IE36678B1 - A process for substitution of 1-derivatives of 1/-hydroxybenzimidazoles and 1-hydroxyimidazo (4,5-b) pyridines - Google Patents
A process for substitution of 1-derivatives of 1/-hydroxybenzimidazoles and 1-hydroxyimidazo (4,5-b) pyridinesInfo
- Publication number
- IE36678B1 IE36678B1 IE1643/71A IE164371A IE36678B1 IE 36678 B1 IE36678 B1 IE 36678B1 IE 1643/71 A IE1643/71 A IE 1643/71A IE 164371 A IE164371 A IE 164371A IE 36678 B1 IE36678 B1 IE 36678B1
- Authority
- IE
- Ireland
- Prior art keywords
- imidazo
- trifluoromethyl
- pyridine
- nitro
- chloro
- Prior art date
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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1374800 Benzimidazoles and imidazo-[4,5-b] pyridines ELI LILLY & CO 23 Dec 1971 [28 Dec 1970] 60113/71 Heading C2C A process for preparing benzimidazole or imidazo-(4,5-b) derivatives of the general formulae wherein Y is Cl or F; R<SP>1</SP> is H, Cl, F, C 1 -C 6 perfluoroalkyl or a radical of general formula -(CHZ) n -CH 2 Z, in which Z is H or halogen and n is 0 or 1; each R<SP>3</SP> is halogen; each R<SP>4</SP> is nitro, -CF 3 , -CF 2 Cl or -CF 2 H; R<SP>5</SP> is cyano or C 1 -C 4 alkylsulphonyl; m is 0 or an integer 1-3, n is 0, 1 or 2, r is 0 or 1 and the sum of m, n and r is 0 or an integer of 1-3 and each R<SP>6</SP> is halogen, nitro, -CF 3 , -CF 2 Cl, -CF 2 H or C 1 -C 4 alkylsulphonyl providing not more than one R<SP>6</SP> is nitro, -CF 3 , -CF 2 Cl, -CF 2 H or alkylsulphonyl, involves treating an ester of a 1 - hydroxybenzimidazole or -imidazo - (4,5 - b) pyridine of general formula with a chloride or fluoride nucleophilic reagent, wherein -OR<SP>2</SP> is a group formed by reaction of the 1-hydroxy compound with a chloride, fluoride, oxychloride, oxyfluoride or oxide of P, As, Sb or S or R<SP>2</SP> is (1) C 1 -C 6 alkanoyl; (2) C 3 -C 16 alkenoyl; (3) carbamoyl of general formula -C(X)-N(R 7 ) 2 where X is O or S; one R<SP>7</SP> is phenyl, C 1 -C 4 alkyl or C 2 -C 4 alkenyl and the other R<SP>7</SP> is H, C 1 -C 4 alkyl or C 2 -C 4 alkenyl, provided that the two R<SP>7</SP> groups together do not contain more than 6C atoms, or both R<SP>7</SP> taken together represent a C 2 -C 6 straight alkylene chain; (4) a radical of general formula in which R<SP>8</SP> is methylene, ethylene or vinylene and q is 0 or 1; (5) -SO 2 R<SP>9</SP> in which R<SP>9</SP> is C 1 -C 4 alkyl, C 5 -C 6 cycloalkyl, phenyl or benzyl or (6) -C(O)-X-C 1 -C 4 alkyl or where X is O or S. The Cl or F ion may be provided by the compound used to derive the unstable halides or oxyhalides, e.g. thionyl chloride, oxalyl halide or phosgene. Amongst the examples 1-hydroxy-4,6-dinitro-2-(trifluoromethyl - benzimidazole was treated with thionyl chloride to yield 7-chloro-4,6-dinitro-2- (trifluoromethyl)benzimidazole and 1 - (methylcarbamoyloxy) - 6 - chloro - 2 - (trifluoromethyl)- 1H - imidazo - (4,5 - b)pyridine was treated with HCl to give 5,6 - dichloro - 2 - (trifluoromethyl) - 1H - imidazo - (4,5 - b)pyridine. 1 - Hydroxy - 6'- chloro - 2 - (trifluoromethyl)- 1H - imidazo - (4,5 - b) - pyridine was obtained by reductive cyclization of 5-chloro-3-nitro-2- (trifluoroacetamido)pyridine. Reference has been directed by the Comptroller to Specifications 1,087,561 and 1,307,489.
[GB1374800A]
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE300/75A IE36680B1 (en) | 1970-12-28 | 1971-12-23 | A process for reduction of 1-derivatives of 1-hydroxy benzimidazoles and 1-hydroxyimidazo (4,5-b) pyridines |
| IE299/75A IE36679B1 (en) | 1970-12-28 | 1971-12-23 | A process for substitution of 1-derivatives of 1-hydroxy benzimidazoles and 1hydroxyimidazo (4,5-b) pyridines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10226670A | 1970-12-28 | 1970-12-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE36678L IE36678L (en) | 1972-06-28 |
| IE36678B1 true IE36678B1 (en) | 1977-02-02 |
Family
ID=22288990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1643/71A IE36678B1 (en) | 1970-12-28 | 1971-12-23 | A process for substitution of 1-derivatives of 1/-hydroxybenzimidazoles and 1-hydroxyimidazo (4,5-b) pyridines |
Country Status (19)
| Country | Link |
|---|---|
| AR (2) | AR201728A1 (en) |
| AT (2) | AT318608B (en) |
| AU (1) | AU465099B2 (en) |
| BE (1) | BE777250A (en) |
| CA (1) | CA969547A (en) |
| CH (3) | CH554873A (en) |
| DE (2) | DE2165021A1 (en) |
| DK (1) | DK139385B (en) |
| ES (1) | ES398379A1 (en) |
| FR (1) | FR2121020A5 (en) |
| GB (3) | GB1374800A (en) |
| IE (1) | IE36678B1 (en) |
| IL (1) | IL38452A (en) |
| IT (1) | IT945597B (en) |
| NL (1) | NL7118000A (en) |
| SE (1) | SE412064B (en) |
| SU (3) | SU535905A3 (en) |
| YU (2) | YU35001B (en) |
| ZA (1) | ZA718532B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4031107A (en) * | 1972-12-13 | 1977-06-21 | Eli Lilly And Company | Method for introducing amino groups into benzimidazole or imidazopyridine compounds |
| US4265901A (en) * | 1979-12-26 | 1981-05-05 | Eli Lilly And Company | 2-Oxybenzimidazoline compounds |
-
1971
- 1971-12-21 ZA ZA718532A patent/ZA718532B/en unknown
- 1971-12-22 IT IT54935/71A patent/IT945597B/en active
- 1971-12-22 SE SE7116475A patent/SE412064B/en unknown
- 1971-12-23 CA CA130,993A patent/CA969547A/en not_active Expired
- 1971-12-23 GB GB6011371A patent/GB1374800A/en not_active Expired
- 1971-12-23 GB GB3809473A patent/GB1375157A/en not_active Expired
- 1971-12-23 GB GB3830273A patent/GB1377469A/en not_active Expired
- 1971-12-23 IE IE1643/71A patent/IE36678B1/en unknown
- 1971-12-24 BE BE777250A patent/BE777250A/en unknown
- 1971-12-24 AU AU37333/71A patent/AU465099B2/en not_active Expired
- 1971-12-27 DK DK634871AA patent/DK139385B/en unknown
- 1971-12-27 IL IL38452A patent/IL38452A/en unknown
- 1971-12-27 AT AT163873A patent/AT318608B/en not_active IP Right Cessation
- 1971-12-27 AT AT1113071A patent/AT312598B/en not_active IP Right Cessation
- 1971-12-28 DE DE19712165021 patent/DE2165021A1/en not_active Ceased
- 1971-12-28 DE DE19712166996 patent/DE2166996A1/en not_active Ceased
- 1971-12-28 ES ES398379A patent/ES398379A1/en not_active Expired
- 1971-12-28 CH CH197073A patent/CH554873A/en not_active IP Right Cessation
- 1971-12-28 CH CH1905071A patent/CH558366A/en not_active IP Right Cessation
- 1971-12-28 NL NL7118000A patent/NL7118000A/xx not_active Application Discontinuation
- 1971-12-28 AR AR239854A patent/AR201728A1/en active
- 1971-12-28 CH CH138073A patent/CH556342A/en not_active IP Right Cessation
- 1971-12-28 YU YU3284/71A patent/YU35001B/en unknown
- 1971-12-28 FR FR7147107A patent/FR2121020A5/fr not_active Expired
-
1973
- 1973-10-18 SU SU1966487A patent/SU535905A3/en active
-
1974
- 1974-01-04 AR AR251821A patent/AR196969A1/en active
- 1974-05-15 SU SU2133311A patent/SU535908A3/en active
-
1975
- 1975-05-15 SU SU1732630A patent/SU541436A3/en active
-
1978
- 1978-12-11 YU YU2895/78A patent/YU35256B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU535905A3 (en) | 1976-11-15 |
| SU535908A3 (en) | 1976-11-15 |
| ZA718532B (en) | 1973-08-29 |
| NL7118000A (en) | 1972-06-30 |
| FR2121020A5 (en) | 1972-08-18 |
| YU35001B (en) | 1980-06-30 |
| AU3733371A (en) | 1973-06-28 |
| CH556342A (en) | 1974-11-29 |
| DK139385B (en) | 1979-02-12 |
| IL38452A (en) | 1975-04-25 |
| DE2165021A1 (en) | 1972-10-12 |
| IT945597B (en) | 1973-05-10 |
| DE2166996A1 (en) | 1977-05-18 |
| AT318608B (en) | 1974-11-11 |
| YU328471A (en) | 1979-12-31 |
| GB1374800A (en) | 1974-11-20 |
| GB1377469A (en) | 1974-12-18 |
| DK139385C (en) | 1979-07-30 |
| GB1375157A (en) | 1974-11-27 |
| YU35256B (en) | 1980-10-31 |
| ES398379A1 (en) | 1975-06-16 |
| YU289578A (en) | 1980-04-30 |
| CA969547A (en) | 1975-06-17 |
| CH554873A (en) | 1974-10-15 |
| AT312598B (en) | 1974-01-10 |
| IL38452A0 (en) | 1972-02-29 |
| AR196969A1 (en) | 1974-02-28 |
| AR201728A1 (en) | 1975-04-15 |
| CH558366A (en) | 1975-01-31 |
| BE777250A (en) | 1972-06-26 |
| IE36678L (en) | 1972-06-28 |
| SU541436A3 (en) | 1976-12-30 |
| AU465099B2 (en) | 1975-09-18 |
| SE412064B (en) | 1980-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU575740B2 (en) | Anti-dysrhythmia agent | |
| GB1322930A (en) | Benzimidazo 2,1-b quinazolin derivatives as immuno suppressants | |
| IE36678B1 (en) | A process for substitution of 1-derivatives of 1/-hydroxybenzimidazoles and 1-hydroxyimidazo (4,5-b) pyridines | |
| TR200003322T2 (en) | Water-soluble azoles used as broad-spectrum fungicide | |
| EP0274654A3 (en) | 1,2,3-triazin-4(3h)-one derivatives, process for their preparation and medicaments containing them | |
| FI833101A (en) | TERT OF SUBSTITUTES. -BUTANOL DERIVATIVES, FOERFARANDE FOER DERAS FRAMSTAELLNING OCH DESSA INNEHAOLLANDEANTIMYKOTISKA MEDEL | |
| Nakashima et al. | Physicochemical properties of amphoteric β-lactam antibiotics. IV. First-and second-order degradations of cefaclor and cefatrizine in aqueous solution and kinetic interpretation of the intestinal absorption and degradation of the concentrated antibiotics | |
| SE7600505L (en) | PROCEDURE FOR THE PREPARATION OF PHENYL ALKYLAMINES | |
| GB1526835A (en) | Ergoline derivatives | |
| ES527739A0 (en) | A PROCEDURE FOR PREPARING PIRIMIDINE DERIVATIVES | |
| ES469203A1 (en) | Novel benzo *c* quinolines | |
| DK165584D0 (en) | (1H-TETRAZOL-5-YL) TETRAZOLO (1,5-A) QUINOLINES AND RELATED COMPOUNDS | |
| PT1068200E (en) | ANTIFUNGIC 1,3-DIOXOLANE 2,4,4-TIR-SUBSTITUTED | |
| GB8718939D0 (en) | Chemical compounds | |
| DD233844A5 (en) | METHOD FOR PRODUCING MITOMYCIN ANALOGIC COMPOUNDS | |
| IE34252B1 (en) | Benzodiazepine derivatives | |
| IT8348872A0 (en) | PROCEDURE FOR THE DETERMINATION OF THE STATE OF VIRULENCE OR LATENCE OF THE HERPES VIRUS IN CELLULAR TISSUES | |
| PT77300B (en) | SUBSTITUTED BENZOXAZINE DERIVATIVES | |
| GB1359223A (en) | Benzodiazepine derivatives processes for producing them 'and compositions containing them | |
| JPS57131751A (en) | Azoguanyl polymerization initiator | |
| GB1314864A (en) | N-arylureas a process for their production and their use as herbicid | |
| YAMANA | Concentrated Antibiotics” | |
| GB1315243A (en) | Triaza heterocyclic compounds | |
| JPS53116388A (en) | Novel dihydroxyquinazoline derivatives and process for their preparation | |
| 中島恵美 et al. | Physicochemical properties of amphoteric. BETA.-lactam antibiotics. IV. First-and second-order degradations of cefaclor and cefatrizine in aqueous solution and kinetic interpretation of the intestinal absorption and degradation of the concentrated antibiotics. |