EA026396B1 - Бензамиды - Google Patents
Бензамиды Download PDFInfo
- Publication number
- EA026396B1 EA026396B1 EA201590562A EA201590562A EA026396B1 EA 026396 B1 EA026396 B1 EA 026396B1 EA 201590562 A EA201590562 A EA 201590562A EA 201590562 A EA201590562 A EA 201590562A EA 026396 B1 EA026396 B1 EA 026396B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- trifluoromethyl
- benzamide
- chloro
- cyclopropyl
- propyl
- Prior art date
Links
- 229940054066 benzamide antipsychotics Drugs 0.000 title 1
- 150000003936 benzamides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 176
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- -1 homomorpholinyl Chemical group 0.000 claims description 412
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 170
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 136
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 21
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 19
- BLOZAAGZIIIPMK-UHFFFAOYSA-N N-[3-cyclopropyl-2-[6-(difluoromethyl)pyridin-3-yl]propyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCC(CC1CC1)C=1C=NC(=CC=1)C(F)F BLOZAAGZIIIPMK-UHFFFAOYSA-N 0.000 claims description 19
- 208000019022 Mood disease Diseases 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 208000002193 Pain Diseases 0.000 claims description 16
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 16
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 14
- 102000005962 receptors Human genes 0.000 claims description 14
- 108020003175 receptors Proteins 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 208000017194 Affective disease Diseases 0.000 claims description 11
- YYMONMOJCASXKN-UHFFFAOYSA-N N-[3-cyclopropyl-2-[2-(difluoromethyl)pyrimidin-5-yl]propyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCC(CC1CC1)C=1C=NC(=NC=1)C(F)F YYMONMOJCASXKN-UHFFFAOYSA-N 0.000 claims description 11
- GOBCJRHIQNXGJC-UHFFFAOYSA-N N-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCC(CC1CC1)C=1C=NC(=CC=1)C(F)(F)F GOBCJRHIQNXGJC-UHFFFAOYSA-N 0.000 claims description 11
- AVFBMGSYAHMUMA-UHFFFAOYSA-N N-[3-cyclopropyl-2-methyl-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCC(CC1CC1)(C=1C=NC(=NC=1)C(F)(F)F)C AVFBMGSYAHMUMA-UHFFFAOYSA-N 0.000 claims description 11
- 208000012902 Nervous system disease Diseases 0.000 claims description 11
- 102100037602 P2X purinoceptor 7 Human genes 0.000 claims description 11
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 11
- 208000024714 major depressive disease Diseases 0.000 claims description 11
- XARUPNVAKQGBMT-UHFFFAOYSA-N N-[2-(4,4-difluorocyclohexyl)-2-(2-methylpyrimidin-5-yl)ethyl]benzamide Chemical compound FC1(CCC(CC1)C(CNC(C1=CC=CC=C1)=O)C=1C=NC(=NC=1)C)F XARUPNVAKQGBMT-UHFFFAOYSA-N 0.000 claims description 10
- WSZUEYGILCNCNU-UHFFFAOYSA-N N-[2-(oxan-4-yl)-2-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCC(C=1C=NC(=NC=1)C(F)(F)F)C1CCOCC1 WSZUEYGILCNCNU-UHFFFAOYSA-N 0.000 claims description 10
- 101710189965 P2X purinoceptor 7 Proteins 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 230000036407 pain Effects 0.000 claims description 10
- HZHHTXMMAIMLPX-UHFFFAOYSA-N N-[3-cyclopropyl-2-(2-methylpyrimidin-5-yl)propyl]benzamide Chemical compound C1(CC1)CC(CNC(C1=CC=CC=C1)=O)C=1C=NC(=NC=1)C HZHHTXMMAIMLPX-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 230000005764 inhibitory process Effects 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- FGWMUWTXELPQRB-UHFFFAOYSA-N N-[2-(2-methylpyrimidin-5-yl)-2-(oxan-4-yl)ethyl]benzamide Chemical compound CC1=NC=C(C=N1)C(CNC(C1=CC=CC=C1)=O)C1CCOCC1 FGWMUWTXELPQRB-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 230000004054 inflammatory process Effects 0.000 claims description 8
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- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 8
- 208000020925 Bipolar disease Diseases 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 125000002393 azetidinyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 208000004296 neuralgia Diseases 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- FBKABPZMIAVQFA-UHFFFAOYSA-N N-[3-cyclopropyl-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCC(CC1CC1)C=1C=NC(=NC=1)C(F)(F)F FBKABPZMIAVQFA-UHFFFAOYSA-N 0.000 claims description 4
- 206010029333 Neurosis Diseases 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 208000028683 bipolar I disease Diseases 0.000 claims description 4
- 208000025307 bipolar depression Diseases 0.000 claims description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 4
- 208000021722 neuropathic pain Diseases 0.000 claims description 4
- 208000015238 neurotic disease Diseases 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 3
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 208000019906 panic disease Diseases 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- QMDISUZCYCCLBP-UHFFFAOYSA-N C1=CC(OC)=CC=C1C1(CNC(=O)C=2C(=C(C)C=CC=2)C)CCCC1 Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C(=C(C)C=CC=2)C)CCCC1 QMDISUZCYCCLBP-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 208000001640 Fibromyalgia Diseases 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims description 2
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- 208000030963 borderline personality disease Diseases 0.000 claims description 2
- 206010007776 catatonia Diseases 0.000 claims description 2
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 150000002460 imidazoles Chemical group 0.000 claims description 2
- 230000036039 immunity Effects 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 201000003995 melancholia Diseases 0.000 claims description 2
- 229960005181 morphine Drugs 0.000 claims description 2
- 208000024817 paranoid personality disease Diseases 0.000 claims description 2
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- YRGBVHFKBJPVBS-UHFFFAOYSA-N N-[2-phenyl-2-[6-(trifluoromethyl)pyridin-3-yl]ethyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCC(C=1C=NC(=CC=1)C(F)(F)F)C1=CC=CC=C1 YRGBVHFKBJPVBS-UHFFFAOYSA-N 0.000 claims 3
- STCXIRZKWXHTIY-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]-6-fluorobenzamide Chemical compound FC1=CC=CC(Cl)=C1C(=O)NCC(C=1C=NC(=CC=1)C(F)(F)F)CC1CC1 STCXIRZKWXHTIY-UHFFFAOYSA-N 0.000 claims 2
- OJJKSNBGQHOBPX-UHFFFAOYSA-N N-[2-pyridin-4-yl-2-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCC(C=1C=NC(=NC=1)C(F)(F)F)C1=CC=NC=C1 OJJKSNBGQHOBPX-UHFFFAOYSA-N 0.000 claims 2
- KIQGXQAXDPCWDW-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]-3-fluorobenzamide Chemical compound FC1=CC=CC(C(=O)NCC(CC2CC2)C=2C=NC(=CC=2)C(F)(F)F)=C1Cl KIQGXQAXDPCWDW-UHFFFAOYSA-N 0.000 claims 1
- SFZLGHHEORQIDV-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]-5-methylsulfonylbenzamide Chemical compound CS(=O)(=O)C1=CC=C(Cl)C(C(=O)NCC(CC2CC2)C=2C=NC(=CC=2)C(F)(F)F)=C1 SFZLGHHEORQIDV-UHFFFAOYSA-N 0.000 claims 1
- VQMPIFDHXSJHBL-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-methyl-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]-3-fluorobenzamide Chemical compound C1CC1CC(C=1C=NC(=NC=1)C(F)(F)F)(C)CNC(=O)C1=CC=CC(F)=C1Cl VQMPIFDHXSJHBL-UHFFFAOYSA-N 0.000 claims 1
- WJFDKOHMAALCBK-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-methyl-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]benzamide Chemical compound C1CC1CC(C=1C=NC(=NC=1)C(F)(F)F)(C)CNC(=O)C1=CC=CC=C1Cl WJFDKOHMAALCBK-UHFFFAOYSA-N 0.000 claims 1
- NXJOLBQCSCIIRM-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-(6-fluoropyridin-3-yl)cyclohexyl]methyl]-3-fluorobenzamide Chemical compound C1=NC(F)=CC=C1C1(CNC(=O)C=2C(=C(F)C=CC=2)Cl)CCC(F)(F)CC1 NXJOLBQCSCIIRM-UHFFFAOYSA-N 0.000 claims 1
- IMRLUNDQCFIFAG-UHFFFAOYSA-N N-[2-pyridin-4-yl-2-[6-(trifluoromethyl)pyridin-3-yl]ethyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCC(C=1C=NC(=CC=1)C(F)(F)F)C1=CC=NC=C1 IMRLUNDQCFIFAG-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- FIRILMDKPYCHCT-UHFFFAOYSA-N n-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NCC(C=1C=NC(=CC=1)C(F)(F)F)CC1CC1 FIRILMDKPYCHCT-UHFFFAOYSA-N 0.000 claims 1
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- 238000000034 method Methods 0.000 description 426
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- 239000000203 mixture Substances 0.000 description 190
- 239000000243 solution Substances 0.000 description 122
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- 239000011541 reaction mixture Substances 0.000 description 86
- QAOJBHRZQQDFHA-UHFFFAOYSA-N 2,3-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1Cl QAOJBHRZQQDFHA-UHFFFAOYSA-N 0.000 description 82
- 238000004587 chromatography analysis Methods 0.000 description 75
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 65
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- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 52
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- C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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- C07C2601/00—Systems containing only non-condensed rings
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| TW201427947A (zh) | 2012-10-12 | 2014-07-16 | Lundbeck & Co As H | 環狀胺 |
| TWI598325B (zh) * | 2012-10-12 | 2017-09-11 | H 朗德貝克公司 | 苯甲醯胺類 |
| WO2014091415A1 (en) | 2012-12-12 | 2014-06-19 | Actelion Pharmaceuticals Ltd | Indole carboxamide derivatives as p2x7 receptor antagonists |
| AR094053A1 (es) | 2012-12-18 | 2015-07-08 | Actelion Pharmaceuticals Ltd | Derivados de indol carboxamida como antagonistas del receptor p2x₇ |
| US9388197B2 (en) | 2013-01-22 | 2016-07-12 | Actelion Pharmaceuticals Ltd. | Heterocyclic amide derivatives as P2X7 receptor antagonists |
| WO2014115078A1 (en) | 2013-01-22 | 2014-07-31 | Actelion Pharmaceuticals Ltd | Heterocyclic amide derivatives as p2x7 receptor antagonists |
| CN105503787A (zh) * | 2015-12-31 | 2016-04-20 | 阜阳欣奕华材料科技有限公司 | 一种索非布韦中间体的纯化方法 |
| CN106366056B (zh) * | 2016-08-26 | 2018-12-11 | 常州市阳光药业有限公司 | 3-氨甲基四氢呋喃的制备方法 |
| FI3609868T3 (fi) * | 2017-03-13 | 2023-11-22 | Raqualia Pharma Inc | Tetrahydrokinoliinijohdannaisia P2X7-reseptorin antagonisteina |
| PE20251292A1 (es) | 2018-03-08 | 2025-05-14 | Incyte Corp | Compuestos diolicos de aminopirazina como inhibidores de pi3k-gamma |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| WO2020227159A2 (en) | 2019-05-03 | 2020-11-12 | Flagship Pioneering Innovations V, Inc. | Methods of modulating immune activity |
| CN117088876A (zh) * | 2020-10-28 | 2023-11-21 | 杭州阿诺生物医药科技有限公司 | 一种高活性Wnt通路抑制剂化合物 |
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| US3435038A (en) * | 1965-06-01 | 1969-03-25 | Sandoz Ag | 5,6,7,9,10,14b-hexahydroisoquinolo (2,1-d) benzo (1,4) diazepines |
| US6303637B1 (en) * | 1998-10-30 | 2001-10-16 | Merck & Co., Inc. | Heterocyclic potassium channel inhibitors |
| US6632836B1 (en) * | 1998-10-30 | 2003-10-14 | Merck & Co., Inc. | Carbocyclic potassium channel inhibitors |
| SE0003476D0 (sv) * | 2000-09-28 | 2000-09-28 | Astrazeneca Ab | Compounds |
| PA8557501A1 (es) * | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | Benzamida, heteroarilamida y amidas inversas |
| TW200300083A (en) | 2001-11-12 | 2003-05-16 | Pfizer Prod Inc | Benzamide, heteroarylamide and reverse amides |
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| ES2281801T3 (es) * | 2003-05-12 | 2007-10-01 | Pfizer Products Inc. | Inhibidores benzamida del receptor p2x7. |
| CA2539227A1 (en) | 2003-08-08 | 2005-02-17 | Vertex Pharmaceuticals Incorporated | Heteroarylaminosulfonylphenyl derivatives for use as sodium or calcium channel blockers in the treatment of pain |
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| US8431704B2 (en) * | 2008-04-22 | 2013-04-30 | Janssen Pharmaceutica Nv | Quinoline or isoquinoline substituted P2X7 antagonists |
| ES2345527B1 (es) * | 2008-10-08 | 2011-09-08 | Hospital Clinic I Provincial De Barcelona | Sustancias bloqueadoras de los canales kv 1.3 para el tratamiento de enfermedades asociadas a hiperplasia de la intima. |
| JP2013532185A (ja) | 2010-07-12 | 2013-08-15 | ファイザー・リミテッド | 化合物 |
| WO2012118139A1 (ja) * | 2011-03-02 | 2012-09-07 | 国立大学法人東京大学 | 内部寄生虫防除剤 |
| AU2012331284B2 (en) * | 2011-11-02 | 2016-06-30 | Bayer Animal Health Gmbh | Compounds with nematicidal activity |
| MX349802B (es) * | 2011-11-25 | 2017-08-14 | Bayer Ip Gmbh | Uso de aril- y hetarilcarboxamidas como endoparasiticidas. |
| TWI598325B (zh) | 2012-10-12 | 2017-09-11 | H 朗德貝克公司 | 苯甲醯胺類 |
| TW201427947A (zh) * | 2012-10-12 | 2014-07-16 | Lundbeck & Co As H | 環狀胺 |
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