GB1198942A - Benzimidazole Derivatives - Google Patents
Benzimidazole DerivativesInfo
- Publication number
- GB1198942A GB1198942A GB46573/69A GB4657369A GB1198942A GB 1198942 A GB1198942 A GB 1198942A GB 46573/69 A GB46573/69 A GB 46573/69A GB 4657369 A GB4657369 A GB 4657369A GB 1198942 A GB1198942 A GB 1198942A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- compound
- carbamoyl
- feb
- alkoxy
- 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
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title abstract 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- WFRXSXUDWCVSPI-UHFFFAOYSA-N 3h-benzimidazol-5-amine Chemical class NC1=CC=C2NC=NC2=C1 WFRXSXUDWCVSPI-UHFFFAOYSA-N 0.000 abstract 1
- 208000006968 Helminthiasis Diseases 0.000 abstract 1
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001556 benzimidazoles Chemical class 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH OR ROCK DRILLING; MINING
- E21D—SHAFTS; TUNNELS; GALLERIES; LARGE UNDERGROUND CHAMBERS
- E21D11/00—Lining tunnels, galleries or other underground cavities, e.g. large underground chambers; Linings therefor; Making such linings in situ, e.g. by assembling
- E21D11/14—Lining predominantly with metal
- E21D11/28—Longitudinal struts, i.e. longitudinal connections between adjoining arches
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Mining & Mineral Resources (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Geology (AREA)
- Structural Engineering (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Geochemistry & Mineralogy (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Civil Engineering (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Architecture (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
1,198,942. Benzimidazole derivatives. MERCK & CO. Inc. 1 Feb., 1968 [3 Feb., 1967; 9 Jan., 1968], No. 46573/69. Divided out of 1,198,941. Heading C2C. Novel compounds (I) in which R is alkyl or aryl; R 1 is a five-membered monocyclic heteroaromatic ring containing 1-3 O, S or N atoms; R 2 is H, OH, C 1-8 alkoxy, C 1-8 alkyl, aralkyl, acyl, acyloxy, carboxy- C 1-8 -alkoxy, carbamoyl, N-alkyl-carbamoyl, or alkoxycarbonyl; and R 3 is H or C 1-8 alkyl are prepared by (a) reacting the appropriate 5- amino benzimidazole derivative with RSO 2 Y where Y is halo or (b) reacting a compound produced by method (a) with a C 1-8 alkyl halide to produce a compound (I) in which R 3 is C 1-8 alkyl. The corresponding 5-NHR 3 compounds are prepared from (I) in which R 3 is C 1-8 alkyl by treatment with a concentrated mineral acid. Pharmaceutical compositions for oral or parenteral application in the treatment of helminthiasis comprise a compound (I) in conjunction with a suitable diluent or carrier.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61374667A | 1967-02-03 | 1967-02-03 | |
| US69649668A | 1968-01-09 | 1968-01-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1198942A true GB1198942A (en) | 1970-07-15 |
Family
ID=27087090
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB46573/69A Expired GB1198942A (en) | 1967-02-03 | 1968-02-01 | Benzimidazole Derivatives |
| GB5259/68A Expired GB1198941A (en) | 1967-02-03 | 1968-02-01 | Benzimidazole Derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5259/68A Expired GB1198941A (en) | 1967-02-03 | 1968-02-01 | Benzimidazole Derivatives |
Country Status (19)
| Country | Link |
|---|---|
| AT (5) | AT301244B (en) |
| BE (2) | BE710081A (en) |
| CH (5) | CH545293A (en) |
| CS (1) | CS162651B2 (en) |
| CY (1) | CY653A (en) |
| DE (2) | DE1695545C3 (en) |
| DK (1) | DK139940B (en) |
| ES (4) | ES350083A1 (en) |
| FI (1) | FI52859C (en) |
| FR (1) | FR1580153A (en) |
| GB (2) | GB1198942A (en) |
| IE (1) | IE31812B1 (en) |
| IT (1) | IT1044176B (en) |
| NL (1) | NL157015B (en) |
| NO (1) | NO126484B (en) |
| OA (1) | OA04036A (en) |
| SE (1) | SE346321B (en) |
| SU (1) | SU540569A3 (en) |
| YU (1) | YU33831B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3711608A (en) * | 1971-04-13 | 1973-01-16 | Merck & Co Inc | The treatment of pain, fever and inflammation with benzimidazoles |
| US3983130A (en) * | 1972-06-02 | 1976-09-28 | E. R. Squibb & Sons, Inc. | Anthelmintic isothiocyanobenzoxazoles |
| US3853894A (en) * | 1972-06-02 | 1974-12-10 | Squibb & Sons Inc | Isothiocyanobenzimidazoles |
| US3985755A (en) * | 1972-06-02 | 1976-10-12 | E. R. Squibb & Sons, Inc. | Pyridine containing isothiocyanobenzoxazoles |
| MA19290A1 (en) * | 1980-05-22 | 1982-04-01 | Ciba Geigy Ag | BENZOLE DERIVATIVES, THEIR PREPARATON AND THEIR THERAPEUTIC USES. |
| SE8604566D0 (en) * | 1986-10-27 | 1986-10-27 | Haessle Ab | NOVEL COMPUNDS |
| JP2006513159A (en) * | 2002-11-01 | 2006-04-20 | メルク エンド カムパニー インコーポレーテッド | Carbonylamino-benzimidazole derivatives as androgen receptor modulators |
| EP1675844A1 (en) * | 2003-10-23 | 2006-07-05 | Sterix Limited | Phenyl carboxamide and sulfonamide derivatives for use as 11-beta-hydroxysteroid dehydrogenase |
| GB0324792D0 (en) | 2003-10-23 | 2003-11-26 | Sterix Ltd | Compound |
-
1968
- 1968-01-16 IE IE48/68A patent/IE31812B1/en unknown
- 1968-01-30 FI FI680234A patent/FI52859C/en active
- 1968-01-30 BE BE710081D patent/BE710081A/xx not_active IP Right Cessation
- 1968-01-31 SE SE1277/68A patent/SE346321B/xx unknown
- 1968-02-01 GB GB46573/69A patent/GB1198942A/en not_active Expired
- 1968-02-01 IT IT34575/68A patent/IT1044176B/en active
- 1968-02-01 GB GB5259/68A patent/GB1198941A/en not_active Expired
- 1968-02-01 NL NL6801482.A patent/NL157015B/en not_active IP Right Cessation
- 1968-02-02 AT AT545270A patent/AT301244B/en not_active IP Right Cessation
- 1968-02-02 AT AT545070A patent/AT289828B/en not_active IP Right Cessation
- 1968-02-02 AT AT545170A patent/AT289833B/en not_active IP Right Cessation
- 1968-02-02 DK DK41168AA patent/DK139940B/en not_active IP Right Cessation
- 1968-02-02 DE DE1695545A patent/DE1695545C3/en not_active Expired
- 1968-02-02 CS CS815A patent/CS162651B2/cs unknown
- 1968-02-02 CH CH183971A patent/CH545293A/en not_active IP Right Cessation
- 1968-02-02 CH CH184071A patent/CH545294A/en not_active IP Right Cessation
- 1968-02-02 FR FR1580153D patent/FR1580153A/fr not_active Expired
- 1968-02-02 AT AT104468A patent/AT293378B/en active
- 1968-02-02 CH CH184171A patent/CH545295A/en not_active IP Right Cessation
- 1968-02-02 AT AT544970A patent/AT289835B/en not_active IP Right Cessation
- 1968-02-02 NO NO413/68*[A patent/NO126484B/no unknown
- 1968-02-02 ES ES350083A patent/ES350083A1/en not_active Expired
- 1968-02-02 CH CH159768A patent/CH509318A/en not_active IP Right Cessation
- 1968-02-02 DE DE1795711A patent/DE1795711C3/en not_active Expired
- 1968-02-02 CH CH184271A patent/CH545796A/xx not_active IP Right Cessation
- 1968-02-03 SU SU1215532A patent/SU540569A3/en active
- 1968-02-08 OA OA53178A patent/OA04036A/en unknown
- 1968-08-15 YU YU212/68A patent/YU33831B/en unknown
-
1969
- 1969-02-17 ES ES363761A patent/ES363761A1/en not_active Expired
- 1969-02-17 ES ES363760A patent/ES363760A1/en not_active Expired
- 1969-02-17 ES ES363762A patent/ES363762A1/en not_active Expired
- 1969-06-27 BE BE735281D patent/BE735281A/xx not_active IP Right Cessation
-
1972
- 1972-08-31 CY CY65372A patent/CY653A/en unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |