3-(4'-substituted)-benzyl-ether derivatives of pregnenolone
AssigneesInserm (Institut National De La Sante Et De La Recherche Medicale), Sc Belenos, Universite De Bordeaux
InventorsPier Vincenzo PIAZZA, Monique VALLEE, Francois-Xavier FELPIN, Jean-Michel REVEST, Sandy FABRE
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Abstract
The invention relates to a compound of Formula (I), or a pharmaceutically acceptable salt thereof: wherein R1 is C1-8 alkyl, C1-8 alkoxy, CN, NO2, amino, COOH, COOCH3, OH, N3, or halogen and R2 is H, OH, C1-8 alkyl, C1-8 alkoxy, C2-C6 alkenyl, halogen, Bn-O—, Bn- optionally substituted, or Ph- optionally substituted.
Claims20
A compound of Formula I or a pharmaceutically acceptable salt thereof,
- wherein:
- R1 is selected from the group consisting of C1-8 alkyl, C1-8 alkoxy, CN, NO2, amino, COOH, COOCH3, OH, N3, and halogen;
- and
- R2 is selected from the group consisting of H;
- OH;
- C1-8 alkyl;
- C1-8 alkoxy;
- C2-6 alkenyl;
- halogen;
- Bn-O—;
- Bn- optionally substituted with C1-8 alkyl, C1-8 alkoxy, CN, NO2, amino, COOH, or halogen;
- and Ph- optionally substituted with C1-8 alkyl, C1-8 alkoxy, CN, NO2, amino, COOH, or halogen;
- with the proviso that when R1 is methoxy, R2 is not H.
A process for the manufacture of a compound of Formula I:
- or a pharmaceutically acceptable salt thereof,
- which comprises reacting a compound of Formula III:
- with a compound of Formula IV:
- in the presence of methyl triflate and/or a heterogeneous acid scavenger;
- or
- with a compound of Formula V
- in the presence of a heterogeneous acid scavenger;
- wherein:
- R1 is selected from the group consisting of C1-8 alkyl;
- C1-8 alkoxy;
- CN;
- NO2;
- amino;
- COOH;
- COOCH3;
- OH;
- N3;
- and halogen;
- and
- R2 is selected from the group consisting of H;
- OH;
- C1-8 alkyl;
- C1-8 alkoxy;
- C2-6 alkenyl;
- halogen;
- Bn-O—;
- Bn- optionally substituted with C1-8 alkyl, C1-8 alkoxy, CN, NO2, amino, COOH, or halogen;
- and Ph- optionally substituted with C1-8 alkyl, C1-8 alkoxy, CN, NO2, amino, COOH, or halogen.
A method for treating a human or animal suffering from a pathology, comprising a step of administering a compound of Formula I, or a pharmaceutically acceptable salt thereof, to a human or animal in need thereof
- wherein:
- R1 is selected from the group consisting of C1-8 alkyl;
- C1-8 alkoxy;
- CN;
- NO2;
- amino;
- COOH;
- COOCH3;
- OH;
- N3;
- and halogen;
- and
- R2 is selected from the group consisting of H;
- OH;
- C1-8 alkyl;
- C1-8 alkoxy;
- C2-6 alkenyl;
- halogen;
- Bn-O—;
- Bn- optionally substituted with C1-8 alkyl, C1-8 alkoxy, CN, NO2, amino, COOH, or halogen;
- and Ph- optionally substituted with C1-8 alkyl, C1-8 alkoxy, CN, NO2, amino, COOH, or halogen.
Dependencies are inferred from the claim text.