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FI104069B1 - Process for the preparation of therapeutically useful 3- (phenyl- or cycloalkyl) -3-hydroxy-1-phenylsulfonyl-2-indoline carboxamide derivatives - Google Patents

Process for the preparation of therapeutically useful 3- (phenyl- or cycloalkyl) -3-hydroxy-1-phenylsulfonyl-2-indoline carboxamide derivatives

Info

Publication number
FI104069B1
FI104069B1 FI931476A FI931476A FI104069B1 FI 104069 B1 FI104069 B1 FI 104069B1 FI 931476 A FI931476 A FI 931476A FI 931476 A FI931476 A FI 931476A FI 104069 B1 FI104069 B1 FI 104069B1
Authority
FI
Finland
Prior art keywords
alkyl
mono
substd
halogen
opt
Prior art date
Application number
FI931476A
Other languages
Finnish (fi)
Swedish (sv)
Other versions
FI104069B (en
FI931476A0 (en
FI931476A7 (en
Inventor
Jean Wagnon
Claude Plouzane
Claudine Serradeil-Legal
Dino Nisato
Bernard Tonnerre
Original Assignee
Sanofi Sa
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 Sanofi Sa filed Critical Sanofi Sa
Publication of FI931476A0 publication Critical patent/FI931476A0/en
Publication of FI931476A7 publication Critical patent/FI931476A7/en
Priority to FI980175A priority Critical patent/FI107048B/en
Application granted granted Critical
Publication of FI104069B publication Critical patent/FI104069B/en
Publication of FI104069B1 publication Critical patent/FI104069B1/en

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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
    • 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
    • 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)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • 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

3-Hydroxy-1-indolinyl sulphones of formula (I) and their salts are new: In (I), R1 = halogen, 1-4C alkyl, OH, 1-4C alkoxy, benzyloxy, CN, CF3, NO2 or NH2; R2 = 1-6C alkyl; 3-7C cycloalkyl,; 5-7C cycloalkenyl; phenyl opt. substd. by 1-4C alkyl, 1-4C alkoxy, halogen, CF3 and/or NH2; or nitrophenyl opt. substd. by CF3, 1-4C alkyl or halogen; R5 = 1-4C alkyl; 1- or 2-naphthyl;5-dimethylamino-1-naphthyl; phenyl opt. substd. by halogen, CF3, NH2, mono- or di (1-4C alkyl) amino, OH, 1-4C alkoxy, 2-4C alkenyloxy, 1-4C alkylthio, CF3, benzyloxy, CN, COOH, 2-5C alkoxycarbonyl, CONH2, mono- or di (1-4C alkyl)carbamoyl or 1-4C alkanoylamino; or nitrophenyl opt. substd. by CF3, 2-4C alkenyloxy, halogen, 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio, OCF3 or benzyloxy; R6 = 1-6C alkyl or R7; R7 = 1-R-4-piperidinyl, 1-R-3-azetidinyl or (CH2)rR'; R = H, 1-4C alkyl, benzyloxycarbonyl or 2-5C alkoxycarbonyl; R1 = pyridyl, OH, NH2, mono- or di(1-4C alkyl)amino, COOH, 2-5C alkoxycarbonyl, benzylcarbonyl, CONH2 or mono- or di(1-4C alkyl)carbamoyl; or NR6R7 = morpholino; thiomorpholino; thiazolidinyl or 2,2-dimethylthiazolidinyl opt. substd. by R8; 1-piperazinyl opt. 4-substd. by R"8; and unsatd. 5-membered monoaza ring substd. by R8; or a satd. 3- to 7-membered monoaza ring substd. by R8 and R9; R8 = R'8 or (CH2)rA1, where A1 = OH, NH2 or mono- or di(1-4C alkyl)amino; R'8 = (CH2)qA2, where A2 = COOH, 2-5C alkoxycarbonyl, benzyloxycarbonyl, CONH2, CONHOH, mono- or di(1-4C alkyl)carbamoyl, CSNH2 or mono- or di(1-4C alkyl)thiocarbamoyl; R"8 = R8' or (CH2)A3, where A3 = NH2 or mono- or di(1-4C alkyl)amino; R9 = H, halogen, (CH2rOR10), (CH2)rNR11R12, (CH2)SCONR11R'11 or N3; R10 = H, 1-4C alkyl, mesyl or tosyl; R11, R'11 and R12 = H or 1-4C alkyl, or R11 = H, and R12 = benzyloxycarbonyl or 2-5C alkoxycarbonyl; n and m = 0-2; q = 0-3; r = 0-3, but not 0 when R8 or R9 is in a position alpha to the intracyclic amidic nitrogen (SiC); s = 0 or 1.
FI931476A 1991-08-02 1993-04-01 Process for the preparation of therapeutically useful 3- (phenyl- or cycloalkyl) -3-hydroxy-1-phenylsulfonyl-2-indoline carboxamide derivatives FI104069B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI980175A FI107048B (en) 1991-08-02 1998-01-27 2-sulfonamidofenonderivat

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
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.
FR9109908 1991-08-02
PCT/FR1992/000758 WO1993003013A1 (en) 1991-08-02 1992-07-31 Indoline derivatives having an amide function, their preparation, and pharmaceutical compositions containing them
FR9200758 1992-07-31

Publications (4)

Publication Number Publication Date
FI931476A0 FI931476A0 (en) 1993-04-01
FI931476A7 FI931476A7 (en) 1993-04-01
FI104069B FI104069B (en) 1999-11-15
FI104069B1 true FI104069B1 (en) 1999-11-15

Family

ID=9415909

Family Applications (2)

Application Number Title Priority Date Filing Date
FI931476A FI104069B1 (en) 1991-08-02 1993-04-01 Process for the preparation of therapeutically useful 3- (phenyl- or cycloalkyl) -3-hydroxy-1-phenylsulfonyl-2-indoline carboxamide derivatives
FI980175A FI107048B (en) 1991-08-02 1998-01-27 2-sulfonamidofenonderivat

Family Applications After (1)

Application Number Title Priority Date Filing Date
FI980175A FI107048B (en) 1991-08-02 1998-01-27 2-sulfonamidofenonderivat

Country Status (28)

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)
HU (2) HUT68927A (en)
IL (3) IL117592A (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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Also Published As

Publication number Publication date
ZA925781B (en) 1993-03-02
WO1993003013A1 (en) 1993-02-18
NO931262L (en) 1993-05-26
IL102703A (en) 1997-03-18
CZ68293A3 (en) 1994-01-19
UA27238C2 (en) 2000-08-15
FI104069B (en) 1999-11-15
MY110517A (en) 1998-07-31
EP0526348B1 (en) 1998-02-18
LV10091B (en) 1995-04-20
DE69224450D1 (en) 1998-03-26
FI931476A0 (en) 1993-04-01
FI980175A0 (en) 1998-01-27
AU691223B2 (en) 1998-05-14
ES2117038T3 (en) 1998-08-01
LTIP114A (en) 1994-06-15
LV10091A (en) 1994-05-10
NO180047C (en) 1997-02-05
FI107048B (en) 2001-05-31
CA2206776C (en) 2002-02-26
KR100241583B1 (en) 2000-03-02
CA2206776A1 (en) 1993-02-03
FR2679903B1 (en) 1993-12-03
PH30661A (en) 1997-09-16
ATE163289T1 (en) 1998-03-15
DK0526348T3 (en) 1998-11-23
NO931262D0 (en) 1993-04-01
SK283463B6 (en) 2003-08-05
NO180047B (en) 1996-10-28
AU2475892A (en) 1993-03-02
FR2679903A1 (en) 1993-02-05
SG47501A1 (en) 1998-04-17
IL117592A (en) 1999-04-11
SK42693A3 (en) 1993-10-06
BR9205336A (en) 1993-11-16
CA2093221C (en) 1998-09-22
FI980175L (en) 1998-01-27
IL102703A0 (en) 1993-01-14
DE69224450T2 (en) 1998-07-30
JP2633085B2 (en) 1997-07-23
RU2104268C1 (en) 1998-02-10
LT3064B (en) 1994-10-25
HU9300951D0 (en) 1993-06-28
MX9204487A (en) 1993-02-01
CZ288173B6 (en) 2001-05-16
EP0526348A1 (en) 1993-02-03
HK1008741A1 (en) 1999-05-14
IL117592A0 (en) 1996-07-23
JPH06501960A (en) 1994-03-03
FI931476A7 (en) 1993-04-01
HUT68927A (en) 1995-08-28
AU1154195A (en) 1995-05-04
CA2093221A1 (en) 1993-02-03
NZ243795A (en) 1995-04-27
HU211884A9 (en) 1995-12-28
AU658664B2 (en) 1995-04-27

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