GB1268607A – NEW PYRAZOLO[3,4-e][1,4]DIAZEPIN-7(1H)-ONE COMPOUNDS AND METHODS FOR THEIR PRODUCTION
– Google Patents
GB1268607A – NEW PYRAZOLO[3,4-e][1,4]DIAZEPIN-7(1H)-ONE COMPOUNDS AND METHODS FOR THEIR PRODUCTION
– Google Patents
NEW PYRAZOLO[3,4-e][1,4]DIAZEPIN-7(1H)-ONE COMPOUNDS AND METHODS FOR THEIR PRODUCTION
Info
Publication number
GB1268607A
GB1268607A
GB23086/70A
GB2308670A
GB1268607A
GB 1268607 A
GB1268607 A
GB 1268607A
GB 23086/70 A
GB23086/70 A
GB 23086/70A
GB 2308670 A
GB2308670 A
GB 2308670A
GB 1268607 A
GB1268607 A
GB 1268607A
Authority
GB
United Kingdom
Prior art keywords
formula
reacting
compound
prepared
compounds
Prior art date
1969-05-14
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
GB23086/70A
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.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co LLC
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.)
1969-05-14
Filing date
1970-05-13
Publication date
1972-03-29
1970-05-13
Application filed by Parke Davis and Co LLC
filed
Critical
Parke Davis and Co LLC
1972-03-29
Publication of GB1268607A
publication
Critical
patent/GB1268607A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
C07D231/38—Nitrogen atoms
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
C07D231/16—Halogen atoms or nitro radicals
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
C07D231/18—One oxygen or sulfur atom
C07D231/20—One oxygen atom attached in position 3 or 5
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
C07D231/38—Nitrogen atoms
C07D231/40—Acylated on said nitrogen atom
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
Abstract
1,268,607. Pyrazolodiazepines. PARKE DAVIS & CO. 13 May, 1970 [14 May, 1969], No. 23086/70. Heading C2C. Novel compounds of Formula I (in which R 1 is CH 3 or C 2 H 5 , R 2 is Cl or C 1-3 alkyl, R 3 is H or CH 3 and Ar is phenyl, ofluorophenyl or o-chlorophenyl) and pharmaceutically acceptable salts thereof, are prepared by (a) reacting a compound of Formula II with hydrazine, or (b) reacting a compound of Formula III (in which Z is Br, Cl, I or alkyl- or aryl-sulphonyloxy) or a salt thereof, with ammonia, or (c) cyclizing a compound (which may be prepared in situ) of Formula IV or (d) (for Compounds I in which R 3 is H and R 2 is C 1-3 alkyl) reacting a compound of Formula V (in which R 4 is C 1-3 alkyl) with a compound of formula X-CH 2 -CO-X 1 (in which X is Cl, Br or I and X 1 is Br or Cl) optionally followed in each case by methylation of Compounds I in which R 3 is H, and/or by salt formation. Compounds of Formula II are prepared by reacting a compound of Formula VI with phthalimidoacetyl chloride in an unreactive solvent. Compounds of Formula III are prepared by reacting a compound of Formula VI with a compound of formula X-CH 2 -CO-X 1 or with a 2-(alkyl- or aryl-sulphonyloxy)acetyl chloride. Compounds of Formula IV are prepared by reducing a compound of Formula VII which are themselves prepared by reacting a compound of Formula III (in which Z is Cl, Br or I) with sodium azide in an unreactive solvent medium, and optionally methylating the product. Compounds of Formula V are prepared by reacting a compound of, Formula VIII with a compound of Formula Ar-M (in which M is Li or MgBr) and hydrolyzing the reaction product under mild neutral conditions. Compounds of Formula III.-Those compounds in which R 2 is C 1-3 alkyl are prepared by reacting a compound of formula R 1 -NHNH 2 with a compound of formula to produce a 1-R 1 -3-R 4 -5-pyrazolone, reacting this with POCl 3 to produce a 1-R 1 -3-R 4 -5- chloropyrazole, reacting this with an aroyl chloride Ar-COCl to produce a 1-R 1 -3-R 4 -4- aroylpyrazole and reacting this with an amine R 3 NH 2 . Those compounds in which R 2 is Cl are prepared by reacting a 1-R 1 -3-hydroxy-5- aminopyrazole with an acid Ar-COOH in polyphosphoric acid to produce a 1-R 1 -3- hydroxy-4-aroyl-5-arylamidopyrazole, reacting this with POCl 3 to produce a 1-R 1 -3-chloro-4- aroyl-5-arylamido pyrazole, and hydrolysing this, optionally after methylation, with HBr in acetic acid. 5 – Amino – 4 – benzoyl – 1,3 – dimethylpyrazole and 5-amino-4-benzoyl-1-methyl-3-ethylpyrazole are also prepared by reacting 5-amino- 4-cyano-1,3-dimethylpyrazole or 5-amino-4-cyano-3-ethyl-1-methylpyrazole with phenyl lithium and hydrolysing the product. 5-(Methylamino) – 4 – (o – fluorobenzoyl) – 1,3 – dimethylpyrazole is also prepared by reacting 5-amino- 1,3-dimethylpyrazole with o-fluorobenzoyl chloride to produce 5-(o-fluorobenzamido)-4-(o-fluorobenzoyl)-1,3-dimethylpyrazole, reacting this with methyl iodide to produce 4-(o-fluorobenzoyl)-1,3- dimethyl-5-(N-methyl-o-fluorobenzamido)pyrazole and hydrolysing this with hydrobromic acid. 5- Amino – 3 – ethyl – 4 – (o – fluorobenzoyl) – 1- methylpyrazole is prepared similarly but without the methylation step. Pharmaceutical compositions having central nervous system depressant activity, for oral or parenteral administration, comprise a compound of Formula I together with a pharmaceutical carrier.
GB23086/70A
1969-05-14
1970-05-13
NEW PYRAZOLO[3,4-e][1,4]DIAZEPIN-7(1H)-ONE COMPOUNDS AND METHODS FOR THEIR PRODUCTION
Expired
GB1268607A
(en)
Applications Claiming Priority (2)
Application Number
Priority Date
Filing Date
Title
US82468769A
1969-05-14
1969-05-14
US2401270A
1970-03-30
1970-03-30
Publications (1)
Publication Number
Publication Date
GB1268607A
true
GB1268607A
(en)
1972-03-29
Family
ID=26697913
Family Applications (2)
Application Number
Title
Priority Date
Filing Date
GB23088/70A
Expired
GB1268608A
(en)
1969-05-14
1970-05-13
5-amino-4-aroyl-1,3-dialkylpyrazoles
GB23086/70A
Expired
GB1268607A
(en)
1969-05-14
1970-05-13
NEW PYRAZOLO[3,4-e][1,4]DIAZEPIN-7(1H)-ONE COMPOUNDS AND METHODS FOR THEIR PRODUCTION
Family Applications Before (1)
Application Number
Title
Priority Date
Filing Date
GB23088/70A
Expired
GB1268608A
(en)
1969-05-14
1970-05-13
5-amino-4-aroyl-1,3-dialkylpyrazoles
Country Status (9)
Country
Link
US
(2)
US3558605A
(en)
AT
(4)
AT298500B
(en)
BE
(1)
BE750367A
(en)
CH
(4)
CH510040A
(en)
DE
(1)
DE2023453C3
(en)
FR
(1)
FR2051523B1
(en)
GB
(2)
GB1268608A
(en)
NL
(1)
NL148320B
(en)
SE
(1)
SE380016B
(en)
Families Citing this family (12)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
FR2184392A1
(en)
*
1972-05-15
1973-12-28
Abbott Lab
1,3-dimethyl-5-methylamino-8-phenylpyrazolo (4,3-e)(1,4)diazepine-ant
US3823157A
(en)
*
1972-12-15
1974-07-09
Wald H De
Pyrazolodiazepine compounds and methods for their production
US3879535A
(en)
*
1973-02-20
1975-04-22
Parke Davis & Co
Anesthetic compositions and methods of use
US3873565A
(en)
*
1973-05-16
1975-03-25
Parke Davis & Co
Pyrazolodiazocine compounds
DE2747531A1
(en)
*
1977-10-22
1979-04-26
Basf Ag
SUBSTITUTED 3-AMINOPYRAZOLE
DE2932835A1
(en)
*
1979-08-14
1981-03-26
Hoechst Ag, 65929 Frankfurt
NEW 4-ARYL-5,6,7,8-TETRAHYDROPYRAZOLO (3,4-B) DIAZEPINE-1H, 4H-5,7-DIONE AND METHOD FOR ITS REPRESENTATION
ES8305350A1
(en)
*
1981-06-26
1983-04-01
Warner Lambert Co
Basic acyl amides of (5-amino-1,3-dialkylpyrazol-4-yl)(aryl)methanones, processes for their production, and pharmaceutical compositions containing such compounds.
US4980472A
(en)
*
1983-06-23
1990-12-25
American Cyanamid Company
Method of making (3-amino-1H-pyrazol-4-yl) (aryl)methanones
NZ208555A
(en)
*
1983-06-23
1987-06-30
American Cyanamid Co
(3-amino-1h-pyrazol-4-yl)-arylmethanone derivatives
US4900836A
(en)
*
1983-06-23
1990-02-13
American Cyanamid Company
(3-amino-1H-pyrazol-4-yl) (aryl)methanones
DE4314851A1
(en)
*
1993-05-05
1994-11-10
Huels Chemische Werke Ag
Process for the preparation of 3-amino-5-methylpyrazole
US6316466B1
(en)
*
1998-05-05
2001-11-13
Syntex (U.S.A.) Llc
Pyrazole derivatives P-38 MAP kinase inhibitors
1969
1969-05-14
US
US824687A
patent/US3558605A/en
not_active
Expired – Lifetime
1970
1970-03-30
US
US24012A
patent/US3660425A/en
not_active
Expired – Lifetime
1970-05-13
CH
CH711170A
patent/CH510040A/en
not_active
IP Right Cessation
1970-05-13
SE
SE7006517A
patent/SE380016B/xx
unknown
1970-05-13
AT
AT463171A
patent/AT298500B/en
not_active
IP Right Cessation
1970-05-13
NL
NL707006933A
patent/NL148320B/en
not_active
IP Right Cessation
1970-05-13
DE
DE2023453A
patent/DE2023453C3/en
not_active
Expired
1970-05-13
AT
AT430570A
patent/AT297709B/en
not_active
IP Right Cessation
1970-05-13
CH
CH756571A
patent/CH522665A/en
not_active
IP Right Cessation
1970-05-13
CH
CH756471A
patent/CH522664A/en
not_active
IP Right Cessation
1970-05-13
FR
FR7017382A
patent/FR2051523B1/fr
not_active
Expired
1970-05-13
GB
GB23088/70A
patent/GB1268608A/en
not_active
Expired
1970-05-13
AT
AT04633/71A
patent/AT297719B/en
not_active
IP Right Cessation
1970-05-13
BE
BE750367D
patent/BE750367A/en
not_active
IP Right Cessation
1970-05-13
AT
AT463271A
patent/AT299961B/en
not_active
IP Right Cessation
1970-05-13
CH
CH756371A
patent/CH522663A/en
not_active
IP Right Cessation
1970-05-13
GB
GB23086/70A
patent/GB1268607A/en
not_active
Expired
Also Published As
Publication number
Publication date
CH522663A
(en)
1972-05-15
BE750367A
(en)
1970-10-16
SE380016B
(en)
1975-10-27
DE2023453C3
(en)
1975-04-10
US3660425A
(en)
1972-05-02
AT297719B
(en)
1972-03-15
NL148320B
(en)
1976-01-15
GB1268608A
(en)
1972-03-29
CH522664A
(en)
1972-05-15
AT298500B
(en)
1972-05-10
DE2023453A1
(en)
1970-11-19
NL7006933A
(en)
1970-11-17
US3558605A
(en)
1971-01-26
CH522665A
(en)
1972-05-15
CH510040A
(en)
1971-07-15
AT297709B
(en)
1972-04-10
FR2051523B1
(en)
1974-04-12
AT299961B
(en)
1972-07-10
DE2023453B2
(en)
1974-09-05
FR2051523A1
(en)
1971-04-09
Similar Documents
Publication
Publication Date
Title
US4243585A
(en)
1981-01-06
Bendodiazocine derivatives and process of making the same
GB1268607A
(en)
1972-03-29
NEW PYRAZOLO[3,4-e][1,4]DIAZEPIN-7(1H)-ONE COMPOUNDS AND METHODS FOR THEIR PRODUCTION
GB1351430A
(en)
1974-05-01
Substituted 1,2,4-triazole derivatives
GB1164503A
(en)
1969-09-17
Azaspiroalkanediones, process for preparing the same and Pharmaceutical Compositions comprising the same
ATE18910T1
(en)
1986-04-15
SUCCINIMIDE DERIVATIVES AND PROCESSES FOR THEIR MANUFACTURE.
PT99821A
(en)
1992-12-31
Process for the preparation of novel benzoyl benzene and pharmaceutical compositions containing the same
IE36797B1
(en)
1977-03-02
Derivatives of benzodiazepines
GB1327312A
(en)
1973-08-22
Hererocyclic compounds
HUT47580A
(en)
1989-03-28
Process for production of tricycle oxindole derivatives decreasing inflammation
GB1319026A
(en)
1973-05-31
Imidazole derivatives
GB1367598A
(en)
1974-09-18
Derivatives of delta 1-pyrroline their method of preparation and their applications
GB1256750A
(en)
1971-12-15
GB1432816A
(en)
1976-04-22
Pharmaceutical antimycotic compositions medicaments and method
US3953467A
(en)
1976-04-27
Pyrazole derivatives and process for preparing the same
GB1507709A
(en)
1978-04-19
Benz(de)isoquinoline derivatives
ES347749A1
(en)
1969-03-01
Certain 2-pyridyl-substituted indole derivatives
GB1336744A
(en)
1973-11-07
Substituted 2-amino-5-phenyl-3h-1,4-benzodazepine derivatives
ES8105266A1
(en)
1981-05-16
Diphenylalkanoether and diphenylalkanone oximeether derivatives, a process for their production, pharmaceutical compositions and their use.
GB1206088A
(en)
1970-09-23
New pyrazolodiazepinone compounds and methods for their production
GB1468129A
(en)
1977-03-23
Triazoles and imidazoles
IE33270B1
(en)
1974-05-01
5,10-dihydro-11h-dibenzo(b,e) (1,4) diazepine – 11 – ones
ES8305336A1
(en)
1983-04-01
4-Aryloxy-1,2,3,4-tetrahydroisoquinolines, and intermediates, a process for preparing the same, a pharmaceutical composition containing the same and their use as medicaments.
GB1323325A
(en)
1973-07-11
Indolo 1,2-d 1,4 benzodiazepin-6-ones
US3415840A
(en)
1968-12-10
Pyrazole-1-ethanol derivatives
ES407816A1
(en)
1976-02-16
Benzodiazepine derivatives
None