CA2206776A1 - N-sulfonylindoline derivatives carrying an amide functional group, their preparation and the pharmaceutical compositions in which they are present - Google Patents
N-sulfonylindoline derivatives carrying an amide functional group, their preparation and the pharmaceutical compositions in which they are presentInfo
- Publication number
- CA2206776A1 CA2206776A1 CA002206776A CA2206776A CA2206776A1 CA 2206776 A1 CA2206776 A1 CA 2206776A1 CA 002206776 A CA002206776 A CA 002206776A CA 2206776 A CA2206776 A CA 2206776A CA 2206776 A1 CA2206776 A1 CA 2206776A1
- Authority
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- Canada
- Prior art keywords
- group
- substituted
- alkyl
- alkyls
- free
- 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
- 125000003368 amide group Chemical group 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 17
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 5
- -1 5-dimethylamino-1-naphthyl Chemical group 0.000 abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 125000003277 amino group Chemical group 0.000 abstract 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 abstract 1
- 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
- SNPQRYOQWLOTFA-UHFFFAOYSA-N 2,2-dimethyl-1,3-thiazolidine Chemical compound CC1(C)NCCS1 SNPQRYOQWLOTFA-UHFFFAOYSA-N 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
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- 210000000748 cardiovascular system Anatomy 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000001925 cycloalkenes Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000002496 gastric effect Effects 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
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- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/12—Antihypertensives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Compounds of formula (6):
6 in which A' is NR6R7;
- R1 is a halogen atom, a C1-C4 alkyl, a hydroxyl, a C1-C4 alkoxy, a benzyloxy group, a cyano group, a trifluoromethyl group, 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 or an amino group, or R2 is a nitrophenyl which is unsubstituted or monosubstituted by a trifluoromethyl group or monosubstituted or polysubstituted by a C1-C4 alkyl, a C1-C4 alkoxy or a halogen;
- R5 is a C1-C4 alkyl; a 1-naphthyl; a 2-naphthyl; a 5-dimethylamino-1-naphthyl; a phenyl which is unsubstituted or substituted by one or more substituents selected from a halogen atom, a C1-C4 alkyl, a trifluoromethyl group, an amino group which is free or substituted by one or two C1-C4 alkyls, a hydroxyl, a C1-C4 alkoxy, a C2-C4 alkenoxy, a C1-C4 alkylthio, a trifluoromethoxy group, a benzyloxy group, a cyano group, a carboxyl group, a C1-C4 alkoxycarbonyl group, a carbamoyl group which is free or substituted by one or two C1-C4 alkyls or a C1-C4 alkylamido group, or R5 is a nitrophenyl which is unsubstituted or monosubstituted by a trifluoromethyl group or a C2-C4 alkenoxy or mono- or polysubstituted by a halogen, a C1-C4 alkyl, a C1-C4 alkoxy, a C1-C4 alkylthio, a trifluoromethoxy group or a benzyloxy group;
- R6 is a C1-C6 alkyl or R6 is identical to R7;
- R7 is a 4-piperidyl group or a 3-azetidinyl group, the said groups being substituted or unsubstituted on the nitrogen by a C1-C4 alkyl, by a benzyloxycarbonyl or by a C1-C4 alkoxycarbonyl; a group (CH2)r which is itself substituted by a 2-, 3- or 4-pyridyl group, by a hydroxyl group or by an amino group which is free or substituted by one or two C1-C4 alkyls, a carboxyl group, a C1-C4 alkoxycarbonyl group, a benzyloxycarbonyl group or a carbamoyl group which is free or substituted by one or two C1-C4 alkyls;
- or R6 and R7 together, with the nitrogen atom to which they are connected, form a heterocycle selected from:
. morpholine, . thiomorpholine, . thiazolidine or 2,2-dimethylthiazolidine, unsubstituted or substituted by R8, . piperazine, unsubstituted or substituted at the 4-position by a group R"8, . an unsaturated, a 5-membered ring containing a single nitrogen atom and substituted by R8 or a saturated, 3-, 4-, 5-, 6- or 7-membered ring containing a single nitrogen atom and substituted by R8 and R9;
- R8 is R'8 or a group (CH2)r which is itself substituted by a hydroxyl or by an amino which is free or substituted by one or two C1-C4 alkyls;
- R'8 is a group (CH2)q which is itself substituted by a carboxyl group, a C1-C4 alkoxycarbonyl group, a benzyloxycarbonyl group, a carbamoyl group which is free or substituted by a hydroxyl or by one or two C1-C4 alkyls or an aminocarbothioyl group which is free or substituted by one or two C1-C4 alkyls;
- R"8 is R'8 or a group (CH2)2NH2 which is free or substituted by one or two C1-C4 alkyls;
- R9 is hydrogen, a halogen, a group (CH2) rOR10, a group (CH2)rNR11R12, a group (CH2)sCONR11R'11 or an azido group;
- R10 is hydrogen, a C1-C4 alkyl, a mesyl or a tosyl;
- R11, R'11 and R12 are each a hydrogen or a C1-C4 alkyl or R11 is hydrogen and R12 is a benzyloxycarbonyl or a C1-C4 alkoxycarbonyl;
- n is 0, 1 or 2;
- m is 0, 1 or 2;
- q is 0, 1, 2 or 3;
- r is 0, 1, 2 or 3, with the limitation that r is not zero when R8 or R9 is at the alpha-position of the intracyclic amide nitrogen;
- s is 0 or 1;
are useful as intermediates of the preparation of N-sulfonylindoline derivatives which are useful in the treatment of complaints of the central nervous system, the cardiovascular system and the gastric sphere in humans and animals.
6 in which A' is NR6R7;
- R1 is a halogen atom, a C1-C4 alkyl, a hydroxyl, a C1-C4 alkoxy, a benzyloxy group, a cyano group, a trifluoromethyl group, 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 or an amino group, or R2 is a nitrophenyl which is unsubstituted or monosubstituted by a trifluoromethyl group or monosubstituted or polysubstituted by a C1-C4 alkyl, a C1-C4 alkoxy or a halogen;
- R5 is a C1-C4 alkyl; a 1-naphthyl; a 2-naphthyl; a 5-dimethylamino-1-naphthyl; a phenyl which is unsubstituted or substituted by one or more substituents selected from a halogen atom, a C1-C4 alkyl, a trifluoromethyl group, an amino group which is free or substituted by one or two C1-C4 alkyls, a hydroxyl, a C1-C4 alkoxy, a C2-C4 alkenoxy, a C1-C4 alkylthio, a trifluoromethoxy group, a benzyloxy group, a cyano group, a carboxyl group, a C1-C4 alkoxycarbonyl group, a carbamoyl group which is free or substituted by one or two C1-C4 alkyls or a C1-C4 alkylamido group, or R5 is a nitrophenyl which is unsubstituted or monosubstituted by a trifluoromethyl group or a C2-C4 alkenoxy or mono- or polysubstituted by a halogen, a C1-C4 alkyl, a C1-C4 alkoxy, a C1-C4 alkylthio, a trifluoromethoxy group or a benzyloxy group;
- R6 is a C1-C6 alkyl or R6 is identical to R7;
- R7 is a 4-piperidyl group or a 3-azetidinyl group, the said groups being substituted or unsubstituted on the nitrogen by a C1-C4 alkyl, by a benzyloxycarbonyl or by a C1-C4 alkoxycarbonyl; a group (CH2)r which is itself substituted by a 2-, 3- or 4-pyridyl group, by a hydroxyl group or by an amino group which is free or substituted by one or two C1-C4 alkyls, a carboxyl group, a C1-C4 alkoxycarbonyl group, a benzyloxycarbonyl group or a carbamoyl group which is free or substituted by one or two C1-C4 alkyls;
- or R6 and R7 together, with the nitrogen atom to which they are connected, form a heterocycle selected from:
. morpholine, . thiomorpholine, . thiazolidine or 2,2-dimethylthiazolidine, unsubstituted or substituted by R8, . piperazine, unsubstituted or substituted at the 4-position by a group R"8, . an unsaturated, a 5-membered ring containing a single nitrogen atom and substituted by R8 or a saturated, 3-, 4-, 5-, 6- or 7-membered ring containing a single nitrogen atom and substituted by R8 and R9;
- R8 is R'8 or a group (CH2)r which is itself substituted by a hydroxyl or by an amino which is free or substituted by one or two C1-C4 alkyls;
- R'8 is a group (CH2)q which is itself substituted by a carboxyl group, a C1-C4 alkoxycarbonyl group, a benzyloxycarbonyl group, a carbamoyl group which is free or substituted by a hydroxyl or by one or two C1-C4 alkyls or an aminocarbothioyl group which is free or substituted by one or two C1-C4 alkyls;
- R"8 is R'8 or a group (CH2)2NH2 which is free or substituted by one or two C1-C4 alkyls;
- R9 is hydrogen, a halogen, a group (CH2) rOR10, a group (CH2)rNR11R12, a group (CH2)sCONR11R'11 or an azido group;
- R10 is hydrogen, a C1-C4 alkyl, a mesyl or a tosyl;
- R11, R'11 and R12 are each a hydrogen or a C1-C4 alkyl or R11 is hydrogen and R12 is a benzyloxycarbonyl or a C1-C4 alkoxycarbonyl;
- n is 0, 1 or 2;
- m is 0, 1 or 2;
- q is 0, 1, 2 or 3;
- r is 0, 1, 2 or 3, with the limitation that r is not zero when R8 or R9 is at the alpha-position of the intracyclic amide nitrogen;
- s is 0 or 1;
are useful as intermediates of the preparation of N-sulfonylindoline derivatives which are useful in the treatment of complaints of the central nervous system, the cardiovascular system and the gastric sphere in humans and animals.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9109908 | 1991-08-02 | ||
| FR9109908A FR2679903B1 (en) | 1991-08-02 | 1991-08-02 | DERIVATIVES OF N-SULFONYL INDOLINE CARRYING AN AMIDIC FUNCTION, THEIR PREPARATION, THE PHARMACEUTICAL COMPOSITIONS CONTAINING SAME. |
| CA002093221A CA2093221C (en) | 1991-08-02 | 1992-07-31 | N-sulfonylindoline derivatives carrying an amide functional group, their preparation, and the pharmaceutical compositions in which they are present |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002093221A Division CA2093221C (en) | 1991-08-02 | 1992-07-31 | N-sulfonylindoline derivatives carrying an amide functional group, their preparation, and the pharmaceutical compositions in which they are present |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2206776A1 true CA2206776A1 (en) | 1993-02-03 |
| CA2206776C CA2206776C (en) | 2002-02-26 |
Family
ID=9415909
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002093221A Expired - Fee Related CA2093221C (en) | 1991-08-02 | 1992-07-31 | N-sulfonylindoline derivatives carrying an amide functional group, their preparation, and the pharmaceutical compositions in which they are present |
| CA002206776A Expired - Fee Related CA2206776C (en) | 1991-08-02 | 1992-07-31 | N-sulfonylindoline derivatives carrying an amide functional group, their preparation and the pharmaceutical compositions in which they are present |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002093221A Expired - Fee Related CA2093221C (en) | 1991-08-02 | 1992-07-31 | N-sulfonylindoline derivatives carrying an amide functional group, their preparation, and the pharmaceutical compositions in which they are present |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP0526348B1 (en) |
| JP (1) | JP2633085B2 (en) |
| KR (1) | KR100241583B1 (en) |
| AT (1) | ATE163289T1 (en) |
| AU (2) | AU658664B2 (en) |
| BR (1) | BR9205336A (en) |
| CA (2) | CA2093221C (en) |
| CZ (1) | CZ288173B6 (en) |
| DE (1) | DE69224450T2 (en) |
| DK (1) | DK0526348T3 (en) |
| ES (1) | ES2117038T3 (en) |
| FI (2) | FI104069B1 (en) |
| FR (1) | FR2679903B1 (en) |
| HK (1) | HK1008741A1 (en) |
| HU (2) | HUT68927A (en) |
| IL (3) | IL102703A (en) |
| LT (1) | LT3064B (en) |
| LV (1) | LV10091B (en) |
| MX (1) | MX9204487A (en) |
| MY (1) | MY110517A (en) |
| NO (1) | NO180047C (en) |
| NZ (1) | NZ243795A (en) |
| PH (1) | PH30661A (en) |
| RU (1) | RU2104268C1 (en) |
| SG (1) | SG47501A1 (en) |
| SK (1) | SK283463B6 (en) |
| UA (1) | UA27238C2 (en) |
| WO (1) | WO1993003013A1 (en) |
| ZA (1) | ZA925781B (en) |
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| FR2665441B1 (en) * | 1990-07-31 | 1992-12-04 | Sanofi Sa | N-SULFONYL INDOLINE DERIVATIVES, THEIR PREPARATION, THE PHARMACEUTICAL COMPOSITIONS CONTAINING SAME. |
| FR2708608B1 (en) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | N-sulfonylbenzimidazolone derivatives, their preparation, pharmaceutical compositions containing them. |
| FR2756736B1 (en) * | 1996-12-05 | 1999-03-05 | Sanofi Sa | PHARMACEUTICAL COMPOSITIONS CONTAINING N-SULFONYL INDOLINE DERIVATIVES |
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| US6291453B1 (en) | 1997-07-31 | 2001-09-18 | Athena Neurosciences, Inc. | 4-amino-phenylalanine type compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| US6489300B1 (en) | 1997-07-31 | 2002-12-03 | Eugene D. Thorsett | Carbamyloxy compounds which inhibit leukocyte adhesion mediated by VLA-4 |
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| US6559127B1 (en) | 1997-07-31 | 2003-05-06 | Athena Neurosciences, Inc. | Compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| US6362341B1 (en) | 1997-07-31 | 2002-03-26 | Athena Neurosciences, Inc. | Benzyl compounds which inhibit leukocyte adhesion mediated by VLA-4 |
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| US6492421B1 (en) | 1997-07-31 | 2002-12-10 | Athena Neurosciences, Inc. | Substituted phenylalanine type compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| US6583139B1 (en) | 1997-07-31 | 2003-06-24 | Eugene D. Thorsett | Compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| FR2775598A1 (en) * | 1998-03-06 | 1999-09-10 | Sanofi Sa | PHARMACEUTICAL COMPOSITIONS COMPRISING A SELECTIVE ANTAGONIST OF ARGININE-VASOPRESSIN V1A RECEPTORS AND A SELECTIVE ANTAGONIST OF ARGININE-VASOPRESSIN V2 RECEPTORS |
| FR2778103A1 (en) * | 1998-04-29 | 1999-11-05 | Sanofi Sa | PHARMACEUTICAL COMPOSITIONS CONTAINING IN ASSOCIATION A V1A ARGININE-VASOPRESSIN ANTAGONIST AND AN ANGIOTENSIN II AT1 RECEPTOR ANTAGONIST |
| FR2786486B3 (en) * | 1998-11-16 | 2000-12-08 | Sanofi Sa | PROCESS FOR THE PREPARATION OF (2S) -1 - [(2R, 3S) -5-CHLORO-3- (2- CHLOROPHENYL) -1- (3,4-DIMETHOXY BENZENESULFONYL) -3-HYDROXY- 2,3-DIHYDRO- 1H-INDOLE-2-CARBONYL] PYRROLIDINE-2-CARBOXAMIDE, ITS SOLVATES AND / OR HYDRATES |
| PL350050A1 (en) | 1999-01-22 | 2002-10-21 | Elan Pharm Inc | Acyl derivatives which treat vla-4 related disorders |
| TW593284B (en) | 1999-01-22 | 2004-06-21 | Elan Pharm Inc | Fused ring heteroaryl and heterocyclic compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| US6436904B1 (en) | 1999-01-25 | 2002-08-20 | Elan Pharmaceuticals, Inc. | Compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| JP2002539080A (en) * | 1999-01-25 | 2002-11-19 | エラン ファーマシューティカルズ，インコーポレイテッド | Compounds that inhibit leukocyte adhesion mediated by VLA-4 |
| US6407066B1 (en) | 1999-01-26 | 2002-06-18 | Elan Pharmaceuticals, Inc. | Pyroglutamic acid derivatives and related compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| FR2792834A1 (en) * | 1999-04-29 | 2000-11-03 | Sanofi Sa | USE OF SR 49059, ITS PHARMACEUTICALLY ACCEPTABLE SOLVATES AND / OR HYDATES FOR THE PREPARATION OF MEDICINES USEFUL IN THE TREATMENT OR PREVENTION OF RAYNAUD PHENOMENON |
| FR2805536B1 (en) | 2000-02-25 | 2002-08-23 | Sanofi Synthelabo | NOVEL 1,3-DIHYDRO-2H-INDOL-2-ONE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| FR2805992A1 (en) * | 2000-03-08 | 2001-09-14 | Sanofi Synthelabo | Oral administration of N-sulfonyl-indoline derivative to treat central nervous system, cardiovascular or gastric disorders, using polyethylene glycol, polysorbate and poloxamer as solubilizers for high bioavailability |
| US7312358B2 (en) | 2000-10-17 | 2007-12-25 | Laboratoires Serono Sa | Pharmaceutically active sulfanilide derivatives |
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| JP4044740B2 (en) * | 2001-05-31 | 2008-02-06 | 信越化学工業株式会社 | Resist material and pattern forming method |
| IL162615A0 (en) | 2001-12-20 | 2005-11-20 | Applied Research Systems | Triazole derivatives, their preparation and pharmaceutical compositions containing them |
| TWI281470B (en) | 2002-05-24 | 2007-05-21 | Elan Pharm Inc | Heterocyclic compounds which inhibit leukocyte adhesion mediated by alpha4 integrins |
| TW200307671A (en) | 2002-05-24 | 2003-12-16 | Elan Pharm Inc | Heteroaryl compounds which inhibit leukocyte adhesion mediated by α 4 integrins |
| US7238717B2 (en) | 2002-05-24 | 2007-07-03 | Millennium Pharmaceuticals, Inc. | CCR9 inhibitors and methods of use thereof |
| DE60335891D1 (en) * | 2002-10-11 | 2011-03-10 | Actelion Pharmaceuticals Ltd | SULPHONYLAMINE ACID DERIVATIVES AND THEIR USE AS OREXIN RECEPTOR ANTAGONIST |
| US7420055B2 (en) | 2002-11-18 | 2008-09-02 | Chemocentryx, Inc. | Aryl sulfonamides |
| DK1562940T3 (en) | 2002-11-18 | 2007-10-01 | Chemocentryx Inc | arylsulfonamides |
| US7227035B2 (en) | 2002-11-18 | 2007-06-05 | Chemocentryx | Bis-aryl sulfonamides |
| US7741519B2 (en) | 2007-04-23 | 2010-06-22 | Chemocentryx, Inc. | Bis-aryl sulfonamides |
| EP1940826B1 (en) | 2005-09-29 | 2010-12-29 | Elan Pharmaceuticals Inc. | Pyrimidinyl amide compounds which inhibit leukocyte adhesion mediated by vla-4 |
| CA2851103A1 (en) | 2005-09-29 | 2007-04-12 | Elan Pharmaceuticals, Inc. | Carbamate compounds which inhibit leukocyte adhesion mediated by vla-4 |
| NZ570679A (en) | 2006-02-27 | 2011-01-28 | Elan Pharm Inc | Pyrimidinyl sulfonamide compounds which inhibit leukocyte adhesion mediated By VLA-4 |
| MX2011011326A (en) | 2009-04-27 | 2012-02-13 | Elan Pharm Inc | Pyridinone antagonists of alpha-4 integrins. |
| HU231206B1 (en) | 2017-12-15 | 2021-10-28 | Richter Gedeon Nyrt. | Triazolobenzazepines |
| TW201938171A (en) | 2017-12-15 | 2019-10-01 | 匈牙利商羅特格登公司 | Tricyclic compounds as vasopressin V1a receptor antagonists |
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| 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 |
| FR2665441B1 (en) * | 1990-07-31 | 1992-12-04 | Sanofi Sa | N-SULFONYL INDOLINE DERIVATIVES, THEIR PREPARATION, THE PHARMACEUTICAL COMPOSITIONS CONTAINING SAME. |
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1991
- 1991-08-02 FR FR9109908A patent/FR2679903B1/en not_active Expired - Fee Related
-
1992
- 1992-07-31 PH PH44760A patent/PH30661A/en unknown
- 1992-07-31 BR BR9205336A patent/BR9205336A/en not_active Application Discontinuation
- 1992-07-31 IL IL102703A patent/IL102703A/en not_active IP Right Cessation
- 1992-07-31 CA CA002093221A patent/CA2093221C/en not_active Expired - Fee Related
- 1992-07-31 IL IL11759292A patent/IL117592A/en not_active IP Right Cessation
- 1992-07-31 MX MX9204487A patent/MX9204487A/en not_active IP Right Cessation
- 1992-07-31 ZA ZA925781A patent/ZA925781B/en unknown
- 1992-07-31 HU HU9300951A patent/HUT68927A/en unknown
- 1992-07-31 AU AU24758/92A patent/AU658664B2/en not_active Ceased
- 1992-07-31 CA CA002206776A patent/CA2206776C/en not_active Expired - Fee Related
- 1992-07-31 JP JP5503337A patent/JP2633085B2/en not_active Expired - Fee Related
- 1992-07-31 LT LTIP114A patent/LT3064B/en not_active IP Right Cessation
- 1992-07-31 LV LVP-92-87A patent/LV10091B/en unknown
- 1992-07-31 WO PCT/FR1992/000758 patent/WO1993003013A1/en active IP Right Grant
- 1992-07-31 KR KR1019930701034A patent/KR100241583B1/en not_active IP Right Cessation
- 1992-07-31 MY MYPI92001379A patent/MY110517A/en unknown
- 1992-07-31 RU RU93005168A patent/RU2104268C1/en not_active IP Right Cessation
- 1992-07-31 UA UA93002340A patent/UA27238C2/en unknown
- 1992-07-31 NZ NZ243795A patent/NZ243795A/en unknown
- 1992-07-31 CZ CZ1993682A patent/CZ288173B6/en not_active IP Right Cessation
- 1992-07-31 SK SK426-93A patent/SK283463B6/en unknown
- 1992-08-03 DE DE69224450T patent/DE69224450T2/en not_active Expired - Fee Related
- 1992-08-03 SG SG1996002367A patent/SG47501A1/en unknown
- 1992-08-03 EP EP92402213A patent/EP0526348B1/en not_active Expired - Lifetime
- 1992-08-03 AT AT92402213T patent/ATE163289T1/en not_active IP Right Cessation
- 1992-08-03 ES ES92402213T patent/ES2117038T3/en not_active Expired - Lifetime
- 1992-08-03 DK DK92402213T patent/DK0526348T3/en active
-
1993
- 1993-04-01 FI FI931476A patent/FI104069B1/en not_active IP Right Cessation
- 1993-04-01 NO NO931262A patent/NO180047C/en not_active IP Right Cessation
-
1995
- 1995-02-03 AU AU11541/95A patent/AU691223B2/en not_active Ceased
- 1995-06-28 HU HU95P/P00474P patent/HU211884A9/en unknown
-
1996
- 1996-03-21 IL IL11759296A patent/IL117592A0/en unknown
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1998
- 1998-01-27 FI FI980175A patent/FI107048B/en not_active IP Right Cessation
- 1998-07-03 HK HK98108861A patent/HK1008741A1/en not_active IP Right Cessation
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