FI92195B - Förfarande för framställning av terapeutiskt användbara pyridinderivat - Google Patents

Förfarande för framställning av terapeutiskt användbara pyridinderivat Download PDF

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Publication number
FI92195B
FI92195B FI890257A FI890257A FI92195B FI 92195 B FI92195 B FI 92195B FI 890257 A FI890257 A FI 890257A FI 890257 A FI890257 A FI 890257A FI 92195 B FI92195 B FI 92195B
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FI
Finland
Prior art keywords
mmol
alkyl
branched
straight
phenyl
Prior art date
Application number
FI890257A
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English (en)
Finnish (fi)
Other versions
FI92195C (sv
FI890257A (sv
FI890257A0 (sv
Inventor
Rolf Angerbauer
Peter Fey
Walter Huebsch
Thomas Philipps
Hilmar Bischoff
Dieter Petzinna
Delf Schmidt
Guenter Thomas
Original Assignee
Bayer Ag
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
Priority claimed from DE3801440A external-priority patent/DE3801440A1/de
Priority claimed from IT8821587A external-priority patent/IT8821587A0/it
Application filed by Bayer Ag filed Critical Bayer Ag
Publication of FI890257A0 publication Critical patent/FI890257A0/sv
Publication of FI890257A publication Critical patent/FI890257A/sv
Application granted granted Critical
Publication of FI92195B publication Critical patent/FI92195B/sv
Publication of FI92195C publication Critical patent/FI92195C/sv

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/24Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55Acids; Esters
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

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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)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Obesity (AREA)
  • Vascular Medicine (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)

Claims (13)

1. Förfarande för framställning av terapeutiskt användbara pyridinderivat med formeln I 5 1 R1 H H 7. jC I 7 r'00C-HoC-C-HoC-HC-HC=HC—-^n^-CH=CH-CH-CH--C-CHo-C00R 2 I 2 I 7 | 2 I 2 in OH OH , JU Λ „ OH OH 1U R3^VN'^r2 (I) väri R1 Sr väte eller halogen, R2 är C3_6-cykloalkyl eller rakkedjad eller förgrenad C1.6-15 alkyl, R3 är C3_6-cykloalkyl eller rakkedjad eller förgrenad C^j-alkyl, som kan vara substituerad med fenyl, eller fenyl och R7 är väte, rakkedjad eller förgrenad Cj^-alkyl eller en 20 natrium- eller kalciumkatjon, kännetecknat därav, att man reducerar ett keton med den allmänna formeln VIII R1
25 Uj) 0 ? R800C-H2C-C-H2C-HC-HC=HC--rjX<^v—CH=CH-<pH-CH2-C-CH2-COOR8 OH 2 0H R3/^N (VIII) 30 väri R1, R2 och R3 betecknar samma som ovan och R8 är rakkedjad eller förgrenad C1_12-alkyl, vid framställning av syror förtvälar estrarna, vid framställning av salter förtvälar estrarna, och 35 eventuellt separerar isomererna. 66 92,>5
2. Förfarande enligt patentkrav 1, k ä n n e - t e c k n a t därav, att reduceringen utförs vid en tem-peratur av -80 - +30 °C.
3. Keton med formeln VIII
5 R1 Φ y r8ooc-h0c-c-h9c-hc-hc=hc ch=ch-ch-ch2-c-ch2-coor8
2. I I HO oJlJL o 0H
10 R3/^N-^r2 K (VIII) väri R1 är väte eller halogen, R2 är C3.6-cykloalkyl eller rakkedjad eller förgrenad Cj_6-15 alkyl, R3 är C3_6-cykloalkyl eller rakkedjad eller förgrenad C1_6-alkyl, som kan vara substituerad med fenyl, eller fenyl och R8 är rakkedjad eller förgrenad Cj.^-alkyl. 20 4. Förfarande för framställning av keton med for meln VIII R1
0 O
25 R800C-HoC-C-H^C-HC-HC=HC·—CH=CH-CH-CHo-C-CH--C00R8 2 2 | T ^ f | 2 2 H0 , OH (VIII) väri
30 R1 är väte eller halogen, R2 är C3_6-cykloalkyl eller rakkedjad eller förgrenad C1.6-alkyl, R3 är C3_6-cykloalkyl eller rakkedjad eller förgrenad C^-alkyl, som kan vara substituerad med fenyl, eller fenyl 35 och n 921 95 67 R8 är rakkedjad eller förgrenad C1.12-alkyl, kännetecknat därav, att man omsätter en alde-hyd med den allmänna formeln IX
5 R1 0 rii 0 ηΛ\ i (IX) 10 r3/^N^\r2 väri R1, R2 och R3 betecknar samma som ovan, i ett inert lösningsmedel i närvaro av en bas med en acet-15 ättikester med den allmänna formeln X 0 11 8 h3c-c-ch2-coor (X) 20 väri R8 betecknar samma som ovan.
5. Förfarande enligt patentkrav 4, kännetecknat därav, att reaktionen utförs vid en tempe-ratur av -80 - +50 °C. f #
FI890257A 1988-01-20 1989-01-18 Förfarande för framställning av terapeutiskt användbara pyridinderivat FI92195C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE3801440 1988-01-20
DE3801440A DE3801440A1 (de) 1988-01-20 1988-01-20 Disubstituierte pyridine
IT8821587A IT8821587A0 (it) 1988-07-29 1988-07-29 Piridine disostituite.
IT2158788 1988-07-29

Publications (4)

Publication Number Publication Date
FI890257A0 FI890257A0 (sv) 1989-01-18
FI890257A FI890257A (sv) 1989-07-21
FI92195B true FI92195B (sv) 1994-06-30
FI92195C FI92195C (sv) 1994-10-10

Family

ID=25864088

Family Applications (1)

Application Number Title Priority Date Filing Date
FI890257A FI92195C (sv) 1988-01-20 1989-01-18 Förfarande för framställning av terapeutiskt användbara pyridinderivat

Country Status (16)

Country Link
US (1) US4968689A (sv)
EP (1) EP0325129B1 (sv)
JP (1) JP2712107B2 (sv)
KR (1) KR890011847A (sv)
CN (1) CN1034716A (sv)
AT (1) ATE111081T1 (sv)
AU (1) AU614810B2 (sv)
DE (1) DE58908290D1 (sv)
DK (1) DK23289A (sv)
ES (1) ES2058343T3 (sv)
FI (1) FI92195C (sv)
HU (1) HU208691B (sv)
IL (1) IL88971A (sv)
NO (1) NO890046L (sv)
NZ (1) NZ227636A (sv)
PT (1) PT89478B (sv)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3505382A1 (de) * 1985-02-16 1986-08-21 Accord-Landmaschinen Heinrich Weiste & Co Gmbh, 4770 Soest Zweischeibenduengerstreuer
NO177005C (no) * 1988-01-20 1995-07-05 Bayer Ag Analogifremgangsmåte for fremstilling av substituerte pyridiner, samt mellomprodukter til bruk ved fremstillingen
US5506219A (en) * 1988-08-29 1996-04-09 E. R. Squibb & Sons, Inc. Pyridine anchors for HMG-CoA reductase inhibitors
FI94339C (sv) 1989-07-21 1995-08-25 Warner Lambert Co Förfarande för framställning av farmaceutiskt användbar /R-(R*,R*)/-2-(4-fluorfenyl)- , -dihydroxi-5-(1-metyletyl)-3-fenyl-4-/(fenylamino)karbonyl/-1H-pyrrol-1-heptansyra och farmaceutiskt användbara salter därav
DE3925636A1 (de) * 1989-08-03 1991-02-07 Bayer Ag Imino-substituierte pyridine
US5183897A (en) * 1989-08-03 1993-02-02 Bayer Aktiengesellschaft Certain intermediate imino-substituted pyridines
DE3929507A1 (de) * 1989-09-06 1991-03-07 Bayer Ag Substituierte amino-pyridine
PT657432E (pt) * 1993-12-10 2003-07-31 Bayer Ag 1,4-di-hidropiridinas fenil-substituidas com actividade cerebral
AR008789A1 (es) * 1996-07-31 2000-02-23 Bayer Corp Piridinas y bifenilos substituidos
US6812345B2 (en) 2000-06-15 2004-11-02 Bristol-Myers Squibb Company HMG-CoA reductase inhibitors and method
US6627636B2 (en) 2000-06-15 2003-09-30 Bristol-Myers Squibb Company HMG-CoA reductase inhibitors and method
US6620821B2 (en) 2000-06-15 2003-09-16 Bristol-Myers Squibb Company HMG-CoA reductase inhibitors and method
DE10135013A1 (de) * 2001-07-18 2003-01-30 Bayer Ag Herstellung von Pyridylverbindungen
US7659281B2 (en) 2006-04-25 2010-02-09 Bristol-Myers Squibb Company HMG-CoA reductase inhibitors

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0098690B1 (en) * 1982-06-14 1987-09-09 Takeda Chemical Industries, Ltd. Vinyl carboxylic acid derivatives, their production and use
US4681893A (en) * 1986-05-30 1987-07-21 Warner-Lambert Company Trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl)alkyl]-4-hydroxypyran-2-one inhibitors of cholesterol synthesis
NO177005C (no) * 1988-01-20 1995-07-05 Bayer Ag Analogifremgangsmåte for fremstilling av substituerte pyridiner, samt mellomprodukter til bruk ved fremstillingen

Also Published As

Publication number Publication date
NZ227636A (en) 1990-09-26
HU208691B (en) 1993-12-28
PT89478A (pt) 1989-10-04
PT89478B (pt) 1993-12-31
NO890046L (no) 1989-07-21
EP0325129A2 (de) 1989-07-26
ES2058343T3 (es) 1994-11-01
CN1034716A (zh) 1989-08-16
HUT50775A (en) 1990-03-28
KR890011847A (ko) 1989-08-22
FI92195C (sv) 1994-10-10
FI890257A (sv) 1989-07-21
EP0325129B1 (de) 1994-09-07
US4968689A (en) 1990-11-06
AU2861389A (en) 1989-07-20
NO890046D0 (no) 1989-01-05
ATE111081T1 (de) 1994-09-15
AU614810B2 (en) 1991-09-12
DE58908290D1 (de) 1994-10-13
IL88971A (en) 1993-07-08
EP0325129A3 (en) 1990-12-19
DK23289A (da) 1989-07-21
DK23289D0 (da) 1989-01-19
FI890257A0 (sv) 1989-01-18
IL88971A0 (en) 1989-08-15
JPH021478A (ja) 1990-01-05
JP2712107B2 (ja) 1998-02-10

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Owner name: BAYER AKTIENGESELLSCHAFT