UA80580C2 - Phenylnaphtaline derivatives, method of their obtaining and pharmaceutical composition that comprises them - Google Patents
Phenylnaphtaline derivatives, method of their obtaining and pharmaceutical composition that comprises them Download PDFInfo
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- UA80580C2 UA80580C2 UAA200505385A UA2005005385A UA80580C2 UA 80580 C2 UA80580 C2 UA 80580C2 UA A200505385 A UAA200505385 A UA A200505385A UA 2005005385 A UA2005005385 A UA 2005005385A UA 80580 C2 UA80580 C2 UA 80580C2
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- 238000000034 method Methods 0.000 title claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 141
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000000654 additive Substances 0.000 claims description 15
- 230000000996 additive effect Effects 0.000 claims description 15
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 14
- 230000001193 melatoninergic effect Effects 0.000 claims description 11
- 230000009471 action Effects 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 230000007170 pathology Effects 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
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- -1 3--(aminomethyl)phenyl Chemical group 0.000 claims description 5
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
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- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 claims description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 3
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- 125000003342 alkenyl group Chemical group 0.000 claims description 2
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- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
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- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 claims 1
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- 230000002490 cerebral effect Effects 0.000 claims 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 238000004452 microanalysis Methods 0.000 description 12
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
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- DGUWACLYDSWXRZ-UHFFFAOYSA-N (2-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C=O DGUWACLYDSWXRZ-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/60—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
Landscapes
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hematology (AREA)
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- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
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- Immunology (AREA)
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- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0213917A FR2846963B1 (fr) | 2002-11-07 | 2002-11-07 | Nouveaux derives du phenylnaphtalene, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PCT/FR2003/003278 WO2004043907A1 (fr) | 2002-11-07 | 2003-11-04 | Nouveaux derives du phenylnaphtalene, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA80580C2 true UA80580C2 (en) | 2007-10-10 |
Family
ID=32116435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200505385A UA80580C2 (en) | 2002-11-07 | 2003-04-11 | Phenylnaphtaline derivatives, method of their obtaining and pharmaceutical composition that comprises them |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20060106111A1 (ru) |
| EP (1) | EP1558566A1 (ru) |
| JP (1) | JP2006505604A (ru) |
| KR (1) | KR100682702B1 (ru) |
| CN (1) | CN1324004C (ru) |
| AR (1) | AR042004A1 (ru) |
| AU (1) | AU2003292324A1 (ru) |
| BR (1) | BR0316095A (ru) |
| CA (1) | CA2503992A1 (ru) |
| EA (1) | EA008250B1 (ru) |
| FR (1) | FR2846963B1 (ru) |
| GE (1) | GEP20074181B (ru) |
| HK (1) | HK1081944A1 (ru) |
| MA (1) | MA27409A1 (ru) |
| MX (1) | MXPA05004910A (ru) |
| NO (1) | NO20052757L (ru) |
| NZ (1) | NZ539631A (ru) |
| PL (1) | PL376251A1 (ru) |
| UA (1) | UA80580C2 (ru) |
| WO (1) | WO2004043907A1 (ru) |
| ZA (1) | ZA200503232B (ru) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2771739B1 (fr) * | 1997-11-28 | 2001-04-20 | Adir | Nouveaux composes naphtaleniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
2002
- 2002-11-07 FR FR0213917A patent/FR2846963B1/fr not_active Expired - Fee Related
-
2003
- 2003-04-11 UA UAA200505385A patent/UA80580C2/uk unknown
- 2003-11-04 AU AU2003292324A patent/AU2003292324A1/en not_active Abandoned
- 2003-11-04 BR BR0316095-5A patent/BR0316095A/pt not_active IP Right Cessation
- 2003-11-04 KR KR1020057008141A patent/KR100682702B1/ko not_active IP Right Cessation
- 2003-11-04 MX MXPA05004910A patent/MXPA05004910A/es not_active Application Discontinuation
- 2003-11-04 CA CA002503992A patent/CA2503992A1/fr not_active Abandoned
- 2003-11-04 PL PL03376251A patent/PL376251A1/xx not_active Application Discontinuation
- 2003-11-04 NZ NZ539631A patent/NZ539631A/en unknown
- 2003-11-04 JP JP2004550730A patent/JP2006505604A/ja active Pending
- 2003-11-04 GE GEAP20038835A patent/GEP20074181B/en unknown
- 2003-11-04 EP EP03767890A patent/EP1558566A1/fr not_active Withdrawn
- 2003-11-04 US US10/534,116 patent/US20060106111A1/en not_active Abandoned
- 2003-11-04 CN CNB2003801027158A patent/CN1324004C/zh not_active Expired - Fee Related
- 2003-11-04 WO PCT/FR2003/003278 patent/WO2004043907A1/fr active Application Filing
- 2003-11-04 EA EA200500720A patent/EA008250B1/ru not_active IP Right Cessation
- 2003-11-07 AR ARP030104102A patent/AR042004A1/es not_active Application Discontinuation
-
2005
- 2005-04-19 MA MA28231A patent/MA27409A1/fr unknown
- 2005-04-21 ZA ZA200503232A patent/ZA200503232B/en unknown
- 2005-06-07 NO NO20052757A patent/NO20052757L/no not_active Application Discontinuation
-
2006
- 2006-02-22 HK HK06102325A patent/HK1081944A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA05004910A (es) | 2005-07-22 |
| GEP20074181B (en) | 2007-08-10 |
| AU2003292324A1 (en) | 2004-06-03 |
| CN1324004C (zh) | 2007-07-04 |
| NZ539631A (en) | 2006-10-27 |
| CA2503992A1 (fr) | 2004-05-27 |
| MA27409A1 (fr) | 2005-06-01 |
| ZA200503232B (en) | 2006-06-28 |
| PL376251A1 (en) | 2005-12-27 |
| EA008250B1 (ru) | 2007-04-27 |
| AR042004A1 (es) | 2005-06-08 |
| KR20050074553A (ko) | 2005-07-18 |
| JP2006505604A (ja) | 2006-02-16 |
| FR2846963A1 (fr) | 2004-05-14 |
| BR0316095A (pt) | 2005-09-27 |
| CN1711235A (zh) | 2005-12-21 |
| EP1558566A1 (fr) | 2005-08-03 |
| FR2846963B1 (fr) | 2006-07-14 |
| HK1081944A1 (en) | 2006-05-26 |
| NO20052757D0 (no) | 2005-06-07 |
| WO2004043907A1 (fr) | 2004-05-27 |
| NO20052757L (no) | 2005-06-07 |
| KR100682702B1 (ko) | 2007-02-15 |
| US20060106111A1 (en) | 2006-05-18 |
| EA200500720A1 (ru) | 2005-10-27 |
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