Process for making amino diaryl ethers and amino diaryl ethers hydrochloride salts
AssigneeCellestia Biotech AG
InventorsMichael BAUER, Uwe HAHN, Erhard BAPPERT
Life of this patent
Estimating the term…
Abstract
The present invention relates to a process for making a compound of formula (I) as described herein Formula (I) comprising reducing a compound of formula (II) as described herein with hydrogen in the presence of a palladium catalyst and a solvent wherein the solvent is a polar, aprotic solvent or a C3-C10 alcohol Formula (II). The present invention further relates to a hydrochloride salt and a monohydrochloride salt of the compound of formula (I) as described herein and to a process for making the same Formula (I).
Claims22
A process for making a compound of formula (I)
- wherein X is selected from O and NH;
- and
- wherein Y1, Y2 and Y3 are each independently selected from N and CH;
- and
- wherein R1 and R2 are each independently selected from H, C1-C10 alkyl and C3-C12 cycloalkyl;
- and
- wherein R3 and R4 are each independently selected from H, halogen and C1-C10 alkyl, comprising:
- reducing a compound of formula (II) with hydrogen in the presence of a palladium catalyst and a solvent wherein the solvent is a polar, aprotic solvent or a C3-C10 alcohol
- wherein X is selected from O and NH;
- and
- wherein Y1, Y2 and Y3 are each independently selected from N and CH;
- and
- wherein R11 and R22 are each independently selected from H, C1-C10 alkyl, and C3-C12 cycloalkyl;
- and
- wherein R33 and R44 are each independently selected from H, halogen and C1-C10 alkyl;
- to form said compound of formula (I).
The process according to claim 11, further comprising crystallizing said monohydrochloride salt.
A process for making a hydrochloride salt of the compound of formula (I)
- wherein X is selected from O and NH;
- and
- wherein Y1, Y2 and Y3 are each independently selected from N and CH;
- and
- wherein R1 and R2 are each independently selected from H, C1-C10 alkyl and C3-C12 cycloalkyl and
- wherein R3 and R4 are each independently selected from H, halogen and C1-C10 alkyl comprising reacting said compound of formula (I) with hydrochloric acid to form a hydrochloride salt of said compound of formula (I).
A process for making a monohydrochloride salt of the compound of formula (I)
- wherein X is selected from O and NH;
- and
- wherein Y1, Y2 and Y3 are each independently selected from N and CH;
- and
- wherein R1 and R2 are each independently selected from H, C1-C10 alkyl and C3-C12 cycloalkyl and
- wherein R3 and R4 are each independently selected from H, halogen and C1-C10 alkyl comprising reacting said compound of formula (I) with less than 1.5 molar equivalents of hydrochloric acid, to form the monohydrochloride salt of said compound of formula (I).
A hydrochloride salt of the compound of formula (I)
- wherein X is selected from O and NH;
- and
- wherein Y1, Y2 and Y3 are each independently selected from N and CH;
- and
- wherein R1 and R2 are each independently selected from H, C1-C10 alkyl and C3-C12 cycloalkyl and
- wherein R3 and R4 are each independently selected from H, halogen and C1-C10 alkyl.
A monohydrochloride salt of the compound of formula (I)
- wherein X is selected from O and NH;
- and
- wherein Y1, Y2 and Y3 are each independently selected from N and CH;
- and
- wherein R1 and R2 are each independently selected from H, C1-C10 alkyl and C3-C12 cycloalkyl and
- wherein R3 and R4 are each independently selected from H, halogen and C1-C10 alkyl.
Dependencies are inferred from the claim text.