IL100157A - Preparation of a 1,5-benzothiazepine derivative - Google Patents

Preparation of a 1,5-benzothiazepine derivative

Info

Publication number: IL100157A
Authority: IL; Israel
Prior art keywords: acetic acid; hydroxy; compound; dihydro; ethyl
Prior art date: 1990-11-29

Application number

IL10015791A

Other languages

English (en)

Other versions

IL100157A0 (en

Original Assignee

Tanabe Seiyaku Co

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.)

1990-11-29

Filing date

1991-11-26

Publication date

1995-12-08

1991-11-26 Application filed by Tanabe Seiyaku Co filed Critical Tanabe Seiyaku Co

1992-08-18 Publication of IL100157A0 publication Critical patent/IL100157A0/xx

1995-12-08 Publication of IL100157A publication Critical patent/IL100157A/en

Links

KJFRSZASZNLCDF-UHFFFAOYSA-N 1,5-benzothiazepine Chemical class S1C=CC=NC2=CC=CC=C12 KJFRSZASZNLCDF-UHFFFAOYSA-N 0.000 title description 2
238000002360 preparation method Methods 0.000 title description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 72
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 69
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 36
238000000034 method Methods 0.000 claims abstract description 31
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims abstract description 18
239000012346 acetyl chloride Substances 0.000 claims abstract description 16
239000012046 mixed solvent Substances 0.000 claims abstract description 16
238000004519 manufacturing process Methods 0.000 claims abstract description 5
238000006243 chemical reaction Methods 0.000 claims description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
239000007858 starting material Substances 0.000 claims description 5
ZKAFCDWKAHKZJG-UHFFFAOYSA-N 1,5-benzothiazepin-3-ol Chemical class N1=CC(O)=CSC2=CC=CC=C21 ZKAFCDWKAHKZJG-UHFFFAOYSA-N 0.000 claims 3
HSUGRBWQSSZJOP-UHFFFAOYSA-N 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate Chemical compound C1=CC(OC)=CC=C1C1C(OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-UHFFFAOYSA-N 0.000 abstract 2
NZHUXMZTSSZXSB-UHFFFAOYSA-N 5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4-one Chemical compound C1=CC(OC)=CC=C1C1C(O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 NZHUXMZTSSZXSB-UHFFFAOYSA-N 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 25
239000002904 solvent Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
229910000041 hydrogen chloride Inorganic materials 0.000 description 8
230000021736 acetylation Effects 0.000 description 7
238000006640 acetylation reaction Methods 0.000 description 7
239000012345 acetylating agent Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
238000010438 heat treatment Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
230000000704 physical effect Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000000376 reactant Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003218 coronary vasodilator agent Substances 0.000 description 1
230000007547 defect Effects 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000006340 racemization Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Cardiology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (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)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Diaphragms For Electromechanical Transducers (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Other In-Based Heterocyclic Compounds (AREA)

IL10015791A 1990-11-29 1991-11-26 Preparation of a 1,5-benzothiazepine derivative IL100157A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP33601090		1990-11-29

Publications (2)

Publication Number	Publication Date
IL100157A0 IL100157A0 (en)	1992-08-18
IL100157A true IL100157A (en)	1995-12-08

Family

ID=18294763

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10015791A IL100157A (en)	1990-11-29	1991-11-26	Preparation of a 1,5-benzothiazepine derivative

Country Status (15)

Country	Link
US (1)	US5169946A (de)
EP (1)	EP0488210B1 (de)
JP (1)	JPH0822856B2 (de)
KR (1)	KR0133056B1 (de)
CN (1)	CN1031342C (de)
AT (1)	ATE107638T1 (de)
AU (1)	AU634108B2 (de)
DE (1)	DE69102614T2 (de)
DK (1)	DK0488210T3 (de)
ES (1)	ES2059020T3 (de)
FI (1)	FI104173B1 (de)
HK (1)	HK174295A (de)
HU (1)	HU209830B (de)
IE (1)	IE914135A1 (de)
IL (1)	IL100157A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5705638A (en) *	1995-12-05	1998-01-06	Tanabe Seiyaku Co., Ltd.	Process for preparing optically active 3-hydroxy-1,5-benzothiazepine derivative and intermediate therefor
DE69601210T2 (de) *	1995-12-05	1999-05-20	Tanabe Seiyaku Co., Ltd., Osaka	Optisch aktive Benzothiazepinderivate und Verfahren zu ihrer Herstellung

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3562257A (en) *	1967-10-28	1971-02-09	Tanabe Seiyaku Co	Benzothiazepine derivatives
FR2360124A1 (fr) *	1976-07-30	1978-02-24	Amiens Const Electro Mecan	Procede de controle de commutation de la puissance de chauffage dans un appareil electrodomestique a programmateur et dispositif pour la mise en oeuvre dudit procede
US4590188A (en) *	1984-02-18	1986-05-20	Tanabe Seiyaku Co., Ltd.	1,5-benzothiazepine derivatives and their pharmaceutical use
JPS62132876A (ja) *	1985-12-04	1987-06-16	Kohjin Co Ltd	１，５−ベンゾチアゼピン誘導体の製法
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

1991
- 1991-11-26 IL IL10015791A patent/IL100157A/en not_active IP Right Cessation
- 1991-11-27 IE IE413591A patent/IE914135A1/en not_active IP Right Cessation
- 1991-11-27 DK DK91120269.5T patent/DK0488210T3/da active
- 1991-11-27 EP EP91120269A patent/EP0488210B1/de not_active Expired - Lifetime
- 1991-11-27 AT AT91120269T patent/ATE107638T1/de not_active IP Right Cessation
- 1991-11-27 KR KR1019910021366A patent/KR0133056B1/ko not_active Expired - Lifetime
- 1991-11-27 JP JP3356115A patent/JPH0822856B2/ja not_active Expired - Lifetime
- 1991-11-27 US US07/805,561 patent/US5169946A/en not_active Expired - Lifetime
- 1991-11-27 ES ES91120269T patent/ES2059020T3/es not_active Expired - Lifetime
- 1991-11-27 DE DE69102614T patent/DE69102614T2/de not_active Expired - Lifetime
- 1991-11-28 FI FI915625A patent/FI104173B1/fi not_active IP Right Cessation
- 1991-11-28 HU HU913713A patent/HU209830B/hu unknown
- 1991-11-28 AU AU88253/91A patent/AU634108B2/en not_active Expired
- 1991-11-29 CN CN91111039A patent/CN1031342C/zh not_active Expired - Lifetime
1995
- 1995-11-16 HK HK174295A patent/HK174295A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
HUT61988A (en)	1993-03-29
IL100157A0 (en)	1992-08-18
DE69102614T2 (de)	1994-11-24
HU913713D0 (en)	1992-02-28
CN1031342C (zh)	1996-03-20
JPH0543564A (ja)	1993-02-23
FI104173B (fi)	1999-11-30
ATE107638T1 (de)	1994-07-15
US5169946A (en)	1992-12-08
KR920009808A (ko)	1992-06-25
DK0488210T3 (da)	1994-08-01
ES2059020T3 (es)	1994-11-01
KR0133056B1 (ko)	1998-04-17
DE69102614D1 (de)	1994-07-28
FI915625L (fi)	1992-05-30
AU634108B2 (en)	1993-02-11
HU209830B (en)	1994-11-28
AU8825391A (en)	1992-06-04
IE914135A1 (en)	1992-06-03
CN1062141A (zh)	1992-06-24
FI104173B1 (fi)	1999-11-30
FI915625A0 (fi)	1991-11-28
JPH0822856B2 (ja)	1996-03-06
EP0488210A1 (de)	1992-06-03
HK174295A (en)	1995-11-24
EP0488210B1 (de)	1994-06-22

Legal Events

Date	Code	Title
1996-06-18	FF	Patent granted
1998-04-05	KB	Patent renewed
2002-02-10	KB	Patent renewed
2010-05-17	KB	Patent renewed
2012-07-31	EXP	Patent expired

Publication	Publication Date	Title
RU2224754C2 (ru)	2004-02-27	Кристаллическое производное дибензотиазепина, способ получения и фармацевтическая композиция на его основе
JP2009242407A (ja)	2009-10-22	オランザピンの製造方法および中間体
US4511510A (en)	1985-04-16	Process for preparing a 7-chloro-5-(2-chlorophenyl)-benzodiazepinone
JP3067878B2 (ja)	2000-07-24	２−（２’，４’−ジヒドロキシフェニル）−４，６−ジアリール−ｓ−トリアジンの製造方法
US5169946A (en)	1992-12-08	Process for preparing 1,5-benzothiazepine derivative
JPH04234866A (ja)	1992-08-24	１，５−ベンゾチアゼピン誘導体の製法
EP0395323B1 (de)	1997-06-11	Verfahren zur Herstellung von 1,5-Benzothiazepin-Derivaten
CA2056129C (en)	1996-10-15	Process for preparing 1,5-benzothiazepine derivative
HK1003789B (en)	1998-11-06	Process for preparing 1,5-benzothiazepine derivatives
JP3101841B2 (ja)	2000-10-23	ホスホン酸での環化によるベンゾチアゼピンの製造法
US5663332A (en)	1997-09-02	Method for the preparation of 3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxy-phenyl)-1,5-benzothiazepine-4(5H)-one
US5260457A (en)	1993-11-09	Process for producing coumarin and derivative thereof
US5859241A (en)	1999-01-12	Process for the preparation of a benzothiazepine
JP2676720B2 (ja)	1997-11-17	１，５−ベンゾチアゼピン誘導体の製法
US5310904A (en)	1994-05-10	Process for preparing optically active benzothiazepine compounds by asymmetric reduction
JPH03294257A (ja)	1991-12-25	α―ブロモイソワレリル尿素の製造方法
JPS60116677A (ja)	1985-06-24	ベンゾチアゼピン誘導体の製造法
IE61196B1 (en)	1994-10-19	Process for preparing 1,5-benzothiazepine derivatives
WO1996036594A1 (en)	1996-11-21	Method for preparing certain acetonitriles
HU195489B (en)	1988-05-30	Process for producing 1,2-diphenyl-4 brackets open /2-phenyl-sulfinyl/-ethyl brackets closed-3,5-pyrazolidindione
JPH0573749B2 (de)	1993-10-15
JPH0573746B2 (de)	1993-10-15