FI91634B - Förfarande för framställning av terapeutiskt användbara 1,4-dihydropyridinderivat - Google Patents

Förfarande för framställning av terapeutiskt användbara 1,4-dihydropyridinderivat Download PDF

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Publication number
FI91634B
FI91634B FI873350A FI873350A FI91634B FI 91634 B FI91634 B FI 91634B FI 873350 A FI873350 A FI 873350A FI 873350 A FI873350 A FI 873350A FI 91634 B FI91634 B FI 91634B
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FI
Finland
Prior art keywords
phenyl
formula
nitro
dihydro
dimethyl
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FI873350A
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English (en)
Finnish (fi)
Other versions
FI873350A0 (sv
FI873350A (sv
FI91634C (sv
Inventor
Alexander Lawrence Johnson
Petrus Bernardus Ma Timmermans
Philip Ma
Ruth Richmond Wexler
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Du Pont Merck Pharma
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Application filed by Du Pont Merck Pharma filed Critical Du Pont Merck Pharma
Publication of FI873350A0 publication Critical patent/FI873350A0/sv
Publication of FI873350A publication Critical patent/FI873350A/sv
Application granted granted Critical
Publication of FI91634B publication Critical patent/FI91634B/sv
Publication of FI91634C publication Critical patent/FI91634C/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • 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)
  • Cardiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Steroid Compounds (AREA)
  • Silicates, Zeolites, And Molecular Sieves (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (8)

1. Förfarande för framställning av nya terapeu-tiskt användbara 1,4-dihydropyridinderivat med formeln I 5 och farmaceutiskt godtagbara salter därav, ^ r1 4— R2 .. V, °2N'^j^\^R5 (I) N^CH3 H 15 i vilken formel R1 är H, C^-C^-alkoxi, nitro, halogen el-ler Cj-C^alkenyl, R2 är trifluormetyl, halogen eller 20 -0(CH2)n -N N- (alk)mAr’ där n är 1 - 12 och Ar' är fenyl, som kan vara substitue-rad med Ci-C^-alkoxi eller tr if luormetyl, eller Ar' är 2-25 pyrimidinyl eller 2-pyridinyl, m är 0 eller 1 och alk är C^-C^-alkylen, eller R2 är -0-CH2-X-CH2-N N-(alk)in-Ar' 30 \_/ där X är -CH=CH-, -CH-CH- eller en epoxid av dessa och alk, m och Ar' betecknar samma som ovan, och R5 är -C02R7, där R7 är « . « II 91634 43 - (CH2) γ-/ N-Ar1 5 -(CH2)2NH(CH2)2-0-Ar’ eller Cj-C^alkyl, varvid r är 1 - 10 och Ar' betecknar samma som ovan, eller R5 är -CONHPh, kännetecknat därav, att a) för framställnlng av föreningar med formeln I, 10 där R2 är -0-CH2-X-CH2-N^_N-(alk)m-Ar' eller 15 -0(CH2)n -N N- (alk)mAr ' 20 brlngas en förenlng med formeln iR1
0-CH2-X-CH2-R1:L -°(CH2)m-Rl1 ;5 eller YY - ' -a3 H3c^ n Ach H 3 I J H 30 (II) (II') varvid R11 är Br, Cl, I, OTs, OMs eller OTf och R1, R5 och X betecknar samma som ovan, i kontakt med en förenlng med formeln 44 91634 H-/ (alk) mAr1 (III) 5 där alk, m och Ar' betecknar sairaita som ovan, eller b) för framställning av föreningar med formeln I, där R5 är -C02R7, där R7 är / \ 10 -(CH2)r-N_^I-Ar' bringas en förenlng med formeln r1 15 Γ — R2 |C-H ° (I if ,IV) H-iC^ N ^CH-, 2° 3 A 3 där R11 är Br, Cl, I, OTs, OMs eller OTf och R1, R2 och r betecknar sairaita som ovan, i kontakt med en förening med formeln 25 H-N Vat' (III·) 30 där Ar' betecknar samma som ovan; och, om sä önskas, omvandlas en erhällen förenlng med formeln I tili ett farmaceutiskt godtagbart sait genom att omsätta förenlngen med en oorganlsk eller organisk syra. 35
2. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att man framställer 1,4-dihydro- II • 45 y 1634 2.6- dimetyl-5-nitro-4-[3-(trifluormetyl)fenyl]—[2—[4—(2— metoxifenyl-l-piperazinyl]etyl]ester-3-pyridinkarboxylsy-ra.
3. Förfarande enligt patentkravet 1, känne-5 tecknat därav, att man framställer 1,4-dihydro- 2.6- dimetyl-4-[3-(2-(4-(2-metoxifenyl)-l-piperazinyl)eto-xi)fenyl]-5-nitro-metylester-3-pyridinkarboxylsyra.
4. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 1,4-dihydro- 10 2,6-dimetyl-4-[2-(2-(4-(2-metoxifenyl)-l-piperazinyl)eto- xi)fenyl]-5-nitro-metylester-3-pyridinkarboxylsyra.
5. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 1,4-dihydro- 2.6- dimetyl-4-[2-(2-(4-(2-metoxifenyl)-l-piperazinyl)eto- 15 xi)-3-(trifluormetyl)fenyl]-5-nitro-metylester-3-pyridin- karboxylsyra.
6. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 1,4-dihydro- 2.6- dimetyl-4-[2-(3-(4-(2-metoxifenyl)-l-piperazinyl)- 20 propoxi)fenyl]-5-nitro-metylester-3-pyridinkarboxylsyra.
7. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 1,4-dihydro- 2.6- dimetyl-5-nitro-4-[2-(4-(4-(2-pyrimidinyl)-1-piper-azinyl)butoxi)fenyl]-metylester-3-pyridinkarboxylsyra. 25
8. Förfarande enligt patentkravet 1, känne- tecknat därav, att man framställer 1,4-dihydro- 2.6- dimetyl-4-[2-(5-(4-(2-metoxifenyl)-l-piperazinyl)pen-toxyl)fenyl]-5-nitro-metylester-3-pyridinkarboxylsyra.
FI873350A 1986-08-04 1987-08-03 Förfarande för framställning av terapeutiskt användbara 1,4-dihydropyridinderivat FI91634C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US89229386A 1986-08-04 1986-08-04
US89229386 1986-08-04
US6436187 1987-06-30
US07/064,361 US4868181A (en) 1986-08-04 1987-06-30 1,4-dihydropyridine derivatives with calcium agonist and alpha1 -antagonist activity

Publications (4)

Publication Number Publication Date
FI873350A0 FI873350A0 (sv) 1987-08-03
FI873350A FI873350A (sv) 1988-02-05
FI91634B true FI91634B (sv) 1994-04-15
FI91634C FI91634C (sv) 1994-07-25

Family

ID=26744430

Family Applications (1)

Application Number Title Priority Date Filing Date
FI873350A FI91634C (sv) 1986-08-04 1987-08-03 Förfarande för framställning av terapeutiskt användbara 1,4-dihydropyridinderivat

Country Status (12)

Country Link
US (1) US4868181A (sv)
EP (1) EP0255710A3 (sv)
KR (1) KR930004648B1 (sv)
AU (1) AU617650B2 (sv)
DK (1) DK403287A (sv)
FI (1) FI91634C (sv)
HU (1) HU201925B (sv)
IL (1) IL83413A0 (sv)
NO (1) NO171909C (sv)
NZ (1) NZ221284A (sv)
PT (1) PT85483B (sv)
SU (3) SU1607687A3 (sv)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5137889A (en) * 1983-12-02 1992-08-11 Otsuka Pharmaceutical Co., Ltd. Dihydropyridine derivatives and process for preparing the same
JPS63112560A (ja) * 1986-10-29 1988-05-17 Green Cross Corp:The ジヒドロピリジン誘導体
DE3711991A1 (de) * 1987-04-09 1988-10-20 Bayer Ag Dihydropyridinamide, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DE3737340A1 (de) * 1987-11-04 1989-05-24 Bayer Ag Neue fluormethoxyphenyl-dihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln
DE3737341A1 (de) * 1987-11-04 1989-05-18 Bayer Ag Neue fluormethoxyphenyl-dihydropyridine, verfahren zur herstellung und ihre verwendung in arzneimitteln
CA2009542C (en) * 1989-02-10 2000-03-14 Albert A. Carr Cyclic guanidines as calcium antagonists
US5106845A (en) * 1990-01-10 1992-04-21 Merrell Dow Pharmaceuticals Inc. Calcium antagonists
US5166148A (en) * 1990-07-09 1992-11-24 The Du Pont Merck Pharmaceutical Company 2-amino-1,4-dihydropyridine derivatives with calcium agonist and alpha1 -antagonist activity
DE4222770A1 (de) * 1992-07-10 1994-01-13 Bayer Ag Lichtaktivierbare 1-(2-Nitrobenzyl)-substituierte 1,4-Dihydropyridine
US5767131A (en) * 1993-04-05 1998-06-16 Synaptic Pharmaceutical Corporation Dihydropyridines and new uses thereof
US6211198B1 (en) 1993-04-05 2001-04-03 Synaptic Pharmaceutical Corporation Dihydropyridines and new uses thereof
IL109220A0 (en) * 1993-04-05 1994-07-31 Synaptic Pharma Corp Dihydropyridines and new uses thereof
DE4410822A1 (de) * 1994-03-24 1995-09-28 Schering Ag Neue Piperidin-Derivate
US5635503A (en) * 1995-06-07 1997-06-03 Bristol-Myers Squibb Company Dihydropyridine npy antagonists: piperazine derivatives
WO2000024716A1 (fr) * 1998-10-23 2000-05-04 Ajinomoto Co., Inc. Derives de dihydropyridine et compositions medicamenteuses contenant ces derives
EP2925739A4 (en) * 2012-11-28 2016-07-27 Stichting Dienst Landbouwkundi SUBSTITUTED DIHYDROPYRTOINS FOR PLANTS WITH SOMATIC EMBRYOGENESIS I

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Also Published As

Publication number Publication date
SU1607687A3 (ru) 1990-11-15
FI873350A0 (sv) 1987-08-03
NO873240L (no) 1988-02-05
SU1609452A3 (ru) 1990-11-23
HU201925B (en) 1991-01-28
DK403287D0 (da) 1987-08-03
FI873350A (sv) 1988-02-05
PT85483B (pt) 1990-06-29
FI91634C (sv) 1994-07-25
KR880002827A (ko) 1988-05-11
DK403287A (da) 1988-02-05
EP0255710A3 (en) 1989-01-04
PT85483A (en) 1987-09-01
KR930004648B1 (ko) 1993-06-02
HUT46907A (en) 1988-12-28
IL83413A0 (en) 1988-01-31
SU1650011A3 (ru) 1991-05-15
AU7650387A (en) 1988-02-11
US4868181A (en) 1989-09-19
NO171909B (no) 1993-02-08
EP0255710A2 (en) 1988-02-10
AU617650B2 (en) 1991-12-05
NZ221284A (en) 1989-12-21
NO171909C (no) 1993-05-19
NO873240D0 (no) 1987-08-03

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Owner name: THE DU PONT MERCK PHARMACEUTICAL COMPANY