IL38643A - 5-phenyl(or pyridyl)-1h-3-hydroxy-1,5-benzodiazepine-2,4-dione derivatives,their preparation and pharmaceutical compositions containing them - Google Patents
5-phenyl(or pyridyl)-1h-3-hydroxy-1,5-benzodiazepine-2,4-dione derivatives,their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL38643A IL38643A IL38643A IL3864372A IL38643A IL 38643 A IL38643 A IL 38643A IL 38643 A IL38643 A IL 38643A IL 3864372 A IL3864372 A IL 3864372A IL 38643 A IL38643 A IL 38643A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- effected
- compound
- compounds
- reaction
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1374529 Benzodiazepines BOEHRINGER INGELHEIM GmbH 26 Jan 1972 [27 Jan 1971] 3719/72 Heading C2C Compounds of the general formula (R<SP>1</SP>=H, alkyl, alkenyl, hydroxyalkyl, cycloalkylalkyl; R 2 =unsubstituted or substituted Ph or Py; R 3 = halogen, CF 3 , NO 2 ) are prepared by (a) reducing a compound of the formula (b) mild oxidation of a compound of the formula (R 4 , R 5 =H, alkyl), or (c) reacting a compound of the formula (R 1 not H) with water, optionally followed in the case of (a) and (b) by introduction of a 1- substituent. The above compounds are tranquilizers and anti-convulsants, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.
[GB1374529A]
Claims (1)
1. 38643/2 1. Compounds of the general formula: wherein represents a hydrogen atom; a straight or branched alkyl group with 1 to 4 carbon atoms optionally substituted in the CJ position by a hydroxy group; or an allyl; represents a phenyl group which may if desired be substituted by a halogen atom or by a trifluoromethyl or nitro group; or a pyridyl group; and represents a fluorine, chlorine or bromine atom or a trifluoromethyl or nitro group. 38643/2 2. 1 Compounds as claimed in claim j 1 wherein represents a hydrogen atom or a me hyl or ethyl group; 1*2 represents a phenyl group which may if desired be substituted in the o-position by a tri- fluoromethyl group; or a pyridyl group and represents a chlorine or bromine atom or a trifluoromethyl group. 3, ; 3-Hydroxy-l-methyl-5-phenyl-7-chloro-lH-l , 5- benzodiazepine-2 ,4-(3H , 5H)rdione. 4. ' ' 3-Hydroxy-5-(o-trifluoromethylphenyl)-7-chloro- lH-1 ,5-benzodiazepine-2 ,4-(3H, 5H)-dione. 5. 7-Chloro-3-hydroxy-l-methyl-5-(o-trifluoromethyl- phenyl) -lH-1 , 5-benzodiazepine-2 ,4-(3H ,5H)-dione. 6. 7-Bromo-3-hydroxy-l-methyl-5-(a-pyridyl)-lH-l , 5- benzodiazepine-2 ,4-(3H , 5H)-dione. 7. Compounds as claimed in claim 1, other than as — ■' ' ¾ claimed in any of claims 3 to 6 , as herein specifically disclosed. 8. ' A process for the preparation of compounds as claimed in claim 1 which comprises reducing a compound of the formula 38643/2 (wherein R. , R. and R- are as defined in claim 1) or a 1 ' 2 3 I 1 hydrate thereof whereby a compound of formula I (as defined in claim 1) is obtained. I 9." A process as claimed in .claim 8 wherein the reduction is effected by the use of zinc/glacial acetic acid or tin/hydrochloric acid. 20. A process as claimed in claim 8 or claims 9 wherein the reduction is effected at an elevated temperature. .11· A process as claimed .in claim 8 wherein the reduction is effected catalytically or by the use of' an alkali metal borohydride. ^12.; A process as claimed in claim, 11 wherein the alkali metal borohyU > *i >Ie comprises sodium borohydride. 13. A process for the preparation of compounds as ···'■':..; claimed in claim 1 which comprises the mild oxidation of a compound of the formula: 38643/2 « "L (wherein R^, and are as defined in claim 1 and R^ and R,. which may be the same or different each : represent a hydrogen atom or a straight or branched alkyl group). ' 14. ! A process as claimed in claim 13 wherein a' compound of formula III is used in which ^ and/or j I R_ represents a straight or branched alkyl group with | 1 to 4 carbon atoms. 15· : A process as claimed in claim! 13 or claimj 14J wherein the mild oxidation is !effected by the use„of ! potassium permanganate or chromic acid. 16.1 A process as claimed in any of claimsj 13; to 14 i wherein the mild oxidation is effected at a low temperature. 17.j A process as claimed in any of claimsj 13- 1 toj 16 ' wherein the mild oxidation is effected in a weakly acidic medium. , iQe I' A process for the preparation of compounds as claimed in claim 1 (wherein R^ is other than hydrogen) 38643/3 which comprises reacting a compound of the formula: (wherein R^, and R^ are as defined in claim 1 with the proviso that R^ is other than hydrogen) to convert the compound of formula IV into a compound of formula ! I. I I 19, ί A process as claimed in claimj 18 ' wherein the reaction is effected by the use of water, 20» J A process as claimed in claim le or claim! 19 wherein the reaction is effected in the presence of an inert solvent, 21, Ί A process as claimed in any of claims, 18 to^' 20 wherein the reaction is effected in the presence of copper powder or a copper salt. 22. A process as claimed in claimj 21 wherein the copper salt is copper sulphate. 23.i A process for the preparation of compounds as claimed in claim 1 (wherein R^ is other than hydrogen) which comprises reacting a compound of the formula: 38643/5- H an appropriate alkylating or allylating agent whereby a compound of formula I as defined in claim 1 (wherein is other than hydrogen) is obtained. 24. A process as claimed in claim 23 wherein the alkylating, or allylating agent comprises an alkyl or allyl halide or a dialkyl or diallyl sulfate. 25. A modification of a process as claimed in claim 23 or claim 24 wherein an alkali metal salt of the compound of formula la (as defined in claim 23) is i . used in place of the compound of formula la (as defined in claim 23 ) . 26. A process for the preparation of compounds as claimed in claim l(wherein represents a hydroxy- alkyl group) which comprises reacting a compound of the formula 2 (wherein and are as defined in claim 1) with an alkylene oxide). ■ ; i , 27.1 A process as claimed in claim 26 wherein the I . reaction is effected in the presence of a strong base. Ί 1 _ ·_:_. : ' 28. A process as claimed in claimi26 or claimi27 Ί ; ' · '· ;■ wherein the reaction is effected in the presence of i i ■ : i an appropriate solvent or mixture of solvents. j 29. A process as claimed in any of claims 26 to 28 ,! wherein the solvent comprises an alcohol, tetrahydrofuran, i ■ ■· ,. or dimethylformamide. j j " 'Ί ,.. .. , .. . j ;30.j A process as claimed in any of claims|26 | o \ 291 | wherein the reaction is effected in the presence of water. 131 J A process for the preparation of compounds as claimed in cl alkyl group) of formula: 38643/3 (wherein anc* ^-3 are as def ned in claim 1) with haloalcohol with 1 to 4 carbon atoms. 32 j A process as claimed in claim, 31 wherein the reaction is effected in the presence of a weak inorganic or organic base. 33 . A process as claimed in claim 31 or claim 32 wherein the reaction is effected at an elevated temperature. 34. A process as claimed in any of claims 31 to 33 wherein the reaction is effected in the presence of an organic solvent. 35 . A process as claimed in claim 34 wherein the solvent comprises a lower or higher alcohol. 36 . A process as claimed in a'ny of claims 8 to 35 substantially as herein described. 37. A process for the preparation of compounds as claimed in claim 1, substantially as herein described in any of Examples 1 to ;26. 38. Compounds as claimed in claim 1 when prepared by a process as claimed in any of claims 8 to : 37. 39. Pharmaceutical compositions comprising as active ingredient at least one compound of formula I as claimed in any of claims 1 to 6 and 35 in association with a pharmaceutical carrier or excipient.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19712103745 DE2103745A1 (en) | 1971-01-27 | 1971-01-27 | New 5-AryJ- (or Heteroaryl) -3-hydroxylH-1,5-benzodiazepine-2,4- (3H, 5H) -diones and processes for their preparation |
Publications (2)
Publication Number | Publication Date |
---|---|
IL38643A0 IL38643A0 (en) | 1972-03-28 |
IL38643A true IL38643A (en) | 1976-01-30 |
Family
ID=5797047
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL38643A IL38643A (en) | 1971-01-27 | 1972-01-26 | 5-phenyl(or pyridyl)-1h-3-hydroxy-1,5-benzodiazepine-2,4-dione derivatives,their preparation and pharmaceutical compositions containing them |
Country Status (19)
Country | Link |
---|---|
AT (3) | AT315849B (en) |
AU (1) | AU464682B2 (en) |
BE (1) | BE778542A (en) |
BG (3) | BG19174A3 (en) |
CA (1) | CA967957A (en) |
DD (1) | DD99376A5 (en) |
DE (1) | DE2103745A1 (en) |
DK (1) | DK130411B (en) |
ES (3) | ES399169A1 (en) |
FR (1) | FR2123474B1 (en) |
GB (1) | GB1374529A (en) |
HU (1) | HU164575B (en) |
IE (1) | IE36035B1 (en) |
IL (1) | IL38643A (en) |
NL (1) | NL7201048A (en) |
PL (3) | PL91875B1 (en) |
RO (3) | RO60492A (en) |
SU (3) | SU493971A3 (en) |
ZA (1) | ZA72538B (en) |
-
1971
- 1971-01-27 DE DE19712103745 patent/DE2103745A1/en active Pending
-
1972
- 1972-01-14 RO RO71244A patent/RO60492A/ro unknown
- 1972-01-14 RO RO69392A patent/RO61669A/ro unknown
- 1972-01-14 RO RO71243A patent/RO60491A/ro unknown
- 1972-01-24 SU SU1926941A patent/SU493971A3/en active
- 1972-01-24 SU SU1740811A patent/SU465791A3/en active
- 1972-01-25 BG BG19569A patent/BG19174A3/xx unknown
- 1972-01-25 HU HUBO1347A patent/HU164575B/hu unknown
- 1972-01-25 ES ES399169A patent/ES399169A1/en not_active Expired
- 1972-01-25 BG BG21122A patent/BG19176A3/xx unknown
- 1972-01-25 BG BG21123A patent/BG21031A3/xx unknown
- 1972-01-26 ZA ZA720538A patent/ZA72538B/en unknown
- 1972-01-26 IL IL38643A patent/IL38643A/en unknown
- 1972-01-26 GB GB371972A patent/GB1374529A/en not_active Expired
- 1972-01-26 NL NL7201048A patent/NL7201048A/xx unknown
- 1972-01-26 PL PL1972175546A patent/PL91875B1/pl unknown
- 1972-01-26 PL PL1972175545A patent/PL84243B1/pl unknown
- 1972-01-26 DK DK34672AA patent/DK130411B/en unknown
- 1972-01-26 AT AT60972A patent/AT315849B/en not_active IP Right Cessation
- 1972-01-26 AU AU38362/72A patent/AU464682B2/en not_active Expired
- 1972-01-26 AT AT611173A patent/AT315864B/en not_active IP Right Cessation
- 1972-01-26 AT AT611273A patent/AT316566B/en not_active IP Right Cessation
- 1972-01-26 PL PL1972153120A patent/PL84620B1/pl unknown
- 1972-01-26 DD DD160513A patent/DD99376A5/xx unknown
- 1972-01-26 BE BE778542A patent/BE778542A/en unknown
- 1972-01-27 IE IE111/72A patent/IE36035B1/en unknown
- 1972-01-27 FR FR7202739A patent/FR2123474B1/fr not_active Expired
- 1972-01-27 CA CA133,282A patent/CA967957A/en not_active Expired
-
1973
- 1973-01-24 SU SU1926940A patent/SU460627A3/en active
-
1974
- 1974-04-08 ES ES425108A patent/ES425108A1/en not_active Expired
- 1974-04-08 ES ES425107A patent/ES425107A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
BG21031A3 (en) | 1976-01-20 |
DE2103745A1 (en) | 1972-08-10 |
CA967957A (en) | 1975-05-20 |
DK130411C (en) | 1975-07-21 |
RO60491A (en) | 1976-06-15 |
FR2123474A1 (en) | 1972-09-08 |
IE36035L (en) | 1972-07-27 |
PL91875B1 (en) | 1977-03-31 |
SU493971A3 (en) | 1975-11-28 |
BE778542A (en) | 1972-07-26 |
SU465791A3 (en) | 1975-03-30 |
PL84620B1 (en) | 1976-04-30 |
ES425107A1 (en) | 1976-07-01 |
RO60492A (en) | 1976-06-15 |
AT315864B (en) | 1974-06-10 |
DK130411B (en) | 1975-02-17 |
ES399169A1 (en) | 1975-06-01 |
HU164575B (en) | 1974-03-28 |
ES425108A1 (en) | 1976-07-01 |
RO61669A (en) | 1976-11-15 |
AU464682B2 (en) | 1975-08-20 |
GB1374529A (en) | 1974-11-20 |
BG19174A3 (en) | 1975-04-30 |
SU460627A3 (en) | 1975-02-15 |
AU3836272A (en) | 1973-08-02 |
IE36035B1 (en) | 1976-08-04 |
AT316566B (en) | 1974-07-25 |
BG19176A3 (en) | 1975-04-30 |
PL84243B1 (en) | 1976-03-31 |
NL7201048A (en) | 1972-07-31 |
DD99376A5 (en) | 1973-08-05 |
FR2123474B1 (en) | 1975-10-10 |
IL38643A0 (en) | 1972-03-28 |
AT315849B (en) | 1974-06-10 |
ZA72538B (en) | 1973-09-26 |
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