FI89166B - Foerfarande foer framstaellning av terapeutiskt aktiva heterocykliska foereningar - Google Patents

Foerfarande foer framstaellning av terapeutiskt aktiva heterocykliska foereningar Download PDF

Info

Publication number
FI89166B
FI89166B FI853103A FI853103A FI89166B FI 89166 B FI89166 B FI 89166B FI 853103 A FI853103 A FI 853103A FI 853103 A FI853103 A FI 853103A FI 89166 B FI89166 B FI 89166B
Authority
FI
Finland
Prior art keywords
formula
compound
methyl
defined above
dihydro
Prior art date
Application number
FI853103A
Other languages
English (en)
Finnish (fi)
Other versions
FI853103A0 (fi
FI853103L (fi
FI89166C (sv
Inventor
John Leheup Archibald
Terence James Ward
Albert Opalko
Original Assignee
Wyeth John & Brother Ltd
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 GB848421039A external-priority patent/GB8421039D0/en
Priority claimed from GB858515751A external-priority patent/GB8515751D0/en
Application filed by Wyeth John & Brother Ltd filed Critical Wyeth John & Brother Ltd
Publication of FI853103A0 publication Critical patent/FI853103A0/fi
Publication of FI853103L publication Critical patent/FI853103L/fi
Application granted granted Critical
Publication of FI89166B publication Critical patent/FI89166B/fi
Publication of FI89166C publication Critical patent/FI89166C/sv

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • 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
    • 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
    • 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
    • A61P9/12—Antihypertensives
    • 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
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • 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

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Claims (6)

1 Ar R02C\J 10 (II) 15 bringas att reagera med en förening med formeln /C02r2 I (V) 20 h2n t2 i vilka formlar Ar, Rl och R2 Mr ovan definierade och den ena av grupper T1 och T2 Mr A och den andra Mr B, varvid A 25 och B Mr ovan definierade förutsatt, att nMr T2 Mr A, T1 Mr annan Μη amino, varvid en motsvarande förening med formeln I erhälls; eller (iii) föreningar med formeln
30 ArCH°' R,°2C\ /co2R2 eller
35 T 0 NH2 T2 (VI) (V) 30 8 91 6 6 i vilka formlar Ar, R1 och R2 är ovan definierade och den ena av grupper T1 och T2 är A och den andra är B, varvid A och B är ovan definierade förutsatt, att när T2 är A, T1 kan inte vara amino, bringas att reagera sinsemellan, var-5 vid en motsvarande förening med formeln I erhälls; eller (iv) en förening med formeln Ar r1°2C s/^yCO R2
10. I (VII) B ^Nnx^(CH2) Z1 H 15 bringas att reagera med en förening med formeln HR3, HOR3 eller H2NCH2R3 (villa) (vmb) (vine) 20 eller med dess anjon, i vilka formlar B, R1, R2 och R3 är ovan definierade, Z1 är halogen eller en sulfonyloxigrupp och v är 1 eller 2 förutsatt, att (a) när v är 2, Z1 kan ocksä vara en dialkylamino-eller kvaternär ammoniumgrupp, och 25 (b) när en förening med formeln Vlllb eller VIIIc används, v är 1, eller (v) den ovan definierade föreningen med formeln I förvandlas till sitt syraadditionssalt genom tilIsättning av syra eller ett syraadditionssalt görs basiskt, varvid 30 en förening med formeln I erhälls; eller (vi) den ovan definierade föreningen med formeln I, som har en basisk substituent, förvandlas till sitt kva-ternärt ammoniumsalt genom en reaktion med ett alkylerande ämne. 35 li 3i 89166
1. Förfarande för framställning av en terapeutiskt aktiv förening med formeln 5 R V Xcv! Xi 10 H i vilken Ar är fenyl, som är substituerad med ätminstone en 15 substituent som är N02, Cl, F, CF3 eller 0CHF2, eller Ar är 4-kinolyl eller bensofurazan-4-yl, R1 och R2 är lika eller olika och är vardera even-tuellt metoxisubstituerade alkylgrupper med 1-6 kolato-mer,
20 A är en grupp med formeln -XR3, i vilken X är en -CH2-, -CH2CH2-, -CH20- eller -CH2NHCH2-grupp och R3 är 1- imidazolyl, 1-bensimidazolyl, 3-pyridyl eller 1,2,4-tria-zol-l-yl, varvid vardera av dessa grupper är eventuellt substituerad med en metylgrupp, och 25 B är CH3 eller NH2, eller för framställning av dess sait, känneteck-n a t därav, att (i) föreningar med formlar 30 _1 Ar R °->C^ J 2 2 ^co2r NH-3 eller To 0 (II> (HI) (IV) 35 29 891 66 i vilka formlar Ar, R1 och Rz Mr ovan definierade och den ena av grupper T1 och T2 Mr A och den andra Mr B, varvid A Mr ovan definierad och B Mr CH3, bringas att reagera sins-emellan, varvid en motsvarande förening med formeln I er-5 hMlls; eller (ii) en förening med formeln
2. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att den framställda föreningen med formeln I är 1,4-dihydro-2-(imidazol-1-ylmetyl)-6-metyl-4-(3-nitrofenyl)-pyridin-3,5-dikarboxylsyras 3-etyl-5- 5 metyldiester.
3. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att den framställda föreningen med formeln I är 1,4-dihydro-2-[2-(imidazol-l-yl)etyl]-6-me-tyl-4-(2-nitrofenyl)pyridin-3,5-dikarboxylsyras dietyl- 10 ester.
4. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att den framställda föreningen med formeln I är 1,4-dihydro-2-metyl-4-(3-nitrofenyl)-6-[(3-pyridyloxi)metyl]pyridin-3,5-dikarboxylsyras 5-etyl-3-me- 15 tyldiester.
5. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att den framställda föreningen med formeln I är 4-(2,3-diklorfenyl)-l,4-dihydro-2-[2-(l-imi-dazolyl)etyl]-6-metylpyridin-3,5-dikarboxylsyras dimetyl- 20 ester.
6. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att den framställda föreningen med formeln I är l,4-dihydro-2-(l-imidazolylmetyl)-6-metyl-4-(3-nitrofenyl)pyridin-3,5-dikarboxylsyras 3-etyl-5-metyl- 25 ester.
FI853103A 1984-08-17 1985-08-13 Förfarande för framställning av terapeutiskt aktiva heterocykliska för eningar FI89166C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB848421039A GB8421039D0 (en) 1984-08-17 1984-08-17 Heterocyclic compounds
GB8421039 1984-08-17
GB858515751A GB8515751D0 (en) 1985-06-21 1985-06-21 Heterocyclic compounds
GB8515751 1985-06-21

Publications (4)

Publication Number Publication Date
FI853103A0 FI853103A0 (fi) 1985-08-13
FI853103L FI853103L (fi) 1986-02-18
FI89166B true FI89166B (fi) 1993-05-14
FI89166C FI89166C (sv) 1993-08-25

Family

ID=26288137

Family Applications (1)

Application Number Title Priority Date Filing Date
FI853103A FI89166C (sv) 1984-08-17 1985-08-13 Förfarande för framställning av terapeutiskt aktiva heterocykliska för eningar

Country Status (23)

Country Link
US (1) US5068337A (sv)
EP (1) EP0172029B1 (sv)
JP (1) JPH0680053B2 (sv)
KR (1) KR930000167B1 (sv)
AR (1) AR241417A1 (sv)
AT (1) ATE61055T1 (sv)
AU (1) AU587388B2 (sv)
CA (1) CA1310011C (sv)
CZ (1) CZ279473B6 (sv)
DE (1) DE3581858D1 (sv)
DK (1) DK374185A (sv)
ES (1) ES8604564A1 (sv)
FI (1) FI89166C (sv)
GB (1) GB2168969B (sv)
GR (1) GR851819B (sv)
HU (1) HU194868B (sv)
IE (1) IE58706B1 (sv)
IL (1) IL75943A (sv)
MY (1) MY101736A (sv)
NZ (1) NZ212956A (sv)
PH (1) PH26049A (sv)
PT (1) PT80956B (sv)
SU (1) SU1486059A3 (sv)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI862343A (fi) * 1985-06-17 1986-12-18 Warner Lambert Co Foerfarande foer framstaellning av terapeutiskt verkande 1,4-dihydropyridinfoereningar.
IT1204421B (it) * 1986-06-27 1989-03-01 Boehringer Biochemia Srl 2-(aminoalchiltio)metil-1,4-diidropiridine,un metodo per la loro preparazione e composizioni farmaceutiche che le contengono
EP0225175A3 (en) * 1985-11-28 1988-12-28 FISONS plc Dihydropyridine derivatives, processes for their preparation and pharmaceutical compositions thereof
GB8602518D0 (en) * 1986-02-01 1986-03-05 Wyeth John & Brother Ltd 1 4-dihydropyridines
DE3617976A1 (de) * 1986-05-28 1988-01-14 Alter Sa 1,4-dihydropyridin, verfahren zu dessen herstellung und dessen verwendung in antithrombotischen medikamenten
FR2602231B1 (fr) * 1986-08-04 1988-10-28 Adir Nouveaux derives de la dihydro-1,4 pyridine, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
AU1153088A (en) * 1986-12-24 1988-07-27 Boehringer Biochemia Robin S.P.A New aralkyl-1,4-dihydropyridines, a method for their preparation and pharmaceutical compositions containing them
GB8729471D0 (en) * 1987-12-17 1988-02-03 Wyeth John & Brother Ltd New crystal form
JPH0286981A (ja) * 1988-09-22 1990-03-27 Aisin Seiki Co Ltd ロータリ圧縮機
US5616591A (en) * 1992-03-27 1997-04-01 E.R. Squibb & Sons, Inc. Indole- and benzimidazole-substituted quinoline derivatives
DE4233601A1 (de) * 1992-10-06 1994-04-07 Bayer Ag 3-substituierte Chinolin-5-carbonsäuren
WO1995000649A1 (en) * 1993-06-25 1995-01-05 Smithkline Beecham Plc Lipoprotein associated phospholipase a2, inhibitors thereof and use of the same in diagnosis and therapy
LV12200B (lv) * 1997-07-03 1999-04-20 Gunārs DUBURS Antidiabētisks līdzeklis
WO2002053542A1 (en) * 2000-12-29 2002-07-11 Pfizer Limited Process for making amlodipine maleate
DE60236851D1 (en) * 2001-02-14 2010-08-12 Warner Lambert Co Pyrimidinmatrixmetalloproteinaseinhibitoren
US6566359B1 (en) 2002-05-20 2003-05-20 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College 2,4,6-trimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid esters as neuroprotective drugs

Family Cites Families (21)

* 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
DE2639257A1 (de) * 1976-09-01 1978-03-02 Bayer Ag Aminoalkylidenamino-1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2658183A1 (de) * 1976-12-22 1978-07-06 Bayer Ag In 2-position substituierte 1,4- dihydropyridin-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
US4177278A (en) * 1977-04-05 1979-12-04 Bayer Aktiengesellschaft 2-Alkyleneaminodihydropyridines compounds, their production and their medicinal use
DE2738153A1 (de) * 1977-08-24 1979-03-08 Bayer Ag 2-pyridyl-1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
US4307103A (en) * 1978-09-08 1981-12-22 Fujisawa Pharmaceutical Co., Ltd. Dihydropyridine derivative, processes for preparation thereof and pharmaceutical composition comprising the same
JPS5547656A (en) * 1978-09-29 1980-04-04 Dainippon Pharmaceut Co Ltd 2-(2-substituted aminoethyl)-1,4-dihydropyridine derivative and its derivative
DE2844595A1 (de) * 1978-10-13 1980-04-30 Bayer Ag Acylaminodihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
CS228917B2 (en) * 1981-03-14 1984-05-14 Pfizer Method of preparing substituted derivatives of 1,4-dihydropyridine
SE8105230L (sv) * 1981-09-03 1983-03-04 Haessle Ab Nya dihydropyridiner
EP0080220B1 (en) * 1981-11-17 1986-02-19 FISONS plc Dihydropyridines, methods for their production and their formulation and use as pharmaceuticals
DE3207982A1 (de) * 1982-03-05 1983-09-08 Bayer Ag, 5090 Leverkusen Neue 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihrer verwendung in arzneimitteln
DK161312C (da) * 1982-03-11 1991-12-09 Pfizer Analogifremgangsmaade til fremstilling af 2-aminoalkoxymethyl-4-phenyl-6-methyl-1,4-dihydropyridin-3,5-dicarboxylsyreestere eller syreadditionssalte deraf samt phthalimidoderivater til anvendelse som udgangsmateriale ved fremgangsmaaden
WO1983003249A1 (en) * 1982-03-17 1983-09-29 Yoshitomi Pharmaceutical 1,4-dihydropyridine-3,5-dicarboxylate derivatives
DE3363743D1 (en) * 1982-07-22 1986-07-03 Pfizer Ltd Dihydropyridine anti-ischaemic and antihypertensive agents
PH19166A (en) * 1982-09-04 1986-01-16 Pfizer Dihydropyridined,pharmaceutical compositions and method of use
PL140069B1 (en) * 1982-12-21 1987-03-31 Pfizer Method of obtaining new derivatives of dihydropiridine
US4515799A (en) * 1983-02-02 1985-05-07 Pfizer Inc. Dihydropyridine anti-ischaemic and antihypertensive agents
EP0125803A3 (en) * 1983-04-27 1987-01-21 FISONS plc Pharmaceutically active dihydropyridines
US4568677A (en) * 1983-07-23 1986-02-04 Pfizer Inc. 2-(4-Pyrimidone alkoxyalkyl) dihydropyridine anti-ischaemic and antihypertensive agents
GB8414518D0 (en) * 1984-06-07 1984-07-11 Pfizer Ltd Therapeutic agents

Also Published As

Publication number Publication date
GB2168969A (en) 1986-07-02
JPH0680053B2 (ja) 1994-10-12
KR870002122A (ko) 1987-03-30
EP0172029B1 (en) 1991-02-27
AU4572685A (en) 1986-02-20
MY101736A (en) 1992-01-17
PT80956B (pt) 1987-12-30
GB8520485D0 (en) 1985-09-18
DK374185A (da) 1986-02-18
ES8604564A1 (es) 1986-02-01
DK374185D0 (da) 1985-08-16
FI853103A0 (fi) 1985-08-13
SU1486059A3 (ru) 1989-06-07
GR851819B (sv) 1985-11-26
CA1310011C (en) 1992-11-10
AR241417A1 (es) 1992-07-31
US5068337A (en) 1991-11-26
FI853103L (fi) 1986-02-18
CZ592285A3 (en) 1995-02-15
IL75943A (en) 1988-12-30
AU587388B2 (en) 1989-08-17
CZ279473B6 (cs) 1995-05-17
EP0172029A1 (en) 1986-02-19
NZ212956A (en) 1988-09-29
ATE61055T1 (de) 1991-03-15
DE3581858D1 (en) 1991-04-04
GB2168969B (en) 1987-09-03
JPS6157578A (ja) 1986-03-24
PH26049A (en) 1992-01-29
FI89166C (sv) 1993-08-25
HU194868B (en) 1988-03-28
IE58706B1 (en) 1993-11-03
IE851860L (en) 1986-02-17
IL75943A0 (en) 1985-12-31
KR930000167B1 (ko) 1993-01-11
HUT40106A (en) 1986-11-28
PT80956A (en) 1985-09-01
ES546189A0 (es) 1986-02-01

Similar Documents

Publication Publication Date Title
FI89166B (fi) Foerfarande foer framstaellning av terapeutiskt aktiva heterocykliska foereningar
CS235334B2 (en) Method of 1,4-dihydropyridines production
FI57749C (fi) Foerfarande foer framstaellning av analgetiska n-/1-(omega-fenylalkyl)-piperidyl-4/-n-(alfa-pyridyl)-karbonsyraamider och deras syraadditionssalter
US4576957A (en) N-(Substituted phenyl)-N'-[(1H-imidazol-1-yl) and (1H-1,2,4-triazol-1-yl)alkyl]ureas
PL140573B1 (en) Method of obtaining new dihydropyridine derivatives
CZ396591A3 (en) Enantiomers of 1,4-dihydropyridine process of their preparation and pharmaceutical compositions prepared therefrom
CS241549B2 (en) Method of 1,4-dihydropyridines production
AU640208B2 (en) Pyridine and related aza heterocycle derivatives as cardiovascular agents
HU198924B (en) Process for producing n-alkylbenz/cd/indol-2-amines having heterocyclic ring in omega position, as well as pharmaceutical compositions comprising same
US4900750A (en) 1.4-Dihydropyridines
US4820842A (en) 2-substituted-1,4-dihydropyridines
US4710502A (en) 3-heteroarylalkyl-4-quinazolinones
US4505920A (en) Certain N-substituted-4-aryl-3,5-pyridine dicarboxylates and their antihypertensive use
US4723014A (en) Process for the preparation of 2-substituted-1,4-dihydropyridines
US4547502A (en) Dihydropyridines and their use in treating cardiac conditions and hypertension
US4555519A (en) Thromboxane synthetase enzyme inhibiting N-[(1H-imidazol-1-yl) and (1H-1,2,4-triazol-1-yl)alkyl]pyridinecarboxamides
US4782064A (en) 2-heteroaryl-alkyl-1H-benz[de]-isoquinoline-1,3(2H)-diones
EP0233015B1 (en) 1,4-Dihydropyridines
US4753944A (en) Pharmaceutical methods of using 3-heteroarylalkyl-4-quinazolinones
KR960001916B1 (ko) 1,4-디하이드로피리딘
CS249525B2 (cs) Způsob výroby dihydropyridinů

Legal Events

Date Code Title Description
BB Publication of examined application
MM Patent lapsed

Owner name: JOHN WYETH & BROTHER LIMITED