DD295367A5 - Verfahren zur cyclisierung von aminosaeureesterverbindungen - Google Patents

Verfahren zur cyclisierung von aminosaeureesterverbindungen Download PDF

Info

Publication number: DD295367A5
Authority: DD; German Democratic Republic
Prior art keywords: compound; amino acid; acid ester; exchange resin; ion exchange
Prior art date: 1989-08-31

Application number

DD90343730A

Other languages

German (de)

English (en)

Inventor

Daniel E Martin

Original Assignee

��@��@��@��Kk��

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

1990-08-30

Publication date

1991-10-31

1990-08-30 Application filed by ��@��@��@��Kk�� filed Critical ��@��@��@��Kk��

1991-10-31 Publication of DD295367A5 publication Critical patent/DD295367A5/de

Links

238000000034 method Methods 0.000 title claims description 56
150000001875 compounds Chemical class 0.000 title claims description 31
150000001413 amino acids Chemical class 0.000 title description 2
-1 amino-acid ester compound Chemical class 0.000 claims abstract description 45
125000004122 cyclic group Chemical group 0.000 claims abstract description 23
239000007788 liquid Substances 0.000 claims abstract description 22
230000002378 acidificating effect Effects 0.000 claims abstract description 21
239000003456 ion exchange resin Substances 0.000 claims abstract description 17
229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 17
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 16
239000002253 acid Substances 0.000 claims abstract description 14
229920001467 poly(styrenesulfonates) Polymers 0.000 claims abstract description 14
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
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
238000007363 ring formation reaction Methods 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 6
229910052801 chlorine Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
238000007126 N-alkylation reaction Methods 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
230000021736 acetylation Effects 0.000 claims description 2
238000006640 acetylation reaction Methods 0.000 claims description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
239000002609 medium Substances 0.000 claims 2
239000012736 aqueous medium Substances 0.000 claims 1
238000005755 formation reaction Methods 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 15
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
239000000126 substance Substances 0.000 abstract description 7
229920003053 polystyrene-divinylbenzene Polymers 0.000 abstract description 3
238000005342 ion exchange Methods 0.000 abstract description 2
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 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 44
150000002500 ions Chemical class 0.000 description 17
239000007787 solid Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
238000010438 heat treatment Methods 0.000 description 11
239000000047 product Substances 0.000 description 10
239000011347 resin Substances 0.000 description 10
229920005989 resin Polymers 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
238000004809 thin layer chromatography 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 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
238000003756 stirring Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000008367 deionised water Substances 0.000 description 5
229910021641 deionized water Inorganic materials 0.000 description 5
150000002894 organic compounds Chemical class 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000002002 slurry Substances 0.000 description 5
229920001429 chelating resin Polymers 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
230000007935 neutral effect Effects 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
238000007792 addition Methods 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
150000007657 benzothiazepines Chemical class 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
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 description 3
FHGWEHGZBUBQKL-UHFFFAOYSA-N 1,2-benzothiazepine Chemical compound S1N=CC=CC2=CC=CC=C12 FHGWEHGZBUBQKL-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
238000004587 chromatography analysis Methods 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
125000000962 organic group Chemical group 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
239000000376 reactant Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
KHQWPNQLSKDWAR-CABCVRRESA-N (2s,3s)-3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoic acid Chemical compound C1=CC(OC)=CC=C1[C@@H]([C@@H](O)C(O)=O)SC1=CC=CC=C1N KHQWPNQLSKDWAR-CABCVRRESA-N 0.000 description 1
XZPLOMKLRYGXOZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-3-ol Chemical compound C1=CC(OC)=CC=C1C1C(O)C=NC2=CC=CC=C2S1 XZPLOMKLRYGXOZ-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
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241001565331 Margarodes Species 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
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229940085242 benzothiazepine derivative selective calcium channel blockers with direct cardiac effects Drugs 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001246 bromo group Chemical group Br* 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
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000004965 chloroalkyl group Chemical group 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method 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
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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000003709 fluoroalkyl group Chemical group 0.000 description 1
239000000499 gel Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
150000002440 hydroxy compounds Chemical class 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
229910001410 inorganic ion Inorganic materials 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
MPWGGMIUPWSNEV-CVEARBPZSA-N methyl (2s,3s)-3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoate Chemical compound S([C@H]([C@@H](O)C(=O)OC)C=1C=CC(OC)=CC=1)C1=CC=CC=C1N MPWGGMIUPWSNEV-CVEARBPZSA-N 0.000 description 1
AUAGWRDIDRGDIT-UHFFFAOYSA-N methyl 3-(2-amino-5-chlorophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoate Chemical compound C=1C=C(OC)C=CC=1C(C(O)C(=O)OC)SC1=CC(Cl)=CC=C1N AUAGWRDIDRGDIT-UHFFFAOYSA-N 0.000 description 1
MPWGGMIUPWSNEV-UHFFFAOYSA-N methyl 3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoate Chemical compound C=1C=C(OC)C=CC=1C(C(O)C(=O)OC)SC1=CC=CC=C1N MPWGGMIUPWSNEV-UHFFFAOYSA-N 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
150000007965 phenolic acids Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229940061610 sulfonated phenol Drugs 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 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)

DD90343730A 1989-08-31 1990-08-30 Verfahren zur cyclisierung von aminosaeureesterverbindungen DD295367A5 (de)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
DD295367A5 true DD295367A5 (de)	1991-10-31

Family

ID=23584491

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90343730A DD295367A5 (de)	1989-08-31	1990-08-30	Verfahren zur cyclisierung von aminosaeureesterverbindungen

Country Status (13)

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

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/he 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/en 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
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 (en)	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 (en)	1991-03-06
IL95509A (he)	1994-10-07
JPH0393778A (ja)	1991-04-18

Legal Events

Date	Code	Title	Description
2004-04-28	IF04	In force in the year 2004	Expiry date: 20100831

Publication	Publication Date	Title
EP0146080A2 (de)	1985-06-26	Verfahren zur Racematspaltung bicyclischer Imino-alpha-carbonsäureester
DE19619665A1 (de)	1997-11-20	Racemattrennung von Ketamin
DE69008368T2 (de)	1994-11-17	Verfahren zur Herstellung von (+)-(2S,3S)-3-hydroxy-2-(4-methoxy-phenyl)-2,3-dihydro-5H-1,5-benzothiazepin-4-on-Derivaten.
DE68902001T2 (de)	1993-02-11	Verfahren zur herstellung von s-metoprolol und dessen zwischenprodukten.
DE69906738T2 (de)	2003-12-18	Substituierte benzopyran derivate und ihre verwendung als anticonvulsiva
DE69101796T2 (de)	1994-10-06	Verfahren zur Herstellung von Bisphenol A.
DE69030222T2 (de)	1997-10-16	Heterogene Synthese von Azepinonen aus Estern
DE19506549A1 (de)	1995-08-31	Verfahren zur Herstellung von 1,3-Dihydroxy-4,6-bis-[alpha-methyl-alpha-(4'-hydroxyphenyl)-ethyl]-benzol
DE4217103C2 (de)	2000-08-10	Verfahren zur Herstellung eines Benzothiazepins durch Cyclisierung mit Phosphonsäuren
DE4023773B4 (de)	2004-01-08	Verfahren zur optischen Auftrennung von zur Herstellung von Diltiazem geeigneten Zwischenprodukten
DE3906460C1 (he)	1990-11-15
DE4021999C2 (de)	2002-08-29	Reinigungsverfahren
DE3880566T2 (de)	1993-12-09	Verfahren zur Isomerisierung von trans-2-Methylspiro-(1,3-oxathiolan-5,3')-chinuklidin oder Säureadditionsalzen davon.
DE2745280C2 (de)	1986-02-06	3-Cyano-10,11-dihydro-5H-dibenz[b,f]azepin
DE3104883C2 (de)	1984-11-15	Benzylidenderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2138122B2 (de)	1978-10-05	Verfahren zur Gewinnung von D-Penicillamin
EP0001060A1 (de)	1979-03-21	Verfahren zur Herstellung von optisch aktiver, ggf. substituierter 2-Amino-2-phenylessigsäure
DE3586149T2 (de)	1992-12-03	Verfahren zur spaltung von (+/-)-2-(2'-(p-fluorphenyl)-5'-benzoxazolyl)-propionsaeure.
DE69011996T2 (de)	1995-02-02	Verfahren zur Herstellung von 1,4-Dihydroxy-2-arylnaphthoat.
DE3734219C2 (he)	1989-11-16
DE2928022A1 (de)	1980-01-31	Verfahren zur herstellung des 2-(n- benzyl-n-methylamino)-aethylesters der 2,6- dimethyl-4-(3-nitrophenyl)-3-methoxycarbonyl-1,4-dihydropyridin-5-carbonsaeure
DE1493966C3 (de)	1976-04-29	Verfahren zur Herstellung der L-bzw. D-Form der N-Acetylverbindung des alpha- Vanillyl-alpha-aminopropionitrils
AT282586B (de)	1970-07-10	Verfahren zur herstellung von neuem racemischem oder optisch aktivem (1-2'-nitrilophenoxy)-2-hydroxy-3-isopropylaminopropan und dessen salzen
DE69301324T2 (de)	1996-09-05	Verfahren zur Herstellung optisch aktivem 4-Hydroxy-2-Cyclopentenon
DD285341B5 (de)	1993-08-26	Verfahren zur herstellung der reinen enantiomeren des 1-(4-nitrophenoxy)-2-hydroxy-3-tert.-butylaminopropan und ihrer salze