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FI91149B - Förfarande för framställning av som läkemedel användbara 2-(aminoalkyltio)metyl-1,4-dihydropyridiner - Google Patents

Förfarande för framställning av som läkemedel användbara 2-(aminoalkyltio)metyl-1,4-dihydropyridiner Download PDF

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Publication number
FI91149B
FI91149B FI885930A FI885930A FI91149B FI 91149 B FI91149 B FI 91149B FI 885930 A FI885930 A FI 885930A FI 885930 A FI885930 A FI 885930A FI 91149 B FI91149 B FI 91149B
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Finland
Prior art keywords
methyl
ethoxycarbonyl
dihydropyridine
formula
compound
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FI885930A
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English (en)
Finnish (fi)
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FI91149C (sv
FI885930A (sv
Inventor
Carmelo Gandolfi
Silvano Spinelli
Sergio Tognella
Marco Frigerio
Odoardo Tofanetti
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Boehringer Mannheim Italia
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Publication of FI885930A publication Critical patent/FI885930A/sv
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Publication of FI91149C publication Critical patent/FI91149C/sv

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    • 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
    • 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
    • A61P9/10—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
    • 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
    • C07D401/04—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
    • 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
    • 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
    • C07D405/04—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 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
    • C07D405/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/12—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 linked by a chain containing hetero atoms as chain links

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

Claims (8)

1. Förfarande för framställning av som läkemedel användbara föreningar med formeIn I 5 3 \......^ 1° CM, y CHj-S-lCKjl^-CK- (OI CH0 n dar: 15 R·! avser: en COC6H5-, CN- eller N02-grupp; 20 en COORa-grupp, där Ra avser vate, en rak eller förgrenad Cj-C6-alkyl, varvid den valbart innefattar Atminstone en sekundar aminogrupp med formeln -NR4R5 dar R4 och RJt som kan vara likadana eller olika, avser Ci-Cg-alkyl, bensyl;
25 R2 Ar en fenylring som ar icke-substituerad eller har en fluor-, klor-, nitro-, cyano-, Cj^Cg-alkoxi- eller metyltiosubstituent; R3 avser en COORa-grupp där Ra är C1-C6 rak eller förgrenad alkyl;
30 P är vate eller -(CHz)p-W; N-Pi ar en rest av en primar eller sekundär aminogrupp dar Pi ar väte eller -(CH2)p-W; 35. kan tillsammans med Px och den kvaveatom vid vilken P2 ar bunden bilda en pyrrolidinring; 91149 U vaijes frAn en grupp som bestir av hydroximetyl, en C02R-grupp, dar R Ar vate eller lägre C1-C4-alkyl, CN-gruppen, en C3-C7 cykloalkylring samt fenylringen; 5. ar ett heltal 1-3: n ar noll eller heltalet 1 eller 2; p Ar noll eller heltalet 1-3, 10 samt för framställning av deras salter, enantiomerer, diastereoisome-rer eller blandningar, kännetecknat dArav, att a) man bildar en tioeterbindning genom att bringa en förening med den 15 allmanna formeln (II) Vie' CI i J <K2r (in
20 M att reagera med en förening med formeln III 9S P.......P I X 1 Yl‘(CH2,m’CM“\ (III) CHO 30 i vilka formler Rlf R2, R3, m, P, N-Pj^ Ar i enlighet med de ovan pre-senterade formlema; - antigen Y eller 'il avser en tiolgrupp eller en maskerad tiolgrupp, 35 sisom tio-C2-C12-alkanoylester eller ett tiouroniumsalt - S-(C-NRβ)NR7R8¢+)Y2<”,, varvid den ena av dessa är en känd avgiende grupp sAsom klor, brom, jod, trifluormetansulfonat, ett alkyl- eller ett arylsulfonat;
2. Förfarande enligt patentkrav 1, kännetecknad därav, att utgängsämnena väljes för att framstalla 4-(3-nitrofenyl), (3-klorfenyl), (3-cyanofenyl), (3-metoxifenyl), (4-fluorfenyl), (3-metyltiofenyl), (2-fluoro-5-metyltiofenyl)-derivat av 2-(2-formyla- 25 minoetyltio)metyl- 3-etoxikarbonyl-5-metoxikarbonyl-6-metyl-1,4-dihy- dropyridin samt för framställning av deras salter, enantiomerer, dias-tereoisomerer eller blandningar.
3. Förfarande enligt patentkrav 1, kännetecknad därav, 30 att utgängsämnena väljes för att framställa 2-(2-formylaminoetyltio)- metyl-3-etoxikarbonyl-5-(2-N,N-dimetylamino)etoxikarbonyl-4-(m-klorfe-nyl)-6-metyl-l,4-dihydropyridin samt för framställning av deras salter, enantiomerer, diastereoisomerer eller blandningar. 35
4. Förfarande enligt patentkrav 1, kännetecknad därav, att utgängsämnena väljes för att framställa 2-(2-formylaminoetyltio)-metyl- 3-metoxietoxikarbonyl-5-metoxikarbonyl-4-(3-metyltiofenyl)-6- metyl-1,4-dihydropyridin samt för framställning av deras salter, enan-tiomerer, dlastereolsomerer eller blandningar.
5. Förfarande enligt patentkrav 1, kännetecknad därav, 5 att utgängsämnena väljes för att framställa 2-[2-N-(2-cyanoetyl)-N-formylaminoetyltio]metyl-3-etoxikarbonyl-5-metoxikarbonyl-4-(m-nitrofenyl) -6 -metyl-1, 4- dihydropyridin samt för framställning av deras salter, enantiomerer, diastereoisomerer eller blandningar. 10
6. Förfarande enligt patentkrav 1, kännetecknad därav, att utgängsämnena väljes för att framställa 2-(2-formylaminoetyltio)-metyl-3-etoxikarbonyl-5-(2-N-metyl-N-bensylamino)-etoxikarbonyl-4-(m-nitrofenyl)-6-metyl-l,4-dihydropyridin samt för framställning av deras salter, enantiomerer, diastereoisomerer eller blandningar. 15
5 CHj i vilka formler R2, R3, P, NPX och m har de ovan presenterade defini-tionema och R^ är förelaktigt C02Ra, CN, COCH3, COC6H5; 10 d) en förening med foroeln VIII formyleras •Vx I 7'1 (vni) c-ι f N« ‘e'« 15 1 vilken forme 1 R1( Rj, R3, P, Px och n har de ovan presenterade defi-nltlonerna efter vilket produktema frän reaktlonema som presenterats 1 punktema a) - d) valbart kan behandlas vldare t.ex. genom oxide-ring, saltbildning eller genom att separera isomerema. 20
5. Rg, R7, R8 son är likadana eller ollka avser väte eller en alkylgrupp och Υ2("} dr en farmaceutlskt acceptabel anjon; b) en förening med forneln IV 10 * -,^2 (IV1 15 cykllseras med en alkylidenförening med formeln V on 0^ ? /*1
20. CH--5- (CH } -CH-N 2. m CHO (V) i vilka formler R1( R2, R3, P, NPX och m har de ovan presenterade defi-25 nitionerna; c) en förening med formeln VI 30 fr-f M-CH—(CH,)m— S—H C' NH, (VI) / 2 2 2 CKO 35 il 91149 cykliseras med en alkylidenförening med formeIn VII H "C-V 0>k (VI11
7. Förfarande enligt patentkrav 1, kännetecknad därav, att utgängsämnena väljes för att framställa en diastereoisomer av 2 *(2- formylamino-2-fenyletyltio)metyl-3-etoxikarbonyl-5-metoxikarbo-nyl-4-(m-nitrofenyl)-6-metyl-l,4-dihydropyrldin samt för framställning 20 av deras salter, enantiomerer, diastereoisomerer eller blandningar.
8. Förfarande enligt patentkrav 1, kännetecknad därav, att utgängsämnena väljes för att framställa en diastereoisomer av 2 -(N-formyl-pyrrolidin-2-yl metyltio)metyl-3-etoxikarbonyl-5-metoxi-25 karbonyl-4-(m-nitrofenyl)-6-metyl-l,4-dihydropyridin samt för framställning av deras salter, enantiomerer, diastereoisomerer eller blandningar. li
FI885930A 1986-06-27 1988-12-21 Förfarande för framställning av som läkemedel användbara 2-(aminoalkyltio)metyl-1,4-dihydropyridiner FI91149C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IT2096586 1986-06-27
IT20965/86A IT1204421B (it) 1986-06-27 1986-06-27 2-(aminoalchiltio)metil-1,4-diidropiridine,un metodo per la loro preparazione e composizioni farmaceutiche che le contengono
EP8700335 1987-06-25
PCT/EP1987/000335 WO1988000187A1 (en) 1986-06-27 1987-06-25 2-(aminoalkylthio)methyl-1,4-dihydropyridine, a method for the preparation thereof and pharmaceutical compositions containing them

Publications (3)

Publication Number Publication Date
FI885930A FI885930A (sv) 1988-12-21
FI91149B true FI91149B (sv) 1994-02-15
FI91149C FI91149C (sv) 1994-05-25

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Application Number Title Priority Date Filing Date
FI885930A FI91149C (sv) 1986-06-27 1988-12-21 Förfarande för framställning av som läkemedel användbara 2-(aminoalkyltio)metyl-1,4-dihydropyridiner

Country Status (19)

Country Link
US (1) US5047414A (sv)
EP (2) EP0312541B1 (sv)
JP (1) JPH0832686B2 (sv)
KR (1) KR950002154B1 (sv)
AU (1) AU603595B2 (sv)
CA (1) CA1322753C (sv)
DK (1) DK164051C (sv)
ES (1) ES2037029T3 (sv)
FI (1) FI91149C (sv)
GR (1) GR3004954T3 (sv)
HU (1) HU201305B (sv)
IT (1) IT1204421B (sv)
MX (1) MX7134A (sv)
NZ (1) NZ220868A (sv)
PH (1) PH23208A (sv)
PL (1) PL156170B1 (sv)
RU (1) RU1816282C (sv)
WO (1) WO1988000187A1 (sv)
ZA (1) ZA874636B (sv)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1213555B (it) * 1986-12-11 1989-12-20 Boehringer Biochemia Srl 2 metiltiometildiidropiridine, un processo per laloro preparazione e composizioni farmaceutiche che le contengono.

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CS228917B2 (en) * 1981-03-14 1984-05-14 Pfizer Method of preparing substituted derivatives of 1,4-dihydropyridine
IL68604A0 (en) * 1982-05-21 1983-09-30 Haessle Ab Processes for preparing therapeutically active dihydropyridines and intermediates for the processes
PH19166A (en) * 1982-09-04 1986-01-16 Pfizer Dihydropyridined,pharmaceutical compositions and method of use
PL140573B1 (en) * 1982-12-21 1987-05-30 Pfizer Method of obtaining new dihydropyridine derivatives
GB8306666D0 (en) * 1983-03-10 1983-04-13 Pfizer Ltd Therapeutic agents
GR851819B (sv) * 1984-08-17 1985-11-26 Wyeth John & Brother Ltd
KR930011486B1 (ko) * 1985-08-06 1993-12-08 베링거 만하임 이탈리아 에스.피.에이. 제약상 유효한 2-티오메틸-치환-1,4-디히드로피리딘

Also Published As

Publication number Publication date
WO1988000187A1 (en) 1988-01-14
PL266481A1 (en) 1988-09-01
CA1322753C (en) 1993-10-05
EP0312541B1 (en) 1992-08-26
IT1204421B (it) 1989-03-01
AU603595B2 (en) 1990-11-22
FI91149C (sv) 1994-05-25
KR880701228A (ko) 1988-07-26
HU201305B (en) 1990-10-28
EP0254064A1 (en) 1988-01-27
ES2037029T3 (es) 1993-06-16
DK99588D0 (da) 1988-02-25
EP0312541A1 (en) 1989-04-26
IT8620965A0 (it) 1986-06-27
FI885930A (sv) 1988-12-21
DK164051B (da) 1992-05-04
KR950002154B1 (ko) 1995-03-14
RU1816282C (ru) 1993-05-15
MX7134A (es) 1993-10-01
PL156170B1 (pl) 1992-02-28
ZA874636B (en) 1988-03-30
NZ220868A (en) 1989-10-27
JPH0832686B2 (ja) 1996-03-29
AU7696987A (en) 1988-01-29
PH23208A (en) 1989-06-06
DK164051C (da) 1992-09-28
US5047414A (en) 1991-09-10
JPH01503065A (ja) 1989-10-19
DK99588A (da) 1988-02-25
EP0254064B1 (en) 1992-06-17
GR3004954T3 (sv) 1993-04-28
HUT49572A (en) 1989-10-30

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Owner name: BOEHRINGER MANNHEIM ITALIA S.P.A.