ZA200608393B - Substituted methyl aryl or heteroaryl amide compounds - Google Patents
Substituted methyl aryl or heteroaryl amide compounds Download PDFInfo
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- ZA200608393B ZA200608393B ZA200608393A ZA200608393A ZA200608393B ZA 200608393 B ZA200608393 B ZA 200608393B ZA 200608393 A ZA200608393 A ZA 200608393A ZA 200608393 A ZA200608393 A ZA 200608393A ZA 200608393 B ZA200608393 B ZA 200608393B
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- South Africa
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- carbon atoms
- group
- chloro
- compound
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- -1 heteroaryl amide compounds Chemical class 0.000 title claims description 162
- 150000001875 compounds Chemical class 0.000 claims description 206
- 125000004432 carbon atom Chemical group C* 0.000 claims description 81
- 239000002253 acid Substances 0.000 claims description 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 201000010099 disease Diseases 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 239000005711 Benzoic acid Substances 0.000 claims description 20
- 235000010233 benzoic acid Nutrition 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 150000003180 prostaglandins Chemical class 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- BTXUOUJHLMYLQA-ZDUSSCGKSA-N 4-[(1s)-1-[[2-[(4-chlorophenoxy)methyl]-5-fluoropyridine-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(F)=CN=C1COC1=CC=C(Cl)C=C1 BTXUOUJHLMYLQA-ZDUSSCGKSA-N 0.000 claims 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 61
- 238000000034 method Methods 0.000 description 60
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- 230000036407 pain Effects 0.000 description 48
- 238000005160 1H NMR spectroscopy Methods 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 31
- 210000004027 cell Anatomy 0.000 description 31
- 238000009472 formulation Methods 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 229940079593 drug Drugs 0.000 description 16
- 239000012442 inert solvent Substances 0.000 description 16
- 238000002347 injection Methods 0.000 description 16
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- 239000002585 base Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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- 239000003153 chemical reaction reagent Substances 0.000 description 14
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 13
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 8
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- ZDBCTVWSSRAJEU-UHFFFAOYSA-N methyl 2-(2-bromoethyl)-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1CCBr ZDBCTVWSSRAJEU-UHFFFAOYSA-N 0.000 description 8
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- 125000002252 acyl group Chemical group 0.000 description 7
- 239000005557 antagonist Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
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Classifications
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
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- C07D213/65—One oxygen atom attached in position 3 or 5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
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- 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
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- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
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US (2) | US7534914B2 (fr) |
EP (1) | EP1756042B8 (fr) |
JP (1) | JP4054368B2 (fr) |
KR (1) | KR20070006891A (fr) |
CN (1) | CN1950333A (fr) |
AP (1) | AP2006003785A0 (fr) |
AR (1) | AR048642A1 (fr) |
AU (1) | AU2005238291A1 (fr) |
BR (1) | BRPI0510666A (fr) |
CA (1) | CA2565813C (fr) |
CR (1) | CR8730A (fr) |
DO (1) | DOP2005000071A (fr) |
EA (1) | EA200601847A1 (fr) |
EC (1) | ECSP066968A (fr) |
ES (1) | ES2461265T3 (fr) |
GT (1) | GT200500101A (fr) |
IL (1) | IL178676A0 (fr) |
MA (1) | MA28571B1 (fr) |
MX (1) | MXPA06011555A (fr) |
NL (1) | NL1028947C2 (fr) |
NO (1) | NO20065578L (fr) |
PA (1) | PA8631201A1 (fr) |
PE (1) | PE20060306A1 (fr) |
SV (1) | SV2005002102A (fr) |
TN (1) | TNSN06358A1 (fr) |
TW (1) | TW200536541A (fr) |
UY (1) | UY28877A1 (fr) |
WO (1) | WO2005105732A1 (fr) |
ZA (1) | ZA200608393B (fr) |
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US7446220B2 (en) | 2005-09-19 | 2008-11-04 | Teva Pharmaceutical Industries Ltd. | Asymmetric synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid |
EP1969129B1 (fr) | 2005-12-28 | 2009-03-11 | Basf Se | Procédé de préparation du sulfate de l'ester méthylique d'acide 4-(1-aminoéthyl) benzoique (r) et (s) à partir de l'ester méthylique d'acide 4-(1-aminoéthyl) benzoique racémique |
DE102005062966A1 (de) * | 2005-12-28 | 2007-07-05 | Basf Ag | Verfahren zur Herstellung von (R)- und (S)-4-(Ammoniumethyl)benzoesäuremethylester-sulfat |
UY30121A1 (es) | 2006-02-03 | 2007-08-31 | Glaxo Group Ltd | Nuevos compuestos |
CA2660133C (fr) * | 2006-08-11 | 2015-10-27 | Merck Frosst Canada Ltd. | Derives de thiophenecarboxamide en tant que ligands du recepteur ep4 |
JP5069752B2 (ja) | 2006-12-15 | 2012-11-07 | グラクソ グループ リミテッド | Ep4受容体アゴニストとしてのベンズアミド誘導体 |
WO2009005076A1 (fr) | 2007-07-03 | 2009-01-08 | Astellas Pharma Inc. | Composé amide |
GB0721611D0 (en) * | 2007-11-02 | 2007-12-12 | Glaxo Group Ltd | Novel compounds |
PT2565191E (pt) | 2008-05-14 | 2014-12-04 | Astellas Pharma Inc | Derivados do ácido 4-(indol-7- ilcarbonilaminometil)ciclo-hexanocarboxílico como antagonistas de receptores ep4, úteis no tratamento de insuficiência renal crónica ou de nefropatia diabética |
US20100087525A1 (en) * | 2008-06-23 | 2010-04-08 | Lilach Hedvati | Stereoselective enzymatic synthesis of (s) or (r)-iso-butyl-glutaric ester |
WO2010087425A1 (fr) | 2009-01-30 | 2010-08-05 | 国立大学法人京都大学 | Inhibiteur de la progression du cancer de la prostate et procédé d'inhibition de la progression |
CN105596320B (zh) | 2009-04-22 | 2019-03-22 | 株式会社AskAt | 癌症治疗用选择性ep4受体拮抗物质 |
CN107693518A (zh) * | 2010-02-22 | 2018-02-16 | 株式会社AskAt | Ep‑4受体拮抗剂在治疗il‑23介导疾病中的用途 |
CN103097358B (zh) * | 2010-09-21 | 2015-04-08 | 卫材R&D管理有限公司 | 药物组合物 |
EP2649061B1 (fr) | 2010-12-10 | 2015-05-13 | Rottapharm Biotech S.r.l. | Dérivés de pyridinamide en tant qu'antagonistes de récepteur ep4 |
ES2559513T3 (es) | 2011-07-04 | 2016-02-12 | Rottapharm Biotech S.R.L. | Derivados de amina cíclica como antagonistas del receptor EP4 |
WO2013032977A1 (fr) | 2011-08-29 | 2013-03-07 | Ticona Llc | Composition de polymère à cristaux liquides résistante à la chaleur ayant une faible température de fusion |
US8669341B2 (en) | 2011-08-29 | 2014-03-11 | Ticona Llc | Solid-state polymerization of a liquid crystalline polymer |
CN103764793B (zh) | 2011-08-29 | 2016-09-14 | 提克纳有限责任公司 | 高流动液晶聚合物组合物 |
TW201319023A (zh) | 2011-08-29 | 2013-05-16 | Ticona Llc | 具改良低剪切黏度之熱向性液晶聚合物 |
US9057016B2 (en) | 2011-08-29 | 2015-06-16 | Ticona Llc | Melt polymerization of low melt viscosity liquid crystalline polymers |
US8778221B2 (en) | 2011-08-29 | 2014-07-15 | Ticona Llc | Aromatic amide compound |
WO2013032971A1 (fr) | 2011-08-29 | 2013-03-07 | Ticona Llc | Substrat extrudé à l'état fondu destiné être utilisé dans des articles thermoformés |
WO2013032967A1 (fr) | 2011-08-29 | 2013-03-07 | Ticona Llc | Pièces coulées au moule formées à partir d'un polymère cristallin liquide |
JP2014525498A (ja) | 2011-08-29 | 2014-09-29 | ティコナ・エルエルシー | 高流動性液晶ポリマー組成物 |
AR091429A1 (es) * | 2012-06-29 | 2015-02-04 | Lilly Co Eli | Compuestos de fenoxietil piperidina |
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WO2014130275A2 (fr) | 2013-02-22 | 2014-08-28 | Ticona Llc | Composition de polymères haute performance présentant des propriétés d'écoulement améliorées |
MX2015013328A (es) | 2013-03-19 | 2016-02-26 | Askat Inc | Uso de antagonistas del receptor de ep4 en el tratamiento de enfermedad de cartilago. |
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EP2991634A1 (fr) | 2013-04-30 | 2016-03-09 | Otitopic Inc. | Formulations de poudre sèche et procédés d'utilisation |
TWI636046B (zh) | 2013-05-17 | 2018-09-21 | 美國禮來大藥廠 | 苯氧基乙基二氫-1h-異喹啉化合物 |
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CN110621667A (zh) | 2017-05-18 | 2019-12-27 | 爱杜西亚药品有限公司 | 嘧啶衍生物 |
WO2018210994A1 (fr) | 2017-05-18 | 2018-11-22 | Idorsia Pharmaceuticals Ltd | Dérivés de phényle utilisés en tant que modulateurs des récepteurs des pge2 |
RS62441B1 (sr) | 2017-05-18 | 2021-11-30 | Idorsia Pharmaceuticals Ltd | N-supstituisani derivati indola |
EP3625228B1 (fr) | 2017-05-18 | 2021-07-07 | Idorsia Pharmaceuticals Ltd | Dérivés de pyrimidine utilisés en tant que modulateurs des récepteurs des pge2 |
CN110621671A (zh) | 2017-05-18 | 2019-12-27 | 爱杜西亚药品有限公司 | 作为pge2受体调节剂的苯并呋喃及苯并噻吩衍生物 |
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CN111315363B (zh) | 2017-09-22 | 2022-10-11 | 奥迪托皮克股份有限公司 | 含有硬脂酸镁的干粉组合物 |
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PL4038052T3 (pl) * | 2019-10-02 | 2024-08-26 | Domain Therapeutics | Antagoniści receptora ep4 prostaglandyny e2 (pge2) |
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TW202228674A (zh) | 2020-11-13 | 2022-08-01 | 日商小野藥品工業股份有限公司 | 藉由併用ep4拮抗藥與免疫檢查點抑制物質而進行之癌症治療 |
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