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US 2009/0264663 A1Published application
3-HYDROXYMETHYLBENZO[b]THIOPHENE DERIVATIVES AND PROCESS FOR THEIR PRODUCTION
AssigneeTeijen Pharma Limited
InventorsNaoki Yajima, Yasuhiro Hiroki, Hiroshi Yoshino, Tatsuya Koizumi
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Abstract
The invention provides 3-hydroxymethylbenzo[b]thiophene derivatives useful as production intermediates for chymase inhibitors, and a process for their production. The invention relates to 3-hydroxymethylbenzo[b]thiophene derivatives represented by the following formula (II), and a process for their production.
Claims21
A production process in which a compound represented by the following formula (I):
- wherein
- R1 represents C1-6 alkyl, C1-6 halogenated alkyl, a halogen atom, cyano, C1-6 alkoxy, C1-6 alkylthio, C1-6 acyloxy, C1-6 acylamino or C1-6 halogenated alkoxy;
- and
- R2, R3 and R4 simultaneously or each independently represent hydrogen, C1-6 alkyl, C1-6 halogenated alkyl, a halogen atom, cyano, C1-6 alkoxy, C1-6 alkylthio, C1-6 acyloxy, C1-6 acylamino or C1-6 halogenated alkoxy;
- and
- R5 represents hydrogen or a C1-6 alkyl group;
- is reduced to obtain a 3-hydroxymethylbenzo[b]thiophene derivative represented by the following formula (II):
- wherein R1, R2, R3 and R4 are as defined in formula (I).
5 more elements
A production process for benzimidazole derivatives represented by formula (XX), which includes the following production steps:
- (i) a production process for a compound represented by formula (II), according to claim;
- and
- (ii) a process in which a benzimidazole derivative represented by formula (XX) is produced from the compound represented by formula (II);
- in formula (XX),
- R23 and R24 simultaneously or each independently represent a hydrogen atom, a halogen atom, trihalomethyl, cyano, hydroxyl, C1-4 alkyl or C1-4 alkoxy, or R23 and R24 may together form —O—CH2O—, —O—CH2CH2O— or —CH2CH2CH2— (in which case the carbon atoms may be optionally substituted with one or more C1-4 alkyl groups);
- A represents a substituted or unsubstituted C1-7 straight-chain, cyclic or branched alkylene group or alkenylene group, which may include one or more group(s) selected from the group consisting of —O—, —S—, —SO2— and —NR25— (where R25 represents a hydrogen atom or a straight-chain or branched C1-6 alkyl group), and the substituent(s) on the groups may be a halogen atom or hydroxyl, nitro, cyano, straight-chain or branched C1-6 alkyl or straight-chain or branched C1-6 alkoxy groups (including cases where two adjacent groups form an acetal bond), straight-chain or branched C1-6 alkylthio, straight-chain or branched C1-6 alkylsulfonyl, straight-chain or branched C1-6 acyl, straight-chain or branched C1-6 acylamino, trihalomethyl, trihalomethoxy, phenyl, oxo or phenoxy optionally substituted with one or more halogen atom(s), and one or more of the substituents at any desired position of the alkylene or alkenylene group may be independently substituted, with the exclusion of cases where M in the formula is a single bond, and carbons of A bonded to M are simultaneously substituted with hydroxyl and phenyl groups;
- E represents —COOR25, —SO3R25, —CONHR25, —SO2NHR25, tetrazol-5-yl, 5-oxo-1,2,4-oxadiazol-3-yl or 5-oxo-1,2,4-thiadiazol-3-yl (where R25 is as defined above);
- M represents a single bond or —S(O)m—, where m is an integer of 0-2;
- G and J both represent formula (II) above, with G representing the methylene group at position 3 of the benzothiophene of formula (II), and the hydroxyl group of formula (II) is substituted for the nitrogen atom on the benzimidazole ring;
- and
- X represents —CH═ or a nitrogen atom.
8 more elements
A compound represented by the following formula (I):
- wherein R1, R2, R3, R4 and R5 are as defined above.
Dependencies are inferred from the claim text.