TWI336322B - Substituted phenoxyacetic acids and pharmaceutical compositions and uses thereof - Google Patents
Substituted phenoxyacetic acids and pharmaceutical compositions and uses thereof Download PDFInfo
- Publication number
- TWI336322B TWI336322B TW093108313A TW93108313A TWI336322B TW I336322 B TWI336322 B TW I336322B TW 093108313 A TW093108313 A TW 093108313A TW 93108313 A TW93108313 A TW 93108313A TW I336322 B TWI336322 B TW I336322B
- Authority
- TW
- Taiwan
- Prior art keywords
- oxy
- acetic acid
- biphenyl
- trifluoromethyl
- methyl
- Prior art date
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- 239000008194 pharmaceutical composition Chemical class 0.000 title claims description 13
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 title claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 428
- 150000001875 compounds Chemical class 0.000 claims description 241
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 200
- 239000004305 biphenyl Substances 0.000 claims description 177
- -1 benzo[b]thienyl Chemical group 0.000 claims description 87
- 235000010290 biphenyl Nutrition 0.000 claims description 78
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 67
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 50
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
- 201000010099 disease Diseases 0.000 claims description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 25
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 21
- 239000007789 gas Substances 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 19
- 206010039083 rhinitis Diseases 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 13
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 208000006673 asthma Diseases 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000001041 indolyl group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- 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 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 150000002923 oximes Chemical class 0.000 claims description 5
- 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 5
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 150000004702 methyl esters Chemical class 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000002602 lanthanoids Chemical class 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- LRYZJEXQHWCLJY-UHFFFAOYSA-N 1-phenyl-2-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=CC=C1C1=CC=CC=C1 LRYZJEXQHWCLJY-UHFFFAOYSA-N 0.000 claims description 2
- XCCVYEJDWRXGTG-UHFFFAOYSA-N 2-[2-quinolin-8-yl-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC2=CC=CN=C12 XCCVYEJDWRXGTG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 101100134929 Gallus gallus COR9 gene Proteins 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
- 125000006308 propyl amino group Chemical group 0.000 claims description 2
- 208000023504 respiratory system disease Diseases 0.000 claims description 2
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- GEAGOTGYCOZVOX-NSHDSACASA-N (2s)-2-[2-[4-(dimethylsulfamoyl)phenyl]-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1C1=CC=C(S(=O)(=O)N(C)C)C=C1 GEAGOTGYCOZVOX-NSHDSACASA-N 0.000 claims 1
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 claims 1
- ZKXGQPQAMRSBOL-UHFFFAOYSA-N 1,2,3-trifluoro-9h-fluorene Chemical compound C12=CC=CC=C2CC2=C1C=C(F)C(F)=C2F ZKXGQPQAMRSBOL-UHFFFAOYSA-N 0.000 claims 1
- HLHVPJVNRURVNK-UHFFFAOYSA-N 2-(4-cyano-2-phenylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C#N)C=C1C1=CC=CC=C1 HLHVPJVNRURVNK-UHFFFAOYSA-N 0.000 claims 1
- WVZDLNVAAOUNAU-UHFFFAOYSA-N 2-[2-(2-amino-4-methylpyrimidin-5-yl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=NC(N)=NC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O WVZDLNVAAOUNAU-UHFFFAOYSA-N 0.000 claims 1
- KDOSMMYSHYZFQE-UHFFFAOYSA-N 2-[2-(4-ethylsulfonyl-2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O KDOSMMYSHYZFQE-UHFFFAOYSA-N 0.000 claims 1
- JUKQBUGEOLGQHR-UHFFFAOYSA-N 2-[4-chloro-2-(4-cyanophenyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C1=CC=C(C#N)C=C1 JUKQBUGEOLGQHR-UHFFFAOYSA-N 0.000 claims 1
- MREHKHMPXVGCAP-UHFFFAOYSA-N 2-[4-chloro-2-(4-ethylsulfonylphenyl)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O MREHKHMPXVGCAP-UHFFFAOYSA-N 0.000 claims 1
- PVQZLNPEACVEOJ-UHFFFAOYSA-N 2-[4-chloro-2-(4-methyl-2-morpholin-4-ylpyrimidin-5-yl)phenoxy]acetic acid Chemical compound CC1=NC(N2CCOCC2)=NC=C1C1=CC(Cl)=CC=C1OCC(O)=O PVQZLNPEACVEOJ-UHFFFAOYSA-N 0.000 claims 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims 1
- 101100533890 Hypocrea jecorina (strain QM6a) sor3 gene Proteins 0.000 claims 1
- 101100533874 Hypocrea jecorina (strain QM6a) sor5 gene Proteins 0.000 claims 1
- 241001529936 Murinae Species 0.000 claims 1
- 229910001347 Stellite Inorganic materials 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- AHICWQREWHDHHF-UHFFFAOYSA-N chromium;cobalt;iron;manganese;methane;molybdenum;nickel;silicon;tungsten Chemical compound C.[Si].[Cr].[Mn].[Fe].[Co].[Ni].[Mo].[W] AHICWQREWHDHHF-UHFFFAOYSA-N 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- IEMGWBMVQLVHEY-UHFFFAOYSA-N ethyl 2-(3-amino-6,7-dihydro-5h-cyclopenta[b]pyridin-7-yl)acetate Chemical compound NC1=CN=C2C(CC(=O)OCC)CCC2=C1 IEMGWBMVQLVHEY-UHFFFAOYSA-N 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 description 217
- 238000001819 mass spectrum Methods 0.000 description 206
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 202
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 184
- 239000000047 product Substances 0.000 description 173
- 238000000034 method Methods 0.000 description 121
- 235000019439 ethyl acetate Nutrition 0.000 description 85
- 239000000203 mixture Substances 0.000 description 77
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
- 206010057190 Respiratory tract infections Diseases 0.000 description 58
- 239000000243 solution Substances 0.000 description 54
- 230000002829 reductive effect Effects 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 229940095574 propionic acid Drugs 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 101150041968 CDC13 gene Proteins 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 27
- 238000004587 chromatography analysis Methods 0.000 description 27
- 239000002585 base Substances 0.000 description 25
- 239000003112 inhibitor Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 15
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 13
- 230000001154 acute effect Effects 0.000 description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
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- 210000004027 cell Anatomy 0.000 description 12
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
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- 230000000694 effects Effects 0.000 description 11
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
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| JP2009528273A (ja) * | 2006-01-25 | 2009-08-06 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連使用用の置換ビアリール化合物 |
| CA2640090A1 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted aromatic compounds for inflammation and immune-related uses |
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| EP2152707B1 (en) | 2007-05-04 | 2012-06-20 | Bristol-Myers Squibb Company | [6,5]-bicyclic gpr119 g protein-coupled receptor agonists |
| CN101668756A (zh) | 2007-05-04 | 2010-03-10 | 百时美施贵宝公司 | [6,6]和[6,7]-双环gpr119 g蛋白偶合受体激动剂 |
| UA100983C2 (ru) * | 2007-07-05 | 2013-02-25 | Астразенека Аб | Бифенилоксипропановая кислота как модулятор crth2 и интермедиаты |
| HRP20110806T1 (hr) | 2007-07-17 | 2011-11-30 | Bristol-Myers Squibb Company | Agonisti piridon gpr119 g protein-vezanih receptora |
| JP5485884B2 (ja) * | 2007-07-26 | 2014-05-07 | ノバルティス アーゲー | 炎症性またはアレルギー性状態の処置に有用なピリミジン誘導体 |
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| PH12012501853A1 (en) | 2010-04-08 | 2013-01-07 | Bristol Myers Squibb Co | Pyrimidinylpiperidinyloxypyridinone analogues as gpr119 modulators |
| KR101920090B1 (ko) | 2010-07-05 | 2018-11-19 | 이도르시아 파마슈티컬스 리미티드 | 1-페닐-치환된 헤테로시클릴 유도체 및 프로스타글란딘 d2 수용체 조절자로서 이의 용도 |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
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| TWI550071B (zh) | 2011-03-25 | 2016-09-21 | 捷恩智股份有限公司 | 原酸酯化合物、液晶組成物及液晶顯示元件 |
| CN102408286B (zh) * | 2011-09-14 | 2013-11-13 | 浙江工业大学 | 一种n,n-二取代磺酰胺类化合物的制备方法 |
| EP2790696A1 (en) | 2011-12-16 | 2014-10-22 | Atopix Therapeutics 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 |
| CN104428305A (zh) * | 2012-07-05 | 2015-03-18 | 埃科特莱茵药品有限公司 | 1-苯基-取代的杂环衍生物及其作为前列腺素d2受体调节剂的用途 |
| DK3013796T3 (da) | 2013-06-27 | 2020-03-16 | Lg Chemical Ltd | Biarylderivater som gpr120-agonister |
| JP2015051936A (ja) * | 2013-09-06 | 2015-03-19 | 株式会社日本触媒 | ホウ素化合物の製造方法 |
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