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US 7,459,566 B2Granted
1,2,4-oxadiazol-5-one-4-(benzimidazolylmethylamino)benzamidine compounds
AssigneeBoehringer Ingelheim International GmbH
InventorsGeorg Zerban, Arndt Hausherr, Kerstin Schlarb, Heinz-Peter Schmitt, Bjoern Weyell, Gunter Koch, Rainer Hamm
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Abstract
A process for preparing an optionally substituted 4-benzimidazol-2-ylmethylamino)benzamidine, the process comprising: (a) condensing an optionally suitably substituted diaminobenzene with 2-[4-(1,2,4-oxadiazol-5-on-3-yl)phenylamino]acetic acid; (b) hydrogenating the product obtained from step (a); and (c) optionally carboxylating the amidino group of the product obtained from step (b).
Claims4
A compound of formula (III)
- wherein:
- R1 is a C1-6-alkyl or C3-7-cycloalkyl group;
- and
- R2 is
- (i) a C1-6-alkyl group or a C3-7-cycloalkyl group optionally substituted by a C1-3-alkyl group, wherein the C1-3-alkyl group is optionally substituted by a carboxyl group or
- (ii) an R21NR22 group, wherein:
- R21 is a C1-6 alkyl group optionally substituted by a carboxy, C1-6 alkoxycarbonyl, benzyloxycarbonyl, C1-3-alkylsulfonylaminocarbonyl, phenylsulfonylaminocarbonyl, trifluorosulfonylamino, trifluorosulfonylaminocarbonyl, or 1H-tetrazolyl group, a C2-4-alkyl group substituted by a hydroxy, phenyl-C1-3-alkoxy, carboxy-C1-3-alkylamino, C1-3-alkoxycarbonyl-C1-3-alkylamino, N-(C1-3-alkyl)-carboxy-C1-3-alkylamino, or N-(C1-3-alkyl)-C1-3-alkoxycarbonyl-C1-3-alkylamino group, wherein the α-carbon atom to the adjacent nitrogen atom thereof is not substituted, or a piperidinyl group optionally substituted by a C1-3-alkyl group, and
- R22 is a hydrogen atom,
- a C1-6-alkyl group,
- a C3-7-cycloalkyl group optionally substituted by a C1-3-alkyl group,
- a C3-6-alkenyl, or C3-6-alkynyl group, wherein an unsaturated moiety of the C3-6-alkenyl or C3-6-alkynyl group is not linked directly to the nitrogen atom of the R21NR22 group,
- a phenyl group optionally substituted by a fluorine, chlorine, or bromine atom or by a C1-3-alkyl or C1-3-alkoxy group, or
- a benzyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, pyrrolyl, thienyl, or imidazolyl group optionally substituted by a C1-3-alkyl group;
- or
- R21 and R22 together with the nitrogen atom between them are a 5- to 7-membered cycloalkyleneimino group optionally substituted by a carboxy or C1-4-alkoxycarbonyl group, to which a phenyl ring is optionally additionally fused.
12 more elements
2-[4-(1,2,4-Oxadiazol-5-one-3-yl)phenylamino]acetic acid.
Dependencies are inferred from the claim text.