ANXIOLYTIC AGENTS WITH REDUCED SEDATIVE AND ATAXIC EFFECTS

• US 20070049580A1
• Filed: 07/20/2006
• Published: 03/01/2007
• Est. Priority Date: 03/28/2002
• Status: Abandoned Application

• Current Assignee: WiSys Technology Foundation, Inc.
• Original Assignee: WiSys Technology Foundation, Inc.
• Inventors: Yu, Jianming, He, Xiaohui, Huang, Qi, Han, Dongmei, Li, Xioayan, COOK, James
• Application Number:
  US11/458,855
• Publication Number:
  US 20070049580A1
• Time in Patent Office: Days
• US Class Current: 514/220
• CPC Class Codes: A61P 1/08 for nausea, cinetosis or vertigo; Antiemetics
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/18 Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
• CPC Class Codes: A61P 25/22 Anxiolytics
• CPC Class Codes: C07D 243/12 1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
• CPC Class Codes: C07D 243/20 Nitrogen atoms
• CPC Class Codes: C07D 243/24 Oxygen atoms
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C07D 487/06 Peri-condensed systems
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• CPC Class Codes: C07D 495/14 Ortho-condensed systems
• CPC Class Codes: C07D 498/04 Ortho-condensed systems
• CPC Class Codes: C07D 519/00 Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Abstract

Orally active benzodiazepine derivatives and their salts are disclosed. These compounds and their salts have anxiolytic and anticonvulsant activity with reduced sedative/hypnotic/muscle relaxant/ataxic effects.

Claims

1. A compound of the following formula, or a salt thereof:

wherein

R is hydrogen, methyl, trimethylsilyl, isopropyl, cyclopropyl, or t-butyl;

R¹ is hydrogen, methyl, trifluoromethyl, ethyl, trifluoroethyl, propargyl, an alkyl, or cyclopropyl;

R² is a substituted or unsubstituted at least partially unsaturated 5 membered or 6 membered carbocyclic ring or 5 membered or 6 membered heterocyclic ring having at least one heteroatom selected from N, O and S, wherein if substituted the substituent is one or more of F, Cl, Br, or NO₂ at the 2′

-position;

R⁵ is a branched or straight chain C₁ to C₄ halogenated or unhalogenated alkyl, a methyl cyclopropyl or a substituted or unsubstituted at least partially unsaturated 5 membered or 6 membered carbocyclic ring or 5 membered or 6 membered heterocyclic ring having at least one heteroatom selected from N, O and S.

2. The compound according to claim 1, wherein said compound is

3. The compound according to claim 1, wherein R² is phenyl or pyridinyl substituted at the 2′

-position with 0-1 substituents selected from fluoro, chloro, bromo, and nitro.

4. The compound of claim 1, wherein R is hydrogen.

5. The compound of claim 1, wherein R¹ is hydrogen.

6. The compound of claim 1, wherein R² is phenyl.

7. The compound of claim 1, wherein R⁵ is ethyl.

8. The compound of claim 1, wherein said compound is ethyl 8-acetylenyl-6-phenyl-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate.