GB1198941A - Benzimidazole Derivatives - Google Patents

Benzimidazole Derivatives

Info

Publication number
GB1198941A
GB1198941A GB5259/68A GB525968A GB1198941A GB 1198941 A GB1198941 A GB 1198941A GB 5259/68 A GB5259/68 A GB 5259/68A GB 525968 A GB525968 A GB 525968A GB 1198941 A GB1198941 A GB 1198941A
Authority
GB
United Kingdom
Prior art keywords
compound
benzimidazole
reacting
give
appropriate
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
Application number
GB5259/68A
Inventor
D R Hoff
H Fisher
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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.)
Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1198941A publication Critical patent/GB1198941A/en
Expired legal-status Critical Current

Links

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 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

Abstract

1,198,941. Benzimidazole derivatives. MERCK & CO. Inc. 1 Feb., 1968 [3 Feb., 1967; 9 Jan., 1968], No. 5259/68. Heading C2C. Novel compounds (I) in which X is O or S; 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 alkyl, C 1-8 alkoxy, aralkyl, acyl, acyloxy, carboxyalkoxy, carbamoyl, N-alkylcarbamoyl, or alkoxycarbonyl; R 3 is H, or C 1-8 alkyl and R 4 is H, aralkyl, haloaralkyl, cycloalkyl, C 1-8 alkylamino, di - (C 1-8 alkyl)amino, alkylenimino, hetero - interrupted alkylenimino, cycloalkylamino or a radical R-, RO- or RS- in which R is a C 1-8 univalent aliphatic hydrocarbon, C 1-8 univalent aliphatic halohydrocarbon, aryl, haloaryl, alkaryl, aminoaryl or heterocyclic radical and their acid addition salts and metal complexes when R 2 is H are prepared by: (a) reacting an appropriate 5- NH(R 3 )-substituted benzimidazole with R 4 - C(X)Y where Y is a halogen atom; (b) reacting an appropriate 5-RS-CO-N(R 3 )- substituted benzimidazole with a compound ROH to give a compound (I) in which X is O and R 4 is RO (R being radical R from ROH); (c) reacting an appropriate 5-isothiocyanato benzimidazole with a compound ROH or RSH to give a compound (I) in which X is S and R 4 is RO- or RS-; (d) reacting a compound (I) in which X is O with phosphorus pentasulphide to give a compound (I) in which X is S; (e) reacting an appropriate 5-NH(R 3 )- substituted benzimidazole with an alkyl isocyanate or isothiocyanate to give a compound (I) in which R 4 is alkylamino; (f) reacting an appropriate 5-NH(R 3 )- substituted benzimidazole with a dialkylcarbamoyl halide to give a compound (I) in which X is O and R 4 is dialkylamino; (g) reacting a compound (I) in which X is O and R 4 is alkylthio with a dialkylamine, alkylenimine or hetero-interrupted alkylenimine to give a compound (I) in which R 4 is dialkylamino, alkylenimino or hetero-interrupted alkylenimino; (h) reacting an appropriate 5- isothiocyanato-benzimidazole with a dialkylamine, alkylenimine or hetero-interrupted alkylenimine to give a compound (I) in which X is S and R 4 is dialkylamino, alkylenimino or hetero-interrupted alkylenimino; or (i) introducing the group R 2 into an appropriate benzimidazole by reacting an alkali metal salt of a compound (I) in which R 2 is H with an alkyl, aralkyl or acyl halide, or by reacting a compound (I) in which R 2 is H with an alkyl isocyanate to give a compound (I) where R 2 is carbamoyl, or by reacting a compound (I) in which R 2 is H with an alkyl haloformate to give a compound (I) in which R 2 is alkoxycarbonyl; followed in any of (a)-(i) by salt formation, where desired. Intermediates isolated are 5-nitro-2-(4<SP>1</SP>-thiazolyl)-benzimidazole, prepared by nitration of the 5 - unsubstituted compound; 5 - nitro - 2 - (2<SP>1</SP> - furyl) - benzimidazole, 5 - nitro - 2 - (2<SP>1</SP>- pyrryl) - benzimidazole and 5 - nitro - 2 - (2<SP>1</SP>- thienyl) - benzimidazole, prepared by reacting the appropriate furan-, pyrrole- or thiophene- 2 - aldehyde with o - amino - p - nitro - aniline; 5 - amino - 2 - (4<SP>1 </SP>- thiazolyl) - benzimidazole, prepared by reduction of the 5-nitro compound; 5 - isothiocyanato - 2 - (4<SP>1 </SP>- thiazolyl) - benzimidazole, prepared from the 5-phenoxythiocarbonylamino compound by heating in pyridino; 5 - nitro - 1 - methoxy - 2 - (4<SP>1 </SP>- thiazolyl)- benzimidazole, prepared by nitration of the 5- unsubstituted compound and 5-amino-1-methoxy - 2 - (4<SP>1</SP>- thiazolyl) - benzimidazole hydrochloride, prepared by reduction of the previous intermediate. Pharmaceutical compositions comprise a novel compound (I) in conjunction with a suitable carrier or diluent and are suitable for oral or parenteral administration as anthelmintics or antifungal agents.
GB5259/68A 1967-02-03 1968-02-01 Benzimidazole Derivatives Expired GB1198941A (en)

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
GB1198941A true GB1198941A (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 Before (1)

Application Number Title Priority Date Filing Date
GB46573/69A Expired GB1198942A (en) 1967-02-03 1968-02-01 Benzimidazole Derivatives

Country Status (19)

Country Link
AT (5) AT289828B (en)
BE (2) BE710081A (en)
CH (5) CH545295A (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)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3853894A (en) * 1972-06-02 1974-12-10 Squibb & Sons Inc Isothiocyanobenzimidazoles
USB486280I5 (en) * 1972-06-02 1976-02-03
US3985755A (en) * 1972-06-02 1976-10-12 E. R. Squibb & Sons, Inc. Pyridine containing isothiocyanobenzoxazoles
WO2005042513A1 (en) * 2003-10-23 2005-05-12 Sterix Limited Phenyl carboxamide and sulfonamide derivatives for use as 11-beta-hydroxysteroid dehydrogenase
EP1581217A1 (en) * 2002-11-01 2005-10-05 Merck & Co., Inc. Carbonylamino-benzimidazole derivatives as androgen receptor modulators
US7230020B2 (en) 2003-10-23 2007-06-12 Sterix Limited 11β-hydroxysteroid dehydrogenase inhibitors

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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
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

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3853894A (en) * 1972-06-02 1974-12-10 Squibb & Sons Inc Isothiocyanobenzimidazoles
USB486280I5 (en) * 1972-06-02 1976-02-03
US3983130A (en) 1972-06-02 1976-09-28 E. R. Squibb & Sons, Inc. Anthelmintic isothiocyanobenzoxazoles
US3985755A (en) * 1972-06-02 1976-10-12 E. R. Squibb & Sons, Inc. Pyridine containing isothiocyanobenzoxazoles
EP1581217A1 (en) * 2002-11-01 2005-10-05 Merck & Co., Inc. Carbonylamino-benzimidazole derivatives as androgen receptor modulators
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
EP1581217A4 (en) * 2002-11-01 2007-07-11 Merck & Co Inc Carbonylamino-benzimidazole derivatives as androgen receptor modulators
AU2003286757B2 (en) * 2002-11-01 2009-06-04 Merck Sharp & Dohme Corp. Carbonylamino-benzimidazole derivatives as androgen receptor modulators
US7622592B2 (en) 2002-11-01 2009-11-24 Merck & Co., Inc. Carbonylamino-benzimidazole derivatives as androgen receptor modulators
WO2005042513A1 (en) * 2003-10-23 2005-05-12 Sterix Limited Phenyl carboxamide and sulfonamide derivatives for use as 11-beta-hydroxysteroid dehydrogenase
US7230020B2 (en) 2003-10-23 2007-06-12 Sterix Limited 11β-hydroxysteroid dehydrogenase inhibitors

Also Published As

Publication number Publication date
SE346321B (en) 1972-07-03
BE735281A (en) 1969-12-29
CY653A (en) 1972-08-31
ES363760A1 (en) 1970-12-16
CH545796A (en) 1974-02-15
AT293378B (en) 1971-10-11
DE1795711C3 (en) 1979-05-17
DE1695545A1 (en) 1971-05-06
AT289835B (en) 1971-05-10
CH509318A (en) 1971-06-30
AT289833B (en) 1971-05-10
BE710081A (en) 1968-07-30
IT1044176B (en) 1980-03-20
OA04036A (en) 1979-09-30
NL6801482A (en) 1968-08-05
DE1695545B2 (en) 1978-08-31
IE31812L (en) 1968-08-03
CS162651B2 (en) 1975-07-15
NO126484B (en) 1973-02-12
AT301244B (en) 1972-08-25
CH545295A (en) 1974-01-31
FI52859B (en) 1977-08-31
DK139940C (en) 1979-10-15
CH545293A (en) 1974-01-31
ES363762A1 (en) 1970-12-16
YU21268A (en) 1977-12-31
AT289828B (en) 1971-05-10
ES363761A1 (en) 1970-12-16
ES350083A1 (en) 1969-11-16
CH545294A (en) 1974-01-31
FI52859C (en) 1977-12-12
DK139940B (en) 1979-05-21
GB1198942A (en) 1970-07-15
NL157015B (en) 1978-06-15
DE1795711A1 (en) 1974-02-28
YU33831B (en) 1978-06-30
DE1695545C3 (en) 1979-05-03
IE31812B1 (en) 1973-01-10
SU540569A3 (en) 1976-12-25
DE1795711B2 (en) 1978-09-21
FR1580153A (en) 1969-09-05

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Legal Events

Date Code Title Description
PS Patent sealed
48S Specification amended (sect. 8/1949)
PCNP Patent ceased through non-payment of renewal fee