CA2048139A1 - N-sulfonylindoline derivatives, their preparation and the pharmaceutical compositions in which they are present - Google Patents
N-sulfonylindoline derivatives, their preparation and the pharmaceutical compositions in which they are presentInfo
- Publication number
- CA2048139A1 CA2048139A1 CA002048139A CA2048139A CA2048139A1 CA 2048139 A1 CA2048139 A1 CA 2048139A1 CA 002048139 A CA002048139 A CA 002048139A CA 2048139 A CA2048139 A CA 2048139A CA 2048139 A1 CA2048139 A1 CA 2048139A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- alkyl
- naphthyl
- alkoxy
- nitro
- 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
Links
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 abstract 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 abstract 1
- -1 5-dimethylamino-1-naphthyl Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 abstract 1
- 150000001925 cycloalkenes Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
- C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Abstract
N-Sulfonylindoline derivatives of the formula (see formula I) in which - R1 is a halogen atom, a C1-C4 alkyl, a hydroxyl, a C1-C4 alkoxy, a benzyloxy group, a cyano group, a trifluoromethyl group, a nitro group or an amino group;
- R2 is a C1-C6 alkyl, a C3-C7 cycloalkyl, a C5-C7 cycloalkene or a phenyl which is unsubstituted or monosubstituted or polysubstituted by a C1-C4 alkyl, a C1-C4 alkoxy, a halogen, a trifluoromethyl group, a nitro group or an amino group;
- R3 is a hydrogen atom or a C1-C4 alkyl;
- R4 is a carboxyl group, an alkoxycarbonyl group in which the alkyl group is C1-C8, a benzyloxycarbonyl group or a carboxamide group of the formula CONR6R7;
- R5 is a C1-C4 alkyl, a 1-naphthyl, a 2-naphthyl, a 5-dimethylamino-1-naphthyl or a phenyl which is unsub-stituted or substituted by one or more substituents selected from a halogen atom, a C1-C4 alkyl, a tri-fluoromethyl group, a nitro group, an amino group which is free or substituted by one or 2 C1-C4 alkyls, a hydroxyl, a C1-C4 alkoxy, a C1-C4 alkenoxy, a C1-C4 alkylthio, a trifluoromethoxy group, a ben-zyloxy group, a cyano group, a carboxyl group, a C1-C4 alkoxycarbonyl group, a carbamoyl group or a C1-C4 alkylamido group, or, when m = 0, R5 can be a group - R6 and R7 are each independently hydrogen, a C1-C6 alkyl or a phenylalkyl in which the alkyl is C1-C4, or R6 and R7 together form a group -(CH2)p-- n is 0, 1 or 2;
- m is 0, 1 or 2; and - p is 4, 5 or 6;
and their salts, where appropriate.
- R2 is a C1-C6 alkyl, a C3-C7 cycloalkyl, a C5-C7 cycloalkene or a phenyl which is unsubstituted or monosubstituted or polysubstituted by a C1-C4 alkyl, a C1-C4 alkoxy, a halogen, a trifluoromethyl group, a nitro group or an amino group;
- R3 is a hydrogen atom or a C1-C4 alkyl;
- R4 is a carboxyl group, an alkoxycarbonyl group in which the alkyl group is C1-C8, a benzyloxycarbonyl group or a carboxamide group of the formula CONR6R7;
- R5 is a C1-C4 alkyl, a 1-naphthyl, a 2-naphthyl, a 5-dimethylamino-1-naphthyl or a phenyl which is unsub-stituted or substituted by one or more substituents selected from a halogen atom, a C1-C4 alkyl, a tri-fluoromethyl group, a nitro group, an amino group which is free or substituted by one or 2 C1-C4 alkyls, a hydroxyl, a C1-C4 alkoxy, a C1-C4 alkenoxy, a C1-C4 alkylthio, a trifluoromethoxy group, a ben-zyloxy group, a cyano group, a carboxyl group, a C1-C4 alkoxycarbonyl group, a carbamoyl group or a C1-C4 alkylamido group, or, when m = 0, R5 can be a group - R6 and R7 are each independently hydrogen, a C1-C6 alkyl or a phenylalkyl in which the alkyl is C1-C4, or R6 and R7 together form a group -(CH2)p-- n is 0, 1 or 2;
- m is 0, 1 or 2; and - p is 4, 5 or 6;
and their salts, where appropriate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9009778A FR2665441B1 (en) | 1990-07-31 | 1990-07-31 | N-SULFONYL INDOLINE DERIVATIVES, THEIR PREPARATION, THE PHARMACEUTICAL COMPOSITIONS CONTAINING SAME. |
| FR9009778 | 1990-07-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2048139A1 true CA2048139A1 (en) | 1992-02-01 |
| CA2048139C CA2048139C (en) | 2002-02-12 |
Family
ID=9399281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002048139A Expired - Fee Related CA2048139C (en) | 1990-07-31 | 1991-07-30 | N-sulfonylindoline derivatives, their preparation and the pharmaceutical compositions in which they are present |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0469984B1 (en) |
| JP (1) | JP3195381B2 (en) |
| KR (1) | KR100211434B1 (en) |
| AT (1) | ATE129236T1 (en) |
| AU (2) | AU645585B2 (en) |
| CA (1) | CA2048139C (en) |
| DE (1) | DE69113911T2 (en) |
| ES (1) | ES2080922T3 (en) |
| FI (1) | FI97224C (en) |
| FR (1) | FR2665441B1 (en) |
| HU (1) | HU220765B1 (en) |
| IE (1) | IE73452B1 (en) |
| IL (2) | IL99012A (en) |
| NO (1) | NO175254C (en) |
| NZ (1) | NZ239182A (en) |
| PT (1) | PT98476B (en) |
| ZA (1) | ZA916031B (en) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2679903B1 (en) * | 1991-08-02 | 1993-12-03 | Elf Sanofi | DERIVATIVES OF N-SULFONYL INDOLINE CARRYING AN AMIDIC FUNCTION, THEIR PREPARATION, THE PHARMACEUTICAL COMPOSITIONS CONTAINING SAME. |
| US5338755A (en) * | 1990-07-31 | 1994-08-16 | Elf Sanofi | N-sulfonylindoline derivatives, their preparation and the pharmaceutical compositions in which they are present |
| US5481005A (en) * | 1990-07-31 | 1996-01-02 | Sanofi | N-sulfonylindoline derivatives, their preparation and the pharmaceutical compositions in which they are present |
| WO1995002405A1 (en) * | 1993-07-16 | 1995-01-26 | Merck & Co., Inc. | Benzoxazinone and benzopyrimidinone piperidinyl tocolytic oxytocin receptor antagonists |
| WO1995002587A1 (en) * | 1993-07-16 | 1995-01-26 | Merck & Co., Inc. | Substituted piperazinylcamphor derivatives as oxytocin antagonists |
| FR2708608B1 (en) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | N-sulfonylbenzimidazolone derivatives, their preparation, pharmaceutical compositions containing them. |
| FR2708606B1 (en) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | N-phenylalkylindol-2-one derivatives, their preparation, pharmaceutical compositions containing them. |
| FR2714378B1 (en) * | 1993-12-24 | 1996-03-15 | Sanofi Sa | Indol-2-one derivatives substituted in 3 with a nitrogen group, their preparation, pharmaceutical compositions containing them. |
| GB9918684D0 (en) * | 1999-08-09 | 1999-10-13 | Novartis Ag | Organic compounds |
| DE60141849D1 (en) | 2000-10-17 | 2010-05-27 | Merck Serono Sa Coinsins | PHARMACEUTICALLY ACTIVE SULFONAMIDE DERIVATIVES |
| GB0115515D0 (en) * | 2001-06-25 | 2001-08-15 | Ferring Bv | Oxytocin agonisys |
| GB0116594D0 (en) | 2001-07-06 | 2001-08-29 | Cancer Res Ventures Ltd | Therapeutic compounds |
| SI1458381T1 (en) | 2001-12-20 | 2006-04-30 | Applied Research Systems | Triazoles as oxytocin antagonists |
| MXPA04011465A (en) * | 2002-05-24 | 2005-02-14 | Millennium Pharm Inc | Ccr9 inhibitors and methods of use thereof. |
| AU2002353193B2 (en) | 2002-12-20 | 2010-03-25 | Cancer Research Technology Limited | 4-(1-(sulfonyl)-1H-indol-2-yl)-4-(hydroxy)-cyclohexa-2,5-dienone compounds and analogs thereof as therapeutic agents |
| FR2853650B1 (en) * | 2003-04-10 | 2006-07-07 | Merck Sante Sas | AMINE DEDOUBLING PROCESS USEFUL FOR THE TREATMENT OF DISORDERS ASSOCIATED WITH INSULINO-RESISTANCE SYNDROME |
| FR2880023B1 (en) | 2004-12-23 | 2007-02-23 | Sanofi Aventis Sa | N - [(4,5-DIPHENYL-3-ALKYL-2-THIENYL) METHYL] AMINE DERIVATIVES AND THEIR PREPARATION AND THERAPEUTIC USE |
| FR2927625B1 (en) | 2008-02-19 | 2010-03-12 | Sanofi Aventis | NOVEL 3-AMINOALKYL-1,3-DIHYDRO-2H-INDOL-2-ONE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC USE |
| FR2930249B1 (en) | 2008-04-21 | 2010-05-14 | Sanofi Aventis | NOVEL 3-AMINOALKYL-1,3-DIHYDRO-2H-INDOL-2-ONE DERIVATIVES, THEIR PREPARATION AND THERAPEUTIC USE THEREOF |
| WO2025124698A1 (en) | 2023-12-12 | 2025-06-19 | Idorsia Pharmaceuticals Ltd | Aryl sulfone and sulfanone derivatives as orexin receptor modulators |
| WO2025132542A1 (en) | 2023-12-19 | 2025-06-26 | Idorsia Pharmaceuticals Ltd | Macrocyclic orexin agonists |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3838167A (en) * | 1972-08-01 | 1974-09-24 | Lilly Co Eli | Process for preparing indoles |
| US4479963A (en) * | 1981-02-17 | 1984-10-30 | Ciba-Geigy Corporation | 1-Carboxyalkanoylindoline-2-carboxylic acids |
| DE3705934A1 (en) * | 1987-02-25 | 1988-09-08 | Nattermann A & Cie | Indolyl derivatives, processes for their preparation, and their use as medicaments |
| GB8820129D0 (en) * | 1988-08-24 | 1988-09-28 | Schering Agrochemicals Ltd | Fungicides |
| FR2679903B1 (en) * | 1991-08-02 | 1993-12-03 | Elf Sanofi | DERIVATIVES OF N-SULFONYL INDOLINE CARRYING AN AMIDIC FUNCTION, THEIR PREPARATION, THE PHARMACEUTICAL COMPOSITIONS CONTAINING SAME. |
-
1990
- 1990-07-31 FR FR9009778A patent/FR2665441B1/en not_active Expired - Fee Related
-
1991
- 1991-07-29 PT PT98476A patent/PT98476B/en not_active IP Right Cessation
- 1991-07-29 FI FI913614A patent/FI97224C/en not_active IP Right Cessation
- 1991-07-30 CA CA002048139A patent/CA2048139C/en not_active Expired - Fee Related
- 1991-07-30 DE DE69113911T patent/DE69113911T2/en not_active Expired - Fee Related
- 1991-07-30 IL IL9901291A patent/IL99012A/en not_active IP Right Cessation
- 1991-07-30 EP EP91402123A patent/EP0469984B1/en not_active Expired - Lifetime
- 1991-07-30 NO NO912970A patent/NO175254C/en not_active IP Right Cessation
- 1991-07-30 NZ NZ239182A patent/NZ239182A/en unknown
- 1991-07-30 AT AT91402123T patent/ATE129236T1/en not_active IP Right Cessation
- 1991-07-30 ES ES91402123T patent/ES2080922T3/en not_active Expired - Lifetime
- 1991-07-31 IE IE269691A patent/IE73452B1/en not_active IP Right Cessation
- 1991-07-31 AU AU81478/91A patent/AU645585B2/en not_active Ceased
- 1991-07-31 ZA ZA916031A patent/ZA916031B/en unknown
- 1991-07-31 JP JP19207891A patent/JP3195381B2/en not_active Expired - Fee Related
- 1991-07-31 HU HU9102552A patent/HU220765B1/en not_active IP Right Cessation
- 1991-07-31 KR KR1019910013249A patent/KR100211434B1/en not_active Expired - Fee Related
-
1993
- 1993-11-05 AU AU50473/93A patent/AU664491B2/en not_active Ceased
-
1995
- 1995-08-15 IL IL11493495A patent/IL114934A0/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |