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US 2026/0193181 A1Published application
Process for producing pyrrole compound
AssigneeTakeda Pharmaceutical Company Limited
InventorsTomomi Ikemoto, Hideya Mizufune, Toshiaki Nagata, Misayo Sera, Naohiro Fukuda, Takeshi Yamasaki
Life of this patent
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Abstract
The present invention provides a production method of a sulfonylpyrrole compound useful as a pharmaceutical product, a production method of an intermediate used for the method, and a novel intermediate. The present invention relates to a method of producing sulfonylpyrrole compound (VIII), which includes reducing compound (III) and hydrolyzing the reduced product to give compound (IV), subjecting compound (IV) to a sulfonylation reaction to give compound (VI), and subjecting compound (VI) to an amination reaction.
Claims12
1-5. (canceled)
A method of producing a compound represented by the formula
- wherein R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, and R2 is a hydrogen atom, an optionally substituted alkyl group, an acyl group, an optionally substituted hydroxy group, an optionally substituted amino group, a chlorine atom or a fluorine atom, or a salt thereof, comprising subjecting a compound represented by the formula
- wherein R1 and R2 are as defined above, R5 is an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, an acyl group or a group represented by —S—R6 (R6 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group), and n is 0, 1 or 2, or a salt thereof, to a desulfurization reaction.
(canceled)
A method of producing a compound represented by the formula
- wherein R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, and R2 is a hydrogen atom, an optionally substituted alkyl group, an acyl group, an optionally substituted hydroxy group, an optionally substituted amino group, a chlorine atom or a fluorine atom, or a salt thereof, comprising subjecting a compound represented by the formula
- wherein m is 0 or 1 and other symbols are as defined above, or a salt thereof, to a desulfurization reaction.
A method of producing a compound represented by the formula
- wherein R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, and R2 is a hydrogen atom, an optionally substituted alkyl group, an acyl group, an optionally substituted hydroxy group, an optionally substituted amino group, a chlorine atom or a fluorine atom, or a salt thereof, comprising reacting a compound represented by the formula
- wherein each symbol is as defined above, or a salt thereof, with a sulfur reagent to give a compound represented by the formula
- wherein m is 0 or 1, and other symbols are as defined above, or a salt thereof, and subjecting the obtained compound to a desulfurization reaction.
A method of producing a compound represented by the formula
- wherein R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R7 is a cyano group or a substituted carboxyl group, and R8 is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, a chlorine atom or a fluorine atom, or a salt thereof, comprising subjecting a compound represented by the formula
- wherein each symbol is as defined above, or a salt thereof, to a reduction reaction.
11-12. (canceled)
A method of producing a compound represented by the formula
- wherein R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, and R8 is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, a chlorine atom or a fluorine atom, or a salt thereof, comprising cyclizing a compound represented by the formula
- wherein each symbol is as defined above, or a salt thereof, in the presence of a reducing agent.
(canceled)
A compound represented by the formula
- wherein R1b is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R5 is an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, an acyl group or a group represented by —S—R6 (R6 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group), and n is 0, 1 or 2 (excluding 2,2′-dithiobis(5-methyl-1H-pyrrole-3-carbonitrile), 2,2′-dithiobis(5-phenyl-1H-pyrrole-3-carbonitrile), 2,2′-dithiobis[5-(4-chlorophenyl)-1H-pyrrole-3-carbonitrile], 2,2′-dithiobis[5-(4-methylphenyl)-1H-pyrrole-3-carbonitrile] and 2,2′-dithiobis[5-(4-methoxyphenyl)-1H-pyrrole-3-carbonitrile]), or a salt thereof.
A method of producing a compound represented by the formula
- wherein R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R2 is a hydrogen atom, an optionally substituted alkyl group, an acyl group, an optionally substituted hydroxy group, an optionally substituted amino group, a chlorine atom or a fluorine atom, R3 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, and R4 is an alkyl group, or a salt thereof, comprising (I) subjecting a compound represented by the formula:
- wherein R1 is as defined above, R7 is a cyano group, and R8 is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, a chlorine atom or a fluorine atom, or a salt thereof, to a reduction reaction, to give a compound represented by the formula:
- wherein each symbol is as defined above, or a salt thereof,
- (II) cycling the reduced product, to give a compound represented by the formula
- wherein each symbol is as defined above, or a salt thereof,
- (III) reducing the obtained compound and hydrolyzing the reduced product to give a compound represented by the formula
- wherein each symbol is as defined above, or a salt thereof,
- (IV) reacting the obtained compound with a compound represented by the formula
- wherein R3 is as defined above, and X is a leaving group, or a salt thereof, to give a compound represented by the formula
- wherein each symbol is as defined above, or a salt thereof, and
- (V) reacting the obtained compound with a compound represented by the formula R4—NH2 (VII) wherein R4 is as defined above, or a salt thereof in the presence of a reducing agent.
8 more elements
Dependencies are inferred from the claim text.