右旋性ベンジルアルコールとその適当な塩の製造プロセスおよび化合物

Title:

右旋性ベンジルアルコールとその適当な塩の製造プロセスおよび化合物

Document Type and Number:

Japanese Patent JP4002180

Kind Code:

B2

Abstract:

Optically active 3,3-diarylpropylamine derivatives are produced in six steps from 4-hydroxybenzoic acid or an alkyl 4-hydroxybenzoate and cinnamic acid via new and known phenyl-chromanone and phenyl-chromanol compounds. Production of optically active 3,3-diarylpropylamine derivatives of formula (I) comprises: (A) condensation of 4-hydroxybenzoic acid or an alkyl 4-hydroxybenzoate (II) with cinnamic acid; (B) reaction of the resulting (R,S)-2-oxo-4-phenylchromane of formula (III) with cinchonidine; (C) acidification of the (R)-2-oxo-4-phenylchromane cinchonidine salt of formula (IV) obtained; (D) isolation of the resulting (R)-6-carboxy-2-oxo-4-phenylchromane (V) and reaction of this, after conversion into an activated form, with an alcohol (VI); (E) reduction of the alkyl (R)-2-oxo-4-phenylchromane-6-carboxylate (VII) obtained with diisobutylaluminum hydride or lithium tri-tert.butoxyaluminum hydride; and (F) reductive amination of the resulting lactol (VIII) with a primary, secondary or tertiary amine. [Image] [Image] R : H; or 1-6C alkyl, preferably methyl or isopropyl, but R in compound (VI) is 1-6C alkyl); R', R'' and R 1>1-6C alkyl, preferably methyl or isopropyl. Independent claims are also included for: (a) the (R,S)-2-oxo-4-phenylchromane (III) (R = H); (b) the (R)-2-oxo-4-phenylchromane cinchonidine salt (IV); (c) the (R)-6-carboxy-2-oxo-4-phenylchromane (V); and (d) the (R)-hydroxybenzyl alcohol salt of formula (IX). [Image] - ACTIVITY : Uropathic. - MECHANISM OF ACTION : None given in the source material.

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Inventors:

Mese, Claus

Application Number:

JP2002510423A

Publication Date:

October 31, 2007

Filing Date:

June 11, 2001

Export Citation:

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Assignee:

SCHWARZ PHARMA AKTIENGESELLSCHAFT

International Classes:

C07C227/08; A61K31/137; A61P13/00; C07B53/00; C07B55/00; C07B61/00; C07C213/08; C07C215/54; C07C215/66; C07C227/30; C07C229/38; C07D311/20; C07D453/04

Domestic Patent References:

JP8503208A

Attorney, Agent or Firm:

Hironobu Onda
Makoto Onda

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