FI82687B - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pyridinkarboxylsyraestrar och deras anvaendning som laekemedel. - Google Patents

Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pyridinkarboxylsyraestrar och deras anvaendning som laekemedel. Download PDF

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Publication number
FI82687B
FI82687B FI830810A FI830810A FI82687B FI 82687 B FI82687 B FI 82687B FI 830810 A FI830810 A FI 830810A FI 830810 A FI830810 A FI 830810A FI 82687 B FI82687 B FI 82687B
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FI
Finland
Prior art keywords
pyridine
dimethyl
alkyl
ester
formula
Prior art date
Application number
FI830810A
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English (en)
Finnish (fi)
Other versions
FI830810L (fi
FI830810A0 (fi
FI82687C (sv
Inventor
Egbert Wehinger
Horst Meyer
Ulrich Benz
Original Assignee
Bayer Ag
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Publication date
Application filed by Bayer Ag filed Critical Bayer Ag
Publication of FI830810A0 publication Critical patent/FI830810A0/fi
Publication of FI830810L publication Critical patent/FI830810L/fi
Application granted granted Critical
Publication of FI82687B publication Critical patent/FI82687B/fi
Publication of FI82687C publication Critical patent/FI82687C/sv

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biomedical Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Hospice & Palliative Care (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)
  • Drawers Of Furniture (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Claims (2)

1. Förfarande för framställning av nya terapeu-tiskt användbara pyridinkarboxylsyraestrar med formeln I 5 och farmaceutiskt godtagbara salter därav, R X I COOR3 10 R^N^R2 ' i vilken formel R är fenyl, som kan vara, mono- eller di-15 substltuerad med halogen, cyano, nitro, trifluormetyl, C1.4-alkyl och/eller C^-alkoxi, R1 är C^-alkyl eller hyd-roxi-C1.4-alkyl, R2 är C1.4-alkyl, X är nitril eller COR4, varvid R4 är C1.4-alkyl, eller X är COOR5, varvid R5 är en rakkedjad, förgrenad eller cyklisk alkylradikal med högst 20 12 kolatomer och som 1 kedjan kan innehälla en syreatom, eller X är -S02R6, varvid R6 är C1.4-alkyl eller fenyl, och R3 är olik R5 och betecknar C1.4-alkyl, som kan vara substituerad med hydroxi, cyano, halogen, trifluormetyl-fenoxi, halogenfenoxi, C^-alkoxi eller C2_5-alkanoyloxi 25 och, dä R3 är en substituerad C1.4-alkylgrupp, kan R1 och X tillsammans bilda en 5-7-ledad laktonring, känne-t e c k n a t därav, att A) ett 1,4-dihydropyridinderivat med formeln R
30 I ‘1 x _ __COOR3 i 1 (II) R1--^ N^\_2 H R 35 där R, R1, R2, R3 och X betecknar samma som ovan, omsätts 34 82687 med ett oxiderande (dehydrerande) medel, eventuellt i närvaro av ett inert lösningsmedel vid en temperatur av 0-200°C, eller B) en pyridinkarboxylsyra med formeln
5 R i (III) R1 -^'^N^'^-R2 10 där R, R1, R2 och X betecknar samma som ovan, förestras, eventuellt efter i och för sig känd aktivering av kar-boxylgrupper, eller C) för framställning av föreningar med formeln I, 15 där R1 betecknar hydroxi-C1.4-alkyl, underkastas mot- svarande mono- eller bis-acetoxi-C1.4-alkylpyridin selek-tiv hydrolysbehandling under milda betingelser, eller D) för framställning av föreningar med formeln I, där X är karboxyl och R1 är hydroxi-C1.4-alkyl, hydrolyse- 20 ras i närvaro av alkali en förening med formeln R R509C ^-/Cx^--C02r3 - ^ I \ I ^ " ? jö ji <iv> : 25 H3CCO-C1_4~alkyl ^ ^ \ 2 R där R, R2, R3 och R5 betecknar samma som ovan, eller E) för framställning av föreningar med formeln I, där R1 och X tillsammans bildar en 5-7-ledad laktonring, 30 cykliseras pä i och för sig känt sätt under inverkan av protoner en hydroxialkylpyridinkarboxylsyra med formeln *: R HOOC A. C0oR3 * 35 J (V) HO- (CH„) ^ R2 2. n n 35 82687 där R och R2 betecknar samma som ovan och R3 är substi-tuerad alkyl och n är ett tai 1-3.
2. Förfarande enligt patentkravet 1, k ä n n e -t e c k n a t därav, att man framställer 5,7-dihydro-2-5 metyl-4-(3-nitrofenyl)-5-oxo-furo[3,4-b]pyrldin-3-kar-boxylsyra-(2-hydroxietyl)ester.
FI830810A 1982-03-13 1983-03-10 Förfarande för framställning av nya terapeutiskt användbara pyridinkar boxylsyraestrar och deras användning som läkemedel FI82687C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19823209274 DE3209274A1 (de) 1982-03-13 1982-03-13 Pyridincarbonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE3209274 1982-03-13

Publications (4)

Publication Number Publication Date
FI830810A0 FI830810A0 (fi) 1983-03-10
FI830810L FI830810L (fi) 1983-09-14
FI82687B true FI82687B (fi) 1990-12-31
FI82687C FI82687C (sv) 1991-04-10

Family

ID=6158229

Family Applications (1)

Application Number Title Priority Date Filing Date
FI830810A FI82687C (sv) 1982-03-13 1983-03-10 Förfarande för framställning av nya terapeutiskt användbara pyridinkar boxylsyraestrar och deras användning som läkemedel

Country Status (18)

Country Link
US (1) US4705794A (sv)
EP (1) EP0088940B1 (sv)
JP (1) JPS58167571A (sv)
KR (1) KR910000637B1 (sv)
AT (1) ATE19875T1 (sv)
AU (1) AU564367B2 (sv)
CA (1) CA1208216A (sv)
DE (2) DE3209274A1 (sv)
DK (1) DK157857C (sv)
FI (1) FI82687C (sv)
GR (1) GR78454B (sv)
HU (1) HU188851B (sv)
IE (1) IE54879B1 (sv)
IL (1) IL68095A (sv)
NO (1) NO162234C (sv)
PH (1) PH19685A (sv)
PT (1) PT76328B (sv)
ZA (1) ZA831691B (sv)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58185821U (ja) * 1982-06-02 1983-12-10 日産自動車株式会社 ウインドシ−ルド
DE4342196A1 (de) * 1993-12-10 1995-06-14 Bayer Ag Neue 4-Phenyl-substituierte 1,4-Dihydropyridine
DE3410645A1 (de) * 1984-03-23 1985-09-26 Bayer Ag, 5090 Leverkusen L-alkylsubstituierte 1,4-dihydropyridinlactone, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
GB8530602D0 (en) * 1985-12-12 1986-01-22 Fujisawa Pharmaceutical Co Heterocyclic compounds
IT1204948B (it) * 1987-03-13 1989-03-10 Boheringer Biochemia Robin S P 2-tiometil-sostituite-piridine, metodo per la loro preparazione e composizioni farmaceutiche che le contengono.
DE3712369A1 (de) * 1987-04-11 1988-10-27 Bayer Ag Substituierte 5-nitro-1,4-dihydropyridine, verfahren zur herstellung und ihre verwendung
DE3712371A1 (de) * 1987-04-11 1988-10-27 Bayer Ag Substituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung
US4843085A (en) * 1987-07-01 1989-06-27 Yamanouchi Pharmaceutical Co., Ltd. Pyridine derivatives, process for production thereof and pharmaceutical compositions useful as anti-arhytmics
US5100892A (en) * 1990-11-13 1992-03-31 Glaxo Inc. Dihydropyridine vasodilator agents
EP0657432B1 (de) * 1993-12-10 2003-03-12 Bayer Ag Phenyl-substituierte 1,4-Dihydropyridine mit cerebraler Aktivität
DE4430639A1 (de) 1994-08-29 1996-03-07 Bayer Ag Verwendung von 5-substituierten Pyridin- und Hexahydrochinolin-3-carbonsäurederivaten
AU2004272078A1 (en) * 2003-09-10 2005-03-24 Synta Pharmaceuticals Corp. Dihydropyridine compounds for treating or preventing metabolic disorders

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1552911A (en) * 1975-07-02 1979-09-19 Fujisawa Pharmaceutical Co 1,4 dihydropyridine derivatives and the preparation thereof
NZ201395A (en) * 1981-07-30 1987-02-20 Bayer Ag Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines
DE3209276A1 (de) * 1982-03-13 1983-09-15 Bayer Ag, 5090 Leverkusen Arzneimittel mit antihypoxischer und ischaemie-protektiver wirkung

Also Published As

Publication number Publication date
EP0088940A1 (de) 1983-09-21
FI830810L (fi) 1983-09-14
DE3209274A1 (de) 1983-09-15
KR840004079A (ko) 1984-10-06
FI830810A0 (fi) 1983-03-10
AU1208183A (en) 1983-09-15
PT76328A (en) 1983-04-01
EP0088940B1 (de) 1986-05-21
DE3363581D1 (en) 1986-06-26
NO162234B (no) 1989-08-21
IE54879B1 (en) 1990-03-14
AU564367B2 (en) 1987-08-13
FI82687C (sv) 1991-04-10
ZA831691B (en) 1983-12-28
DK157857C (da) 1990-07-30
HU188851B (en) 1986-05-28
CA1208216A (en) 1986-07-22
GR78454B (sv) 1984-09-27
DK117783D0 (da) 1983-03-11
IE830535L (en) 1983-09-13
US4705794A (en) 1987-11-10
KR910000637B1 (ko) 1991-01-31
PH19685A (en) 1986-06-13
NO830539L (no) 1983-09-14
DK157857B (da) 1990-02-26
IL68095A (en) 1986-12-31
ATE19875T1 (de) 1986-06-15
JPS58167571A (ja) 1983-10-03
NO162234C (no) 1989-11-29
DK117783A (da) 1983-09-14
JPH0551581B2 (sv) 1993-08-03
PT76328B (en) 1985-11-11

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Owner name: BAYER AKTIENGESELLSCHAFT