HRP20050347A2 - Pyrrole derivatives as antimycobacterial compounds - Google Patents
Pyrrole derivatives as antimycobacterial compounds Download PDFInfo
- Publication number
- HRP20050347A2 HRP20050347A2 HR20050347A HRP20050347A HRP20050347A2 HR P20050347 A2 HRP20050347 A2 HR P20050347A2 HR 20050347 A HR20050347 A HR 20050347A HR P20050347 A HRP20050347 A HR P20050347A HR P20050347 A2 HRP20050347 A2 HR P20050347A2
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- chlorophenyl
- unsubstituted
- phenyl
- piperazine
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 114
- 230000001355 anti-mycobacterial effect Effects 0.000 title claims abstract description 10
- 239000003926 antimycobacterial agent Substances 0.000 title claims description 5
- 150000003233 pyrroles Chemical class 0.000 title abstract description 11
- 201000008827 tuberculosis Diseases 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
- -1 diastereomers Chemical class 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 35
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 30
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 21
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
- 125000004193 piperazinyl group Chemical group 0.000 claims description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- 125000005309 thioalkoxy group Chemical group 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
- 150000001204 N-oxides Chemical class 0.000 claims description 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 150000004885 piperazines Chemical class 0.000 claims description 10
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical class C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 10
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 150000002790 naphthalenes Chemical class 0.000 claims description 6
- 150000003222 pyridines Chemical class 0.000 claims description 6
- 150000004867 thiadiazoles Chemical class 0.000 claims description 6
- 150000003557 thiazoles Chemical class 0.000 claims description 6
- BSJZQLWPHJZQIF-UHFFFAOYSA-N 1-[[1,5-bis(4-chlorophenyl)-2-ethylpyrrol-3-yl]methyl]-4-[3-(trifluoromethyl)phenyl]piperazine Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N(C=2C=CC(Cl)=CC=2)C(CC)=C1CN(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 BSJZQLWPHJZQIF-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- PRXZOPNJRFEGRH-UHFFFAOYSA-N n-[2-methyl-5-phenyl-3-[[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]pyrrol-1-yl]pyridine-4-carboxamide Chemical compound C1=C(C=2C=CC=CC=2)N(NC(=O)C=2C=CN=CC=2)C(C)=C1CN(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 PRXZOPNJRFEGRH-UHFFFAOYSA-N 0.000 claims description 5
- SCMWMRWBHUWBCO-UHFFFAOYSA-N n-[5-methyl-2-phenyl-3-[[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]pyrrol-1-yl]pyridine-4-carboxamide Chemical compound C=1C=CC=CC=1C=1N(NC(=O)C=2C=CN=CC=2)C(C)=CC=1CN(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 SCMWMRWBHUWBCO-UHFFFAOYSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- IWYWFPBHXCCNKX-UHFFFAOYSA-N 1-[[1,5-bis(4-chlorophenyl)-2-methylpyrrol-3-yl]methyl]-4-[3-(trifluoromethyl)phenyl]piperazine Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N(C=2C=CC(Cl)=CC=2)C(C)=C1CN(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 IWYWFPBHXCCNKX-UHFFFAOYSA-N 0.000 claims description 4
- CGGOMLUIWQEKRR-UHFFFAOYSA-N 1-[[1-(2,4-difluorophenyl)-2-methyl-5-phenylpyrrol-3-yl]methyl]-4-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CC2=C(N(C(C=3C=CC=CC=3)=C2)C=2C(=CC(F)=CC=2)F)C)CC1 CGGOMLUIWQEKRR-UHFFFAOYSA-N 0.000 claims description 4
- PUHBVPHFGWBLSO-UHFFFAOYSA-N 1-[[1-(2,4-difluorophenyl)-2-methyl-5-phenylpyrrol-3-yl]methyl]-4-(4-fluorophenyl)piperazine Chemical compound C1=C(C=2C=CC=CC=2)N(C=2C(=CC(F)=CC=2)F)C(C)=C1CN(CC1)CCN1C1=CC=C(F)C=C1 PUHBVPHFGWBLSO-UHFFFAOYSA-N 0.000 claims description 4
- FMBMNBXRNREQGN-UHFFFAOYSA-N 1-[[1-(2,4-difluorophenyl)-2-methyl-5-phenylpyrrol-3-yl]methyl]-4-[3-(trifluoromethyl)phenyl]piperazine Chemical compound C1=C(C=2C=CC=CC=2)N(C=2C(=CC(F)=CC=2)F)C(C)=C1CN(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 FMBMNBXRNREQGN-UHFFFAOYSA-N 0.000 claims description 4
- CQSOPQMQLDMUDX-UHFFFAOYSA-N 1-[[1-(2,4-difluorophenyl)-2-methyl-5-phenylpyrrol-3-yl]methyl]-4-pyridin-2-ylpiperazine Chemical compound C1=C(C=2C=CC=CC=2)N(C=2C(=CC(F)=CC=2)F)C(C)=C1CN(CC1)CCN1C1=CC=CC=N1 CQSOPQMQLDMUDX-UHFFFAOYSA-N 0.000 claims description 4
- QVFBJCLKXVFMHR-UHFFFAOYSA-N 1-[[5-(4-chlorophenyl)-1-(2,4-difluorophenyl)-2-methylpyrrol-3-yl]methyl]-4-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CC2=C(N(C(C=3C=CC(Cl)=CC=3)=C2)C=2C(=CC(F)=CC=2)F)C)CC1 QVFBJCLKXVFMHR-UHFFFAOYSA-N 0.000 claims description 4
- GAQWPYVKXHMVQS-UHFFFAOYSA-N 1-[[5-(4-chlorophenyl)-1-(2,4-difluorophenyl)-2-methylpyrrol-3-yl]methyl]-4-(4-fluorophenyl)piperazine Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N(C=2C(=CC(F)=CC=2)F)C(C)=C1CN(CC1)CCN1C1=CC=C(F)C=C1 GAQWPYVKXHMVQS-UHFFFAOYSA-N 0.000 claims description 4
- IXPFEKSWZQNWEM-UHFFFAOYSA-N 1-[[5-(4-chlorophenyl)-1-(2,4-difluorophenyl)-2-methylpyrrol-3-yl]methyl]-4-[3-(trifluoromethyl)phenyl]piperazine Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N(C=2C(=CC(F)=CC=2)F)C(C)=C1CN(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 IXPFEKSWZQNWEM-UHFFFAOYSA-N 0.000 claims description 4
- HIMLAGVZEBQJNZ-UHFFFAOYSA-N 1-[[5-(4-chlorophenyl)-1-(2,4-difluorophenyl)-2-methylpyrrol-3-yl]methyl]-4-pyridin-2-ylpiperazine Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N(C=2C(=CC(F)=CC=2)F)C(C)=C1CN(CC1)CCN1C1=CC=CC=N1 HIMLAGVZEBQJNZ-UHFFFAOYSA-N 0.000 claims description 4
- LVGOMVNGPXTWNP-UHFFFAOYSA-N 1-benzhydryl-4-[[2-(4-chlorophenyl)-1-(2,4-difluorophenyl)-5-methylpyrrol-3-yl]methyl]piperazine Chemical compound C=1C=C(Cl)C=CC=1C=1N(C=2C(=CC(F)=CC=2)F)C(C)=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 LVGOMVNGPXTWNP-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- SWWPJWXRYWRKKD-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-5-methyl-2-phenyl-4-[(4-pyridin-2-ylpiperazin-1-yl)methyl]pyrrol-3-yl]pyrazine-2-carboxamide Chemical compound C1CN(C=2N=CC=CC=2)CCN1CC=1C(C)=NC(C=2C=CC(Cl)=CC=2)(C=2C=CC=CC=2)C=1NC(=O)C1=CN=CC=N1 SWWPJWXRYWRKKD-UHFFFAOYSA-N 0.000 claims description 4
- HQDKNUGBUQQGRA-UHFFFAOYSA-N n-[5-(4-chlorophenyl)-2-methyl-4-[[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-1h-pyrrol-3-yl]pyrazine-2-carboxamide Chemical compound C=1N=CC=NC=1C(=O)NC1=C(C)NC(C=2C=CC(Cl)=CC=2)=C1CN(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 HQDKNUGBUQQGRA-UHFFFAOYSA-N 0.000 claims description 4
- DNPORLUGJKDTNF-UHFFFAOYSA-N n-[5-(4-chlorophenyl)-4-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-2-methyl-1h-pyrrol-3-yl]pyrazine-2-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CC2=C(NC(C)=C2NC(=O)C=2N=CC=NC=2)C=2C=CC(Cl)=CC=2)CC1 DNPORLUGJKDTNF-UHFFFAOYSA-N 0.000 claims description 4
- ZMNOALTYMSMMTH-UHFFFAOYSA-N n-[5-(4-chlorophenyl)-4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-2-methyl-1h-pyrrol-3-yl]pyrazine-2-carboxamide Chemical compound C=1N=CC=NC=1C(=O)NC1=C(C)NC(C=2C=CC(Cl)=CC=2)=C1CN(CC1)CCN1C1=CC=C(F)C=C1 ZMNOALTYMSMMTH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims description 4
- KOBBZTAETAIYJE-UHFFFAOYSA-N 1-[[1,5-bis(4-chlorophenyl)-2-methylpyrrol-3-yl]methyl]-4-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CC2=C(N(C(C=3C=CC(Cl)=CC=3)=C2)C=2C=CC(Cl)=CC=2)C)CC1 KOBBZTAETAIYJE-UHFFFAOYSA-N 0.000 claims description 3
- LQBJHMJPGICZCY-UHFFFAOYSA-N 1-[[1,5-bis(4-chlorophenyl)-2-methylpyrrol-3-yl]methyl]-4-(4-fluorophenyl)piperazine Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N(C=2C=CC(Cl)=CC=2)C(C)=C1CN(CC1)CCN1C1=CC=C(F)C=C1 LQBJHMJPGICZCY-UHFFFAOYSA-N 0.000 claims description 3
- AVOSJTIJOJXQJS-UHFFFAOYSA-N 1-[[1,5-bis(4-chlorophenyl)-2-methylpyrrol-3-yl]methyl]-4-(5-chloro-2-methylphenyl)piperazine Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N(C=2C=CC(Cl)=CC=2)C(C)=C1CN(CC1)CCN1C1=CC(Cl)=CC=C1C AVOSJTIJOJXQJS-UHFFFAOYSA-N 0.000 claims description 3
- AVCUZHHBXKVSGO-UHFFFAOYSA-N 1-[[1,5-bis(4-chlorophenyl)-2-methylpyrrol-3-yl]methyl]-4-pyridin-2-ylpiperazine Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N(C=2C=CC(Cl)=CC=2)C(C)=C1CN(CC1)CCN1C1=CC=CC=N1 AVCUZHHBXKVSGO-UHFFFAOYSA-N 0.000 claims description 3
- YSQLKMRUFHJTJG-UHFFFAOYSA-N 1-benzhydryl-4-[[1,5-bis(4-chlorophenyl)-2-methylpyrrol-3-yl]methyl]piperazine Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N(C=2C=CC(Cl)=CC=2)C(C)=C1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 YSQLKMRUFHJTJG-UHFFFAOYSA-N 0.000 claims description 3
- VFFMYEWQPQEVFG-UHFFFAOYSA-N 2-[4-[[1,5-bis(4-chlorophenyl)-2-methylpyrrol-3-yl]methyl]piperazin-1-yl]pyrimidine Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N(C=2C=CC(Cl)=CC=2)C(C)=C1CN(CC1)CCN1C1=NC=CC=N1 VFFMYEWQPQEVFG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- BOYVJPKQAYPFHY-UHFFFAOYSA-N bis[3-[4-[[1,5-bis(4-chlorophenyl)-2-methylpyrrol-3-yl]methyl]piperazin-1-yl]furan-2-yl]methanone Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N(C=2C=CC(Cl)=CC=2)C(C)=C1CN(CC1)CCN1C=1C=COC=1C(=O)C=1OC=CC=1N(CC1)CCN1CC(=C(N1C=2C=CC(Cl)=CC=2)C)C=C1C1=CC=C(Cl)C=C1 BOYVJPKQAYPFHY-UHFFFAOYSA-N 0.000 claims description 3
- 230000000813 microbial effect Effects 0.000 claims description 3
- XNZWKXZVRWQFQW-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-4-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-5-methyl-2-phenylpyrrol-3-yl]pyrazine-2-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CC=2C(=NC(C=2NC(=O)C=2N=CC=NC=2)(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)C)CC1 XNZWKXZVRWQFQW-UHFFFAOYSA-N 0.000 claims description 3
- AIKGQKAJRLDGBD-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-5-methyl-2-phenylpyrrol-3-yl]pyrazine-2-carboxamide Chemical compound C1CN(C=2C=CC(F)=CC=2)CCN1CC=1C(C)=NC(C=2C=CC(Cl)=CC=2)(C=2C=CC=CC=2)C=1NC(=O)C1=CN=CC=N1 AIKGQKAJRLDGBD-UHFFFAOYSA-N 0.000 claims description 3
- ZGPKKYSPOXHMNU-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-5-methyl-2-phenyl-4-[[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]pyrrol-3-yl]pyrazine-2-carboxamide Chemical compound C1CN(C=2C=C(C=CC=2)C(F)(F)F)CCN1CC=1C(C)=NC(C=2C=CC(Cl)=CC=2)(C=2C=CC=CC=2)C=1NC(=O)C1=CN=CC=N1 ZGPKKYSPOXHMNU-UHFFFAOYSA-N 0.000 claims description 3
- KRDBDKUUEDYKHE-UHFFFAOYSA-N n-[2-methyl-5-phenyl-4-[(4-pyridin-2-ylpiperazin-1-yl)methyl]-1h-pyrrol-3-yl]pyrazine-2-carboxamide Chemical compound C=1N=CC=NC=1C(=O)NC1=C(C)NC(C=2C=CC=CC=2)=C1CN(CC1)CCN1C1=CC=CC=N1 KRDBDKUUEDYKHE-UHFFFAOYSA-N 0.000 claims description 3
- PTWMLQUGKUSNMS-UHFFFAOYSA-N n-[2-methyl-5-phenyl-4-[[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-1h-pyrrol-3-yl]pyrazine-2-carboxamide Chemical compound C=1N=CC=NC=1C(=O)NC1=C(C)NC(C=2C=CC=CC=2)=C1CN(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 PTWMLQUGKUSNMS-UHFFFAOYSA-N 0.000 claims description 3
- ZMHQFLYZTHJJOU-UHFFFAOYSA-N n-[4-[(4-benzhydrylpiperazin-1-yl)methyl]-2-methyl-5-phenyl-1h-pyrrol-3-yl]pyrazine-2-carboxamide Chemical compound C=1N=CC=NC=1C(=O)NC1=C(C)NC(C=2C=CC=CC=2)=C1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ZMHQFLYZTHJJOU-UHFFFAOYSA-N 0.000 claims description 3
- MMWXQTZNHJDTGP-UHFFFAOYSA-N n-[4-[(4-benzhydrylpiperazin-1-yl)methyl]-5-methyl-2-phenyl-1h-pyrrol-3-yl]pyrazine-2-carboxamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1CC1=C(C)NC(C=2C=CC=CC=2)=C1NC(=O)C1=CN=CC=N1 MMWXQTZNHJDTGP-UHFFFAOYSA-N 0.000 claims description 3
- MSHPZLMAFKCXSJ-UHFFFAOYSA-N n-[4-[(4-benzylpiperazin-1-yl)methyl]-5-methyl-2-phenyl-1h-pyrrol-3-yl]pyridine-4-carboxamide Chemical compound C1CN(CC=2C=CC=CC=2)CCN1CC1=C(C)NC(C=2C=CC=CC=2)=C1NC(=O)C1=CC=NC=C1 MSHPZLMAFKCXSJ-UHFFFAOYSA-N 0.000 claims description 3
- ATHYLIGWMCEGLD-UHFFFAOYSA-N n-[4-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-2-methyl-5-phenyl-1h-pyrrol-3-yl]pyrazine-2-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CC2=C(NC(C)=C2NC(=O)C=2N=CC=NC=2)C=2C=CC=CC=2)CC1 ATHYLIGWMCEGLD-UHFFFAOYSA-N 0.000 claims description 3
- GODLKHPBSQCFRG-UHFFFAOYSA-N n-[4-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-5-methyl-2-phenyl-1h-pyrrol-3-yl]pyrazine-2-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CC=2C(=C(NC=2C)C=2C=CC=CC=2)NC(=O)C=2N=CC=NC=2)CC1 GODLKHPBSQCFRG-UHFFFAOYSA-N 0.000 claims description 3
- LAXAKXNNODYXQH-UHFFFAOYSA-N n-[4-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-5-methyl-2-phenyl-1h-pyrrol-3-yl]pyridine-4-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CC=2C(=C(NC=2C)C=2C=CC=CC=2)NC(=O)C=2C=CN=CC=2)CC1 LAXAKXNNODYXQH-UHFFFAOYSA-N 0.000 claims description 3
- YMAURVATROPZPJ-UHFFFAOYSA-N n-[4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-2-methyl-5-phenyl-1h-pyrrol-3-yl]pyrazine-2-carboxamide Chemical compound C=1N=CC=NC=1C(=O)NC1=C(C)NC(C=2C=CC=CC=2)=C1CN(CC1)CCN1C1=CC=C(F)C=C1 YMAURVATROPZPJ-UHFFFAOYSA-N 0.000 claims description 3
- MFKBBTHBHKWKHP-UHFFFAOYSA-N n-[4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-2-methyl-5-phenyl-1h-pyrrol-3-yl]pyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NC1=C(C)NC(C=2C=CC=CC=2)=C1CN(CC1)CCN1C1=CC=C(F)C=C1 MFKBBTHBHKWKHP-UHFFFAOYSA-N 0.000 claims description 3
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- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 229960003231 thioacetazone Drugs 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2002/000189 WO2004026828A1 (en) | 2002-09-20 | 2002-09-20 | Pyrrole derivatives as antimycobacterial compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20050347A2 true HRP20050347A2 (en) | 2006-03-31 |
Family
ID=32012142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20050347A HRP20050347A2 (en) | 2002-09-20 | 2005-04-19 | Pyrrole derivatives as antimycobacterial compounds |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US7691837B2 (ru) |
| EP (2) | EP1857442A3 (ru) |
| JP (1) | JP2006503837A (ru) |
| CN (1) | CN1668584A (ru) |
| AP (1) | AP1979A (ru) |
| AU (1) | AU2002343200B2 (ru) |
| BR (1) | BR0215873A (ru) |
| CA (1) | CA2499701A1 (ru) |
| EA (1) | EA012461B1 (ru) |
| HR (1) | HRP20050347A2 (ru) |
| HU (1) | HUP0500598A2 (ru) |
| IS (1) | IS7795A (ru) |
| MX (1) | MXPA05003022A (ru) |
| NO (1) | NO20051901L (ru) |
| NZ (1) | NZ539449A (ru) |
| RS (1) | RS20050231A (ru) |
| TN (1) | TNSN05080A1 (ru) |
| UA (1) | UA81640C2 (ru) |
| WO (1) | WO2004026828A1 (ru) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7491721B2 (en) * | 2004-05-12 | 2009-02-17 | Lupin Limited | Antimycobacterial pharmaceutical composition |
| CN101163693B (zh) * | 2005-02-18 | 2013-03-06 | 阿斯利康(瑞典)有限公司 | 抗菌哌啶衍生物 |
| ITRM20050094A1 (it) | 2005-03-04 | 2006-09-05 | Univ Siena | Derivati del 1-(1,5-di(4-clorofenil)-2metil-1h-3-pirroli)metil)-4-metilpiperazina (bm 212), procedimento per la loro produzione e uso di essi come antitubercolari. |
| AU2006233943A1 (en) * | 2005-04-11 | 2006-10-19 | Lupin Limited | Preparation of (2-methyl-5-phenyl-3-(piperazin-1-ylmethyl)) pyrrole derivatives |
| CN101190894A (zh) * | 2006-11-23 | 2008-06-04 | 中国人民解放军军事医学科学院毒物药物研究所 | 脂肪酸合成酶抑制剂及其制药用途 |
| EP2311457A1 (en) | 2009-10-19 | 2011-04-20 | Forschungszentrum Borstel | Pharmaceutical compositions for treating infections with drug resistant mycobacteria |
| HUP1000033A2 (en) * | 2010-01-21 | 2011-07-28 | Uratim Kft | Piperazine derivatives useful against mycobacteriums |
| CN102802650B (zh) * | 2010-03-22 | 2014-05-21 | 科学与工业技术研究委员会 | 刺果藤属物种的抗结核病组合物 |
| KR100998556B1 (ko) | 2010-04-08 | 2010-12-07 | 강원대학교산학협력단 | 신규한 다치환 피롤 유도체와 이의 제조방법 |
| CN103122370B (zh) * | 2011-11-21 | 2014-06-18 | 华中农业大学 | 一种三嗪类化合物作为抗结核分枝杆菌抑制剂的应用 |
| US9458044B2 (en) | 2012-07-13 | 2016-10-04 | Corning Incorporated | Methods and apparatuses for producing laminated glass sheets |
| IN2013DE01663A (ru) | 2013-06-03 | 2015-07-10 | Council Scient Ind Res | |
| RU2767542C1 (ru) * | 2021-05-24 | 2022-03-17 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | Противотуберкулезное средство на основе 4-((гет)ароил)-3- гидрокси-1-(2-гидроксифенил)-5-(фенилтио)-1,5-дигидро-2Н-пиррол-2-онов |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2986564A (en) * | 1959-02-20 | 1961-05-30 | Rips Richard | Pyrrole compounds |
| US3246010A (en) | 1963-06-10 | 1966-04-12 | Parke Davis & Co | 1, 5-diaryl-2-pyrrole propanols and ethers |
| US3168532A (en) * | 1963-06-12 | 1965-02-02 | Parke Davis & Co | 1, 5-diarylpyrrole-2-propionic acid compounds |
| US3168531A (en) * | 1963-06-12 | 1965-02-02 | Parke Davis & Co | 1-aryl-5-(p-lower alkoxyphenyl)-pyrrole-2-propionic acid compounds |
| GB1263940A (en) * | 1968-08-02 | 1972-02-16 | Innothera Lab Sa | 0-phenyl-pyrroles |
-
2002
- 2002-09-20 RS YUP-2005/0231A patent/RS20050231A/sr unknown
- 2002-09-20 EP EP07017067A patent/EP1857442A3/en not_active Withdrawn
- 2002-09-20 EA EA200500500A patent/EA012461B1/ru not_active IP Right Cessation
- 2002-09-20 US US10/497,615 patent/US7691837B2/en not_active Expired - Fee Related
- 2002-09-20 EP EP02779869A patent/EP1546097A1/en not_active Withdrawn
- 2002-09-20 HU HU0500598A patent/HUP0500598A2/hu unknown
- 2002-09-20 WO PCT/IN2002/000189 patent/WO2004026828A1/en not_active Application Discontinuation
- 2002-09-20 BR BR0215873-6A patent/BR0215873A/pt not_active IP Right Cessation
- 2002-09-20 CN CNA028296346A patent/CN1668584A/zh active Pending
- 2002-09-20 JP JP2004537473A patent/JP2006503837A/ja active Pending
- 2002-09-20 UA UAA200503537A patent/UA81640C2/ru unknown
- 2002-09-20 AU AU2002343200A patent/AU2002343200B2/en not_active Ceased
- 2002-09-20 CA CA002499701A patent/CA2499701A1/en not_active Abandoned
- 2002-09-20 AP AP2005003277A patent/AP1979A/xx active
- 2002-09-20 NZ NZ539449A patent/NZ539449A/en not_active IP Right Cessation
- 2002-09-20 MX MXPA05003022A patent/MXPA05003022A/es unknown
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2005
- 2005-03-18 TN TNP2005000080A patent/TNSN05080A1/en unknown
- 2005-04-11 IS IS7795A patent/IS7795A/is unknown
- 2005-04-19 NO NO20051901A patent/NO20051901L/no not_active Application Discontinuation
- 2005-04-19 HR HR20050347A patent/HRP20050347A2/hr not_active Application Discontinuation
-
2008
- 2008-06-11 US US12/137,170 patent/US7763602B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| RS20050231A (en) | 2007-06-04 |
| EA012461B1 (ru) | 2009-10-30 |
| EP1546097A1 (en) | 2005-06-29 |
| NZ539449A (en) | 2007-08-31 |
| CN1668584A (zh) | 2005-09-14 |
| UA81640C2 (ru) | 2008-01-25 |
| AU2002343200A1 (en) | 2004-04-08 |
| AU2002343200B2 (en) | 2009-08-13 |
| US20080242676A1 (en) | 2008-10-02 |
| US7691837B2 (en) | 2010-04-06 |
| MXPA05003022A (es) | 2005-05-27 |
| EP1857442A3 (en) | 2008-02-06 |
| AP1979A (en) | 2009-03-20 |
| TNSN05080A1 (en) | 2007-05-14 |
| CA2499701A1 (en) | 2004-04-01 |
| NO20051901L (no) | 2005-04-19 |
| BR0215873A (pt) | 2005-07-12 |
| EA200500500A1 (ru) | 2006-02-24 |
| US20050107370A1 (en) | 2005-05-19 |
| AP2005003277A0 (en) | 2005-06-30 |
| EP1857442A2 (en) | 2007-11-21 |
| IS7795A (is) | 2005-04-11 |
| WO2004026828A1 (en) | 2004-04-01 |
| HUP0500598A2 (en) | 2006-02-28 |
| JP2006503837A (ja) | 2006-02-02 |
| US7763602B2 (en) | 2010-07-27 |
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