SU1709908A3 - Способ получени производных 1,5-бензотиазепина или их фармацевтически приемлемых кислотно-аддитивных солей - Google Patents

Способ получени производных 1,5-бензотиазепина или их фармацевтически приемлемых кислотно-аддитивных солей Download PDF

Info

Publication number: SU1709908A3
Authority: SU; USSR - Soviet Union
Prior art keywords: compound; lower alkyl; cis; compounds; dihydro
Prior art date: 1987-08-12

Application number

SU884356317A

Other languages

English (en)

Russian (ru)

Inventor

Иноуе Хирозуми

Харада Тсунехиро

Нагасава Масааки

Original Assignee

Танабе Сейяку Ко, Лтд (Фирма)

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.)

1987-08-12

Filing date

1988-08-11

Publication date

1992-01-30

1988-08-11 Application filed by Танабе Сейяку Ко, Лтд (Фирма) filed Critical Танабе Сейяку Ко, Лтд (Фирма)

1992-01-30 Application granted granted Critical

1992-01-30 Publication of SU1709908A3 publication Critical patent/SU1709908A3/ru

Links

150000003839 salts Chemical class 0.000 title claims abstract description 6
238000000034 method Methods 0.000 title claims description 13
239000000654 additive Substances 0.000 title 1
230000015572 biosynthetic process Effects 0.000 title 1
238000003786 synthesis reaction Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 56
230000000694 effects Effects 0.000 claims abstract description 12
239000002904 solvent Substances 0.000 claims abstract description 8
239000002253 acid Substances 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract 5
229910052736 halogen Inorganic materials 0.000 claims abstract 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
239000001257 hydrogen Substances 0.000 claims abstract 4
125000003545 alkoxy group Chemical group 0.000 claims abstract 3
150000002367 halogens Chemical group 0.000 claims abstract 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 2
150000001412 amines Chemical class 0.000 claims abstract 2
125000001589 carboacyl group Chemical group 0.000 claims abstract 2
239000003814 drug Substances 0.000 claims abstract 2
229960004166 diltiazem Drugs 0.000 claims description 9
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 claims description 8
230000017531 blood circulation Effects 0.000 claims description 7
230000002490 cerebral effect Effects 0.000 claims description 7
KJFRSZASZNLCDF-UHFFFAOYSA-N 1,5-benzothiazepine Chemical class S1C=CC=NC2=CC=CC=C12 KJFRSZASZNLCDF-UHFFFAOYSA-N 0.000 claims description 3
241000700159 Rattus Species 0.000 claims description 3
229940125898 compound 5 Drugs 0.000 claims description 3
239000003218 coronary vasodilator agent Substances 0.000 claims description 3
239000002220 antihypertensive agent Substances 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 claims 1
230000003993 interaction Effects 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
239000013078 crystal Substances 0.000 abstract description 3
229940124549 vasodilator Drugs 0.000 abstract description 3
239000003071 vasodilator agent Substances 0.000 abstract description 3
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208000014644 Brain disease Diseases 0.000 abstract description 2
206010061216 Infarction Diseases 0.000 abstract description 2
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230000007574 infarction Effects 0.000 abstract description 2
230000000144 pharmacologic effect Effects 0.000 abstract description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 2
FHGWEHGZBUBQKL-UHFFFAOYSA-N 1,2-benzothiazepine Chemical compound S1N=CC=CC2=CC=CC=C12 FHGWEHGZBUBQKL-UHFFFAOYSA-N 0.000 abstract 1
239000013543 active substance Substances 0.000 abstract 1
238000005576 amination reaction Methods 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
238000002955 isolation Methods 0.000 abstract 1
231100000053 low toxicity Toxicity 0.000 abstract 1
238000002360 preparation method Methods 0.000 abstract 1
239000000126 substance Substances 0.000 abstract 1
230000009466 transformation Effects 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
230000001077 hypotensive effect Effects 0.000 description 12
238000001953 recrystallisation Methods 0.000 description 11
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
-1 (+) - cis-2 - (- methoxyphenyl) -3 hydroxy-8-chloro-2,3-dihydro-1, 5-benzothiazepine Chemical compound 0.000 description 8
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 8
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
230000000304 vasodilatating effect Effects 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
230000036772 blood pressure Effects 0.000 description 6
229940125904 compound 1 Drugs 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
210000001367 artery Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
206010008118 cerebral infarction Diseases 0.000 description 2
SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical group ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 2
210000004351 coronary vessel Anatomy 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
229960001412 pentobarbital Drugs 0.000 description 2
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
OLQNRIOMNSJXDF-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-8-methyl-3,5-dihydro-2H-1,5-benzothiazepin-4-one Chemical compound CN(CCC1SC2=C(NC(C1)=O)C=CC(=C2)C)C OLQNRIOMNSJXDF-UHFFFAOYSA-N 0.000 description 1
FMMYTRQXHORTCU-UHFFFAOYSA-N 2-chloroethyl methanesulfonate Chemical compound CS(=O)(=O)OCCCl FMMYTRQXHORTCU-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
PPQXADXGECUTFI-UHFFFAOYSA-N 5h-1,5-benzothiazepin-4-one Chemical compound S1C=CC(=O)NC2=CC=CC=C21 PPQXADXGECUTFI-UHFFFAOYSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
201000006474 Brain Ischemia Diseases 0.000 description 1
206010008120 Cerebral ischaemia Diseases 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
150000007657 benzothiazepines Chemical class 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical group CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000008602 contraction Effects 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
238000001035 drying Methods 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
239000008103 glucose Substances 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000013641 positive control Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
HHAVHBDPWSUKHZ-UHFFFAOYSA-N propan-2-ol;propan-2-one Chemical compound CC(C)O.CC(C)=O HHAVHBDPWSUKHZ-UHFFFAOYSA-N 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
210000002385 vertebral artery Anatomy 0.000 description 1
238000005406 washing 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU884356317A 1987-08-12 1988-08-11 Способ получени производных 1,5-бензотиазепина или их фармацевтически приемлемых кислотно-аддитивных солей SU1709908A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP62202027A JPS6445376A (en)	1987-08-12	1987-08-12	Production of 1,5-benzothiazepine derivative

Publications (1)

Publication Number	Publication Date
SU1709908A3 true SU1709908A3 (ru)	1992-01-30

Family

ID=16450708

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU884356317A SU1709908A3 (ru)	1987-08-12	1988-08-11	Способ получени производных 1,5-бензотиазепина или их фармацевтически приемлемых кислотно-аддитивных солей

Country Status (14)

Country	Link
JP (1)	JPS6445376A (de)
KR (1)	KR890003722A (de)
CN (1)	CN1030570C (de)
AT (1)	AT395010B (de)
BG (1)	BG50501A3 (de)
CA (1)	CA1337346C (de)
ES (1)	ES2007990A6 (de)
FI (1)	FI883115A7 (de)
GR (1)	GR1000385B (de)
IE (1)	IE61168B1 (de)
IL (1)	IL86978A0 (de)
NO (1)	NO170017C (de)
PT (1)	PT88250B (de)
SU (1)	SU1709908A3 (de)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1236467A (en) *	1967-10-28	1971-06-23	Tanabe Seiyaku Co	Benzothiazepine derivatives
US3895006A (en) *	1974-04-19	1975-07-15	Squibb & Sons Inc	5-(Substituted amino)alkyl)-2-aryl-3-halo-1,5-benzothiazepin-4(5H)-ones
SE449611B (sv) *	1982-07-09	1987-05-11	Tanabe Seiyaku Co	Sett att framstella 1,5-bensotiazepinderivat
GB8315364D0 (en) *	1983-06-03	1983-07-06	Tanabe Seiyaku Co	8-chloro-1 5-benzothiazepine derivatives
US4567175A (en) *	1983-06-03	1986-01-28	Tanabe Seiyaku Co., Ltd.	8-Chloro-1,5-benzothiazepine derivatives
GB8406318D0 (en) *	1984-03-10	1984-04-11	Tanabe Seiyaku Co	1 5-benzothiazepine derivatives
JPS60204776A (ja) *	1984-03-30	1985-10-16	Roller Japan Kk	１，５−ベンゾチアゼピン誘導体
JPS61103877A (ja) *	1984-10-24	1986-05-22	Tanabe Seiyaku Co Ltd	ベンゾチアゼピン誘導体及びその製法

1987
- 1987-08-12 JP JP62202027A patent/JPS6445376A/ja active Pending
1988
- 1988-06-27 IE IE194988A patent/IE61168B1/en not_active IP Right Cessation
- 1988-06-29 FI FI883115A patent/FI883115A7/fi not_active Application Discontinuation
- 1988-07-04 IL IL86978A patent/IL86978A0/xx not_active IP Right Cessation
- 1988-07-07 CA CA000571438A patent/CA1337346C/en not_active Expired - Fee Related
- 1988-07-11 CN CN88104387A patent/CN1030570C/zh not_active Expired - Fee Related
- 1988-08-02 BG BG085116A patent/BG50501A3/xx unknown
- 1988-08-04 GR GR880100515A patent/GR1000385B/el unknown
- 1988-08-09 NO NO883525A patent/NO170017C/no unknown
- 1988-08-10 KR KR1019880010209A patent/KR890003722A/ko not_active Ceased
- 1988-08-11 ES ES8802522A patent/ES2007990A6/es not_active Expired
- 1988-08-11 PT PT88250A patent/PT88250B/pt not_active IP Right Cessation
- 1988-08-11 SU SU884356317A patent/SU1709908A3/ru active
- 1988-08-11 AT AT0202388A patent/AT395010B/de not_active IP Right Cessation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Патент GB ff 1236'»67, кл. С 07 d 93/04, опублик. 1971.(^k) СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ 1,5-БЕНЗОТИАЗЕПИНА ИЛИ ИХ ФАРМАЦЕВТИЧЕСКИ ПРИЕМЛЕМЫХ КИСЛОТНО-А,Г1ДИТИВНЫХ СОЛЕЙ *

Also Published As

Publication number	Publication date
GR1000385B (el)	1992-06-30
IE881949L (en)	1989-02-12
NO883525D0 (no)	1988-08-09
NO170017C (no)	1992-09-02
KR890003722A (ko)	1989-04-17
PT88250A (pt)	1989-06-30
IE61168B1 (en)	1994-10-05
NO883525L (no)	1989-02-13
GR880100515A (en)	1989-05-25
ATA202388A (de)	1992-01-15
NO170017B (no)	1992-05-25
ES2007990A6 (es)	1989-07-01
JPS6445376A (en)	1989-02-17
CN1030570C (zh)	1995-12-27
PT88250B (pt)	1995-03-01
FI883115A7 (fi)	1989-02-13
BG50501A3 (bg)	1992-08-14
CN1031229A (zh)	1989-02-22
IL86978A0 (en)	1988-12-30
FI883115A0 (fi)	1988-06-29
AT395010B (de)	1992-08-25
CA1337346C (en)	1995-10-17

Publication	Publication Date	Title
SU1362401A3 (ru)	1987-12-23	Способ получени производных 8-хлор-1,5-бензотиазепина или их фармацевтически приемлемых аддитивных солей кислот
EP0154838B1 (de)	1988-07-06	1,5-Benzothiazepinderivate, Verfahren zu ihrer Herstellung und Arzneimittel
US4585768A (en)	1986-04-29	1,5-benzothiazepine derivatives and processes for preparing the same
FI80881C (fi)	1990-08-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1,5-bentsotiazepinderivat.
JPH02288828A (ja)	1990-11-28	医薬組成物
DK171821B1 (da)	1997-06-23	9-chlor-1,5-benzothiazepinderivater, fremgangsmåde til fremstilling deraf samt farmaceutisk præparat indeholdende disse
JPS6313994B2 (de)	1988-03-29
SU1709908A3 (ru)	1992-01-30	Способ получени производных 1,5-бензотиазепина или их фармацевтически приемлемых кислотно-аддитивных солей
EP0128462B1 (de)	1989-03-22	Benzothiazepinderivate, Verfahren zur Herstellung und pharmazeutische Zusammensetzungen
EP0158340B1 (de)	1989-01-18	1,5-Benzothiazepinderivate, Verfahren zu ihrer Herstellung und Arzneimittel
FI85976B (fi)	1992-03-13	Foerfarande foer framstaellning av farmakologiskt vaerdefullt naftotiazepinderivat.
SU1544187A3 (ru)	1990-02-15	Способ получени производных 1,5-бензотиазепина или их солей
JPS60178870A (ja)	1985-09-12	１，５‐ベンゾチアゼピン誘導体及びその製法
JPS6313966B2 (de)	1988-03-29
RU1784041C (ru)	1992-12-23	Способ получени производных 1,5-бензотиазепина или их фармацевтически приемлемых кислотно-аддитивных солей
JPH0421668B2 (de)	1992-04-13
JPH0621071B2 (ja)	1994-03-23	血小板凝集抑制剤
FI91965C (fi)	1994-09-12	Menetelmä 1,5-bentsotiatsepiinijohdannaisen fenolisen hydroksiryhmän alkyloimiseksi lähtöaineen rasemoitumatta
JPH0376290B2 (de)	1991-12-05