Novel processes for producing sovaprevir
AssigneeAchillion Pharmaceuticals, Inc.
InventorsAvinash Phadke, Akihiro Hashimoto, Venkat Gadhachanda
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Abstract
The disclosure includes novel processes for producing Sovaprevir comprising adding compound E to F-1 to provide Sovaprevir. The disclosure further includes intermediates useful for producing Sovaprevir. The disclosure also include a novel crystalline form of Sovaprevir, Form F, and a method for preparing spray-dried amorphous Sovaprevir from crystalline Form F.
Claims26
A method of preparing sovaprevir comprising adding Compound F-1 to Compound E to provide Sovaprevir as follows:
A method of preparing a compound of formula (C) comprising at least Step 3 of the following 3 step process, wherein
- Step 1 comprises deprotecting Compound 13 with acid to provide Compound 14
- Step 2 comprises coupling R1H in base to Compound 14 to provide Compound 15;
- and
- Step 3 comprises demethylating Compound 15 with base to provide Compound C
- where,
- R1 is a 1-piperidinyl, 1-piperazinyl, or 1-pyrrolidinyl group, each of which is unsubstituted or substituted with 1 or 2 halogen substituents.
A method of preparing Compound F-2, comprising adding 4-chloro-7-methoxy-2-phenylquinoline (Compound D) to Compound C, to provide Compound F-2 as follows:
- where,
- R1 is a 1-piperidinyl, 1-piperazinyl, or 1-pyrrolidinyl group, each of which is unsubstituted or substituted with 1 or 2 halogen substituents.
A compound having the formula:
- where
- R1 is C1-C6alkyl or hydroxyl, or R1 is a 1-piperidinyl, 1-piperazinyl, or 1-pyrrolidinyl group, each of which is unsubstituted or substituted with 1 or 2 halogen substituents;
- and
- R2 is hydrogen or methyl.
A compound, having the Formula F
- where,
- R1 is a 1-piperidinyl, 1-piperazinyl, or 1-pyrrolidinyl group, each of which is unsubstituted or substituted with 1 or 2 halogen substituents;
- R2 is hydrogen or methyl.
A method of preparing a pure amorphous form of Sovaprevir, comprising
- crystallizing Sovaprevir in isopropyl alcohol to form Sovaprevir crystalline Form F;
- dissolving the Sovaprevir crystalline Form F in 6-12 volumes acetone;
- adding 6-13 volumes water relative to volume acetone;
- and
- precipitating amorphous Sovaprevir of greater than 98% purity.
A method of preparing a pure amorphous form of Sovaprevir, comprising
- crystallizing Sovaprevir in isopropyl alcohol to form Sovaprevir crystalline Form F;
- dissolving Form F in an acetone to form dissolved Sovaprevir;
- and
- spray drying the dissolved Sovaprevir to form an amorphous Sovaprevir of greater than 98% purity.
A crystalline Sovaprevir form, comprising polymorph Form F.
Dependencies are inferred from the claim text.