GB1078251A - Benzimidazolone derivatives - Google Patents
Benzimidazolone derivativesInfo
- Publication number
- GB1078251A GB1078251A GB3179/65D GB317965D GB1078251A GB 1078251 A GB1078251 A GB 1078251A GB 3179/65 D GB3179/65 D GB 3179/65D GB 317965 D GB317965 D GB 317965D GB 1078251 A GB1078251 A GB 1078251A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- compounds
- formula
- general formula
- alkylene
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Detergent Compositions (AREA)
Abstract
Compounds of the formula <FORM:1078251/C2/1> wherein R represents a straight or branched alkylene radical with from 2 to 4 carbon atoms; R1 represents a hydrogen atom or taken together with R2, an alkylene radical with from 2 to 4 carbon atoms; R2 represents, in addition, an alkyl radical with 1 to 3 carbon atoms or together with R3 an alkylene radical with 4 to 6 carbon atoms; R3 represents, in addition, a hydrogen atom or an alkyl radical with 1 to 3 carbon atoms; R4 which is in the 5- or 6-position, represents a hydrogen atom, a halogen atom or an alkyl radical containing from 1 to 3 carbon atoms; and R5 represents a hydrogen atom, a halogen atom or an alkyl radical containing 1 to 3 carbon atoms and pharmaceutically acceptable acid addition salts thereof and the preparation thereof: (a) by reacting a compound of the formula <FORM:1078251/C2/2> wherein R4 and R5 have the above significance with a reactive ester derived from an alcohol of the formula <FORM:1078251/C2/3> wherein R, R1, R2 and R3 have the above meaning, in an inert solvent after prior or with simultaneous exposure to a condensing agent such as an alkali metal or compounds thereof, e.g. the amide or alkoxide; (b) by condensing a compound of the formula <FORM:1078251/C2/4> wherein R, R1, R2, R3, R4 and R5 have the above significance, with a reactive derivative of carbonic acid, e.g. urea; (c) when R1 in the first general formula above is hydrogen, either by treating reactive esters derived from alcohols of the formula <FORM:1078251/C2/5> wherein R, R4 and R5 have the above meaning with a suitably substituted amine, or by alkylating primary amines of the formula <FORM:1078251/C2/6> wherein R, R4 and R5 are as above; and, finally, (d) when R4 and/or R5 in the first general formula above denote halogen, by diazotizing the corresponding compounds, in which R4 and/or R5 are amino groups and subsequently converting the resulting diazonium compounds to the desired halogen substituted products, e.g. by the Sandmeyer reaction. Pharmaceutical compositions suitable for enteral or parenteral administration, which are useful as anti-depressants or anti-convulsants, contain as the active principle one or more compounds of the first general formula above or pharmaceutically acceptable acid addition salts thereof in an inert carrier. Substituted benzimidazolones corresponding to the second general formula above are obtained by condensing compounds of the formula <FORM:1078251/C2/7> wherein R4 and R5 have the above significance, with a reactive derivative of carbonic acid, e.g. phosgene. Esters derived from alcohols of the fifth general formula above are obtained by treating compounds corresponding to the second general formula above with a mixed di-ester of an alkylene glycol, an alkylene oxide or an alkylene halhydrin or the tetrahydropyranyl ether thereof. 1 - Phenyl - 3 - (b - dimethylaminoethyl)-, 1 - phenyl - 3 - (g - dimethylaminopropyl)-, 1-phenyl - 3 - (11 - methyl - piperidyl - 31 - methyl)- 6 - chloro -, 1 - phenyl - 3 - (g - dimethylaminopropyl) - 6 - chloro - and 1 - p - chlorophenyl - 3 - (g - pyrrolidin - 11 - yl - propyl) - benzimidazolones are prepared among others using the above methods.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH133364A CH437315A (en) | 1964-02-05 | 1964-02-05 | Process for the preparation of benzimidazolone derivatives |
CH501764 | 1964-04-17 | ||
CH1000264 | 1964-07-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1078251A true GB1078251A (en) | 1967-08-09 |
Family
ID=27172901
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3179/65D Expired GB1078251A (en) | 1964-02-05 | 1965-01-25 | Benzimidazolone derivatives |
Country Status (14)
Country | Link |
---|---|
US (1) | US3338916A (en) |
BE (1) | BE659364A (en) |
BR (1) | BR6566831D0 (en) |
CH (4) | CH438335A (en) |
DE (1) | DE1620702A1 (en) |
DK (4) | DK109805C (en) |
ES (1) | ES308785A1 (en) |
FI (1) | FI44407B (en) |
FR (1) | FR3952M (en) |
GB (1) | GB1078251A (en) |
IL (1) | IL22841A (en) |
NL (1) | NL6501434A (en) |
NO (1) | NO116324B (en) |
SE (4) | SE343580B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3996238A (en) * | 1972-02-08 | 1976-12-07 | Ciba-Geigy Corporation | 4- or 5-Nitroimidazoles and processes for their manufacture |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3989707A (en) * | 1974-06-21 | 1976-11-02 | Janssen Pharmaceutica N.V. | Benzimidazolinone derivatives |
DE2609645A1 (en) * | 1976-03-09 | 1977-09-15 | Boehringer Sohn Ingelheim | AMINOALKYLHETEROCYCLES |
US4335132A (en) * | 1980-12-29 | 1982-06-15 | Sterling Drug, Inc. | 5-(Py-Y)-1H-benzimidazol-2-ols and 5-(Py-Y-)-1H-benzimidazole-2-thiols |
US5200422A (en) * | 1990-09-24 | 1993-04-06 | Neurosearch A/S | Benzimidazole derivatives, their preparation and use |
GB9613423D0 (en) * | 1996-06-26 | 1996-08-28 | Lilly Industries Ltd | Pharmaceutical compounds |
US7526342B2 (en) | 1999-08-10 | 2009-04-28 | Maquet Cardiovascular Llc | Apparatus for endoscopic cardiac mapping and lead placement |
US7264587B2 (en) | 1999-08-10 | 2007-09-04 | Origin Medsystems, Inc. | Endoscopic subxiphoid surgical procedures |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT290523B (en) * | 1962-01-05 | 1971-06-11 | Merck & Co Inc | Process for the production of new α- (3-indolyl) -carboxylic acids |
-
0
- BE BE659364D patent/BE659364A/xx unknown
-
1964
- 1964-02-05 CH CH661867A patent/CH438335A/en unknown
- 1964-02-05 CH CH661767A patent/CH437317A/en unknown
- 1964-02-05 CH CH661967A patent/CH437318A/en unknown
- 1964-02-05 CH CH133364A patent/CH437315A/en unknown
-
1965
- 1965-01-22 DE DE19651620702 patent/DE1620702A1/en active Pending
- 1965-01-25 GB GB3179/65D patent/GB1078251A/en not_active Expired
- 1965-01-25 IL IL22841A patent/IL22841A/en unknown
- 1965-01-29 FR FR3628A patent/FR3952M/fr not_active Expired
- 1965-01-29 US US429160A patent/US3338916A/en not_active Expired - Lifetime
- 1965-01-30 ES ES0308785A patent/ES308785A1/en not_active Expired
- 1965-02-02 BR BR166831/65A patent/BR6566831D0/en unknown
- 1965-02-04 NL NL6501434A patent/NL6501434A/xx unknown
- 1965-02-04 FI FI0274/65A patent/FI44407B/fi active
- 1965-02-04 NO NO156634A patent/NO116324B/no unknown
- 1965-02-05 DK DK52466AA patent/DK109805C/en active
- 1965-02-05 DK DK60465AA patent/DK109804C/en active
- 1965-02-05 DK DK52566AA patent/DK109988C/en active
- 1965-02-05 SE SE7124/69A patent/SE343580B/xx unknown
- 1965-02-05 SE SE1479/65A patent/SE322223B/xx unknown
- 1965-02-05 DK DK52666AA patent/DK109869C/en active
-
1969
- 1969-05-20 SE SE7125/69A patent/SE343581B/xx unknown
- 1969-05-20 SE SE7123/69A patent/SE343579B/xx unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3996238A (en) * | 1972-02-08 | 1976-12-07 | Ciba-Geigy Corporation | 4- or 5-Nitroimidazoles and processes for their manufacture |
Also Published As
Publication number | Publication date |
---|---|
NL6501434A (en) | 1965-08-06 |
DE1620702A1 (en) | 1970-03-12 |
SE343579B (en) | 1972-03-13 |
CH438335A (en) | 1967-06-30 |
SE322223B (en) | 1970-04-06 |
ES308785A1 (en) | 1965-12-16 |
CH437317A (en) | 1967-06-15 |
BE659364A (en) | |
DK109805C (en) | 1968-07-08 |
CH437318A (en) | 1967-06-15 |
SE343581B (en) | 1972-03-13 |
DK109988C (en) | 1968-08-19 |
CH437315A (en) | 1967-06-15 |
DK109869C (en) | 1968-07-22 |
FR3952M (en) | 1966-02-21 |
NO116324B (en) | 1969-03-10 |
FI44407B (en) | 1971-08-02 |
US3338916A (en) | 1967-08-29 |
IL22841A (en) | 1968-05-30 |
BR6566831D0 (en) | 1973-08-14 |
DK109804C (en) | 1968-07-08 |
SE343580B (en) | 1972-03-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
YU42116B (en) | Process for obtaining ethanol amine derivatives | |
ES8107185A1 (en) | Piperidine derivatives, their preparation and pharmaceutical compositions containing them. | |
GB1078251A (en) | Benzimidazolone derivatives | |
ES345981A1 (en) | Pyridines and poultry feedstuffs and additives thereof containing pyridines | |
ES346521A1 (en) | N-(sulfonylcarbamoyl)-bornano-(3',2':4,5)-oxazolidin-3-ones | |
EP0040573A3 (en) | 2-substituted-4-hydroxy-3-quinolinecarboxylic acids, their preparation, their use as medicaments, compositions containing them and intermediates | |
GB972888A (en) | New 2-amino-(mono- or di-substituted)-ethyl-guanidines | |
GB1186863A (en) | Salts of 6-Phosphogluconic Acid and Pharmaceutical Compositions containing 6-Phosphogluconic Acid or Salts thereof | |
SE7909367L (en) | PREPARED TO PIPERIDYL-INDOL DERIVATIVES, NEW PREPARED ASSOCIATION AND ITS SALTS AND USE THEREOF AS MEDICINAL AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS | |
GB984119A (en) | Substituted piperidines and methods for their preparation | |
GB997637A (en) | Substituted 2-cyclopropylmethyl-6,7-benzmorphans | |
ES384946A1 (en) | Novel adamantylurea derivatives and a process for the preparation thereof | |
JPS57146786A (en) | Optically active borane compound and preparation of optically active compound using the same | |
GB1112909A (en) | Ergoline derivatives | |
GB1093121A (en) | Etherified ªÐ-hydroxyanilines | |
GB959993A (en) | Camphor derivatives | |
GB1022935A (en) | Derivatives of dihydro-d-lysergic acid | |
ES8305304A1 (en) | Therapeutically active derivatives of phenylethanol amines. | |
GB1172788A (en) | N-(Azabicycloalkylisopropyl)-Aminopyridine Derivatives | |
ES278796A1 (en) | New uracil derivatives and process for their production | |
GB771151A (en) | Method for the preparation of aminoacyl-anilides | |
GB999393A (en) | New ethers of the yohimbane series and process for their manufacture | |
GB1067694A (en) | A process for the preparation of 2-alkyl-4-alkylamino-6-alkoxy-s-triazines | |
GB994008A (en) | New amino steroids and processes for their preparation | |
GB923311A (en) | Pharmaceutical anti-mycobacterial compositions comprising ethylenediamine derivatives |