Document:

Exhibit
4.1

 

AMENDMENT
TO THE amended CERTIFICATE OF DESIGNATION

OF
SERIES B CONVERTIBLE PREFERRED STOCK OF

GAUCHO
GROUP HOLDINGS, INC.

 

PURSUANT
TO SECTION 151 OF THE

DELAWARE
GENERAL CORPORATION LAW

 

Gaucho
Group Holdings, Inc., a corporation organized and existing under the General Corporation Law of the State of Delaware (hereinafter
called the “Corporation”), DOES HEREBY CERTIFY:

 

That
pursuant to resolutions adopted by unanimous consent of the Board of Directors of the Corporation, and the resolutions adopted
by a majority of the Series B Convertible Preferred Stockholders, the Certificate of Designation for the Series B Convertible
Preferred Stock, $0.01 par value per share, dated February 21, 2017, as amended (the “Amended Certificate of Designation”),
is hereby further amended as follows:

 

1.
Section 2 of the Amended Certificate of Designation be and it hereby is deleted in its entirety and replaced with the following:

 

“2.
Dividends. Subject to provisions of law, from and after the date of issuance, the holders of record of shares of the Series
B Convertible Preferred Stock shall be entitled to receive dividends, to be paid either in cash or in shares of the Corporation’s
Common Stock in the discretion of the Board of Directors, which shall be payable when, as and if declared by the Board of Directors,
out of assets which are legally available for the payment of such dividends, including any special dividends declared by the Board
of Directors as well as ordinary dividends, at an annual rate of 8% of the Series B Liquidation Value (as defined below) per share
of Series B Convertible Preferred Stock (which amount shall be subject to equitable adjustment whenever there shall occur a stock
dividend, stock split, combination, reorganization, recapitalization, reclassification or other similar event), provided that
such dividends shall not be currently payable and shall only be payable when and if specifically provided herein. Such dividends
shall also be paid upon a liquidation or redemption of the Series B Convertible Preferred Stock in accordance with the provisions
of Section 3 or Section 6. Dividends shall be cumulative, without compounding, and shall accrue daily on each share
of Series B Convertible Preferred Stock from the date of issue thereof. Dividends payable on the Series B Convertible Preferred
Stock for any period less than a full year shall be computed on the basis of the actual number of days elapsed and a 365-day year.
All accrued and accumulated dividends on the Preferred Stock shall be prior and in preference to any dividend on Common Stock
of the Corporation and shall be fully declared and paid before any dividends are declared and paid, or any other distributions
or redemptions are made, on any shares of Common Stock. Upon the conversion of shares of the Series B Preferred Stock into Common
Stock of the Corporation, all cumulative dividends with respect to such converted shares which have not been declared by the Board
of Directors shall be cancelled.”

 

    	 

    	 

    

 

IN
WITNESS WHEREOF, this Amendment to the Certificate of Designation has been executed on behalf of the Corporation by its Chief
Executive Officer, and attested by its Secretary, this 23rd day of October, 2020.

 

	 	GAUCHO
    GROUP HOLDINGS, INC.
	 	 	 
	 	By:	/s/
    Scott Mathis
	 	Name:	Scott
    Mathis
	 	Title:
    	Chief
    Executive Officer

 

	Attest:	 
	 	 
	/s/
    Maria Echevarria	 
	Maria
    Echevarria, Secretary	 

 

    	-2-Exhibit 4.11

 

FORM OF

 

INCENTIVE STOCK OPTION GRANT AGREEMENT

 

SYNTHETIC BIOLOGICS, INC. 2020 STOCK
INCENTIVE PLAN

 

This Stock Option Grant
Agreement (the “Grant Agreement”) is made and entered into effective on the Date of Grant set forth in Exhibit
A (the “Date of Grant”) by and between Synthetic Biologics, Inc., a Nevada corporation (the “Company”),
and the individual named in Exhibit A hereto (the “Optionee”).

 

WHEREAS, the Company
desires to provide the Optionee an incentive to participate in the success and growth of the Company through the opportunity to
earn a proprietary interest in the Company; and

 

WHEREAS, to give effect
to the foregoing intention, the Company desires to grant the Optionee an option pursuant to the Synthetic Biologics, Inc. 2020
Stock Incentive Plan (the “Plan”) to acquire the Company’s common stock, par value $0.001 per share (the “Common
Stock”);

 

NOW, THEREFORE, in
consideration of the mutual covenants hereinafter set forth and for good and valuable consideration, the parties hereto agree as
follows:

 

1.                 
Grant. The Company hereby grants the Optionee a Nonqualified Stock Option (the “Option”) to purchase
up to the number of shares of Common Stock (the “Shares”) set forth in Exhibit A hereto at the exercise
price per Share (the “Exercise Price”) set forth in Exhibit A, and on the vesting schedule set forth
in Exhibit A, subject to the terms and conditions set forth herein and the provisions of the Plan, the terms of which are
incorporated herein by reference. Capitalized terms used but not otherwise defined in this Grant Agreement shall have the meanings
as set forth in the Plan.

 

This Option is intended
to qualify as an Incentive Stock Option (“ISO”) under Section 422 of the Code. However, notwithstanding such
designation, if the Optionee becomes eligible in any given year to exercise ISOs for Shares having a Fair Market Value in excess
of $100,000, those options representing the excess shall be treated as Nonqualified Stock Options. In the previous sentence, “ISOs”
include ISOs granted under any plan of the Company or any parent or any Subsidiary of the Company. For the purpose of deciding
which options apply to Shares that “exceed” the $100,000 limit, ISOs shall be taken into account in the same order
as granted. The Fair Market Value of the Shares shall be determined as of the time the Option with respect to such Shares is granted.
The Optionee hereby acknowledges that there is no assurance that the Option will, in fact, be treated as an Incentive Stock Option
under Section 422 of the Code.

 

     

     

    

 

2.       Exercise
Period Following Termination of Service. This Option shall terminate and be canceled to the extent not exercised within
three (3) months after the Optionee’s Service terminates; provided that if such termination is due to the
Optionee’s total and permanent disability within the meaning of Section 22(e)(3) of the Code, this Option shall
terminate and be canceled one (1) year from the date of termination of the Optionee’s Service; and provided, further,
that if Optionee’s Service terminates (other than for Cause) on or after a Change in Control, then the Option shall
remain exercisable until the Expiration Date. Notwithstanding the foregoing, in the event that the Optionee’s Service
is terminated for Cause, then the Option shall immediately terminate on the date of such termination of Service and shall not
be exercisable for any period following such date. In no event, however, shall this Option be exercised later than the
Expiration Date set forth in Exhibit A and in no event shall this Option be exercised for more Shares than the Shares
which otherwise have become exercisable as of the date of termination.

 

3.       Method
of Exercise. This Option is exercisable by delivery to the Company of an exercise notice (the “Exercise Notice”)
in a form satisfactory to the Committee or by such other form or means as the Committee may permit or require. Any Exercise Notice
shall state or provide the number of Shares with respect to which the Option is being exercised (the “Exercised Shares”),
and include such other representations and agreements as may be required by the Company pursuant to the provisions of the Plan.
The Optionee may elect to make payment of the exercise price in cash or by check or by delivery to the Company of certificates
representing shares of outstanding Common Stock already owned by the Optionee that are owned free and clear of any liens, claims,
encumbrances or security interests together with stock powers duly executed and with signature guaranteed. In addition, the Optionee
may make payment through a “cashless exercise” such that without the payment of any funds, the undersigned may exercise
the Option and receive the net number of Shares equal to (x) the number of Shares as to which the Option is being exercised, multiplied
by (y) a fraction, the numerator of which is the Fair Market Value per share (on such date as is determined by the Committee) less
the Exercise Price per Share, and the denominator of which is such Fair Market Value per Share (the number of net Shares to be
received shall be rounded down to the nearest whole number). In the event payment is made by delivery of such Shares, said Shares
shall be deemed to have a per Share value equal to the Fair Market Value per Share on the date of exercise. Upon exercise of the
Option by the Optionee and prior to the delivery of such Exercised Shares, the Company shall have the right to require the Optionee
to satisfy applicable Federal and state tax income tax withholding requirements and the Optionee’s share of applicable employment
withholding taxes in a method satisfactory to the Company. Notwithstanding the foregoing, the Optionee may not exercise the Option
by tender to the Company of Common Stock to the extent such tender would violate the provisions of any law, regulation or agreement
restricting the redemption of the Company’s Common Stock. Further, no Exercised Shares shall be issued unless such exercise
and issuance complies with the requirements relating to the administration of stock option plans and other applicable equity plans
under U.S. state corporate laws, U.S. federal and state securities laws, the Code, any stock exchange or quotation system on which
the Common Stock is listed or quoted, and the applicable laws of any foreign country or jurisdiction where stock grants or other
applicable equity grants are made under the Plan; assuming such compliance, for income tax purposes the Exercised Shares shall
be considered transferred to the Optionee on the date the Option is exercised with respect to such Shares.

 

    -2-

     

    

 

4.       Covenants
Agreement. This Option shall be subject to forfeiture at the election of the Company in the event that the Optionee breaches
any agreement between the Optionee and the Company with respect to noncompetition, nonsolicitation, assignment of inventions and
contributions and/or nondisclosure obligations of the Optionee.

 

5.       Taxes.

 

(a)       By
executing this Grant Agreement, Optionee acknowledges and agrees that Optionee is solely responsible for the satisfaction of any
applicable taxes that may be imposed on Optionee that arise as a result of the grant, vesting or exercise of the Option, including
without limitation any taxes arising under Section 409A of the Code (regarding deferred compensation) or Section 4999 of the Code
(regarding golden parachute excise taxes), and that neither the Company nor the Committee shall have any obligation whatsoever
to pay such taxes or otherwise indemnify or hold Optionee harmless from any or all of such taxes.

 

(b)       Notwithstanding
paragraph (a) above, if any amounts or benefits provided for in this Grant Agreement, when aggregated with any other payments or
benefits payable or provided to the Optionee (the “Total Payments”) would (i) constitute “parachute payments”
within the meaning of Section 280G of the Code (which will not include any portion of payments classified as payments of reasonable
compensation for purposes of Section 280G of the Code, including without limitation amounts allocated to any restrictive covenants),
and (ii) but for this Section 5(b), would be subject to the excise tax imposed by Section 4999 of the Code (the “Excise Tax”),
then the Total Payments will be either: (a) provided in full, or (b) provided as to such lesser extent as would result in no portion
of such Total Payments being subject to the Excise Tax, whichever of the foregoing amounts, taking into account the applicable
federal, state and local income and employment taxes and the Excise Tax, results in the Optionee’s receipt on an after-tax
basis of the greatest amount of the Total Payments, notwithstanding that all or some portion of the Total Payments may be subject
to the Excise Tax. To the extent any reduction in Total Payments is required by this Section 5(b), such reduction shall occur to
the payments and benefits in the order that results in the greatest economic present value of all payments and benefits actually
made to Optionee. Subject to Section 409A of the Code, such order of reductions shall be determined by the Optionee. Unless the
Company and the Optionee otherwise agree in writing, any determination required under this Section 5(b) shall be made in writing
by an independent public accounting firm mutually acceptable to the Company and the Optionee (the “Accountants”) whose
determination shall be conclusive and binding upon the Optionee and the Company for all purposes. For purposes of making the calculations
required by this Section 5(b), the Accountants may make reasonable assumptions and approximations concerning applicable taxes and
may rely on reasonable, good faith interpretations concerning the application of Sections 280G and 4999 of the Code. The Company
and the Optionee shall furnish to the Accountants such information and documents as the Accountants may reasonably request in order
to make a determination under this Section 5(b). The Company shall pay all fees and expenses of the Accountants.

 

    -3-

     

    

 

6.       Non-Transferability
of Option. This Option may not be transferred in any manner otherwise than by will or by the laws of descent or distribution
and may be exercised during the lifetime of the Optionee only by the Optionee. The terms of the Plan and this Grant Agreement shall
be binding upon the executors, administrators, heirs, successors and assigns of the Optionee.

 

7.       Securities
Matters. All Shares and Exercised Shares shall be subject to the restrictions on sale, encumbrance and other disposition provided
by Federal or state law. The Company shall not be obligated to sell or issue any Shares or Exercised Shares pursuant to this Grant
Agreement unless, on the date of sale and issuance thereof, such Shares are either registered under the Securities Act of 1933,
as amended (the “Securities Act”), and all applicable state securities laws, or are exempt from registration
thereunder. Regardless of whether the offering and sale of Shares under the Plan have been registered under the Securities Act,
or have been registered or qualified under the securities laws of any state, the Company at its discretion may impose restrictions
upon the sale, pledge or other transfer of such Shares (including the placement of appropriate legends on stock certificates or
the imposition of stop-transfer instructions) if, in the judgment of the Company, such restrictions are necessary in order to achieve
compliance with the Securities Act or the securities laws of any state or any other law.

 

8.       Investment
Purpose. The Optionee represents and warrants that unless the Shares are registered under the Securities Act, any and all Shares
acquired by the Optionee under this Grant Agreement will be acquired for investment for the Optionee’s own account and not
with a view to, for resale in connection with, or with an intent of participating directly or indirectly in, any distribution of
such Shares within the meaning of the Securities Act. The Optionee agrees not to sell, transfer or otherwise dispose of such Shares
unless they are either (1) registered under the Securties Act and all applicable state securities laws, or (2) exempt from such
registration in the opinion of Company counsel.

 

9.       Lock-Up
Agreement. The Optionee hereby agrees that in the event that the Optionee exercises this Option during a period in which any
directors or officers of the Company have agreed with one or more underwriters not to sell securities of the Company, then, as
a condition to such exercise, the Optionee shall enter into an agreement, in form and substance satisfactory to the Company, pursuant
to which the Optionee shall agree to restrictions on transferability of the Shares comparable to the restrictions agreed upon by
such directors or officers of the Company.

 

10.       Other
Plans. No amounts of income received by the Optionee pursuant to this Grant Agreement shall be considered compensation for
purposes of any pension or retirement plan, insurance plan or any other employee benefit plan of the Company or its subsidiaries,
unless otherwise expressly provided in such plan.

 

    -4-

     

    

 

11.       No
Guarantee of Continued Service. The Optionee acknowledges and agrees that the right to exercise the Option pursuant to
the exercise schedule hereof is earned only through continuous Service and such other requirements, if any, as are set forth
in Exhibit A (and not through the act of being hired, being granted an option or purchasing shares hereunder). The
Optionee further acknowledges and agrees that (i) this Grant Agreement, the transactions contemplated hereunder and the
exercise schedule set forth herein do not constitute an express or implied promise of continued employment or service for the
exercise period or for any other period, and shall not interfere with the Optionee’s right or the right of the Company
or its Subsidiaries to terminate the employment or service relationship at any time, with or without cause, subject to the
terms of any written employment agreement that the Optionee may have entered into with the Company or any of its
Subsidiaries; and (ii) the Company would not have granted this Option to the Optionee but for these acknowledgements and
agreements.

 

12.       Entire
Agreement; Governing Law. The Plan is incorporated herein by reference. The Plan and this Grant Agreement constitute the entire
agreement of the parties with respect to the subject matter hereof and supersede in their entirety all prior undertakings and agreements
of the Company and the Optionee with respect to the subject matter hereof, and may not be amended to materially impair the rights
of the Optionee without the Optionee’s consent; provided, however, that no action of the Board or the Committee that alters
or affects the tax treatment of the Option shall be considered to materially impair any rights of the Optionee. In the event of
any conflict between this Grant Agreement and the Plan, the Plan shall be controlling, except as otherwise specifically provided
in the Plan. This Grant Agreement shall be construed under the laws of the State of Nevada, without regard to conflict of laws
principles.

 

13.       Opportunity
for Review. Optionee and the Company agree that this Option is granted under and governed by the terms and conditions of the
Plan and this Grant Agreement. The Optionee has reviewed the Plan and this Grant Agreement in their entirety, has had an opportunity
to obtain the advice of counsel prior to executing this Grant Agreement and fully understands all provisions of the Plan and this
Grant Agreement. The Optionee hereby agrees to accept as binding, conclusive and final all decisions or interpretations of the
Committee upon any questions relating to the Plan and this Grant Agreement. The Optionee further agrees to notify the Company upon
any change in the residence address indicated herein.

 

14.Section 409A.This
Option is intended to be excepted from coverage under Section 409A and shall be administered, interpreted and construed accordingly.
The Company may, in its sole discretion and without the Optionee’s consent, modify or amend the terms of this Grant Agreement,
impose conditions on the timing and effectiveness of the exercise of the Option by Optionee, or take any other action it deems
necessary or advisable, to cause the Option to be excepted from Section 409A (or to comply therewith to the extent the Company
determines it is not excepted).

 

15.       Recoupment.
In the event the Company restates its financial statements due to material noncompliance with any financial reporting
requirements under applicable securities laws, any shares issued pursuant to this Agreement for or in respect of the year
that is restated, or the prior three years, may be recovered to the extent the shares issued exceed the number that would
have been issued based on the restatement. In addition and without limitation of the foregoing,
any amounts paid hereunder shall be subject to recoupment in accordance with The Dodd–Frank Wall Street Reform and
Consumer Protection Act and any implementing regulations thereunder, any clawback policy adopted by the Company or as is
otherwise required by applicable law or stock exchange listing conditions. 

 

[Signature Page Follows]

 

    -5-

     

    

 

IN WITNESS WHEREOF, the parties hereto have
executed this Grant Agreement as of the date set forth in Exhibit A.

 

	 	SYNTHETIC BIOLOGICS, INC.
	 	 	 
	 	By:	                    
	 	 	Name:
	 	 	Title:
	 	 
	 	OPTIONEE

 

 

		Name:

 

    -6-

     

    

 

EXHIBIT
A

 

INCENTIVE STOCK OPTION GRANT AGREEMENT

 

SYNTHETIC BIOLOGICS, INC.

  

		(a).	Optionee’s Name:	 	 

 

		(b).	Date of Grant:	 	 

 

		(c).	Number of Shares Subject to the Option:	 	 

 

		(d).	Exercise Price: $______ per Share

 

		(e).	Expiration Date:	 	 

 

		(f).	Vesting Schedule:

 

Notwithstanding anything contained
herein to the contrary, if a “Change in Control” (as defined in the Plan) occurs prior to the cessation of the Optionee’s
 “Service” (as defined in the Plan), then the Option, to the extent not then vested, shall become fully (100%) vested
immediately prior to the date of such Change in Control.

 

_______ (Initials)

 Optionee

 

_______ (Initials)

Company Signatory

 

    -7-

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