IP Library Granted Patent US 8,722,929
Granted Patent B2
US 8,722,929 · App. 11/870,368 · Granted May 13, 2014

N-[2-amino-4-(phenylmethoxy)phenyl] amides and related compounds as potassium channel modulators

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Quick Facts
Patent No.
US 8,722,929
App. No.
11/870,368
Granted
May 13, 2014
Kind
B2
Abstract

This invention provides compounds of formula A and formula B which are modulators of potassium ion channels and are useful for the treatment of seizure disorders.

Claims (8)

1. A compound of formula A

where Ar is phenyl U=—C(R m )═; R a and R′ a are, independently, H, F, Cl, methyl, methoxy, fluoromethyl, difluoromethyl, or trifluoromethyl; R m is H, F, Cl, methyl, fluoromethyl, difluoromethyl, trifluoromethyl or methoxy; R′ m is F, Cl, fluoromethyl, difluoromethyl, trifluoromethyl or methoxy; R N is H or

C 1 -C 4 alkyl, which may be straight-chain, branched, or cyclic; and R O is H, isopropyl, sec-butyl, or straight-chain C 1 -C 8 alkyl, alkenyl, or alkynyl, any of which may be substituted by methyl, fluoro, chloro methoxy, phenyl, or benzoyloxy, where the methyl, methoxy, phenyl, and benzyl groups are optionally substituted with one or two fluorine atoms or one or two chlorine atoms.

2. The compound of claim 1 , where R a is CF 3 , F, or Cl and R′ a is H or F.

3. The compound of claim 2 , where R′ m is F and R N is H or methyl.

4. The compound of claim 3 , where R O is C 1 -C 4 alkyl, C 1 -C 4 alkenyl, or CH 3 O—(CH 2 ) n CH 2 —, where n is 0, 1, 2, or 3.

5. The compound of claim 1 , where R O is selected from the group methyl, ethyl, propyl, butyl sec-butyl, pentyl, hexyl, 2-chloroethyl, 3-chloropropyl, 4-chlorobutyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, methoxyethyl, benzyloxyethyl, benzyl, o-chlorobenzyl, o-, o′-dichlorobenzyl o-fluorobenzyl, and o-, o′-difluorobenzyl.

6. A composition comprising a pharmaceutically acceptable carrier and one or more of the following: a compound of claim 1 ; a salt or ester thereof.

Assignments (22)
U.S. PATENT SECURITY AGREEMENT Recorded Nov 25, 2025
From: BAUSCH HEALTH IRELAND LIMITED
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 073715/0375 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH & LOMB PHARMA HOLDINGS CORP.; COMMONWEALTH LABORATORIES, LLC; DOW PHARMACEUTICAL SCIENCES, INC.; ECR PHARMACEUTICALS CO., INC.; LABORATOIRE CHAUVIN S.A.S.; MEDICIS PHARMACEUTICAL CORPORATION; ONPHARMA INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; SOLTA MEDICAL, INC.; SYNERGETICS USA, INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT CANADA LP; VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA LLC; WIRRA IP PTY LIMITED; VALEANT PHARMA POLAND SP. Z O.O.; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMACEUTICALS IRELAND LIMITED
Reel/Frame 073637/0001 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH AMERICAS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.
Reel/Frame 073637/0126 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH AMERICAS, INC.
Reel/Frame 073654/0242 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 15, 2025
From: VALEANT PHARMACEUTICALS INTERNATIONAL
To: BAUSCH HEALTH IRELAND LIMITED
Reel/Frame 071291/0339 →
RELEASE OF SECURITY INTEREST Recorded Apr 8, 2025
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: SOLTA MEDICAL, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH IRELAND LIMITED (F/K/A/ VALEANT PHARMACEUTICALS IRELAND LIMITED); SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD; SANTARUS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; HUMAX PHARMACEUTICAL S.A.; SOLTA MEDICAL IRELAND LIMITED; BAUSCH & LOMB MEXICO, S.A. DE C.V.; BAUSCH+LOMB OPS B.V.; BAUSCH HEALTH AMERICAS, INC.; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH HOLDCO LIMITED; BAUSCH HEALTH MAGYARORSZAG KFT (A/K/A BAUSCH HEALTH HUNGARY LLC); BAUSCH HEALTH POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA (F/K/A VALEANT PHARMA POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA); BAUSCH HEALTH US, LLC; BAUSCH HEALTH, CANADA INC. / SANTE BAUSCH, CANADA INC.; ICN POLFA RZESZOW SPOLKA AKCYJNA (A/K/A ICN POLFA RZESZOW S.A.); ORAPHARMA, INC.; PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA SPOLKA AKCYJNA (A/K/A PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA S.A.); SOLTA MEDICAL DUTCH HOLDINGS B.V.; V-BAC HOLDING CORP.; VRX HOLDCO LLC; 1261229 B.C. LTD.; 1530065 B.C. LTD.
Reel/Frame 070778/0199 →
SECURITY INTEREST Recorded Mar 15, 2023
From: BAUSCH HEALTH COMPANIES INC.; VALEANT CANADA LP; VALEANT CANADA GP LIMITED; V-BAC HOLDING CORP.; BAUSCH HEALTH, CANADA INC.
To: THE BANK OF NEW YORK MELLON
Reel/Frame 062983/0494 →
SECURITY INTEREST Recorded Feb 13, 2023
From: BAUSCH HEALTH COMPANIES INC.; VALEANT CANADA LP; VALEANT CANADA GP LIMITED; V-BAC HOLDING CORP.; BAUSCH HEALTH, CANADA INC.
To: THE BANK OF NEW YORK MELLON
Reel/Frame 062670/0260 →
SECURITY AGREEMENT (SECOND LIEN) Recorded Oct 5, 2022
From: BAUSCH HEALTH US, LLC; BAUSCH HEALTH AMERICAS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; SOLTA MEDICAL, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 061606/0468 →
SECURITY AGREEMENT (FIRST LIEN) Recorded Oct 4, 2022
From: BAUSCH HEALTH US, LLC; BAUSCH HEALTH AMERICAS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; SOLTA MEDICAL, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 061595/0066 →
SECURITY AGREEMENT Recorded Feb 10, 2022
From: BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH AMERICAS, INC.
To: THE BANK OF NEW YORK MELLON
Reel/Frame 059121/0001 →
SECURITY INTEREST Recorded Jun 8, 2021
From: BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH AMERICAS, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 056811/0814 →
SECURITY INTEREST Recorded Mar 11, 2019
From: BAUSCH HEALTH AMERICAS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 048556/0758 →
SECURITY INTEREST Recorded Feb 26, 2018
From: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH & LOMB PHARMA HOLDINGS CORP.; COMMONWEALTH LABORATORIES, LLC; DOW PHARMACEUTICAL SCIENCES, INC.; ECR PHARMACEUTICALS CO., INC.; LABORATOIRE CHAUVIN S.A.S.; MEDICIS PHARMACEUTICAL CORPORATION; ONPHARMA INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; SOLTA MEDICAL, INC.; SYNERGETICS USA, INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT CANADA LP; VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA LLC; WIRRA IP PTY LIMITED; VALEANT PHARMA POLAND SP. Z O.O.; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMACEUTICALS IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON, AS COLLATERAL AGENT
Reel/Frame 045444/0634 →
SECURITY INTEREST Recorded Feb 26, 2018
From: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH & LOMB PHARMA HOLDINGS CORP.; COMMONWEALTH LABORATORIES, LLC; DOW PHARMACEUTICAL SCIENCES, INC.; ECR PHARMACEUTICALS CO., INC.; LABORATOIRE CHAUVIN S.A.S.; MEDICIS PHARMACEUTICAL CORPORATION; ONPHARMA INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; SOLTA MEDICAL, INC.; SYNERGETICS USA, INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT CANADA LP; VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA LLC; WIRRA IP PTY LIMITED; VALEANT PHARMA POLAND SP. Z O.O.; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMACEUTICALS IRELAND LIMITED
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 045444/0299 →
SECURITY INTEREST Recorded Jul 19, 2017
From: VALEANT PHARMACEUTICALS INTERNATIONAL
To: THE BANK OF NEW YORK MELLON
Reel/Frame 043045/0913 →
NOTICE OF SUCCESSION OF AGENCY Recorded Jan 9, 2015
From: GOLDMAN SACHS LENDING PARTNERS, LLC
To: BARCLAYS BANK PLC, AS SUCCESSOR AGENT
Reel/Frame 034749/0689 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE NAME PREVIOUSLY RECORDED ON REEL 020760 FRAME 0563. ASSIGNOR(S) HEREBY CONFIRMS THE CONVEYING PARTIES HAVE CORRECTED THE ASSIGNEE'S NAME. Recorded Jul 28, 2011
From: VERNIER, JEAN-MICHEL; SONG, JIANLAN; CHEN, HUANMING; HONG, ZHI
To: VALEANT PHARMACEUTICALS INTERNATIONAL
Reel/Frame 026669/0063 →
SECURITY AGREEMENT Recorded Jul 18, 2011
From: VALEANT PHARMACEUTICALS INTERNATIONAL, A DELAWARE CORPORATION; ATON PHARMA, INC., A DELAWARE CORPORATION; CORIA LABORATORIES, LTD., A DELAWARE CORPORATION; DOW PHARMACEUTICAL SCIENCES, INC., A DELAWARE CORPORATION; VALEANT PHARMACEUTICALS NORTH AMERICA LLC, A DELAWARE LLC; PRESTWICK PHARMACEUTICALS, INC., A DELAWARE CORPORATION; VALEANT BIOMEDICALS, INC., A DELAWARE CORPORATION
To: GOLDMAN SACHS LENDING PARTNERS LLC, AS COLLATERAL AGENT
Reel/Frame 026606/0061 →
PATENT SECURITY RELEASE AGREEMENT Recorded Mar 14, 2011
From: GOLDMAN SACHS LENDING PARTNERS LLC
To: VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS NORTH AMERICA; CORIA LABORATORIES, LTD.; DOW PHARMACEUTICAL SCIENCES, INC.; ATON PHARMA, INC.
Reel/Frame 025950/0048 →
SECURITY AGREEMENT Recorded Oct 4, 2010
From: ATON PHARMA, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA; VALEANT PHARMACEUTICALS INTERNATIONAL; CORIA LABORATORIES, LTD.; DOW PHARMACEUTICAL SCIENCES, INC.
To: GOLDMAN SACHS LENDING PARTNERS LLC, AS COLLATERAL AGENT
Reel/Frame 025084/0169 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2008
From: VERNIER, JEAN-MICHEL; SONG, JIANLAN; CHEN, HUANMING; HONG, ZHI
To: VALEANT PHARMACEUTICALS INTERNATIONAL, INC.
Reel/Frame 020760/0563 →