OA12159A - Monohydrate of cis-lithium-cyano-4-Ä3-(cyclopentyloxy)-4-methoxyphenylÜcyclohexanecar-boxylate. - Google Patents
Monohydrate of cis-lithium-cyano-4-Ä3-(cyclopentyloxy)-4-methoxyphenylÜcyclohexanecar-boxylate. Download PDFInfo
- Publication number
- OA12159A OA12159A OA1200200211A OA1200200211A OA12159A OA 12159 A OA12159 A OA 12159A OA 1200200211 A OA1200200211 A OA 1200200211A OA 1200200211 A OA1200200211 A OA 1200200211A OA 12159 A OA12159 A OA 12159A
- Authority
- OA
- OAPI
- Prior art keywords
- monohydrate
- cyclopentyloxy
- cyano
- lithium
- cis
- Prior art date
Links
- 150000004682 monohydrates Chemical class 0.000 title claims abstract description 21
- CFBUZOUXXHZCFB-UHFFFAOYSA-N 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-cyclohexanecarboxylic acid Chemical compound COC1=CC=C(C2(CCC(CC2)C(O)=O)C#N)C=C1OC1CCCC1 CFBUZOUXXHZCFB-UHFFFAOYSA-N 0.000 claims abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052744 lithium Inorganic materials 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 abstract 1
- 159000000002 lithium salts Chemical class 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 3
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 description 2
- 108010044467 Isoenzymes Proteins 0.000 description 2
- 238000003109 Karl Fischer titration Methods 0.000 description 2
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 2
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 2
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 210000005091 airway smooth muscle Anatomy 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 2
- 210000002865 immune cell Anatomy 0.000 description 2
- 210000004969 inflammatory cell Anatomy 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000005016 nuclear Overhauser enhanced spectroscopy Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- HJHQNXFEOPUDBJ-UHFFFAOYSA-N 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-carboxylic acid;hydrate Chemical compound O.COC1=CC=C(C2(CCC(CC2)C(O)=O)C#N)C=C1OC1CCCC1 HJHQNXFEOPUDBJ-UHFFFAOYSA-N 0.000 description 1
- 101100296719 Caenorhabditis elegans pde-4 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000007883 bronchodilation Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000000451 chemical ionisation Methods 0.000 description 1
- 238000000170 chemical ionisation mass spectrum Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007278 cognition impairment Effects 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 238000005100 correlation spectroscopy Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000000264 spin echo pulse sequence Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P25/28—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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17812900P | 2000-01-26 | 2000-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA12159A true OA12159A (en) | 2006-05-08 |
Family
ID=22651319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200200211A OA12159A (en) | 2000-01-26 | 2001-01-18 | Monohydrate of cis-lithium-cyano-4-Ä3-(cyclopentyloxy)-4-methoxyphenylÜcyclohexanecar-boxylate. |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US6699903B2 (de) |
| EP (1) | EP1250313B1 (de) |
| JP (1) | JP2003520842A (de) |
| KR (1) | KR20020073183A (de) |
| CN (1) | CN1157371C (de) |
| AP (1) | AP1432A (de) |
| AR (1) | AR027273A1 (de) |
| AT (1) | ATE344235T1 (de) |
| AU (1) | AU3282201A (de) |
| BG (1) | BG106959A (de) |
| BR (1) | BR0107709A (de) |
| CA (1) | CA2397758A1 (de) |
| CO (1) | CO5300517A1 (de) |
| CY (1) | CY1108515T1 (de) |
| CZ (1) | CZ20022590A3 (de) |
| DE (1) | DE60124221T2 (de) |
| DK (1) | DK1250313T3 (de) |
| DZ (1) | DZ3285A1 (de) |
| EA (1) | EA200200791A1 (de) |
| EG (1) | EG24065A (de) |
| ES (1) | ES2273804T3 (de) |
| HK (1) | HK1051030A1 (de) |
| HU (1) | HUP0204150A3 (de) |
| IL (1) | IL150400A0 (de) |
| MA (1) | MA25652A1 (de) |
| MX (1) | MXPA02007300A (de) |
| MY (1) | MY122802A (de) |
| NO (1) | NO20023378L (de) |
| NZ (1) | NZ519799A (de) |
| OA (1) | OA12159A (de) |
| PE (1) | PE20011040A1 (de) |
| PL (1) | PL356832A1 (de) |
| PT (1) | PT1250313E (de) |
| SK (1) | SK10942002A3 (de) |
| WO (1) | WO2001055094A1 (de) |
| ZA (1) | ZA200205925B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0011802D0 (en) * | 2000-05-16 | 2000-07-05 | Smithkline Beecham | Method for enhancing cognitive function |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2133439C (en) * | 1992-04-02 | 2005-07-26 | Siegfried Benjamin Christensen, Iv | Compounds useful for treating allergic and inflammatory diseases |
| UA67753C2 (uk) * | 1997-10-10 | 2004-07-15 | Смітклайн Бічам Корпорейшн | Спосіб отримання заміщених 4-феніл-4-ціанциклогексанових кислот |
-
2001
- 2001-01-18 HK HK03101828.3A patent/HK1051030A1/zh unknown
- 2001-01-18 AP APAP/P/2002/002566A patent/AP1432A/en active
- 2001-01-18 ES ES01904886T patent/ES2273804T3/es not_active Expired - Lifetime
- 2001-01-18 MX MXPA02007300A patent/MXPA02007300A/es active IP Right Grant
- 2001-01-18 NZ NZ519799A patent/NZ519799A/en unknown
- 2001-01-18 EP EP01904886A patent/EP1250313B1/de not_active Expired - Lifetime
- 2001-01-18 PT PT01904886T patent/PT1250313E/pt unknown
- 2001-01-18 EA EA200200791A patent/EA200200791A1/ru unknown
- 2001-01-18 KR KR1020027009545A patent/KR20020073183A/ko not_active Ceased
- 2001-01-18 CN CNB018040160A patent/CN1157371C/zh not_active Expired - Fee Related
- 2001-01-18 CZ CZ20022590A patent/CZ20022590A3/cs unknown
- 2001-01-18 US US10/181,865 patent/US6699903B2/en not_active Expired - Fee Related
- 2001-01-18 DZ DZ013285A patent/DZ3285A1/fr active
- 2001-01-18 SK SK1094-2002A patent/SK10942002A3/sk unknown
- 2001-01-18 BR BR0107709-0A patent/BR0107709A/pt not_active IP Right Cessation
- 2001-01-18 DE DE60124221T patent/DE60124221T2/de not_active Expired - Lifetime
- 2001-01-18 OA OA1200200211A patent/OA12159A/en unknown
- 2001-01-18 DK DK01904886T patent/DK1250313T3/da active
- 2001-01-18 AU AU32822/01A patent/AU3282201A/en not_active Abandoned
- 2001-01-18 IL IL15040001A patent/IL150400A0/xx unknown
- 2001-01-18 WO PCT/US2001/001487 patent/WO2001055094A1/en not_active Ceased
- 2001-01-18 PL PL01356832A patent/PL356832A1/xx not_active IP Right Cessation
- 2001-01-18 CA CA002397758A patent/CA2397758A1/en not_active Abandoned
- 2001-01-18 HU HU0204150A patent/HUP0204150A3/hu unknown
- 2001-01-18 JP JP2001555036A patent/JP2003520842A/ja not_active Withdrawn
- 2001-01-18 AT AT01904886T patent/ATE344235T1/de not_active IP Right Cessation
- 2001-01-23 MY MYPI20010322A patent/MY122802A/en unknown
- 2001-01-24 AR ARP010100298A patent/AR027273A1/es unknown
- 2001-01-24 EG EG20010070A patent/EG24065A/xx active
- 2001-01-25 PE PE2001000081A patent/PE20011040A1/es not_active Application Discontinuation
- 2001-01-26 CO CO01005892A patent/CO5300517A1/es not_active Application Discontinuation
-
2002
- 2002-07-12 NO NO20023378A patent/NO20023378L/no not_active Application Discontinuation
- 2002-07-24 MA MA26744A patent/MA25652A1/fr unknown
- 2002-07-24 ZA ZA200205925A patent/ZA200205925B/en unknown
- 2002-07-26 BG BG106959A patent/BG106959A/xx unknown
-
2007
- 2007-01-10 CY CY20071100034T patent/CY1108515T1/el unknown
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