FI106378B - Förfarande för framställning av terapeutiskt användbara 3-substituerade 2-oxoindolderivat - Google Patents

Förfarande för framställning av terapeutiskt användbara 3-substituerade 2-oxoindolderivat Download PDF

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Publication number
FI106378B
FI106378B FI901915A FI901915A FI106378B FI 106378 B FI106378 B FI 106378B FI 901915 A FI901915 A FI 901915A FI 901915 A FI901915 A FI 901915A FI 106378 B FI106378 B FI 106378B
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mmol
formula
acid
solid
alkyl
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FI901915A
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Finnish (fi)
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FI901915A0 (fi
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Carl Joseph Goddard
Gary Richard Schulte
Frederick Jacob Ehrgott
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Pfizer
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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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • C07D209/32—Oxygen atoms
    • C07D209/34—Oxygen atoms in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—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
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/14—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 three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Neurosurgery (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Cardiology (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Claims (8)

1. Förfarande för framställning av terapeutiskt användbara 3-substituerade 2-oxoindolderivat med formeln I 5 (CR2)n-Q 10 j k2 samt farmaceutiskt godtagbara salter därav, i vilken forme 1
15 X är H, F, Cl, Br, (C^Cg) alkyl eller CF3; Y är H, F, Cl, Br, (Cj^-Cg) alkyl eller CF3; R1 är H; R2 är CONR7R8; Q är 20 ^^A eller Q2-A1; A är H, F, Cl, Br, I, CF3, OR9, S(0)pRl°, COOR11, ·, 2 5 CONR9R11, COR10, CHjOR11, OCOR10, NR^11, S02NR9R11, 12 ellsr ' 30 : B är H, F, Cl, Br, I eller CF3; under förutsättning att bade A och B inte är H, eller A och B är tillsammans bundna till samma ringkol i Q1 och bildar oxogruppen, eller när A inte är H, da betecknar 35 B samma som ovan definierats eller är (C1-C4) alkyl; 106378 A1 är F, Cl, Br, I, CF3, OR9, S(0)pR10, COOR11, CONR9R11, COR10, CHjOR11, OCOR10, NR9RX1 eller S02NR9R11 ; Q1 är O O O 10 n—w r^N>N O O Q2 är 15 /N^N /N N --. - < i . O , M \^w \w/ eller N\ y ' Nw 20 bäde n och p är 0, 1 eller 2; bäde W och Z är O eller S; var och en av R7, R8, R9 och R11 är H eller (Ci-Ce) alkyl; R10 är (Cj^-Cg) alkyl; och ·. 25 R12 är H, F, Cl, Br, CF3 eller (Cj-Cg) alkyl; kännetecknat därav att man upplöser en förening med formeln III Q- (CH2) nCOCl (III) 30 I väri Q och n betecknar samraa som ovan, i ett reaktions- inert lösningsmedel och blandar längsamt in i en lösning som innehäller ungefär en ekvimolär mängd av en förening med formeln IV 35 X 76 106378 7“5<N-, UAA väri X, Y och R2 betecknar samma sora ovan, och ett molärt överskott av ett basiskt medel i ett reaktionsinert lös-ningsmedel vid en temperatur cirka 0 °C; läter reaktions-10 blandningen att uppvärma tili en temperatur cirka 25 °C; och gör reaktionsblandningen surt, varvid erhälls en före-ning raed formeln I; och eventuellt överför den erhällna föreningen med for-meln I pä i och för sig kännt sätt tili ett farmaceutiskt 15 godtagbart sait.
2. Förfarande enligt patentkrav 1, k ä n n e -t e c k n a t därav, att Q1 2 är I-V N-W /N\. O · o och Q3 4 5 6 är / ' f eller J' \ 25 \w/. Förfarande enligt patentkrav 1 eller 2, k ä n - 2 netecknat därav, att bade X och Y är H, F, Cl,
3 (Ci-C3) alkyl eller CF3.
4 30 4. Förfarande enligt nägot av patentkraven 1-3, 5 ‘ kännetecknat därav, att A är H, F, Cl, Br, CF3, 6 OR7, COR8 eller CH^R9 och B är H, F, Cl, Br eller CF3 el 7 ler A och B är tillsammans bundna tili samma ringkol i Q1 8 och bildar oxogruppen, eller när A inte är H, dä betecknar 35 B samma som ovan definierats eller är (Cx-C3) alkyl; och A1 9 är F. 106378 77
5. Förfarande enligt nägot av patentkraven 1 - 4, kännetecknat därav, att n är 0 eller 1. 1
6. Förfarande enligt patentkrav 5, känne tecknat därav, att n är 0, X är 5-F, Y är 6-Cl och 5 Q är 10
7. Förfarande enligt patentkrav 5, känne tecknat därav, att n är 0, X är 5-Cl, Y är H och Q är
8. Förfarande enligt nägot av patentkraven 1-7, kännetecknat därav, att det reaktionsinerta 20 lösningsmedlet är Ν,Ν-dimetylformamid, N,N-dimetylactamid, N-metylpyrrolidon eller dimetylsulfoxid och det basiska medlet är trimetylamin, trietylamin, tributylamin, N-me-tylmorfolin, N-metylpiperidin, pyridin eller 4-(N,N-dime-tylamino)pyridin. 25 t. «*
FI901915A 1989-04-18 1990-04-17 Förfarande för framställning av terapeutiskt användbara 3-substituerade 2-oxoindolderivat FI106378B (sv)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI954169A FI106459B (sv) 1989-04-18 1995-09-06 Förfarande för framställning av 3-substituerade 2-oxoindolderivat

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US34011389A 1989-04-18 1989-04-18
US34011389 1989-04-18

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FI901915A0 FI901915A0 (fi) 1990-04-17
FI106378B true FI106378B (sv) 2001-01-31

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US (4) US5047554A (sv)
EP (1) EP0393936B1 (sv)
JP (2) JP2506478B2 (sv)
KR (1) KR920006394B1 (sv)
CN (1) CN1022832C (sv)
AP (1) AP142A (sv)
AT (1) ATE118767T1 (sv)
AU (1) AU633767B2 (sv)
BG (1) BG60646B1 (sv)
CA (1) CA2014467C (sv)
CZ (1) CZ284340B6 (sv)
DD (1) DD293822A5 (sv)
DE (1) DE69017066T2 (sv)
DK (1) DK0393936T3 (sv)
EG (1) EG19122A (sv)
ES (1) ES2068334T3 (sv)
FI (1) FI106378B (sv)
GR (1) GR3015811T3 (sv)
HU (2) HUT58314A (sv)
IE (1) IE65091B1 (sv)
IL (3) IL94047A (sv)
IS (1) IS1636B (sv)
MA (1) MA21808A1 (sv)
MX (1) MX20359A (sv)
NO (1) NO176759C (sv)
NZ (1) NZ233320A (sv)
OA (1) OA09205A (sv)
PL (2) PL163941B1 (sv)
PT (1) PT93785B (sv)
RO (1) RO106402B1 (sv)
RU (2) RU2039042C1 (sv)
YU (1) YU47588B (sv)
ZA (1) ZA902871B (sv)

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DD293822A5 (de) 1991-09-12
RU2039042C1 (ru) 1995-07-09
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US5047554A (en) 1991-09-10
NO176759B (no) 1995-02-13
IE901360L (en) 1990-10-18
BG60646B1 (bg) 1995-11-30
AU1051092A (en) 1992-04-09
AU633767B2 (en) 1993-02-04
YU47588B (sh) 1995-10-24
EG19122A (en) 1994-07-30
BG91773A (bg) 1993-12-24
DK0393936T3 (da) 1995-06-26
CZ284340B6 (cs) 1998-10-14
DE69017066T2 (de) 1995-06-14
AU621477B2 (en) 1992-03-12
NZ233320A (en) 1991-09-25
KR900016189A (ko) 1990-11-12
PL284817A1 (en) 1991-03-25
RU2073671C1 (ru) 1997-02-20
JPH07118261A (ja) 1995-05-09
EP0393936A1 (en) 1990-10-24
NO901684L (no) 1990-10-19
NO176759C (no) 1995-05-24
IL110173A0 (en) 1994-10-07
AP142A (en) 1991-09-26
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CA2014467A1 (en) 1990-10-18
PT93785A (pt) 1990-11-20
RO106402B1 (ro) 1993-04-30
AU5362690A (en) 1990-11-22
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IL94047A0 (en) 1991-01-31
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