NO132590B - - Google Patents
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- Publication number
- NO132590B NO132590B NO4730/70A NO473070A NO132590B NO 132590 B NO132590 B NO 132590B NO 4730/70 A NO4730/70 A NO 4730/70A NO 473070 A NO473070 A NO 473070A NO 132590 B NO132590 B NO 132590B
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- atoms
- alkyl
- ester
- above meaning
- Prior art date
Links
- -1 nitro, hydroxy Chemical group 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- QVTPWONEVZJCCS-UHFFFAOYSA-N 2-formylbenzonitrile Chemical compound O=CC1=CC=CC=C1C#N QVTPWONEVZJCCS-UHFFFAOYSA-N 0.000 description 2
- WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- HGZJJKZPPMFIBU-UHFFFAOYSA-N 3-formylbenzonitrile Chemical compound O=CC1=CC=CC(C#N)=C1 HGZJJKZPPMFIBU-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000003440 anti-fibrillation Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- QEVODHDZNJHKOP-UHFFFAOYSA-N diethyl 4-(3-cyanophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC(C#N)=C1 QEVODHDZNJHKOP-UHFFFAOYSA-N 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- RYVBNUSVVSVNBV-UHFFFAOYSA-N dimethyl 4-(4-cyanophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=C(C#N)C=C1 RYVBNUSVVSVNBV-UHFFFAOYSA-N 0.000 description 1
- MBCWESRPVGAMQE-UHFFFAOYSA-N dipropan-2-yl 4-(3-cyanophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C(C)(C)OC(=O)C1=C(NC(=C(C1C1=CC(=CC=C1)C#N)C(=O)OC(C)C)C)C MBCWESRPVGAMQE-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 1
- UDRCONFHWYGWFI-UHFFFAOYSA-N ethyl 3-oxopentanoate Chemical compound CCOC(=O)CC(=O)CC UDRCONFHWYGWFI-UHFFFAOYSA-N 0.000 description 1
- XCLDSQRVMMXWMS-UHFFFAOYSA-N ethyl 4-methyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)C XCLDSQRVMMXWMS-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
- GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 description 1
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- 210000002254 renal artery Anatomy 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000003235 vasospasmolytic effect Effects 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Description
Oppfinnelsen vedrører analogifremgangsmåte til fremstilling av terapeutisk, aktive 1,4-dihydropyridiner med den generelle formel: ..
hvori R'betyr alkyl med 1-4 C-atomer,
R"'betyr alkyl eller alkenyl med inn-til 6 C- ' atomer, eventuelt cyklisk og/eller eventuelt avbrutt i kjeden med 1 til 2 oksygenatomer eller substituert med- en hydroksygruppe,
R'" betyr en- nitrilsubstituert fenyT, som dessuten :k'an inneholde eri substituent fra gruppen- nitril,. nitro, hydroksy, acyloksy, alkyl^ alkoksy, halogen, amino eller acylamino,
idet fremgangsmåten erkarakterisert vedat1 i organiske opp-løsningsmidler som alkoholer, dioksan, iseddik, dimetylformamid, dimetylsulfoksyd, acetdnitril eller, i vann ved forhøyet temperatur, overveiende ved oppløsningsmidlets koketemperatur, omsettes aldehyder med den generelle formel
hvori R'" har den ovennevnte betydning, med acylfettsyreestere med den generelle formel
hvori R' og R" har ovennevnte betydning og ammoniakk eller" ammoniumsalter.
Som omsetningskomponenter kan det f.eks. finne anvendelse:
Aldehyder:
2-, 3- eller 4-cyanbenzaldehyd, 4-klor-3~cyanbenzaldehyd.
A cylfettsyreestere:
Aceteddiksyremetylester, aceteddiksyreetylester, aceteddiksyrepropylester, aceteddiksyreisopropylester, acet-eddiksyreallylester, propionyleddiksyreetylester, butyryl-eddiksyreetylester, isobutyryleddiksyreetylestér.
De nye forbindelser er stoffer anvendbare som legemidler. De har et bredt og mangesidig farmakologisk virkningsspektrum.
I detalj kunne det i dyreeksperiment:påvises følgende hovedvirkninger: 1. Forbindelsene bevirker ved parenteral, oral og perlingual tilførsel en tydelig og langvarig utvidelse, av coronarkarene. Virkningen på coronarkarene forsterkes ved en
samtidig'nitritlignende hjerteavlastende effekt. De in-fluerer resp. forandrer hjertestoffvekselen i retning av en energibesparelse. 2. Energiserbarheten av irritasjonsdannelses- og energiser-ingsytelsessystemet innen hjertet nedsettes således at en terapeutisk dose resulterer i påvisbar antiflimmer-virkning. 3. Tonusen.av karenes glatte muskulatur forminskes sterkt under forbindelsenes virkning. Denne karspasmolytiske virkning kan finne sted i det samlede karsystem eller manifestere seg mer eller mindre isolert i omskrivende karområder (som f.eks. sentralnervesystemet) i 4. Forbindelsene senker blodtrykket av normotone og hyper-tone dyr og kan således anvendes som antihypertensive midler. 5. Forbindelsene har sterk muskulær-spasmolytiske virkninger, som tydeliggjøres på den glatte muskulatur av mage-tarm-kanalen, urogenitalkanalen og respirasjonssystemet.
Eksempel.
2,6-dimetyl-4-(4'-cyanofenyl)-l,4-dihydropyridin-3,5-dikar-boksylsyredimetylester.
Man får etter flere timers kokning en oppløs-ning av 10 g 4-cyanbenzaldehyd 16 cm^ aceteddiksyremetylester og 6 cnr ammoniakk i 100 cn<r>metanol, gule krystaller (18 g) av smp. 228°C (metanol).
På samme måte ble det fremstilt:
a) 2,6-dimetyl-4-(3'-cyanofenyl)-l,4-dihydropyridin-3,5-dikarboksylsyredietylester, smp. 152-154°C. b) 2,6-dimetyl-4-(3'-cyano-4'-klorfeny1)-1,4-dihydropyridin-3,5-dikarboksylsyredimetylester av smp. 167°C. c) 2,6-dimetyl-4-(3'-cyanofenyl)-l,4-dihydropyridin-3,5-dikarboksylsyrediisopropylester av smp. 118°C. d) 2,6-dimety1-4-(3'-cyanofenyl)-1,4-dihydropyridin-3,5-dikarboksylsyre-diallylester av smp. 171°C. e) 4-(2'-cyanfenyl)-2,6-dimetyl-l,4-dihydropyridin-dikarbok-sylsyredimetylester av smp. 203°C. f) 4-(2'-cyanfenyl)-2,6-dimetyl-l,4-dihydropyridin-dikarbok-sylsyredietylester av smp. l87°C.
Overlegenheten av forbindelsene ifølge oppfinnelsen er gjengitt eksempelvis i følgende tabell:
Av denne tabell skulle det klart fremgå overlegenheten av forbindelsen ifølge oppfinnelsen.
En "høytrykksrotte" er en rotte, hvor det ved operativt inngrep ble frembragt høyt blodtrykk. Dette så-kalte gullbladhøytrykk frembringes ved innsnevring av nyre- arterien med sølvklips (se også Wilson C. Byrom P.P., i "the Lanzet" 1939, I, side 136-139).
Claims (1)
- Analogi fremgangsmåte" til fremstilling av terapeutisk aktive 1,4-dihydropyridiner med den generelle formel:hvori R' betyr alkyl med 1-4 C-atomer, R" betyr alkyl eller alkenyl med inntil 6 C-atomer, eventuelt cyklisk og/eller eventuelt avbrutt i kjeden irted 1 til 2 oksygenatomer eller substituert med en hydroksygruppe, R"' betyr en nitrilsubstituert fenyl som dessuten kan inneholde en substituent fra gruppen nitril, nitro, hydroksy, acyloksy, alkyl, alkoksy, halogen, amino eller acylamino,karakterisert vedat, i organiske oppløsningsmidler som alkoholer, dioksan, iseddik, dimetylformamid, dimetylsulfoksyd, acetonitril eller i vann ved forhøyet temperatur, overveiende ved oppløsningsmidlets koketemperatur, omsettes aldehyder med den generelle formel hvori R"' har den ovennevnte betydning, med acylfettsyreestere med den generelle formel hvori R' og R" har ovennevnte betydning#og ammoniakk eller ammoniumsalter.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691963188 DE1963188A1 (de) | 1969-12-17 | 1969-12-17 | Neue Cyanphenyl-1,4-dihydropyridinderivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132590B true NO132590B (no) | 1975-08-25 |
| NO132590C NO132590C (no) | 1975-12-03 |
Family
ID=5754097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4730/70A NO132590C (no) | 1969-12-17 | 1970-12-09 |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US3691177A (no) |
| JP (1) | JPS4811102B1 (no) |
| AT (1) | AT301545B (no) |
| BE (1) | BE760483A (no) |
| CA (1) | CA928713A (no) |
| CH (1) | CH559178A5 (no) |
| CS (1) | CS157115B2 (no) |
| DE (1) | DE1963188A1 (no) |
| DK (1) | DK127113B (no) |
| ES (1) | ES386565A1 (no) |
| FI (1) | FI52339C (no) |
| FR (1) | FR2081373B1 (no) |
| GB (1) | GB1305794A (no) |
| IE (1) | IE34742B1 (no) |
| IL (1) | IL35678A (no) |
| NL (1) | NL171052C (no) |
| NO (1) | NO132590C (no) |
| SE (1) | SE364709B (no) |
| ZA (1) | ZA707820B (no) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2005116C3 (de) * | 1970-02-05 | 1980-02-14 | Bayer Ag, 5090 Leverkusen | Symmetrische 1,4-Dihydropyridin-3,5-dicarbonsäureester |
| GB1430961A (en) * | 1972-01-22 | 1976-04-07 | Yamanouchi Pharma Co Ltd | 1-substituted-1,4-dihyddrypyridine derivatives |
| DE2210674C3 (de) * | 1972-03-06 | 1981-09-24 | Bayer Ag, 5090 Leverkusen | 2-Amino-6-methyl-1,4-dihydropyridine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
| US3996234A (en) * | 1972-04-18 | 1976-12-07 | Bayer Aktiengesellschaft | 1,4-Dihydropyridine carboxylic acid esters |
| GB1591089A (en) * | 1976-12-17 | 1981-06-10 | Fujisawa Pharmaceutical Co | 1,4-dihydropyridine derivatives and process for preparation thereof |
| US4338322A (en) * | 1975-07-02 | 1982-07-06 | Fujisawa Pharmaceutical Co., Ltd. | 1,4-Dihydropyridine derivatives, pharmaceutical compositions containing same and methods of effecting vasodilation using same |
| DE3339236A1 (de) * | 1983-10-28 | 1985-05-09 | Bayer Ag | Arzneimittelzubereitung |
| DE4342196A1 (de) * | 1993-12-10 | 1995-06-14 | Bayer Ag | Neue 4-Phenyl-substituierte 1,4-Dihydropyridine |
| US4652573A (en) * | 1985-03-14 | 1987-03-24 | Nelson Research & Development Co. | Calcium antagonist N-hetero ester 1,4-dihydropyridines |
| US4849436A (en) * | 1986-03-11 | 1989-07-18 | Nelson Research & Development Co. | 1,4-dihydropyridines |
| US5216172A (en) * | 1988-02-24 | 1993-06-01 | Ajinomoto Co., Inc. | 1,4-dihydropyridine-4-aryl-2,6-dimethyl-3,5-dicarboxylates useful as agents against drug resistant tumor cells |
| EP0330470A3 (en) * | 1988-02-24 | 1992-01-02 | Ajinomoto Co., Inc. | 1,4-dihydropyridine derivatives useful against tumour cells |
| DE4011695A1 (de) * | 1990-04-11 | 1991-10-17 | Bayer Ag | Verwendung von n-alkylierten 1,4-dihydropyridindicarbonsaeureestern als arzneimittel, neue verbindungen und verfahren zu ihrer herstellung |
| DE4125271A1 (de) * | 1991-07-31 | 1993-02-11 | Bayer Ag | Neue n-alkylierte 1,4-dihydropyridindicarbonsaeureester |
| DE59410255D1 (de) * | 1993-12-10 | 2003-04-17 | Bayer Ag | Phenyl-substituierte 1,4-Dihydropyridine mit cerebraler Aktivität |
| EE03192B1 (et) * | 1993-12-10 | 1999-06-15 | Bayer Aktiengesellschaft | Isopropüül-(2-metoksüetüül)-4-(2-kloro-3-tsüanofenüül)-1,4-dihüdro-2,6-dimetüülpüri diin-3,5-dikarboksülaat, selle enantiomeerid ja vaheühend, meetodid nimetatud ühendite valmistamiseks ja kasutamine |
| FI3511319T3 (fi) | 2014-07-03 | 2023-07-20 | Celgene Quanticel Res Inc | Lysiinispesifisen demetylaasi-1:n inhibiittoreita |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3325505A (en) * | 1965-02-24 | 1967-06-13 | Smith Kline French Lab | 4-cycloalkyl(or cycloalkenyl)-dihydropyridines |
| US3511847A (en) * | 1967-02-07 | 1970-05-12 | Smithkline Corp | 2,6-di-lower alkyl - 1,4-dihydro - 4-(2-trifluoromethylphenyl) - 3,5 - pyridinedicarboxylic acid esters |
| US3441648A (en) * | 1967-02-07 | 1969-04-29 | Smithkline Corp | Compositions and methods for lowering blood pressure with 1,4-dihydropyridines |
| DE1670827C3 (de) * | 1967-03-20 | 1974-10-24 | Bayer Ag, 5090 Leverkusen | 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridin |
| DE1670824C3 (de) * | 1967-03-20 | 1978-08-03 | Bayer Ag, 5090 Leverkusen | 1,4-Dihydropyridin-33-dicarbonsäurealkylester |
| US3455945A (en) * | 1967-06-07 | 1969-07-15 | Smithkline Corp | 4-(carboxy (and carbo-lower alkoxy)phenyl)-1,4-dihydropyridines |
| DE1923990C3 (de) * | 1969-05-10 | 1978-11-23 | Bayer Ag | Verfahren zur Herstellung von N-substituierten M-Dihydropyridin-S.S-dicarbonsäureestern |
-
1969
- 1969-12-17 DE DE19691963188 patent/DE1963188A1/de not_active Ceased
-
1970
- 1970-11-17 IE IE1477/70A patent/IE34742B1/xx unknown
- 1970-11-17 IL IL7035678A patent/IL35678A/xx unknown
- 1970-11-19 ZA ZA707820A patent/ZA707820B/xx unknown
- 1970-11-19 CH CH1711070A patent/CH559178A5/xx not_active IP Right Cessation
- 1970-11-30 FI FI703213A patent/FI52339C/fi active
- 1970-12-04 DK DK619770AA patent/DK127113B/da unknown
- 1970-12-09 NO NO4730/70A patent/NO132590C/no unknown
- 1970-12-10 NL NLAANVRAGE7018070,A patent/NL171052C/xx not_active IP Right Cessation
- 1970-12-11 US US97338A patent/US3691177A/en not_active Expired - Lifetime
- 1970-12-14 AT AT1121570A patent/AT301545B/de not_active IP Right Cessation
- 1970-12-14 CA CA100519A patent/CA928713A/en not_active Expired
- 1970-12-15 JP JP45111391A patent/JPS4811102B1/ja active Pending
- 1970-12-16 SE SE17079/70A patent/SE364709B/xx unknown
- 1970-12-17 FR FR7045676A patent/FR2081373B1/fr not_active Expired
- 1970-12-17 ES ES386565A patent/ES386565A1/es not_active Expired
- 1970-12-17 GB GB6000470A patent/GB1305794A/en not_active Expired
- 1970-12-17 BE BE760483A patent/BE760483A/xx unknown
- 1970-12-17 CS CS855270A patent/CS157115B2/cs unknown
-
1971
- 1971-08-06 US US00169825A patent/US3764683A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CS157115B2 (no) | 1974-08-23 |
| IL35678A (en) | 1974-07-31 |
| US3691177A (en) | 1972-09-12 |
| JPS4811102B1 (no) | 1973-04-10 |
| NL7018070A (no) | 1971-06-21 |
| FI52339C (fi) | 1977-08-10 |
| US3764683A (en) | 1973-10-09 |
| NL171052C (nl) | 1983-02-01 |
| AT301545B (de) | 1972-09-11 |
| NO132590C (no) | 1975-12-03 |
| FI52339B (no) | 1977-05-02 |
| FR2081373B1 (no) | 1975-04-18 |
| IE34742B1 (en) | 1975-08-06 |
| NL171052B (nl) | 1982-09-01 |
| SE364709B (no) | 1974-03-04 |
| CH559178A5 (no) | 1975-02-28 |
| FR2081373A1 (no) | 1971-12-03 |
| CA928713A (en) | 1973-06-19 |
| ZA707820B (en) | 1971-08-25 |
| IE34742L (en) | 1971-06-17 |
| ES386565A1 (es) | 1973-03-16 |
| DK127113B (da) | 1973-09-24 |
| DE1963188A1 (de) | 1971-06-24 |
| BE760483A (fr) | 1971-06-17 |
| IL35678A0 (en) | 1971-01-28 |
| GB1305794A (no) | 1973-02-07 |
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