KR840002819A - 벤조티아제핀 유도체의 제조방법 - Google Patents
벤조티아제핀 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840002819A KR840002819A KR1019820005453A KR820005453A KR840002819A KR 840002819 A KR840002819 A KR 840002819A KR 1019820005453 A KR1019820005453 A KR 1019820005453A KR 820005453 A KR820005453 A KR 820005453A KR 840002819 A KR840002819 A KR 840002819A
- Authority
- KR
- South Korea
- Prior art keywords
- acetone
- lower alkyl
- mixture
- formula
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 6
- 150000007657 benzothiazepines Chemical class 0.000 title claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 25
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 14
- -1 alkyl acetates Chemical class 0.000 claims 11
- 239000000203 mixture Substances 0.000 claims 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- 238000009833 condensation Methods 0.000 claims 5
- 230000005494 condensation Effects 0.000 claims 5
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical group CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- PVPAMMQRQRLZBS-UHFFFAOYSA-N 1-hydroxy-7,9-dihydro-3h-purine-2,6,8-trione Chemical compound O=C1N(O)C(=O)NC2=C1NC(=O)N2 PVPAMMQRQRLZBS-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epoxy Resins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims (7)
- 다음 일반식(Ⅱ)의 화합물을 아세톤 중 수산화 칼륨의 존재하에서 또는 아세톤, 저급 알킬 아세테이트, 아세톤 및 문의 혼합물 및 저급 알킬 아세테이트 및 물의 혼합물로부터 선택한 용매중 탄산칼륨의 존재하에서 2-(디메틸아미노)-에틸할리드와 죽합시키고, 필요하다면, 생성물을 이의 약학적으로 허용되는 산 부가염으로 전환시킴을 특징으로 하는, 다음 일반식(Ⅰ)의 벤조티아제핀 유도체 또는 이의 약학적으로 허용되는 산 부가염의 제조방법.상기식에서R은 수소 또는 아세틸이다.
- 제1항에 있어서, 축합을 아세톤중 일반식(Ⅱ)의 화합물 몰당 수산화칼륜 1내지 3몰의 존재하에 30℃내지 아세톤의 환류온도에서 또는 아세톤, 저급 알킬 아세테이트, 아세톤 및 물의 혼합물 및 저급 알킬 아세테이트 및 물의 혼합물로부터 선택한 용매중 일반식(Ⅱ)의 화합물 몰당 탄산칼륨 1내지 5몰의 존재하에 30℃내지 사용한 용매의 환류 온도에서 진행시키는 방법.
- 제1또는 2항에 있어서, 수산화칼륨 및 아세톤을 사용할때에는, 축합을 일반식(Ⅱ)의 화합물, 2-(디메틸아미노)에틸 클로라이드, 수산화칼륨 및 아세톤의 혼합물을 40내지 57℃에서 교반함으로서 진행시키고; 탄산 칼륨 및 아세톤 또는 저급알킬 아세테이트를 사용할때에는, 축합을 일반식(Ⅱ)의 화합물, 2-(디메틸아미노)에틸 클로라이드, 탄산칼륨 및 아세톤 또는 저급 알킬 아세테이트의 혼합물을 환류함으로써 진행시키고; 탄산칼륨 및 아세톤 및 물의 혼합물 또는 저급 알킬 아세테이트 및 물의 혼합물을 사용할 때에는, 축합을 일반식(Ⅱ)의 화합물, 2-(디메틸아미노)에틸 클로라이드, 탄산 칼륨 및 아세톤 또는 저급 알킬 아세테이트의 혼합물을 환류하고, 이 혼합물에 물을 가한후 이수성 혼합물을 더욱 환류함으로써 진행시키는 방법.
- 제1또는 2항에 있어서, 저급알킬 아세테이트가 메틸 아세테이트 또는 에틸 아세테이트인 방법.
- 제3항에 있어서, 저급 알킬 아세테이트가 메틸 아세테이트 또는 에틸 아세테이트인 방법.
- 제3항에 있어서, 2-(디메틸아미노)에틸 클로라이드를 이의 염산염 형태로 사용하는 방법.
- 제6항에 있어서, 수산화나트륨의 양이 일반식(Ⅱ)의 화합물 몰당 2내지 2.5몰이고, 탄산칼륨의 양이 일반식(Ⅱ)의 화합물 몰당 2내지 3몰인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP56197358A JPS5899471A (ja) | 1981-12-07 | 1981-12-07 | ベンゾチアゼピン誘導体の新規製造法 |
JP56-197358 | 1981-12-07 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840002819A true KR840002819A (ko) | 1984-07-21 |
KR860002034B1 KR860002034B1 (ko) | 1986-11-17 |
Family
ID=16373149
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR8205453A KR860002034B1 (ko) | 1981-12-07 | 1982-12-06 | 벤조티아제핀 유도체의 제조방법 |
Country Status (15)
Country | Link |
---|---|
US (1) | US4438035B1 (ko) |
EP (1) | EP0081234B1 (ko) |
JP (1) | JPS5899471A (ko) |
KR (1) | KR860002034B1 (ko) |
AT (1) | ATE15799T1 (ko) |
BG (1) | BG38937A3 (ko) |
CA (1) | CA1177075A (ko) |
DE (1) | DE3266583D1 (ko) |
DK (1) | DK154022C (ko) |
ES (1) | ES8401953A1 (ko) |
FI (1) | FI79705C (ko) |
HK (1) | HK95488A (ko) |
HU (1) | HU187431B (ko) |
IE (1) | IE54241B1 (ko) |
SU (1) | SU1176839A3 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11241379B2 (en) | 2015-12-01 | 2022-02-08 | Sun Pharmaceutical Industries Limited | Parenteral dosage form of diltiazem |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8316032D0 (en) * | 1983-06-11 | 1983-07-13 | Tanabe Seiyaku Co | Benzothiazepine derivatives |
IT1206505B (it) * | 1983-07-22 | 1989-04-27 | Schiapparelli Farma | Nuovi derivati benzotiazepinonici, metodo per la loro preparazione e composizioni farmaceutiche che licontengono. |
GB2154577A (en) * | 1984-02-18 | 1985-09-11 | Tanabe Seiyaku Co | 1,5-benzothiazepines |
IL71538A (en) * | 1984-04-13 | 1987-07-31 | Abic Ltd | Process for the preparation of benzothiazepine derivatives |
US4758954A (en) * | 1984-07-25 | 1988-07-19 | Computer Services Corporation | Method of adjusting ticket fares |
US4652561A (en) * | 1986-02-26 | 1987-03-24 | Hoffmann-La Roche Inc. | Naphtho[1,2-b]-1,4-thiazepinones |
IL81954A0 (en) * | 1986-03-24 | 1987-10-20 | Hoffmann La Roche | Naphthothiazocinones,their manufacture and pharmaceutical compositions containing them |
US4871731A (en) * | 1987-10-07 | 1989-10-03 | Marion Laboratories, Inc. | Captopril and diltiazem composition and the like |
US4808580A (en) * | 1987-12-17 | 1989-02-28 | Hoffmann-La Roche Inc. | Naphtho[1,2-b][1,4]thiazepin-4(5H)-ones and use thereof in treatment of ischemia and blood pressure lowering |
IT1226301B (it) * | 1988-07-26 | 1990-12-27 | Zambon Spa | Processo per la preparazione di intermedi per la sintesi del diltiazem. |
FR2641535B1 (fr) * | 1989-01-11 | 1991-03-15 | Synthelabo | Procede de preparation de (+) - (2s, 3s)-hydroxy-3 (methoxy-4 phenyl)-2 dihydro-2,3 5h-benzothiazepine-1,5 one-4 |
USRE34935E (en) * | 1989-01-11 | 1995-05-09 | Synthelabo | Method for preparing (+)-(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-5H-1,5-benzothiazepine-4-one and chlorinated derivatives thereof |
US5128469A (en) * | 1989-04-28 | 1992-07-07 | Tanabe Seiyaku Co., Ltd. | Process for preparing 1,5-benzothiazepine derivatives |
JPH085869B2 (ja) * | 1990-03-08 | 1996-01-24 | 田辺製薬株式会社 | 1,5−ベンゾチアゼピン誘導体の製法 |
NL9000763A (nl) * | 1990-03-31 | 1991-10-16 | Stamicarbon | Werkwijze voor het bereiden van 1,5-benzothiazepine-derivaten. |
IT1255545B (it) * | 1992-10-23 | 1995-11-09 | Procedimento per la preparazione di diltiazem | |
ATE167858T1 (de) * | 1994-09-16 | 1998-07-15 | Orion Corp Fermion | Verfahren zur herstellung von pharmazeutisch aktiven benzothiazepinderivaten. |
FI97725C (fi) * | 1995-02-17 | 1997-02-10 | Orion Yhtymae Oy | Menetelmä diltiatseemin valmistamiseksi |
WO1996038429A1 (en) * | 1995-06-01 | 1996-12-05 | Acic (Canada) Inc. | Method for the manufacture of benzothiazepine derivatives |
US5559229A (en) * | 1995-06-01 | 1996-09-24 | Acic (Canada) Inc. | Method for the manufacture of benzothiazepine |
SG50796A1 (en) * | 1996-02-23 | 1998-07-20 | Tanabe Seiyaku Co | Process for preparing 1,5-benzothiazepine derivative |
TW438787B (en) | 1997-02-27 | 2001-06-07 | Tanabe Seiyaku Co | Process for preparing optically active trans-3-substituted glycidic acid ester |
US6635277B2 (en) | 2000-04-12 | 2003-10-21 | Wockhardt Limited | Composition for pulsatile delivery of diltiazem and process of manufacture |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3075967A (en) * | 1961-06-12 | 1963-01-29 | Olin Mathieson | Benzothiazines |
US3562257A (en) * | 1967-10-28 | 1971-02-09 | Tanabe Seiyaku Co | Benzothiazepine derivatives |
JPS57106673A (en) * | 1980-12-24 | 1982-07-02 | Chugai Pharmaceut Co Ltd | Dibenzo(b,f)(1,4)oxazepin derivative |
-
1981
- 1981-12-07 JP JP56197358A patent/JPS5899471A/ja active Granted
-
1982
- 1982-11-29 IE IE2836/82A patent/IE54241B1/en not_active IP Right Cessation
- 1982-11-30 CA CA000416635A patent/CA1177075A/en not_active Expired
- 1982-12-01 US US06445964 patent/US4438035B1/en not_active Expired - Lifetime
- 1982-12-03 FI FI824165A patent/FI79705C/fi not_active IP Right Cessation
- 1982-12-06 DK DK540382A patent/DK154022C/da not_active IP Right Cessation
- 1982-12-06 BG BG058822A patent/BG38937A3/xx unknown
- 1982-12-06 HU HU823912A patent/HU187431B/hu unknown
- 1982-12-06 ES ES517966A patent/ES8401953A1/es not_active Expired
- 1982-12-06 KR KR8205453A patent/KR860002034B1/ko active
- 1982-12-06 SU SU823524316A patent/SU1176839A3/ru active
- 1982-12-07 EP EP82111317A patent/EP0081234B1/en not_active Expired
- 1982-12-07 DE DE8282111317T patent/DE3266583D1/de not_active Expired
- 1982-12-07 AT AT82111317T patent/ATE15799T1/de not_active IP Right Cessation
-
1988
- 1988-11-24 HK HK954/88A patent/HK95488A/xx not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11241379B2 (en) | 2015-12-01 | 2022-02-08 | Sun Pharmaceutical Industries Limited | Parenteral dosage form of diltiazem |
Also Published As
Publication number | Publication date |
---|---|
IE822836L (en) | 1983-06-07 |
ES517966A0 (es) | 1984-01-01 |
HU187431B (en) | 1986-01-28 |
JPS5899471A (ja) | 1983-06-13 |
FI79705B (fi) | 1989-10-31 |
DK154022B (da) | 1988-10-03 |
ATE15799T1 (de) | 1985-10-15 |
BG38937A3 (en) | 1986-03-14 |
DK540382A (da) | 1983-06-08 |
IE54241B1 (en) | 1989-08-02 |
CA1177075A (en) | 1984-10-30 |
KR860002034B1 (ko) | 1986-11-17 |
FI824165L (fi) | 1983-06-08 |
FI824165A0 (fi) | 1982-12-03 |
DE3266583D1 (en) | 1985-10-31 |
ES8401953A1 (es) | 1984-01-01 |
EP0081234A1 (en) | 1983-06-15 |
FI79705C (fi) | 1990-02-12 |
DK154022C (da) | 1989-02-20 |
US4438035A (en) | 1984-03-20 |
HK95488A (en) | 1988-12-02 |
JPS6317832B2 (ko) | 1988-04-15 |
SU1176839A3 (ru) | 1985-08-30 |
EP0081234B1 (en) | 1985-09-25 |
US4438035B1 (en) | 1994-07-26 |
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