CA2528093A1 - Produits aryl-heteroaromatiques, compositions les contenant et utilisation - Google Patents
Produits aryl-heteroaromatiques, compositions les contenant et utilisation Download PDFInfo
- Publication number
- CA2528093A1 CA2528093A1 CA002528093A CA2528093A CA2528093A1 CA 2528093 A1 CA2528093 A1 CA 2528093A1 CA 002528093 A CA002528093 A CA 002528093A CA 2528093 A CA2528093 A CA 2528093A CA 2528093 A1 CA2528093 A1 CA 2528093A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- piperazin
- methanone
- pyrrol
- imidazol
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title abstract description 117
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 239000003814 drug Substances 0.000 claims abstract description 4
- -1 4- {4- [3- (2-chloro-phenyl) -5-methyl-isoxazole-4-carbonyl] -piperazin-1-yl) -phenyl Chemical group 0.000 claims description 187
- 239000002253 acid Substances 0.000 claims description 70
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 11
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 102000004243 Tubulin Human genes 0.000 claims description 10
- 108090000704 Tubulin Proteins 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 210000004027 cell Anatomy 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 230000035755 proliferation Effects 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- JRIMABXHSLDPOY-UHFFFAOYSA-N 3-[4-(4-phenyl-1h-pyrrole-3-carbonyl)piperazin-1-yl]benzonitrile Chemical compound C=1NC=C(C=2C=CC=CC=2)C=1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 JRIMABXHSLDPOY-UHFFFAOYSA-N 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- YEHAFSPUXRGMOF-UHFFFAOYSA-N 3-[4-(3-phenylimidazole-4-carbonyl)piperazin-1-yl]benzonitrile Chemical compound C=1N=CN(C=2C=CC=CC=2)C=1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 YEHAFSPUXRGMOF-UHFFFAOYSA-N 0.000 claims description 4
- HRJGULOIKVEEDQ-UHFFFAOYSA-N 3-[4-(5-phenyl-2-sulfanylidene-1,3-dihydroimidazole-4-carbonyl)piperazin-1-yl]benzonitrile Chemical compound N1C(S)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 HRJGULOIKVEEDQ-UHFFFAOYSA-N 0.000 claims description 4
- NSWNHLDZPLNTDC-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(2-phenyl-1h-pyrrol-3-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(NC=C2)C=2C=CC=CC=2)=C1 NSWNHLDZPLNTDC-UHFFFAOYSA-N 0.000 claims description 4
- XVJBGAZNWMPLLF-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(3-phenyl-1h-pyrrol-2-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(C=CN2)C=2C=CC=CC=2)=C1 XVJBGAZNWMPLLF-UHFFFAOYSA-N 0.000 claims description 4
- OAWKLWMJWIMLCV-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(4-phenyl-1h-pyrrol-3-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C=2C(=CNC=2)C=2C=CC=CC=2)=C1 OAWKLWMJWIMLCV-UHFFFAOYSA-N 0.000 claims description 4
- MXCRMZHVUFLCCD-UHFFFAOYSA-N [4-(3-chlorophenyl)piperazin-1-yl]-(3-phenyl-1h-pyrrol-2-yl)methanone Chemical compound ClC1=CC=CC(N2CCN(CC2)C(=O)C2=C(C=CN2)C=2C=CC=CC=2)=C1 MXCRMZHVUFLCCD-UHFFFAOYSA-N 0.000 claims description 4
- WKDUJKVNQLAUAQ-UHFFFAOYSA-N [4-[3-(hydroxymethyl)phenyl]piperazin-1-yl]-(2-phenyl-1h-pyrrol-3-yl)methanone Chemical compound OCC1=CC=CC(N2CCN(CC2)C(=O)C2=C(NC=C2)C=2C=CC=CC=2)=C1 WKDUJKVNQLAUAQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- JSQFVFVKZGVANQ-UHFFFAOYSA-N (2-amino-4-phenyl-1,3-thiazol-5-yl)-[4-[3-(hydroxymethyl)phenyl]piperazin-1-yl]methanone Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(CO)=C1 JSQFVFVKZGVANQ-UHFFFAOYSA-N 0.000 claims description 3
- IMWLLSZOLWWMTG-UHFFFAOYSA-N (4-phenyl-1h-imidazol-5-yl)-(4-pyridin-3-ylpiperazin-1-yl)methanone Chemical compound N1C=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CN=C1 IMWLLSZOLWWMTG-UHFFFAOYSA-N 0.000 claims description 3
- IISFNCJURYTOGV-UHFFFAOYSA-N 3-[4-(4-phenyl-1h-imidazole-5-carbonyl)piperazin-1-yl]benzonitrile Chemical compound N1C=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 IISFNCJURYTOGV-UHFFFAOYSA-N 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- AAKVKMQATUOQAK-UHFFFAOYSA-N [2-(4-chlorophenyl)furan-3-yl]-[4-(3-methoxyphenyl)piperazin-1-yl]methanone Chemical compound COC1=CC=CC(N2CCN(CC2)C(=O)C2=C(OC=C2)C=2C=CC(Cl)=CC=2)=C1 AAKVKMQATUOQAK-UHFFFAOYSA-N 0.000 claims description 3
- WQLGNVRHIMLWDT-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(2-methyl-4-phenyl-1,3-thiazol-5-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N=C(C)S2)C=2C=CC=CC=2)=C1 WQLGNVRHIMLWDT-UHFFFAOYSA-N 0.000 claims description 3
- LCSQNNICYSIJIG-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-[1-(2-hydroxyethyl)-2-phenylpyrrol-3-yl]methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N(CCO)C=C2)C=2C=CC=CC=2)=C1 LCSQNNICYSIJIG-UHFFFAOYSA-N 0.000 claims description 3
- LRBHFVPAJZCNQL-UHFFFAOYSA-N [4-(3,5-dimethylphenyl)piperazin-1-yl]-[2-(2-methoxyethylamino)-4-phenyl-1,3-thiazol-5-yl]methanone Chemical compound S1C(NCCOC)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC(C)=CC(C)=C1 LRBHFVPAJZCNQL-UHFFFAOYSA-N 0.000 claims description 3
- XEGWLHUDVLKYJU-UHFFFAOYSA-N [4-(3-chlorophenyl)piperazin-1-yl]-(2-phenyl-1h-pyrrol-3-yl)methanone Chemical compound ClC1=CC=CC(N2CCN(CC2)C(=O)C2=C(NC=C2)C=2C=CC=CC=2)=C1 XEGWLHUDVLKYJU-UHFFFAOYSA-N 0.000 claims description 3
- WELRZMGYQBXTOR-UHFFFAOYSA-N [4-(3-chlorophenyl)piperazin-1-yl]-(3-phenylthiophen-2-yl)methanone Chemical compound ClC1=CC=CC(N2CCN(CC2)C(=O)C2=C(C=CS2)C=2C=CC=CC=2)=C1 WELRZMGYQBXTOR-UHFFFAOYSA-N 0.000 claims description 3
- DSABEFXPCZJARP-UHFFFAOYSA-N [4-(3-chlorophenyl)piperazin-1-yl]-(4-phenyl-1h-pyrrol-3-yl)methanone Chemical compound ClC1=CC=CC(N2CCN(CC2)C(=O)C=2C(=CNC=2)C=2C=CC=CC=2)=C1 DSABEFXPCZJARP-UHFFFAOYSA-N 0.000 claims description 3
- SGMKXOIIRHQVMG-UHFFFAOYSA-N [4-(3-methoxyphenyl)piperazin-1-yl]-(4-phenyl-1h-imidazol-5-yl)methanone Chemical compound COC1=CC=CC(N2CCN(CC2)C(=O)C2=C(N=CN2)C=2C=CC=CC=2)=C1 SGMKXOIIRHQVMG-UHFFFAOYSA-N 0.000 claims description 3
- SVWOOCWFNNIZDA-UHFFFAOYSA-N [4-[3-(hydroxymethyl)phenyl]piperazin-1-yl]-(4-phenyl-1h-imidazol-5-yl)methanone Chemical compound OCC1=CC=CC(N2CCN(CC2)C(=O)C2=C(N=CN2)C=2C=CC=CC=2)=C1 SVWOOCWFNNIZDA-UHFFFAOYSA-N 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 230000001575 pathological effect Effects 0.000 claims description 3
- 210000004881 tumor cell Anatomy 0.000 claims description 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
- MGNLQALRHMQGRS-UHFFFAOYSA-N 3-[4-(1-methyl-4-phenylpyrrole-3-carbonyl)piperazin-1-yl]benzamide Chemical compound C=1C=CC=CC=1C1=CN(C)C=C1C(=O)N(CC1)CCN1C1=CC=CC(C(N)=O)=C1 MGNLQALRHMQGRS-UHFFFAOYSA-N 0.000 claims description 2
- FWCBBSTVUAASDV-UHFFFAOYSA-N 3-[4-(2-amino-4-phenyl-1,3-thiazole-5-carbonyl)piperazin-1-yl]benzamide Chemical compound NC(=O)C1=CC=CC(N2CCN(CC2)C(=O)C2=C(N=C(N)S2)C=2C=CC=CC=2)=C1 FWCBBSTVUAASDV-UHFFFAOYSA-N 0.000 claims description 2
- OSMVJIRBVRPVLQ-UHFFFAOYSA-N 3-[4-(3-phenyl-1h-pyrrole-2-carbonyl)piperazin-1-yl]benzamide Chemical compound NC(=O)C1=CC=CC(N2CCN(CC2)C(=O)C2=C(C=CN2)C=2C=CC=CC=2)=C1 OSMVJIRBVRPVLQ-UHFFFAOYSA-N 0.000 claims description 2
- AIWHFPNNPDGVST-UHFFFAOYSA-N 3-[4-(4-phenyl-1h-pyrrole-3-carbonyl)piperazin-1-yl]benzamide Chemical compound NC(=O)C1=CC=CC(N2CCN(CC2)C(=O)C=2C(=CNC=2)C=2C=CC=CC=2)=C1 AIWHFPNNPDGVST-UHFFFAOYSA-N 0.000 claims description 2
- PUUUQTODUUKDOB-UHFFFAOYSA-N 3-[4-[2-(2-methoxyethylamino)-4-phenyl-1,3-thiazole-5-carbonyl]piperazin-1-yl]benzonitrile Chemical compound S1C(NCCOC)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 PUUUQTODUUKDOB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- SCXTYHPIUZWMRP-UHFFFAOYSA-N 5-[4-(3,5-dimethoxyphenyl)piperazine-1-carbonyl]-4-phenyl-3h-1,3-thiazol-2-one Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N=C(O)S2)C=2C=CC=CC=2)=C1 SCXTYHPIUZWMRP-UHFFFAOYSA-N 0.000 claims description 2
- RFGDCADBISBUTA-UHFFFAOYSA-N [3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]-(4-pyridin-2-ylpiperazin-1-yl)methanone Chemical compound CC=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1C(=O)N(CC1)CCN1C1=CC=CC=N1 RFGDCADBISBUTA-UHFFFAOYSA-N 0.000 claims description 2
- QPTBXDYWAWRRBB-UHFFFAOYSA-N [3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]-[4-(2,3-dimethylphenyl)piperazin-1-yl]methanone Chemical compound CC=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1C(=O)N(CC1)CCN1C1=CC=CC(C)=C1C QPTBXDYWAWRRBB-UHFFFAOYSA-N 0.000 claims description 2
- YKLCDKIRJCRNOF-UHFFFAOYSA-N [3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]-[4-(2-fluorophenyl)piperazin-1-yl]methanone Chemical compound CC=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1C(=O)N(CC1)CCN1C1=CC=CC=C1F YKLCDKIRJCRNOF-UHFFFAOYSA-N 0.000 claims description 2
- NUZHFCHDSLXWMB-UHFFFAOYSA-N [3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical compound CC=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1C(=O)N(CC1)CCN1C1=CC=C(F)C=C1 NUZHFCHDSLXWMB-UHFFFAOYSA-N 0.000 claims description 2
- KFOWJXRKNNZZHQ-UHFFFAOYSA-N [3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methanone Chemical compound CC=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1C(=O)N(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 KFOWJXRKNNZZHQ-UHFFFAOYSA-N 0.000 claims description 2
- FQQQIDMUZUMOGS-UHFFFAOYSA-N [3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]-[4-(2-methoxyphenyl)piperazin-1-yl]methanone Chemical compound COC1=CC=CC=C1N1CCN(C(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2F)Cl)CC1 FQQQIDMUZUMOGS-UHFFFAOYSA-N 0.000 claims description 2
- FIHFGMDCKYBDSH-UHFFFAOYSA-N [3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]-(4-pyridin-2-ylpiperazin-1-yl)methanone Chemical compound CC=1ON=C(C=2C(=CC=CC=2)Cl)C=1C(=O)N(CC1)CCN1C1=CC=CC=N1 FIHFGMDCKYBDSH-UHFFFAOYSA-N 0.000 claims description 2
- WVUKBGUNJPPZKT-UHFFFAOYSA-N [3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]-[4-(2-methoxyphenyl)piperazin-1-yl]methanone Chemical compound COC1=CC=CC=C1N1CCN(C(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2)Cl)CC1 WVUKBGUNJPPZKT-UHFFFAOYSA-N 0.000 claims description 2
- VZPGZECGVVSLET-UHFFFAOYSA-N [3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]-[4-(3-chlorophenyl)piperazin-1-yl]methanone Chemical compound CC=1ON=C(C=2C(=CC=CC=2)Cl)C=1C(=O)N(CC1)CCN1C1=CC=CC(Cl)=C1 VZPGZECGVVSLET-UHFFFAOYSA-N 0.000 claims description 2
- JHUVHAANGXSBSY-UHFFFAOYSA-N [3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]methanone Chemical compound CC=1ON=C(C=2C(=CC=CC=2)Cl)C=1C(=O)N(CC1)CCN1C1=NC=C(C(F)(F)F)C=C1Cl JHUVHAANGXSBSY-UHFFFAOYSA-N 0.000 claims description 2
- OWXBJAPOSQSWAO-UHFFFAOYSA-N [4-(2-chloro-4-nitrophenyl)piperazin-1-yl]-(5-methyl-3-phenyl-1,2-oxazol-4-yl)methanone Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C(=O)N(CC1)CCN1C1=CC=C([N+]([O-])=O)C=C1Cl OWXBJAPOSQSWAO-UHFFFAOYSA-N 0.000 claims description 2
- HHZMWKNOCCEMIJ-UHFFFAOYSA-N [4-(2-chlorophenyl)-5-methyl-1,2-oxazol-3-yl]-[4-(2-fluorophenyl)piperazin-1-yl]methanone Chemical compound C=1C=CC=C(Cl)C=1C1=C(C)ON=C1C(=O)N(CC1)CCN1C1=CC=CC=C1F HHZMWKNOCCEMIJ-UHFFFAOYSA-N 0.000 claims description 2
- OHIQYDFDYIMGRD-UHFFFAOYSA-N [4-(2-chlorophenyl)-5-methyl-1,2-oxazol-3-yl]-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical compound C=1C=CC=C(Cl)C=1C1=C(C)ON=C1C(=O)N(CC1)CCN1C1=CC=C(F)C=C1 OHIQYDFDYIMGRD-UHFFFAOYSA-N 0.000 claims description 2
- KDDUFNRXJZVCGN-UHFFFAOYSA-N [4-(2-fluorophenyl)piperazin-1-yl]-(4-phenylthiadiazol-5-yl)methanone Chemical compound FC1=CC=CC=C1N1CCN(C(=O)C2=C(N=NS2)C=2C=CC=CC=2)CC1 KDDUFNRXJZVCGN-UHFFFAOYSA-N 0.000 claims description 2
- GOEPFJGUMPLVOG-UHFFFAOYSA-N [4-(2-fluorophenyl)piperazin-1-yl]-(5-methyl-3-phenyl-1,2-oxazol-4-yl)methanone Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C(=O)N(CC1)CCN1C1=CC=CC=C1F GOEPFJGUMPLVOG-UHFFFAOYSA-N 0.000 claims description 2
- DCIXECPRAXUAMO-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(1-methyl-2-methylsulfanyl-5-phenylimidazol-4-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N(C)C(SC)=N2)C=2C=CC=CC=2)=C1 DCIXECPRAXUAMO-UHFFFAOYSA-N 0.000 claims description 2
- ZLMTYHIPIODBGR-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(1-methyl-2-phenylpyrrol-3-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N(C)C=C2)C=2C=CC=CC=2)=C1 ZLMTYHIPIODBGR-UHFFFAOYSA-N 0.000 claims description 2
- ONNDHHBHLXCKTE-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(2-methylsulfonyl-4-phenyl-1h-imidazol-5-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N=C(N2)S(C)(=O)=O)C=2C=CC=CC=2)=C1 ONNDHHBHLXCKTE-UHFFFAOYSA-N 0.000 claims description 2
- RBJKVCUOOLRIJY-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(4-phenyl-1,3-thiazol-5-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N=CS2)C=2C=CC=CC=2)=C1 RBJKVCUOOLRIJY-UHFFFAOYSA-N 0.000 claims description 2
- UPPIQJMQCOKLFP-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(4-phenyl-1h-imidazol-5-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N=CN2)C=2C=CC=CC=2)=C1 UPPIQJMQCOKLFP-UHFFFAOYSA-N 0.000 claims description 2
- DWBWNWJNADJNBS-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-[1-(2-hydroxyethyl)-4-phenylpyrrol-3-yl]methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C=2C(=CN(CCO)C=2)C=2C=CC=CC=2)=C1 DWBWNWJNADJNBS-UHFFFAOYSA-N 0.000 claims description 2
- VFEOPGDDGZTXOA-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-[1-(hydroxymethyl)-4-phenylpyrrol-3-yl]methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C=2C(=CN(CO)C=2)C=2C=CC=CC=2)=C1 VFEOPGDDGZTXOA-UHFFFAOYSA-N 0.000 claims description 2
- YRFHMXBFNPQYAP-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-[2-(2-methoxyethylamino)-4-phenyl-1,3-thiazol-5-yl]methanone Chemical compound S1C(NCCOC)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC(OC)=CC(OC)=C1 YRFHMXBFNPQYAP-UHFFFAOYSA-N 0.000 claims description 2
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- CHXKZVOYQIWWLU-UHFFFAOYSA-N 3-[4-[1-(1-hydroxyethyl)-2-phenylpyrrole-3-carbonyl]piperazin-1-yl]benzonitrile Chemical compound C=1C=CC=CC=1C=1N(C(O)C)C=CC=1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 CHXKZVOYQIWWLU-UHFFFAOYSA-N 0.000 description 1
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- KNFJXXWJPOVNAZ-UHFFFAOYSA-N 3-[4-[4-phenyl-2-(trifluoromethyl)-1h-imidazole-5-carbonyl]piperazin-1-yl]benzamide Chemical compound NC(=O)C1=CC=CC(N2CCN(CC2)C(=O)C2=C(N=C(N2)C(F)(F)F)C=2C=CC=CC=2)=C1 KNFJXXWJPOVNAZ-UHFFFAOYSA-N 0.000 description 1
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- STXAVEHFKAXGOX-UHFFFAOYSA-N 3-bromobenzonitrile Chemical compound BrC1=CC=CC(C#N)=C1 STXAVEHFKAXGOX-UHFFFAOYSA-N 0.000 description 1
- KWWGBNRBZMJKPA-UHFFFAOYSA-N 3-phenylthiophene-2-carboxylic acid Chemical compound S1C=CC(C=2C=CC=CC=2)=C1C(=O)O KWWGBNRBZMJKPA-UHFFFAOYSA-N 0.000 description 1
- HUUNJDIASCEFMX-UHFFFAOYSA-N 3-piperazin-1-ylbenzamide;dihydrochloride Chemical compound Cl.Cl.NC(=O)C1=CC=CC(N2CCNCC2)=C1 HUUNJDIASCEFMX-UHFFFAOYSA-N 0.000 description 1
- NVTBASMQHFMANH-UHFFFAOYSA-N 4-(chloromethyl)-1,3-thiazole;hydron;chloride Chemical compound Cl.ClCC1=CSC=N1 NVTBASMQHFMANH-UHFFFAOYSA-N 0.000 description 1
- YNOAMDJRZSNZPH-UHFFFAOYSA-N 4-[3-[4-(3,5-dimethoxyphenyl)piperazine-1-carbonyl]-4-phenylpyrrol-1-yl]butanoic acid Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C=2C(=CN(CCCC(O)=O)C=2)C=2C=CC=CC=2)=C1 YNOAMDJRZSNZPH-UHFFFAOYSA-N 0.000 description 1
- JUCLXFPLJNDBJO-UHFFFAOYSA-N 4-phenyl-1,3-dihydroimidazol-2-one Chemical compound N1C(=O)NC=C1C1=CC=CC=C1 JUCLXFPLJNDBJO-UHFFFAOYSA-N 0.000 description 1
- UXIWLHNMLDJWMF-UHFFFAOYSA-N 4-phenyl-3h-1,3-thiazol-2-one Chemical compound S1C(O)=NC(C=2C=CC=CC=2)=C1 UXIWLHNMLDJWMF-UHFFFAOYSA-N 0.000 description 1
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical class O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 1
- RUKDIKJSGDVSIF-UHFFFAOYSA-N 5-phenyl-1,3-oxazole-4-carboxylic acid Chemical compound N1=COC(C=2C=CC=CC=2)=C1C(=O)O RUKDIKJSGDVSIF-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- YKLSIVBOWHBLQF-UHFFFAOYSA-N COC=1C=C(C=C(C1)OC)N1CCN(CC1)Cl Chemical compound COC=1C=C(C=C(C1)OC)N1CCN(CC1)Cl YKLSIVBOWHBLQF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 102000005454 Dimethylallyltranstransferase Human genes 0.000 description 1
- 108010006731 Dimethylallyltranstransferase Proteins 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 229940123583 Factor Xa inhibitor Drugs 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- 102000029749 Microtubule Human genes 0.000 description 1
- 108091022875 Microtubule Proteins 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
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- APUXHTNTNMAMNE-UHFFFAOYSA-N [1-[1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-phenylpyrrol-2-yl]-[4-[3-(hydroxymethyl)phenyl]piperazin-1-yl]methanone Chemical compound CC(C)(C)[Si](C)(C)OC(C)N1C(C(=O)N2CCN(CC2)C=2C=C(CO)C=CC=2)=CC=C1C1=CC=CC=C1 APUXHTNTNMAMNE-UHFFFAOYSA-N 0.000 description 1
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- QQKQEAWOHYCALI-UHFFFAOYSA-N [4-(2-hydroxy-3,5-dimethoxyphenyl)piperazin-1-yl]-(2-methylsulfinyl-4-phenyl-1h-imidazol-5-yl)methanone Chemical compound COC1=CC(OC)=C(O)C(N2CCN(CC2)C(=O)C2=C(NC(=N2)S(C)=O)C=2C=CC=CC=2)=C1 QQKQEAWOHYCALI-UHFFFAOYSA-N 0.000 description 1
- OPHMQDYMDVBYNH-UHFFFAOYSA-N [4-(3-chlorophenyl)piperazin-1-yl]-(3-phenylimidazol-4-yl)methanone Chemical compound ClC1=CC=CC(N2CCN(CC2)C(=O)C=2N(C=NC=2)C=2C=CC=CC=2)=C1 OPHMQDYMDVBYNH-UHFFFAOYSA-N 0.000 description 1
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
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- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
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- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
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- JZBWUTVDIDNCMW-UHFFFAOYSA-L dipotassium;oxido sulfate Chemical compound [K+].[K+].[O-]OS([O-])(=O)=O JZBWUTVDIDNCMW-UHFFFAOYSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
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- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- GMUXVPNXBVLTCG-UHFFFAOYSA-N ethyl 2-methyl-4-phenyl-1h-imidazole-5-carboxylate Chemical compound N1C(C)=NC(C=2C=CC=CC=2)=C1C(=O)OCC GMUXVPNXBVLTCG-UHFFFAOYSA-N 0.000 description 1
- QYWSSFHUNRWYAW-UHFFFAOYSA-N ethyl 2-methylsulfonyl-4-phenyl-1h-imidazole-5-carboxylate Chemical compound N1C(S(C)(=O)=O)=NC(C=2C=CC=CC=2)=C1C(=O)OCC QYWSSFHUNRWYAW-UHFFFAOYSA-N 0.000 description 1
- KUVOQWRTXPCJOZ-UHFFFAOYSA-N ethyl 2-oxo-4-phenyl-3h-1,3-thiazole-5-carboxylate Chemical compound S1C(=O)NC(C=2C=CC=CC=2)=C1C(=O)OCC KUVOQWRTXPCJOZ-UHFFFAOYSA-N 0.000 description 1
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
- NGMYKWXFKDHMJY-UHFFFAOYSA-N ethyl 5-phenyl-2-sulfanylidene-1,3-dihydroimidazole-4-carboxylate Chemical compound N1C(=S)NC(C=2C=CC=CC=2)=C1C(=O)OCC NGMYKWXFKDHMJY-UHFFFAOYSA-N 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-M hydroxide;hydrate Chemical compound O.[OH-] JEGUKCSWCFPDGT-UHFFFAOYSA-M 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
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- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
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- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
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- 239000007924 injection Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- UPAGPWKZSOOAHP-UHFFFAOYSA-N methyl 2-[3-[4-(3-carbamoylphenyl)piperazine-1-carbonyl]-4-phenyl-1h-pyrrol-2-yl]acetate Chemical compound COC(=O)CC=1NC=C(C=2C=CC=CC=2)C=1C(=O)N(CC1)CCN1C1=CC=CC(C(N)=O)=C1 UPAGPWKZSOOAHP-UHFFFAOYSA-N 0.000 description 1
- KQEVIFKPZOGBMZ-UHFFFAOYSA-N methyl 3-bromopropanoate Chemical compound COC(=O)CCBr KQEVIFKPZOGBMZ-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 125000002734 organomagnesium group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229940080469 phosphocellulose Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- BYTCDABWEGFPLT-UHFFFAOYSA-L potassium;sodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[K+] BYTCDABWEGFPLT-UHFFFAOYSA-L 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940121649 protein inhibitor Drugs 0.000 description 1
- 239000012268 protein inhibitor Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- CSRCBLMBBOJYEX-UHFFFAOYSA-M sodium;2-morpholin-4-ylethanesulfonic acid;hydroxide Chemical compound [OH-].[Na+].OS(=O)(=O)CCN1CCOCC1 CSRCBLMBBOJYEX-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000004879 turbidimetry Methods 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D207/34—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic 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
- C07D401/12—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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0306719A FR2855825B1 (fr) | 2003-06-04 | 2003-06-04 | Produits aryl-heteroaromatiques, compositions les contenant et utilisation |
| FR03/06719 | 2003-06-04 | ||
| FR04/04889 | 2004-05-06 | ||
| FR0404889 | 2004-05-06 | ||
| PCT/FR2004/001379 WO2004108685A1 (fr) | 2003-06-04 | 2004-06-03 | Produits aryl-heteroaromatiques, compositions les contenant et utilisation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2528093A1 true CA2528093A1 (fr) | 2004-12-16 |
Family
ID=33512659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002528093A Abandoned CA2528093A1 (fr) | 2003-06-04 | 2004-06-03 | Produits aryl-heteroaromatiques, compositions les contenant et utilisation |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20050014765A1 (https=) |
| EP (1) | EP1641765A1 (https=) |
| JP (1) | JP4805813B2 (https=) |
| KR (1) | KR20060006850A (https=) |
| AR (1) | AR044586A1 (https=) |
| AU (1) | AU2004245269A1 (https=) |
| BR (1) | BRPI0411001A (https=) |
| CA (1) | CA2528093A1 (https=) |
| CL (1) | CL2004001359A1 (https=) |
| IL (1) | IL172222A0 (https=) |
| MX (1) | MXPA05012929A (https=) |
| PA (1) | PA8604401A1 (https=) |
| PE (1) | PE20050226A1 (https=) |
| TW (1) | TW200510344A (https=) |
| UY (1) | UY28350A1 (https=) |
| WO (1) | WO2004108685A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
| AU2005286648A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| EP2289510A1 (en) | 2004-09-20 | 2011-03-02 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
| US7829712B2 (en) * | 2004-09-20 | 2010-11-09 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-CoA-desaturase |
| AR051091A1 (es) * | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| CA2580762A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
| EP1827438B2 (en) * | 2004-09-20 | 2014-12-10 | Xenon Pharmaceuticals Inc. | Piperazin derivatives for inhibiting human stearoyl-coa-desaturase |
| CA2580857A1 (en) * | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| EP1807085B1 (en) | 2004-09-20 | 2013-08-21 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| JP5080256B2 (ja) * | 2004-09-20 | 2012-11-21 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 二環式複素環誘導体およびステアロイル−ＣｏＡデサチュラーゼ（ＳＣＤ）のインヒビターとしてのそれらの使用 |
| AU2006343359A1 (en) | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| TW200800946A (en) * | 2005-08-15 | 2008-01-01 | Astrazeneca Ab | Substituted piperazines as metabotropic glutamate receptor antagonists |
| JPWO2007119833A1 (ja) * | 2006-04-14 | 2009-08-27 | 武田薬品工業株式会社 | 含窒素複素環化合物 |
| DE102006027229A1 (de) | 2006-06-09 | 2007-12-20 | Grünenthal GmbH | 1,3-Disubstituierte 4-Methyl-1H-pyrrol-2-carbonsäureamide und ihre Verwendung zur Herstellung von Arzneimitteln |
| US8148367B2 (en) * | 2007-01-12 | 2012-04-03 | Takeda Pharmaceutical Company Limited | Renin inhibitors |
| WO2009117444A1 (en) * | 2008-03-17 | 2009-09-24 | Northeastern University | Inhibitors of fatty acid amide hydrolase and monoacylglycerol lipase for modulation of cannabinoid receptors |
| JP5657566B2 (ja) | 2008-12-24 | 2015-01-21 | バイアル ポルテラ アンド シーエイ エス エイＢＩＡＬ−Ｐｏｒｔｅｌａ ＆ Ｃａ， Ｓ．Ａ． | 医薬品 |
| KR101297652B1 (ko) * | 2010-11-25 | 2013-08-19 | 한국과학기술연구원 | 항암활성을 지닌 카르보아졸계 화합물 |
| US20140343017A1 (en) * | 2012-01-25 | 2014-11-20 | Kabushiki Kaisha Yakult Honsha | Pyrrole compound |
| KR101689093B1 (ko) | 2012-06-04 | 2016-12-22 | 액테리온 파마슈티칼 리미티드 | 벤즈이미다졸-프롤린 유도체 |
| BR112015007516A2 (pt) | 2012-10-10 | 2017-07-04 | Actelion Pharmaceuticals Ltd | antagonistas do receptor de orexina que são derivados de [orto bi-(hetero-)aril]-[2-(meta bi-(hetero-)aril)- pirrolidin-1-il]-metanona |
| CA2902135A1 (en) | 2013-03-12 | 2014-09-18 | Actelion Pharmaceuticals Ltd | Azetidine amide derivatives as orexin receptor antagonists |
| HRP20181710T1 (hr) | 2013-12-04 | 2018-12-28 | Idorsia Pharmaceuticals Ltd | Uporaba derivata benzimidazol-prolina |
| EP3947342A4 (en) | 2019-03-28 | 2022-12-28 | Council of Scientific and Industrial Research | NEW PROCESS FOR THE MANUFACTURE OF TAPENTADOL AND INTERMEDIATE PRODUCTS FROM IT |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9707561A (es) * | 1995-04-07 | 1997-12-31 | Schering Corp | Compuestos de carbonil piperazinilo y piperidinilo. |
| US5880128A (en) * | 1996-05-08 | 1999-03-09 | Schering Corporation | Carbonyl piperazinyl and piperidinyl compounds |
| DE10035927A1 (de) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| DE10035908A1 (de) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| DE10035928A1 (de) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| FR2815032B1 (fr) * | 2000-10-10 | 2003-08-08 | Pf Medicament | Nouveaux derives d'aminophenyle piperazine ou d'amino phenyle piperide inhibiteurs de proteines prenyl transferase ainsi que leurs preparations |
| CN100509790C (zh) * | 2002-06-29 | 2009-07-08 | 赞塔里斯有限公司 | 芳基羰基哌嗪和杂芳基羰基哌嗪及其治疗良性和恶性肿瘤疾病的用途 |
| AU2003287965A1 (en) * | 2002-10-24 | 2004-05-13 | Carex Sa | Modulation of peroxisome proliferator activated receptors activity |
| GB0228417D0 (en) * | 2002-12-05 | 2003-01-08 | Cancer Rec Tech Ltd | Pyrazole compounds |
-
2004
- 2004-06-02 PE PE2004000556A patent/PE20050226A1/es not_active Application Discontinuation
- 2004-06-02 AR ARP040101890A patent/AR044586A1/es not_active Application Discontinuation
- 2004-06-03 US US10/859,740 patent/US20050014765A1/en not_active Abandoned
- 2004-06-03 JP JP2006508355A patent/JP4805813B2/ja not_active Expired - Fee Related
- 2004-06-03 CL CL200401359A patent/CL2004001359A1/es unknown
- 2004-06-03 KR KR1020057023192A patent/KR20060006850A/ko not_active Ceased
- 2004-06-03 EP EP04767247A patent/EP1641765A1/fr not_active Withdrawn
- 2004-06-03 WO PCT/FR2004/001379 patent/WO2004108685A1/fr not_active Ceased
- 2004-06-03 BR BRPI0411001-3A patent/BRPI0411001A/pt not_active IP Right Cessation
- 2004-06-03 TW TW093115885A patent/TW200510344A/zh unknown
- 2004-06-03 MX MXPA05012929A patent/MXPA05012929A/es active IP Right Grant
- 2004-06-03 CA CA002528093A patent/CA2528093A1/fr not_active Abandoned
- 2004-06-03 AU AU2004245269A patent/AU2004245269A1/en not_active Abandoned
- 2004-06-04 UY UY28350A patent/UY28350A1/es unknown
- 2004-06-04 PA PA20048604401A patent/PA8604401A1/es unknown
-
2005
- 2005-11-28 IL IL172222A patent/IL172222A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006526596A (ja) | 2006-11-24 |
| WO2004108685A1 (fr) | 2004-12-16 |
| MXPA05012929A (es) | 2006-02-28 |
| AU2004245269A1 (en) | 2004-12-16 |
| US20050014765A1 (en) | 2005-01-20 |
| AR044586A1 (es) | 2005-09-21 |
| UY28350A1 (es) | 2004-12-31 |
| TW200510344A (en) | 2005-03-16 |
| PE20050226A1 (es) | 2005-05-18 |
| EP1641765A1 (fr) | 2006-04-05 |
| BRPI0411001A (pt) | 2006-07-04 |
| JP4805813B2 (ja) | 2011-11-02 |
| KR20060006850A (ko) | 2006-01-19 |
| IL172222A0 (en) | 2011-08-01 |
| PA8604401A1 (es) | 2004-12-16 |
| CL2004001359A1 (es) | 2005-05-06 |
| HK1093339A1 (zh) | 2007-03-02 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |