AU2004245269A1 - Aryl-heteroaromatic products, compositions containing same and use thereof - Google Patents
Aryl-heteroaromatic products, compositions containing same and use thereof Download PDFInfo
- Publication number
- AU2004245269A1 AU2004245269A1 AU2004245269A AU2004245269A AU2004245269A1 AU 2004245269 A1 AU2004245269 A1 AU 2004245269A1 AU 2004245269 A AU2004245269 A AU 2004245269A AU 2004245269 A AU2004245269 A AU 2004245269A AU 2004245269 A1 AU2004245269 A1 AU 2004245269A1
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- piperazin
- methanone
- imidazol
- pyrrol
- 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 description 167
- -1 2-chlorophenyl 2-thienyl Chemical group 0.000 claims description 101
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 83
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 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 7
- 210000004027 cell Anatomy 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 230000035755 proliferation Effects 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- QXGYJWXBMJDQGZ-UHFFFAOYSA-N 3-[4-(2-oxo-4-phenyl-3h-1,3-thiazole-5-carbonyl)piperazin-1-yl]benzamide Chemical compound NC(=O)C1=CC=CC(N2CCN(CC2)C(=O)C2=C(N=C(O)S2)C=2C=CC=CC=2)=C1 QXGYJWXBMJDQGZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 claims description 5
- 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 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 claims description 4
- RYUWWELMYPXZKJ-UHFFFAOYSA-N 3-[4-(2-phenyl-1h-pyrrole-3-carbonyl)piperazin-1-yl]benzonitrile Chemical compound C1=CNC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 RYUWWELMYPXZKJ-UHFFFAOYSA-N 0.000 claims description 4
- 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
- ZTTWJHFZPZPYHD-UHFFFAOYSA-N 3-[4-(5-phenyl-2-sulfanylidene-1,3-dihydroimidazole-4-carbonyl)piperazin-1-yl]benzamide Chemical compound NC(=O)C1=CC=CC(N2CCN(CC2)C(=O)C2=C(N=C(S)N2)C=2C=CC=CC=2)=C1 ZTTWJHFZPZPYHD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 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
- CQAQZWBDEWVTJJ-UHFFFAOYSA-N 3-[4-(2-methyl-4-phenyl-1h-imidazole-5-carbonyl)piperazin-1-yl]benzamide Chemical compound C=1C=CC=CC=1C=1NC(C)=NC=1C(=O)N(CC1)CCN1C1=CC=CC(C(N)=O)=C1 CQAQZWBDEWVTJJ-UHFFFAOYSA-N 0.000 claims description 3
- CTHNOHWYNHLGMV-UHFFFAOYSA-N 3-[4-(2-methyl-4-phenyl-1h-imidazole-5-carbonyl)piperazin-1-yl]benzonitrile Chemical compound C=1C=CC=CC=1C=1NC(C)=NC=1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 CTHNOHWYNHLGMV-UHFFFAOYSA-N 0.000 claims description 3
- NEHPYIZYRXFJNI-UHFFFAOYSA-N 3-[4-(2-methylsulfonyl-5-phenyl-1,4-dihydroimidazole-5-carbonyl)piperazin-1-yl]benzonitrile Chemical compound C1NC(S(=O)(=O)C)=NC1(C=1C=CC=CC=1)C(=O)N1CCN(C=2C=C(C=CC=2)C#N)CC1 NEHPYIZYRXFJNI-UHFFFAOYSA-N 0.000 claims description 3
- HXDKQFRUUMYXFI-UHFFFAOYSA-N 3-[4-(2-oxo-5-phenyl-1,3-dihydroimidazole-4-carbonyl)piperazin-1-yl]benzamide Chemical compound NC(=O)C1=CC=CC(N2CCN(CC2)C(=O)C2=C(N=C(O)N2)C=2C=CC=CC=2)=C1 HXDKQFRUUMYXFI-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
- 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 3
- CIQKUWDCOUCJRU-UHFFFAOYSA-N 3-[4-[1-(1-hydroxyethyl)-4-phenylpyrrole-3-carbonyl]piperazin-1-yl]benzamide Chemical compound C=1C=CC=CC=1C1=CN(C(O)C)C=C1C(=O)N(CC1)CCN1C1=CC=CC(C(N)=O)=C1 CIQKUWDCOUCJRU-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 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 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- 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 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
- DQMKNHROPZQKGW-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-[4-phenyl-1-(pyridin-3-ylmethyl)pyrrol-3-yl]methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C=2C(=CN(CC=3C=NC=CC=3)C=2)C=2C=CC=CC=2)=C1 DQMKNHROPZQKGW-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
- KSGKIURWMIQOQJ-UHFFFAOYSA-N [4-(3-chlorophenyl)piperazin-1-yl]-(4-phenyl-1h-imidazol-5-yl)methanone Chemical compound ClC1=CC=CC(N2CCN(CC2)C(=O)C2=C(N=CN2)C=2C=CC=CC=2)=C1 KSGKIURWMIQOQJ-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
- GYDZOYOOITWUFO-UHFFFAOYSA-N [4-(3-chlorophenyl)piperazin-1-yl]-(5-phenyl-2-sulfanylidene-1,3-dihydroimidazol-4-yl)methanone Chemical compound C=1C=CC=CC=1C=1NC(S)=NC=1C(=O)N(CC1)CCN1C1=CC=CC(Cl)=C1 GYDZOYOOITWUFO-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
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 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 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000001575 pathological effect Effects 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 210000004881 tumor cell Anatomy 0.000 claims description 3
- CDBOBDXTCRCJJA-UHFFFAOYSA-N (2-amino-4-phenyl-1,3-thiazol-5-yl)-[4-(3,5-dimethoxyphenyl)piperazin-1-yl]methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N=C(N)S2)C=2C=CC=CC=2)=C1 CDBOBDXTCRCJJA-UHFFFAOYSA-N 0.000 claims description 2
- XFIVHJKOEPNRCT-UHFFFAOYSA-N 1-[3-[4-(3,5-dimethoxyphenyl)piperazine-1-carbonyl]-4-phenylpyrrol-1-yl]ethanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C=2C(=CN(C=2)C(C)=O)C=2C=CC=CC=2)=C1 XFIVHJKOEPNRCT-UHFFFAOYSA-N 0.000 claims description 2
- SKYGBVSXNUUDNF-UHFFFAOYSA-N 2-[2-[4-(3-carbamoylphenyl)piperazine-1-carbonyl]-3-phenylpyrrol-1-yl]acetic acid Chemical compound NC(=O)C1=CC=CC(N2CCN(CC2)C(=O)C=2N(C=CC=2C=2C=CC=CC=2)CC(O)=O)=C1 SKYGBVSXNUUDNF-UHFFFAOYSA-N 0.000 claims description 2
- BZNNBSRLVYNHAS-UHFFFAOYSA-N 2-[3-[4-(3,5-dimethoxyphenyl)piperazine-1-carbonyl]-4-phenylpyrrol-1-yl]acetic acid Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C=2C(=CN(CC(O)=O)C=2)C=2C=CC=CC=2)=C1 BZNNBSRLVYNHAS-UHFFFAOYSA-N 0.000 claims description 2
- DRLKOALDPMGLJV-UHFFFAOYSA-N 3-[4-(1-methyl-2-phenylpyrrole-3-carbonyl)piperazin-1-yl]benzamide Chemical compound C=1C=CC=CC=1C=1N(C)C=CC=1C(=O)N(CC1)CCN1C1=CC=CC(C(N)=O)=C1 DRLKOALDPMGLJV-UHFFFAOYSA-N 0.000 claims description 2
- ZALJIGUDWMURFI-UHFFFAOYSA-N 3-[4-(2-methyl-4-phenyl-1,3-thiazole-5-carbonyl)piperazin-1-yl]benzamide Chemical compound S1C(C)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(C(N)=O)=C1 ZALJIGUDWMURFI-UHFFFAOYSA-N 0.000 claims description 2
- LUSHKMRYBKWJGE-UHFFFAOYSA-N 3-[4-(2-oxo-5-phenyl-1,3-dihydroimidazole-4-carbonyl)piperazin-1-yl]benzonitrile Chemical compound N1C(O)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 LUSHKMRYBKWJGE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 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
- 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 claims description 2
- ISOLPDRTYOTMTO-UHFFFAOYSA-N 4-phenyl-1,3-dihydroimidazole-2-thione Chemical compound N1C(S)=NC(C=2C=CC=CC=2)=C1 ISOLPDRTYOTMTO-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
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- 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
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- 239000007924 injection Substances 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- GOVYTZKYELJVRT-UHFFFAOYSA-N methyl 2-[2-[4-(3-cyanophenyl)piperazine-1-carbonyl]-3-phenylpyrrol-1-yl]acetate Chemical compound COC(=O)CN1C=CC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 GOVYTZKYELJVRT-UHFFFAOYSA-N 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
- OAFXBEGKDFKUJP-UHFFFAOYSA-N methyl 3-[3-[4-(3-chlorophenyl)piperazine-1-carbonyl]-4-phenylpyrrol-1-yl]propanoate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1=CN(CCC(=O)OC)C=C1C(=O)N(CC1)CCN1C1=CC=CC(Cl)=C1 OAFXBEGKDFKUJP-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
- PSAHTRPCKTWOAH-UHFFFAOYSA-N n-(3-piperazin-1-ylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N2CCNCC2)=C1 PSAHTRPCKTWOAH-UHFFFAOYSA-N 0.000 description 1
- CLNHXSAUVJWXOI-UHFFFAOYSA-N n-[3-[4-(4-phenyl-1h-imidazole-5-carbonyl)piperazin-1-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2CCN(CC2)C(=O)C2=C(N=CN2)C=2C=CC=CC=2)=C1 CLNHXSAUVJWXOI-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 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
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229940080469 phosphocellulose Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- 238000000746 purification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 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
- 230000007017 scission Effects 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
- 238000003786 synthesis reaction Methods 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
- 238000013519 translation Methods 0.000 description 1
- 238000004879 turbidimetry Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole 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)
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 |
|---|---|
| AU2004245269A1 true AU2004245269A1 (en) | 2004-12-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004245269A Abandoned AU2004245269A1 (en) | 2003-06-04 | 2004-06-03 | Aryl-heteroaromatic products, compositions containing same and use thereof |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20050014765A1 (enExample) |
| EP (1) | EP1641765A1 (enExample) |
| JP (1) | JP4805813B2 (enExample) |
| KR (1) | KR20060006850A (enExample) |
| AR (1) | AR044586A1 (enExample) |
| AU (1) | AU2004245269A1 (enExample) |
| BR (1) | BRPI0411001A (enExample) |
| CA (1) | CA2528093A1 (enExample) |
| CL (1) | CL2004001359A1 (enExample) |
| IL (1) | IL172222A0 (enExample) |
| MX (1) | MXPA05012929A (enExample) |
| PA (1) | PA8604401A1 (enExample) |
| PE (1) | PE20050226A1 (enExample) |
| TW (1) | TW200510344A (enExample) |
| UY (1) | UY28350A1 (enExample) |
| WO (1) | WO2004108685A1 (enExample) |
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 |
| EP2289510A1 (en) | 2004-09-20 | 2011-03-02 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
| US20080167321A1 (en) * | 2004-09-20 | 2008-07-10 | Xenon Pharmaceuticals Inc. | Pyridine Derivatives For Inhibiting Human Stearoyl-Coa-Desaturase |
| CN101084207A (zh) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为硬脂酰CoA去饱和酶抑制剂的用途 |
| JP4958786B2 (ja) | 2004-09-20 | 2012-06-20 | 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 | 複素環誘導体および治療薬としてのそれらの使用 |
| JP5149009B2 (ja) * | 2004-09-20 | 2013-02-20 | 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 | ヒトステアロイル−CoAデサチュラーゼを阻害するためのピリダジン誘導体 |
| MX2007003321A (es) * | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
| AU2005329423A1 (en) * | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| MX2007003329A (es) * | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y biciclicos y su uso como inhibidores de estearoil-coa-desaturasa (scd). |
| US7951805B2 (en) * | 2004-09-20 | 2011-05-31 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
| CN101208089A (zh) | 2005-06-03 | 2008-06-25 | 泽农医药公司 | 氨基噻唑衍生物作为人硬酯酰-CoA去饱和酶抑制剂 |
| TW200800946A (en) * | 2005-08-15 | 2008-01-01 | Astrazeneca Ab | Substituted piperazines as metabotropic glutamate receptor antagonists |
| EP2009011A1 (en) * | 2006-04-14 | 2008-12-31 | Takeda Pharmaceutical Company Limited | Nitrogen-containing heterocyclic compound |
| 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 |
| US9271962B2 (en) * | 2008-03-17 | 2016-03-01 | Northeastern University | Inhibitors of fatty acid amide hydrolase and monoacylglycerol lipase for modulation of cannabinoid receptors |
| TWI469979B (zh) | 2008-12-24 | 2015-01-21 | Bial Portela & Ca Sa | 脂肪酸醯胺水解酶(faah)抑制劑、以及其藥學組成物與用途 |
| 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 |
| WO2014057435A1 (en) | 2012-10-10 | 2014-04-17 | Actelion Pharmaceuticals Ltd | Orexin receptor antagonists which are [ortho bi (hetero )aryl]-[2-(meta bi (hetero )aryl)-pyrrolidin-1-yl]-methanone derivatives |
| WO2014141065A1 (en) | 2013-03-12 | 2014-09-18 | Actelion Pharmaceuticals Ltd | Azetidine amide derivatives as orexin receptor antagonists |
| MY179605A (en) | 2013-12-04 | 2020-11-11 | Idorsia Pharmaceuticals Ltd | Use of benzimidazole-proline derivatives |
| US12172944B2 (en) | 2019-03-28 | 2024-12-24 | Council Of Scientific & Industrial Research | Process for the preparation of tapentadol and analogs thereof |
Family Cites Families (9)
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| IL117805A0 (en) * | 1995-04-07 | 1996-08-04 | Schering Corp | Carbonyl piperazinyl and piperidinyl compounds |
| US5880128A (en) * | 1996-05-08 | 1999-03-09 | Schering Corporation | Carbonyl piperazinyl and piperidinyl compounds |
| DE10035908A1 (de) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| DE10035927A1 (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 |
| UA79286C2 (en) * | 2002-06-29 | 2007-06-11 | Zentaris Gmbh | Arylcarbonylpipererazines and heteroarylcarbonylpiperazines and their use in the treatment of benign and malignant tumors |
| WO2004037248A2 (en) * | 2002-10-24 | 2004-05-06 | Carex Sa | Modulation of peroxisome proliferator activated receptors activity |
| GB0228417D0 (en) * | 2002-12-05 | 2003-01-08 | Cancer Rec Tech Ltd | Pyrazole compounds |
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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 TW TW093115885A patent/TW200510344A/zh unknown
- 2004-06-03 CA CA002528093A patent/CA2528093A1/fr not_active Abandoned
- 2004-06-03 WO PCT/FR2004/001379 patent/WO2004108685A1/fr not_active Ceased
- 2004-06-03 KR KR1020057023192A patent/KR20060006850A/ko not_active Ceased
- 2004-06-03 AU AU2004245269A patent/AU2004245269A1/en not_active Abandoned
- 2004-06-03 BR BRPI0411001-3A patent/BRPI0411001A/pt not_active IP Right Cessation
- 2004-06-03 CL CL200401359A patent/CL2004001359A1/es unknown
- 2004-06-03 JP JP2006508355A patent/JP4805813B2/ja not_active Expired - Fee Related
- 2004-06-03 MX MXPA05012929A patent/MXPA05012929A/es active IP Right Grant
- 2004-06-03 US US10/859,740 patent/US20050014765A1/en not_active Abandoned
- 2004-06-03 EP EP04767247A patent/EP1641765A1/fr not_active Withdrawn
- 2004-06-04 UY UY28350A patent/UY28350A1/es unknown
- 2004-06-04 PA PA20048604401A patent/PA8604401A1/es unknown
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2005
- 2005-11-28 IL IL172222A patent/IL172222A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060006850A (ko) | 2006-01-19 |
| TW200510344A (en) | 2005-03-16 |
| PE20050226A1 (es) | 2005-05-18 |
| US20050014765A1 (en) | 2005-01-20 |
| AR044586A1 (es) | 2005-09-21 |
| HK1093339A1 (zh) | 2007-03-02 |
| UY28350A1 (es) | 2004-12-31 |
| PA8604401A1 (es) | 2004-12-16 |
| CA2528093A1 (fr) | 2004-12-16 |
| JP4805813B2 (ja) | 2011-11-02 |
| JP2006526596A (ja) | 2006-11-24 |
| WO2004108685A1 (fr) | 2004-12-16 |
| EP1641765A1 (fr) | 2006-04-05 |
| IL172222A0 (en) | 2011-08-01 |
| CL2004001359A1 (es) | 2005-05-06 |
| BRPI0411001A (pt) | 2006-07-04 |
| MXPA05012929A (es) | 2006-02-28 |
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