US 6,982,275 B2 | ||
Process for producing optically active sulfoxide derivative | ||
Hideo Hashimoto, Kobe (Japan); and Tadashi Urai, Takatsuki (Japan) | ||
Assigned to Takeda Pharmaceutical Company Limited, Osaka (Japan) | ||
Appl. No. 10/276,109 PCT Filed Apr. 26, 2001, PCT No. PCT/JP01/03613 § 371(c)(1), (2), (4) Date Oct. 24, 2002, PCT Pub. No. WO01/83473, PCT Pub. Date Nov. 08, 2001. |
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Claims priority of application No. 2000-128760 (JP), filed on Apr. 28, 2000. | ||
Prior Publication US 2003/0171591 A1, Sep. 11, 2003 | ||
Int. Cl. A61K 31/4439 (2006.01); A61K 31/4184 (2006.01); A61K 31/44 (2006.01); C07D 209/30 (2006.01); C07D 401/12 (2006.01); C07D 235/28 (2006.01) |
U.S. Cl. 514—339 | 13 Claims |
1. A method for producing an optically active form of a compound represented by the formula (II): ![]() wherein ring A is a benzene ring optionally having 1 to 3 substituent(s) selected from (a) a halogen atom, (b) a cyano, (c) a nitro,
(d) an alkyl optionally having 1 to 3 substituent(s) selected from a halogen atom, a hydroxy, a C1-6 alkoxy, a C1-6 alkoxy-carbonyl and a carbamoyl, (e) a hydroxy, (f) an alkoxy optionally having 1 to 3 substituent(s) selected from a halogen
atom, a hydroxy, a C1-6 alkoxy, a C1-6 alkoxy-carbonyl and a carbamoyl, (g) an aryl, (h) an aryloxy, (i) a carboxy, (j) an acyl, (k) an acyloxy and (l) a 5- to 10-membered
heterocyclic group,
R1 is a hydrogen atom; a hydrocarbon group selected from (A) an alkyl group, an alkenyl group and an alkynyl group, each of which
optionally has 1 to 3 substituent(s) selected from (a) an alkylthio group, (b) a halogen, (c) an alkoxy group, (d) an acyloxy
group, (e) a nitro group, (f) an alkoxy-carbonyl group, (g) an alkylamino group, (h) an alkoxyimino group and (i) a hydroxyimino,
and (B) an aryl group and an aralkyl group, each of which optionally has 1 to 5 substituent(s) selected from (a) an alkyl
group, (b) an alkenyl group, (c) an alkynyl group, (d) an alkoxy group, (e) an acyl group, (f) a nitro, (g) an amino, (h)
a hydroxy, (i) a cyano, (j) a sulfamoyl, (k) a mercapto, (l) a halogen and (m) an alkylthio group; an acyl group or an acyloxy
group,
R2, R3 and R4 are each a hydrogen atom; an alkyl group optionally having 1 to 3 substituent(s) selected from a halogen atom, a hydroxy,
a C1-6 alkoxy, a C1-6 alkoxy-carbonyl and a carbamoyl; an alkoxy group optionally having 1 to 3 substituent(s) selected from a halogen atom, a hydroxy,
a C1-6 alkoxy, a C1-6 alkoxy-carbonyl and a carbamoyl; an amino; a mono-C1-6 alkylamino; a mono-C6-14 arylamino; a di-C1-6 alkylamino or a di-C6-14 arylamino,
X is a nitrogen atom or CH,
Y is a nitrogen atom or CH, and
* is an asymmetric center, or a salt thereof,
comprising reacting a compound represented by the formula (I):
![]() wherein each symbol is as defined above, or a salt thereof,
with an excess amount of an oxidizing agent in the presence of a catalyst for asymmetric induction and a base;
wherein the amount of the oxidizing agent to be used is about 1.5 to about 10 molar equivalents relative to the compound represented
by the formula (I) or a salt thereof.
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