NL8203260A - Werkwijze ter bereiding van een 1,4-dihydropyridine derivaat. - Google Patents
Werkwijze ter bereiding van een 1,4-dihydropyridine derivaat. Download PDFInfo
- Publication number
- NL8203260A NL8203260A NL8203260A NL8203260A NL8203260A NL 8203260 A NL8203260 A NL 8203260A NL 8203260 A NL8203260 A NL 8203260A NL 8203260 A NL8203260 A NL 8203260A NL 8203260 A NL8203260 A NL 8203260A
- Authority
- NL
- Netherlands
- Prior art keywords
- nitrobenzaldehyde
- dihydropyridine
- diacylate
- preparing
- process according
- Prior art date
Links
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 13
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 claims description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- -1 pyridine Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- COLPLFZHPXIFCQ-UHFFFAOYSA-N 1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=CNC=C(C(O)=O)C1 COLPLFZHPXIFCQ-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 238000003445 Hantzsch reaction Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002927 oxygen compounds Chemical class 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU2005/81A YU41983B (en) | 1981-08-19 | 1981-08-19 | Process for preparing 1,4-dihydro-pyridine derivatives |
| YU200581 | 1981-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8203260A true NL8203260A (nl) | 1983-03-16 |
Family
ID=25556467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8203260A NL8203260A (nl) | 1981-08-19 | 1982-08-19 | Werkwijze ter bereiding van een 1,4-dihydropyridine derivaat. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4467093A (sv) |
| JP (1) | JPS5839663A (sv) |
| AT (1) | AT380876B (sv) |
| CA (1) | CA1185243A (sv) |
| CH (1) | CH651297A5 (sv) |
| DK (1) | DK155734C (sv) |
| ES (1) | ES515063A0 (sv) |
| FI (1) | FI74275C (sv) |
| NL (1) | NL8203260A (sv) |
| PL (1) | PL131222B1 (sv) |
| SE (1) | SE441743B (sv) |
| SU (1) | SU1099842A3 (sv) |
| YU (1) | YU41983B (sv) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4771057A (en) * | 1986-02-03 | 1988-09-13 | University Of Alberta | Reduced pyridyl derivatives with cardiovascular regulating properties |
| JPH02118009U (sv) * | 1989-03-09 | 1990-09-21 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670827C3 (de) * | 1967-03-20 | 1974-10-24 | Bayer Ag, 5090 Leverkusen | 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridin |
| DE2808930A1 (de) * | 1978-03-02 | 1979-09-06 | Bayer Ag | Verfahren zur herstellung von 2-nitrobenzaldehyd |
| JPS554318A (en) * | 1978-06-23 | 1980-01-12 | Asahi Chem Ind Co Ltd | Preparation of 1,4-dihydropyridine |
| JPS5520719A (en) * | 1978-07-31 | 1980-02-14 | Asahi Chem Ind Co Ltd | Preparation of 1,4-dihydropyridine derivative |
| JPS55124760A (en) * | 1979-03-16 | 1980-09-26 | Kanebo Ltd | Preparation of 1,4-dihydropyridine derivative or its salt |
-
1981
- 1981-08-19 YU YU2005/81A patent/YU41983B/xx unknown
-
1982
- 1982-07-27 US US06/402,487 patent/US4467093A/en not_active Expired - Fee Related
- 1982-07-29 CA CA000408333A patent/CA1185243A/en not_active Expired
- 1982-08-11 SE SE8204658A patent/SE441743B/sv not_active IP Right Cessation
- 1982-08-11 AT AT0307082A patent/AT380876B/de not_active IP Right Cessation
- 1982-08-16 FI FI822842A patent/FI74275C/sv not_active IP Right Cessation
- 1982-08-17 CH CH4929/82A patent/CH651297A5/de not_active IP Right Cessation
- 1982-08-17 PL PL1982237935A patent/PL131222B1/pl unknown
- 1982-08-17 ES ES515063A patent/ES515063A0/es active Granted
- 1982-08-18 DK DK370382A patent/DK155734C/da not_active IP Right Cessation
- 1982-08-18 SU SU823482656A patent/SU1099842A3/ru active
- 1982-08-19 NL NL8203260A patent/NL8203260A/nl not_active Application Discontinuation
- 1982-08-19 JP JP57142768A patent/JPS5839663A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE8204658L (sv) | 1983-02-20 |
| FI74275B (fi) | 1987-09-30 |
| SE8204658D0 (sv) | 1982-08-11 |
| YU41983B (en) | 1988-04-30 |
| YU200581A (en) | 1984-02-29 |
| DK370382A (da) | 1983-02-20 |
| US4467093A (en) | 1984-08-21 |
| JPS5839663A (ja) | 1983-03-08 |
| ATA307082A (de) | 1985-12-15 |
| CH651297A5 (de) | 1985-09-13 |
| DK155734B (da) | 1989-05-08 |
| FI822842A0 (fi) | 1982-08-16 |
| CA1185243A (en) | 1985-04-09 |
| FI74275C (sv) | 1988-01-11 |
| AT380876B (de) | 1986-07-25 |
| ES8306364A1 (es) | 1983-06-01 |
| FI822842L (fi) | 1983-02-20 |
| SU1099842A3 (ru) | 1984-06-23 |
| DK155734C (da) | 1989-09-25 |
| ES515063A0 (es) | 1983-06-01 |
| JPS6314709B2 (sv) | 1988-04-01 |
| SE441743B (sv) | 1985-11-04 |
| PL131222B1 (en) | 1984-10-31 |
| PL237935A1 (en) | 1983-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100215702B1 (ko) | 클로로말레이트 또는 클로로푸마레이트 또는 이들의 혼합물로부터 치환 및 비치환 - 2,3 - 피리딘디카르복실레이트의 제조방법 및 이로써 얻어진 피리딘디카르복실레이트 화합물 | |
| CA2044498C (en) | Process for the preparation of dialkyl, pyridine-2,3-dicarboxylates and derivatives thereof from dialkyl dichlorosuccinate | |
| US4600778A (en) | Process for the preparation of 1,4-dihydropyridinedicarboxylic esters | |
| US5099024A (en) | Process for preparation of fluoromethyl-substituted pyridine carbodithioates | |
| KR0130975B1 (ko) | 제초제로서 유용한 o-카르복시아릴이미다졸리논 화합물의 제조방법 | |
| NL8203260A (nl) | Werkwijze ter bereiding van een 1,4-dihydropyridine derivaat. | |
| KR930008234B1 (ko) | 플루오로메틸-치환 디하이드로 피리딘 카보디티오에이트의 제조방법 | |
| EP0371492B1 (en) | Process for the preparation of 1,4-dihydropyridine derivatives | |
| KR950011411B1 (ko) | 피리딘-2,3-디카르복실산의 제조방법 | |
| KR930008230B1 (ko) | 플루오로메틸-치환 피페리딘 카보디티오에이트의 제조방법 | |
| KR930008232B1 (ko) | 플루오로메틸-치환 피리딘 카보디티오에이트의 제조방법 | |
| SU1493104A3 (ru) | Способ получени 5-метилового-3 @ -(N-бензил-N-метиламино)-этилового эфира 2,6-диметил-4-(3Ъ-нитрофенил)-1,4-дигидропиридин-3,5-дикарбоновой кислоты или его сол нокислой соли | |
| EP0142718A1 (en) | Preparation of substituted and unsubstituted 2-((1-carbamoyl-1,2-dimethylpropyl)-carbamoyl)-3-quinolinecarboxylic, nicotinic and benzoic acids | |
| EP0063359B1 (en) | 1,4-dihydropyridine derivatives and processes for preparing the same | |
| US3867437A (en) | N-acyl-N{40 -substituted-2,6-diamino-benzoic acids and process for making the same | |
| KR930008231B1 (ko) | 플루오로메틸-치환 피페리딘 카보디티오에이트의 제조방법 | |
| NL8900569A (nl) | Werkwijze voor de bereiding van 1,4-dihydro-pyridinederivaten. | |
| KR0148125B1 (ko) | 1,4-디하이드로피리딘 카복실산 유도체 및 그의 제조방법 | |
| DE3209081C2 (sv) | ||
| SU1728241A1 (ru) | Способ получени 3,6-дихлор-2-цианопиридина | |
| Katsuyama et al. | A facile synthesis of 2-difluoromethyl-6-methylpyridine-3, 5-dicarboxylates | |
| JPS5916878A (ja) | ２，４−ジヒドロキシ−３−アセチルキノリン類の製造方法 | |
| JP2864653B2 (ja) | ２―ヒドロキシニコチン酸誘導体の製造方法 | |
| JP2816855B2 (ja) | ピリジン―２，３―ジカルボン酸誘導体の製造方法 | |
| KR910005232B1 (ko) | 1,4-디하이드로피리딘 카복실산의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |