Document:

Form of senior subordinated convertible demand promissory note

 Exhibit 10.5 
 THIS NOTE HAS BEEN, AND THE SHARES OF COMMON STOCK OR NEW SECURITIES WHICH MAY BE RECEIVED PURSUANT TO THE CONVERSION OF THIS NOTE WILL BE, ACQUIRED SOLELY FOR INVESTMENT AND NOT WITH A VIEW TO, OR FOR
RESALE IN CONNECTION WITH, ANY DISTRIBUTION THEREOF. NEITHER THIS NOTE NOR SUCH SHARES OF COMMON STOCK OR NEW SECURITIES HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR QUALIFIED UNDER ANY STATE
SECURITIES LAWS. SUCH SECURITIES MAY NOT BE SOLD OR OFFERED FOR SALE IN THE ABSENCE OF SUCH REGISTRATION OR QUALIFICATION OR AN OPINION OF COUNSEL IN FORM AND SUBSTANCE REASONABLY SATISFACTORY TO THE COMPANY THAT SUCH DISPOSITION IS EXEMPT FROM THE
REGISTRATION REQUIREMENTS OF THE ACT AND ANY REGISTRATION OR QUALIFICATION REQUIREMENTS UNDER APPLICABLE STATE SECURITIES LAWS. 
 THIS NOTE IS
SUBJECT TO AN INTERCREDITOR AND SUBORDINATION AGREEMENT DATED AS OF THE DATE HEREOF AMONG THE ADMINISTRATIVE AGENT NAMED THEREIN AND THE PURCHASERS NAMED THEREIN (INCLUDING THE HOLDER), AND ACKNOWLEDGED BY THE COMPANY WHICH, AMONG OTHER THINGS,
SUBORDINATES THE COMPANY’S OBLIGATIONS TO THE PURCHASER TO THE COMPANY’S OBLIGATIONS TO THE SENIOR LENDERS AS FURTHER DESCRIBED THEREIN. 
 RIB-X PHARMACEUTICALS, INC. 
 Senior Subordinated Convertible Demand
Promissory Note (the “Note”) 
  

			
	$             (the “Principal Amount”)	  	New York, NY
		  	                 , 2010

 Rib-X Pharmaceuticals, Inc., a Delaware corporation (the “Company”), for value received,
hereby promises to pay to                      or its assigns (collectively, the “Holder”) the Principal Amount together with
interest (computed on the basis of a 365-day year for the actual number of days elapsed) accruing daily and compounding quarterly from the date hereof on the unpaid balance of the Principal Amount from time to time outstanding at the rate of ten
percent (10%) per annum (the “Interest”) until the Principal Amount and Interest are paid in full or converted as provided herein. Capitalized terms used herein but not defined shall have the meanings given to such terms in the
Senior Subordinated Convertible Demand Promissory Note Purchase Agreement (the “Note Purchase Agreement”), dated as of May 28, 2010, by and among the Company and the Purchasers (as defined therein). It is acknowledged that the
Senior Subordinated Convertible Demand Promissory Notes issued pursuant to the Note Purchase Agreement, of which this Note is one, are being issued at the First Closing in an aggregate amount of approximately $5,500,000 (such Senior Subordinated
Convertible Demand Promissory Notes, the “Initial Notes”) and the holders of such notes, collectively, the “Noteholders”). It is further acknowledged that the Company may issue additional Senior

 
Subordinated Convertible Demand Promissory Notes to the Noteholders in an aggregate amount of $9,500,000 pursuant to the terms and conditions of the Note Purchase Agreement at one or more
Subsequent Closings (the “Subsequent Notes” and together with the Initial Notes the “Senior Notes”). 
 Subject to Section 2 of this Senior Note, the Principal Amount and the Interest thereon, unless previously converted or repaid as provided herein, shall be due and payable by the Company in
cash on May 28, 2015 (the “Maturity Date”). Payments hereunder are to be made without defense, setoff, counterclaim or recoupment in lawful money of the United States of America in same day or immediately available funds to the
account of the Holder specified from time to time by the Holder to the Company. 
 Subject to any applicable notice periods, all
parties to this Senior Note, including the Company and any sureties, endorsers, or guarantors, hereby waive protest, presentment, notice of dishonor, and notice of acceleration of maturity and agree to continue to remain bound for the payment of the
Principal Amount, the Interest and all other sums due under this Senior Note notwithstanding any change or changes by way of release, surrender, exchange, modification or substitution of any security for this Senior Note or by way of any extension
or extensions of time for the payment of the Principal Amount and the Interest and all such parties waive all and every kind of notice of such change or changes and agree that the same may be without notice or consent of any of them. 

Following an Event of Default (as defined herein), the Noteholders who hold Senior Notes representing at least a majority of the
aggregate principal amount owed by the Company pursuant to the then outstanding Senior Notes (the “Senior Subordinated Majority”) may (i) elect to pursue the rights of the Noteholders under this Senior Note and all other Senior
Notes and (ii) collectively employ an attorney to enforce their rights and remedies under this Senior Note and all other Notes and the Company and any surety, guarantor or endorser of this Senior Note hereby agree to pay to the
Noteholders’ reasonable attorneys’ fees, plus all other reasonable expenses incurred by the Noteholders in exercising any such rights and remedies. The rights and remedies of the Noteholders as provided in this Senior Note and all other
Senior Notes shall be cumulative and each such right or remedy may be pursued singly, successively, or together against any other funds, property or security held by the Noteholders for payment or security, in the sole discretion of the Senior
Subordinated Majority. The failure to exercise any such right or remedy shall not be a waiver or release of such rights or remedies or the right to exercise any of them at another time. 

As used herein, the term “Base Conversion Price” shall mean the Conversion Price (as defined in, and as adjusted
pursuant to, the Company’s Sixth Amended and Restated Certificate of Incorporation (the “Charter”)) of the Company’s Series C Preferred Stock; provided, however, if at any time there are no longer any shares
of the Company’s Series C Preferred Stock outstanding, the Base Conversion Price shall thereafter be adjusted as if one (1) share of Series C Preferred Stock continued to be outstanding. 

 

	1.	Conversion. 

  
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	 	(a)	In Connection With a Drag-Along Event. Subject to Sections 1(b) and 1(c) below, in the event of any transaction (including, without limitation, any change of
control transaction, joint venture, partnership, liquidation or Repayment Event (as defined herein)) approved by the Senior Eligible Securities Majority (as defined in the Charter), the Senior Subordinated Majority shall have the right, but not the
obligation, to elect to convert all or any portion of the amount then outstanding under this Senior Note including any accrued but unpaid Interest (the “Outstanding Amount”) (and a corresponding portion of the Outstanding Amounts
under all other Senior Notes) into the number of shares of common stock of the Company, par value $0.001 per share (“Common Stock”), that is equal to (i) the Outstanding Amount divided by (ii) the lowest of (x) the
Base Conversion Price as of the date of such conversion, (y) the Equity Financing Conversion Price (as defined herein) for the most recent offering of New Securities (as defined herein) and (z) the IPO Conversion Price (as defined herein).

  

	 	(b)	In Connection With an Equity Financing. In the event that the Company consummates any financing pursuant to which the Company or any affiliate thereof issues
equity securities, including without limitation, any security convertible or exchangeable into equity securities of the Company, which shall exclude for this purpose (i) any equity securities (and any security convertible or exchangeable into
equity securities) of the Company issued upon conversion of the Junior Notes or the Senior Notes or upon exercise or conversion of the Existing Warrants or Warrants and (ii) any equity securities issued or issuable to officers, founders,
employees or directors of, or consultants to, the Company pursuant to a stock purchase or option plan or other compensatory stock arrangements existing as of May 28, 2010 or as otherwise approved by the Board of Directors of the Company (the
“New Securities”) prior to the Maturity Date, the Senior Subordinated Majority shall have the right, but not the obligation, to elect to convert all or any portion of the Outstanding Amount under this Senior Note (and a
corresponding portion of the Outstanding Amounts under all other Senior Notes) into the number of New Securities that is equal to (A) the Outstanding Amount being converted under this Senior Note (and the corresponding Outstanding Amounts being
converted under all other Senior Notes) divided by (B) the lesser of (1) the Base Conversion Price as of the date of such conversion and (2) thirty-three percent (33%) of the price per New Security at which the New Security is
sold to investors in the financing (the “Equity Financing Conversion Price”). 

  

	 	(c)	 In Connection With an Initial Public Offering. In the event that the Company consummates an initial public offering of its Common Stock (the
“IPO”) prior to the Maturity Date, the Senior Subordinated Majority shall have the right, but not the obligation, to elect to convert all or any portion of the Outstanding Amount under this Senior Note (and a corresponding portion
of the Outstanding Amounts under all other Senior Notes) into the number of shares of Common Stock that is equal to (1) the Outstanding Amount being converted under this Senior Note (and the corresponding Outstanding Amounts being converted
under all other Senior 

  
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Notes) divided by (2) the lesser of (y) Base Conversion Price as of the date of such conversion and (z) thirty-three percent (33%) of the amount per share for which the
Company issues securities in the IPO (the “IPO Conversion Price”). 

  

	 	(d)	Mechanics of Conversion. 

  

	 	(i)	In connection with any conversion of the Senior Note pursuant to this Section 1, the Holder shall provide notice to the Company, which shall state such
Holder’s name or the names of his or its nominees in which such Holder wishes the shares of Common Stock or the New Securities to be issued upon conversion. Promptly following such conversion the Company shall update the books and records of
the Company to evidence the issuance of the applicable shares of Common Stock or New Securities to the Holder. 

  

	 	(ii)	Immediately upon any conversion of the Senior Note pursuant to this Section 1, this Senior Note shall no longer be deemed to be outstanding and all rights
of the holder with respect to this Senior Note shall immediately cease and terminate, except the right of the holder to receive the applicable shares of Common Stock or New Securities to which it is entitled as a result of such conversion.

  

	 	(iii)	The Company shall pay any and all issue and other taxes that may be payable in respect of any issuance or delivery of the applicable shares of Common Stock or New
Securities upon any conversion of this Senior Note pursuant to this Section 1. The Company shall not, however, be required to pay any tax which may be payable in respect of any transfer involved in the issuance and delivery of the
applicable shares of Common Stock or New Securities in a name other than that of the registered Holder of this Senior Note, and no such issuance or delivery shall be made unless and until the person or entity requesting such issuance has paid to the
Company the amount of any such tax or has established, to the satisfaction of the Company, that such tax has been paid. 

  

	 	(iv)	Any conversion hereunder of a portion of, but not all, the Senior Notes shall be pro rata among the Holders based on the Outstanding Amount held by each Holder.

  

	 	(f)	Reservation of Common Stock. During the period within which this Senior Note may be converted pursuant to this Section 1, the Company shall at all
times have authorized and reserved for issuance a sufficient number of shares of its Common Stock to provide for the conversion of the then Outstanding Amount. 

 

	2.	Repayment. 

  

	 	(a)	 Upon a Change of Control or Liquidation. In the event of (a) any liquidation, dissolution or winding up of the affairs of the Company,
(b) any consolidation, merger or other business combination of the Company (other than a consolidation, 

  
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merger, or combination in which the stockholders of the Company immediately prior to the transaction possess more than fifty percent (50%) of the voting securities of the surviving or
resulting entity immediately after the transaction), (c) any sale or disposition of a majority of the Company’s equity interests (calculated on an as-converted basis) to any person or entity who is not an equityholder of the Company as of
the date hereof, (d) any sale, license or disposition of all or substantially all of the assets of the Company, (e) any Public Company Merger or (f) any other event in which the Series B and Series C Liquidation Preference (as defined
in the Charter) would be payable to the holders of Series B Preferred Stock of the Company and Series C Preferred Stock of the Company (each a “Repayment Event”), upon the written election of the Senior Subordinated Majority
delivered to the Company the Holder shall automatically be entitled to receive, in full satisfaction of the Company’s repayment obligations under this Senior Note, the greater of (i) the sum of (y) three and one-half times
(3.5x) the Principal Amount plus (z) any then accrued but unpaid Interest and (ii) the amount that the Holder would be entitled to receive if the Outstanding Amount converted into shares of Common Stock immediately prior to the
Repayment Event at the lesser of (1) Base Conversion Price as of the date of such Repayment Event and (2) thirty-three percent (33%) of the fair market value of a share of Common Stock at the time of the Repayment Event. It is
understood and agreed that the Holder’s rights under this Section 2(a) shall survive any Repayment Event as to which the Senior Subordinated Majority does not elect to exercise its right to repayment pursuant to this Section 2(a),
with such changes to the defined term “Company” as are necessary to reflect structural changes resulting from such Repayment Event. In connection with any Repayment Event that is a Public Company Merger, the Holder may elect to receive any
of the payments contemplated by this Section 2(a) either in (A) cash, (B) securities issued by the surviving entity in connection with such Public Company Merger (which securities issued by the surviving entity shall be valued based
on the price per such security (or value per such security) in such Public Company Merger) or any combination of the foregoing (A) and (B). “Public Company Merger” shall mean any merger of the Company with or into any other entity a
result of which is that shares of common stock or equity securities of the surviving entity (or an affiliate thereof) received by the holders of securities of the Company pursuant to such merger are listed on the New York Stock Exchange or the
Nasdaq Stock Market or other stock exchange or listing system, or trade on any electronic quotation system, “Pink Sheets”, “OTCBB” or any similar system. 

 

	 	(b)	Upon Demand. Upon the written election of the Senior Subordinated Majority, given following the earlier of (i) March 31, 2011 and (ii) the date on
which the Company enters into an exclusive product licensing transaction which provides at least $30,000,000 in up-front net cash proceeds to the Company, the Company shall promptly (and in any event within ten (10) business days of receipt of
such notice) repay the Outstanding Amount under this Senior Note and the corresponding Outstanding Amounts under all other Senior Notes. All such repayments shall be made pro rata among the Senior Notes based on the amounts then outstanding under
each such Senior Note. 

  
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	 	(c)	No Prepayment. Except as contemplated by this Section 2, in no event shall the Company have the right or the obligation to repay any portion of the
Principal Amount or any Interest thereon or any portion of the amounts owed by the Company under any other Senior Note prior to the Maturity Date. 

  

	3.	Restrictions on Transfer. This Senior Note and the equity interests into which the Senior Note may be converted, shall not be assigned, sold, pledged,
transferred or otherwise disposed of except in compliance with the terms of the Third Amended and Restated Stockholders Agreement, dated as of June 8, 2006, by and among the Stockholders (as defined therein) and the Company, as amended to date
(as so amended, the “Stockholders Agreement”) and only with the prior written consent of the Senior Subordinated Majority. For purposes of Section 3 and Section 4 of the Stockholders Agreement, the Holder
shall be deemed to hold the number of shares of Common Stock into which this Senior Note could be converted pursuant to Section 1. Any shares of Common Stock or New Securities issuable upon a conversion pursuant to Section 1
shall be subject to the terms and conditions of the Stockholders Agreement that are applicable to the Holder. 

  

	4.	Default. This Senior Note and all amounts due hereunder shall become immediately due and payable in cash at the election of the Senior Subordinated Majority upon
the occurrence at any time of any of the following events of default (individually, an “Event of Default” and collectively, “Events of Default”): 

 

	 	(a)	default in the payment when due of any portion of the Principal Amount or any Interest thereon; 

 

	 	(b)	the liquidation, termination of existence, dissolution or the appointment of a receiver or custodian for the Company or any part of its property if such appointment is
not terminated or dismissed within thirty (30) days; 

  

	 	(c)	the institution against the Company or any endorser or guarantor of this Senior Note of any proceedings under the United States Bankruptcy Code or any other federal or
state bankruptcy, reorganization, receivership, insolvency or other similar law affecting the rights of creditors generally, which proceeding is not dismissed within thirty (30) days of filing; 

 

	 	(d)	the institution by the Company or any endorser or guarantor of this Senior Note of any proceedings under the United States Bankruptcy Code or any other federal or state
bankruptcy, reorganization, receivership, insolvency or other similar law affecting the rights of creditors generally or the making by the Company or any endorser or guarantor of this Senior Note of a composition or an assignment or trust mortgage
for the benefit of creditors; 

  

	 	(e)	the material breach of any covenant set forth in the Note Purchase Agreement or this Senior Note which breach remains uncured ten (10) days after written notice
thereof by any Noteholder to the Company; 

  

	 	(f)	the occurrence of an Event of Default under the Junior Notes; 

  
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	 	(g)	the failure of any of the Company’s representations or warranties set forth in Article II of the Note Purchase Agreement to be true and correct (i) in all
respects on the Initial Closing Date (as defined in the Note Purchase Agreement) or (ii) in all material respects on each Subsequent Closing Date (as defined in the Note Purchase Agreement); or 

 

	 	(h)	the occurrence of any event upon which, whether with the giving of notice, the passage of time or otherwise, would allow the Holder or holders of any indebtedness of
the Company or any of its subsidiaries to accelerate or otherwise demand repayment or repurchase prior to the scheduled maturity thereof of any such indebtedness or the acceleration of any such indebtedness. 

Upon the occurrence of an Event of Default, the Holder shall have then, or at any time thereafter, all of the rights and remedies
afforded by the Uniform Commercial Code as from time to time in effect in the State of Delaware or afforded by other applicable law. 
  

	5.	General. 

  

	 	(a)	Successors and Assigns. This Senior Note, and the obligations and rights of the Company hereunder, shall be binding upon and inure to the benefit of the Company,
the Holder, and their respective heirs, successors and permitted assigns. 

  

	 	(b)	Recourse. Recourse under this Senior Note shall be to the Company and its assets only, and in no event to the officers, directors or shareholders of the Company.

  

	 	(c)	Changes. Changes in or additions to this Senior Note may be made or compliance with any term, covenant, agreement, condition or provision set forth herein may be
omitted or waived (either generally or in a particular instance and either retroactively or prospectively) upon written consent of the Company and the Senior Subordinated Majority and shall not, for the avoidance of doubt, separately require the
consent of the Holder; provided, however, any amendment modification or waiver of a provision of the Senior Notes that by its terms treats the Holder in a materially different and adverse manner relative to the other Noteholders shall
not be binding as to the Holder unless the Holder consents in writing to the amendment, modification or waiver; provided, further, that no such amendment, waiver or consent shall: (i) reduce the principal amount outstanding
hereunder without the Holder’s written consent, or (ii) reduce the rate of interest hereof without the Holder’s written consent. 

  

	 	(d)	Governing Law. This Senior Note shall be governed by and construed in accordance with the law of the State of Delaware, excluding the body of law relating to
conflict of laws. Notwithstanding anything to the contrary contained herein, in no event may the effective rate of interest collected or received by the holder hereof exceed that which may be charged, collected or received by the holder under
applicable law. 

  
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	 	(e)	 Notices. All notices, requests, consents and demands shall be made in writing and shall be mailed postage prepaid, or delivered by hand, to the
Company at the Company’s principal offices or to the Holder at the address of the Holder set forth in the Note Purchase Agreement or to such other address as may be furnished in writing to the other party hereto, and in addition may be
delivered by telex, telecopy, electronic mail or facsimile transmission. All notices, requests, consents and other communications hereunder shall be deemed to have been given either (i) if by hand, at the time of the delivery thereof to the
receiving party at the address of such party set forth above, (ii) if made by telex, telecopy, electronic mail or facsimile transmission, at the time that receipt thereof has been acknowledged by electronic confirmation or otherwise,
(iii) if sent by overnight courier, on the next business day following the day such notice is delivered to the courier service, or (iv) if sent by registered or certified mail, on the 3rd business day following the day such mailing is made.

  

	 	(f)	Jurisdiction. THE COMPANY AGREES THAT ANY SUIT FOR THE ENFORCEMENT OF THIS SENIOR NOTE, THE NOTE PURCHASE AGREEMENT OR ANY OTHER RELATED DOCUMENT MAY BE BROUGHT
IN THE COURTS OF THE STATE OF NEW YORK OR ANY FEDERAL COURT SITTING THEREIN AND CONSENTS TO THE NONEXCLUSIVE JURISDICTION OF SUCH COURTS AND SERVICE OF PROCESS IN ANY SUCH SUIT BEING MADE UPON THE COMPANY AT ITS PRINCIPAL OFFICES. THE COMPANY HEREBY
WAIVES ANY OBJECTION THAT IT MAY NOW OR HEREAFTER HAVE TO THE VENUE OF ANY SUCH SUIT OR ANY SUCH COURT OR THAT SUCH SUIT IS BROUGHT IN AN INCONVENIENT COURT. 

 

	 	(g)	Trial by Jury. The Company hereby waives its right to a jury trial with respect to any action or claim arising out of any dispute in connection with this Note,
any rights or obligations hereunder or the performance of such rights and obligations. 

  

	 	(h)	To the extent permitted by applicable law, the Company shall not assert, and hereby waives, any claim against any Noteholder and their respective affiliates, directors,
employees, attorneys, agents or sub-agents, for special, indirect, consequential or punitive damages arising out of, in connection with, as a result of or related to, this Note, the transactions contemplated hereby or thereby, the Loan or the use of
the proceeds thereof. 

 [Remainder of Page Intentionally Left Blank] 

  
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 IN WITNESS WHEREOF, this Note has been executed and delivered on the date first above
written by the duly authorized representative of the Company. 
  

			
	RIB-X PHARMACEUTICALS, INC.
		
	By:	 	  

	Name:	 	Mark Leuchtenberger
	Title:	 	President and Chief Executive OfficerForm of senior subordinated convertible demand promissory note

 Exhibit 10.6 
 THIS NOTE HAS BEEN, AND THE SHARES OF COMMON STOCK OR NEW SECURITIES WHICH MAY BE RECEIVED PURSUANT TO THE CONVERSION OF THIS NOTE WILL BE, ACQUIRED SOLELY FOR INVESTMENT AND NOT WITH A VIEW TO, OR FOR
RESALE IN CONNECTION WITH, ANY DISTRIBUTION THEREOF. NEITHER THIS NOTE NOR SUCH SHARES OF COMMON STOCK OR NEW SECURITIES HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR QUALIFIED UNDER ANY STATE
SECURITIES LAWS. SUCH SECURITIES MAY NOT BE SOLD OR OFFERED FOR SALE IN THE ABSENCE OF SUCH REGISTRATION OR QUALIFICATION OR AN OPINION OF COUNSEL IN FORM AND SUBSTANCE REASONABLY SATISFACTORY TO THE COMPANY THAT SUCH DISPOSITION IS EXEMPT FROM THE
REGISTRATION REQUIREMENTS OF THE ACT AND ANY REGISTRATION OR QUALIFICATION REQUIREMENTS UNDER APPLICABLE STATE SECURITIES LAWS. 
 THIS NOTE IS
SUBJECT TO AN INTERCREDITOR AND SUBORDINATION AGREEMENT DATED AS OF MAY 28, 2010 AMONG THE ADMINISTRATIVE AGENT NAMED THEREIN AND THE PURCHASERS NAMED THEREIN (INCLUDING THE HOLDER), AND ACKNOWLEDGED BY THE COMPANY WHICH, AMONG OTHER THINGS,
SUBORDINATES THE COMPANY’S OBLIGATIONS TO THE PURCHASER TO THE COMPANY’S OBLIGATIONS TO THE SENIOR LENDERS AS FURTHER DESCRIBED THEREIN. 
 RIB-X PHARMACEUTICALS, INC. 
 Senior Subordinated Convertible Demand
Promissory Note (the “Note”) 
  

			
	$             (the “Principal Amount”)	  	New York, NY
		  	August     , 2010

 Rib-X Pharmaceuticals, Inc., a Delaware corporation (the “Company”), for value received, hereby promises
to pay to                      or its assigns (collectively, the “Holder”) the Principal Amount together with interest (computed on
the basis of a 365-day year for the actual number of days elapsed) accruing daily and compounding quarterly from the date hereof on the unpaid balance of the Principal Amount from time to time outstanding at the rate of ten percent (10%) per
annum (the “Interest”) until the Principal Amount and Interest are paid in full or converted as provided herein. Capitalized terms used herein but not defined shall have the meanings given to such terms in the Senior Subordinated
Convertible Demand Promissory Note Purchase Agreement (the “Note Purchase Agreement”), dated as of May 28, 2010, by and among the Company and the Purchasers (as defined therein). It is acknowledged that the Senior Subordinated
Convertible Demand Promissory Notes issued pursuant to the Note Purchase Agreement, of which this Note is one, are being issued at the Second Closing in an aggregate amount of approximately $5,400,000 (such Senior Subordinated Convertible Demand
Promissory Notes, the “Second Closing Notes” and the holders of such notes, collectively, the “Noteholders”). It is further acknowledged that the Company may issue additional Senior

 
Subordinated Convertible Demand Promissory Notes to the Noteholders in an aggregate amount of $4,100,000 pursuant to the terms and conditions of the Note Purchase Agreement at one or more
Subsequent Closings (the “Subsequent Notes” and together with the Second Closing Notes and the initial notes issued on or around May 28, 2010 pursuant to the Note Purchase Agreement, the “Senior Notes”).

 Subject to Section 2 of this Senior Note, the Principal Amount and the Interest thereon, unless previously
converted or repaid as provided herein, shall be due and payable by the Company in cash on August 25, 2015 (the “Maturity Date”). Payments hereunder are to be made without defense, setoff, counterclaim or recoupment in lawful
money of the United States of America in same day or immediately available funds to the account of the Holder specified from time to time by the Holder to the Company. 
 Subject to any applicable notice periods, all parties to this Senior Note, including the Company and any sureties, endorsers, or guarantors, hereby waive protest, presentment, notice of dishonor, and
notice of acceleration of maturity and agree to continue to remain bound for the payment of the Principal Amount, the Interest and all other sums due under this Senior Note notwithstanding any change or changes by way of release, surrender,
exchange, modification or substitution of any security for this Senior Note or by way of any extension or extensions of time for the payment of the Principal Amount and the Interest and all such parties waive all and every kind of notice of such
change or changes and agree that the same may be without notice or consent of any of them. 
 Following an Event of Default (as
defined herein), the Noteholders who hold Senior Notes representing at least a majority of the aggregate principal amount owed by the Company pursuant to the then outstanding Senior Notes (the “Senior Subordinated Majority”) may
(i) elect to pursue the rights of the Noteholders under this Senior Note and all other Senior Notes and (ii) collectively employ an attorney to enforce their rights and remedies under this Senior Note and all other Senior Notes and the
Company and any surety, guarantor or endorser of this Senior Note hereby agree to pay to the Noteholders’ reasonable attorneys’ fees, plus all other reasonable expenses incurred by the Noteholders in exercising any such rights and
remedies. The rights and remedies of the Noteholders as provided in this Senior Note and all other Senior Notes shall be cumulative and each such right or remedy may be pursued singly, successively, or together against any other funds, property or
security held by the Noteholders for payment or security, in the sole discretion of the Senior Subordinated Majority. The failure to exercise any such right or remedy shall not be a waiver or release of such rights or remedies or the right to
exercise any of them at another time. 
 As used herein, the term “Base Conversion Price” shall mean the
Conversion Price (as defined in, and as adjusted pursuant to, the Company’s Sixth Amended and Restated Certificate of Incorporation (the “Charter”)) of the Company’s Series C Preferred Stock; provided,
however, if at any time there are no longer any shares of the Company’s Series C Preferred Stock outstanding, the Base Conversion Price shall thereafter be adjusted as if one (1) share of Series C Preferred Stock continued to be
outstanding. 

  
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	1.	Conversion. 

  

	 	(a)	In Connection With a Drag-Along Event. Subject to Sections 1(b) and 1(c) below, in the event of any transaction (including, without limitation, any change of
control transaction, joint venture, partnership, liquidation or Repayment Event (as defined herein)) approved by the Senior Eligible Securities Majority (as defined in the Charter), the Senior Subordinated Majority shall have the right, but not the
obligation, to elect to convert all or any portion of the amount then outstanding under this Senior Note including any accrued but unpaid Interest (the “Outstanding Amount”) (and a corresponding portion of the Outstanding Amounts
under all other Senior Notes) into the number of shares of common stock of the Company, par value $0.001 per share (“Common Stock”), that is equal to (i) the Outstanding Amount divided by (ii) the lowest of (x) the
Base Conversion Price as of the date of such conversion, (y) the Equity Financing Conversion Price (as defined herein) for the most recent offering of New Securities (as defined herein) and (z) the IPO Conversion Price (as defined herein).

  

	 	(b)	In Connection With an Equity Financing. In the event that the Company consummates any financing pursuant to which the Company or any affiliate thereof issues
equity securities, including without limitation, any security convertible or exchangeable into equity securities of the Company, which shall exclude for this purpose (i) any equity securities (and any security convertible or exchangeable into
equity securities) of the Company issued upon conversion of the Junior Notes or the Senior Notes or upon exercise or conversion of the Existing Warrants or Warrants and (ii) any equity securities issued or issuable to officers, founders,
employees or directors of, or consultants to, the Company pursuant to a stock purchase or option plan or other compensatory stock arrangements existing as of May 28, 2010 or as otherwise approved by the Board of Directors of the Company (the
“New Securities”) prior to the Maturity Date, the Senior Subordinated Majority shall have the right, but not the obligation, to elect to convert all or any portion of the Outstanding Amount under this Senior Note (and a
corresponding portion of the Outstanding Amounts under all other Senior Notes) into the number of New Securities that is equal to (A) the Outstanding Amount being converted under this Senior Note (and the corresponding Outstanding Amounts being
converted under all other Senior Notes) divided by (B) the lesser of (1) the Base Conversion Price as of the date of such conversion and (2) thirty-three percent (33%) of the price per New Security at which the New Security is
sold to investors in the financing (the “Equity Financing Conversion Price”). 

  

	 	(c)	 In Connection With an Initial Public Offering. In the event that the Company consummates an initial public offering of its Common Stock (the
“IPO”) prior to the Maturity Date, the Senior Subordinated Majority shall have the right, but not the obligation, to elect to convert all or any portion of the Outstanding Amount under this Senior Note (and a corresponding portion
of the Outstanding Amounts under all other Senior Notes) into the number of shares of Common Stock that is equal to (1) the Outstanding Amount being converted under this Senior Note (and the

  
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corresponding Outstanding Amounts being converted under all other Senior Notes) divided by (2) the lesser of (y) Base Conversion Price as of the date of such conversion and
(z) thirty-three percent (33%) of the amount per share for which the Company issues securities in the IPO (the “IPO Conversion Price”). 

 

	 	(d)	Mechanics of Conversion. 

  

	 	(i)	In connection with any conversion of the Senior Note pursuant to this Section 1, the Holder shall provide notice to the Company, which shall state such
Holder’s name or the names of his or its nominees in which such Holder wishes the shares of Common Stock or the New Securities to be issued upon conversion. Promptly following such conversion the Company shall update the books and records of
the Company to evidence the issuance of the applicable shares of Common Stock or New Securities to the Holder. 

  

	 	(ii)	Immediately upon any conversion of the Senior Note pursuant to this Section 1, this Senior Note shall no longer be deemed to be outstanding and all rights
of the holder with respect to this Senior Note shall immediately cease and terminate, except the right of the holder to receive the applicable shares of Common Stock or New Securities to which it is entitled as a result of such conversion.

  

	 	(iii)	The Company shall pay any and all issue and other taxes that may be payable in respect of any issuance or delivery of the applicable shares of Common Stock or New
Securities upon any conversion of this Senior Note pursuant to this Section 1. The Company shall not, however, be required to pay any tax which may be payable in respect of any transfer involved in the issuance and delivery of the
applicable shares of Common Stock or New Securities in a name other than that of the registered Holder of this Senior Note, and no such issuance or delivery shall be made unless and until the person or entity requesting such issuance has paid to the
Company the amount of any such tax or has established, to the satisfaction of the Company, that such tax has been paid. 

  

	 	(iv)	Any conversion hereunder of a portion of, but not all, the Senior Notes shall be pro rata among the Holders based on the Outstanding Amount held by each Holder.

  

	 	(f)	Reservation of Common Stock. During the period within which this Senior Note may be converted pursuant to this Section 1, the Company shall at all
times have authorized and reserved for issuance a sufficient number of shares of its Common Stock to provide for the conversion of the then Outstanding Amount. 

 

	2.	Repayment. 

  

	 	(a)	 Upon a Change of Control or Liquidation. In the event of (a) any liquidation, dissolution or winding up of the affairs of the Company,
(b) any consolidation, 

  
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merger or other business combination of the Company (other than a consolidation, merger, or combination in which the stockholders of the Company immediately prior to the transaction possess more
than fifty percent (50%) of the voting securities of the surviving or resulting entity immediately after the transaction), (c) any sale or disposition of a majority of the Company’s equity interests (calculated on an as-converted
basis) to any person or entity who is not an equityholder of the Company as of the date hereof, (d) any sale, license or disposition of all or substantially all of the assets of the Company, (e) any Public Company Merger or (f) any
other event in which the Series B and Series C Liquidation Preference (as defined in the Charter) would be payable to the holders of Series B Preferred Stock of the Company and Series C Preferred Stock of the Company (each a “Repayment
Event”), upon the written election of the Senior Subordinated Majority delivered to the Company the Holder shall automatically be entitled to receive, in full satisfaction of the Company’s repayment obligations under this Senior Note,
the greater of (i) the sum of (y) three and one-half times (3.5x) the Principal Amount plus (z) any then accrued but unpaid Interest and (ii) the amount that the Holder would be entitled to receive if the Outstanding
Amount converted into shares of Common Stock immediately prior to the Repayment Event at the lesser of (1) Base Conversion Price as of the date of such Repayment Event and (2) thirty-three percent (33%) of the fair market value of a
share of Common Stock at the time of the Repayment Event. It is understood and agreed that the Holder’s rights under this Section 2(a) shall survive any Repayment Event as to which the Senior Subordinated Majority does not elect to
exercise its right to repayment pursuant to this Section 2(a), with such changes to the defined term “Company” as are necessary to reflect structural changes resulting from such Repayment Event. In connection with any Repayment Event
that is a Public Company Merger, the Holder may elect to receive any of the payments contemplated by this Section 2(a) either in (A) cash, (B) securities issued by the surviving entity in connection with such Public Company Merger
(which securities issued by the surviving entity shall be valued based on the price per such security (or value per such security) in such Public Company Merger) or any combination of the foregoing (A) and (B). “Public Company Merger”
shall mean any merger of the Company with or into any other entity a result of which is that shares of common stock or equity securities of the surviving entity (or an affiliate thereof) received by the holders of securities of the Company pursuant
to such merger are listed on the New York Stock Exchange or the Nasdaq Stock Market or other stock exchange or listing system, or trade on any electronic quotation system, “Pink Sheets”, “OTCBB” or any similar system.

  

	 	(b)	 Upon Demand. Upon the written election of the Senior Subordinated Majority, given following the earlier of (i) March 31, 2011 and
(ii) the date on which the Company enters into an exclusive product licensing transaction which provides at least $30,000,000 in up-front net cash proceeds to the Company, the Company shall promptly (and in any event within ten
(10) business days of receipt of such notice) repay the Outstanding Amount under this Senior Note and the corresponding Outstanding Amounts under all other Senior Notes. All such

  
 -5-

	 	
repayments shall be made pro rata among the Senior Notes based on the amounts then outstanding under each such Senior Note. 

 

	 	(c)	No Prepayment. Except as contemplated by this Section 2, in no event shall the Company have the right or the obligation to repay any portion of the
Principal Amount or any Interest thereon or any portion of the amounts owed by the Company under any other Senior Note prior to the Maturity Date. 

  

	3.	Restrictions on Transfer. This Senior Note and the equity interests into which the Senior Note may be converted, shall not be assigned, sold, pledged,
transferred or otherwise disposed of except in compliance with the terms of the Third Amended and Restated Stockholders Agreement, dated as of June 8, 2006, by and among the Stockholders (as defined therein) and the Company, as amended to date
(as so amended, the “Stockholders Agreement”) and only with the prior written consent of the Senior Subordinated Majority. For purposes of Section 3 and Section 4 of the Stockholders Agreement, the Holder
shall be deemed to hold the number of shares of Common Stock into which this Senior Note could be converted pursuant to Section 1. Any shares of Common Stock or New Securities issuable upon a conversion pursuant to Section 1
shall be subject to the terms and conditions of the Stockholders Agreement that are applicable to the Holder. 

  

	4.	Default. This Senior Note and all amounts due hereunder shall become immediately due and payable in cash at the election of the Senior Subordinated Majority upon
the occurrence at any time of any of the following events of default (individually, an “Event of Default” and collectively, “Events of Default”): 

 

	 	(a)	default in the payment when due of any portion of the Principal Amount or any Interest thereon; 

 

	 	(b)	the liquidation, termination of existence, dissolution or the appointment of a receiver or custodian for the Company or any part of its property if such appointment is
not terminated or dismissed within thirty (30) days; 

  

	 	(c)	the institution against the Company or any endorser or guarantor of this Senior Note of any proceedings under the United States Bankruptcy Code or any other federal or
state bankruptcy, reorganization, receivership, insolvency or other similar law affecting the rights of creditors generally, which proceeding is not dismissed within thirty (30) days of filing; 

 

	 	(d)	the institution by the Company or any endorser or guarantor of this Senior Note of any proceedings under the United States Bankruptcy Code or any other federal or state
bankruptcy, reorganization, receivership, insolvency or other similar law affecting the rights of creditors generally or the making by the Company or any endorser or guarantor of this Senior Note of a composition or an assignment or trust mortgage
for the benefit of creditors; 

  

	 	(e)	the material breach of any covenant set forth in the Note Purchase Agreement or this Senior Note which breach remains uncured ten (10) days after written notice
thereof by any Noteholder to the Company; 

  
 -6-

	 	(f)	the occurrence of an Event of Default under the Junior Notes; 

  

	 	(g)	the failure of any of the Company’s representations or warranties set forth in Article II of the Note Purchase Agreement to be true and correct (i) in all
respects on the Initial Closing Date (as defined in the Note Purchase Agreement) or (ii) in all material respects on each Subsequent Closing Date (as defined in the Note Purchase Agreement); or 

 

	 	(h)	the occurrence of any event upon which, whether with the giving of notice, the passage of time or otherwise, would allow the Holder or holders of any indebtedness of
the Company or any of its subsidiaries to accelerate or otherwise demand repayment or repurchase prior to the scheduled maturity thereof of any such indebtedness or the acceleration of any such indebtedness. 

Upon the occurrence of an Event of Default, the Holder shall have then, or at any time thereafter, all of the rights and remedies
afforded by the Uniform Commercial Code as from time to time in effect in the State of Delaware or afforded by other applicable law. 
  

	5.	General. 

  

	 	(a)	Successors and Assigns. This Senior Note, and the obligations and rights of the Company hereunder, shall be binding upon and inure to the benefit of the Company,
the Holder, and their respective heirs, successors and permitted assigns. 

  

	 	(b)	Recourse. Recourse under this Senior Note shall be to the Company and its assets only, and in no event to the officers, directors or shareholders of the Company.

  

	 	(c)	Changes. Changes in or additions to this Senior Note may be made or compliance with any term, covenant, agreement, condition or provision set forth herein may be
omitted or waived (either generally or in a particular instance and either retroactively or prospectively) upon written consent of the Company and the Senior Subordinated Majority and shall not, for the avoidance of doubt, separately require the
consent of the Holder; provided, however, any amendment modification or waiver of a provision of the Senior Notes that by its terms treats the Holder in a materially different and adverse manner relative to the other Noteholders shall
not be binding as to the Holder unless the Holder consents in writing to the amendment, modification or waiver; provided, further, that no such amendment, waiver or consent shall: (i) reduce the principal amount outstanding
hereunder without the Holder’s written consent, or (ii) reduce the rate of interest hereof without the Holder’s written consent. 

  

	 	(d)	Governing Law. This Senior Note shall be governed by and construed in accordance with the law of the State of Delaware, excluding the body of law relating to
conflict of laws. Notwithstanding anything to the contrary contained herein, in no event may the effective rate of interest collected or received by the holder hereof exceed that which may be charged, collected or received by the holder under
applicable law. 

  
 -7-

	 	(e)	 Notices. All notices, requests, consents and demands shall be made in writing and shall be mailed postage prepaid, or delivered by hand, to the
Company at the Company’s principal offices or to the Holder at the address of the Holder set forth in the Note Purchase Agreement or to such other address as may be furnished in writing to the other party hereto, and in addition may be
delivered by telex, telecopy, electronic mail or facsimile transmission. All notices, requests, consents and other communications hereunder shall be deemed to have been given either (i) if by hand, at the time of the delivery thereof to the
receiving party at the address of such party set forth above, (ii) if made by telex, telecopy, electronic mail or facsimile transmission, at the time that receipt thereof has been acknowledged by electronic confirmation or otherwise,
(iii) if sent by overnight courier, on the next business day following the day such notice is delivered to the courier service, or (iv) if sent by registered or certified mail, on the 3rd business day following the day such mailing is made.

  

	 	(f)	Jurisdiction. THE COMPANY AGREES THAT ANY SUIT FOR THE ENFORCEMENT OF THIS SENIOR NOTE, THE NOTE PURCHASE AGREEMENT OR ANY OTHER RELATED DOCUMENT MAY BE BROUGHT
IN THE COURTS OF THE STATE OF NEW YORK OR ANY FEDERAL COURT SITTING THEREIN AND CONSENTS TO THE NONEXCLUSIVE JURISDICTION OF SUCH COURTS AND SERVICE OF PROCESS IN ANY SUCH SUIT BEING MADE UPON THE COMPANY AT ITS PRINCIPAL OFFICES. THE COMPANY HEREBY
WAIVES ANY OBJECTION THAT IT MAY NOW OR HEREAFTER HAVE TO THE VENUE OF ANY SUCH SUIT OR ANY SUCH COURT OR THAT SUCH SUIT IS BROUGHT IN AN INCONVENIENT COURT. 

 

	 	(g)	Trial by Jury. The Company hereby waives its right to a jury trial with respect to any action or claim arising out of any dispute in connection with this Note,
any rights or obligations hereunder or the performance of such rights and obligations. 

  

	 	(h)	To the extent permitted by applicable law, the Company shall not assert, and hereby waives, any claim against any Noteholder and their respective affiliates, directors,
employees, attorneys, agents or sub-agents, for special, indirect, consequential or punitive damages arising out of, in connection with, as a result of or related to, this Note, the transactions contemplated hereby or thereby, the Loan or the use of
the proceeds thereof. 

 [Remainder of Page Intentionally Left Blank] 

  
 -8-

 IN WITNESS WHEREOF, this Note has been executed and delivered on the date first above
written by the duly authorized representative of the Company. 
  

			
	RIB-X PHARMACEUTICALS, INC.
		
	By:	 	  

	Name: Mark Leuchtenberger
	Title: President and Chief Executive Officer

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