MX2011011800A - Derivados de carboxamida y urea aromaticas sustituidas como ligandos del receptor de vanilloides. - Google Patents
Derivados de carboxamida y urea aromaticas sustituidas como ligandos del receptor de vanilloides.Info
- Publication number
- MX2011011800A MX2011011800A MX2011011800A MX2011011800A MX2011011800A MX 2011011800 A MX2011011800 A MX 2011011800A MX 2011011800 A MX2011011800 A MX 2011011800A MX 2011011800 A MX2011011800 A MX 2011011800A MX 2011011800 A MX2011011800 A MX 2011011800A
- Authority
- MX
- Mexico
- Prior art keywords
- methyl
- alkyl
- pyrazol
- chlorophenyl
- trifluoromethyl
- Prior art date
Links
- -1 aromatic carboxamide Chemical class 0.000 title claims abstract description 387
- 150000003672 ureas Chemical class 0.000 title abstract description 5
- 108010062740 TRPV Cation Channels Proteins 0.000 title description 13
- 102000011040 TRPV Cation Channels Human genes 0.000 title description 12
- 239000003446 ligand Substances 0.000 title description 2
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- 238000000034 method Methods 0.000 claims abstract description 63
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- 125000001424 substituent group Chemical group 0.000 claims description 228
- 229910052801 chlorine Inorganic materials 0.000 claims description 211
- 229910052794 bromium Inorganic materials 0.000 claims description 210
- 229910052731 fluorine Inorganic materials 0.000 claims description 206
- 229910052740 iodine Inorganic materials 0.000 claims description 181
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 176
- 229920006395 saturated elastomer Polymers 0.000 claims description 135
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 119
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 92
- 125000003118 aryl group Chemical group 0.000 claims description 90
- 125000001072 heteroaryl group Chemical group 0.000 claims description 83
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 81
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 77
- 125000000623 heterocyclic group Chemical group 0.000 claims description 74
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- 125000004076 pyridyl group Chemical group 0.000 claims description 55
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- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims description 50
- 229910052799 carbon Inorganic materials 0.000 claims description 46
- 239000003814 drug Substances 0.000 claims description 46
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 44
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 44
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 43
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- GMAWQTHVIIUMFA-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenoxy)acetyl]-n-(2-sulfanylethyl)piperidine-4-carboxamide Chemical compound C1CC(C(=O)NCCS)CCN1C(=O)COC1=CC=C(Cl)C=C1Cl GMAWQTHVIIUMFA-UHFFFAOYSA-N 0.000 claims description 36
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 36
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
- 125000001544 thienyl group Chemical group 0.000 claims description 32
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 30
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- 229910052720 vanadium Inorganic materials 0.000 claims description 15
- 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 claims description 14
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
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- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- RLWGDRLXZSLGHV-UHFFFAOYSA-N 1-[[4-(2-aminoethoxy)-3-methoxyphenyl]methyl]-3-[(4-tert-butylphenyl)methyl]urea Chemical compound C1=C(OCCN)C(OC)=CC(CNC(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1 RLWGDRLXZSLGHV-UHFFFAOYSA-N 0.000 claims description 5
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- UEQOPMXBUSHMFR-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-(2,3-dihydro-1h-inden-5-yl)urea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C=C3CCCC3=CC=2)N1C1=CC=CC(Cl)=C1 UEQOPMXBUSHMFR-UHFFFAOYSA-N 0.000 claims description 2
- HXGIGQBRICUXJO-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-3-(5,6,7,8-tetrahydronaphthalen-1-yl)urea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C=3CCCCC=3C=CC=2)N1C1=CC=CC(Cl)=C1 HXGIGQBRICUXJO-UHFFFAOYSA-N 0.000 claims description 2
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- JMRCTLVRZKFVPF-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(3-fluorophenyl)pyrazol-3-yl]methyl]-3-(2,3-dihydro-1h-inden-5-yl)urea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C=C3CCCC3=CC=2)N1C1=CC=CC(F)=C1 JMRCTLVRZKFVPF-UHFFFAOYSA-N 0.000 claims description 2
- JVSALHACHKWOQW-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-n-[[2-(3-chlorophenyl)-5-cyclopropyl-1,2,4-triazol-3-yl]methyl]propanamide Chemical compound C=1C=C2OCOC2=CC=1C(C)C(=O)NCC1=NC(C2CC2)=NN1C1=CC=CC(Cl)=C1 JVSALHACHKWOQW-UHFFFAOYSA-N 0.000 claims description 2
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- BRSXXBWUFHCGGP-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-n-[[5-tert-butyl-2-(3-chlorophenyl)-1,2,4-triazol-3-yl]methyl]propanamide Chemical compound C=1C=C2OCOC2=CC=1C(C)C(=O)NCC1=NC(C(C)(C)C)=NN1C1=CC=CC(Cl)=C1 BRSXXBWUFHCGGP-UHFFFAOYSA-N 0.000 claims description 2
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- YNGPAGZWVABOFS-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-n-[[5-tert-butyl-2-(dipropylamino)pyrazol-3-yl]methyl]propanamide Chemical compound CCCN(CCC)N1N=C(C(C)(C)C)C=C1CNC(=O)C(C)C1=CC=C(OCO2)C2=C1 YNGPAGZWVABOFS-UHFFFAOYSA-N 0.000 claims description 2
- FCMJKVVDUQLKIW-UHFFFAOYSA-N 2-(1h-indol-5-yl)-n-[[2-piperidin-1-yl-5-(trifluoromethyl)pyrazol-3-yl]methyl]propanamide Chemical compound C=1C=C2NC=CC2=CC=1C(C)C(=O)NCC1=CC(C(F)(F)F)=NN1N1CCCCC1 FCMJKVVDUQLKIW-UHFFFAOYSA-N 0.000 claims description 2
- NFSOZGLINZBUJQ-UHFFFAOYSA-N 2-(1h-indol-5-yl)-n-[[2-pyridin-2-yloxy-5-(trifluoromethyl)pyrazol-3-yl]methyl]propanamide Chemical compound C=1C=C2NC=CC2=CC=1C(C)C(=O)NCC1=CC(C(F)(F)F)=NN1OC1=CC=CC=N1 NFSOZGLINZBUJQ-UHFFFAOYSA-N 0.000 claims description 2
- VSBHPXBSNIIKKL-UHFFFAOYSA-N 2-(1h-indol-5-yl)-n-[[2-pyridin-4-yloxy-5-(trifluoromethyl)pyrazol-3-yl]methyl]propanamide Chemical compound C=1C=C2NC=CC2=CC=1C(C)C(=O)NCC1=CC(C(F)(F)F)=NN1OC1=CC=NC=C1 VSBHPXBSNIIKKL-UHFFFAOYSA-N 0.000 claims description 2
- SVHWADJUAQEVCH-UHFFFAOYSA-N 2-(2h-benzotriazol-4-yl)-n-[[2-(dipropylamino)-5-(trifluoromethyl)pyrazol-3-yl]methyl]propanamide Chemical compound CCCN(CCC)N1N=C(C(F)(F)F)C=C1CNC(=O)C(C)C1=CC=CC2=C1N=NN2 SVHWADJUAQEVCH-UHFFFAOYSA-N 0.000 claims description 2
- FTWIYSVMIFENFJ-UHFFFAOYSA-N 2-isoquinolin-5-yl-n-[[2-piperidin-1-yl-5-(trifluoromethyl)pyrazol-3-yl]methyl]propanamide Chemical compound C=1C=CC2=CN=CC=C2C=1C(C)C(=O)NCC1=CC(C(F)(F)F)=NN1N1CCCCC1 FTWIYSVMIFENFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
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- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
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- KYORJAZPIUMTQB-UHFFFAOYSA-N n-[[2-(dipropylamino)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-2-(6-hydroxynaphthalen-2-yl)propanamide Chemical compound CCCN(CCC)N1N=C(C(F)(F)F)C=C1CNC(=O)C(C)C1=CC=C(C=C(O)C=C2)C2=C1 KYORJAZPIUMTQB-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
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- OAHCPDZXYXNRSR-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-5-yl)-3-[[5-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]methyl]urea Chemical compound N1=C(C(F)(F)F)C=C(CNC(=O)NC=2C=C3CCCC3=CC=2)N1C1=CC=C(C(F)(F)F)C=C1 OAHCPDZXYXNRSR-UHFFFAOYSA-N 0.000 claims 1
- COOVGMXLFDILNP-UHFFFAOYSA-N 1-[(5-tert-butyl-2-pyridin-2-ylpyrazol-3-yl)methyl]-3-(6-fluoro-1h-indazol-4-yl)urea Chemical compound N1=C(C(C)(C)C)C=C(CNC(=O)NC=2C=3C=NNC=3C=C(F)C=2)N1C1=CC=CC=N1 COOVGMXLFDILNP-UHFFFAOYSA-N 0.000 claims 1
- MTBOHROPUSRDDI-UHFFFAOYSA-N 1-[[2-(3-chlorophenyl)-4-methyl-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(1h-indazol-4-yl)urea Chemical compound N1=C(C(F)(F)F)C(C)=C(CNC(=O)NC=2C=3C=NNC=3C=CC=2)N1C1=CC=CC(Cl)=C1 MTBOHROPUSRDDI-UHFFFAOYSA-N 0.000 claims 1
- AOWPKXONDPZDBU-UHFFFAOYSA-N 1-[[2-cyclohexylsulfanyl-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(1h-indazol-4-yl)urea Chemical compound N1=C(C(F)(F)F)C=C(CNC(=O)NC=2C=3C=NNC=3C=CC=2)N1SC1CCCCC1 AOWPKXONDPZDBU-UHFFFAOYSA-N 0.000 claims 1
- WIBYBAJKSDPGEY-UHFFFAOYSA-N 1-[[2-cyclohexylsulfanyl-5-(trifluoromethyl)pyrazol-3-yl]methyl]-3-(7-hydroxynaphthalen-1-yl)urea Chemical compound C12=CC(O)=CC=C2C=CC=C1NC(=O)NCC1=CC(C(F)(F)F)=NN1SC1CCCCC1 WIBYBAJKSDPGEY-UHFFFAOYSA-N 0.000 claims 1
- LUBCKCSIZNBBRJ-UHFFFAOYSA-N 1-[[5-tert-butyl-2-(6-chloropyridin-2-yl)pyrazol-3-yl]methyl]-3-(1-methylisoquinolin-5-yl)urea Chemical compound C1=CC=C2C(C)=NC=CC2=C1NC(=O)NCC1=CC(C(C)(C)C)=NN1C1=CC=CC(Cl)=N1 LUBCKCSIZNBBRJ-UHFFFAOYSA-N 0.000 claims 1
- CSUGQXMRKOKBFI-UHFFFAOYSA-N 1-methylindazole Chemical compound C1=CC=C2N(C)N=CC2=C1 CSUGQXMRKOKBFI-UHFFFAOYSA-N 0.000 claims 1
- ISUVDXQUJIMXAH-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-n-[[2-[(4-fluorophenyl)methylsulfonyl-methylamino]-5-(trifluoromethyl)pyrazol-3-yl]methyl]propanamide Chemical compound C=1C=C2OCOC2=CC=1C(C)C(=O)NCC1=CC(C(F)(F)F)=NN1N(C)S(=O)(=O)CC1=CC=C(F)C=C1 ISUVDXQUJIMXAH-UHFFFAOYSA-N 0.000 claims 1
- DLQOKEXZRNCYKR-UHFFFAOYSA-N 2-(1h-indol-5-yl)-n-[[2-pyridin-2-yl-5-(trifluoromethyl)pyrazol-3-yl]methyl]propanamide Chemical compound C=1C=C2NC=CC2=CC=1C(C)C(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC=N1 DLQOKEXZRNCYKR-UHFFFAOYSA-N 0.000 claims 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- NVLHWERPPFCSFI-UHFFFAOYSA-N C1=CC(=CC(=C1)Cl)N2C(=CC(=N2)C(F)(F)F)CNC(=O)N Chemical compound C1=CC(=CC(=C1)Cl)N2C(=CC(=N2)C(F)(F)F)CNC(=O)N NVLHWERPPFCSFI-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- VLTBIKSCTKKEOQ-UHFFFAOYSA-N isoquinolin-5-ylurea Chemical compound N1=CC=C2C(NC(=O)N)=CC=CC2=C1 VLTBIKSCTKKEOQ-UHFFFAOYSA-N 0.000 claims 1
- CVTQKIZBTJHUBN-UHFFFAOYSA-N n-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-2-(2-methyl-1,3-benzothiazol-6-yl)propanamide Chemical compound C=1C=C2N=C(C)SC2=CC=1C(C)C(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(Cl)=C1 CVTQKIZBTJHUBN-UHFFFAOYSA-N 0.000 claims 1
- MNKMZOCBLNXMRE-UHFFFAOYSA-N n-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-2-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)propanamide Chemical compound C=1C=C2OCCNC2=CC=1C(C)C(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(Cl)=C1 MNKMZOCBLNXMRE-UHFFFAOYSA-N 0.000 claims 1
- NFUYWSUKVBVWGH-UHFFFAOYSA-N n-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-2-(3,4-dihydro-2h-1,4-benzoxazin-7-yl)propanamide Chemical compound C=1C=C2NCCOC2=CC=1C(C)C(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(Cl)=C1 NFUYWSUKVBVWGH-UHFFFAOYSA-N 0.000 claims 1
- VGOGPNMPVAELRX-UHFFFAOYSA-N n-[[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]-2-(3-oxo-4h-1,4-benzoxazin-7-yl)propanamide Chemical compound C=1C=C2NC(=O)COC2=CC=1C(C)C(=O)NCC1=CC(C(F)(F)F)=NN1C1=CC=CC(Cl)=C1 VGOGPNMPVAELRX-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
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| WO2009067493A2 (en) * | 2007-11-19 | 2009-05-28 | Envivo Pharmaceuticals, Inc. | 1,3,5 tri-subtituted benzenes for treatment of alzheimer's disease and other disorders |
| US8217064B2 (en) | 2007-12-20 | 2012-07-10 | Envivo Pharmaceuticals, Inc. | Tetrasubstituted benzenes |
| US8946204B2 (en) * | 2009-05-07 | 2015-02-03 | Gruenenthal Gmbh | Substituted phenylureas and phenylamides as vanilloid receptor ligands |
| AR076752A1 (es) * | 2009-05-07 | 2011-07-06 | Gruenenthal Chemie | Fenilureas y fenilamidas sustituidas como ligandos del receptor de vanilloides. |
| CN110269856A (zh) | 2010-03-30 | 2019-09-24 | 维颂公司 | 多取代芳族化合物作为凝血酶的抑制剂 |
| CN103842357A (zh) | 2011-07-26 | 2014-06-04 | 格吕伦塔尔有限公司 | 作为类香草素受体配体的被取代的、含有杂芳环吡唑的羧酰胺和脲衍生物 |
| KR20140049028A (ko) | 2011-07-26 | 2014-04-24 | 그뤼넨탈 게엠베하 | 바닐로이드 수용체 리간드로서의 치환된 바이사이클릭 방향족 카복스아미드 및 우레아 유도체 |
| US9296692B2 (en) * | 2011-09-15 | 2016-03-29 | Taipei Medical University | Use of indolyl and indolinyl hydroxamates for treating heart failure of neuronal injury |
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| KR20140091042A (ko) | 2011-11-09 | 2014-07-18 | 그뤼넨탈 게엠베하 | 바닐로이드 수용체 리간드로서의 ｃｏ－함유 그룹으로 치환된 페닐 모이어티를 갖는 치환된 피라졸릴계 카복스아미드 및 우레아 유도체들 |
| TW201326134A (zh) * | 2011-11-09 | 2013-07-01 | Gruenenthal Gmbh | 以被取代吡唑基甲醯胺及被以一含氮基團取代之含有一苯基基元之尿素衍生物做為類香草素受體之配位體 |
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| CN103889961A (zh) | 2011-11-09 | 2014-06-25 | 格吕伦塔尔有限公司 | 作为辣椒素类似物受体配体的携带被含氧基团取代的苯基的被取代的基于吡唑基的甲酰胺及脲衍生物 |
| KR20150130405A (ko) | 2013-03-15 | 2015-11-23 | 베르선 코포레이션 | 트롬빈의 억제제로서의 할로게노피라졸 |
| RU2678830C2 (ru) | 2013-03-15 | 2019-02-04 | Версеон Корпорейшн | Полизамещенные ароматические соединения в качестве ингибиторов сериновых протеаз |
| CN103787895A (zh) * | 2014-01-23 | 2014-05-14 | 安徽华润涂料有限公司 | 一种4-溴-2-甲基苯胺合成的生产工艺 |
| JP2017528486A (ja) | 2014-09-17 | 2017-09-28 | ヴァーセオン コーポレイション | セリンプロテアーゼ阻害剤としてのピラゾリル置換ピリドン化合物 |
| EP3246309B1 (en) | 2015-01-13 | 2020-01-01 | Nissan Chemical Corporation | Method for treating tin compound in reaction mixture |
| HK1246164A1 (zh) | 2015-02-27 | 2018-09-07 | Verseon Corporation | 作为丝氨酸蛋白酶抑制剂的被取代的吡唑化合物 |
| PT3319959T (pt) | 2015-07-06 | 2021-12-06 | Alkermes Inc | Inibidores hetero-halo de histona desacetilase |
| EP3319968A1 (en) | 2015-07-06 | 2018-05-16 | Rodin Therapeutics, Inc. | Heterobicyclic n-aminophenyl-amides as inhibitors of histone deacetylase |
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| CN109071423A (zh) | 2016-02-09 | 2018-12-21 | 益方生物科技（上海）有限公司 | 吲哚胺-2,3-双加氧酶(ido)抑制剂 |
| EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| CN107805221A (zh) * | 2016-09-09 | 2018-03-16 | 西华大学 | 一种制备1h‑吲唑衍生物的方法 |
| KR102530512B1 (ko) * | 2016-11-03 | 2023-05-08 | 브리스톨-마이어스 스큅 컴퍼니 | Romk 채널 억제제로서 유용한 치환된 비사이클 헤테로시클릭 유도체 |
| CA3049443A1 (en) | 2017-01-11 | 2018-07-19 | Rodin Therapeutics, Inc. | Bicyclic inhibitors of histone deacetylase |
| WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
| JP7152471B2 (ja) | 2017-08-07 | 2022-10-12 | ロダン・セラピューティクス，インコーポレーテッド | ヒストン脱アセチル化酵素の二環阻害剤 |
| CN110627683A (zh) * | 2018-06-25 | 2019-12-31 | 广东东阳光药业有限公司 | 一种茚满酮中间体的制备方法 |
| HUE068289T2 (hu) * | 2019-08-23 | 2024-12-28 | Mochida Pharm Co Ltd | Eljárás heterociklidén-acetamid származékok elõállítására |
| CN112409191A (zh) * | 2019-08-23 | 2021-02-26 | 持田制药株式会社 | 光学活性的氨基醇的制备方法 |
| KR20250166332A (ko) | 2019-08-23 | 2025-11-27 | 모찌다 세이야쿠 가부시끼가이샤 | 헤테로시클리덴아세트아미드 유도체의 제조 방법 |
| WO2021039023A1 (ja) * | 2019-08-23 | 2021-03-04 | 持田製薬株式会社 | ヘテロシクリデンアセトアミド誘導体の製造方法 |
| CN110563693B (zh) * | 2019-09-30 | 2022-10-21 | 苏州弘森药业股份有限公司 | 一种胡椒环制备方法 |
| WO2024012791A1 (de) | 2022-07-11 | 2024-01-18 | Bayer Aktiengesellschaft | Elektrochemische synthese von pyrazolinen und pyrazolen |
| CN115282134B (zh) * | 2022-07-20 | 2023-06-23 | 天津中医药大学 | 辣椒素在制备治疗脆性x染色体综合征的药物中的应用 |
| WO2024224298A1 (ko) * | 2023-04-25 | 2024-10-31 | 제이더블유중외제약 주식회사 | 4-아미노인단의 제조 방법 및 디하이드로인데닐-피라졸로[3,4-b]피리딘 아민 화합물의 제조 방법 |
| CN117304009A (zh) * | 2023-10-10 | 2023-12-29 | 韶远科技（上海)有限公司 | 一种3-氟-4-甲基-8-氧代-5,6,7,8-四氢萘的制备方法 |
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| AR230994A1 (es) | 1981-08-31 | 1984-08-31 | Pfizer | Procedimiento para preparar compuesto de 3'-substituido-5'-(2-amino-4-piridil)-1',2',4'-triazol |
| JPH06157469A (ja) | 1992-11-13 | 1994-06-03 | Ube Ind Ltd | ピラゾールカルボニルウレア誘導体、その製法及び有害生物防除剤 |
| US6455559B1 (en) * | 2001-07-19 | 2002-09-24 | Pharmacia Italia S.P.A. | Phenylacetamido-pyrazole derivatives, process for their preparation and their use as antitumor agents |
| GB0206876D0 (en) * | 2002-03-22 | 2002-05-01 | Merck Sharp & Dohme | Therapeutic agents |
| AU2003220558A1 (en) | 2002-03-27 | 2004-06-03 | Smithkline Beecham Corporation | Amide compounds and methods of using the same |
| WO2005004810A2 (en) | 2003-07-02 | 2005-01-20 | Merck & Co., Inc. | Arylsulfonamide derivatives |
| US20050171172A1 (en) | 2003-11-13 | 2005-08-04 | Ambit Biosciences Corporation | Amide derivatives as PDGFR modulators |
| CA2564325A1 (en) | 2004-04-30 | 2005-11-24 | Bayer Pharmaceuticals Corporation | Substituted pyrazolyl urea derivatives useful in the treatment of cancer |
| DE102005037499A1 (de) * | 2005-08-09 | 2007-02-15 | Merck Patent Gmbh | Pyrazolderivate |
| EP2044053A2 (en) | 2005-12-01 | 2009-04-08 | Bayer Healthcare, LLC | Urea compounds useful in the treatment of cancer |
| US20080021217A1 (en) * | 2006-07-20 | 2008-01-24 | Allen Borchardt | Heterocyclic inhibitors of rho kinase |
| JP2010510202A (ja) * | 2006-11-17 | 2010-04-02 | ファイザー株式会社 | 置換ビシクロカルボキシアミド化合物 |
| TW200833663A (en) | 2006-12-21 | 2008-08-16 | Astrazeneca Ab | Therapeutic agents |
| WO2008137102A2 (en) * | 2007-05-04 | 2008-11-13 | Torreypines Therapeutics, Inc. | Methods of modulating amyloid beta and compounds useful therefor |
| JP2010083763A (ja) * | 2008-09-29 | 2010-04-15 | Mitsui Chemicals Inc | ピラゾール誘導体およびその製造方法、ならびに殺菌剤 |
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- 2010-05-06 AU AU2010244684A patent/AU2010244684B2/en not_active Ceased
- 2010-05-06 JP JP2012508950A patent/JP5767631B2/ja not_active Expired - Fee Related
- 2010-05-06 CA CA2758289A patent/CA2758289A1/en not_active Abandoned
- 2010-05-06 SI SI201030151T patent/SI2427436T1/sl unknown
- 2010-05-06 MX MX2011011800A patent/MX2011011800A/es active IP Right Grant
- 2010-05-06 ES ES10720996T patent/ES2402805T3/es active Active
- 2010-05-06 EP EP10720996A patent/EP2427436B1/en not_active Not-in-force
- 2010-05-06 TW TW099114463A patent/TWI504589B/zh not_active IP Right Cessation
- 2010-05-06 DK DK10720996.7T patent/DK2427436T3/da active
- 2010-05-06 PT PT107209967T patent/PT2427436E/pt unknown
- 2010-05-06 US US12/775,155 patent/US8334315B2/en not_active Expired - Fee Related
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- 2010-05-06 BR BRPI1011192A patent/BRPI1011192A2/pt not_active IP Right Cessation
- 2010-05-06 HR HRP20130128AT patent/HRP20130128T1/hr unknown
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| CA2758289A1 (en) | 2010-11-11 |
| US8334315B2 (en) | 2012-12-18 |
| WO2010127855A1 (en) | 2010-11-11 |
| TWI504589B (zh) | 2015-10-21 |
| DK2427436T3 (da) | 2013-04-02 |
| AU2010244684A1 (en) | 2011-11-03 |
| JP2012526061A (ja) | 2012-10-25 |
| TW201120010A (en) | 2011-06-16 |
| SI2427436T1 (sl) | 2013-04-30 |
| JP5767631B2 (ja) | 2015-08-19 |
| ES2402805T3 (es) | 2013-05-09 |
| AR076753A1 (es) | 2011-07-06 |
| US20110003795A1 (en) | 2011-01-06 |
| AU2010244684B2 (en) | 2014-07-03 |
| PL2427436T3 (pl) | 2013-06-28 |
| PT2427436E (pt) | 2013-03-04 |
| EP2427436B1 (en) | 2013-01-09 |
| EP2427436A1 (en) | 2012-03-14 |
| BRPI1011192A2 (pt) | 2016-03-15 |
| HRP20130128T1 (hr) | 2013-03-31 |
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