Naphthylethylureas and naphthylethylthioureas

• US 5,449,690 A
• Filed: 12/20/1994
• Issued: 09/12/1995
• Est. Priority Date: 08/23/1991
• Status: Expired due to Fees

• Current Assignee: Les Laboratoires Servier (Servier Sas)
• Original Assignee: Adir SA
• Inventors: Adam, Gerard, Guardiola-Lemaitre, Beatrice, DePreux, Patrick, Yous, Said, Pfeiffer, Bruno, Renard, Pierre, Lesieur, Daniel
• Primary Examiner(s): Kumar, Shailendra
• Application Number:
  US08/359,605
• Time in Patent Office: 266 Days
• Field of Search: 514/595, 514/596, 514/588, 514/923
• US Class Current: 514/596
• CPC Class Codes: A61K 8/42 Amides
• CPC Class Codes: A61K 8/46 containing sulfur A61K8/44 takes precedence
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• 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 25/20 Hypnotics; Sedatives
• CPC Class Codes: A61P 25/24 Antidepressants
• CPC Class Codes: A61P 25/26 Psychostimulants, e.g. nicotine, cocaine
• 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 35/00 Antineoplastic agents
• CPC Class Codes: A61Q 17/00 Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 7/00 Preparations for affecting hair growth
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 275/24 containing six-membered aromatic rings
• CPC Class Codes: C07C 335/12 the carbon skeleton containing six-membered aromatic rings

Abstract

A compound selected from those of formula (I): ##STR1## in which the meanings of R, R₁, R₂ and X are as defined in the specification, and medicinal products containing the same which are useful in treating or in preventing a disorder of the melatoninergic system.

Claims

1. A method of treating a mammal afflicted with a disorder of the melatoninergic system selected from sleep and seasonal disorders comprising the step of administering to the said mammal an amount of a compound selected from those of formula I ##STR4## in which:

R represents hydrogen or a group OR₃ wherein R₃ represents hydrogen, straight-chained or branched alkyl having 1 to 6 carbon atoms inclusive, cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms inclusive, unsubstituted or optionally-substituted aryl, or unsubstituted or optionally-substituted arylalkyl or diarylalkyl in which the alkyl chain has 1 to 6 carbon atoms inclusive;

R₁ represents hydrogen or straight-chained or branched alkyl having 1 to 6 carbon atoms inclusive;

X represents oxygen;

R₂ represents linear or branched lower alkyl having 1 to 6 carbon atoms inclusive, unsubstituted or optionally-substituted cycloalkyl having 3 to 8 carbon atoms inclusive, unsubstituted or optionally-substituted (C₃ -C₈)-cycloalkyl-(C₁ -C₆)-alkyl, unsubstituted or optionally-substituted aryl, unsubstituted or optionally-substituted arylalkyl the alkyl chain of which has 1 to 6 carbon atoms inclusive, or unsubstituted or optionally-substituted diarylalkyl the alkyl chain of which has 1 to 6 carbon atoms inclusive,

addition salts thereof with a pharmaceutically-acceptable base, and

optical isomers, epimers and diastereoisomers thereof,

wherein

the term "substituted" associated with the expressions "aryl", "arylalkyl" and "diarylalkyl" means that the aromatic nucleus or nuclei may be substituted by one or more groups selected from linear or branched lower alkyl having 1 to 6 carbon atoms inclusive, linear or branched lower alkoxy having 1 to 6 carbon atoms inclusive, hydroxy, halogen, nitro, and trifluoromethyl;

the term "substituted" associated with the expressions "cycloalkyl" and "cycloalkylalkyl" means that the cyclic system may be substituted by one or more groups selected from halogen, linear or branched lower alkyl having 1 to 6 carbon atoms inclusive, and linear or branched lower alkoxy having 1 to 6 carbon atoms inclusive, and

the term "aryl" means phenyl or naphthyl which is effective for alleviation of said disorder.

2. A method of claim 1 wherein the compound is selected from those in which R represents hydrogen, hydroxy, or methoxy and R₁ represents hydrogen, addition salts thereof with a pharmaceutically-acceptable base, and optical isomers, epimers and diastereoisomers thereof.

3. A method of claim 1 wherein the compound is N-[2-(7-methoxynaphth-1-yl)ethyl]-N'"'"'-propylurea.

4. A method of claim 1 wherein the compound is N-[2-(7-methoxynaphth-1-yl)ethyl]-N'"'"'-methylurea.

5. A method of claim 1 wherein the compound is N-[2-(7-methoxynaphth-1-yl)ethyl]-N'"'"'-ethylurea.

6. A method of claim 1 wherein the compound is N-[2-(7-methoxynaphth-1-yl)ethyl]-N'"'"'-butylurea.

7. A method of claim 1 wherein the compound is N-[2-(naphthlyl)ethyl]-N'"'"'-propylurea.

8. A method of claim 1 wherein the compound is N-[2-(naphthlyl)ethyl]-N'"'"'-butylurea.