Derivatives of 4-aminopiperidine and their use as a medicament

• US 8,110,574 B2
• Filed: 11/15/2010
• Issued: 02/07/2012
• Est. Priority Date: 12/14/1999
• Status: Expired due to Term

• Current Assignee: Ipsen Pharma Sas (Ipsen Sa)
• Original Assignee: Ipsen Pharma Sas (Ipsen Sa)
• Inventors: Thurieau, Christophe, Moinet, Christophe, Gonzalez, Jérôme
• Primary Examiner(s): SAEED, KAMAL A
• Application Number:
  US12/946,504
• Publication Number:
  US 20110059971A1
• Time in Patent Office: 449 Days
• Field of Search: None
• US Class Current: 514/237.2
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 1/02 Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
• CPC Class Codes: A61P 1/12 Antidiarrhoeals
• CPC Class Codes: A61P 1/18 for pancreatic disorders, e.g. pancreatic enzymes
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 13/12 of the kidneys
• CPC Class Codes: A61P 15/00 Drugs for genital or sexual disorders for disorders of sex hormones A61P5/24; Contraceptives
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 19/00 Drugs for skeletal disorders
• CPC Class Codes: A61P 19/08 for bone diseases, e.g. rachitism, Paget's disease
• CPC Class Codes: A61P 19/10 for osteoporosis
• CPC Class Codes: A61P 25/04 Centrally acting analgesics, e.g. opioids
• CPC Class Codes: A61P 25/06 Antimigraine agents
• CPC Class Codes: A61P 25/28 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 3/04 Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 35/02 specific for leukemia
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 5/00 Drugs for disorders of the endocrine system
• CPC Class Codes: A61P 5/02 : of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
• CPC Class Codes: A61P 5/04 : for decreasing, blocking or antagonising the activity of the hypothalamic hormones
• CPC Class Codes: A61P 5/08 : for decreasing, blocking or antagonising the activity of the anterior pituitary hormones
• CPC Class Codes: A61P 5/16 : for decreasing, blocking or antagonising the activity of the thyroid hormones
• CPC Class Codes: A61P 5/46 : for decreasing, blocking or antagonising the activity of glucocorticosteroids
• CPC Class Codes: A61P 5/48 : of the pancreatic hormones
• CPC Class Codes: A61P 9/00 : Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/10 : for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: C07D 211/58 : attached in position 4
• CPC Class Codes: C07D 401/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 401/14 : containing three or more hetero rings
• CPC Class Codes: C07D 405/14 : containing three or more hetero rings
• CPC Class Codes: C07D 409/14 : containing three or more hetero rings
• CPC Class Codes: C07D 417/14 : containing three or more hetero rings

Abstract

A subject of the present application is new derivatives of 4-aminopiperidines of formula

in which R₁, R₂ and R₃ represent various radical, and their preparation processes by synthetic methods in parallel in liquid and solid phase. These products having a good affinity with certain sub-types of somatostatin receptors, they are particularly useful for treating the pathological states or diseases in which one (or more) somatostatin receptors are involved.

Claims

1. Compounds of the general formula:

2. The compound of claim 1, wherein the aryl represented by Z₁₂ is substituted with one or more fluoro, chloro, bromo, iodo, alkyl, alkoxy, alkylthio, —

CF₃, —

OCF₃, phenyl, phenoxy or aminosulphonyl.

3. The compound of claim 1, wherein the aryl represented by Z₂₂ is substituted with one or more fluoro, chloro, bromo, iodo, alkyl, alkenyl, alkoxy, alkylthio, CF₃, OCF₃, nitro, cyano, azido, aminosulphonyl, piperidinosulphonyl, mono- or di-alkylamino, —

C(O)—

O-alkyl, —

C(O)-alkyl, optionally substituted phenyl, phenoxy, phenylthio or benzyloxy.

4. The compound of claim 1, wherein the aryl represented by Z₁₂ is substituted with one or more fluoro, chloro, bromo, iodo, alkyl or alkoxy.

5. The compound of claim 1, wherein the aryl represented by Z₂₂ is substituted with one or more fluoro, chloro, bromo, iodo, alkyl, alkoxy, alkylthio, CF₃, OCF₃, nitro, cyano, azido, piperidinosulphonyl, —

C(O)—

O-alkyl, —

C(O)-alkyl or phenyl.

6. The compound of claim 1, wherein R₃ is unsubstituted alkyl.

7. The compound of claim 1, wherein R₃ is methyl.

8. The compound of claim 1, wherein Z₁₂ and Z₂₂ are optionally substituted phenyl or naphthyl.

9. The compound of claim 1, wherein m and p are simultaneously 1.

10. A pharmaceutical composition comprising a compound of claim 1 or an addition salt thereof with a pharmaceutically acceptable mineral or organic acid.