JP2008500991A - 医学的使用のためのcrth2レセプターリガンド - Google Patents
医学的使用のためのcrth2レセプターリガンド Download PDFInfo
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- JP2008500991A JP2008500991A JP2007513846A JP2007513846A JP2008500991A JP 2008500991 A JP2008500991 A JP 2008500991A JP 2007513846 A JP2007513846 A JP 2007513846A JP 2007513846 A JP2007513846 A JP 2007513846A JP 2008500991 A JP2008500991 A JP 2008500991A
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- Prior art keywords
- bromo
- phenoxy
- carbonyl
- pyrazole
- acetic acid
- Prior art date
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- 102000009389 Prostaglandin D receptors Human genes 0.000 title claims abstract description 24
- 108050000258 Prostaglandin D receptors Proteins 0.000 title claims abstract description 24
- 239000003446 ligand Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 165
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
- 239000001257 hydrogen Substances 0.000 claims abstract description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
- 201000010099 disease Diseases 0.000 claims abstract description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
- 230000000694 effects Effects 0.000 claims abstract description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 208000006673 asthma Diseases 0.000 claims abstract description 9
- 206010039083 rhinitis Diseases 0.000 claims abstract description 9
- 230000000172 allergic effect Effects 0.000 claims abstract description 6
- 208000028004 allergic respiratory disease Diseases 0.000 claims abstract description 6
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 6
- 125000006413 ring segment Chemical group 0.000 claims abstract description 6
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 5
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
- -1 trifluoromethoxy, trifluoro Methylthio, dimethylamino Chemical group 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 26
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 20
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 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 17
- 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 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 235000019260 propionic acid Nutrition 0.000 claims description 10
- 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 10
- 239000012453 solvate Substances 0.000 claims description 10
- 125000000335 thiazolyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 210000003979 eosinophil Anatomy 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- JZKMIPDOAWBAHE-NVQRDWNXSA-N (2r,3r,4s,5r)-2-[6-[cyclohexyl(prop-2-enyl)amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(N(CC=C)C3CCCCC3)=C2N=C1 JZKMIPDOAWBAHE-NVQRDWNXSA-N 0.000 claims description 4
- YVCFNRBEJVGESH-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-bromo-4-methylphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound BrC1=CC(C)=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 YVCFNRBEJVGESH-UHFFFAOYSA-N 0.000 claims description 4
- YOBMCDVFDDJFFV-UHFFFAOYSA-N 2-[4-bromo-2-[1-(4-bromo-2-chlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC(Br)=CC=2)Cl)N=C1 YOBMCDVFDDJFFV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 240000008570 Digitaria exilis Species 0.000 claims description 4
- 235000005459 Digitaria exilis Nutrition 0.000 claims description 4
- 235000010575 Pueraria lobata Nutrition 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 201000001981 dermatomyositis Diseases 0.000 claims description 4
- 125000002720 diazolyl group Chemical group 0.000 claims description 4
- 201000002491 encephalomyelitis Diseases 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 208000002574 reactive arthritis Diseases 0.000 claims description 4
- 201000000306 sarcoidosis Diseases 0.000 claims description 4
- 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 4
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 4
- QIQZFDHLXPAAIR-LBPRGKRZSA-N (2s)-2-[4-bromo-2-(1-phenylpyrazole-4-carbonyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 QIQZFDHLXPAAIR-LBPRGKRZSA-N 0.000 claims description 3
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 3
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 3
- LSPQNLQIYOKMTN-UHFFFAOYSA-N 2-[2-[1-(2-bromophenyl)pyrazole-4-carbonyl]-4-ethylphenoxy]acetic acid Chemical compound CCC1=CC=C(OCC(O)=O)C(C(=O)C2=CN(N=C2)C=2C(=CC=CC=2)Br)=C1 LSPQNLQIYOKMTN-UHFFFAOYSA-N 0.000 claims description 3
- QLCCLVILESTJNX-UHFFFAOYSA-N 2-[2-[1-(2-chlorophenyl)pyrazole-4-carbonyl]-4-nitrophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CN(C=2C(=CC=CC=2)Cl)N=C1 QLCCLVILESTJNX-UHFFFAOYSA-N 0.000 claims description 3
- BUNCEUVLTVTITF-UHFFFAOYSA-N 2-[4-bromo-2-(1-naphthalen-1-ylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C3=CC=CC=C3C=CC=2)N=C1 BUNCEUVLTVTITF-UHFFFAOYSA-N 0.000 claims description 3
- DMFOOUGJUFPBOG-UHFFFAOYSA-N 2-[4-bromo-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 DMFOOUGJUFPBOG-UHFFFAOYSA-N 0.000 claims description 3
- QIQZFDHLXPAAIR-UHFFFAOYSA-N 2-[4-bromo-2-(1-phenylpyrazole-4-carbonyl)phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 QIQZFDHLXPAAIR-UHFFFAOYSA-N 0.000 claims description 3
- DTXMBWBTTBVOAE-UHFFFAOYSA-N 2-[4-bromo-2-(1-pyridin-2-ylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2N=CC=CC=2)N=C1 DTXMBWBTTBVOAE-UHFFFAOYSA-N 0.000 claims description 3
- AQNZKLWCJXMBRM-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,4,6-trichlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC(Cl)=CC=2Cl)Cl)N=C1 AQNZKLWCJXMBRM-UHFFFAOYSA-N 0.000 claims description 3
- LNKFHOQVEVTLKK-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,4,6-trichlorophenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC(Cl)=CC=2Cl)Cl)N=C1 LNKFHOQVEVTLKK-UHFFFAOYSA-N 0.000 claims description 3
- FVFWAOFXTIHIKN-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,4-dibromophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC(Br)=CC=2)Br)N=C1 FVFWAOFXTIHIKN-UHFFFAOYSA-N 0.000 claims description 3
- KCUBSRLDNLOFHO-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,4-dichlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC(Cl)=CC=2)Cl)N=C1 KCUBSRLDNLOFHO-UHFFFAOYSA-N 0.000 claims description 3
- GKJHYSSXTQZZKW-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,4-dimethylphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound CC1=CC(C)=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 GKJHYSSXTQZZKW-UHFFFAOYSA-N 0.000 claims description 3
- UYBKPKQYTBHMHL-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,5-dichlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=C(Cl)C=2)Cl)N=C1 UYBKPKQYTBHMHL-UHFFFAOYSA-N 0.000 claims description 3
- HBIZRZDCSVBMII-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,6-dichlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2Cl)Cl)N=C1 HBIZRZDCSVBMII-UHFFFAOYSA-N 0.000 claims description 3
- PGKHSJWQTQODLJ-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,6-dichlorophenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2Cl)Cl)N=C1 PGKHSJWQTQODLJ-UHFFFAOYSA-N 0.000 claims description 3
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- HYXYEMCQQAEHCZ-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-methylsulfanylphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound CSC1=CC=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 HYXYEMCQQAEHCZ-UHFFFAOYSA-N 0.000 claims description 3
- WHRYRALKFCAFQN-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-phenoxyphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N=C1 WHRYRALKFCAFQN-UHFFFAOYSA-N 0.000 claims description 3
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- ZVAVUDKJOCDNFX-UHFFFAOYSA-N 2-[4-bromo-2-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(C=2C=CC(Cl)=CC=2)=NO1 ZVAVUDKJOCDNFX-UHFFFAOYSA-N 0.000 claims description 3
- IEYUEAWAOCCAKN-UHFFFAOYSA-N 2-[4-bromo-2-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(C=2C=CC(F)=CC=2)=NO1 IEYUEAWAOCCAKN-UHFFFAOYSA-N 0.000 claims description 3
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| GB0414196A GB0414196D0 (en) | 2004-06-24 | 2004-06-24 | Medicinal use of receptor ligands |
| GB0424018A GB0424018D0 (en) | 2004-10-29 | 2004-10-29 | Medicinal use of receptor ligands |
| PCT/EP2005/005884 WO2005115382A1 (en) | 2004-05-29 | 2005-05-30 | Crth2 receptor ligands for medicinal uses |
Publications (2)
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| JP2008500991A true JP2008500991A (ja) | 2008-01-17 |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011528004A (ja) * | 2008-07-15 | 2011-11-10 | エフ.ホフマン−ラ ロシュ アーゲー | アミノテトラヒドロインダゾロ酢酸 |
| JP2011528002A (ja) * | 2008-07-15 | 2011-11-10 | エフ.ホフマン−ラ ロシュ アーゲー | アミノテトラヒドロインダゾロ酢酸 |
| JP2013082729A (ja) * | 2004-11-23 | 2013-05-09 | Astrazeneca Ab | 呼吸器疾患の処置に有用なフェノキシ酢酸誘導体 |
| JP2015522011A (ja) * | 2012-07-05 | 2015-08-03 | アクテリオン ファーマシューティカルズ リミテッドActelion Pharmaceuticals Ltd | 1−フェニル置換ヘテロシクリル誘導体及びプロスタグランジンd2受容体調節剤としてのそれらの使用 |
| WO2022138700A1 (ja) * | 2020-12-23 | 2022-06-30 | ピアス株式会社 | アトピー性皮膚疾患改善剤、皮膚外用剤、及び、化粧料 |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| CA2622000C (en) * | 2005-09-30 | 2014-01-21 | Argenta Discovery Limited | Quinolines and their therapeutic use |
| TW200745003A (en) | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| US8148572B2 (en) | 2005-10-06 | 2012-04-03 | Astrazeneca Ab | Compounds |
| WO2007062678A1 (en) * | 2005-11-29 | 2007-06-07 | 7Tm Pharma A/S | Phenoxyacetic acid derivatives as crth2 receptor ligands |
| GB0524428D0 (en) * | 2005-11-30 | 2006-01-11 | 7Tm Pharma As | Medicinal use of receptor ligands |
| KR101470659B1 (ko) | 2006-09-07 | 2014-12-08 | 액테리온 파마슈티칼 리미티드 | 면역조절제로서 피리딘-4-일 유도체 |
| US8288554B2 (en) | 2006-09-08 | 2012-10-16 | Actelion Pharmaceuticals Ltd. | Pyridin-3-yl derivatives as immunomodulating agents |
| EP2069318B1 (en) | 2006-09-21 | 2012-09-12 | Actelion Pharmaceuticals Ltd. | Phenyl derivatives and their use as immunomodulators |
| WO2008049864A1 (en) * | 2006-10-25 | 2008-05-02 | Neurosearch A/S | Oxadiazole and thiadiazole compounds and their use as nicotinic acetylcholine receptor modulators |
| ES2383239T3 (es) | 2006-12-14 | 2012-06-19 | Astellas Pharma Inc. | Compuestos de ácidos policíclicos útiles como antagonistas de CRTH2 y como agentes antialérgicos |
| MX2009009597A (es) | 2007-03-16 | 2009-09-16 | Actelion Pharmaceuticals Ltd | Derivados de amino-piridina como agonistas del receptor s1p1/edg1. |
| UA100983C2 (ru) | 2007-07-05 | 2013-02-25 | Астразенека Аб | Бифенилоксипропановая кислота как модулятор crth2 и интермедиаты |
| CN102648198B (zh) | 2007-08-17 | 2015-04-01 | 埃科特莱茵药品有限公司 | 作为s1p1/edg1受体调节剂的吡啶衍生物 |
| MX2010003614A (es) | 2007-10-04 | 2010-04-21 | Merck Serono Sa | Compuestos de diarilo oxadiazol. |
| CA2696863C (en) * | 2007-10-04 | 2016-10-18 | Anna Quattropani | Oxadiazole derivatives |
| BRPI0818804A2 (pt) | 2007-11-01 | 2015-04-22 | Actelion Pharmaceuticals Ltd | Composto derivado de pirimidina, composição farmacêutica que o compreende e uso desse composto. |
| EP2327693B9 (en) | 2007-12-14 | 2012-10-24 | Pulmagen Therapeutics (Asthma) Limited | Indoles and their therapeutic use |
| WO2009082398A1 (en) * | 2007-12-21 | 2009-07-02 | University Of Notre Dame Du Lac | Antibacterial compounds and methods of using same |
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| WO2022138700A1 (ja) * | 2020-12-23 | 2022-06-30 | ピアス株式会社 | アトピー性皮膚疾患改善剤、皮膚外用剤、及び、化粧料 |
Also Published As
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|---|---|
| US8022063B2 (en) | 2011-09-20 |
| EP2336113A1 (en) | 2011-06-22 |
| NO20066048L (no) | 2007-02-27 |
| CR8838A (es) | 2009-01-12 |
| HK1107763A1 (en) | 2008-04-18 |
| US20090099189A1 (en) | 2009-04-16 |
| AU2005247110B2 (en) | 2010-08-26 |
| AU2005247110A1 (en) | 2005-12-08 |
| EA200602290A1 (ru) | 2007-06-29 |
| IL179694A0 (en) | 2008-03-20 |
| IL179694A (en) | 2012-09-24 |
| WO2005115382A1 (en) | 2005-12-08 |
| NZ551810A (en) | 2010-09-30 |
| EA014729B1 (ru) | 2011-02-28 |
| CA2568766A1 (en) | 2005-12-08 |
| US20110269763A1 (en) | 2011-11-03 |
| EP1758579A1 (en) | 2007-03-07 |
| BRPI0511676A (pt) | 2008-01-08 |
| KR20070045153A (ko) | 2007-05-02 |
| MXPA06013912A (es) | 2007-07-18 |
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