Document:

EX-10.16.4

EXHIBIT 10.16.4

THIRD AMENDMENT TO

SECOND AMENDED AND RESTATED LOAN AGREEMENT

     THIS THIRD AMENDMENT TO SECOND AMENDED AND RESTATED LOAN AGREEMENT (this “Amendment”),
dated April 6, 2008, is made and entered into on the terms and conditions hereinafter set forth, by
and between CUMBERLAND PHARMACEUTICALS, INC., a Tennessee corporation (the “Borrower”), and
BANK OF AMERICA, N.A., a national banking association (the “Bank”).

RECITALS:

     1. The Borrower and the Bank are parties to a Second Amended and Restated Agreement dated as
of April 6, 2006, as amended by that certain First Amendment to Second Amended and Restated Loan
Agreement dated as of December 31, 2006, as further amended by that certain Second Amendment to
Second Amended and Restated Loan Agreement dated as of July 18, 2007 (as the same heretofore has
been or hereafter may be further amended, restated, supplemented, extended, renewed, replaced or
otherwise modified from time to time, the “Loan Agreement”), pursuant to which the Bank has
agreed to extend credit to the Borrower subject to and upon the terms and conditions set forth in
the Loan Agreement.

     2. The parties hereto desire to amend the Loan Agreement in certain respects as more
particularly hereinafter set forth.

     3. Capitalized terms used but not otherwise defined in this Amendment shall have the same
meanings as in the Loan Agreement.

AGREEMENTS:

     NOW, THEREFORE, in consideration of the mutual covenants and agreements hereinafter set forth,
and for other good and valuable consideration, the receipt and sufficiency of all of which are
hereby acknowledged, the parties hereto agree as follows:

     1. Amendment of Section 1.2. Section 1.2 (Availability Period) of the Loan Agreement
is hereby amended by deleting the last sentence of Section 1.2 and substituting the following in
lieu thereof:

Thereafter, the maximum availability under the Facility No. 1 Commitment shall be
$4,000,000 until the third (3rd) anniversary of the date of this Agreement, or such
earlier date as the availability may terminate as provided in this Agreement (the
“Facility No. 1 Expiration Date”).

     2. Representations and Warranties of the Borrower. As an inducement to the Bank to
enter into this Amendment, the Borrower hereby represents and warrants that on and as of the date
hereof, and taking into account the provisions hereof, the representations and warranties contained
in the Loan Agreement and the other Loan Documents are true and correct in all material respects,
except for representations and warranties that expressly relate to an earlier date, which remain
true and correct as of said earlier date.

     3. Effect of Amendment; Continuing Effectiveness of Loan Agreement and Loan Documents.

     (a) Neither this Amendment nor any other indulgences that may have been granted to the
Borrower by the Bank shall constitute a course of dealing or otherwise obligate the Bank to
modify, expand or extend the agreements contained herein, to agree to any other amendments
to

 

 

the Loan Agreement or to grant any consent to, waiver of or indulgence with respect to any
other noncompliance with any provision of the Loan Documents.

     (b) Upon and after the effectiveness of this Amendment, each reference in the Loan
Agreement to “this Agreement”, “hereunder”, “hereof” or words of like import referring to
the Loan Agreement, and each reference in the other Loan Documents to “the Loan Agreement”,
“thereunder”, “thereof” or words of like import referring to the Loan Agreement, shall mean
and be a reference to the Loan Agreement as modified hereby. This Amendment shall
constitute a Loan Document for all purposes of the Loan Agreement and the other Loan
Documents.

     (c) Except to the extent amended or modified hereby, the Loan Agreement, the other Loan
Documents and all terms, conditions and provisions thereof shall continue in full force and
effect in all respects and shall be construed in accordance with the modification of the
Loan Agreement effected hereby.

     4. Release and Waiver. The Borrower hereby stipulates, acknowledges and agrees that
it has no claims or causes of action of any kind whatsoever against the Bank arising out of or
relating in any way to any event, circumstance, action or failure to act with respect to this
Amendment, the Loan Agreement, the other Loan Documents or any matters described or referred to
herein or therein or otherwise related hereto or thereto. The Borrower hereby releases the Bank
from any and all claims, causes of action, demands and liabilities of any kind whatsoever, whether
direct or indirect, fixed or contingent, liquidated or unliquidated, disputed or undisputed, known
or unknown, that the Borrower may now or hereafter have and that arise out of or relate in any way
to any event, circumstance, action or failure to act on or before the date of this Amendment with
respect to this Amendment, the Loan Agreement, the other Loan Documents or any matters described or
referred to herein or therein or otherwise related hereto or thereto. The release by the Borrower
herein, together with the other terms and provisions of this Amendment, are entered into by the
Borrower advisedly and without compulsion, coercion or duress, the Borrower having determined that
this Amendment is in the economic best interests of the Borrower. The Borrower represents that it
is entering into this Amendment freely and with the advice of counsel as to its legal alternatives.

     5. Further Actions. Each of the parties to this Amendment agrees that at any time and
from time to time upon written request of the other party, it will execute and deliver such further
documents and do such further acts and things as such other party reasonably may request in order
to effect the intents and purposes of this Amendment.

     6. Counterparts. This Amendment may be executed in multiple counterparts or copies,
each of which shall be deemed an original hereof for all purposes. One or more counterparts or
copies of this Amendment may be executed by one or more of the parties hereto, and some different
counterparts or copies executed by one or more of the other parties. Each counterpart or copy
hereof executed by any party hereto shall be binding upon the party executing same even though
other parties may execute one or more different counterparts or copies, and all counterparts or
copies hereof so executed shall constitute but one and the same agreement. Each party hereto, by
execution of one or more counterparts or copies hereof, expressly authorizes and directs any other
party hereto to detach the signature pages and any corresponding acknowledgment, attestation,
witness or similar pages relating thereto from any such counterpart or copy hereof executed by the
authorizing party and affix same to one or more other identical counterparts or copies hereof so
that upon execution of multiple counterparts or copies hereof by all parties hereto, there shall be
one or more counterparts or copies hereof to which is(are) attached signature pages containing
signatures of all parties hereto and any corresponding acknowledgment, attestation, witness or
similar pages relating thereto.

     7. Miscellaneous.

     (a) This Amendment shall be governed by, construed and enforced in accordance with the
laws of the State of Tennessee, without reference to the conflicts or choice of law
principles thereof.

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     (b) The headings in this Amendment and the usage herein of defined terms are for
convenience of reference only, and shall not be construed as amplifying, limiting or
otherwise affecting the substantive provisions hereof.

     (c) All references herein to the preamble, the recitals or sections, paragraphs,
subparagraphs, annexes or exhibits are to the preamble, recitals, sections, paragraphs,
subparagraphs, annexes and exhibits of or to this Amendment unless otherwise specified. The
words “hereof”, “herein” and “hereunder” and words of similar import, when used in this
Amendment, refer to this Amendment as a whole and not to any particular provision of this
Amendment.

     (d) Any reference herein to any instrument, document or agreement, by whatever
terminology used, shall be deemed to include any and all amendments, modifications,
supplements, extensions, renewals, substitutions and/or replacements thereof as the context
may require.

     (e) When used herein, (1) the singular shall include the plural, and vice versa, and
the use of the masculine, feminine or neuter gender shall include all other genders, as
appropriate, (2) “include”, “includes” and “including” shall be deemed to be followed by
“without limitation” regardless of whether such words or words of like import in fact follow
same, and (3) unless the context clearly indicates otherwise, the disjunctive “or” shall
include the conjunctive “and”.

[Remainder of Page Intentionally Left Blank;

Signature Pages Follow]

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     IN WITNESS WHEREOF, the parties hereto have caused this Amendment to be duly executed and
delivered as of the date first written above.

	 	 	 	 	 
	 	BORROWER:

CUMBERLAND PHARMACEUTICALS, INC.

 	 
	 	By:  	/s/ A.J. Kazimi
 	 
	 	 	Name:  	A.J. Kazimi 	 
	 	 	Title:  	Chief Executive Officer 	 
	 

ACKNOWLEDGED:

CUMBERLAND EMERGING TECHNOLOGIES, INC.

	 	 	 	 	 
	 	 	 
	By:  	/s/ A.J. Kazimi
 	 	 
	 	Name:  	A.J. Kazimi 	 	 
	 	Title:  	Chief Executive Officer 	 	 

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[Signature Page to Third Amendment to Second Amended and Restated Loan Agreement

(Cumberland Pharmaceuticals, Inc.) dated April 6, 2008]

	 	 	 	 	 
	 	BANK:

BANK OF AMERICA, N.A.

 	 
	 	By:  	/s/ Suzanne B. Smith
 	 
	 	 	Name:  	Suzanne B. Smith 	 
	 	 	Title:  	Senior Vice President 	 
	 

-5-EX-10.21.1

EXHIBIT 10.21.1

FIRST AMENDMENT TO OFFICE LEASE AGREEMENT

     THIS FIRST AMENDMENT TO OFFICE LEASE AGREEMENT (this “Amendment”) is entered into between 2525
WEST END, LLC, a Delaware limited liability company (“Landlord”), and CUMBERLAND PHARMACEUTICALS
INC., a Tennessee corporation (“Tenant”), with reference to the following:

     A. Nashville Hines Development, LLC (predecessor-in-interest to Landlord) and Tenant entered
into that certain Office Lease Agreement dated September 10, 2005 (the “Lease”) currently covering
approximately 6,341 RSF on the ninth (9th) floor (the “Original Premises”) of 2525 West End Avenue,
Nashville, Tennessee (the “Building”).

     B. Landlord and Tenant now desire to amend the Lease as set forth below. Unless otherwise
expressly provided in this Amendment, capitalized terms used in this Amendment shall have the same
meanings as in the Lease.

     FOR GOOD AND VALUABLE CONSIDERATION, the receipt and sufficiency of which are acknowledged,
the parties agree as follows:

1. First Expansion Space. Landlord leases to Tenant and Tenant leases from Landlord approximately
2,950 additional RSF (the “First Expansion Space”) known as Suite 930 and located on the ninth
(9th) floor of the Building as shown on the attached Exhibit “A”, which is incorporated
into this Amendment for all purposes. The term “Premises” as used in the Lease means and includes
approximately 9,291 RSF, being the sum of the RSF of the Original Premises (6,341 RSF) and the
First Expansion Space. The lease of the First Expansion Space is subject to all of the terms and
conditions of the Lease currently in effect, except as modified in this Amendment. Tenant
acknowledges that it has no further expansion or preferential rights or options under the Lease.

2. First Extension Period. The Term of the Lease as it pertains to the First Expansion Space only
is extended for a period of five (5) years (the “First Extension Period”) commencing on the First
Expansion Space Commencement Date (defined below), and expiring on December 31, 2015, for a total
term of approximately ninety-one (91) months. The expiration of the Term of the Lease at is
pertains to the Original Premises shall remain December 31, 2010 and after such expiration, all
rights under the Lease pertaining to the Original Premises including, but not limited to, those
Parking Permits set forth in Section 3.4(a) of the Lease, shall terminate. Tenant acknowledges that
it has no further extension or renewal rights or options under the Lease.

3. Base Rental. Exhibit G to the Lease is deleted and replaced by the rent schedule attached
hereto as Exhibit “B”.

4. Additional Rent.

     (a) Commencing on the First Expansion Space Commencement Date and continuing through the expiration
of the original Term (i.e., December 31, 2010), Tenant’s Additional Rental payable under Section
2.3 of the Lease shall be increased to take the First Expansion Space into account and the Expense
Stop, with respect to the First Expansion Space only, refers to Landlord absorbing and being
responsible for paying Operating Expenses (as defined in the

 

 

Lease) during any calendar year to the extent such Operating Expenses are less than Nine and 42/100
Dollars ($9.42) per square foot of space in the Building leased to rent paying tenants as such term
is used in Section 2.3(c) of the Lease.

     (b) Commencing on January 1, 2011 and continuing through the expiration of the First Extension
Period, Tenant’s Additional Rental payable under Section 2.3 of the Lease shall be decreased so as
to omit the Original Premises.

5. Condition of the First Expansion Space.

     (a) Tenant accepts the First Expansion Space in its “as-is” condition. Tenant acknowledges
that Landlord has not undertaken to perform any modification, alteration or improvement to the
First Expansion Space. By taking possession of the First Expansion Space, Tenant waives
(i) any
claims due to defects in the First Expansion Space;
and (ii) all
express and implied warranties of suitability, habitability and fitness for any particular
purpose. Tenant waives the right to terminate the Lease due to the condition of the First
Expansion Space.

     (b) The term “First Expansion Space Commencement Date” means the earlier of (i) June 1, 2008,
and (ii) the date Tenant occupies the First Expansion Space. Landlord shall not be liable or
responsible for any claims, damages or liabilities incurred (or alleged) by Tenant due to any delay
in delivery of the First Expansion Space, nor shall such failure invalidate the Lease or extend the
First Extension Period. Upon determination, Landlord and Tenant, at the request of either, shall
execute an amendment to the Lease confirming the First Expansion Space Commencement Date, together
with corresponding adjustments to the schedule of Base Rental.

6. Parking. In connection with the First Expansion Space, Landlord hereby agrees to make
available, or to cause the Garage Operator to make available, to Tenant (so long as Tenant shall
continue to lease the First Expansion Space) up to twelve (12) permits (“First Expansion Space
Permits”) to park in the Kensington Parking Facility upon the terms and conditions set forth in
Section 3.4 of the Lease. Tenant shall pay as rental for the First Expansion Space Permits at the
rate charged from time to time by Landlord (or the Garage Operator), in its sole and absolute
discretion, plus any applicable taxes thereon. The current charge to Tenant for each First
Expansion Space Permit is $40.00 per month, plus any applicable taxes thereon.

7. Improvement Allowance. Tenant shall receive an improvement allowance in connection with the
First Expansion Space of $[***] per RSF in the First Expansion Space (the “First Expansion Space
Improvement Allowance”) to be paid by Landlord within thirty (30) days of the First Expansion Space
Commencement Date provided that Tenant is not then in default under the Lease. The First Expansion
Space Improvement Allowance may be used for any costs relating to the First Expansion Space.
However, Tenant shall not install any improvements which are not compatible with Landlord’s plans
and specifications for the Building or which have not received prior written approval by Landlord
or Landlord’s architect. Tenant agrees to comply with the terms of Section 5.1 of the Lease with
respect to any Tenant work that is performed in the First Expansion Space.

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8. Consent. This Amendment is subject to, and conditioned upon, any required consent or approval
being unconditionally granted by Landlord’s mortgagee(s). If any such consent shall be denied, or
granted subject to an unacceptable condition, this Amendment shall be null and void and the Lease
shall remain unchanged and in full force and effect.

9. No Broker. Tenant represents and warrants that it has not been represented by any broker or
agent in connection with the execution of this Amendment. Tenant shall indemnify and hold harmless
Landlord and its designated property management, construction and marketing firms, and their
respective partners, members, affiliates and subsidiaries, and all of their respective officers,
directors, shareholders, employees, servants, partners, members, representatives, insurers and
agents from and against all claims (including costs of defense and investigation) of any broker or
agent or similar party claiming by, through or under Tenant in connection with this Amendment.

10. Time of the Essence. Time is of the essence with respect to Tenant’s execution and delivery to
Landlord of this Amendment. If Tenant fails to execute and deliver a signed copy of this Amendment
to Landlord by 5:00 p.m. (in the city in which the Premises is located) on May 1, 2008, this
Amendment shall be deemed null and void and shall have no force or effect, unless otherwise agreed
in writing by Landlord. Landlord’s acceptance, execution and return of this Amendment shall
constitute Landlord’s agreement to waive Tenant’s failure to meet such deadline.

11. Miscellaneous. This Amendment shall become effective only upon full execution and delivery of
this Amendment by Landlord and Tenant. This Amendment contains the parties’ entire agreement
regarding the subject matter covered by this Amendment, and supersedes all prior correspondence,
negotiations, and agreements, if any, whether oral or written, between the parties concerning such
subject matter. There are no contemporaneous oral agreements, and there are no representations or
warranties between the parties not contained in this Amendment. Except as modified by this
Amendment, the terms and provisions of the Lease shall remain in full force and effect, and the
Lease, as modified by this Amendment, shall be binding upon and shall inure to the benefit of the
parties hereto, their successors and permitted assigns.

[Signatures to follow]

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     LANDLORD AND TENANT enter into this Amendment as of the Effective Date (below).

	 	 	 
	LANDLORD:

	 	2525 WEST END, LLC, a Delaware limited liability company

	 	 	 	 	 
	 

	 	By:
	 	Cash Flow Asset Management, L.P.,
	 

	 	 	 	a Texas limited partnership, its sole manager

	 	 	 	 	 
	 

	 	By:
	 	CFAM GP, L.L.C.,
	 

	 	 	 	a Texas limited liability company, its sole general partner

	 	 	 	 	 
	 	 	 
	 	By:  	               /s/ John W. Emerson
 	 
	 	 	Name:  	John W. Emerson 	 
	 	 	Title:  	Vice President

Effective Date:  April 25, 2008 	 
	 

	 	 	 
	TENANT:

	 	CUMBERLAND PHARMACEUTICALS INC., a Tennessee corporation

	 	 	 	 	 
	 	 	 
	 	By:  	               /s/ A.J. Kazimi
 	 
	 	 	Name:  	A.J. Kazimi 	 
	 	 	Title:  	CEO 	 

 

	 	 	 	 	 

EXHIBIT “A”

FIRST EXPANSION SPACE

[to be attached]

Ex. A-i

 

EXHIBIT “B”

BASE RENTAL

	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	 	 	 	FIRST	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	ORIGINAL	 	 	EXPANSION	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	PREMISES	 	 	SPACE	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	FIRST	 	 	 	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	ORIGINAL	 	 	EXPANSION	 	 	 	 
	 	 	 	 	 	 	ANNUAL	 	 	ANNUAL	 	 	PREMISES	 	 	SPACE	 	 	 	 
	 	 	 	 	 	 	BASE	 	 	BASE	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	RENTAL	 	 	RENTAL	 	 	 	 	 	 	 	 	 	 	MONTHLY	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	BASE	 
	PERIOD	 	 	RATE	 	 	RATE	 	 	RSF	 	 	RSF	 	 	RENTAL	 
	1/1/2008
	 	 	5/30/2008	 	 	$	[***]	 	 	 	 	 	 	 	6,341	 	 	 	 	 	 	$	[***]	 
	6/1/2008
	 	 	7/31/2008	 	 	$	[***]	 	 	$	[***]	 	 	 	6,341	 	 	 	2,950	 	 	$	[***]	 
	8/1/2008
	 	 	12/31/2008	 	 	$	[***]	 	 	$	[***]	 	 	 	6,341	 	 	 	2,950	 	 	$	[***]	 
	1/1/2009
	 	 	5/30/2009	 	 	$	[***]	 	 	$	[***]	 	 	 	6,341	 	 	 	2,950	 	 	$	[***]	 
	6/1/2009
	 	 	12/31/2009	 	 	$	[***]	 	 	$	[***]	 	 	 	6,341	 	 	 	2,950	 	 	$	[***]	 
	1/1/2010
	 	 	5/31/2010	 	 	$	[***]	 	 	$	[***]	 	 	 	6,341	 	 	 	2,950	 	 	$	[***]	 
	6/1/2010
	 	 	12/31/2010	 	 	$	[***]	 	 	$	[***]	 	 	 	6,341	 	 	 	2,950	 	 	$	[***]	 
	1/1/2011
	 	 	5/31/2011	 	 	 	 	 	 	$	[***]	 	 	 	 	 	 	 	2,950	 	 	$	[***]	 
	6/1/2011
	 	 	5/31/2012	 	 	 	 	 	 	$	[***]	 	 	 	 	 	 	 	2,950	 	 	$	[***]	 
	6/1/2012
	 	 	5/31/2013	 	 	 	 	 	 	$	[***]	 	 	 	 	 	 	 	2,950	 	 	$	[***]	 
	6/1/2013
	 	 	5/31/2014	 	 	 	 	 	 	$	[***]	 	 	 	 	 	 	 	2,950	 	 	$	[***]	 
	6/1/2014
	 	 	5/31/2015	 	 	 	 	 	 	$	[***]	 	 	 	 	 	 	 	2,950	 	 	$	[***]	 
	6/1/2015
	 	 	12/31/2015	 	 	 	 	 	 	$	[***]	 	 	 	 	 	 	 	2,950	 	 	$	[***]	 

Ex. B-i

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