Process

• US 6,489,347 B1
• Filed: 05/29/1998
• Issued: 12/03/2002
• Est. Priority Date: 05/29/1997
• Status: Expired due to Fees

• Current Assignee: Smithkline Beecham PLC
• Original Assignee: Smithkline Beecham PLC
• Inventors: Shapiro, Evgeny, Yu, Marvin Sungwhan, Jacewicz, Victor Withold
• Primary Examiner(s): SEAMAN, D MARGARET M
• Application Number:
  US09/087,632
• Time in Patent Office: 1,649 Days
• Field of Search: 546/298, 546/301, 546/302, 546/322, 546/318, 546/315, 546/339, 514/350, 514/356, 514/355, 514/277
• US Class Current: 514/350
• CPC Class Codes: A61P 15/00 Drugs for genital or sexual disorders for disorders of sex hormones A61P5/24; Contraceptives
• CPC Class Codes: A61P 17/14 for baldness or alopecia
• CPC Class Codes: A61P 25/04 Centrally acting analgesics, e.g. opioids
• CPC Class Codes: A61P 25/06 Antimigraine agents
• CPC Class Codes: A61P 25/22 Anxiolytics
• CPC Class Codes: A61P 25/24 Antidepressants
• CPC Class Codes: A61P 25/28 for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
• CPC Class Codes: A61P 25/30 for treating abuse or dependence
• CPC Class Codes: A61P 25/32 Alcohol-abuse
• CPC Class Codes: A61P 3/04 Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 211/22 by oxygen atoms
• CPC Class Codes: C07D 211/74 Oxygen atoms
• CPC Class Codes: C07D 211/78 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links

Abstract

Compounds of structure (1) are obtained by reduction of compounds of the structures

Compounds of structure (1), especially where Z is a hydrogen atom or a 3,4-methylenedioxyphenyl group, are important intermediates for inter alia paroxetine.

Claims

1. A compound of structure (2a) or (2b)

in which:

in 2a

Y is oxygen or sulfur;

R is hydrogen or an alkyl, aralkyl, aryl, acyl, alkoxycarbonyl, arylalkoxycarbonyl, aryloxycarbonyl group;

X is hydrogen or from one to four reducible groups; and

Z is a 3,4-methylenedioxyphenyl group, and

in 2b

Y is sulfur;

R is hydrogen or an alkyl, aralkyl, aryl, acyl, alkoxycarbonyl, arylalkoxycarbonyl, aryloxycarbonyl group;

X is hydrogen or from one to four reducible groups; and

Z is a 3,4-methylenedioxyphenyl group.

2. A compound of structure (4a) or (4b)

in which

R is hydrogen or an alkyl, aralkyl, aryl, acyl, alkoxycarbonyl, arylalkoxycarbonyl, aryloxycarbonyl group;

X is hydrogen or from one to four reducible groups; and

Z is a 3,4-methylenedioxyphenyl group.

3. A compound of structure (4c) or (4d)

in which

R is hydrogen or an alkyl, aralkyl, acyl, alkoxycarbonyl, arylalkoxycarbonyl, aryloxycarbonyl group;

and

X is hydrogen or from one to four reducible groups.