JP2006526596A5 - - Google Patents
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- Publication number
- JP2006526596A5 JP2006526596A5 JP2006508355A JP2006508355A JP2006526596A5 JP 2006526596 A5 JP2006526596 A5 JP 2006526596A5 JP 2006508355 A JP2006508355 A JP 2006508355A JP 2006508355 A JP2006508355 A JP 2006508355A JP 2006526596 A5 JP2006526596 A5 JP 2006526596A5
- Authority
- JP
- Japan
- Prior art keywords
- piperazin
- phenyl
- 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.)
- Granted
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- -1 2,3-disubstituted phenyl Chemical group 0.000 claims 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 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 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- AIDJMQKZDVULAF-UHFFFAOYSA-N 1-[3-[4-(3,5-dimethoxyphenyl)piperazine-1-carbonyl]-2-phenylpyrrol-1-yl]ethanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N(C(C)=O)C=C2)C=2C=CC=CC=2)=C1 AIDJMQKZDVULAF-UHFFFAOYSA-N 0.000 claims 1
- HIMQYHWZFQZWAO-UHFFFAOYSA-N 1-methyl-4-phenylpyrrole-3-carbaldehyde Chemical compound CN1C=C(C=O)C(C=2C=CC=CC=2)=C1 HIMQYHWZFQZWAO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- QPQOEAPZMIDYND-UHFFFAOYSA-N 2-methylsulfanyl-4-phenyl-1H-imidazole-5-carbaldehyde Chemical compound CSC=1NC(=C(N1)C1=CC=CC=C1)C=O QPQOEAPZMIDYND-UHFFFAOYSA-N 0.000 claims 1
- AXOISOXQFSFKBI-UHFFFAOYSA-N 2-phenyl-1h-pyrrole-3-carbaldehyde Chemical compound C1=CNC(C=2C=CC=CC=2)=C1C=O AXOISOXQFSFKBI-UHFFFAOYSA-N 0.000 claims 1
- JKPTUXAJNUGFNI-UHFFFAOYSA-N 3-[3-[4-(3-chlorophenyl)piperazine-1-carbonyl]-4-phenylpyrrol-1-yl]propanoic acid Chemical compound C=1C=CC=CC=1C1=CN(CCC(=O)O)C=C1C(=O)N(CC1)CCN1C1=CC=CC(Cl)=C1 JKPTUXAJNUGFNI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- ZNHCXYGJSDERCQ-UHFFFAOYSA-N 3-[4-(2-amino-4-phenyl-1,3-thiazole-5-carbonyl)piperazin-1-yl]benzonitrile Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 ZNHCXYGJSDERCQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GALSDOHLAKFIBA-UHFFFAOYSA-N 3-[4-(2-methylsulfanyl-4-phenyl-1h-imidazole-5-carbonyl)piperazin-1-yl]benzonitrile Chemical compound N1C(SC)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 GALSDOHLAKFIBA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- QSBGOQPVAJOLDM-UHFFFAOYSA-N 3-[4-[1-(1-hydroxyethyl)-2-phenylpyrrole-3-carbonyl]piperazin-1-yl]benzamide Chemical compound C=1C=CC=CC=1C=1N(C(O)C)C=CC=1C(=O)N(CC1)CCN1C1=CC=CC(C(N)=O)=C1 QSBGOQPVAJOLDM-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 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 1
- STZQWSSMWQRLDC-UHFFFAOYSA-N 3-[4-[1-(1-hydroxyethyl)-4-phenylpyrrole-3-carbonyl]piperazin-1-yl]benzonitrile Chemical compound C=1C=CC=CC=1C1=CN(C(O)C)C=C1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 STZQWSSMWQRLDC-UHFFFAOYSA-N 0.000 claims 1
- CPBQHWOZKOBKHX-UHFFFAOYSA-N 3-[4-[1-(hydroxymethyl)-4-phenylpyrrole-3-carbonyl]piperazin-1-yl]benzonitrile Chemical compound C=1C=CC=CC=1C1=CN(CO)C=C1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 CPBQHWOZKOBKHX-UHFFFAOYSA-N 0.000 claims 1
- JTIAFBAAEUDXGG-UHFFFAOYSA-N 3-[4-[2-(2-methoxyethylamino)-4-phenyl-1,3-thiazole-5-carbonyl]piperazin-1-yl]benzamide Chemical compound S1C(NCCOC)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(C(N)=O)=C1 JTIAFBAAEUDXGG-UHFFFAOYSA-N 0.000 claims 1
- ZKWQSWNHKKWJBJ-UHFFFAOYSA-N 3-[4-[4-phenyl-1-(pyridin-3-ylmethyl)pyrrole-3-carbonyl]piperazin-1-yl]benzonitrile Chemical compound C=1N(CC=2C=NC=CC=2)C=C(C=2C=CC=CC=2)C=1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 ZKWQSWNHKKWJBJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- COVMDYQQYPZRGL-UHFFFAOYSA-N 3-[4-[4-phenyl-2-(trifluoromethyl)-1h-imidazole-5-carbonyl]piperazin-1-yl]benzonitrile Chemical compound N1C(C(F)(F)F)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(C#N)=C1 COVMDYQQYPZRGL-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- SAVGMQZMOQMKID-UHFFFAOYSA-N 3-phenylimidazole-4-carbaldehyde Chemical compound O=CC1=CN=CN1C1=CC=CC=C1 SAVGMQZMOQMKID-UHFFFAOYSA-N 0.000 claims 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 claims 1
- XOULNWKRRGEGHW-UHFFFAOYSA-N 4-[4-(3,5-dimethoxyphenyl)piperazine-1-carbonyl]-5-phenyl-1,3-dihydroimidazol-2-one Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(NC(O)=N2)C=2C=CC=CC=2)=C1 XOULNWKRRGEGHW-UHFFFAOYSA-N 0.000 claims 1
- BNWDQWYSAQEDHZ-UHFFFAOYSA-N 4-[4-[3-(hydroxymethyl)phenyl]piperazine-1-carbonyl]-5-phenyl-1,3-dihydroimidazol-2-one Chemical compound OCC1=CC=CC(N2CCN(CC2)C(=O)C2=C(N=C(O)N2)C=2C=CC=CC=2)=C1 BNWDQWYSAQEDHZ-UHFFFAOYSA-N 0.000 claims 1
- XNRFNVMAYPXUOY-UHFFFAOYSA-N 4-phenyl-1h-imidazole-5-carbaldehyde Chemical compound N1=CNC(C=2C=CC=CC=2)=C1C=O XNRFNVMAYPXUOY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- XZRAZBBODBSFKM-UHFFFAOYSA-N [1-(1-hydroxyethyl)-5-phenylpyrrol-2-yl]-[4-[3-(hydroxymethyl)phenyl]piperazin-1-yl]methanone Chemical compound CC(O)N1C(C(=O)N2CCN(CC2)C=2C=C(CO)C=CC=2)=CC=C1C1=CC=CC=C1 XZRAZBBODBSFKM-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 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 1
- 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 1
- XUVYFYAJBKTBLH-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(1-methyl-3-phenylpyrrol-2-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C=2N(C=CC=2C=2C=CC=CC=2)C)=C1 XUVYFYAJBKTBLH-UHFFFAOYSA-N 0.000 claims 1
- IOWVOQBKRVZZTN-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(1-methyl-4-phenylpyrrol-3-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C=2C(=CN(C)C=2)C=2C=CC=CC=2)=C1 IOWVOQBKRVZZTN-UHFFFAOYSA-N 0.000 claims 1
- DCTFAUOATIBRAU-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(2-methoxy-4-phenyl-1,3-thiazol-5-yl)methanone Chemical compound S1C(OC)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC(OC)=CC(OC)=C1 DCTFAUOATIBRAU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- LZEKYSVYSVNYLZ-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(2-methyl-4-phenyl-1h-imidazol-5-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N=C(C)N2)C=2C=CC=CC=2)=C1 LZEKYSVYSVNYLZ-UHFFFAOYSA-N 0.000 claims 1
- IMBCURQZYXRXET-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(2-methylsulfanyl-4-phenyl-1h-imidazol-5-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(NC(SC)=N2)C=2C=CC=CC=2)=C1 IMBCURQZYXRXET-UHFFFAOYSA-N 0.000 claims 1
- YHNLLCBHNKFMHP-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(2-methylsulfinyl-4-phenyl-1h-imidazol-5-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(NC(=N2)S(C)=O)C=2C=CC=CC=2)=C1 YHNLLCBHNKFMHP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- YNEXWIZDNAVXFF-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(3-phenylimidazol-4-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C=2N(C=NC=2)C=2C=CC=CC=2)=C1 YNEXWIZDNAVXFF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- CLVGDIPNPQWNLK-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-(5-phenyl-2-sulfanylidene-1,3-dihydroimidazol-4-yl)methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(NC(S)=N2)C=2C=CC=CC=2)=C1 CLVGDIPNPQWNLK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- HOULBRYZTMTERN-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-[2-phenyl-1-(pyridin-3-ylmethyl)pyrrol-3-yl]methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N(CC=3C=NC=CC=3)C=C2)C=2C=CC=CC=2)=C1 HOULBRYZTMTERN-UHFFFAOYSA-N 0.000 claims 1
- BRIZJOCBJNSECZ-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-[4-phenyl-1-(1,3-thiazol-4-ylmethyl)pyrrol-3-yl]methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C=2C(=CN(CC=3N=CSC=3)C=2)C=2C=CC=CC=2)=C1 BRIZJOCBJNSECZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- XCKUDSAUYUJIDS-UHFFFAOYSA-N [4-(3,5-dimethoxyphenyl)piperazin-1-yl]-[4-phenyl-2-(trifluoromethyl)-1h-imidazol-5-yl]methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)C2=C(N=C(N2)C(F)(F)F)C=2C=CC=CC=2)=C1 XCKUDSAUYUJIDS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- PJLKWFYMRKEDTC-UHFFFAOYSA-N [4-(3-chlorophenyl)piperazin-1-yl]-(1-methyl-3-phenylpyrrol-2-yl)methanone Chemical compound CN1C=CC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(Cl)=C1 PJLKWFYMRKEDTC-UHFFFAOYSA-N 0.000 claims 1
- IYPYJVAROLJHPB-UHFFFAOYSA-N [4-(3-chlorophenyl)piperazin-1-yl]-(1-phenylimidazol-2-yl)methanone Chemical compound ClC1=CC=CC(N2CCN(CC2)C(=O)C=2N(C=CN=2)C=2C=CC=CC=2)=C1 IYPYJVAROLJHPB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- NOYBMSQOHYWIHO-UHFFFAOYSA-N [4-(3-chlorophenyl)piperazin-1-yl]-[1-[2-(dimethylamino)ethyl]-4-phenylpyrrol-3-yl]methanone Chemical compound C=1C=CC=CC=1C1=CN(CCN(C)C)C=C1C(=O)N(CC1)CCN1C1=CC=CC(Cl)=C1 NOYBMSQOHYWIHO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WQCNPOUJOFYEEP-UHFFFAOYSA-N [4-[3-(difluoromethoxy)phenyl]piperazin-1-yl]-(4-phenyl-1h-imidazol-5-yl)methanone Chemical compound FC(F)OC1=CC=CC(N2CCN(CC2)C(=O)C2=C(NC=N2)C=2C=CC=CC=2)=C1 WQCNPOUJOFYEEP-UHFFFAOYSA-N 0.000 claims 1
- VTROQPHHULZPBJ-UHFFFAOYSA-N [4-[3-(hydroxymethyl)phenyl]piperazin-1-yl]-(1-methyl-2-phenylpyrrol-3-yl)methanone Chemical compound C=1C=CC=CC=1C=1N(C)C=CC=1C(=O)N(CC1)CCN1C1=CC=CC(CO)=C1 VTROQPHHULZPBJ-UHFFFAOYSA-N 0.000 claims 1
- QXTKRXQYPQHSSO-UHFFFAOYSA-N [4-[3-(hydroxymethyl)phenyl]piperazin-1-yl]-(2-methyl-4-phenyl-1h-imidazol-5-yl)methanone Chemical compound N1C(C)=NC(C=2C=CC=CC=2)=C1C(=O)N(CC1)CCN1C1=CC=CC(CO)=C1 QXTKRXQYPQHSSO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- QNFTVJGCGFUGQZ-UHFFFAOYSA-N [4-[3-(hydroxymethyl)phenyl]piperazin-1-yl]-(5-phenyl-2-sulfanylidene-1,3-dihydroimidazol-4-yl)methanone Chemical compound OCC1=CC=CC(N2CCN(CC2)C(=O)C2=C(N=C(S)N2)C=2C=CC=CC=2)=C1 QNFTVJGCGFUGQZ-UHFFFAOYSA-N 0.000 claims 1
- IPPYKVVIHANXTQ-UHFFFAOYSA-N [4-[3-(hydroxymethyl)phenyl]piperazin-1-yl]-[4-phenyl-2-(trifluoromethyl)-1h-imidazol-5-yl]methanone Chemical compound OCC1=CC=CC(N2CCN(CC2)C(=O)C2=C(N=C(N2)C(F)(F)F)C=2C=CC=CC=2)=C1 IPPYKVVIHANXTQ-UHFFFAOYSA-N 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 229940017219 methyl propionate Drugs 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 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 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 210000004881 tumor cell Anatomy 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
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| 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 |
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| JP2006526596A JP2006526596A (ja) | 2006-11-24 |
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| EP (1) | EP1641765A1 (OSRAM) |
| JP (1) | JP4805813B2 (OSRAM) |
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| 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
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- 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
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