KR850001204A - 1,4-디하이드로피리딘 유도체의 제조방법 - Google Patents
1,4-디하이드로피리딘 유도체의 제조방법 Download PDFInfo
- Publication number
- KR850001204A KR850001204A KR1019840004336A KR840004336A KR850001204A KR 850001204 A KR850001204 A KR 850001204A KR 1019840004336 A KR1019840004336 A KR 1019840004336A KR 840004336 A KR840004336 A KR 840004336A KR 850001204 A KR850001204 A KR 850001204A
- Authority
- KR
- South Korea
- Prior art keywords
- general formula
- following general
- group
- nitro
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 4
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title claims 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- QCDJOJKIHZQJGX-UHFFFAOYSA-N 1-nitropropan-2-one Chemical compound CC(=O)C[N+]([O-])=O QCDJOJKIHZQJGX-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- -1 aminocrotonic acid ester Chemical class 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000002772 monosaccharides Chemical class 0.000 claims 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- OYRPMZZLRMIPOM-UHFFFAOYSA-N 3-nitro-4-phenylbut-3-en-2-one Chemical compound CC(=O)C([N+]([O-])=O)=CC1=CC=CC=C1 OYRPMZZLRMIPOM-UHFFFAOYSA-N 0.000 claims 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 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 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 150000002016 disaccharides Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003254 radicals Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Saccharide Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 다음 일반식(II)의 아미노크로톤산 에스테르를 다음 일반식(III)의 벤즈알데히드 및 다음 구조식(1)의 니트로아세톤과 반응시키거나, 다음 일반식(III)의 벤즈알데히드를 다음 일반식(IV)의 아세토 아세트산 에스테르와, 또는 다음 일반식(V)의 그의 크네베나겔 축합반응 생성물을 다음 구조식(2)의 니트로 아세톤 및 암모니아의 부가화합물과 반응시키거나, 다음 일반식(II)의 아미노 크로톤산 에스테르를 다음 일반식(VI)의 벤질리덴니트로아세톤과 반응시킴을 특징으로 하여 다음 일반식(I)의 1,4-디하이드로피리딘유도체 및 그의 약제학적으로 무독한 부가염을 제조하는 방법.상기식에서, R1및 R2는 같거나 다를 수 있으며, 수소, C1내지 C4-알킬, C1내지 C12알콕시, C1내지 C4-할로게노알콕시, 할로겐, 니트로, C1내지 C4-할로게노알킬, C1내지 C4-할로게노 알킬머캡토 또는 그룹 -Z-CH2 또는 -Z-CH2 [여기에서 Z는 산소 또는 황을 나타내고, R4및 R5는 같거나 다를 수 있으며, 수소, C1내지 C4-알킬, C1내지 C6-알콕시, 할로겐, C1내지 C4-할로게노알킬, C1내지 C4-할로게노알콕시 또는 니트로를 나타낸다]중의 하나를 나타내거나 R1및 R2는 페닐고리의 2개의 탄소원자와 함께 고리를 형성하고, X는 산소, 황 또는 라디칼 NR6[여기에서, R6는 C1내지 C6-알킬그룹을 나타낸다]를 나타내고, A는 C2내지 C10-알킬렌그룹 여기에서, 적어도 두 개의 탄소원자는 카복실그룹을 X에 연결시키는 알킬렌 사슬에 위치해야 한다]을 나타내고, R3는 적합하게는 탄수화물 화학에서 통상적인 보호그룹으로 보호된 모노 사카라이드 또는 디사카라이드 잔기를 나타낸다.
- 제1항에 있어서, R1은 수소를 나타내고, R2는 할로겐, 트리플루오로 메틸, 니트로, 수소 또는 그룹 -X-CH2 또는[여기에서, R4및 R5는 제1항에서 정의한 것과 같다] 중의 하나를 나타내고, X는 산소 또는 황을 나타내고, A는 C2내지 C4-알킬렌그룹을 나타내고, R3는 적합하게는 보호그룹으로 보호된 모노사카라이드 잔기를 나타내는 제조방법.
- 제1항에 있어서, 희석제를 사용함을 특징으로 하는 방법.
- 제1항에 있어서, 반응을 20 내지 150℃의 온도에서 수행하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833326384 DE3326384A1 (de) | 1983-07-22 | 1983-07-22 | 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| DEP3326384.1 | 1983-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR850001204A true KR850001204A (ko) | 1985-03-16 |
Family
ID=6204598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004336A KR850001204A (ko) | 1983-07-22 | 1984-07-21 | 1,4-디하이드로피리딘 유도체의 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4537881A (ko) |
| EP (1) | EP0139859B1 (ko) |
| JP (1) | JPS6042393A (ko) |
| KR (1) | KR850001204A (ko) |
| AT (1) | ATE38041T1 (ko) |
| AU (1) | AU564069B2 (ko) |
| CA (1) | CA1229590A (ko) |
| DE (2) | DE3326384A1 (ko) |
| ES (3) | ES534508A0 (ko) |
| GR (1) | GR82104B (ko) |
| HU (1) | HUT36092A (ko) |
| IL (1) | IL72454A (ko) |
| PT (1) | PT78947B (ko) |
| ZA (1) | ZA845626B (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUT39179A (en) * | 1984-12-10 | 1986-08-28 | Sandoz Ag | Process for production of derivatives of 1,4-dihydro-piridin |
| US4868181A (en) * | 1986-08-04 | 1989-09-19 | E. I. Du Pont De Nemours And Company | 1,4-dihydropyridine derivatives with calcium agonist and alpha1 -antagonist activity |
| JPH02167262A (ja) * | 1988-06-05 | 1990-06-27 | Taisho Pharmaceut Co Ltd | １，４―ジヒドロピリジン誘導体 |
| US5166148A (en) * | 1990-07-09 | 1992-11-24 | The Du Pont Merck Pharmaceutical Company | 2-amino-1,4-dihydropyridine derivatives with calcium agonist and alpha1 -antagonist activity |
| GB9119983D0 (en) * | 1991-09-19 | 1991-11-06 | Erba Carlo Spa | Dihydropyridine derivatives useful in antitumor therapy |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2641746C2 (de) * | 1976-09-16 | 1986-11-06 | Bayer Ag, 5090 Leverkusen | 1,4-Dihydropyridin-Zuckerderivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| DE2752820A1 (de) * | 1977-11-26 | 1979-05-31 | Bayer Ag | Neue nitrosubstituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1983
- 1983-07-22 DE DE19833326384 patent/DE3326384A1/de not_active Withdrawn
-
1984
- 1984-07-03 US US06/627,596 patent/US4537881A/en not_active Expired - Fee Related
- 1984-07-09 AT AT84108000T patent/ATE38041T1/de not_active IP Right Cessation
- 1984-07-09 DE DE8484108000T patent/DE3474669D1/de not_active Expired
- 1984-07-09 EP EP84108000A patent/EP0139859B1/de not_active Expired
- 1984-07-19 IL IL72454A patent/IL72454A/xx unknown
- 1984-07-19 PT PT78947A patent/PT78947B/pt unknown
- 1984-07-20 ES ES534508A patent/ES534508A0/es active Granted
- 1984-07-20 HU HU842820A patent/HUT36092A/hu unknown
- 1984-07-20 JP JP59149775A patent/JPS6042393A/ja active Pending
- 1984-07-20 AU AU30887/84A patent/AU564069B2/en not_active Ceased
- 1984-07-20 ZA ZA845626A patent/ZA845626B/xx unknown
- 1984-07-20 GR GR75390A patent/GR82104B/el unknown
- 1984-07-20 CA CA000459310A patent/CA1229590A/en not_active Expired
- 1984-07-21 KR KR1019840004336A patent/KR850001204A/ko not_active Application Discontinuation
-
1985
- 1985-05-31 ES ES543742A patent/ES8604150A1/es not_active Expired
- 1985-05-31 ES ES543741A patent/ES8604149A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0139859B1 (de) | 1988-10-19 |
| ES543741A0 (es) | 1986-01-16 |
| HUT36092A (en) | 1985-08-28 |
| US4537881A (en) | 1985-08-27 |
| ATE38041T1 (de) | 1988-11-15 |
| ES543742A0 (es) | 1986-01-16 |
| CA1229590A (en) | 1987-11-24 |
| ES8602662A1 (es) | 1985-12-01 |
| DE3326384A1 (de) | 1985-01-31 |
| DE3474669D1 (en) | 1988-11-24 |
| PT78947B (en) | 1986-06-02 |
| AU3088784A (en) | 1985-01-24 |
| ES8604150A1 (es) | 1986-01-16 |
| IL72454A (en) | 1987-11-30 |
| EP0139859A3 (en) | 1986-08-20 |
| PT78947A (en) | 1984-08-01 |
| IL72454A0 (en) | 1984-11-30 |
| ZA845626B (en) | 1985-03-27 |
| ES8604149A1 (es) | 1986-01-16 |
| ES534508A0 (es) | 1985-12-01 |
| EP0139859A2 (de) | 1985-05-08 |
| JPS6042393A (ja) | 1985-03-06 |
| AU564069B2 (en) | 1987-07-30 |
| GR82104B (ko) | 1984-12-13 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19840721 |
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| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19890721 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19840721 Comment text: Patent Application |
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| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19910911 Patent event code: PE09021S01D |
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