HRP20120680T1 - Spojevi 1,5-difenilpirolidin-2-ona kao ligandi cb-1 - Google Patents
Spojevi 1,5-difenilpirolidin-2-ona kao ligandi cb-1 Download PDFInfo
- Publication number
- HRP20120680T1 HRP20120680T1 HRP20120680AT HRP20120680T HRP20120680T1 HR P20120680 T1 HRP20120680 T1 HR P20120680T1 HR P20120680A T HRP20120680A T HR P20120680AT HR P20120680 T HRP20120680 T HR P20120680T HR P20120680 T1 HRP20120680 T1 HR P20120680T1
- Authority
- HR
- Croatia
- Prior art keywords
- pharmaceutically acceptable
- acceptable salt
- compound according
- hydrogen
- schizophrenia
- Prior art date
Links
- RNVOXAHWAAVDBN-UHFFFAOYSA-N 1,5-diphenylpyrrolidin-2-one Chemical class O=C1CCC(C=2C=CC=CC=2)N1C1=CC=CC=C1 RNVOXAHWAAVDBN-UHFFFAOYSA-N 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 150000002431 hydrogen Chemical group 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 201000000980 schizophrenia Diseases 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
- 230000000561 anti-psychotic effect Effects 0.000 claims 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- -1 trifluoromethoxy, difluoromethoxy Chemical group 0.000 claims 3
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Chemical group 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 230000004584 weight gain Effects 0.000 claims 2
- 235000019786 weight gain Nutrition 0.000 claims 2
- CWWOXXZNNMASMF-FGZHOGPDSA-N (3r,5r)-3-[2-(2-cyclopropylpyrimidin-4-yl)propan-2-ylamino]-5-[3-(trifluoromethoxy)phenyl]-1-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound N1([C@H](C[C@H](C1=O)NC(C)(C)C=1N=C(N=CC=1)C1CC1)C=1C=C(OC(F)(F)F)C=CC=1)C1=CC=C(C(F)(F)F)C=C1 CWWOXXZNNMASMF-FGZHOGPDSA-N 0.000 claims 1
- QFXONEUOPFUQOW-RTBURBONSA-N (3r,5r)-5-(3-fluorophenyl)-1-[4-(trifluoromethoxy)phenyl]-3-[2-[2-(trifluoromethyl)pyrimidin-4-yl]propan-2-ylamino]pyrrolidin-2-one Chemical compound N1([C@H](C[C@H](C1=O)NC(C)(C)C=1N=C(N=CC=1)C(F)(F)F)C=1C=C(F)C=CC=1)C1=CC=C(OC(F)(F)F)C=C1 QFXONEUOPFUQOW-RTBURBONSA-N 0.000 claims 1
- JSWJUOYDUXZARF-RTBURBONSA-N (3r,5r)-5-[3-(trifluoromethoxy)phenyl]-1-[4-(trifluoromethyl)phenyl]-3-[2-[2-(trifluoromethyl)pyrimidin-4-yl]propan-2-ylamino]pyrrolidin-2-one Chemical compound N1([C@H](C[C@H](C1=O)NC(C)(C)C=1N=C(N=CC=1)C(F)(F)F)C=1C=C(OC(F)(F)F)C=CC=1)C1=CC=C(C(F)(F)F)C=C1 JSWJUOYDUXZARF-RTBURBONSA-N 0.000 claims 1
- RCFUKOGURDPHPE-WOJBJXKFSA-N (3r,5r)-5-phenyl-1-[4-(trifluoromethoxy)phenyl]-3-[2-[6-(trifluoromethyl)pyridin-2-yl]propan-2-ylamino]pyrrolidin-2-one Chemical compound N1([C@H](C[C@H](C1=O)NC(C)(C)C=1N=C(C=CC=1)C(F)(F)F)C=1C=CC=CC=1)C1=CC=C(OC(F)(F)F)C=C1 RCFUKOGURDPHPE-WOJBJXKFSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000021017 Weight Gain Diseases 0.000 claims 1
- 201000007930 alcohol dependence Diseases 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 230000037406 food intake Effects 0.000 claims 1
- 235000012631 food intake Nutrition 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000005586 smoking cessation Effects 0.000 claims 1
- 201000009032 substance abuse Diseases 0.000 claims 1
- 231100000736 substance abuse Toxicity 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (14)
1. Spoj formule
[image]
naznačen time što
R1 se bira iz skupine koju čine vodik, klor, cijano, trifluormetil, difluormetoksi, te trifluormetoksi;
R2 se bira iz skupine koju čine vodik, halogen, cijano, (C1-C3) alkil, supstituiran s 1 do 5 fluornih skupina, te (C1-C3) alkoksi, supstituiran s 1 do 5 fluornih skupina;
R3 se bira iz skupine koju čine vodik, fluor, te klor;
R4 se bira iz skupine koju čine trifluormetil, cijano i ciklopropil;
uz uvjet da, kada je R1 vodik, klor, cijano ili trifluormetil, R2 je (C1-C3) alkoksi, supstituiran s 1 do 5 fluornih skupina;
ili njegove farmaceutski prihvatljive soli.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R2 se bira iz skupine koju čine vodik, fluor, klor, cijano, trifluormetil, 1,1-difluoretil, trifluormetoksi, difluormetoksi, te 1,1,2,2-tetrafluoretoksi, ili njegova farmaceutski prihvatljiva sol.
3. Spoj u skladu s patentnim zahtjevom 2, naznačen time što R2 se bira iz skupine koju čine trifluormetil, 1,1-difluoretil, difluormetoksi, trifluormetoksi, te 1,1,2,2-tetrafluoretoksi, a R3 je vodik, ili njegova farmaceutski prihvatljiva sol.
4. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što R1 je difluormetoksi ili trifluormetoksi, ili njegova farmaceutski prihvatljiva sol.
5. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R2 je (C1-C3) alkoksi, supstituiran s 1 do 5 fluornih skupina, ili njegova farmaceutski prihvatljiva sol.
6. Spoj u skladu s patentnim zahtjevom 5, naznačen time što R3 je vodik, ili njegova farmaceutski prihvatljiva sol.
7. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je (3R,5R)-3-[1-metil-1-(2-trifluormetilpirimidin-4-il)etilamino]-5-(3-trifluormetoksifenil)-1-(4-trifluormetilfenil)pirolidin-2-on, ili njegova farmaceutski prihvatljiva sol.
8. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je (3R,5R)-3-[1-(2-ciklopropilpirimidin-4-il)-1-metiletilamino]-5-(3-trifluormetoksifenil)-1-(4-trifluormetilfenil)pirolidin-2-on, ili njegova farmaceutski prihvatljiva sol.
9. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je (3R,5R)-3-[1-metil-1-(2-trifluormetilpirimidin-4-il)etilamino]-5-(3-fluorfenil)-1-(4-trifluormetoksifenil)pirolidin-2-on, ili njegova farmaceutski prihvatljiva sol.
10. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je (3R,5R)-3-[1-metil-1-(6-trifluormetilpiridin-2-il)etilamino]-5fenil-1-(4-trifluormetoksifenil)pirolidin-2-on, ili njegova farmaceutski prihvatljiva sol.
11. Farmaceutski pripravak, naznačen time što sasrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 10, ili njegovu farmaceutski prihvatljivu sol, i farmaceutski prihvatljivu podlogu, razrjeđivač ili pomoćnu tvar.
12. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u terapiji.
13. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u liječenju poremećaja kojeg se bira između: poremećaja hranjenja povezanog s prekomjernim unosom hrane, pretilosti, shizofrenije, kognitivnog poremećaja povezanog sa shizofrenijom, negativnih simptoma povezanih sa shizofrenijom, zloupotrebe tvari, ovisnosti o alkoholu, te dobitka na težini povezanog s liječenjem antipsihotikom, ili u liječenju radi prekida pušenja.
14. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u istodobnoj, odvojenoj ili uzastopnoj kombinaciji s antipsihotikom u liječenju poremećaja kojeg se bira između: shizofrenije, kognitivnog poremećaja povezanog sa shizofrenijom, negativnih simptoma povezanih sa shizofrenijom, te dobitka na težini povezanog s liječenjem antipsihotikom.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4694308P | 2008-04-22 | 2008-04-22 | |
| PCT/US2009/039293 WO2009131815A1 (en) | 2008-04-22 | 2009-04-02 | 1,5-diphenyl-pyrrolidin-2-one compounds as cb-1 ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20120680T1 true HRP20120680T1 (hr) | 2012-10-31 |
Family
ID=40600096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20120680AT HRP20120680T1 (hr) | 2008-04-22 | 2012-08-24 | Spojevi 1,5-difenilpirolidin-2-ona kao ligandi cb-1 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US8420654B2 (hr) |
| EP (1) | EP2280961B1 (hr) |
| JP (1) | JP5539323B2 (hr) |
| KR (1) | KR101283803B1 (hr) |
| CN (1) | CN102007121B (hr) |
| AU (1) | AU2009238445B2 (hr) |
| BR (1) | BRPI0910775A2 (hr) |
| CA (1) | CA2721542C (hr) |
| DK (1) | DK2280961T3 (hr) |
| EA (1) | EA019067B1 (hr) |
| ES (1) | ES2390560T3 (hr) |
| HR (1) | HRP20120680T1 (hr) |
| MX (1) | MX2010011547A (hr) |
| PL (1) | PL2280961T3 (hr) |
| PT (1) | PT2280961E (hr) |
| SI (1) | SI2280961T1 (hr) |
| WO (1) | WO2009131815A1 (hr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10154988B2 (en) | 2012-11-14 | 2018-12-18 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1496838B1 (en) * | 2002-03-12 | 2010-11-03 | Merck Sharp & Dohme Corp. | Substituted amides |
| TW200533657A (en) | 2004-02-17 | 2005-10-16 | Esteve Labor Dr | Substituted pyrazoline compounds, their preparation and use as medicaments |
| AU2005214084B2 (en) | 2004-02-19 | 2010-06-03 | Solvay Pharmaceuticals B.V. | Imidazoline derivatives having CB1-antagonistic activity |
| WO2007020502A2 (en) * | 2005-08-16 | 2007-02-22 | Pharmacia & Upjohn Company Llc | Cannabinoid receptor ligands and uses thereof |
| EP2097410A4 (en) * | 2006-09-29 | 2009-11-25 | Green Cross Corp | HETEROYL-PYRAZOLE DERIVATIVES AS CANNABINOID CB1 RECEPTOR ANTAGONISTS |
| PE20080926A1 (es) | 2006-10-23 | 2008-07-19 | Lilly Co Eli | Compuestos cb1 |
-
2009
- 2009-04-02 SI SI200930349T patent/SI2280961T1/sl unknown
- 2009-04-02 MX MX2010011547A patent/MX2010011547A/es active IP Right Grant
- 2009-04-02 EA EA201071223A patent/EA019067B1/ru not_active IP Right Cessation
- 2009-04-02 CN CN2009801137973A patent/CN102007121B/zh not_active Expired - Fee Related
- 2009-04-02 CA CA2721542A patent/CA2721542C/en not_active Expired - Fee Related
- 2009-04-02 DK DK09734415.4T patent/DK2280961T3/da active
- 2009-04-02 PT PT09734415T patent/PT2280961E/pt unknown
- 2009-04-02 PL PL09734415T patent/PL2280961T3/pl unknown
- 2009-04-02 EP EP09734415A patent/EP2280961B1/en not_active Not-in-force
- 2009-04-02 KR KR1020107023546A patent/KR101283803B1/ko not_active IP Right Cessation
- 2009-04-02 AU AU2009238445A patent/AU2009238445B2/en not_active Ceased
- 2009-04-02 BR BRPI0910775A patent/BRPI0910775A2/pt not_active IP Right Cessation
- 2009-04-02 ES ES09734415T patent/ES2390560T3/es active Active
- 2009-04-02 WO PCT/US2009/039293 patent/WO2009131815A1/en active Application Filing
- 2009-04-02 US US12/935,596 patent/US8420654B2/en not_active Expired - Fee Related
- 2009-04-02 JP JP2011506339A patent/JP5539323B2/ja not_active Expired - Fee Related
-
2012
- 2012-08-24 HR HRP20120680AT patent/HRP20120680T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL2280961T3 (pl) | 2012-12-31 |
| ES2390560T3 (es) | 2012-11-14 |
| EP2280961A1 (en) | 2011-02-09 |
| KR101283803B1 (ko) | 2013-07-15 |
| US8420654B2 (en) | 2013-04-16 |
| PT2280961E (pt) | 2012-09-10 |
| EA019067B1 (ru) | 2013-12-30 |
| EP2280961B1 (en) | 2012-07-25 |
| CA2721542C (en) | 2016-03-29 |
| MX2010011547A (es) | 2010-11-09 |
| US20110034484A1 (en) | 2011-02-10 |
| CN102007121A (zh) | 2011-04-06 |
| AU2009238445B2 (en) | 2013-09-26 |
| BRPI0910775A2 (pt) | 2015-09-29 |
| WO2009131815A1 (en) | 2009-10-29 |
| AU2009238445A1 (en) | 2009-10-29 |
| DK2280961T3 (da) | 2012-08-27 |
| SI2280961T1 (sl) | 2012-11-30 |
| CA2721542A1 (en) | 2009-10-29 |
| EA201071223A1 (ru) | 2011-04-29 |
| JP5539323B2 (ja) | 2014-07-02 |
| KR20100124342A (ko) | 2010-11-26 |
| CN102007121B (zh) | 2013-08-14 |
| JP2011518220A (ja) | 2011-06-23 |
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