IL95509A - Heterogeneous synthesis of master aspinins - Google Patents

Heterogeneous synthesis of master aspinins

Info

Publication number: IL95509A
Authority: IL; Israel
Prior art keywords: procedure; compound; amino; acid; acid ester
Prior art date: 1989-08-31

Application number

IL9550990A

Other languages

English (en)

Hebrew (he)

Other versions

IL95509A0 (en

Original Assignee

Marion Merrell Dow Inc

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.)

1989-08-31

Filing date

1990-08-28

Publication date

1994-10-07

1990-08-28 Application filed by Marion Merrell Dow Inc filed Critical Marion Merrell Dow Inc

1991-06-30 Publication of IL95509A0 publication Critical patent/IL95509A0/xx

1994-10-07 Publication of IL95509A publication Critical patent/IL95509A/en

Links

230000015572 biosynthetic process Effects 0.000 title claims description 8
150000002148 esters Chemical class 0.000 title description 14
238000003786 synthesis reaction Methods 0.000 title description 5
DXZDEAJXVCLRLE-UHFFFAOYSA-N azepin-2-one Chemical class O=C1C=CC=CC=N1 DXZDEAJXVCLRLE-UHFFFAOYSA-N 0.000 title 1
-1 amino-acid ester compound Chemical class 0.000 claims abstract description 44
125000004122 cyclic group Chemical group 0.000 claims abstract description 23
239000002253 acid Substances 0.000 claims abstract description 22
230000002378 acidificating effect Effects 0.000 claims abstract description 22
239000007788 liquid Substances 0.000 claims abstract description 22
239000000126 substance Substances 0.000 claims abstract description 22
238000005342 ion exchange Methods 0.000 claims abstract description 17
239000003456 ion exchange resin Substances 0.000 claims abstract description 16
229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 16
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 15
FEDJGPQLLNQAIY-UHFFFAOYSA-N 2-[(6-oxo-1h-pyridazin-3-yl)oxy]acetic acid Chemical compound OC(=O)COC=1C=CC(=O)NN=1 FEDJGPQLLNQAIY-UHFFFAOYSA-N 0.000 claims abstract description 10
229960005316 diltiazem hydrochloride Drugs 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims description 31
150000001875 compounds Chemical class 0.000 claims description 15
238000007363 ring formation reaction Methods 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
238000007126 N-alkylation reaction Methods 0.000 claims description 2
230000021736 acetylation Effects 0.000 claims description 2
238000006640 acetylation reaction Methods 0.000 claims description 2
239000002609 medium Substances 0.000 claims 2
239000012736 aqueous medium Substances 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 15
229920001467 poly(styrenesulfonates) Polymers 0.000 abstract description 10
GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 abstract description 8
229920003053 polystyrene-divinylbenzene Polymers 0.000 abstract description 3
KHQWPNQLSKDWAR-UHFFFAOYSA-N 3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoic acid Chemical compound C1=CC(OC)=CC=C1C(C(O)C(O)=O)SC1=CC=CC=C1N KHQWPNQLSKDWAR-UHFFFAOYSA-N 0.000 abstract description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
239000007787 solid Substances 0.000 description 15
239000000047 product Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
238000010438 heat treatment Methods 0.000 description 10
239000011347 resin Substances 0.000 description 10
229920005989 resin Polymers 0.000 description 10
238000004809 thin layer chromatography Methods 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
KJFRSZASZNLCDF-UHFFFAOYSA-N 1,5-benzothiazepine Chemical compound S1C=CC=NC2=CC=CC=C12 KJFRSZASZNLCDF-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
150000002894 organic compounds Chemical class 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000008367 deionised water Substances 0.000 description 4
229910021641 deionized water Inorganic materials 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
150000004702 methyl esters Chemical class 0.000 description 4
125000001624 naphthyl group Chemical class 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000002002 slurry Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229960004166 diltiazem Drugs 0.000 description 3
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000004611 spectroscopical analysis Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
FHGWEHGZBUBQKL-UHFFFAOYSA-N 1,2-benzothiazepine Chemical compound S1N=CC=CC2=CC=CC=C12 FHGWEHGZBUBQKL-UHFFFAOYSA-N 0.000 description 1
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
JQNJUZUDWVHVHJ-UHFFFAOYSA-N 8-chloro-1,5-benzothiazepine Chemical class N1=CC=CSC2=CC(Cl)=CC=C21 JQNJUZUDWVHVHJ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
238000007792 addition Methods 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000011324 bead Substances 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
229940085242 benzothiazepine derivative selective calcium channel blockers with direct cardiac effects Drugs 0.000 description 1
150000007657 benzothiazepines Chemical class 0.000 description 1
244000309464 bull Species 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
239000003218 coronary vasodilator agent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000003950 cyclic amides Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010931 ester hydrolysis Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000009313 farming Methods 0.000 description 1
125000003709 fluoroalkyl group Chemical group 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000000499 gel Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002895 organic esters Chemical group 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000005010 perfluoroalkyl group Chemical group 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
230000000063 preceeding effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012265 solid product Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
150000003738 xylenes Chemical class 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

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)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL9550990A 1989-08-31 1990-08-28 Heterogeneous synthesis of master aspinins IL95509A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US40065889A	1989-08-31	1989-08-31

Publications (2)

Publication Number	Publication Date
IL95509A0 IL95509A0 (en)	1991-06-30
IL95509A true IL95509A (en)	1994-10-07

Family

ID=23584491

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9550990A IL95509A (en)	1989-08-31	1990-08-28	Heterogeneous synthesis of master aspinins

Country Status (13)

Country	Link
EP (1)	EP0415384B1 (de)
JP (1)	JP3090212B2 (de)
KR (1)	KR0163585B1 (de)
AT (1)	ATE150459T1 (de)
AU (1)	AU628217B2 (de)
CA (1)	CA2024124C (de)
DD (1)	DD295367A5 (de)
DE (1)	DE69030222T2 (de)
ES (1)	ES2101682T3 (de)
HU (1)	HU206103B (de)
IE (1)	IE903151A1 (de)
IL (1)	IL95509A (de)
ZA (1)	ZA906810B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1249318B (it) *	1991-05-23	1995-02-22	Zambon Spa	Processo per la preparazione di benzotiazepine per ciclizzazione con acidi fosfonici
DE4313413A1 (de) *	1993-04-23	1994-10-27	Basf Ag	3-(Het)aryloxy(thio)-Carbonsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4567175A (en) *	1983-06-03	1986-01-28	Tanabe Seiyaku Co., Ltd.	8-Chloro-1,5-benzothiazepine derivatives
ZA893392B (en) *	1988-05-24	1990-01-31	Hoffmann La Roche	Process for the manufacture of optically active naphthothiazepinones
ES2069003T3 (es) *	1989-04-28	1995-05-01	Tanabe Seiyaku Co	Procedimiento para preparar derivados de 1,5-benzotiazepina.
JPH0798813B2 (ja) *	1989-04-28	1995-10-25	田辺製薬株式会社	１，５―ベンゾチアゼピン誘導体の製法

1990
- 1990-08-27 ZA ZA906810A patent/ZA906810B/xx unknown
- 1990-08-27 AU AU61382/90A patent/AU628217B2/en not_active Expired
- 1990-08-28 HU HU905508A patent/HU206103B/hu not_active IP Right Cessation
- 1990-08-28 CA CA002024124A patent/CA2024124C/en not_active Expired - Lifetime
- 1990-08-28 IL IL9550990A patent/IL95509A/en not_active IP Right Cessation
- 1990-08-28 JP JP02224560A patent/JP3090212B2/ja not_active Expired - Lifetime
- 1990-08-29 DE DE69030222T patent/DE69030222T2/de not_active Expired - Lifetime
- 1990-08-29 KR KR1019900013352A patent/KR0163585B1/ko not_active Expired - Fee Related
- 1990-08-29 AT AT90116565T patent/ATE150459T1/de not_active IP Right Cessation
- 1990-08-29 EP EP90116565A patent/EP0415384B1/de not_active Expired - Lifetime
- 1990-08-29 ES ES90116565T patent/ES2101682T3/es not_active Expired - Lifetime
- 1990-08-30 DD DD90343730A patent/DD295367A5/de unknown
- 1990-08-30 IE IE315190A patent/IE903151A1/en unknown

Also Published As

Publication number	Publication date
DD295367A5 (de)	1991-10-31
JP3090212B2 (ja)	2000-09-18
ES2101682T3 (es)	1997-07-16
KR0163585B1 (ko)	1998-12-01
HU905508D0 (en)	1991-02-28
HUT59118A (en)	1992-04-28
IE903151A1 (en)	1991-03-27
EP0415384B1 (de)	1997-03-19
DE69030222T2 (de)	1997-10-16
DE69030222D1 (de)	1997-04-24
KR910004584A (ko)	1991-03-29
EP0415384A3 (en)	1992-04-15
ATE150459T1 (de)	1997-04-15
IL95509A0 (en)	1991-06-30
AU6138290A (en)	1991-03-07
HU206103B (en)	1992-08-28
AU628217B2 (en)	1992-09-10
CA2024124A1 (en)	1991-03-01
CA2024124C (en)	2003-04-15
ZA906810B (en)	1991-10-30
EP0415384A2 (de)	1991-03-06
JPH0393778A (ja)	1991-04-18

Legal Events

Date	Code	Title	Description
1997-06-10	RH	Patent void

Publication	Publication Date	Title
CA1237719A (en)	1988-06-07	8-chloro-1,5-benzothiazepine derivatives and processes for preparing the same
EP0154838B1 (de)	1988-07-06	1,5-Benzothiazepinderivate, Verfahren zu ihrer Herstellung und Arzneimittel
EP0325965B1 (de)	1994-04-13	Verfahren zur optischen Spaltung einer rakemischen Säure
JPH0228594B2 (ja)	1990-06-25	1*55benzochiazepinjudotai
US5013835A (en)	1991-05-07	Method of preparing (+)-(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)2,3-dihydro-5H-1,5-benzothiazepine-4-one
EP0415384B1 (de)	1997-03-19	Heterogene Synthese von Azepinonen aus Estern
JPH04234866A (ja)	1992-08-24	１，５−ベンゾチアゼピン誘導体の製法
CA2015179C (en)	1996-12-10	Processes for preparing 1,5-benzothiazepine derivatives
US5250680A (en)	1993-10-05	Heterogeneous synthesis of azepinones from esters
KR970002466B1 (ko)	1997-03-05	1,5-벤조티아제핀 유도체의 제조방법
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