HK95488A - Novel method of preparing benzothiazepine derivatives - Google Patents

Novel method of preparing benzothiazepine derivatives

Info

Publication number
HK95488A
HK95488A HK954/88A HK95488A HK95488A HK 95488 A HK95488 A HK 95488A HK 954/88 A HK954/88 A HK 954/88A HK 95488 A HK95488 A HK 95488A HK 95488 A HK95488 A HK 95488A
Authority
HK
Hong Kong
Prior art keywords
mixture
acetone
lower alkyl
water
compound
Prior art date
Application number
HK954/88A
Other languages
English (en)
French (fr)
Inventor
Mitsunori Gaino
Ikuo Iijima
Shigeru Nishimoto
Kuichiro Ikeda
Tokuo Fujii
Original Assignee
Tanabe Seiyaku Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=16373149&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=HK95488(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Tanabe Seiyaku Co., Ltd. filed Critical Tanabe Seiyaku Co., Ltd.
Publication of HK95488A publication Critical patent/HK95488A/en

Links

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)

Claims (7)

1. Verfahren zur Herstellung eines Benzothiazepinderivates der Formel worin R Wasserstoff oder Acetyl darstellt, oder eines pharmazeutisch annehmbaren Säureadditionssalzes desselben, gekennzeichnet durch Kondensieren einer Verbindung der Formel worin R die vorstehend angegebene Bedeutung hat, mit 2-(Dimethylamino)ethylchlorid entweder in Gegenwart von Kaliumhydroxid in Aceton oder in Gegenwart von Kaliumcarbonat in einem Lösungsmittel, ausgewählt aus Aceton, Niedrigalkylacetat, einem Gemisch aus Aceton und Wasser und einem Gemisch aus Niedrigalkylacetat und Wasser, und-sofern dies erforderlich ist-weitere Umwandlung des Produktes in ein pharmazeutisch annehmbares Säureadditionssalz desselben.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass die Kondensation entweder in Gegenwart von 1 bis 3 Mol Kaliumhydroxid pro Mol der Verbindung (11) in Aceton bei einer Temperatur zwischen 30°C und der Rückflusstemperatur von Aceton, oder in Gegenwart von 1 bis 5 Mol Kaliumcarbonat pro Mol der Verbindung (II) in einem Lösungsmittel, ausgewählt aus Aceton, Niedrigalkylacetat, einem Gemisch aus Aceton und Wasser und einem Gemisch aus Niedrigalkylacetat und Wasser, bei einer Temperatur von 30°C und der Rückflusstemperatur des verwendeten Lösungsmittels, durchgeführt wird.
3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass, wenn Kaliumhydroxid und Aceton verwendet werden, die Kondensation durch Rühren eines Gemisches der Verbindung (11), 2-(Dimethylamino)ethylchlorid, Kaliumhydroxid und Aceton bei einer Temperatur von 40 bis 57°C durchgeführt wird; wenn Kaliumcarbonat und Aceton oder Niedrigalkylacetat verwendet werden, die Kondensation durch Rückflussbehandlung eines Gemisches der Verbindung (11), 2-(Dimethylamino)ethylchlorid, Kaliumcarbonat und Aceton oder Niedrigalkylacetat durchgeführt wird; wenn Kaliumcarbonat und ein Gemisch aus Aceton und Wasser oder ein Gemisch aus Niedrigalkylacetat und Wasser verwendet werden, die Kondensation durch Rückflussbehandlung eines Gemisches der Verbindung (11), 2-(Dimethylamino)-ethylchlorid, Kaliumcarbonat und Aceton oder Niedrigalkylacetat, Zugabe von Wasser zu dem Gemisch und weiterer Rückflussbehandlung des wässrigen Gemisches durchgeführt wird.
4. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass das Niedrigalkylacetat Methylacetat oder Ethylacetat darstellt.
5. Verfahren nach Anspruch 3, dadurch gekennzeichnet, dass das Niedrigalkylacetat Methylacetat oder Ethylacetat darstellt.
6. Verfahren nach Anspruch 3, dadurch gekennzeichnet, dass 2-(Dimethylamino)ethylchlorid in Form von dessen Hydrochlorid verwendet wird.
7. Verfahren nach Anspruch 6, dadurch gekennzeichnet, dass die Menge an Kaliumhydroxid 2 bis 2,5 Mol pro Mol der Verbindung (II), und die Menge an Kaliumcarbonat 2 bis 3 Mol pro Mol der Verbindung (II) beträgt.
HK954/88A 1981-12-07 1988-11-24 Novel method of preparing benzothiazepine derivatives HK95488A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
HK95488A true HK95488A (en) 1988-12-02

Family

ID=16373149

Family Applications (1)

Application Number Title Priority Date Filing Date
HK954/88A HK95488A (en) 1981-12-07 1988-11-24 Novel method of preparing benzothiazepine derivatives

Country Status (15)

Country Link
US (1) US4438035B1 (de)
EP (1) EP0081234B1 (de)
JP (1) JPS5899471A (de)
KR (1) KR860002034B1 (de)
AT (1) ATE15799T1 (de)
BG (1) BG38937A3 (de)
CA (1) CA1177075A (de)
DE (1) DE3266583D1 (de)
DK (1) DK154022C (de)
ES (1) ES8401953A1 (de)
FI (1) FI79705C (de)
HK (1) HK95488A (de)
HU (1) HU187431B (de)
IE (1) IE54241B1 (de)
SU (1) SU1176839A3 (de)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
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.
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
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
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
ES2118292T3 (es) * 1994-09-16 1998-09-16 Orion Corp Fermion Metodo para la preparacion de 3-hidroxi-5-(2-dimetilamino)-etil)-2,3-dihidro-4-(metoxifenil)-1,5-benzotiazepin-4(5h)-ona y uso del producto para elaborar compuestos farmaceuticamente activos.
FI97725C (fi) * 1995-02-17 1997-02-10 Orion Yhtymae Oy Menetelmä diltiatseemin valmistamiseksi
US5559229A (en) * 1995-06-01 1996-09-24 Acic (Canada) Inc. Method for the manufacture of benzothiazepine
WO1996038429A1 (en) * 1995-06-01 1996-12-05 Acic (Canada) Inc. Method for the manufacture of benzothiazepine derivatives
SG50796A1 (en) * 1996-02-23 1998-07-20 Tanabe Seiyaku Co Process for preparing 1,5-benzothiazepine derivative
IL123352A0 (en) 1997-02-27 1998-09-24 Tanabe Seiyaku Co Process for preparing an 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
WO2017094029A2 (en) * 2015-12-01 2017-06-08 Sun Pharmaceutical Industries Ltd. Parenteral dosage form of diltiazem

Family Cites Families (3)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
JPS6317832B2 (de) 1988-04-15
EP0081234A1 (de) 1983-06-15
IE822836L (en) 1983-06-07
US4438035A (en) 1984-03-20
IE54241B1 (en) 1989-08-02
FI79705B (fi) 1989-10-31
ES517966A0 (es) 1984-01-01
KR860002034B1 (ko) 1986-11-17
CA1177075A (en) 1984-10-30
DK154022C (da) 1989-02-20
DE3266583D1 (en) 1985-10-31
EP0081234B1 (de) 1985-09-25
KR840002819A (ko) 1984-07-21
FI824165A0 (fi) 1982-12-03
SU1176839A3 (ru) 1985-08-30
US4438035B1 (en) 1994-07-26
FI824165L (fi) 1983-06-08
HU187431B (en) 1986-01-28
DK154022B (da) 1988-10-03
JPS5899471A (ja) 1983-06-13
BG38937A3 (en) 1986-03-14
FI79705C (fi) 1990-02-12
ES8401953A1 (es) 1984-01-01
DK540382A (da) 1983-06-08
ATE15799T1 (de) 1985-10-15

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