CA1066274A - 6-aryl-4h-s-triazolo- (3,4c) -thieno- (2,3e) -1,4-diazepines substituees et procedes pour leur production - Google Patents

6-aryl-4h-s-triazolo- (3,4c) -thieno- (2,3e) -1,4-diazepines substituees et procedes pour leur production

Info

Publication number: CA1066274A
Authority: CA; Canada
Prior art keywords: formula; thieno; diazepine; bromo; methyl
Prior art date: 1974-03-02
Legal status (The legal status 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 status listed.): Expired

Application number

CA220,982A

Other languages

English (en)

Other versions

CA220982S (en

Inventor

Franz J. Kuhn

Adolf Bauer

Karl-Heinz Weber

Peter Danneberg

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim GmbH

Original Assignee

Boehringer Ingelheim GmbH

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.)

1974-03-02

Filing date

1975-02-28

Publication date

1979-11-13

1975-02-28 Application filed by Boehringer Ingelheim GmbH filed Critical Boehringer Ingelheim GmbH

1979-11-13 Application granted granted Critical

1979-11-13 Publication of CA1066274A publication Critical patent/CA1066274A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 23
238000004519 manufacturing process Methods 0.000 title claims 2
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239000002253 acid Substances 0.000 claims abstract description 29
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239000000460 chlorine Chemical group 0.000 claims abstract description 13
229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
231100000252 nontoxic Toxicity 0.000 claims abstract description 10
230000003000 nontoxic effect Effects 0.000 claims abstract description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052794 bromium Inorganic materials 0.000 claims abstract description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
239000011737 fluorine Chemical group 0.000 claims abstract description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
238000002360 preparation method Methods 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000007858 starting material Substances 0.000 claims description 8
NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 4
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IDNISMFGEJLNFN-UHFFFAOYSA-N 8-bromo-6-(o-bromophenyl)-1-methyl-4h-s-triazolo(3,4c)thieno(2,3e)-1,4-diazepine Chemical compound C1=2C=C(Br)SC=2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Br IDNISMFGEJLNFN-UHFFFAOYSA-N 0.000 claims description 3
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229910052736 halogen Inorganic materials 0.000 claims description 2
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VOZDBDBHBXLWCG-UHFFFAOYSA-N 2-bromo-4-(2-fluorophenyl)-9-methyl-6h-thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepine Chemical compound C1=2C=C(Br)SC=2N2C(C)=NN=C2CN=C1C1=CC=CC=C1F VOZDBDBHBXLWCG-UHFFFAOYSA-N 0.000 claims 2
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239000003054 catalyst Substances 0.000 description 4
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XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA220,982A 1974-03-02 1975-02-28 6-aryl-4h-s-triazolo- (3,4c) -thieno- (2,3e) -1,4-diazepines substituees et procedes pour leur production Expired CA1066274A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2410030A DE2410030C3 (de)	1974-03-02	1974-03-02	8-Brom-6-phenyl-4H-s-triazolo[3,4-c]thieno[2,3-e]1,4-diazepine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen

Publications (1)

Publication Number	Publication Date
CA1066274A true CA1066274A (fr)	1979-11-13

Family

ID=5908899

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA220,982A Expired CA1066274A (fr)	1974-03-02	1975-02-28	6-aryl-4h-s-triazolo- (3,4c) -thieno- (2,3e) -1,4-diazepines substituees et procedes pour leur production

Country Status (9)

Country	Link
CA (1)	CA1066274A (fr)
DE (1)	DE2410030C3 (fr)
GB (1)	GB1490269A (fr)
HK (1)	HK45981A (fr)
IL (1)	IL46730A (fr)
IT (1)	IT8047553A0 (fr)
MY (1)	MY8100030A (fr)
NZ (1)	NZ176793A (fr)
ZA (1)	ZA751246B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2001122785A (ja) *	1999-10-22	2001-05-08	Nippon Boehringer Ingelheim Co Ltd	ブロチゾラムを含有する錠剤

1974
- 1974-03-02 DE DE2410030A patent/DE2410030C3/de not_active Expired
1975
- 1975-02-28 IL IL46730A patent/IL46730A/xx unknown
- 1975-02-28 NZ NZ176793A patent/NZ176793A/xx unknown
- 1975-02-28 ZA ZA751246A patent/ZA751246B/xx unknown
- 1975-02-28 CA CA220,982A patent/CA1066274A/fr not_active Expired
- 1975-03-03 GB GB8756/75A patent/GB1490269A/en not_active Expired
1980
- 1980-01-09 IT IT8047553A patent/IT8047553A0/it unknown
1981
- 1981-09-10 HK HK459/81A patent/HK45981A/xx unknown
- 1981-12-30 MY MY30/81A patent/MY8100030A/xx unknown

Also Published As

Publication number	Publication date
IT8047553A0 (it)	1980-01-09
ZA751246B (en)	1977-09-28
NZ176793A (en)	1978-04-03
IL46730A (en)	1981-06-29
GB1490269A (en)	1977-10-26
DE2410030A1 (de)	1975-10-02
MY8100030A (en)	1981-12-31
AU7864875A (en)	1976-09-02
DE2410030C3 (de)	1982-11-11
DE2410030B2 (de)	1976-05-06
HK45981A (en)	1981-09-18

Publication	Publication Date	Title
US4585771A (en)	1986-04-29	Antiinflammatory imidazole derivatives
US3407211A (en)	1968-10-22	Acylaminophenyl heterocyclic ketones
US4094984A (en)	1978-06-13	6-Phenyl-8-bromo-4H-s-triazolo-[3,4C]-thieno-[2,3E]-1,4-diazepines and salts thereof
DE2249644A1 (de)	1973-04-19	Neue organische verbindungen und verfahren zu deren herstellung
JPH07103127B2 (ja)	1995-11-08	チエノートリアゾロ―ジアゼピン誘導体、その製造法及びそれを含有する抗喘息、抗アレルギー剤
JPH06104668B2 (ja)	1994-12-21	チエノ‐トリアゾロ‐ジアゼピンのチオメチル誘導体、その製造方法及びそれを含有する医薬組成物
US3904641A (en)	1975-09-09	Triazolothienodiazepine compounds
CA1066274A (fr)	1979-11-13	6-aryl-4h-s-triazolo- (3,4c) -thieno- (2,3e) -1,4-diazepines substituees et procedes pour leur production
USRE28972E (en)	1976-09-21	5-Aryl-1H-1,5-benzodiazepine-2,4-diones
CA1049009A (fr)	1979-02-20	6h-thieno (3,2-f)-s-triazolo (4,3-a) (1,4) diazepines
US3520901A (en)	1970-07-21	Tetrahydroindazoles
Hino et al.	1988	Agents Acting on the Central Nervous System.: Synthesis of 3-Phenyl-2-piperazinyl-1-benzazocines, 3-Substituted-2-piperazinyl-1-benzazepines and Related Compounds
US3849405A (en)	1974-11-19	Thieno-(2,3-e)(1,4)diazepin-2-ones
KR850000452B1 (ko)	1985-04-05	카바모일옥시아미노-1, 4-벤조디아제핀의 제조방법
US4167570A (en)	1979-09-11	2-Methyl-6-alkyl-11-aminoalkyl-6,11-dihydro-5H-pyrido(2,3-B)(1,5)benzodiazepin-5-ones and salts thereof
US4263310A (en)	1981-04-21	8-Bromo-6-(o-chloro-phenyl)-4H-S-triazolo-[3,4,-c]-thieno-[2,3-e]-1,4-diazepines and salts thereof
US4344946A (en)	1982-08-17	2,6-Diamino-benzo[1,2-d:5,4-d']bisthiazoles and salts thereof
US4116956A (en)	1978-09-26	Benzodiazepine derivatives
US4269774A (en)	1981-05-26	Thiazolo[5,4-d][2]benzazepines
CA1070301A (fr)	1980-01-22	Les triazolothienodiazepine-1-ones, procedes pour leur production et produits pharmaceutiques derives
US3890321A (en)	1975-06-17	6-aryl-5-ethyl-pyrimidin-4-ol compounds useful as intermediates and bronchodilators
KR800000088B1 (ko)	1980-01-30	치환된 6-아릴-4H-s-트리아졸로-[3, 4c]-티에노-[2, 3e]-1, 4-디아제핀의 제조방법
US3721666A (en)	1973-03-20	1-(phenyl or pyridyl)-4-(alkyl or alkenyl)-3h-1,4-benzodiazepine-2,5-(1h,4h)-diones
US4321199A (en)	1982-03-23	Thiazolo[5,4-d][2] benzazepines and intermediates
US4154843A (en)	1979-05-15	Method of treating psychotic states with 1-acyl-3(5)-alkyl-5(3)-phenyl-1,2,4-triazoles