CA2233975A1 - Succinimide and maleimide cytokine inhibitors - Google Patents

Succinimide and maleimide cytokine inhibitors

Info

Publication number
CA2233975A1
CA2233975A1 CA002233975A CA2233975A CA2233975A1 CA 2233975 A1 CA2233975 A1 CA 2233975A1 CA 002233975 A CA002233975 A CA 002233975A CA 2233975 A CA2233975 A CA 2233975A CA 2233975 A1 CA2233975 A1 CA 2233975A1
Authority
CA
Canada
Prior art keywords
succinimide
cytokine inhibitors
maleimide
inhibitors
novel
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002233975A
Other languages
French (fr)
Other versions
CA2233975C (en
Inventor
George W. Muller
Mary Shire
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Celgene Corp
Original Assignee
Celgene Corporation
George W. Muller
Mary Shire
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Celgene Corporation, George W. Muller, Mary Shire filed Critical Celgene Corporation
Publication of CA2233975A1 publication Critical patent/CA2233975A1/en
Application granted granted Critical
Publication of CA2233975C publication Critical patent/CA2233975C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide

Abstract

Novel succinimides and maleimides are inhibitors or tumor necrosis factor .alpha. and phosphodiesterase and can be used to combat cachexia, endotoxic shock, retrovirus replication, asthma, and inflammatory conditions. A typical embodiment is methyl 3-(3',4',5',6'-tetrahydrophthalimido)-(3",4"-dimethoxyphenyl)propionate. The novel compounds have the following formula:
(see formula I) in which:
R1 is -CH2-, -CH2CO-, or -CO-;
R2, R3, R4 and R5 are more fully described in the disclosure.
CA002233975A 1995-10-06 1996-10-04 Succinimide and maleimide cytokine inhibitors Expired - Fee Related CA2233975C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/539,879 US5658940A (en) 1995-10-06 1995-10-06 Succinimide and maleimide cytokine inhibitors
US08/539,879 1995-10-06
PCT/US1996/015864 WO1997012859A1 (en) 1995-10-06 1996-10-04 Succinimide and maleimide cytokine inhibitors

Publications (2)

Publication Number Publication Date
CA2233975A1 true CA2233975A1 (en) 1997-04-10
CA2233975C CA2233975C (en) 2005-12-06

Family

ID=24153040

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002233975A Expired - Fee Related CA2233975C (en) 1995-10-06 1996-10-04 Succinimide and maleimide cytokine inhibitors

Country Status (19)

Country Link
US (1) US5658940A (en)
EP (1) EP0862552B1 (en)
JP (1) JP3226546B2 (en)
KR (1) KR100345826B1 (en)
AT (1) ATE248145T1 (en)
AU (1) AU723915B2 (en)
CA (1) CA2233975C (en)
CZ (1) CZ105398A3 (en)
DE (1) DE69629716T2 (en)
ES (1) ES2206600T3 (en)
FI (1) FI119690B (en)
HK (1) HK1017885A1 (en)
HU (1) HUP9902034A3 (en)
NZ (1) NZ321001A (en)
PL (1) PL326063A1 (en)
PT (1) PT862552E (en)
RU (1) RU2176242C2 (en)
SK (1) SK44698A3 (en)
WO (1) WO1997012859A1 (en)

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AU2006200033B8 (en) * 1998-10-30 2008-09-11 Celgene Corporation Substituted phenethylsulfones and methods of reducing TNF-alpha levels
US6020358A (en) * 1998-10-30 2000-02-01 Celgene Corporation Substituted phenethylsulfones and method of reducing TNFα levels
US7629360B2 (en) * 1999-05-07 2009-12-08 Celgene Corporation Methods for the treatment of cachexia and graft v. host disease
AU6108300A (en) * 1999-07-15 2001-02-05 Cytoclonal Pharmaceutics, Inc. Method of designing tubulin polymerization stabilizers
US7122666B2 (en) * 1999-07-21 2006-10-17 Sankyo Company, Limited Heteroaryl-substituted pyrrole derivatives, their preparation and their therapeutic uses
US6667316B1 (en) 1999-11-12 2003-12-23 Celgene Corporation Pharmaceutically active isoindoline derivatives
US7182953B2 (en) 1999-12-15 2007-02-27 Celgene Corporation Methods and compositions for the prevention and treatment of atherosclerosis restenosis and related disorders
US6699899B1 (en) 1999-12-21 2004-03-02 Celgene Corporation Substituted acylhydroxamic acids and method of reducing TNFα levels
US6326388B1 (en) 1999-12-21 2001-12-04 Celgene Corporation Substituted 1,3,4-oxadiazoles and a method of reducing TNF-alpha level
US20010051348A1 (en) * 2000-01-28 2001-12-13 Lee Chee Wee Novel ligands and methods for preparing same
US8030343B2 (en) * 2000-06-08 2011-10-04 Celgene Corporation Pharmaceutically active isoindoline derivatives
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US6962940B2 (en) * 2002-03-20 2005-11-08 Celgene Corporation (+)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione: methods of using and compositions thereof
US7893101B2 (en) 2002-03-20 2011-02-22 Celgene Corporation Solid forms comprising (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, compositions thereof, and uses thereof
US7276529B2 (en) * 2002-03-20 2007-10-02 Celgene Corporation Methods of the treatment or prevention of exercise-induced asthma using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione
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CA2481385A1 (en) * 2002-04-12 2003-10-23 Celgene Corporation Modulation of stem and progenitor cell differentiation, assays, and uses thereof
US20100129363A1 (en) * 2002-05-17 2010-05-27 Zeldis Jerome B Methods and compositions using pde4 inhibitors for the treatment and management of cancers
CA2486141A1 (en) 2002-05-17 2003-11-27 Celgene Corporation Methods and compositions using selective cytokine inhibitory drugs for treatment and management of cancers and other diseases
ES2286491T3 (en) * 2002-08-10 2007-12-01 Nycomed Gmbh PIPERIDINA-FTALAZONAS REPLACED WITH PIRROLIDINADIONA, AS INHIBITING AGENTS OF THE PDE4.
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US20040087558A1 (en) * 2002-10-24 2004-05-06 Zeldis Jerome B. Methods of using and compositions comprising selective cytokine inhibitory drugs for treatment, modification and management of pain
US7776907B2 (en) * 2002-10-31 2010-08-17 Celgene Corporation Methods for the treatment and management of macular degeneration using cyclopropyl-N-{2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-3-oxoisoindoline-4-yl}carboxamide
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Also Published As

Publication number Publication date
SK44698A3 (en) 1998-09-09
PL326063A1 (en) 1998-08-17
WO1997012859A1 (en) 1997-04-10
ES2206600T3 (en) 2004-05-16
AU7387396A (en) 1997-04-28
DE69629716D1 (en) 2003-10-02
US5658940A (en) 1997-08-19
KR19990064052A (en) 1999-07-26
ATE248145T1 (en) 2003-09-15
CA2233975C (en) 2005-12-06
DE69629716T2 (en) 2004-07-08
JPH11513387A (en) 1999-11-16
HUP9902034A2 (en) 1999-11-29
HUP9902034A3 (en) 2001-01-29
CZ105398A3 (en) 1998-07-15
NZ321001A (en) 2001-03-30
PT862552E (en) 2003-12-31
EP0862552A1 (en) 1998-09-09
KR100345826B1 (en) 2002-11-18
HK1017885A1 (en) 1999-12-03
EP0862552B1 (en) 2003-08-27
JP3226546B2 (en) 2001-11-05
RU2176242C2 (en) 2001-11-27
FI119690B (en) 2009-02-13
FI980776A0 (en) 1998-04-03
FI980776A (en) 1998-06-05
AU723915B2 (en) 2000-09-07

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