IP Library › Granted Patent US 6,989,451
Granted Patent B2
US 6,989,451 · App. 10/455,149 · Granted Jan 24, 2006

Heterocyclic compounds and uses thereof

Assignee: Valeant Research & Development
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Quick Facts
Patent No.
US 6,989,451
App. No.
10/455,149
Granted
Jan 24, 2006
Kind
B2
Abstract

Substituted isothiazole compounds and compositions are provided, wherein particularly preferred compositions and methods are directed towards inhibition of various protein kinases (especially MEK and/or ERK). Consequently, particularly preferred methods include treatment of diseases associated with abnormality in MEK and/or ERK function.

Claims (32)

1. A compound selected from the group consisting of the following, or a salt thereof:

5-(3-methylphenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-methoxyphenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2-methoxyphenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3-methoxyphenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-nitrophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(1-naphthyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-phenyl-2-methoxyphenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2,6-di-isopropylphenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2-dimethylamino-1-naphthyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-dimethylamino-1-naphthyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2-trichloromethyl-phenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-aminophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-acetyl-phenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-methoxycarbonyl-phenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2-fluorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2-methoxycarbonyl-phenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(2,4-dichlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(1-indanyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(pyridin-3-yl)amino-3-hydroxy-4-cyano-isothiazole;

5-(4-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3-trichloromethyl-4-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3,5-dichlorophenyl)amino-3-hydroxy-4-cyano-isothiazole; and

5-(4-bromophenyl)amino-3-hydroxy-4-cyano-isothiazole.

2. A compound selected from the group consisting of the following, or a salt thereof:

5-(4-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3-trichloromethyl-4-chlorophenyl)amino-3-hydroxy-4-cyano-isothiazole;

5-(3,5-dichlorophenyl)amino-3-hydroxy-4-cyano-isothiazole; and

5-(4-bromophenyl)amino-3-hydroxy-4-cyano-isothiazole.

Assignments (12)
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 HEALTH IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMA POLAND SPOLKA Z ORGANICZONA ODPOWIEDZIALNOSCIA; VALEANT SP. Z.O.O.
Reel/Frame 073637/0222 →
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 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jul 3, 2019
From: BAUSCH HEALTH IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT PHARMACEUTICALS LUXEMBOURG S.À R.L.; VALEANT PHARMA POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA; VALEANT SP. Z O. O.
To: THE BANK OF NEW YORK MELLON, AS COLLATERAL AGENT
Reel/Frame 049672/0652 →
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 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 →
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 →
CHANGE OF NAME Recorded Aug 31, 2005
From: RIBAPHARM INC.
To: VALEANT RESEARCH & DEVELOPMENT
Reel/Frame 016475/0704 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 6, 2004
From: RICKETTS, WILLIAM; AN, HAOYUN; ZHANG, WEIJIAN; HONG, ZHI
To: RIBAPHARM INC.
Reel/Frame 014955/0297 →
Continuity (2)
Provisional Application 6038617500 · Jun 4, 2002
Related Publication 20040039037A1 · Feb 26, 2004