IL34304A - Process for the production of n-substituted 1,4-dihydro-3,5-pyridine dicarboxyylic acid esters - Google Patents
Process for the production of n-substituted 1,4-dihydro-3,5-pyridine dicarboxyylic acid estersInfo
- Publication number
- IL34304A IL34304A IL34304A IL3430470A IL34304A IL 34304 A IL34304 A IL 34304A IL 34304 A IL34304 A IL 34304A IL 3430470 A IL3430470 A IL 3430470A IL 34304 A IL34304 A IL 34304A
- Authority
- IL
- Israel
- Prior art keywords
- pyridine
- ester
- acid
- dihydropyridine
- substituted
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 25
- 150000002148 esters Chemical class 0.000 title description 9
- -1 N-substituted-1,4-dihydropyridines Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052736 halogen Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 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
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 21
- 239000013078 crystal Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000005457 ice water Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- SXVRSCIZJBGJGB-UHFFFAOYSA-N 1-chloropropan-2-ylbenzene Chemical compound ClCC(C)C1=CC=CC=C1 SXVRSCIZJBGJGB-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- HETBKLHJEWXWBM-UHFFFAOYSA-N 4-chloro-3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC(C=O)=CC=C1Cl HETBKLHJEWXWBM-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- JHKOMVRNWGLUFA-UHFFFAOYSA-N dipropan-2-yl pyridine-3,5-dicarboxylate Chemical compound CC(C)OC(=O)C1=CN=CC(C(=O)OC(C)C)=C1 JHKOMVRNWGLUFA-UHFFFAOYSA-N 0.000 description 1
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- CJJZCWJJAZMVCJ-UHFFFAOYSA-N n-benzyl-2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(NCC=2C=CC=CC=2)=C1 CJJZCWJJAZMVCJ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- 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
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1923990A DE1923990C3 (de) | 1969-05-10 | 1969-05-10 | Verfahren zur Herstellung von N-substituierten M-Dihydropyridin-S.S-dicarbonsäureestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL34304A0 IL34304A0 (en) | 1970-06-17 |
| IL34304A true IL34304A (en) | 1973-06-29 |
Family
ID=5733869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL34304A IL34304A (en) | 1969-05-10 | 1970-04-13 | Process for the production of n-substituted 1,4-dihydro-3,5-pyridine dicarboxyylic acid esters |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3773773A (OSRAM) |
| JP (1) | JPS4935277B1 (OSRAM) |
| AT (1) | AT299200B (OSRAM) |
| BE (1) | BE750139A (OSRAM) |
| BR (1) | BR6915159D0 (OSRAM) |
| DE (1) | DE1923990C3 (OSRAM) |
| DK (1) | DK136246B (OSRAM) |
| FI (1) | FI52078C (OSRAM) |
| FR (1) | FR2051515B1 (OSRAM) |
| GB (1) | GB1305793A (OSRAM) |
| IL (1) | IL34304A (OSRAM) |
| NL (1) | NL7006628A (OSRAM) |
| NO (1) | NO133274C (OSRAM) |
| SE (1) | SE376915B (OSRAM) |
| YU (1) | YU33268B (OSRAM) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1963188A1 (de) * | 1969-12-17 | 1971-06-24 | Bayer Ag | Neue Cyanphenyl-1,4-dihydropyridinderivate |
| DE2117572C3 (de) * | 1971-04-10 | 1980-03-20 | Bayer Ag, 5090 Leverkusen | Unsymmetrische 1,4-Dihydropyridin ^-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| DE2117571C3 (de) * | 1971-04-10 | 1979-10-11 | Bayer Ag, 5090 Leverkusen | Unsymmetrische 1,4-Dihydropyridin-33-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| GB1430961A (en) * | 1972-01-22 | 1976-04-07 | Yamanouchi Pharma Co Ltd | 1-substituted-1,4-dihyddrypyridine derivatives |
| US4021434A (en) * | 1972-01-22 | 1977-05-03 | Yamanouchi Pharmaceutical Co., Ltd. | Sodium β-[2,6-dimethyl-3,5-bis(ethoxycarbonyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-1-yl]ethyl sulfate |
| US3857849A (en) * | 1973-02-28 | 1974-12-31 | Bayer Ag | 2-amino-1,4-dihydropyridine 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 |
| US3992545A (en) * | 1972-03-06 | 1976-11-16 | Bayer Aktiengesellschaft | 2-Amino-4,5-dihydropyridine derivatives in pharmaceutical compositions |
| US3985886A (en) * | 1972-03-06 | 1976-10-12 | Bayer Aktiengesellschaft | 2-Amino-4,5-dihydropyridine derivatives and process for their preparation |
| US3939171A (en) * | 1972-03-06 | 1976-02-17 | Bayer Aktiengesellschaft | 2-Amino-1,4-dihydropyridine derivatives |
| DD106832A5 (OSRAM) * | 1972-03-06 | 1974-07-05 | ||
| US3917620A (en) * | 1972-03-06 | 1975-11-04 | Bayer Ag | 2-Amino-4,5-dihydropyridine derivatives |
| US3957998A (en) * | 1972-03-06 | 1976-05-18 | Bayer Aktiengesellschaft | Use of 2,6-diamino-4-substituted-1,4-dihydropyridine-3,5-dicarboxylic acid esters for effecting coronary vessel dilation and treating hypertension |
| US3887558A (en) * | 1972-03-06 | 1975-06-03 | Bayer Ag | Process for producing 2,6-diamino -1,4- dihydro-3,5-pyridine-dicarboxylates and derivatives thereof |
| US3935223A (en) * | 1972-03-06 | 1976-01-27 | Bayer Aktiengesellschaft | 2-Amino-1,4-dihydropyridine derivatives |
| US3988458A (en) * | 1972-03-06 | 1976-10-26 | Bayer Aktiengesellschaft | Bicyclic derivatives of 1,4-dihydropyridine 3,5-carboxylic acid esters |
| US3933834A (en) * | 1972-03-06 | 1976-01-20 | Bayer Aktiengesellschaft | Unsymmetrical esters of N-substituted 1,4-dihydropyridine 3,5-dicarboxylic acid |
| DE2218644C3 (de) * | 1972-04-18 | 1982-08-19 | Bayer Ag, 5090 Leverkusen | Basische Ester von 1,4-Dihydropyridinen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| US3968117A (en) * | 1972-06-10 | 1976-07-06 | Bayer Aktiengesellschaft | 1,4-Dihydropyridines |
| DE2228363A1 (de) * | 1972-06-10 | 1974-01-03 | Bayer Ag | 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2239815C2 (de) * | 1972-08-12 | 1983-02-10 | Bayer Ag, 5090 Leverkusen | 2-Alkylamino-dihydropyridine, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel |
| US4136187A (en) * | 1972-08-12 | 1979-01-23 | Bayer Aktiengesellschaft | Antihypertensive 2-amino-4,5-dihydropyridine derivatives |
| DE2242786A1 (de) * | 1972-08-31 | 1974-03-14 | Bayer Ag | Verfahren zur herstellung von neuen 2-amino-1,4-dihydropyridinen mit einer carbonylfunktion sowie ihre verwendung als arzneimittel |
| DE2242787C2 (de) * | 1972-08-31 | 1982-01-21 | Bayer Ag, 5090 Leverkusen | 4-Phenyl-6-amino-3,4-dihydropyridon-(2)-3,5-dicarbonsäure-diäthylesterderivate, ein Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| GB1409865A (en) * | 1973-02-13 | 1975-10-15 | Science Union & Cie | Dihydropyridines derivatives their preparation and pharmaceu tical compositions containing them |
| FR2218107A1 (en) * | 1973-02-20 | 1974-09-13 | Yamanouchi Pharma Co Ltd | Amino alkyl 2,6-dialkyl-4-aryl-1,4 dihydropyridine-3, carboxylates - useful as cerebral vasodilators and musculotropic spasmolytic agents |
| US4002762A (en) * | 1973-03-03 | 1977-01-11 | Bayer Aktiengesellschaft | 2-Amino-3,4-dihydropyridines used to effect coronary vessel dilation and treat hypertension |
| GB1425729A (en) * | 1973-06-12 | 1976-02-18 | Smith Kline French Lab | 1,4-dihydropyridine compounds |
| US4020178A (en) * | 1973-07-12 | 1977-04-26 | Bayer Aktiengesellschaft | 1,4-Dihydropyridine esters used as coronary dilators and anti-hypertensives |
| DE2335466A1 (de) * | 1973-07-12 | 1975-01-30 | Bayer Ag | Alkoxyalkyl-1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| FR2320750A1 (fr) * | 1975-08-12 | 1977-03-11 | Hexachimie | Dihydro-1,4 pyridines et leur application therapeutique |
| US4466972A (en) * | 1977-06-20 | 1984-08-21 | Sandoz Ltd. | Benzoxadiazoles and benzothiadiazoles, their preparation and pharmaceutical compositions containing them |
| DE2738153A1 (de) * | 1977-08-24 | 1979-03-08 | Bayer Ag | 2-pyridyl-1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| FR2405937A1 (fr) * | 1977-10-14 | 1979-05-11 | Labaz | Nouveaux derives de dihydropyridine, leur procede de preparation et leur application |
| SU798099A1 (ru) * | 1978-03-06 | 1981-01-23 | Ордена Трудового Красного Знамениинститут Органического Синтезаан Латвийской Ccp | 1-Бензил-2,6-диметил-4-о-или-M-НиТРОфЕНил-3,5-диэТОКСиКАРбОНил- 1,4-дигидРОпиРидиНы, пРО Вл ющиЕКОРОНАРОдилАТиРующую АКТиВНОСТь |
| DE3022030A1 (de) * | 1980-06-12 | 1981-12-17 | Bayer Ag, 5090 Leverkusen | 4-thiazol- bzw. 4-imidazol-substituierte, 1,4-dihydropyridine, verfahren zu deren herstellung sowie diese enthaltende arzneimittel |
| US4321384A (en) * | 1981-02-27 | 1982-03-23 | American Home Products Corporation | Antihypertensive agents |
| US4365063A (en) * | 1981-08-31 | 1982-12-21 | American Home Products Corporation | Antihypertensive agents |
| NZ201395A (en) * | 1981-07-30 | 1987-02-20 | Bayer Ag | Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines |
| JPS58159490A (ja) * | 1982-02-23 | 1983-09-21 | Nikken Kagaku Kk | １，４−ジヒドロピリジン化合物 |
| US4500532A (en) * | 1983-03-03 | 1985-02-19 | Usv Pharmaceutical Corporation | 1-(Substituted aminoalkyl)-1,4-dihydropyridines |
| US4771057A (en) * | 1986-02-03 | 1988-09-13 | University Of Alberta | Reduced pyridyl derivatives with cardiovascular regulating properties |
| EP0388482B1 (de) * | 1989-03-20 | 1994-07-06 | Siemens Aktiengesellschaft | Lichtempfindliches Gemisch |
| US5258521A (en) * | 1989-07-26 | 1993-11-02 | Tosoh Corporation | Process of producing optically active propionic acid ester derivatives |
| 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 |
| DE4133257A1 (de) * | 1991-10-08 | 1993-04-15 | Bayer Ag | N-methyl-nimodipin, verfahren zu seiner herstellung und seine verwendung als zerebraltherapeutikum |
| DE4223867A1 (de) * | 1992-07-20 | 1994-01-27 | Bayer Ag | Spezieller 1,4-Dihydropyridin-3,5-dicarbonsäureester, Verfahren zu seiner Herstellung und seine pharmazeutische Verwendung |
| DE4430094A1 (de) * | 1994-08-25 | 1996-02-29 | Bayer Ag | Verwendung von 3,5-Dicarbonsäureester-1,4-Dihydropyridinen als Arzneimittel |
| JPH1039510A (ja) * | 1996-07-29 | 1998-02-13 | Nitto Denko Corp | ネガ型フォトレジスト組成物及びその利用 |
| EP1043998B1 (en) * | 1997-12-13 | 2007-03-07 | Bristol-Myers Squibb Company | USE OF PYRAZOLO [3,4-b] PYRIDINE AS CYCLIN DEPENDANT KINASE INHIBITORS |
| US6653481B2 (en) * | 2000-12-29 | 2003-11-25 | Synthon Bv | Process for making amlodipine |
| CA2854252C (en) * | 2011-11-24 | 2016-11-29 | Lipidart Kutato Fejleszto Es Tanacsado Kft. | 1,4-dihydropyridine derivatives with hsp modulating activity |
Family Cites Families (2)
| 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 |
| US3441648A (en) * | 1967-02-07 | 1969-04-29 | Smithkline Corp | Compositions and methods for lowering blood pressure with 1,4-dihydropyridines |
-
1969
- 1969-05-10 DE DE1923990A patent/DE1923990C3/de not_active Expired
- 1969-12-15 BR BR215159/69A patent/BR6915159D0/pt unknown
-
1970
- 1970-04-13 IL IL34304A patent/IL34304A/en unknown
- 1970-04-20 YU YU1026/70A patent/YU33268B/xx unknown
- 1970-04-21 GB GB1902770A patent/GB1305793A/en not_active Expired
- 1970-04-27 SE SE7005793A patent/SE376915B/xx unknown
- 1970-05-04 DK DK224370AA patent/DK136246B/da unknown
- 1970-05-04 NO NO1683/70A patent/NO133274C/no unknown
- 1970-05-04 JP JP45037598A patent/JPS4935277B1/ja active Pending
- 1970-05-05 FI FI701259A patent/FI52078C/fi active
- 1970-05-06 NL NL7006628A patent/NL7006628A/xx unknown
- 1970-05-06 AT AT409470A patent/AT299200B/de not_active IP Right Cessation
- 1970-05-08 BE BE750139D patent/BE750139A/xx unknown
- 1970-05-08 FR FR707016863A patent/FR2051515B1/fr not_active Expired
-
1971
- 1971-11-22 US US00201152A patent/US3773773A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2051515A1 (OSRAM) | 1971-04-09 |
| DE1923990B2 (de) | 1978-03-30 |
| NO133274B (OSRAM) | 1975-12-29 |
| FI52078C (fi) | 1977-06-10 |
| US3773773A (en) | 1973-11-20 |
| DE1923990C3 (de) | 1978-11-23 |
| JPS4935277B1 (OSRAM) | 1974-09-20 |
| FI52078B (OSRAM) | 1977-02-28 |
| NO133274C (OSRAM) | 1976-04-07 |
| YU102670A (en) | 1976-03-31 |
| AT299200B (de) | 1972-06-12 |
| GB1305793A (OSRAM) | 1973-02-07 |
| IL34304A0 (en) | 1970-06-17 |
| BR6915159D0 (pt) | 1973-04-19 |
| NL7006628A (OSRAM) | 1970-11-12 |
| SE376915B (OSRAM) | 1975-06-16 |
| DK136246C (OSRAM) | 1978-02-13 |
| FR2051515B1 (OSRAM) | 1974-07-12 |
| DK136246B (da) | 1977-09-12 |
| BE750139A (OSRAM) | 1970-11-09 |
| DE1923990A1 (de) | 1970-11-19 |
| YU33268B (en) | 1976-08-31 |
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