JPH0369910B2 - - Google Patents
Info
- Publication number
- JPH0369910B2 JPH0369910B2 JP54163965A JP16396579A JPH0369910B2 JP H0369910 B2 JPH0369910 B2 JP H0369910B2 JP 54163965 A JP54163965 A JP 54163965A JP 16396579 A JP16396579 A JP 16396579A JP H0369910 B2 JPH0369910 B2 JP H0369910B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- compounds
- residue
- administered
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000017531 blood circulation Effects 0.000 description 3
- 210000004351 coronary vessel Anatomy 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000004005 microsphere Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010022562 Intermittent claudication Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002213 calciumantagonistic effect Effects 0.000 description 2
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 2
- 208000021156 intermittent vascular claudication Diseases 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZYXNLVMBIHVDRH-UHFFFAOYSA-N 2-Methylpropyl 3-oxobutanoate Chemical compound CC(C)COC(=O)CC(C)=O ZYXNLVMBIHVDRH-UHFFFAOYSA-N 0.000 description 1
- -1 4-(2,1,3-benzoxadiazole- 4-yl)-2,6-dimethyl-1,4-dihydro-3-methoxycarbonyl-pyridine-5 -Carboxylic acid isobutyl ester 2,1,3-benzoxadiazole-4-aldehyde Chemical compound 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect 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
- 230000037396 body weight Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003727 cerebral blood flow Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000002999 depolarising effect Effects 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1283578A CH639659A5 (de) | 1978-12-18 | 1978-12-18 | Neue 1,4-dihydropyridinderivate, deren herstellung und verwendung. |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5583783A JPS5583783A (en) | 1980-06-24 |
JPH0369910B2 true JPH0369910B2 (es) | 1991-11-05 |
Family
ID=4386824
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16396579A Granted JPS5583783A (en) | 1978-12-18 | 1979-12-17 | 1*44dihydropyridine derivative |
Country Status (18)
Country | Link |
---|---|
JP (1) | JPS5583783A (es) |
AU (1) | AU536055B2 (es) |
BE (1) | BE880591A (es) |
CH (1) | CH639659A5 (es) |
CY (1) | CY1321A (es) |
DE (1) | DE2949491A1 (es) |
FR (1) | FR2444681A1 (es) |
GB (2) | GB2037766B (es) |
HK (1) | HK16086A (es) |
IE (1) | IE49496B1 (es) |
IT (1) | IT1164097B (es) |
KE (1) | KE3593A (es) |
MY (1) | MY8500130A (es) |
NL (2) | NL193066C (es) |
NZ (1) | NZ192422A (es) |
SE (1) | SE445219B (es) |
SG (1) | SG97585G (es) |
ZA (1) | ZA796842B (es) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
CH655658B (es) * | 1980-09-18 | 1986-05-15 | ||
EP0080220B1 (en) * | 1981-11-17 | 1986-02-19 | FISONS plc | Dihydropyridines, methods for their production and their formulation and use as pharmaceuticals |
ZA83959B (en) * | 1982-03-10 | 1984-09-26 | Sandoz Ltd | 1,4-dihydropyridine derivatives,their preparation and pharmaceutical compositions containing them |
US4414213A (en) * | 1982-03-22 | 1983-11-08 | Mead Johnson & Company | Dihydropyridyl cyclic imidate esters and their pharmaceutical use |
IL68975A (en) * | 1982-06-15 | 1987-01-30 | Sandoz Ag | 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid ester derivatives in optically active form,their preparation and pharmaceutical compositions containing them |
FR2528431B1 (fr) * | 1982-06-15 | 1986-01-10 | Sandoz Sa | Nouveaux derives de la 1,4-dihydropyridine, leur preparation et leur utilisation comme medicaments |
JPS5978186A (ja) * | 1982-10-27 | 1984-05-04 | Yoshitomi Pharmaceut Ind Ltd | 1,4−ジヒドロピリジン−3,5−ジカルボン酸エステル誘導体 |
US4794111A (en) * | 1984-05-23 | 1988-12-27 | Bayer Aktiengesellschaft | Dihydropyridine preparations containing β-blockers |
NL194389C (nl) * | 1984-06-14 | 2002-03-04 | Novartis Ag | Werkwijze voor het bereiden van een vaste dispersie van een farmaceutisch actief middel dat een lage oplosbaarheid in water heeft, in een vaste matrix van een in water oplosbaar polyalkyleenglycol als drager. |
US5260321A (en) * | 1984-11-12 | 1993-11-09 | Sandoz Ltd. | Use of 1,4-dihydropyridine derivatives and combinations thereof with calcitonins |
HU197201B (en) * | 1985-10-01 | 1989-03-28 | Sandoz Ag | Process for producing oral pharmaceutical compositions of controlled solubility of the active components |
DE3542794A1 (de) * | 1985-12-04 | 1987-06-11 | Bayer Ag | Antihypertensives kombinationspraeparat |
GB8626217D0 (en) * | 1986-11-03 | 1986-12-03 | Sandoz Ltd | Pharmaceutical compositions |
US4816263A (en) * | 1987-10-02 | 1989-03-28 | Alza Corporation | Dosage form for treating cardiovascular diseases comprising isradipine |
KR940003492B1 (ko) * | 1988-10-27 | 1994-04-23 | 주식회사 유한양행 | 1,4-디하이드로피리딘유도체 및 그의 제조방법 |
DE4222770A1 (de) * | 1992-07-10 | 1994-01-13 | Bayer Ag | Lichtaktivierbare 1-(2-Nitrobenzyl)-substituierte 1,4-Dihydropyridine |
AU2003217676B2 (en) | 2002-02-22 | 2009-06-11 | Takeda Pharmaceutical Company Limited | Active agent delivery systems and methods for protecting and administering active agents |
WO2005023787A1 (en) * | 2003-09-10 | 2005-03-17 | Shasun Chemicals And Drugs Limited | Process for the manufacture of 2,1,3-benzoxadiazole-4-carboxaldehyde |
CN103613584B (zh) * | 2013-11-27 | 2016-04-27 | 沈阳药科大学 | 一种伊拉地平合成产物后处理的方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5373327A (en) * | 1976-12-13 | 1978-06-29 | Matsushita Electric Ind Co Ltd | Power source system |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1670824C3 (de) * | 1967-03-20 | 1978-08-03 | Bayer Ag, 5090 Leverkusen | 1,4-Dihydropyridin-33-dicarbonsäurealkylester |
FR2320750A1 (fr) * | 1975-08-12 | 1977-03-11 | Hexachimie | Dihydro-1,4 pyridines et leur application therapeutique |
DE2616991A1 (de) * | 1976-04-17 | 1977-10-27 | Bayer Ag | Heterocyclisch-substituierte schwefelhaltige dihydropyridine, mehrere verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
DK149855C (da) * | 1977-06-20 | 1987-04-21 | Sandoz Ag | Analogifremgangsmaade til fremstilling af 1,4-dihydropyridinderivater |
-
1978
- 1978-12-18 CH CH1283578A patent/CH639659A5/de not_active IP Right Cessation
-
1979
- 1979-12-08 DE DE19792949491 patent/DE2949491A1/de active Granted
- 1979-12-11 SE SE7910188A patent/SE445219B/sv not_active IP Right Cessation
- 1979-12-13 BE BE1/9643A patent/BE880591A/fr not_active IP Right Cessation
- 1979-12-14 NL NL7909024A patent/NL193066C/nl not_active IP Right Cessation
- 1979-12-14 IT IT51095/79A patent/IT1164097B/it active Protection Beyond IP Right Term
- 1979-12-14 GB GB7943113A patent/GB2037766B/en not_active Expired
- 1979-12-14 GB GB08215988A patent/GB2103203B/en not_active Expired
- 1979-12-14 CY CY1321A patent/CY1321A/xx unknown
- 1979-12-17 NZ NZ192422A patent/NZ192422A/xx unknown
- 1979-12-17 FR FR7930829A patent/FR2444681A1/fr active Granted
- 1979-12-17 JP JP16396579A patent/JPS5583783A/ja active Granted
- 1979-12-17 AU AU53896/79A patent/AU536055B2/en not_active Expired
- 1979-12-17 IE IE2445/79A patent/IE49496B1/en not_active IP Right Cessation
- 1979-12-18 ZA ZA00796842A patent/ZA796842B/xx unknown
-
1985
- 1985-12-20 SG SG975/85A patent/SG97585G/en unknown
- 1985-12-30 MY MY130/85A patent/MY8500130A/xx unknown
-
1986
- 1986-01-08 KE KE3593A patent/KE3593A/xx unknown
- 1986-03-06 HK HK160/86A patent/HK16086A/xx not_active IP Right Cessation
-
1999
- 1999-05-11 NL NL990014C patent/NL990014I1/nl unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5373327A (en) * | 1976-12-13 | 1978-06-29 | Matsushita Electric Ind Co Ltd | Power source system |
Also Published As
Publication number | Publication date |
---|---|
KE3593A (en) | 1986-02-07 |
FR2444681B1 (es) | 1982-10-29 |
NL7909024A (nl) | 1980-06-20 |
JPS5583783A (en) | 1980-06-24 |
NL193066B (nl) | 1998-05-06 |
NZ192422A (en) | 1982-09-14 |
MY8500130A (en) | 1985-12-31 |
AU536055B2 (en) | 1984-04-19 |
HK16086A (en) | 1986-03-14 |
IE792445L (en) | 1980-06-18 |
GB2037766B (en) | 1983-02-16 |
GB2103203A (en) | 1983-02-16 |
BE880591A (fr) | 1980-06-13 |
CH639659A5 (de) | 1983-11-30 |
SE445219B (sv) | 1986-06-09 |
SG97585G (en) | 1986-07-18 |
SE7910188L (sv) | 1980-06-19 |
CY1321A (en) | 1986-06-27 |
GB2103203B (en) | 1983-06-08 |
AU5389679A (en) | 1980-06-26 |
NL990014I1 (nl) | 1999-07-01 |
DE2949491A1 (de) | 1980-06-26 |
NL193066C (nl) | 1998-09-08 |
GB2037766A (en) | 1980-07-16 |
FR2444681A1 (fr) | 1980-07-18 |
ZA796842B (en) | 1981-07-29 |
IT1164097B (it) | 1987-04-08 |
DE2949491C2 (es) | 1988-10-27 |
IT7951095A0 (it) | 1979-12-14 |
IE49496B1 (en) | 1985-10-16 |
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