Subject to adjustment upon changes in capitalization of the Company as provided in Section
16 hereof, the maximum number of shares of the Company’s Common Stock which shall be made available
for sale under the Plan shall be 805,500 shares. If, on a given Exercise Date, the number of shares
with respect to which options are to be exercised exceeds the number of shares then available under
the Plan, the Company shall make a pro rata allocation of the shares remaining available for
purchase in as uniform a manner as shall be practicable and as it shall determine to be equitable.

          b. The participant shall have no interest or voting right in shares covered by his or her
option until such option has been exercised.

     13. ADMINISTRATION. The Plan shall be administered by the Board or a committee of members of
the Board appointed by the Board. The Board or its committee shall have full and exclusive
discretionary authority to construe, interpret and apply the terms of the Plan, to determine
eligibility and to adjudicate all disputed claims filed under the Plan. Every finding, decision and
determination made by the Board or its committee shall, to the full extent permitted by law, be
final and binding upon all parties.

     14. TRANSFERABILITY. Neither payroll deductions credited to a participant’s account nor any
rights with regard to the exercise of an option or to receive shares under the Plan may be
assigned, transferred, pledged or otherwise disposed of in any way (other than by will or the laws
of descent and distribution by the participant). Any such attempt at assignment, transfer, pledge
or other disposition shall be without effect, except that the Company may treat such act as an
election to withdraw funds from an Offering Period in accordance with Section 9 hereof.

     15. USE OF FUNDS. All payroll deductions received or held by the Company under the Plan may be
used by the Company for any corporate purpose, and the Company shall not be obligated to segregate
such payroll deductions.

     16. ADJUSTMENTS UPON CHANGES IN CAPITALIZATION, DISSOLUTION, LIQUIDATION, MERGER OR ASSET
SALE.

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          a. CHANGES IN CAPITALIZATION. Subject to any required action by the stockholders of the
Company, the maximum number of shares of Common Stock available for sale under the Plan, the
Reserves, the maximum number of shares each participant may purchase during each Offering Period
(pursuant to Section 7), as well as the price per share and the number of shares of Common Stock
covered by each option under the Plan which has not yet been exercised, shall be proportionately
adjusted for any increase or decrease in the number of issued shares of Common Stock resulting from
a stock split, reverse stock split, stock dividend, combination or reclassification of the Common
Stock. Such adjustment shall be made by the Board, whose determination in that respect shall be
final, binding and conclusive. Except as expressly provided herein, no issuance by the Company of
shares of stock of any class, or securities convertible into shares of stock of any class, shall
affect, and no adjustment by reason thereof shall be made with respect to, the number or price of
shares of Common Stock subject to an option.

          b. DISSOLUTION OR LIQUIDATION. In the event of the proposed dissolution or liquidation of the
Company, the Board shall shorten any Offering Period then in progress by setting a new Exercise
Date (the “NEW EXERCISE DATE”), and such Offering Period shall terminate on the New Exercise Date.
The New Exercise Date shall be before the date of the Company’s proposed dissolution or
liquidation. The Board shall notify each participant in writing, at least ten (10) days prior to
the New Exercise Date, that the Exercise Date for the participant’s option has been changed to the
New Exercise Date and that the participant’s option shall be exercised automatically on the New
Exercise Date, unless prior to such date the participant has withdrawn from the Offering Period as
provided in Section 9 hereof.

          c. MERGER OR ASSET SALE. If the Company shall at any time merge or consolidate with another
corporation and the holders of the capital stock of the Company immediately prior to such merger or
consolidation continue to hold at least sixty percent (60%) by voting power of the capital stock of
the surviving corporation (“Continuity of Control”), the holder of each option then outstanding
will thereafter be entitled to receive at the next Exercise Date upon the exercise of such option
for each share as to which such option shall be exercised the securities or property which a holder
of one share of Common Stock was entitled to upon and at the time of such merger or consolidation,
and the Board shall take such steps in connection with such merger or consolidation as the Board
shall deem necessary to assure that the provisions of Section 16(a) shall thereafter be applicable,
as nearly as reasonably may be, in relation to the said securities or property as to which such
holder of such option might thereafter be entitled to receive thereunder.

     In the event of a merger or consolidation of the Company with or into another corporation
which does not involve Continuity of Control, or which involves a sale of all or substantially all
of the assets of the Company (an “Acquisition”), while unexercised options remain outstanding under
the Plan, all options outstanding as of the effective date of the Acquisition shall be deemed
assumed or substituted for and each holder of an outstanding option shall be entitled, upon
exercise of such option, to receive in lieu of shares of Common Stock, shares of such stock or
other securities as the holders of shares of Common Stock received pursuant to the terms of the
Acquisition. Notwithstanding the foregoing, in the event that the acquiring or succeeding
corporation (or an affiliate thereof) does not agree to assume or substitute for the options, then
the Board shall shorten any Offering Period then in progress by setting a New Exercise Date, and
such Offering Period then in progress shall terminate on the New Exercise Date. The New Exercise
Date shall be before the effective date of the Acquisition. The Board shall notify each participant
in writing, at least ten (10) days prior to the New Exercise Date, that the Exercise Date for the
participant’s option has been changed to the New Exercise Date and that the participant’s option
shall be exercised automatically on the New Exercise Date, unless prior to such date the
participant has withdrawn from the Offering Period as provided in Section 9 hereof.

     17. AMENDMENT OR TERMINATION.

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          a. The Board of Directors of the Company may at any time and for any reason terminate or amend
the Plan. Except as provided in Section 16 hereof, no such termination can affect options
previously granted, provided that an Offering Period may be terminated by the Board of Directors if
the Board determines that the termination of the Plan is in the best interests of the Company and
its stockholders, and upon termination of the Plan all amounts in the accounts of participating
employees shall be promptly refunded. Except as provided in Section 16 hereof, no amendment may
make any change in any option theretofore granted which adversely affects the rights of any
participant without the consent of the participant. To the extent necessary to comply with Section
423 of the Code (or any successor rule or provision or any other applicable law, regulation or
stock exchange rule), if applicable, the Company shall obtain stockholder approval in such a manner
and to such a degree as required.

          b. Without stockholder consent and without regard to whether any participant rights may be
considered to have been “adversely affected,” the Board (or its committee) shall be entitled to
change the Offering Periods, limit the frequency and/or number of changes in the amount withheld
during an Offering Period, establish the exchange ratio applicable to amounts withheld in a
currency other than U.S. dollars, permit payroll withholding in excess of the amount designated by
a participant in order to adjust for delays or mistakes in the Company’s processing of properly
completed withholding elections, establish reasonable waiting and adjustment periods and/or
accounting and crediting procedures to ensure that amounts applied toward the purchase of Common
Stock for each participant properly correspond with amounts withheld from the participant’s
Compensation, and establish such other limitations or procedures as the Board (or its committee)
determines in its sole discretion advisable which are consistent with the Plan.

     18. NOTICES. All notices or other communications by a participant to the Company under or in
connection with the Plan shall be deemed to have been duly given when received in the form
specified by the Company at the location, or by the person, designated by the Company for the
receipt thereof.

     19. CONDITIONS UPON ISSUANCE OF SHARES. Shares shall not be issued with respect to an option
unless the exercise of such option and the issuance and delivery of such shares pursuant thereto
shall comply with all applicable provisions of law, domestic or foreign, including, without
limitation, the Securities Act of 1933, as amended, the Securities Exchange Act of 1934, as
amended, the rules and regulations promulgated thereunder, and the requirements of any stock
exchange upon which the shares may then be listed, and shall be further subject to the approval of
counsel for the Company with respect to such compliance.

          As a condition to the exercise of an option, the Company may require the person exercising
such option to represent and warrant at the time of any such exercise that the shares are being
purchased only for investment and without any present intention to sell or distribute such shares
if, in the opinion of counsel for the Company, such a representation is required by any of the
aforementioned applicable provisions of law.

     20. GOVERNMENTAL REGULATIONS. The Company’s obligation to sell and deliver Common Stock under
this Plan is subject to listing on an established stock exchange or quotation on a national market
system or an over-the-counter market (to the extent the Common Stock is then so listed or quoted)
and the approval of all governmental authorities required in connection with the authorization,
issuance or sale of such stock.

     21. GOVERNING LAW. The Plan shall be governed by Massachusetts law except to the extent that
such law is preempted by federal law.

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     22. SOURCE OF SHARES. Shares may be issued upon exercise of an option from authorized but
unissued Common Stock, from shares held in the treasury of the Company, or from any other proper
source.

     23. NOTIFICATION UPON SALE OF SHARES. Each Employee agrees, by entering the Plan, to promptly
give the Company notice of any disposition of shares purchased under the Plan where such
disposition occurs within two years after the date of grant of the option pursuant to which such
shares were purchased.

     24. EFFECTIVE DATE. The Plan shall take effect upon the date of the Company’s initial public
offering of its equity securities registered on Form S-1 with the Securities and Exchange
Commission, subject to approval by the stockholders of the Company. It shall continue in effect for
a term of ten (10) years unless sooner terminated under Section 17 hereof.

 -8-exv4w1

Exhibit 4.1

 

 

 

VECTOR GROUP LTD.

AND EACH OF THE GUARANTORS PARTY HERETO

11% SENIOR SECURED NOTES DUE 2015

 

SECOND SUPPLEMENTAL INDENTURE

Dated as of September 1, 2009

To

INDENTURE

Dated as of August 16, 2007

As supplemented by First Supplemental Indenture dated as of July 15, 2008

 

 

U.S. BANK NATIONAL ASSOCIATION

as Trustee and as Collateral Agent

 

 

 

 

 

SECOND SUPPLEMENTAL INDENTURE

     SECOND SUPPLEMENTAL INDENTURE (this “Second Supplemental Indenture”), dated as of September 1,
2009, among Vector Group Ltd., a Delaware corporation (the “Company”), the Guarantors listed on the
signature pages hereto (the “Guarantors”) and U.S. Bank, National Association, as Trustee (the
“Trustee”) and as Collateral Agent (the “Agent”).

W I T N E S S E T H

     WHEREAS, the Company and the Guarantors have heretofore executed and delivered an Indenture,
dated as of August 16, 2007 (the “Base Indenture”), as supplemented by a First Supplemental
Indenture dated as of July 15, 2008 (the “First Supplemental Indenture” and, together with the Base
Indenture, the “Indenture”) providing for the initial issuance by the Company of its Initial Notes
(as defined below);

     WHEREAS, Section 9.01 of the Base Indenture provides that the Company, the Guarantors and the
Trustee may amend or supplement the Indenture from time to time without the consent of the Holder
(as defined in the Base Indenture) to provide for the issuance of Additional Notes (as defined in
the Base Indenture) in accordance with the limitations set forth in the Base Indenture;

     WHEREAS, all things necessary to make the New Notes (as defined below), when executed by the
Company and authenticated and delivered by the Trustee and issued upon the terms and subject to the
conditions set forth herein and in the Indenture against payment therefor, the valid, binding and
legal obligations of the Company and to make this Second Supplemental Indenture a valid, binding
and legal agreement of the Company and the Guarantors, have been done;

     NOW THEREFORE, in consideration of the foregoing and for other good and valuable
consideration, the receipt of which is hereby acknowledged, the Company and each Guarantor, the
Trustee and the Agent mutually covenant and agree for the equal and ratable benefit of the holders
of the Additional Notes as follows:

SECTION I

DEFINITIONS

     All Capitalized terms used herein without definition shall have the meanings assigned to them
in the Indenture. The rules of interpretation set forth in the Indenture shall be applied here as
if set forth in full herein.

     “Initial Notes” means the $165 million aggregate principal amount of Notes issued under the
Indenture on August 16, 2007.

     “New Notes” means up to $85 million aggregate principal amount of Additional Notes (other than
the Initial Notes) issued under this Second Supplemental Indenture, as part of the same series as
the Initial Notes.

     “Notes” means the Company’s 11% Senior Secured Notes due 2015. The Initial Notes and the New
Notes will be part of the same series for all purposes under the Indenture and this Second
Supplemental Indenture, and unless the context otherwise requires, all references to the Notes will
include the Initial Notes and the New Notes.

2

 

SECTION II

AUTHORIZATION AND ISSUANCE OF ADDITIONAL NOTES

     A. The Company will be entitled, upon delivery of an Officers’ Certificate and an Opinion of
Counsel, subject to its compliance with Section 4.09 of the Indenture, to issue the New Notes under
this Second Supplemental Indenture which will have identical terms as the Initial Notes, other than
with respect to the date of issuance and issue price. The Initial Notes and the Additional Notes
issued will be treated as a single class for all purposes under the Indenture and this Second
Supplemental Indenture including, but not limited to, Section 2.06.

     B. With respect to the New Notes, the Company will set forth in one or more resolutions of its
Board of Directors and/or a designated committee thereof and an Officers’ Certificate, a copy of
each which will be delivered to the Trustee, the following information:

     1. the aggregate principal amount of such New Notes to be authenticated and
delivered pursuant to this Second Supplemental Indenture; and

     2. the issue price, the issue date and the CUSIP numbers of such New Notes.

SECTION III

EXECUTION AND AUTHENTICATION OF NEW NOTES

     The Trustee will, upon receipt of a written order of the Company signed by an Officer,
authenticate New Notes for issue that may be validly issued under this Second Supplemental
Indenture. The aggregate principal amount of Notes outstanding at any time may not exceed the
aggregate principal amount of Notes authorized for issuance by the Company pursuant to one or more
Authentication Orders, except as provided in Section 2.07 of the Base Indenture.

SECTION IV

COLLATERAL AND SECURITY

     When issued in accordance with the Indenture and this Second Supplemental Indenture, the New
Notes shall constitute Parity Lien Obligations. In accordance with Section 10.02 of the Indenture,
all Parity Liens granted at any time by the Pledgors or VGR Holding shall secure, equally and
ratably, all present and future Parity Lien Obligations and all proceeds of all Parity Liens
granted at any time by the Pledgors or VGR Holding shall be allocated and distributed equally and
ratably on account of the Parity Lien Debt and other Parity Lien Obligations.

SECTION V

REAFFIRMATION OF COLLATERAL DOCUMENTS

AND GRANT OF SECURITY INTEREST

     For value received, each of the Pledgors and VGR Holding hereby confirms, reaffirms and
restates that it is bound by each of the Collateral Documents to which it is a party, and that each
of the Collateral Documents to which such Pledgor and VGR Holding is a party and all of the
Collateral described therein do and shall continue to secure payment of all amounts due under the
Note Guarantees of the Pledgors and VGR Holding, respectively, and the performance of all
Obligations of each of the
Pledgors and VGR Holdings, respectively, to the Holders. Each of the Pledgors and VGR Holding
that is a party to the Collateral Documents hereby reaffirms its grant of a security interest in
the Collateral to the Collateral Agent securing its Note Guarantee subject in the case of the
Liggett Guarantors to the terms of the Intercreditor Agreement and agrees that each of the
Collateral Documents to which it is a party shall continue to be in full force and effect and are
hereby in all respects ratified and confirmed.

3

 

SECTION VI

REAFFIRMATION OF GUARANTEES

     For value received, each Guarantor hereby confirms, reaffirms and restates that it, jointly
and severally, unconditionally guarantees, to the extent set forth in the Indenture, (a) the due
and punctual payment of the principal of, premium and Liquidated Damages, if any, and interest on,
the Notes, whether at maturity, by acceleration, redemption or otherwise, the due and punctual
payment of interest on overdue principal of and interest on the Notes, if any, if lawful, and the
due and punctual performance of all other obligations of the Company to the Holders or the Trustee
all in accordance with the terms of the Indenture and (b) in case of any extension of time of
payment or renewal of any Notes or any of such other obligations, that the same will be promptly
paid in full when due or performed in accordance with the terms of the extension or renewal,
whether at stated maturity, by acceleration or otherwise. The obligations of the Guarantors to the
Holders of Notes and to the Trustee pursuant to the Note Guarantee and the Indenture are expressly
set forth in Article 11 of the Base Indenture and reference is hereby made to the Base Indenture
for the precise terms of the Note Guarantee.

SECTION VII

MISCELLANEOUS PROVISIONS

     A. The Trustee makes no undertaking or representation in respect of, and shall not be
responsible in any manner whatsoever for and in respect of, the validity or sufficiency of this
Second Supplemental Indenture or the proper authorization or the due execution hereof by the
Company or for or in respect of the recitals and statements contained herein, all of which recitals
and statements are made solely by the Company.

     B. On the date hereof, the Indenture shall be supplemented and amended in accordance herewith,
and this Second Supplemental Indenture shall form part of the Indenture for all purposes, and the
holder of every Note heretofore or hereafter authenticated and delivered under the Indenture shall
be bound thereby. The Trustee accepts the trusts created by the Indenture, as amended and
supplemented by this Second Supplemental Indenture, and agrees to perform the same upon the terms
and conditions of the Indenture, as amended and supplemented by this Second Supplemental Indenture.

     C. This Second Supplemental Indenture shall be deemed to be incorporated in, and made a part
of, the Indenture. The Indenture, as amended and supplemented by this Second Supplemental
Indenture, shall be read, taken and construed as one and the same instrument and the all the
provisions of the Indenture shall remain in full force and effect in accordance with the terms
thereof and as amended and supplemented by this Second Supplemental Indenture.

     D. THIS SECOND SUPPLEMENTAL INDENTURE SHALL BE GOVERNED BY, AND CONSTRUED IN ACCORDANCE WITH,
THE LAWS OF THE STATE OF NEW YORK, WITHOUT REGARD TO ANY PRINCIPLES OF CONFLICTS OF LAWS THAT WOULD
RESULT IN THE APPLICATION OF THE LAWS OF ANY OTHER JURISDICTION.

     E. This Second Supplemental Indenture may be executed in any number of counterparts, each of
which so executed shall be deemed to be an original, but all such counterparts shall together
constitute but one and the same instrument.

4

 

SIGNATURES

Dated as of September 1, 2009

	 	 	 	 	 
	 	THE COMPANY:

VECTOR GROUP LTD.

 	 
	 	By:  	/s/ Richard J. Lampen
 	 
	 	 	Name:  	Richard J. Lampen 	 
	 	 	Title:  	Executive Vice President 	 
	 

	 	 	 	 	 
	 	GUARANTORS:

VGR HOLDING LLC

 	 
	 	By:  	/s/ Marc N. Bell
 	 
	 	 	Name:  	Marc N. Bell 	 
	 	 	Title:  	Manager 	 
	 

	 	 	 	 	 
	 	LIGGETT GROUP LLC

 	 
	 	By:  	/s/ Ronald J. Bernstein
 	 
	 	 	Name:  	Ronald J. Bernstein 	 
	 	 	Title:  	Manager/President and Chief
Executive Officer 	 
	 

	 	 	 	 	 
	 	LIGGETT VECTOR BRANDS INC.

 	 
	 	By:  	/s/ Ronald J. Bernstein
 	 
	 	 	Name:  	Ronald J. Bernstein 	 
	 	 	Title:  	President and Chief Executive Officer 	 

5

 

	 	 	 	 	 

	 	 	 	 	 
	 	VECTOR RESEARCH LLC

 	 
	 	By:  	/s/ Francis G. Wall
 	 
	 	 	Name:  	Francis G. Wall 	 
	 	 	Title:  	Vice President and Chief Financial Officer 	 
	 

	 	 	 	 	 
	 	VECTOR TOBACCO INC.

 	 
	 	By:  	/s/ Francis G. Wall
 	 
	 	 	Name:  	Francis G. Wall 	 
	 	 	Title:  	Vice President - Finance 	 
	 

	 	 	 	 	 
	 	LIGGETT & MYERS HOLDINGS INC.

 	 
	 	By:  	/s/ Marc N. Bell
 	 
	 	 	Name:  	Marc N. Bell 	 
	 	 	Title:  	Vice President 	 
	 

	 	 	 	 	 
	 	LIGGETT & MYERS INC.

 	 
	 	By:  	/s/ Ronald J. Bernstein
 	 
	 	 	Name:  	Ronald J. Bernstein 	 
	 	 	Title:  	President 	 
	 

	 	 	 	 	 
	 	100 MAPLE LLC

 	 
	 	By:  	/s/ Ronald J. Bernstein
 	 
	 	 	Name:  	Ronald J. Bernstein 	 
	 	 	Title:  	Manager 	 

6

 

	 	 	 	 	 

	 	 	 	 	 
	 	V.T. AVIATION LLC

 	 
	 	By:  	/s/ Francis G. Wall
 	 
	 	 	Name:  	Francis G. Wall 	 
	 	 	Title:  	Vice President - Finance 	 
	 

	 	 	 	 	 
	 	VGR AVIATION LLC

 	 
	 	By:  	/s/ Francis G. Wall
 	 
	 	 	Name:  	Francis G. Wall 	 
	 	 	Title:  	Vice President - Finance 	 
	 

	 	 	 	 	 
	 	EVE HOLDINGS INC.

 	 
	 	By:  	/s/ Marc N. Bell
 	 
	 	 	Name:  	Marc N. Bell 	 
	 	 	Title:  	Vice President 	 

7

 

	 	 	 	 	 

	 	 	 	 	 
	TRUSTEE:

U.S. BANK NATIONAL ASSOCIATION

 	 
	By:  	/s/ Richard Prokosch
 	 
	 	Name:  	Richard Prokosch 	 
	 	Title:  	Vice President 	 
	 

8

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