RU95121073A - 1,4-DIHYDROPYRIDIN-3,5-DICARBONIC ACID DERIVATIVES IN THE FORM OF R- AND S-ISOMERS AND THEIR SALTS, ORIGINAL AND INTERMEDIATE PRODUCTS AND METHOD FOR THEIR PRODUCTION - Google Patents
1,4-DIHYDROPYRIDIN-3,5-DICARBONIC ACID DERIVATIVES IN THE FORM OF R- AND S-ISOMERS AND THEIR SALTS, ORIGINAL AND INTERMEDIATE PRODUCTS AND METHOD FOR THEIR PRODUCTIONInfo
- Publication number
- RU95121073A RU95121073A RU95121073/04A RU95121073A RU95121073A RU 95121073 A RU95121073 A RU 95121073A RU 95121073/04 A RU95121073/04 A RU 95121073/04A RU 95121073 A RU95121073 A RU 95121073A RU 95121073 A RU95121073 A RU 95121073A
- Authority
- RU
- Russia
- Prior art keywords
- general formula
- carbon atoms
- value specified
- unbranched
- formula
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims 5
- 239000011780 sodium chloride Substances 0.000 title claims 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 8
- -1 cyano, ethynyl Chemical group 0.000 claims 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 239000012442 inert solvent Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- YNGDWRXWKFWCJY-UHFFFAOYSA-N dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims 4
- WASQWSOJHCZDFK-UHFFFAOYSA-N Diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000003949 imides Chemical class 0.000 claims 3
- 239000007858 starting material Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- COLPLFZHPXIFCQ-UHFFFAOYSA-N 1,4-dihydropyridine-3,5-dicarboxylic acid Chemical class OC(=O)C1=CNC=C(C(O)=O)C1 COLPLFZHPXIFCQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- XFRBXZCBOYNMJP-UHFFFAOYSA-N 2,2,6-trimethyl-1,3-dioxin-4-one Chemical compound CC1=CC(=O)OC(C)(C)O1 XFRBXZCBOYNMJP-UHFFFAOYSA-N 0.000 claims 1
- 229940085304 Dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N Malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating Effects 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 150000002168 ethanoic acid esters Chemical class 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 229940099690 malic acid Drugs 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- 230000003000 nontoxic Effects 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 0 NC(CC(OC(CC(*1)=O)CC1=O)=O)=O Chemical compound NC(CC(OC(CC(*1)=O)CC1=O)=O)=O 0.000 description 1
Claims (11)
где R1 и R3 одинаковы или различны и означают неразветвленный или разветвленный алкил с 1 - 8 атомами углерода, незамещенный или замещенный неразветвленным или разветвленным алкоксилом с 1 - 6 атомами углерода или гидроксилом, или циклоалкил с 3 - 7 атомами углерода, а
R2 радикал формулы
где R4 и R5 одинаковы или различны и означают галоген, циано, этинил, трифторметокси, метилтио, нитро, трифторметил или неразветвленный или разветвленный алкил, алкенил, алкинил или алкоксил, каждый с 1 - 4 атомами углерода, при этом один из заместителей может означать водород, и их соли.1. Derivatives of 1,4-dihydropyridine-3,5 dicarboxylic acid in the form of R- and S-isomers of the general formula (I)
where R 1 and R 3 are the same or different and denote unbranched or branched alkyl with 1 to 8 carbon atoms, unsubstituted or substituted with unbranched or branched alkoxyl with 1 to 6 carbon atoms or hydroxyl, or cycloalkyl with 3 to 7 carbon atoms, and
R 2 radical of the formula
where R 4 and R 5 are the same or different and mean halogen, cyano, ethynyl, trifluoromethoxy, methylthio, nitro, trifluoromethyl or a straight or branched alkyl, alkenyl, alkynyl or alkoxy, each with 1 to 4 carbon atoms, one of the substituents may mean hydrogen, and their salts.
где R1 и R3 имеют указанное в п.1 значение, или их солей, отличающийся тем, что
а) бензилиденовое соединение общей формулы (II)
где R2 имеют указанное в п.1 значение,
А означает водород, неразветвленный или разветвленный алкил с 1 - 8 атомами углерода или фенил и бензил, незамещенные или замещенные 1 - 3 одинаковыми или различными заместителями из группы, включающей гидроксил, нитро, галоген, циано, карбоксил, трифторметил, трифторметокси, неразветвленный или разветвленный алкоксил с 1 - 6 атомами углерода, группой формулы -NR6R7 или -SO2R8, где
R6 и R7 одинаковы или различны и означают водород, фенил или неразветвленный или разветвленный алкил с 1 - 5 атомами углерода,
R8 означает неразветвленный или разветвленный алкил с 1 - 4 атомами углерода или фенил,
подвергают взаимодействию со сложным эфиром аминокротоновой кислоты общей формулы (III)
где R1 имеет указанное в п.1 значение,
в среде инертных растворителей, в случае необходимости, в присутствии основания, или
б) бензилиденовое соединение общей формулы (IIa)
где R1 и R2 имеют указанные в п.1 значения, подвергают взаимодействию со сложным эфиром аминокротоновой кислоты общей формулы (IIIa)
где А имеет указанное в п.1 значение,
в среде инертных растворителей, в случае необходимости, в присутствии основания, из получаемого согласно пунктам а) или б) 1,4-дигидропиридина общих формул (IVa) и (IVб)
где R1, R2 и А имеют вышеуказанные значения, отщепляют яблочный имид в мягких условиях путем обработки слабыми основаниями с последующим, в случае необходимости, выделением свободной кислоты, кислотную функцию карбоновой кислоты подвергают этерификации по известным методам, а целевой продукт выделяют в свободной форме или в виде соли.2. The method of obtaining derivatives of 1,4-dihydropyridine-3,5-dicarboxylic acid in the form of R - and S-isomers of the General formula (I)
where R 1 and R 3 have the value specified in claim 1, or their salts, characterized in that
a) benzylidene compound of general formula (II)
where R 2 have the value specified in claim 1,
And means hydrogen, unbranched or branched alkyl with 1 to 8 carbon atoms or phenyl and benzyl, unsubstituted or substituted with 1 to 3 identical or different substituents from the group including hydroxyl, nitro, halogen, cyano, carboxyl, trifluoromethyl, trifluoromethoxy, unbranched or branched alkoxy with 1 to 6 carbon atoms, a group of the formula —NR 6 R 7 or —SO 2 R 8 , wherein
R 6 and R 7 are the same or different and denote hydrogen, phenyl or unbranched or branched alkyl with 1 to 5 carbon atoms,
R 8 means unbranched or branched alkyl with 1 to 4 carbon atoms or phenyl,
reacted with aminocrotonic acid ester of the general formula (III)
where R 1 has the value specified in claim 1,
in inert solvents, if necessary, in the presence of a base, or
b) benzylidene compound of general formula (IIa)
where R 1 and R 2 have the values indicated in claim 1, are reacted with aminocrotonic acid ester of the general formula (IIIa)
where a has the value specified in claim 1,
in inert solvents, if necessary, in the presence of a base, from 1,4-dihydropyridine obtained according to a) or b) of the general formulas (IVa) and (IVb)
where R 1 , R 2 and A are as defined above, the apple imide is cleaved under mild conditions by treatment with weak bases followed by, if necessary, liberation of the free acid, the acidic function of the carboxylic acid is subjected to esterification by known methods, and the target product is isolated in free form or in the form of salt.
где R2 имеет указанное в п.1 значение,
А означает водород, неразветвленный или разветвленный алкил с 1 - 8 атомами углерода или фенил и бензил, незамещенные или замещенные 1 - 3 одинаковыми или различными заместителями из группы, включающей гидроксил, нитро, галоген, циано, карбоксил, трифторметил, трифторметокси, неразветвленный или разветвленный алкоксил с 1 - 6 атомами углерода, группой формулы -NR6R7 или -SO2R8, где
R6 и R7 одинаковы или различны и означают водород, фенил или неразветвленный или разветвленный алкил с 1 - 5 атомами углерода, и
R8 означает неразветвленный или разветвленный алкил с 1 - 4 атомами углерода или фенил,
в качестве исходного продукта для получения соединений формулы (I).3. Benzylidene compounds of General formula (II)
where R 2 has the value specified in claim 1,
And means hydrogen, unbranched or branched alkyl with 1 to 8 carbon atoms or phenyl and benzyl, unsubstituted or substituted with 1 to 3 identical or different substituents from the group including hydroxyl, nitro, halogen, cyano, carboxyl, trifluoromethyl, trifluoromethoxy, unbranched or branched alkoxy with 1 to 6 carbon atoms, a group of the formula —NR 6 R 7 or —SO 2 R 8 , wherein
R 6 and R 7 are the same or different and are hydrogen, phenyl or straight or branched alkyl with 1-5 carbon atoms, and
R 8 means unbranched or branched alkyl with 1 to 4 carbon atoms or phenyl,
as a starting material for the preparation of compounds of formula (I).
R2-CHO,
где R2 имеет указанное в п.1 значение, подвергают взаимодействию со сложным эфиром ацетуксусной кислоты общей формулы (VI)
где А имеет указанное в п.2 значение,
в среде инертных растворителей и в присутствии основания и карбоновой кислоты.4. The method of obtaining benzylidene compounds of General formula (II) under item 3, characterized in that the aldehyde of General formula (V)
R 2 -CHO,
where R 2 has the value specified in claim 1, is reacted with acetic acid ester of the general formula (VI)
where A has the value specified in item 2,
in inert solvents and in the presence of base and carboxylic acid.
где А имеет указанное в п.3 значение,
в качестве исходного продукта для получения соединений формулы (I).5. Aminocrotonic ester as R or S isomers of the general formula (IIIa)
where A has the value specified in paragraph 3,
as a starting material for the preparation of compounds of formula (I).
где А имеет указанное в п.3 значение,
подвергают взаимодействию с дикетеном или аддуктом дикетена и ацетона в среде инертных растворителей при 50 - 120oС, после чего ин ситу добавляют аммиак или аммониевые соли.6. A method of producing an aminocrotonic ester of the general formula (IIIa) according to claim 5, characterized in that the imide of malic acid of the general formula (VII)
where A has the value specified in paragraph 3,
interact with diketene or adduct of diketene and acetone in inert solvents at 50–120 o С, after which the ammonia or ammonium salts are added in sieve.
где А имеет указанное в п.3 значение,
в качестве исходного продукта для получения соединений формулы (I) по п. 1.7. Esters of acetic acid of general formula (VI)
where A has the value specified in paragraph 3,
as a starting material for the preparation of compounds of formula (I) according to claim 1.
где А имеет указанное в п.3 значение,
подвергают взаимодействию с дикетеном или аддуктом диктена и ацетона, 2,2,6-триметил-1,3-диоксин-4-оном, в среде инертных растворителей.8. The method of obtaining the ester acetic acid of General formula (VI), characterized in that the imide (S) - or (R) -blocker acid of General formula (VII)
where A has the value specified in paragraph 3,
subjected to interaction with diketene or adduct of dictene and acetone, 2,2,6-trimethyl-1,3-dioxin-4-one, in an inert solvent.
где R1 и R2 имеют указанные в п.1 значения, а А имеет указанное в п.3 значение,
в качестве промежуточных продуктов для получения соединений формулы (I).9. 1,4-Dihydropyridines of the general formulas (IVa) and (IVb)
where R 1 and R 2 have the values indicated in paragraph 1, and A has the meaning specified in paragraph 3,
as intermediates for the preparation of compounds of formula (I).
где R1 - R3 имеют указанные в п.1 значения, или его соль в эффективном количестве.11. Pharmaceutical composition containing an active principle based on dihydropyridine derivatives and at least one non-toxic pharmaceutically acceptable carrier, characterized in that it contains as active principle a compound of general formula (I)
where R 1 - R 3 have the values indicated in paragraph 1, or its salt in an effective amount.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4443168.6 | 1994-12-05 | ||
| DE4443168A DE4443168A1 (en) | 1994-12-05 | 1994-12-05 | New highly selective process for the production of enantiomerically pure phenyl-substituted 1,4-dihydropyridine-3,5-dicarboxylic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU95121073A true RU95121073A (en) | 1997-11-27 |
| RU2155752C2 RU2155752C2 (en) | 2000-09-10 |
Family
ID=6534908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU95121073/04A RU2155752C2 (en) | 1994-12-05 | 1995-12-05 | Methods for preparation of 1,4-dihydropyridine-3,5-dicarboxylic acid derivatives in the form of r isomers and their salts, starting substances and intermediates for preparation thereof |
Country Status (27)
| Country | Link |
|---|---|
| US (4) | US5700948A (en) |
| EP (2) | EP0716081B1 (en) |
| JP (1) | JP3891500B2 (en) |
| KR (1) | KR100396011B1 (en) |
| CN (5) | CN1079793C (en) |
| AT (1) | ATE322482T1 (en) |
| AU (1) | AU702274B2 (en) |
| CA (1) | CA2164276C (en) |
| CZ (1) | CZ296438B6 (en) |
| DE (2) | DE4443168A1 (en) |
| DK (1) | DK0716081T3 (en) |
| ES (1) | ES2262138T3 (en) |
| FI (1) | FI115908B (en) |
| HU (1) | HU214683B (en) |
| IL (1) | IL116225A (en) |
| MX (1) | MX9504954A (en) |
| MY (1) | MY112938A (en) |
| NO (1) | NO312832B1 (en) |
| NZ (1) | NZ280578A (en) |
| PL (1) | PL183604B1 (en) |
| PT (1) | PT716081E (en) |
| RU (1) | RU2155752C2 (en) |
| SG (1) | SG73352A1 (en) |
| SI (1) | SI0716081T1 (en) |
| SK (1) | SK282428B6 (en) |
| TW (1) | TW310324B (en) |
| ZA (1) | ZA9510263B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102533154B1 (en) | 2022-09-22 | 2023-05-17 | 임태형 | Stair safety railing bar |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932646A (en) * | 1971-04-10 | 1976-01-13 | Farbenfabriken Bayer Ag | Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylate |
| JPS6058239B2 (en) * | 1978-07-20 | 1985-12-19 | 山之内製薬株式会社 | New cephalosporin derivatives |
| DE2911029C2 (en) * | 1979-03-21 | 1985-03-14 | Kombi-Lift Montage- Und Handelsgesellschaft Mbh, 5650 Solingen | Device for holding the guide rollers for the load ropes of a facade rope elevator in a housing fixed on top of the building |
| GR850872B (en) * | 1984-04-16 | 1985-11-25 | Yamanouchi Pharma Co Ltd | |
| US4539302A (en) * | 1984-04-30 | 1985-09-03 | E. I. Du Pont De Nemours And Company | Recovery of zerovalent nickel complexes |
| DE3423105A1 (en) * | 1984-06-22 | 1986-01-02 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING OPTICALLY ACTIVE 1,4-DIHYDROPYRIDINE |
-
1994
- 1994-12-05 DE DE4443168A patent/DE4443168A1/en not_active Withdrawn
-
1995
- 1995-11-16 MY MYPI95003487A patent/MY112938A/en unknown
- 1995-11-17 TW TW084112189A patent/TW310324B/zh active
- 1995-11-22 EP EP95118359A patent/EP0716081B1/en not_active Expired - Lifetime
- 1995-11-22 PT PT95118359T patent/PT716081E/en unknown
- 1995-11-22 AT AT95118359T patent/ATE322482T1/en active
- 1995-11-22 ES ES95118359T patent/ES2262138T3/en not_active Expired - Lifetime
- 1995-11-22 SI SI9530725T patent/SI0716081T1/en unknown
- 1995-11-22 DE DE59511043T patent/DE59511043D1/en not_active Expired - Lifetime
- 1995-11-22 DK DK95118359T patent/DK0716081T3/en active
- 1995-11-22 EP EP04009787A patent/EP1443043A3/en not_active Withdrawn
- 1995-11-28 US US08/563,725 patent/US5700948A/en not_active Ceased
- 1995-11-28 MX MX9504954A patent/MX9504954A/en unknown
- 1995-11-29 AU AU39150/95A patent/AU702274B2/en not_active Ceased
- 1995-11-30 PL PL95311539A patent/PL183604B1/en not_active IP Right Cessation
- 1995-12-01 NO NO19954885A patent/NO312832B1/en not_active IP Right Cessation
- 1995-12-01 JP JP33570795A patent/JP3891500B2/en not_active Expired - Fee Related
- 1995-12-01 CA CA002164276A patent/CA2164276C/en not_active Expired - Fee Related
- 1995-12-01 NZ NZ280578A patent/NZ280578A/en not_active IP Right Cessation
- 1995-12-01 HU HU9503438A patent/HU214683B/en not_active IP Right Cessation
- 1995-12-01 IL IL11622595A patent/IL116225A/en not_active IP Right Cessation
- 1995-12-04 ZA ZA9510263A patent/ZA9510263B/en unknown
- 1995-12-04 SK SK1526-95A patent/SK282428B6/en not_active IP Right Cessation
- 1995-12-04 CZ CZ0320595A patent/CZ296438B6/en not_active IP Right Cessation
- 1995-12-04 KR KR1019950046341A patent/KR100396011B1/en not_active IP Right Cessation
- 1995-12-04 FI FI955825A patent/FI115908B/en not_active IP Right Cessation
- 1995-12-04 SG SG1995002018A patent/SG73352A1/en unknown
- 1995-12-05 RU RU95121073/04A patent/RU2155752C2/en not_active IP Right Cessation
- 1995-12-05 CN CN95119057A patent/CN1079793C/en not_active Expired - Fee Related
-
1997
- 1997-07-16 US US08/896,275 patent/US5849924A/en not_active Expired - Lifetime
-
1998
- 1998-09-21 US US09/158,428 patent/US5910593A/en not_active Expired - Lifetime
-
1999
- 1999-03-25 US US09/276,220 patent/USRE36607E/en not_active Expired - Lifetime
- 1999-12-30 CN CN991275276A patent/CN1216054C/en not_active Expired - Fee Related
- 1999-12-30 CN CN99127530A patent/CN1094926C/en not_active Expired - Fee Related
- 1999-12-30 CN CN99127528A patent/CN1094486C/en not_active Expired - Fee Related
- 1999-12-30 CN CN99127529A patent/CN1105102C/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU518127A3 (en) | Method for preparing basic 1,4-dihydropyridinecarboxylic esters or their salts | |
| DE1923990C3 (en) | Process for the preparation of N-substituted M-dihydropyridine-S.S-dicarboxylic acid esters | |
| KR910006254A (en) | Oxazole- and Thiazole Carboxamides | |
| OGAWA et al. | Synthesis and antihypertensive activities of new 1, 4-dihydropyridine derivatives containing a nitrooxy moiety at the 3-ester position | |
| MX9708662A (en) | A process for the preparation of lercanidipine hydrochloride. | |
| US4600778A (en) | Process for the preparation of 1,4-dihydropyridinedicarboxylic esters | |
| RU95121073A (en) | 1,4-DIHYDROPYRIDIN-3,5-DICARBONIC ACID DERIVATIVES IN THE FORM OF R- AND S-ISOMERS AND THEIR SALTS, ORIGINAL AND INTERMEDIATE PRODUCTS AND METHOD FOR THEIR PRODUCTION | |
| Ogawa et al. | Mild and facile cleavage of 2-cyanoethyl ester using sodium sulfide or tetrabutylammonium fluoride. Synthesis of 1, 4-dihydropyridine monocarboxylic acids and unsymmetrical 1, 4-dihydropyridine dicarboxylates | |
| US5367081A (en) | 1,4-dihydropyridine derivatives | |
| EP0225574B1 (en) | Novel 1,4-dihydropyridines containing fluorine, process for their preparation and their use as medicaments | |
| RU2161156C1 (en) | Method of preparing 3-ethyl-5-methyl ester of 2-[2-n-(phthalimido)ethoxymethyl]- 4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid | |
| JPH0635438B2 (en) | Process for producing optically active 1,4-dihydropyridines | |
| CZ285313B6 (en) | Process for preparing dimethyl-1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate | |
| JPH04211060A (en) | Novel production of 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic-3-methyl ester-5-beta-(n-venzyl-n-methylamino)ethyl ester | |
| US6015906A (en) | Dimethylamine benzoate or p-anisate catalysed process for the preparation of 4-(nitrophenyl)-dihydropyridines | |
| KR910700246A (en) | Imidazolyl and pyridyl derivatives of phenyl substituted 1,4-dihydro-pyridine and preparation methods thereof | |
| FI74275B (en) | PROCEDURE FOR FRAMSTAELLNING AV 4- (2'-NITROPHENYL) -2,6-DIMETHYL-3,5-DIMETOXICARBONYL-1,4-DIHYDRO-PYRIDINE. | |
| JPH07126251A (en) | Production of 1,4-dihydropyridinemonocarboxylic acid | |
| SU383290A1 (en) | METHOD FOR OBTAINING 1,4-DIHYDROPYRIDINE DERIVATIVES.12 | |
| CA2164276C (en) | New highly selective process for the preparation of enantiomerically pure phenylsubstituted 1,4-dihydropyridine-3,5-dicarboxylic acid derivatives | |
| JPS5585563A (en) | Preparation of novel 1,4-dihydropridine-3,5-dicarboxylic acid aminoalkyl ester derivative | |
| Khadilkar et al. | Synthesis and pharmacological studies of new derivatives of dimethyl 1, 4-dihydro-2, 6-dimethyl-3, 5-pyridinedicarboxylate | |
| HU193786B (en) | Process for producing dihydropyridine derivatives | |
| CS243590B1 (en) | Method of-aryl-2,6-dimethyl-1,4-didhydropyridine-3,5-dicarboxyl acid's diesters preparation | |
| US5696268A (en) | 1, 4-Dihydropyridine derivatives and methods of producing the same |