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GB1331015A - 1-substituted-6-phenyl-4h-s-triazolo-4,3-a-1,4-benzodiazepines - Google Patents

1-substituted-6-phenyl-4h-s-triazolo-4,3-a-1,4-benzodiazepines

Info

Publication number
GB1331015A
GB1331015A GB1487972A GB1487972A GB1331015A GB 1331015 A GB1331015 A GB 1331015A GB 1487972 A GB1487972 A GB 1487972A GB 1487972 A GB1487972 A GB 1487972A GB 1331015 A GB1331015 A GB 1331015A
Authority
GB
United Kingdom
Prior art keywords
alkyl
coor
cyano
hydroxy
iii
Prior art date
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
GB1487972A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn 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.)
Filing date
Publication date
Application filed by Upjohn Co filed Critical Upjohn Co
Publication of GB1331015A publication Critical patent/GB1331015A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

1331015 1 - Substituted - 6 - phenyl - 4H - striazolo[4,3-a][1,4]benzodiazepines UPJOHN CO 29 March 1972 [28 April 1971 22 Nov 1971] 14879/72 Heading C2C Novel compounds of the Formula III: wherein R is cyano, hydroxy, nitro, di-(C 1-3 alkyl)amino C 1-3 alkoxy, or alkylthio or COOR<SP>11</SP>, wherein R<SP>11</SP> is C 1-3 alkyl; R 1 is hydrogen or C 1-3 alkyl, and R 2 , R 3 , R 4 , and R 5 are hydrogen, C 1-3 alkyl, halogen, nitro, cyano, trifluoromethyl, or C 1-3 alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, di-(C 1-3 alkyl), amino or alkanoylamino in which the carbon chain moiety has 1 to 3 carbon atoms, and pharmacologically acceptable acid addition salts and when R is hydroxy, esters thereof may be prepared where R is other than COOR<SP>11</SP> by reacting a compound of the Formula I: with a hydrazide RCH 2 CONHNH 2 , where R is other than COOR<SP>11</SP>, and optionally hydrolysing the cyclized product in which R is cyano with R<SP>11</SP>OH and hydrochloric acid to produce the compound III in which R is COOR<SP>11</SP> and where R is hydroxy optionally esterifying the hydroxyl group. The intermediates I may be prepared by reacting the corresponding 2-oxo compound with phosphorus pentasulphide. Pharmaceutical compositions of the compounds III show sedative, tranquilizing and muscle relaxant activity when administered orally, parenterally or rectally with the usual excipients. The trichloroacetate salts of the compounds III are useful as herbicides against Johnson grass, Bermuda grass, yellow foxtail, green foxtail and quack grass.
GB1487972A 1971-04-28 1972-03-29 1-substituted-6-phenyl-4h-s-triazolo-4,3-a-1,4-benzodiazepines Expired GB1331015A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US13827871A 1971-04-28 1971-04-28
US20120771A 1971-11-22 1971-11-22

Publications (1)

Publication Number Publication Date
GB1331015A true GB1331015A (en) 1973-09-19

Family

ID=26836045

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1487972A Expired GB1331015A (en) 1971-04-28 1972-03-29 1-substituted-6-phenyl-4h-s-triazolo-4,3-a-1,4-benzodiazepines

Country Status (7)

Country Link
JP (1) JPS5541235B1 (en)
BE (1) BE782680A (en)
CH (1) CH571518A5 (en)
DE (1) DE2220615A1 (en)
FR (1) FR2134625B1 (en)
GB (1) GB1331015A (en)
NL (2) NL7205705A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004320A1 (en) * 1978-03-09 1979-10-03 Shionogi & Co., Ltd. 1-Substituted-thiomethyltriazolobenzodiazepines, preparation thereof, their use, and a pharmaceutical composition
US4455307A (en) * 1982-01-04 1984-06-19 The Upjohn Company Antihypertensive use of triazolobenzodiazepines
US4476134A (en) * 1983-08-01 1984-10-09 The Upjohn Company Process for treating panic disorders
US4588721A (en) * 1983-09-12 1986-05-13 The Upjohn Company Treatment of negative symptoms of schizophrenia

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4902794A (en) * 1971-04-28 1990-02-20 The Upjohn Company Triazolo-benzodiazepines
DE3332830A1 (en) * 1982-09-16 1984-03-22 The Upjohn Co., 49001 Kalamazoo, Mich. USE OF BENZODIAZEPINES TO COMBAT OR TREAT PANIC CONDITIONS
JPS6144523A (en) * 1984-08-06 1986-03-04 Nippon Steel Corp billet cutting equipment
JPS61100311A (en) * 1984-10-18 1986-05-19 Kawasaki Steel Corp Cutting device in welder

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3987052A (en) * 1969-03-17 1976-10-19 The Upjohn Company 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines
JPS4932874B1 (en) * 1970-12-11 1974-09-03

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004320A1 (en) * 1978-03-09 1979-10-03 Shionogi & Co., Ltd. 1-Substituted-thiomethyltriazolobenzodiazepines, preparation thereof, their use, and a pharmaceutical composition
US4455307A (en) * 1982-01-04 1984-06-19 The Upjohn Company Antihypertensive use of triazolobenzodiazepines
US4476134A (en) * 1983-08-01 1984-10-09 The Upjohn Company Process for treating panic disorders
US4588721A (en) * 1983-09-12 1986-05-13 The Upjohn Company Treatment of negative symptoms of schizophrenia

Also Published As

Publication number Publication date
DE2220615A1 (en) 1972-11-16
BE782680A (en) 1972-10-26
FR2134625A1 (en) 1972-12-08
FR2134625B1 (en) 1975-10-17
NL7205705A (en) 1972-10-31
NL8105804A (en) 1982-04-01
CH571518A5 (en) 1976-01-15
JPS5541235B1 (en) 1980-10-22

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Legal Events

Date Code Title Description
PS Patent sealed
48S Specification amended (sect. 8/1949)
SPA Amended specification published
PE20 Patent expired after termination of 20 years