RU2321583C2 - Using derivatives of aniline as phosphodiesterase-4 inhibitors - Google Patents
Using derivatives of aniline as phosphodiesterase-4 inhibitors Download PDFInfo
- Publication number
- RU2321583C2 RU2321583C2 RU2003124303/04A RU2003124303A RU2321583C2 RU 2321583 C2 RU2321583 C2 RU 2321583C2 RU 2003124303/04 A RU2003124303/04 A RU 2003124303/04A RU 2003124303 A RU2003124303 A RU 2003124303A RU 2321583 C2 RU2321583 C2 RU 2321583C2
- Authority
- RU
- Russia
- Prior art keywords
- pyridylmethyl
- diphenylamine
- methoxy
- cyclopentyloxy
- tetrahydrofuryloxy
- Prior art date
Links
Landscapes
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
FIELD: organic chemistry, biochemistry, pharmacy.
SUBSTANCE: invention relates to novel derivatives of aniline of the general formula (I): and their pharmaceutically acceptable salts and isomeric forms possessing properties of phosphodiesterase-4 inhibitors. Compounds can be used, fore example, for enhancing cognitive ability. In compounds of the general formula (I) R1 means linear or branched (C1-C4)-alkyl that can be unsubstituted or substituted with one or more halogen atoms; R2 means linear or branched (C1-C4)-alkyl that can be unsubstituted or substituted with one or more substitutes of the following order: halogen atom, (C1-C4)-alkoxy or their combinations, (C3-C10)-cycloalkyl, (C4-C16)-cycloalkylalkyl wherein alkyl fragment comprises from 1 to 4 carbon atoms, (C7-C11)-arylalkyl wherein aryl fragment comprises 6 carbon atoms, and alkyl fragment that can be linear or branched and comprises from 1 to 5 carbon atoms and wherein radical arylalkyl can be unsubstituted or substituted in aryl fragment with one or more substitutes of the following order: halogen atom, alkoxy group comprising from 1 to 4 carbon atoms or their combinations, and in alkyl fragment one group -CH2CH2- is optionally replaced for group -CH=CH-, and one group -CH2- is optionally replaced for -O- for -NH-, partially unsaturated carbocyclic group comprising from 5 to 9 carbon atoms that can comprise condensed benzene ring, heterocyclic group that can be saturated, partially saturated or unsaturated and comprises from 5 to 6 carbon atoms in cycle including one atom chosen from oxygen (O), or heterocyclylalkyl group wherein heterocyclic fragment can be saturated, partially saturated or unsaturated and comprises from 5 to 6 carbon atoms in cycle including 1-2 atoms chosen from nitrogen (N) or sulfur (S) atoms, and alkyl fragment that can be linear or branched comprises from 1 to 5 carbon atoms; R3 means partially unsaturated carbocyclylalkyl group wherein carbocyclic fragment comprises from 5 to 6 carbon atoms, and linear or branched alkyl fragment comprises from 1 to 5 carbon atoms, (C7-C11)-arylalkyl wherein aryl fragment comprises 6 carbon atoms, and linear or branched alkyl fragment comprises from 1 to 5 carbon atoms and wherein arylalkyl radical can be linear or substituted in aryl fragment with one or more substitutes of the following group: trifluoromethyl, (C1-C4)-alkyl, (C1-C4)-alkoxy or their combinations, heterocyclylalkyl group wherein heterocyclic fragment can be aromatic, partially or completely saturated and comprises from 5 to 10 atoms in cycle including 1-2 atoms chosen from N, O or S, and linear or branched alkyl fragment comprises from 1 to 5 carbon atoms and wherein heterocyclylalkyl group can be linear or substituted in heterocyclic fragment with one or more substitutes of the following order: halogen atom, (C1-C4)-alkyl, (C1-C4)-alkoxy or their combinations; R4 means (C6-C12)-aryl that can be linear or substituted with one or more substitutes of the following order: halogen atom, (C1-C4)-alkyl, (C2-C4)-alkenyl, hydroxy, (C1-C4)-alkoxy, (C2-C4)-alkoxyalkoxy, nitro, trifluoromethyl, -OCF3, amino group, aminoalkyl, aminoalkoxy, hydroxy-(C1-C4)-alkyl, hydroxamic acid, tetrazol-5-yl, 2-(heterocyclyl)-tetrazol-5-yl, carboxy, alkoxycarbonyl, cyano, acyl, alkylsulfonyl, phenoxy, trialkyloxy, R5-L or their combinations, or heteroaryl comprising from 5 to 10 atoms in cycle including 1-2 atoms chosen from N wherein heteroaryl can be linear or substituted with one or more substitutes of the following order: (C1-C4)-alkyl, (C1-C4)-alkoxy, carboxy, alkoxycarbonyl or their combinations; R5 means hydrogen atom, (C1-C8)-alkyl, (C3-C10)-cycloalkyl, C6-aryl, heterocyclic group that can be saturated, partially saturated or unsaturated and comprises from 5 to 10 atoms in cycle from which at least atom means N or O, and wherein heterocyclic group can be linear or substituted with one or more (C1-C4)-alkyls, or group heterocyclylalkyl, and others. Also, invention relates to intermediates compounds and to a method for enhancing the cognitive ability.
EFFECT: valuable biological and biochemical property of compounds.
49 cl, 8 sch, 26 ex
Description
Claims (49)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26265101P | 2001-01-22 | 2001-01-22 | |
| US60/262,651 | 2001-01-22 | ||
| US26719601P | 2001-02-08 | 2001-02-08 | |
| US60/267,196 | 2001-02-08 | ||
| US60/306,140 | 2001-07-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2003124303A RU2003124303A (en) | 2005-03-10 |
| RU2321583C2 true RU2321583C2 (en) | 2008-04-10 |
Family
ID=35364132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003124303/04A RU2321583C2 (en) | 2001-01-22 | 2002-01-22 | Using derivatives of aniline as phosphodiesterase-4 inhibitors |
Country Status (1)
| Country | Link |
|---|---|
| RU (1) | RU2321583C2 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5591776A (en) * | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
| RU2124009C1 (en) * | 1992-01-21 | 1998-12-27 | Глаксо С.П.А. | Derivatives of 1,5-benzodiazepine, method of their synthesis, pharmaceutical composition |
-
2002
- 2002-01-22 RU RU2003124303/04A patent/RU2321583C2/en not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2124009C1 (en) * | 1992-01-21 | 1998-12-27 | Глаксо С.П.А. | Derivatives of 1,5-benzodiazepine, method of their synthesis, pharmaceutical composition |
| US5591776A (en) * | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
Non-Patent Citations (2)
| Title |
|---|
| HELMAN WILLIAM P. et al. "Synthesis and antiinflammatory evaluation of subsstituted isophtalonitriles and trimesonitriles, benzonitriles and terephtalonitriles". J. of Medical Chemistry, 1978, v.21, No.9, p 906-913. WATANABE T. et al. "Stracture-activity Relationship at Rational Design of 3,4-Dephostatin Derivatives as Protein Tirosine Phosphatase Inhibitors" TETRAHEDRON, 01.2000, v.56, no.5, p.741-752. * |
| INOUE ISAO et al. "Steric tuning in chiral ligand mediated enantioselective alkylation of imines" TETRAHEDRON ASYMMETRY, 1993, v.4, no.7, p.1603-1606. * |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2003124303A (en) | 2005-03-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2326869C2 (en) | Pyridazine 3(2h) derivatives as inhibitor of phosphodiesterase 4 (pde4), method of their preparation, pharmaceutical composition and method of treatment | |
| NL192454C (en) | N, N'-disubstituted urea, thiourea, guanidine and diaminoethylene derivatives, process for their preparation and pharmaceutical preparations containing these derivatives. | |
| JP3845792B2 (en) | Ω-Carboxyaryl-substituted diphenylureas as RAF kinase inhibitors | |
| RU2489148C2 (en) | Stat3/5 activation inhibitor | |
| EP0661266A1 (en) | Substituted cyclic amine compounds as 5HT2 antagonists | |
| JP2019533694A5 (en) | ||
| RU2005136368A (en) | PIPERASIN DERIVATIVES AND THEIR APPLICATION FOR TREATMENT OF NEUROLOGICAL AND PSYCHIATRIC DISEASES | |
| JP2756975B2 (en) | Pyridinium derivatives | |
| US20030181442A1 (en) | omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors | |
| KR880009933A (en) | Acyl-CoA: saturated fatty acid amides as cholesterol acyltransferase inhibitors | |
| EP1562916A1 (en) | Methods for preparing n-arylated oxazolidinones via a copper catalyzed cross coupling reaction | |
| RU2005119627A (en) | PHOSPHODESTHESIS INHIBITORS 4 | |
| JP2016534134A5 (en) | ||
| RU2219179C2 (en) | Azacyclic compounds, pharmaceutical compositions | |
| EA022875B1 (en) | 4-(indazole-5-ylamino)-2-phenylquinazolin derivatives | |
| BRPI0808737A2 (en) | MALONAMIDES AS OREXIN ANTAGONISTS. | |
| US20020019527A1 (en) | Substituted phenyl farnesyltransferase inhibitors | |
| RU2321583C2 (en) | Using derivatives of aniline as phosphodiesterase-4 inhibitors | |
| CA2407093A1 (en) | Substituted phenyl farnesyltransferase inhibitors | |
| RU2203891C2 (en) | Antiviral pyrimidinedione derivatives, method of their synthesis and pharmaceutical composition based on thereof | |
| KR940003912A (en) | Ferroelectric liquid crystals having cyclohexenyl cores and compositions comprising them | |
| US5728835A (en) | Substituted cyclic amine compound, production process thereof and pharmaceutical composition for circulatory organ use containing the same | |
| JP2009514899A5 (en) | ||
| JP7132849B2 (en) | Thiazolidinone compound and use thereof | |
| Colapret et al. | Synthesis and pharmacological evaluation of 4, 4-disubstituted piperidines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20120123 |