JP2009514935A - 新規化合物 - Google Patents
新規化合物 Download PDFInfo
- Publication number
- JP2009514935A JP2009514935A JP2008539486A JP2008539486A JP2009514935A JP 2009514935 A JP2009514935 A JP 2009514935A JP 2008539486 A JP2008539486 A JP 2008539486A JP 2008539486 A JP2008539486 A JP 2008539486A JP 2009514935 A JP2009514935 A JP 2009514935A
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- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- halogen
- chloro
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 180
- 238000000034 method Methods 0.000 claims abstract description 47
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 22
- LUMNUWCAKQABAN-HNNXBMFYSA-N 2-[4-chloro-2-[[(3s)-3-methyl-4-[2-[4-(trifluoromethyl)phenyl]acetyl]piperazin-1-yl]methyl]phenyl]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC(=CC=2)C(F)(F)F)C)N1CC1=CC(Cl)=CC=C1CC(O)=O LUMNUWCAKQABAN-HNNXBMFYSA-N 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 206010039083 rhinitis Diseases 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- UTYMAGFCZOUQSX-HNNXBMFYSA-N 2-[4-chloro-2-[[(3s)-4-[2-(4-chlorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenyl]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC(Cl)=CC=2)C)N1CC1=CC(Cl)=CC=C1CC(O)=O UTYMAGFCZOUQSX-HNNXBMFYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- UQSMOPIWDZNJIU-HNNXBMFYSA-N 2-[2-[[(3s)-4-(benzenesulfonyl)-3-methylpiperazin-1-yl]methyl]-4-chlorophenyl]acetic acid Chemical compound C([C@@H](N(CC1)S(=O)(=O)C=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1CC(O)=O UQSMOPIWDZNJIU-HNNXBMFYSA-N 0.000 claims description 4
- BSQPWXDFWOQXPT-INIZCTEOSA-N 2-[2-[[(3s)-4-(benzenesulfonyl)-3-methylpiperazin-1-yl]methyl]phenyl]acetic acid Chemical compound C([C@@H](N(CC1)S(=O)(=O)C=2C=CC=CC=2)C)N1CC1=CC=CC=C1CC(O)=O BSQPWXDFWOQXPT-INIZCTEOSA-N 0.000 claims description 4
- QCWAQTCTFGKCQB-NRFANRHFSA-N 2-[4-chloro-2-[[(3s)-3-ethyl-4-[2-(4-fluorophenyl)acetyl]piperazin-1-yl]methyl]phenyl]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC(F)=CC=2)CC)N1CC1=CC(Cl)=CC=C1CC(O)=O QCWAQTCTFGKCQB-NRFANRHFSA-N 0.000 claims description 4
- LYJRGILVYHUCGI-INIZCTEOSA-N 2-[4-chloro-2-[[(3s)-3-methyl-4-(2-phenylacetyl)piperazin-1-yl]methyl]phenyl]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1CC(O)=O LYJRGILVYHUCGI-INIZCTEOSA-N 0.000 claims description 4
- FLDFHEAHYYMRFS-HNNXBMFYSA-N 2-[4-chloro-2-[[(3s)-4-[2-(4-fluorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenyl]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC(F)=CC=2)C)N1CC1=CC(Cl)=CC=C1CC(O)=O FLDFHEAHYYMRFS-HNNXBMFYSA-N 0.000 claims description 4
- RUZGXZVFSBVXET-KRWDZBQOSA-N 3-[2-[[(3s)-4-benzylsulfonyl-3-methylpiperazin-1-yl]methyl]-4-chlorophenyl]propanoic acid Chemical compound C([C@@H](N(CC1)S(=O)(=O)CC=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1CCC(O)=O RUZGXZVFSBVXET-KRWDZBQOSA-N 0.000 claims description 4
- MFELOIQWSKQMLV-KRWDZBQOSA-N 3-[4-chloro-2-[[(3s)-3-methyl-4-(2-phenylacetyl)piperazin-1-yl]methyl]phenyl]propanoic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1CCC(O)=O MFELOIQWSKQMLV-KRWDZBQOSA-N 0.000 claims description 4
- KLOCOODWXMELPK-SFHVURJKSA-N 3-[4-chloro-2-[[(3s)-3-methyl-4-[(2-methylphenyl)methylsulfonyl]piperazin-1-yl]methyl]phenyl]propanoic acid Chemical compound C([C@@H](N(CC1)S(=O)(=O)CC=2C(=CC=CC=2)C)C)N1CC1=CC(Cl)=CC=C1CCC(O)=O KLOCOODWXMELPK-SFHVURJKSA-N 0.000 claims description 4
- DIJMEEUBAXTPDQ-SFHVURJKSA-N 3-[4-chloro-2-[[(3s)-3-methyl-4-[(3-methylphenyl)methylsulfonyl]piperazin-1-yl]methyl]phenyl]propanoic acid Chemical compound C([C@@H](N(CC1)S(=O)(=O)CC=2C=C(C)C=CC=2)C)N1CC1=CC(Cl)=CC=C1CCC(O)=O DIJMEEUBAXTPDQ-SFHVURJKSA-N 0.000 claims description 4
- IGHAJKQBKIBBBB-SFHVURJKSA-N 3-[4-chloro-2-[[(3s)-3-methyl-4-[(4-methylphenyl)methylsulfonyl]piperazin-1-yl]methyl]phenyl]propanoic acid Chemical compound C([C@@H](N(CC1)S(=O)(=O)CC=2C=CC(C)=CC=2)C)N1CC1=CC(Cl)=CC=C1CCC(O)=O IGHAJKQBKIBBBB-SFHVURJKSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- IGJUZAULTLOTPT-KRWDZBQOSA-N 2-[2-[[(3s)-4-benzylsulfonyl-3-methylpiperazin-1-yl]methyl]-4-chlorophenyl]-n-methylsulfonylacetamide Chemical compound C([C@@H](N(CC1)S(=O)(=O)CC=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1CC(=O)NS(C)(=O)=O IGJUZAULTLOTPT-KRWDZBQOSA-N 0.000 claims description 3
- USELGMAYVJTSGV-INIZCTEOSA-N 2-[2-[[(3s)-4-benzylsulfonyl-3-methylpiperazin-1-yl]methyl]-4-chlorophenyl]acetic acid Chemical compound C([C@@H](N(CC1)S(=O)(=O)CC=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1CC(O)=O USELGMAYVJTSGV-INIZCTEOSA-N 0.000 claims description 3
- FCIDWUPHZWWUHV-AWEZNQCLSA-N 2-[4-chloro-2-[[(3s)-4-[2-(2,4-difluorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenyl]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C(=CC(F)=CC=2)F)C)N1CC1=CC(Cl)=CC=C1CC(O)=O FCIDWUPHZWWUHV-AWEZNQCLSA-N 0.000 claims description 3
- GKADYJRRPXUNEA-AWEZNQCLSA-N 2-[4-chloro-2-[[(3s)-4-[2-(3,4-difluorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenyl]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=C(F)C(F)=CC=2)C)N1CC1=CC(Cl)=CC=C1CC(O)=O GKADYJRRPXUNEA-AWEZNQCLSA-N 0.000 claims description 3
- MUOQDHGLUUXEJF-NRFANRHFSA-N 2-[4-chloro-2-[[(3s)-4-[2-(4-chlorophenyl)acetyl]-3-ethylpiperazin-1-yl]methyl]phenyl]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC(Cl)=CC=2)CC)N1CC1=CC(Cl)=CC=C1CC(O)=O MUOQDHGLUUXEJF-NRFANRHFSA-N 0.000 claims description 3
- PELIOUPRRPCUJI-INIZCTEOSA-N 2-[4-chloro-2-[[(3s)-4-[2-(4-methoxyphenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenyl]acetic acid Chemical compound C1=CC(OC)=CC=C1CC(=O)N1[C@@H](C)CN(CC=2C(=CC=C(Cl)C=2)CC(O)=O)CC1 PELIOUPRRPCUJI-INIZCTEOSA-N 0.000 claims description 3
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 claims description 3
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 claims description 3
- QLVSHOLNMDOUQW-UHFFFAOYSA-M sodium;3-[2-[(4-benzylsulfonylpiperazin-1-yl)methyl]-4-chlorophenyl]propanoate Chemical compound [Na+].[O-]C(=O)CCC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)CC=2C=CC=CC=2)CC1 QLVSHOLNMDOUQW-UHFFFAOYSA-M 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims 1
- 150000003180 prostaglandins Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 6
- 125000003107 substituted aryl group Chemical group 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 91
- 239000000047 product Substances 0.000 description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 238000005481 NMR spectroscopy Methods 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
- 230000002829 reductive effect Effects 0.000 description 50
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 238000001819 mass spectrum Methods 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000003112 inhibitor Substances 0.000 description 27
- -1 4H-quinolidine Chemical compound 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 235000019439 ethyl acetate Nutrition 0.000 description 25
- 239000000203 mixture Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
- 239000000377 silicon dioxide Substances 0.000 description 20
- 238000004587 chromatography analysis Methods 0.000 description 19
- 239000003480 eluent Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
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- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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| GB0607353A GB0607353D0 (en) | 2006-04-12 | 2006-04-12 | Novel Compounds |
| PCT/GB2006/004075 WO2007052023A2 (en) | 2005-11-05 | 2006-11-01 | Novel compounds |
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| JP2009514935A true JP2009514935A (ja) | 2009-04-09 |
| JP2009514935A5 JP2009514935A5 (enExample) | 2009-10-22 |
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| EP (1) | EP1948630A2 (enExample) |
| JP (1) | JP2009514935A (enExample) |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020500178A (ja) * | 2016-11-16 | 2020-01-09 | ルンドベック ラ ホーヤ リサーチ センター,インク. | Magl阻害剤 |
| JP2020504707A (ja) * | 2016-11-16 | 2020-02-13 | ルンドベック ラ ホーヤ リサーチ センター,インク. | Magl阻害剤 |
| US11332453B2 (en) | 2018-05-15 | 2022-05-17 | H. Lundbeck A/S | MAGL inhibitors |
| US11530189B2 (en) | 2012-01-06 | 2022-12-20 | H. Lundbecka/S | Carbamate compounds and methods of making and using same |
| US12378219B2 (en) | 2022-05-04 | 2025-08-05 | H. Lundbeck A/S | Crystalline forms of a MAGL inhibitor |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0301010D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SE0301009D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SA04250253B1 (ar) | 2003-08-21 | 2009-11-10 | استرازينيكا ايه بي | احماض فينوكسي اسيتيك مستبدلة باعتبارها مركبات صيدلانية لعلاج الامراض التنفسية مثل الربو ومرض الانسداد الرئوي المزمن |
| GB0415320D0 (en) * | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
| GB0418830D0 (en) * | 2004-08-24 | 2004-09-22 | Astrazeneca Ab | Novel compounds |
| GB0422057D0 (en) * | 2004-10-05 | 2004-11-03 | Astrazeneca Ab | Novel compounds |
| ATE517085T1 (de) | 2004-11-23 | 2011-08-15 | Astrazeneca Ab | Zur behandlung von atemwegserkrankungen geeignete phenoxyessigsäurederivate |
| US8148572B2 (en) | 2005-10-06 | 2012-04-03 | Astrazeneca Ab | Compounds |
| TW200745003A (en) | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| ES2380683T3 (es) * | 2005-12-15 | 2012-05-17 | Astrazeneca Ab | Difenil-éteres, -amidas, -sulfuros y - metanos sustituidos para el tratamiento de la enfermedad respiratoria |
| UA100983C2 (ru) * | 2007-07-05 | 2013-02-25 | Астразенека Аб | Бифенилоксипропановая кислота как модулятор crth2 и интермедиаты |
| EP2590944B1 (en) | 2010-07-05 | 2015-09-30 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| WO2013088109A1 (en) | 2011-12-16 | 2013-06-20 | Oxagen Limited | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
| ES2624379T3 (es) | 2011-12-21 | 2017-07-14 | Idorsia Pharmaceuticals Ltd | Derivados de heterociclilo y su uso como moduladores del receptor de prostaglandina D2 |
| US9169270B2 (en) | 2012-07-05 | 2015-10-27 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin D2 receptor modulators |
| US9844218B2 (en) | 2013-06-13 | 2017-12-19 | Monsanto Technology Llc | Acetyl-CoA carboxylase modulators |
| AR096613A1 (es) | 2013-06-13 | 2016-01-20 | Monsanto Technology Llc | Moduladores de la acetil-coa carboxilasa |
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| US3278524A (en) * | 1962-03-13 | 1966-10-11 | Beecham Group Ltd | Penicillins and their production |
| JPS5239888B2 (enExample) * | 1973-05-28 | 1977-10-07 | ||
| US4670566A (en) * | 1979-07-12 | 1987-06-02 | A. H. Robins Company, Incorporated | 3-methyl-hio-4-(5-, 6-, or 7-)phenylindolindolin-2-ones |
| US5006542A (en) * | 1988-10-31 | 1991-04-09 | E. R. Squibb & Sons, Inc. | Arylthioalkylphenyl carboxylic acids, derivatives thereof, compositions containing same and method of use |
| US5145790A (en) * | 1990-05-04 | 1992-09-08 | Abbott Laboratories | Reagents and method for detecting polychlorinated biphenyls |
| CA2090283A1 (en) * | 1992-02-28 | 1993-08-29 | Nobuyuki Hamanaka | Phenoxyacetic acid derivatives |
| JPH06313995A (ja) * | 1993-04-28 | 1994-11-08 | Hodogaya Chem Co Ltd | 静電荷像現像用トナー |
| FR2763588B1 (fr) * | 1997-05-23 | 1999-07-09 | Cird Galderma | Composes triaromatiques, compositions les contenant et utilisations |
| CA2304713C (en) * | 1997-10-14 | 2003-06-10 | Asahi Kasei Kogyo Kabushiki Kaisha | Biphenyl-5-alkanoic acid derivatives and use thereof |
| US6417212B1 (en) * | 1999-08-27 | 2002-07-09 | Eli Lilly & Company | Modulators of peroxisome proliferator activated receptors |
| HUP0301802A3 (en) * | 2000-06-28 | 2009-04-28 | Teva Pharma | Process for producing carvedilol, crystalline carvedilol, process for producing it and pharmaceutical composition containing it |
| US6878522B2 (en) * | 2000-07-07 | 2005-04-12 | Baiyong Li | Methods for the identification of compounds useful for the treatment of disease states mediated by prostaglandin D2 |
| US20040097555A1 (en) * | 2000-12-26 | 2004-05-20 | Shinegori Ohkawa | Concomitant drugs |
| WO2002100399A1 (en) * | 2001-06-12 | 2002-12-19 | Elan Pharmaceuticals, Inc. | Macrocycles useful in the treatment of alzheimer's disease |
| NZ535603A (en) * | 2002-03-20 | 2007-10-26 | Metabolex Inc | Substituted phenylacetic acids |
| ES2401079T3 (es) * | 2002-12-20 | 2013-04-16 | Amgen Inc. | Moduladores del asma y de la inflamación alérgica |
| SE0301010D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SE0301009D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SA04250253B1 (ar) * | 2003-08-21 | 2009-11-10 | استرازينيكا ايه بي | احماض فينوكسي اسيتيك مستبدلة باعتبارها مركبات صيدلانية لعلاج الامراض التنفسية مثل الربو ومرض الانسداد الرئوي المزمن |
| US7166738B2 (en) * | 2004-04-23 | 2007-01-23 | Roche Palo Alto Llc | Non-nucleoside reverse transcriptase inhibitors |
| GB0415320D0 (en) * | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
| GB0418830D0 (en) * | 2004-08-24 | 2004-09-22 | Astrazeneca Ab | Novel compounds |
| GB0422057D0 (en) * | 2004-10-05 | 2004-11-03 | Astrazeneca Ab | Novel compounds |
| ATE517085T1 (de) * | 2004-11-23 | 2011-08-15 | Astrazeneca Ab | Zur behandlung von atemwegserkrankungen geeignete phenoxyessigsäurederivate |
| US8148572B2 (en) * | 2005-10-06 | 2012-04-03 | Astrazeneca Ab | Compounds |
| TW200745003A (en) * | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| ES2380683T3 (es) * | 2005-12-15 | 2012-05-17 | Astrazeneca Ab | Difenil-éteres, -amidas, -sulfuros y - metanos sustituidos para el tratamiento de la enfermedad respiratoria |
| UA100983C2 (ru) * | 2007-07-05 | 2013-02-25 | Астразенека Аб | Бифенилоксипропановая кислота как модулятор crth2 и интермедиаты |
-
2006
- 2006-11-01 EP EP06808382A patent/EP1948630A2/en not_active Withdrawn
- 2006-11-01 JP JP2008539486A patent/JP2009514935A/ja not_active Withdrawn
- 2006-11-01 US US12/092,431 patent/US20080255150A1/en not_active Abandoned
- 2006-11-01 WO PCT/GB2006/004075 patent/WO2007052023A2/en not_active Ceased
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11530189B2 (en) | 2012-01-06 | 2022-12-20 | H. Lundbecka/S | Carbamate compounds and methods of making and using same |
| US12018004B2 (en) | 2012-01-06 | 2024-06-25 | H. Lundbeck A/S | Carbamate compounds and methods of making and using same |
| JP2020500178A (ja) * | 2016-11-16 | 2020-01-09 | ルンドベック ラ ホーヤ リサーチ センター,インク. | Magl阻害剤 |
| JP2020504707A (ja) * | 2016-11-16 | 2020-02-13 | ルンドベック ラ ホーヤ リサーチ センター,インク. | Magl阻害剤 |
| JP7042547B2 (ja) | 2016-11-16 | 2022-03-28 | ルンドベック ラ ホーヤ リサーチ センター,インク. | Magl阻害剤 |
| JP7042468B2 (ja) | 2016-11-16 | 2022-03-28 | ルンドベック ラ ホーヤ リサーチ センター,インク. | Magl阻害剤 |
| US11691975B2 (en) | 2016-11-16 | 2023-07-04 | H. Lundbecka/S | MAGL inhibitors |
| US11332453B2 (en) | 2018-05-15 | 2022-05-17 | H. Lundbeck A/S | MAGL inhibitors |
| US12378219B2 (en) | 2022-05-04 | 2025-08-05 | H. Lundbeck A/S | Crystalline forms of a MAGL inhibitor |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007052023A2 (en) | 2007-05-10 |
| WO2007052023A3 (en) | 2007-11-08 |
| US20080255150A1 (en) | 2008-10-16 |
| EP1948630A2 (en) | 2008-07-30 |
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