Substituted pyrrolobenzimidazoles for treating inflammatory diseases
First Claim
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1. A method of making a compound having the structure or a pharmaceutically acceptable salt thereof, wherein:
- (a) R1, R2 and R3 are independently selected from the group consisting of (i) hydrogen, (ii) C1-5alkyl, (iii) C1-5alkylamino, (iv) diC1-5alkylamino, (v) a phenyl substituted with one or more of hydrogen, halogen, C1-5alkyl, and trihaloC1-5alkyl, and (vi) a phenylC1-5alkyl substituted with one or more of hydrogen, halogen, C1-5alkyl, and trihaloC1-5alkyl;
(b) rings 1 and 2 are each independently substituted with one or more substituents selected from the group consisting of hydrogen, halogen, C1-5alkyl, and trihaloC1-5alkyl;
(c) A and B are independently nitrogen or carbon, at least one of A and B being nitrogen;
(d) D and E are nitrogen, with the proviso that (i) a double bond exists between the non-aryl carbon and either D or E, (ii) R2 is absent if the double bond exists between the non-aryl carbon and D, and (iii) R3 is absent if the double bond exists between the non-aryl carbon and E; and
(e) the compound is neither 1,6-dihydro-7-(4-pyridyl)-8-(4-fluorophenyl)-2-phenylmethyl-pyrrolo[3,2-e]benzimidazole, nor 3,6-dihydro-8-(4-fluorophenyl)-3-(3-phenylpropyl)-7-(4-pyridyl)-pyrrolo[3,2-e]benzimidazole;
said method comprising the step of contacting a first compound having the structure with a second compound having the structure under conditions permitting a Fischer indolization between the first and second compounds.
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Abstract
This invention provides compounds, and pharmaceutically acceptable salts thereof, having the structure shown below, as well as related pharmaceutical compositions, and methods of treatment and synthesis.
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Citations
1 Claim
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1. A method of making a compound having the structure
or a pharmaceutically acceptable salt thereof, wherein: -
(a) R1, R2 and R3 are independently selected from the group consisting of (i) hydrogen, (ii) C1-5alkyl, (iii) C1-5alkylamino, (iv) diC1-5alkylamino, (v) a phenyl substituted with one or more of hydrogen, halogen, C1-5alkyl, and trihaloC1-5alkyl, and (vi) a phenylC1-5alkyl substituted with one or more of hydrogen, halogen, C1-5alkyl, and trihaloC1-5alkyl;
(b) rings 1 and 2 are each independently substituted with one or more substituents selected from the group consisting of hydrogen, halogen, C1-5alkyl, and trihaloC1-5alkyl;
(c) A and B are independently nitrogen or carbon, at least one of A and B being nitrogen;
(d) D and E are nitrogen, with the proviso that (i) a double bond exists between the non-aryl carbon and either D or E, (ii) R2 is absent if the double bond exists between the non-aryl carbon and D, and (iii) R3 is absent if the double bond exists between the non-aryl carbon and E; and
(e) the compound is neither 1,6-dihydro-7-(4-pyridyl)-8-(4-fluorophenyl)-2-phenylmethyl-pyrrolo[3,2-e]benzimidazole, nor 3,6-dihydro-8-(4-fluorophenyl)-3-(3-phenylpropyl)-7-(4-pyridyl)-pyrrolo[3,2-e]benzimidazole;
said method comprising the step of contacting a first compound having the structure with a second compound having the structure under conditions permitting a Fischer indolization between the first and second compounds.
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Specification