JP2009514935A5 - - Google Patents
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- JP2009514935A5 JP2009514935A5 JP2008539486A JP2008539486A JP2009514935A5 JP 2009514935 A5 JP2009514935 A5 JP 2009514935A5 JP 2008539486 A JP2008539486 A JP 2008539486A JP 2008539486 A JP2008539486 A JP 2008539486A JP 2009514935 A5 JP2009514935 A5 JP 2009514935A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- halogen
- alkyl
- optionally
- phenyl
- 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- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 24
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims 1
- 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 1
- 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 1
- 150000003180 prostaglandins Chemical class 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 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 1
- 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 1
- 239000012453 solvate Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 239000012528 membrane Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011324 bead Substances 0.000 description 5
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 239000011539 homogenization buffer Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000012131 assay buffer Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229960002390 flurbiprofen Drugs 0.000 description 2
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 2
- BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical class CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 108010001478 Bacitracin Proteins 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- ZWXHOPKAIHVWSE-UHFFFAOYSA-N C(C)(=O)O.B Chemical compound C(C)(=O)O.B ZWXHOPKAIHVWSE-UHFFFAOYSA-N 0.000 description 1
- FTUUUVFSQJJONC-MERQFXBCSA-N C(C)(C)(C)CS(=O)(=O)Cl.ClC=1C=CC(=C(CN2C[C@@H](N(CC2)C(=O)O)C)C1)CC(=O)OC Chemical compound C(C)(C)(C)CS(=O)(=O)Cl.ClC=1C=CC(=C(CN2C[C@@H](N(CC2)C(=O)O)C)C1)CC(=O)OC FTUUUVFSQJJONC-MERQFXBCSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 102000018697 Membrane Proteins Human genes 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960001671 azapropazone Drugs 0.000 description 1
- WOIIIUDZSOLAIW-NSHDSACASA-N azapropazone Chemical compound C1=C(C)C=C2N3C(=O)[C@H](CC=C)C(=O)N3C(N(C)C)=NC2=C1 WOIIIUDZSOLAIW-NSHDSACASA-N 0.000 description 1
- 229960003071 bacitracin Drugs 0.000 description 1
- 229930184125 bacitracin Natural products 0.000 description 1
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940111134 coxibs Drugs 0.000 description 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
- 229960001259 diclofenac Drugs 0.000 description 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229960001419 fenoprofen Drugs 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
- 229960000991 ketoprofen Drugs 0.000 description 1
- 238000000670 ligand binding assay Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229960003464 mefenamic acid Drugs 0.000 description 1
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 229960002702 piroxicam Drugs 0.000 description 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960000894 sulindac Drugs 0.000 description 1
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
- DATRVIMZZZVHMP-QMMMGPOBSA-N tert-butyl (2s)-2-methylpiperazine-1-carboxylate Chemical compound C[C@H]1CNCCN1C(=O)OC(C)(C)C DATRVIMZZZVHMP-QMMMGPOBSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| GB0522619A GB0522619D0 (en) | 2005-11-05 | 2005-11-05 | Novel compounds |
| GB0607353A GB0607353D0 (en) | 2006-04-12 | 2006-04-12 | Novel Compounds |
| PCT/GB2006/004075 WO2007052023A2 (en) | 2005-11-05 | 2006-11-01 | Novel compounds |
Publications (2)
| Publication Number | Publication Date |
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| JP2009514935A JP2009514935A (ja) | 2009-04-09 |
| JP2009514935A5 true JP2009514935A5 (enExample) | 2009-10-22 |
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| EP (1) | EP1948630A2 (enExample) |
| JP (1) | JP2009514935A (enExample) |
| WO (1) | WO2007052023A2 (enExample) |
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| 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 |
| EP1817282B1 (en) | 2004-11-23 | 2011-07-20 | AstraZeneca AB | Phenoxyacetic acid derivatives useful for treating respiratory diseases |
| TW200745003A (en) | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| EP1937632A1 (en) | 2005-10-06 | 2008-07-02 | Astra Zeneca 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 |
| CA2805452C (en) * | 2010-07-05 | 2018-07-31 | 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 |
| CN104114169A (zh) | 2011-12-16 | 2014-10-22 | 阿托佩斯治疗有限公司 | 用于治疗嗜酸细胞性食管炎的crth2拮抗剂和质子泵抑制剂的组合物 |
| TW201331179A (zh) | 2011-12-21 | 2013-08-01 | Actelion Pharmaceuticals Ltd | 雜環衍生物及其作為前列腺素ｄ２受體調節劑之用途 |
| NZ627750A (en) | 2012-01-06 | 2016-11-25 | Abide Therapeutics Inc | Carbamate compounds and of making and using same |
| EP2885307A1 (en) | 2012-07-05 | 2015-06-24 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| WO2014201327A1 (en) | 2013-06-13 | 2014-12-18 | Monsanto Technology Llc | Acetyl-coa carboxylase modulators |
| US9844218B2 (en) | 2013-06-13 | 2017-12-19 | Monsanto Technology Llc | Acetyl-CoA carboxylase modulators |
| JOP20190106A1 (ar) * | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| JOP20190107A1 (ar) | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| MA52635A (fr) | 2018-05-15 | 2021-03-24 | H Lundbeck As | Inhibiteurs de magl |
| WO2023213854A1 (en) | 2022-05-04 | 2023-11-09 | H. Lundbeck A/S | Crystalline form of 1,1,1,3,3,3-hexafluoropropan-2-yl (s)-1-(pyridazin-3-ylcarbamoyl)-6 azaspiro[2.5]octane-6-carboxylate as monoacylglycerol lipase inhibitor. |
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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 |
| WO2001016120A1 (en) * | 1999-08-27 | 2001-03-08 | Eli Lilly And Company | Biaryl-oxa(thia)zole derivatives and their use as ppars modulators |
| CA2413702A1 (en) * | 2000-06-28 | 2002-01-03 | Teva Pharmaceuticals Industries Ltd. | Carvedilol |
| 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 |
| EP1395257A1 (en) * | 2001-06-12 | 2004-03-10 | Elan Pharmaceuticals, Inc. | Macrocycles useful in the treatment of alzheimer's disease |
| MXPA04009040A (es) * | 2002-03-20 | 2005-01-25 | Metabolex Inc | Acidos fenilaceticos sustituidos. |
| ES2401079T3 (es) * | 2002-12-20 | 2013-04-16 | Amgen Inc. | Moduladores del asma y de la inflamación alérgica |
| SE0301009D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SE0301010D0 (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 |
| EP1817282B1 (en) * | 2004-11-23 | 2011-07-20 | AstraZeneca AB | Phenoxyacetic acid derivatives useful for treating respiratory diseases |
| EP1937632A1 (en) * | 2005-10-06 | 2008-07-02 | Astra Zeneca AB | Novel 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 US US12/092,431 patent/US20080255150A1/en not_active Abandoned
- 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 WO PCT/GB2006/004075 patent/WO2007052023A2/en not_active Ceased
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