JP2004502674A5 - - Google Patents
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- JP2004502674A5 JP2004502674A5 JP2002507781A JP2002507781A JP2004502674A5 JP 2004502674 A5 JP2004502674 A5 JP 2004502674A5 JP 2002507781 A JP2002507781 A JP 2002507781A JP 2002507781 A JP2002507781 A JP 2002507781A JP 2004502674 A5 JP2004502674 A5 JP 2004502674A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- isopropyl
- pyridyl
- pyrrole
- dichlorophenylthio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000000217 alkyl group Chemical group 0.000 claims 62
- -1 methyloxycarbonyl Chemical group 0.000 claims 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 16
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 241000725303 Human immunodeficiency virus Species 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- ILFIRBGRMCGNOO-UHFFFAOYSA-N 1,1-bis($l^{1}-oxidanyl)ethene Chemical group [O]C([O])=C ILFIRBGRMCGNOO-UHFFFAOYSA-N 0.000 claims 3
- CGHZXFOQSJGMKE-UHFFFAOYSA-N 4-[[2-(3,5-dichlorophenyl)sulfanyl-4-(methoxymethyl)-5-methyl-3-propan-2-ylpyrrol-1-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(COC)=C(C)N1CC1=CC=NC=C1 CGHZXFOQSJGMKE-UHFFFAOYSA-N 0.000 claims 3
- ZKGHJMSPQNUHSU-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-3-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=CN=C1 ZKGHJMSPQNUHSU-UHFFFAOYSA-N 0.000 claims 3
- FNYYHEZFHAUXPH-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-2-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C=C(CO)N1CC1=CC=NC=C1 FNYYHEZFHAUXPH-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- VBYXIATXFWEYOE-UHFFFAOYSA-N 1-[5-(3,5-dichlorophenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]propan-2-ol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CC(O)C)=CN1CC1=CC=NC=C1 VBYXIATXFWEYOE-UHFFFAOYSA-N 0.000 claims 2
- RVXJAYPWEXAJCW-UHFFFAOYSA-N 4-[[2-(3,5-dichlorophenyl)sulfanyl-4,5-dimethyl-3-propan-2-ylpyrrol-1-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(C)=C(C)N1CC1=CC=NC=C1 RVXJAYPWEXAJCW-UHFFFAOYSA-N 0.000 claims 2
- XKFSJQJRYDRRAS-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carbaldehyde Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(C=O)=C(C)N1CC1=CC=NC=C1 XKFSJQJRYDRRAS-UHFFFAOYSA-N 0.000 claims 2
- DAWSCXAALVCTQY-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(N)=O)C(C(C)C)=C1SC1=CC(Cl)=CC(Cl)=C1 DAWSCXAALVCTQY-UHFFFAOYSA-N 0.000 claims 2
- BMXZFHZKHQJVCW-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxylic acid Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(O)=O)C(C(C)C)=C1SC1=CC(Cl)=CC(Cl)=C1 BMXZFHZKHQJVCW-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- WEBRUTUJHUWZPN-UHFFFAOYSA-N [1-(cyclohexylmethyl)-5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-ylpyrrol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1CCCCC1 WEBRUTUJHUWZPN-UHFFFAOYSA-N 0.000 claims 2
- RWYKLZFFVYBQAD-UHFFFAOYSA-N [1-benzyl-5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-ylpyrrol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=CC=C1 RWYKLZFFVYBQAD-UHFFFAOYSA-N 0.000 claims 2
- NNVYGLJOFBQUBO-UHFFFAOYSA-N [2-methyl-4-propan-2-yl-1,5-bis(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=NC=CC=1CC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 NNVYGLJOFBQUBO-UHFFFAOYSA-N 0.000 claims 2
- BKTSAGBCUJXLTR-UHFFFAOYSA-N [2-methyl-4-propan-2-yl-5-propan-2-ylsulfanyl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound CC(C)SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 BKTSAGBCUJXLTR-UHFFFAOYSA-N 0.000 claims 2
- QQOHZSYPNKNGGD-UHFFFAOYSA-N [2-methyl-5-(3-nitrophenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=CC([N+]([O-])=O)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 QQOHZSYPNKNGGD-UHFFFAOYSA-N 0.000 claims 2
- KKGUOCPIQVMCOE-UHFFFAOYSA-N [2-methyl-5-methylsulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound CSC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 KKGUOCPIQVMCOE-UHFFFAOYSA-N 0.000 claims 2
- BIPMUHHCDPZFDD-UHFFFAOYSA-N [2-methyl-5-phenylsulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=CC=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 BIPMUHHCDPZFDD-UHFFFAOYSA-N 0.000 claims 2
- NFCCDFQEHMMNDJ-UHFFFAOYSA-N [4-(3,4-dichlorophenyl)-5-(3,5-dichlorophenyl)sulfanyl-2-methyl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=NC=CC=1CN1C(C)=C(CO)C(C=2C=C(Cl)C(Cl)=CC=2)=C1SC1=CC(Cl)=CC(Cl)=C1 NFCCDFQEHMMNDJ-UHFFFAOYSA-N 0.000 claims 2
- DXNOEFFEXRUKQV-UHFFFAOYSA-N [4-(4-chlorophenyl)-5-(3,5-dichlorophenyl)sulfanyl-2-methyl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=NC=CC=1CN1C(C)=C(CO)C(C=2C=CC(Cl)=CC=2)=C1SC1=CC(Cl)=CC(Cl)=C1 DXNOEFFEXRUKQV-UHFFFAOYSA-N 0.000 claims 2
- NBWTVIWCGQNXPX-UHFFFAOYSA-N [5-(3,5-dichlorophenoxy)-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1OC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 NBWTVIWCGQNXPX-UHFFFAOYSA-N 0.000 claims 2
- YKBHCELMYZVYRK-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1,2-dimethyl-4-propan-2-ylpyrrol-3-yl]methanol Chemical compound OCC1=C(C)N(C)C(SC=2C=C(Cl)C=C(Cl)C=2)=C1C(C)C YKBHCELMYZVYRK-UHFFFAOYSA-N 0.000 claims 2
- NJVGRAQSDIYKSQ-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-2-methyl-4-propan-2-ylpyrrol-3-yl]methanol Chemical compound CCN1C(C)=C(CO)C(C(C)C)=C1SC1=CC(Cl)=CC(Cl)=C1 NJVGRAQSDIYKSQ-UHFFFAOYSA-N 0.000 claims 2
- JTVDNMOWWJSBHU-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-2-(hydroxymethyl)-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(CO)N1CC1=CC=NC=C1 JTVDNMOWWJSBHU-UHFFFAOYSA-N 0.000 claims 2
- NTJNOHWOFUHLMK-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-2-ethyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=NC=CC=1CN1C(CC)=C(CO)C(C(C)C)=C1SC1=CC(Cl)=CC(Cl)=C1 NTJNOHWOFUHLMK-UHFFFAOYSA-N 0.000 claims 2
- SGKJTZQKGHLJGF-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-(4-methylphenyl)-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=NC=CC=1CN1C(C)=C(CO)C(C=2C=CC(C)=CC=2)=C1SC1=CC(Cl)=CC(Cl)=C1 SGKJTZQKGHLJGF-UHFFFAOYSA-N 0.000 claims 2
- HGLXOJRVWUUAKR-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-phenyl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=NC=CC=1CN1C(C)=C(CO)C(C=2C=CC=CC=2)=C1SC1=CC(Cl)=CC(Cl)=C1 HGLXOJRVWUUAKR-UHFFFAOYSA-N 0.000 claims 2
- LXOCSTAMCATDJJ-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-2-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=CC=N1 LXOCSTAMCATDJJ-UHFFFAOYSA-N 0.000 claims 2
- RRDWYNMKASTPOP-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanamine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CN)=C(C)N1CC1=CC=NC=C1 RRDWYNMKASTPOP-UHFFFAOYSA-N 0.000 claims 2
- GRNQWGLQZKJIIO-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 GRNQWGLQZKJIIO-UHFFFAOYSA-N 0.000 claims 2
- YJCFENCRTMKYEX-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-3-methyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrrol-2-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)C(CO)=C(C)C=1CC1=CC=NC=C1 YJCFENCRTMKYEX-UHFFFAOYSA-N 0.000 claims 2
- AMHJEIVVLLXFTI-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-3-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-2-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(C)=C(CO)N1CC1=CC=NC=C1 AMHJEIVVLLXFTI-UHFFFAOYSA-N 0.000 claims 2
- YCZNSHYMCQVRII-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-4-(4-methoxyphenyl)-2-methyl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=C(SC=2C=C(Cl)C=C(Cl)C=2)N(CC=2C=CN=CC=2)C(C)=C1CO YCZNSHYMCQVRII-UHFFFAOYSA-N 0.000 claims 2
- IQXFKQNAMUFNKC-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=CN1CC1=CC=NC=C1 IQXFKQNAMUFNKC-UHFFFAOYSA-N 0.000 claims 2
- SMBIBSZOLMAENG-UHFFFAOYSA-N [5-(3,5-dimethylphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C(C)=CC(C)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 SMBIBSZOLMAENG-UHFFFAOYSA-N 0.000 claims 2
- SUMWWNMGUWJJOZ-UHFFFAOYSA-N [5-(3-chlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 SUMWWNMGUWJJOZ-UHFFFAOYSA-N 0.000 claims 2
- DPFRZEZAQSAVJW-UHFFFAOYSA-N [5-[(3,5-dichlorophenyl)methylamino]-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1CNC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 DPFRZEZAQSAVJW-UHFFFAOYSA-N 0.000 claims 2
- OJLVSALJZYYANA-UHFFFAOYSA-N [5-benzyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=CC=CC=1CC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 OJLVSALJZYYANA-UHFFFAOYSA-N 0.000 claims 2
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- MGOGKPMIZGEGOZ-REOHCLBHSA-N (2s)-2-amino-3-hydroxypropanamide Chemical compound OC[C@H](N)C(N)=O MGOGKPMIZGEGOZ-REOHCLBHSA-N 0.000 claims 1
- VSYUMEHTRWAFIY-UHFFFAOYSA-N 1-[5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]ethane-1,2-diol Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(O)CO)C(C(C)C)=C1SC1=CC(Cl)=CC(Cl)=C1 VSYUMEHTRWAFIY-UHFFFAOYSA-N 0.000 claims 1
- TZUFOVKURPPYOG-UHFFFAOYSA-N 1-[5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]ethanone Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(C)=O)C(C(C)C)=C1SC1=CC(Cl)=CC(Cl)=C1 TZUFOVKURPPYOG-UHFFFAOYSA-N 0.000 claims 1
- UHETYCVGVZTFIO-UHFFFAOYSA-N 1-[5-(3,5-dichlorophenyl)sulfanyl-3-(hydroxymethyl)-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-2-yl]propan-2-ol Chemical compound C=1C=NC=CC=1CN1C(CC(O)C)=C(CO)C(C(C)C)=C1SC1=CC(Cl)=CC(Cl)=C1 UHETYCVGVZTFIO-UHFFFAOYSA-N 0.000 claims 1
- ZKZATDCRNSKMMS-UHFFFAOYSA-N 1-[5-(3-chlorophenyl)sulfanyl-2-(hydroxymethyl)-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]propan-2-ol Chemical compound C=1C=CC(Cl)=CC=1SC1=C(C(C)C)C(CC(O)C)=C(CO)N1CC1=CC=NC=C1 ZKZATDCRNSKMMS-UHFFFAOYSA-N 0.000 claims 1
- GNEDCDOSYXWZDO-UHFFFAOYSA-N 2-iodo-1h-pyrrole Chemical class IC1=CC=CN1 GNEDCDOSYXWZDO-UHFFFAOYSA-N 0.000 claims 1
- ASFDKSDGSHWMLF-UHFFFAOYSA-N 3-[[5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methyl]-1,1-dimethylurea Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CNC(=O)N(C)C)=C(C)N1CC1=CC=NC=C1 ASFDKSDGSHWMLF-UHFFFAOYSA-N 0.000 claims 1
- OMEHUFOPZVQGGP-UHFFFAOYSA-N 3-[[5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methyl]-1-methyl-1-phenylurea Chemical compound CC=1N(CC=2C=CN=CC=2)C(SC=2C=C(Cl)C=C(Cl)C=2)=C(C(C)C)C=1CNC(=O)N(C)C1=CC=CC=C1 OMEHUFOPZVQGGP-UHFFFAOYSA-N 0.000 claims 1
- WBRZNNZMKUURDZ-UHFFFAOYSA-N 3-chloro-5-[5-methyl-3-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-2-yl]sulfanylbenzonitrile Chemical compound C=1C(Cl)=CC(C#N)=CC=1SC1=C(C(C)C)C=C(C)N1CC1=CC=NC=C1 WBRZNNZMKUURDZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- GJORGPKRFKERIK-UHFFFAOYSA-N 4-[5-(3,5-dichlorophenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-2-yl]but-3-en-2-one Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C=C(C=CC(C)=O)N1CC1=CC=NC=C1 GJORGPKRFKERIK-UHFFFAOYSA-N 0.000 claims 1
- UYJLCHZWBYASFB-UHFFFAOYSA-N 4-[[2-(3,5-dichlorophenyl)sulfanyl-4-ethenyl-5-methyl-3-propan-2-ylpyrrol-1-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(C=C)=C(C)N1CC1=CC=NC=C1 UYJLCHZWBYASFB-UHFFFAOYSA-N 0.000 claims 1
- HQGXXMRKOAEBLZ-UHFFFAOYSA-N 4-[[2-(3,5-dichlorophenyl)sulfanyl-5-(ethoxymethyl)-3-propan-2-ylpyrrol-1-yl]methyl]pyridine Chemical compound C=1C=NC=CC=1CN1C(COCC)=CC(C(C)C)=C1SC1=CC(Cl)=CC(Cl)=C1 HQGXXMRKOAEBLZ-UHFFFAOYSA-N 0.000 claims 1
- KXIDILNNRXRASL-UHFFFAOYSA-N 4-[[2-(3,5-dichlorophenyl)sulfanyl-5-(methoxymethyl)-3-propan-2-ylpyrrol-1-yl]methyl]pyridine Chemical compound C=1C=NC=CC=1CN1C(COC)=CC(C(C)C)=C1SC1=CC(Cl)=CC(Cl)=C1 KXIDILNNRXRASL-UHFFFAOYSA-N 0.000 claims 1
- KDDFUQHKASXOGQ-UHFFFAOYSA-N 4-[[2-(3,5-dichlorophenyl)sulfanyl-5-methyl-3-phenylpyrrol-1-yl]methyl]pyridine Chemical compound C=1C=NC=CC=1CN1C(C)=CC(C=2C=CC=CC=2)=C1SC1=CC(Cl)=CC(Cl)=C1 KDDFUQHKASXOGQ-UHFFFAOYSA-N 0.000 claims 1
- OIOFYKBHMYIXQQ-UHFFFAOYSA-N 4-[[2-(3,5-dichlorophenyl)sulfanyl-5-methyl-3-propan-2-ylpyrrol-1-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C=C(C)N1CC1=CC=NC=C1 OIOFYKBHMYIXQQ-UHFFFAOYSA-N 0.000 claims 1
- GVGGAWRZMNKCRT-UHFFFAOYSA-N 4-[[2-(3-bromo-5-chlorophenyl)sulfanyl-5-methyl-3-propan-2-ylpyrrol-1-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Br)=CC=1SC1=C(C(C)C)C=C(C)N1CC1=CC=NC=C1 GVGGAWRZMNKCRT-UHFFFAOYSA-N 0.000 claims 1
- JJZJMWLIUDLISF-UHFFFAOYSA-N 4-[[2-(3-chloro-5-propylphenyl)sulfanyl-5-methyl-3-propan-2-ylpyrrol-1-yl]methyl]pyridine Chemical compound CCCC1=CC(Cl)=CC(SC=2N(C(C)=CC=2C(C)C)CC=2C=CN=CC=2)=C1 JJZJMWLIUDLISF-UHFFFAOYSA-N 0.000 claims 1
- PSWWDBKSAXQBOE-UHFFFAOYSA-N 4-[[2-(3-chlorophenyl)sulfanyl-4-(methoxymethyl)-5-methyl-3-propan-2-ylpyrrol-1-yl]methyl]pyridine Chemical compound C=1C=CC(Cl)=CC=1SC1=C(C(C)C)C(COC)=C(C)N1CC1=CC=NC=C1 PSWWDBKSAXQBOE-UHFFFAOYSA-N 0.000 claims 1
- HJDFVDXLTFBFIE-UHFFFAOYSA-N 4-[[4-(azidomethyl)-2-(3,5-dichlorophenyl)sulfanyl-5-methyl-3-propan-2-ylpyrrol-1-yl]methyl]pyridine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CN=[N+]=[N-])=C(C)N1CC1=CC=NC=C1 HJDFVDXLTFBFIE-UHFFFAOYSA-N 0.000 claims 1
- WANGVNBSLXKJEM-UHFFFAOYSA-N 4-cyclopropyl-5-(3,5-dichlorophenyl)sulfanyl-2-methyl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC=2C=CN=CC=2)C(C)=C(C(N)=O)C=1C1CC1 WANGVNBSLXKJEM-UHFFFAOYSA-N 0.000 claims 1
- GYLKEBXAWHWEAD-UHFFFAOYSA-N 5-(3,5-dibromophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(N)=O)C(C(C)C)=C1SC1=CC(Br)=CC(Br)=C1 GYLKEBXAWHWEAD-UHFFFAOYSA-N 0.000 claims 1
- NJCQGPHKDQXOQE-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-phenyl-1-(pyridin-4-ylmethyl)-n-[(2,4,6-trimethoxyphenyl)methyl]pyrrole-3-carboxamide Chemical compound COC1=CC(OC)=CC(OC)=C1CNC(=O)C(C(=C1SC=2C=C(Cl)C=C(Cl)C=2)C=2C=CC=CC=2)=C(C)N1CC1=CC=NC=C1 NJCQGPHKDQXOQE-UHFFFAOYSA-N 0.000 claims 1
- TVQMJMFEEIQZCI-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-phenyl-1-(pyridin-4-ylmethyl)pyrrole-3-carbonitrile Chemical compound C=1C=NC=CC=1CN1C(C)=C(C#N)C(C=2C=CC=CC=2)=C1SC1=CC(Cl)=CC(Cl)=C1 TVQMJMFEEIQZCI-UHFFFAOYSA-N 0.000 claims 1
- FSJSSNUNXMMQNT-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-phenyl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(N)=O)C(C=2C=CC=CC=2)=C1SC1=CC(Cl)=CC(Cl)=C1 FSJSSNUNXMMQNT-UHFFFAOYSA-N 0.000 claims 1
- KJCDLYUNVHWLTI-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-phenyl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=NC=CC=1CN1C(C)=C(C(O)=O)C(C=2C=CC=CC=2)=C1SC1=CC(Cl)=CC(Cl)=C1 KJCDLYUNVHWLTI-UHFFFAOYSA-N 0.000 claims 1
- PBHQJBDDHVASAJ-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-3-(hydroxymethyl)-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-2-carbaldehyde Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C=O)N1CC1=CC=NC=C1 PBHQJBDDHVASAJ-UHFFFAOYSA-N 0.000 claims 1
- TWLYXEAXIBVZOV-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-2,3-dicarbaldehyde Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(C=O)=C(C=O)N1CC1=CC=NC=C1 TWLYXEAXIBVZOV-UHFFFAOYSA-N 0.000 claims 1
- XOMQXYANSPHQPA-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-2-carbaldehyde Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C=C(C=O)N1CC1=CC=NC=C1 XOMQXYANSPHQPA-UHFFFAOYSA-N 0.000 claims 1
- SSQPPOGYXDBFLR-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-n,2-dimethyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(C(=O)NC)=C(C)N1CC1=CC=NC=C1 SSQPPOGYXDBFLR-UHFFFAOYSA-N 0.000 claims 1
- IAFRKQXVDKCBQJ-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfanyl-n,n,2-trimethyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(=O)N(C)C)C(C(C)C)=C1SC1=CC(Cl)=CC(Cl)=C1 IAFRKQXVDKCBQJ-UHFFFAOYSA-N 0.000 claims 1
- RHCVTKWMOUSDCH-UHFFFAOYSA-N 5-(3,5-dimethoxyphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound COC1=CC(OC)=CC(SC=2N(C(C)=C(C(N)=O)C=2C(C)C)CC=2C=CN=CC=2)=C1 RHCVTKWMOUSDCH-UHFFFAOYSA-N 0.000 claims 1
- URIUWGUGLISJPE-UHFFFAOYSA-N 5-(3-bromo-5-chlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(N)=O)C(C(C)C)=C1SC1=CC(Cl)=CC(Br)=C1 URIUWGUGLISJPE-UHFFFAOYSA-N 0.000 claims 1
- OBISXTAFFOXIBB-UHFFFAOYSA-N 5-(3-chloro-5-ethenylphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(N)=O)C(C(C)C)=C1SC1=CC(Cl)=CC(C=C)=C1 OBISXTAFFOXIBB-UHFFFAOYSA-N 0.000 claims 1
- SSQCTUIJVJDELA-UHFFFAOYSA-N 5-(3-chloro-5-ethylphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound CCC1=CC(Cl)=CC(SC=2N(C(C)=C(C(N)=O)C=2C(C)C)CC=2C=CN=CC=2)=C1 SSQCTUIJVJDELA-UHFFFAOYSA-N 0.000 claims 1
- SEWHXTDZUGAFBW-UHFFFAOYSA-N 5-(3-chloro-5-phenylphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(N)=O)C(C(C)C)=C1SC(C=1)=CC(Cl)=CC=1C1=CC=CC=C1 SEWHXTDZUGAFBW-UHFFFAOYSA-N 0.000 claims 1
- RYPVSWJTCJSRHW-UHFFFAOYSA-N 5-(3-chloro-5-propylphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound CCCC1=CC(Cl)=CC(SC=2N(C(C)=C(C(N)=O)C=2C(C)C)CC=2C=CN=CC=2)=C1 RYPVSWJTCJSRHW-UHFFFAOYSA-N 0.000 claims 1
- IYODVKAEHLOXQV-UHFFFAOYSA-N 5-(3-cyanophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(N)=O)C(C(C)C)=C1SC1=CC=CC(C#N)=C1 IYODVKAEHLOXQV-UHFFFAOYSA-N 0.000 claims 1
- RJILOVFSTQONGB-UHFFFAOYSA-N 5-[3-chloro-5-(hydroxymethyl)phenyl]sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(N)=O)C(C(C)C)=C1SC1=CC(Cl)=CC(CO)=C1 RJILOVFSTQONGB-UHFFFAOYSA-N 0.000 claims 1
- CDNABGYJAQBHLZ-UHFFFAOYSA-N [1-[(5-chloro-1-benzothiophen-3-yl)methyl]-5-(3-chlorophenyl)sulfanyl-2-methyl-4-propan-2-ylpyrrol-3-yl]methanol Chemical compound CC(C)C=1C(CO)=C(C)N(CC=2C3=CC(Cl)=CC=C3SC=2)C=1SC1=CC=CC(Cl)=C1 CDNABGYJAQBHLZ-UHFFFAOYSA-N 0.000 claims 1
- XMRHOXXPURONKD-UHFFFAOYSA-N [1-benzyl-5-(3-chlorophenyl)sulfanyl-2-methyl-4-propan-2-ylpyrrol-3-yl]methanol Chemical compound C=1C=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=CC=C1 XMRHOXXPURONKD-UHFFFAOYSA-N 0.000 claims 1
- ZMOPUIZYNALBBE-UHFFFAOYSA-N [2-[4-(hydroxymethyl)-5-methyl-3-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-2-yl]sulfanylphenyl]methanol Chemical compound C=1C=CC=C(CO)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 ZMOPUIZYNALBBE-UHFFFAOYSA-N 0.000 claims 1
- NQOOBTUSKLFNLE-UHFFFAOYSA-N [2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)-5-(2,4,6-trichlorophenyl)sulfanylpyrrol-3-yl]methanol Chemical compound ClC=1C=C(Cl)C=C(Cl)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 NQOOBTUSKLFNLE-UHFFFAOYSA-N 0.000 claims 1
- SMAZWTLZKPZNJG-UHFFFAOYSA-N [2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)-5-(2,4,6-trimethylphenyl)sulfanylpyrrol-3-yl]methanol Chemical compound CC=1C=C(C)C=C(C)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 SMAZWTLZKPZNJG-UHFFFAOYSA-N 0.000 claims 1
- CSBLWKUHTZIFKF-UHFFFAOYSA-N [2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)-5-(2-pyridin-3-ylphenyl)sulfanylpyrrol-3-yl]methanol Chemical compound C=1C=CC=C(C=2C=NC=CC=2)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 CSBLWKUHTZIFKF-UHFFFAOYSA-N 0.000 claims 1
- WBGJSLFDESEQAP-UHFFFAOYSA-N [2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)-5-[3-(trifluoromethyl)phenyl]sulfanylpyrrol-3-yl]methanol Chemical compound C=1C=CC(C(F)(F)F)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 WBGJSLFDESEQAP-UHFFFAOYSA-N 0.000 claims 1
- LBKRVDUBJWYYKE-UHFFFAOYSA-N [2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)-5-[4-(trifluoromethoxy)phenyl]sulfanylpyrrol-3-yl]methanol Chemical compound C=1C=C(OC(F)(F)F)C=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 LBKRVDUBJWYYKE-UHFFFAOYSA-N 0.000 claims 1
- CTMIKOKQUFLLQL-UHFFFAOYSA-N [2-methyl-5-(2-phenylphenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 CTMIKOKQUFLLQL-UHFFFAOYSA-N 0.000 claims 1
- KRIXHHVXWBKTEG-UHFFFAOYSA-N [2-methyl-5-(3-methylphenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=CC(C)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 KRIXHHVXWBKTEG-UHFFFAOYSA-N 0.000 claims 1
- XQGDTCQIVDKLPN-UHFFFAOYSA-N [2-methyl-5-(3-phenylphenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 XQGDTCQIVDKLPN-UHFFFAOYSA-N 0.000 claims 1
- ZLMCCJAJWRHQQE-UHFFFAOYSA-N [2-methyl-5-(4-methylphenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=C(C)C=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 ZLMCCJAJWRHQQE-UHFFFAOYSA-N 0.000 claims 1
- POAQJHJQFKZXPN-UHFFFAOYSA-N [2-methyl-5-naphthalen-2-ylsulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=C2C=CC=CC2=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 POAQJHJQFKZXPN-UHFFFAOYSA-N 0.000 claims 1
- VWWVSOUEGLCMHV-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 VWWVSOUEGLCMHV-UHFFFAOYSA-N 0.000 claims 1
- ADLDQSZXDXNLMG-UHFFFAOYSA-N [5-(2,4-dimethylphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=C(C)C=C(C)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 ADLDQSZXDXNLMG-UHFFFAOYSA-N 0.000 claims 1
- QBCPJEHXVBRSEX-UHFFFAOYSA-N [5-(2,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C(Cl)=CC=C(Cl)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 QBCPJEHXVBRSEX-UHFFFAOYSA-N 0.000 claims 1
- ZIQDPKKGAHEXQO-UHFFFAOYSA-N [5-(2,5-dimethoxyphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound COC1=CC=C(OC)C(SC=2N(C(C)=C(CO)C=2C(C)C)CC=2C=CN=CC=2)=C1 ZIQDPKKGAHEXQO-UHFFFAOYSA-N 0.000 claims 1
- IFLLMXQCNFWUMG-UHFFFAOYSA-N [5-(2,5-dimethylphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C(C)=CC=C(C)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 IFLLMXQCNFWUMG-UHFFFAOYSA-N 0.000 claims 1
- AMXVPMAWANZAAK-UHFFFAOYSA-N [5-(2-chloro-4-fluorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=C(F)C=C(Cl)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 AMXVPMAWANZAAK-UHFFFAOYSA-N 0.000 claims 1
- PGHSMWYFLWJAAT-UHFFFAOYSA-N [5-(2-chloro-6-methylphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound CC=1C=CC=C(Cl)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 PGHSMWYFLWJAAT-UHFFFAOYSA-N 0.000 claims 1
- WNMCNWJAIDNXLU-UHFFFAOYSA-N [5-(2-chlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=CC=C(Cl)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 WNMCNWJAIDNXLU-UHFFFAOYSA-N 0.000 claims 1
- GCQLGDDZRYPJPN-UHFFFAOYSA-N [5-(2-fluorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=CC=C(F)C=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 GCQLGDDZRYPJPN-UHFFFAOYSA-N 0.000 claims 1
- GIQZRGKRLFALQY-UHFFFAOYSA-N [5-(2-methoxyphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound COC1=CC=CC=C1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 GIQZRGKRLFALQY-UHFFFAOYSA-N 0.000 claims 1
- MYKHOJDMKRUGDF-UHFFFAOYSA-N [5-(3,4-dimethoxyphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C1=C(OC)C(OC)=CC=C1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 MYKHOJDMKRUGDF-UHFFFAOYSA-N 0.000 claims 1
- HGOZMMZKQRLAJO-UHFFFAOYSA-N [5-(3,4-dimethylphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=C(C)C(C)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 HGOZMMZKQRLAJO-UHFFFAOYSA-N 0.000 claims 1
- ZNJRRIHFOIBLMG-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-2,4-di(propan-2-yl)-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C(C)C)N1CC1=CC=NC=C1 ZNJRRIHFOIBLMG-UHFFFAOYSA-N 0.000 claims 1
- CZYNOBRIFAMWJI-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methylurea Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CNC(N)=O)=C(C)N1CC1=CC=NC=C1 CZYNOBRIFAMWJI-UHFFFAOYSA-N 0.000 claims 1
- KCZBDRIBHZAZHT-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-2-phenyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=NC=CC=1CN1C(SC=2C=C(Cl)C=C(Cl)C=2)=C(C(C)C)C(CO)=C1C1=CC=CC=C1 KCZBDRIBHZAZHT-UHFFFAOYSA-N 0.000 claims 1
- MNZQRPJEROGNOL-UHFFFAOYSA-N [5-(3-chlorophenyl)sulfanyl-1-[(3-methoxyphenyl)methyl]-2-methyl-4-propan-2-ylpyrrol-3-yl]methanol Chemical compound COC1=CC=CC(CN2C(=C(C(C)C)C(CO)=C2C)SC=2C=C(Cl)C=CC=2)=C1 MNZQRPJEROGNOL-UHFFFAOYSA-N 0.000 claims 1
- KFOZMYPRIAPXBU-UHFFFAOYSA-N [5-(3-chlorophenyl)sulfanyl-1-[(4-methoxyphenyl)methyl]-2-methyl-4-propan-2-ylpyrrol-3-yl]methanol Chemical compound C1=CC(OC)=CC=C1CN1C(SC=2C=C(Cl)C=CC=2)=C(C(C)C)C(CO)=C1C KFOZMYPRIAPXBU-UHFFFAOYSA-N 0.000 claims 1
- YMVCEAPMPDUMJE-UHFFFAOYSA-N [5-(3-chlorophenyl)sulfanyl-1-[[4-chloro-2-(trifluoromethyl)quinolin-6-yl]methyl]-2-methyl-4-propan-2-ylpyrrol-3-yl]methanol Chemical compound CC(C)C=1C(CO)=C(C)N(CC=2C=C3C(Cl)=CC(=NC3=CC=2)C(F)(F)F)C=1SC1=CC=CC(Cl)=C1 YMVCEAPMPDUMJE-UHFFFAOYSA-N 0.000 claims 1
- NBUHXLOUSXQREK-UHFFFAOYSA-N [5-(3-chlorophenyl)sulfanyl-2,4-di(propan-2-yl)-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C(C)C)N1CC1=CC=NC=C1 NBUHXLOUSXQREK-UHFFFAOYSA-N 0.000 claims 1
- NOKQCBUKJRTBRY-UHFFFAOYSA-N [5-(3-chlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(1,3-thiazol-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CSC=N1 NOKQCBUKJRTBRY-UHFFFAOYSA-N 0.000 claims 1
- XDOUQOXQEAMPOZ-UHFFFAOYSA-N [5-(3-chlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(quinolin-2-ylmethyl)pyrrol-3-yl]methanol Chemical compound CC(C)C=1C(CO)=C(C)N(CC=2N=C3C=CC=CC3=CC=2)C=1SC1=CC=CC(Cl)=C1 XDOUQOXQEAMPOZ-UHFFFAOYSA-N 0.000 claims 1
- LOHNPBWEZPLJFU-UHFFFAOYSA-N [5-(3-chlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-[[6-(trifluoromethyl)pyridin-3-yl]methyl]pyrrol-3-yl]methanol Chemical compound C=1C=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=C(C(F)(F)F)N=C1 LOHNPBWEZPLJFU-UHFFFAOYSA-N 0.000 claims 1
- GODGHCDHDGVVCY-UHFFFAOYSA-N [5-(3-fluorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C=1C=CC(F)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 GODGHCDHDGVVCY-UHFFFAOYSA-N 0.000 claims 1
- KZMWHEJKBLWVNF-UHFFFAOYSA-N [5-(4-ethylphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C1=CC(CC)=CC=C1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 KZMWHEJKBLWVNF-UHFFFAOYSA-N 0.000 claims 1
- AGOHDWBABPUMCT-UHFFFAOYSA-N [5-(4-methoxyphenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methanol Chemical compound C1=CC(OC)=CC=C1SC1=C(C(C)C)C(CO)=C(C)N1CC1=CC=NC=C1 AGOHDWBABPUMCT-UHFFFAOYSA-N 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- WTKOUCTVXOOXQW-UHFFFAOYSA-N ethyl 2-[5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]-2-hydroxyacetate Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(C(O)C(=O)OCC)=C(C)N1CC1=CC=NC=C1 WTKOUCTVXOOXQW-UHFFFAOYSA-N 0.000 claims 1
- NHRYXUAOTWGULV-UHFFFAOYSA-N ethyl 2-[5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]-2-oxoacetate Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(C(=O)C(=O)OCC)=C(C)N1CC1=CC=NC=C1 NHRYXUAOTWGULV-UHFFFAOYSA-N 0.000 claims 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 1
- 239000012336 iodinating agent Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- AJVVSYQESRHMEP-UHFFFAOYSA-N n-[[5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methyl]-2-pyridin-4-ylacetamide Chemical compound CC=1N(CC=2C=CN=CC=2)C(SC=2C=C(Cl)C=C(Cl)C=2)=C(C(C)C)C=1CNC(=O)CC1=CC=NC=C1 AJVVSYQESRHMEP-UHFFFAOYSA-N 0.000 claims 1
- DIMGSFCUWSIEFO-UHFFFAOYSA-N n-[[5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methyl]-4-methylbenzenesulfonamide Chemical compound CC=1N(CC=2C=CN=CC=2)C(SC=2C=C(Cl)C=C(Cl)C=2)=C(C(C)C)C=1CNS(=O)(=O)C1=CC=C(C)C=C1 DIMGSFCUWSIEFO-UHFFFAOYSA-N 0.000 claims 1
- NFZAKPIRQMORAV-UHFFFAOYSA-N n-[[5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methyl]acetamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CNC(C)=O)=C(C)N1CC1=CC=NC=C1 NFZAKPIRQMORAV-UHFFFAOYSA-N 0.000 claims 1
- VLNSMDKZVLXDIM-UHFFFAOYSA-N n-[[5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methyl]benzamide Chemical compound CC=1N(CC=2C=CN=CC=2)C(SC=2C=C(Cl)C=C(Cl)C=2)=C(C(C)C)C=1CNC(=O)C1=CC=CC=C1 VLNSMDKZVLXDIM-UHFFFAOYSA-N 0.000 claims 1
- ZGTRBABHRASKLT-UHFFFAOYSA-N n-[[5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methyl]benzenesulfonamide Chemical compound CC=1N(CC=2C=CN=CC=2)C(SC=2C=C(Cl)C=C(Cl)C=2)=C(C(C)C)C=1CNS(=O)(=O)C1=CC=CC=C1 ZGTRBABHRASKLT-UHFFFAOYSA-N 0.000 claims 1
- CYSOJDVFFFWRGI-UHFFFAOYSA-N n-[[5-(3,5-dichlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrol-3-yl]methyl]methanesulfonamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)C(CNS(C)(=O)=O)=C(C)N1CC1=CC=NC=C1 CYSOJDVFFFWRGI-UHFFFAOYSA-N 0.000 claims 1
- CYTOFGPAVACHLO-UHFFFAOYSA-N n-benzyl-2-[2-(3-chlorophenyl)sulfanyl-4-(hydroxymethyl)-5-methyl-3-propan-2-ylpyrrol-1-yl]acetamide Chemical compound C=1C=CC(Cl)=CC=1SC1=C(C(C)C)C(CO)=C(C)N1CC(=O)NCC1=CC=CC=C1 CYTOFGPAVACHLO-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- CISXNMUCZSWIDW-UHFFFAOYSA-N tert-butyl 5-(3,5-dibromophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxylate Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(=O)OC(C)(C)C)C(C(C)C)=C1SC1=CC(Br)=CC(Br)=C1 CISXNMUCZSWIDW-UHFFFAOYSA-N 0.000 claims 1
- XUJMNBHXKKZDQE-UHFFFAOYSA-N tert-butyl 5-(3-bromo-5-chlorophenyl)sulfanyl-2-methyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxylate Chemical compound C=1C=NC=CC=1CN1C(C)=C(C(=O)OC(C)(C)C)C(C(C)C)=C1SC1=CC(Cl)=CC(Br)=C1 XUJMNBHXKKZDQE-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0016453.3A GB0016453D0 (en) | 2000-07-04 | 2000-07-04 | Pyrrole derivatives |
| PCT/EP2001/004832 WO2002002524A1 (en) | 2000-07-04 | 2001-04-30 | Pyrrole derivatives for treating aids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004502674A JP2004502674A (ja) | 2004-01-29 |
| JP2004502674A5 true JP2004502674A5 (https=) | 2005-02-24 |
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| JP2002507781A Pending JP2004502674A (ja) | 2000-07-04 | 2001-04-30 | エイズを治療するためのピロール誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6737429B2 (https=) |
| EP (1) | EP1301481A1 (https=) |
| JP (1) | JP2004502674A (https=) |
| KR (1) | KR100549884B1 (https=) |
| CN (1) | CN1440385A (https=) |
| AR (1) | AR028602A1 (https=) |
| AU (2) | AU2001263874B2 (https=) |
| BR (1) | BR0112241A (https=) |
| CA (1) | CA2412270A1 (https=) |
| EC (1) | ECSP014109A (https=) |
| GB (1) | GB0016453D0 (https=) |
| GT (1) | GT200100111A (https=) |
| MX (1) | MXPA02012409A (https=) |
| PA (1) | PA8516201A1 (https=) |
| PE (1) | PE20020269A1 (https=) |
| UY (1) | UY26720A1 (https=) |
| WO (1) | WO2002002524A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1405849A1 (en) * | 2002-10-04 | 2004-04-07 | Corning Incorporated | Halogenated styrene compounds and low-absorption-loss polymers obtainable therefrom |
| CA2801848C (en) * | 2003-12-26 | 2015-03-31 | Masatoshi Hagiwara | Methods for controlling sr protein phosphorylation, and antiviral agents whose active ingredients comprise agents that control sr protein activity |
| WO2006036024A1 (ja) | 2004-09-30 | 2006-04-06 | Takeda Pharmaceutical Company Limited | プロトンポンプ阻害薬 |
| TW200628446A (en) * | 2004-12-14 | 2006-08-16 | Takeda Pharmaceuticals Co | Substituted pyrrole derivative |
| CA2592909A1 (en) * | 2005-01-06 | 2006-07-13 | Pfizer Limited | Imidazole derivatives as enzyme reverse transcriptase modulators |
| AU2006285641A1 (en) | 2005-08-30 | 2007-03-08 | Takeda Pharmaceutical Company Limited | 1-heterocyclylsulfonyl, 2-aminomethyl, 5- (hetero-) aryl substituted 1-h-pyrrole derivatives as acid secretion inhibitors |
| US20100113421A1 (en) * | 2006-10-06 | 2010-05-06 | Williams Theresa M | Non-nucleoside reverse transcriptase inhibitors |
| WO2008058287A1 (en) * | 2006-11-10 | 2008-05-15 | Syndax Pharmaceuticals, Inc. | COMBINATION OF ERα+ LIGANDS AND HISTONE DEACETYLASE INHIBITORS FOR THE TREATMENT OF CANCER |
| US8933105B2 (en) | 2007-02-28 | 2015-01-13 | Takeda Pharmaceutical Company Limited | Pyrrole compounds |
| WO2009015180A2 (en) * | 2007-07-23 | 2009-01-29 | Syndax Pharmaceuticals, Inc. | Novel compounds and methods of using them |
| WO2009050977A1 (en) * | 2007-10-16 | 2009-04-23 | Nikon Corporation | Illumination optical system, exposure apparatus, and device manufacturing method |
| WO2009067453A1 (en) * | 2007-11-19 | 2009-05-28 | Syndax Pharmaceuticals, Inc. | Combinations of hdac inhibitors and proteasome inhibitors |
| RS52872B (sr) | 2008-08-27 | 2013-12-31 | Takeda Pharmaceutical Company Limited | Jedinjenja pirola |
| GB0823001D0 (en) * | 2008-12-17 | 2009-01-28 | Syngenta Participations Ag | Thiophene,furan and pyrrole derivatives with plant growth regulating properties |
| CN101775011B (zh) * | 2009-01-13 | 2013-07-31 | 中国人民解放军军事医学科学院毒物药物研究所 | N-取代苯基-3-甲烯杂环芳烃-2,5-二甲基吡咯类化合物及其抗hiv/aids的应用 |
| WO2021102114A1 (en) * | 2019-11-19 | 2021-05-27 | New York Blood Center, Inc. | Substituted heterocyclics with therapeutic activity in hiv |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3644631A (en) * | 1969-05-13 | 1972-02-22 | Endo Lab | Therapeutic methods utilizing aryl pyrrol-3-yl ketones |
| US4282242A (en) * | 1980-03-07 | 1981-08-04 | Pfizer Inc. | Antidiabetic pyrrolecarboxylic acids |
| US4347186A (en) * | 1980-10-20 | 1982-08-31 | Syntex (U.S.A.) Inc. | Process for preparing 5-aroyl 1,2-dihydro-3-H pyrrolo[1,2-a]pyrrole-1-carboxylic acids and novel intermediates therein |
| KR100190730B1 (ko) * | 1992-12-17 | 1999-06-01 | 디. 제이. 우드, 스피겔 알렌 제이 | 부신피질 호르몬 유리인자(crf) 길항물질로서 치환된 피라졸 |
| AU2265495A (en) * | 1994-06-06 | 1996-01-04 | Pfizer Inc. | Substituted pyrazoles having corticotropin-releasing factor (crf) antagonist activity |
| TW406075B (en) * | 1994-12-13 | 2000-09-21 | Upjohn Co | Alkyl substituted piperidinyl and piperazinyl anti-AIDS compounds |
| BR9710352A (pt) * | 1996-07-11 | 1999-08-17 | Pfizer | Compostos piridilpirrole |
| DE19963174A1 (de) * | 1999-12-27 | 2001-07-12 | Gruenenthal Gmbh | Substituierte Pyrrol-Mannichbasen |
-
2000
- 2000-07-04 GB GBGB0016453.3A patent/GB0016453D0/en not_active Ceased
-
2001
- 2001-04-30 MX MXPA02012409A patent/MXPA02012409A/es active IP Right Grant
- 2001-04-30 CA CA002412270A patent/CA2412270A1/en not_active Abandoned
- 2001-04-30 CN CN01812290A patent/CN1440385A/zh active Pending
- 2001-04-30 WO PCT/EP2001/004832 patent/WO2002002524A1/en not_active Ceased
- 2001-04-30 KR KR1020037000138A patent/KR100549884B1/ko not_active Expired - Fee Related
- 2001-04-30 EP EP01938137A patent/EP1301481A1/en not_active Withdrawn
- 2001-04-30 JP JP2002507781A patent/JP2004502674A/ja active Pending
- 2001-04-30 AU AU2001263874A patent/AU2001263874B2/en not_active Ceased
- 2001-04-30 BR BR0112241-0A patent/BR0112241A/pt not_active IP Right Cessation
- 2001-04-30 AU AU6387401A patent/AU6387401A/xx active Pending
- 2001-05-04 PA PA20018516201A patent/PA8516201A1/es unknown
- 2001-05-18 UY UY26720A patent/UY26720A1/es not_active Application Discontinuation
- 2001-05-22 AR ARP010102414A patent/AR028602A1/es not_active Application Discontinuation
- 2001-05-25 PE PE2001000487A patent/PE20020269A1/es not_active Application Discontinuation
- 2001-06-12 GT GT200100111A patent/GT200100111A/es unknown
- 2001-06-13 US US09/880,534 patent/US6737429B2/en not_active Expired - Fee Related
- 2001-07-04 EC EC2001004109A patent/ECSP014109A/es unknown
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