JP2006508946A5 - - Google Patents
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- Publication number
- JP2006508946A5 JP2006508946A5 JP2004549775A JP2004549775A JP2006508946A5 JP 2006508946 A5 JP2006508946 A5 JP 2006508946A5 JP 2004549775 A JP2004549775 A JP 2004549775A JP 2004549775 A JP2004549775 A JP 2004549775A JP 2006508946 A5 JP2006508946 A5 JP 2006508946A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- methyl
- piperazin
- amino
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 95
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 32
- 229910052736 halogen Inorganic materials 0.000 claims 29
- 150000002367 halogens Chemical class 0.000 claims 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 27
- -1 N-oxide-pyridyl Chemical group 0.000 claims 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 10
- 238000000034 method Methods 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 241001465754 Metazoa Species 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000006308 propyl amino group Chemical group 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- RRAYRDYHMPXQLI-MUUNZHRXSA-N 4-[(r)-[3-(cyclohexylmethylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NCC2CCCCC2)C=CC=1)N1CCNCC1 RRAYRDYHMPXQLI-MUUNZHRXSA-N 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims 2
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- UUYHNFNKZRWURL-XMMPIXPASA-N 4-[(r)-(3-aminophenyl)-(4-prop-2-enylpiperazin-1-yl)methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(N)C=CC=1)N1CCN(CC=C)CC1 UUYHNFNKZRWURL-XMMPIXPASA-N 0.000 claims 1
- CKCOKPJMRUXJIT-XMMPIXPASA-N 4-[(r)-(3-aminophenyl)-[4-(2-methoxyethyl)piperazin-1-yl]methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(N)C=CC=1)N1CCN(CCOC)CC1 CKCOKPJMRUXJIT-XMMPIXPASA-N 0.000 claims 1
- VNMWHLNQUGAGSL-RUZDIDTESA-N 4-[(r)-(3-aminophenyl)-[4-(3-methoxypropyl)piperazin-1-yl]methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(N)C=CC=1)N1CCN(CCCOC)CC1 VNMWHLNQUGAGSL-RUZDIDTESA-N 0.000 claims 1
- JVSRZEWEFIGJJD-AREMUKBSSA-N 4-[(r)-(3-aminophenyl)-[4-(3-methylbut-2-enyl)piperazin-1-yl]methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(N)C=CC=1)N1CCN(CC=C(C)C)CC1 JVSRZEWEFIGJJD-AREMUKBSSA-N 0.000 claims 1
- ICSHUTBTVCGHDN-RUZDIDTESA-N 4-[(r)-(3-aminophenyl)-[4-(cyclopropylmethyl)piperazin-1-yl]methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(N)C=CC=1)N1CCN(CC2CC2)CC1 ICSHUTBTVCGHDN-RUZDIDTESA-N 0.000 claims 1
- NTEGLMNCNOQQCS-HHHXNRCGSA-N 4-[(r)-(3-benzamidophenyl)-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NC(=O)C=2C=CC=CC=2)C=CC=1)N1CCNCC1 NTEGLMNCNOQQCS-HHHXNRCGSA-N 0.000 claims 1
- AKONSTOBSSYIDF-PGUFJCEWSA-N 4-[(r)-[3-(2,2-diphenylethylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1)N1CCNCC1 AKONSTOBSSYIDF-PGUFJCEWSA-N 0.000 claims 1
- ANMCFJSYWZPTJG-HHHXNRCGSA-N 4-[(r)-[3-(3-chloroanilino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NC=2C=C(Cl)C=CC=2)C=CC=1)N1CCNCC1 ANMCFJSYWZPTJG-HHHXNRCGSA-N 0.000 claims 1
- ZHKMBQODOBEUGR-MUUNZHRXSA-N 4-[(r)-[3-(benzylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NCC=2C=CC=CC=2)C=CC=1)N1CCNCC1 ZHKMBQODOBEUGR-MUUNZHRXSA-N 0.000 claims 1
- ZAQFHTXVYZENHP-MUUNZHRXSA-N 4-[(r)-[3-(benzylsulfonylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NS(=O)(=O)CC=2C=CC=CC=2)C=CC=1)N1CCNCC1 ZAQFHTXVYZENHP-MUUNZHRXSA-N 0.000 claims 1
- NDUYIWYLBBVSAX-MUUNZHRXSA-N 4-[(r)-[3-(cycloheptylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NC2CCCCCC2)C=CC=1)N1CCNCC1 NDUYIWYLBBVSAX-MUUNZHRXSA-N 0.000 claims 1
- WQLHIDDQIANXGE-HHHXNRCGSA-N 4-[(r)-[3-(cyclohexanecarbonylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NC(=O)C2CCCCC2)C=CC=1)N1CCNCC1 WQLHIDDQIANXGE-HHHXNRCGSA-N 0.000 claims 1
- VOBVMGMKZPHTKR-MUUNZHRXSA-N 4-[(r)-[3-(cyclohexen-1-ylmethylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NCC=2CCCCC=2)C=CC=1)N1CCNCC1 VOBVMGMKZPHTKR-MUUNZHRXSA-N 0.000 claims 1
- DZGWIUIXURMXJY-SSEXGKCCSA-N 4-[(r)-[3-(cyclononylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NC2CCCCCCCC2)C=CC=1)N1CCNCC1 DZGWIUIXURMXJY-SSEXGKCCSA-N 0.000 claims 1
- MCFCJCQGTREGKV-GDLZYMKVSA-N 4-[(r)-[3-(cyclooctylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NC2CCCCCCC2)C=CC=1)N1CCNCC1 MCFCJCQGTREGKV-GDLZYMKVSA-N 0.000 claims 1
- VORWYXRBCXAJNO-AREMUKBSSA-N 4-[(r)-[3-(cyclopentylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NC2CCCC2)C=CC=1)N1CCNCC1 VORWYXRBCXAJNO-AREMUKBSSA-N 0.000 claims 1
- AZUFJWYSVWBTOD-HHHXNRCGSA-N 4-[(r)-[3-(cyclopentylmethylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NCC2CCCC2)C=CC=1)N1CCNCC1 AZUFJWYSVWBTOD-HHHXNRCGSA-N 0.000 claims 1
- NREVMTYXSGBORD-HHHXNRCGSA-N 4-[(r)-[3-(dipropylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound CCCN(CCC)C1=CC=CC([C@H](N2CCNCC2)C=2C=CC(=CC=2)C(=O)N(CC)CC)=C1 NREVMTYXSGBORD-HHHXNRCGSA-N 0.000 claims 1
- ODPLMQZATCIDQO-GDLZYMKVSA-N 4-[(r)-[3-[(2-cyclohexylacetyl)amino]phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NC(=O)CC2CCCCC2)C=CC=1)N1CCNCC1 ODPLMQZATCIDQO-GDLZYMKVSA-N 0.000 claims 1
- ZWGDIWYQUGQZJF-WJOKGBTCSA-N 4-[(r)-[3-[(4-tert-butylphenyl)methylamino]phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NCC=2C=CC(=CC=2)C(C)(C)C)C=CC=1)N1CCNCC1 ZWGDIWYQUGQZJF-WJOKGBTCSA-N 0.000 claims 1
- GERQFUCWGJLZED-MUUNZHRXSA-N 4-[(r)-[3-[cyclohexyl(methyl)amino]phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(C=CC=1)N(C)C1CCCCC1)N1CCNCC1 GERQFUCWGJLZED-MUUNZHRXSA-N 0.000 claims 1
- IUJKTWYUTMICTH-SSEXGKCCSA-N 4-[(r)-[4-(cyclopropylmethyl)piperazin-1-yl]-[3-(thiophen-2-ylmethylamino)phenyl]methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NCC=2SC=CC=2)C=CC=1)N1CCN(CC2CC2)CC1 IUJKTWYUTMICTH-SSEXGKCCSA-N 0.000 claims 1
- NTEGLMNCNOQQCS-MHZLTWQESA-N 4-[(s)-(3-benzamidophenyl)-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NC(=O)C=2C=CC=CC=2)C=CC=1)N1CCNCC1 NTEGLMNCNOQQCS-MHZLTWQESA-N 0.000 claims 1
- ANMCFJSYWZPTJG-MHZLTWQESA-N 4-[(s)-[3-(3-chloroanilino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NC=2C=C(Cl)C=CC=2)C=CC=1)N1CCNCC1 ANMCFJSYWZPTJG-MHZLTWQESA-N 0.000 claims 1
- ZHKMBQODOBEUGR-NDEPHWFRSA-N 4-[(s)-[3-(benzylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NCC=2C=CC=CC=2)C=CC=1)N1CCNCC1 ZHKMBQODOBEUGR-NDEPHWFRSA-N 0.000 claims 1
- NDUYIWYLBBVSAX-NDEPHWFRSA-N 4-[(s)-[3-(cycloheptylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NC2CCCCCC2)C=CC=1)N1CCNCC1 NDUYIWYLBBVSAX-NDEPHWFRSA-N 0.000 claims 1
- WQLHIDDQIANXGE-MHZLTWQESA-N 4-[(s)-[3-(cyclohexanecarbonylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NC(=O)C2CCCCC2)C=CC=1)N1CCNCC1 WQLHIDDQIANXGE-MHZLTWQESA-N 0.000 claims 1
- CCQTVJHCBBIJEX-LJAQVGFWSA-N 4-[(s)-[3-(cyclohexylamino)phenyl]-(4-ethylpiperazin-1-yl)methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NC2CCCCC2)C=CC=1)N1CCN(CC)CC1 CCQTVJHCBBIJEX-LJAQVGFWSA-N 0.000 claims 1
- XJLWLNNQQSHWTC-HKBQPEDESA-N 4-[(s)-[3-(cyclohexylamino)phenyl]-[4-(cyclopropylmethyl)piperazin-1-yl]methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NC2CCCCC2)C=CC=1)N1CCN(CC2CC2)CC1 XJLWLNNQQSHWTC-HKBQPEDESA-N 0.000 claims 1
- RYLFIIKXWMBOST-MHZLTWQESA-N 4-[(s)-[3-(cyclohexylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NC2CCCCC2)C=CC=1)N1CCNCC1 RYLFIIKXWMBOST-MHZLTWQESA-N 0.000 claims 1
- RRAYRDYHMPXQLI-NDEPHWFRSA-N 4-[(s)-[3-(cyclohexylmethylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NCC2CCCCC2)C=CC=1)N1CCNCC1 RRAYRDYHMPXQLI-NDEPHWFRSA-N 0.000 claims 1
- MCFCJCQGTREGKV-LJAQVGFWSA-N 4-[(s)-[3-(cyclooctylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NC2CCCCCCC2)C=CC=1)N1CCNCC1 MCFCJCQGTREGKV-LJAQVGFWSA-N 0.000 claims 1
- NREVMTYXSGBORD-MHZLTWQESA-N 4-[(s)-[3-(dipropylamino)phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound CCCN(CCC)C1=CC=CC([C@@H](N2CCNCC2)C=2C=CC(=CC=2)C(=O)N(CC)CC)=C1 NREVMTYXSGBORD-MHZLTWQESA-N 0.000 claims 1
- ODPLMQZATCIDQO-LJAQVGFWSA-N 4-[(s)-[3-[(2-cyclohexylacetyl)amino]phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NC(=O)CC2CCCCC2)C=CC=1)N1CCNCC1 ODPLMQZATCIDQO-LJAQVGFWSA-N 0.000 claims 1
- GERQFUCWGJLZED-NDEPHWFRSA-N 4-[(s)-[3-[cyclohexyl(methyl)amino]phenyl]-piperazin-1-ylmethyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(C=CC=1)N(C)C1CCCCC1)N1CCNCC1 GERQFUCWGJLZED-NDEPHWFRSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 208000027520 Somatoform disease Diseases 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- AQJJNADLVMPTFV-GDLZYMKVSA-N n,n-diethyl-4-[(r)-(4-prop-2-enylpiperazin-1-yl)-[3-(thiophen-2-ylmethylamino)phenyl]methyl]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NCC=2SC=CC=2)C=CC=1)N1CCN(CC=C)CC1 AQJJNADLVMPTFV-GDLZYMKVSA-N 0.000 claims 1
- VWLXSEDNQYLOGT-HHHXNRCGSA-N n,n-diethyl-4-[(r)-[3-(2-fluoroanilino)phenyl]-piperazin-1-ylmethyl]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NC=2C(=CC=CC=2)F)C=CC=1)N1CCNCC1 VWLXSEDNQYLOGT-HHHXNRCGSA-N 0.000 claims 1
- LYBVJDSAURIACO-SSEXGKCCSA-N n,n-diethyl-4-[(r)-[3-(3-phenylpropanoylamino)phenyl]-piperazin-1-ylmethyl]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NC(=O)CCC=2C=CC=CC=2)C=CC=1)N1CCNCC1 LYBVJDSAURIACO-SSEXGKCCSA-N 0.000 claims 1
- FBFBZLLDTVMDFZ-HHHXNRCGSA-N n,n-diethyl-4-[(r)-[3-(phenylcarbamothioylamino)phenyl]-piperazin-1-ylmethyl]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NC(=S)NC=2C=CC=CC=2)C=CC=1)N1CCNCC1 FBFBZLLDTVMDFZ-HHHXNRCGSA-N 0.000 claims 1
- YYNJNAARQPIQDM-HHHXNRCGSA-N n,n-diethyl-4-[(r)-[3-(phenylcarbamoylamino)phenyl]-piperazin-1-ylmethyl]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NC(=O)NC=2C=CC=CC=2)C=CC=1)N1CCNCC1 YYNJNAARQPIQDM-HHHXNRCGSA-N 0.000 claims 1
- CZVFLBAEMPPBFJ-HHHXNRCGSA-N n,n-diethyl-4-[(r)-[4-(2-methoxyethyl)piperazin-1-yl]-[3-(propylamino)phenyl]methyl]benzamide Chemical compound CCCNC1=CC=CC([C@H](N2CCN(CCOC)CC2)C=2C=CC(=CC=2)C(=O)N(CC)CC)=C1 CZVFLBAEMPPBFJ-HHHXNRCGSA-N 0.000 claims 1
- RGEVDNSJLQSNSH-MUUNZHRXSA-N n,n-diethyl-4-[(r)-[4-(3-methoxypropyl)piperazin-1-yl]-[3-(propylamino)phenyl]methyl]benzamide Chemical compound CCCNC1=CC=CC([C@H](N2CCN(CCCOC)CC2)C=2C=CC(=CC=2)C(=O)N(CC)CC)=C1 RGEVDNSJLQSNSH-MUUNZHRXSA-N 0.000 claims 1
- UYERMSXLGPDORF-WJOKGBTCSA-N n,n-diethyl-4-[(r)-[4-(3-methylbut-2-enyl)piperazin-1-yl]-[3-(thiophen-2-ylmethylamino)phenyl]methyl]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(NCC=2SC=CC=2)C=CC=1)N1CCN(CC=C(C)C)CC1 UYERMSXLGPDORF-WJOKGBTCSA-N 0.000 claims 1
- VWLXSEDNQYLOGT-MHZLTWQESA-N n,n-diethyl-4-[(s)-[3-(2-fluoroanilino)phenyl]-piperazin-1-ylmethyl]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NC=2C(=CC=CC=2)F)C=CC=1)N1CCNCC1 VWLXSEDNQYLOGT-MHZLTWQESA-N 0.000 claims 1
- LYBVJDSAURIACO-PMERELPUSA-N n,n-diethyl-4-[(s)-[3-(3-phenylpropanoylamino)phenyl]-piperazin-1-ylmethyl]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NC(=O)CCC=2C=CC=CC=2)C=CC=1)N1CCNCC1 LYBVJDSAURIACO-PMERELPUSA-N 0.000 claims 1
- SUIZQFSAOBAKES-HKBQPEDESA-N n,n-diethyl-4-[(s)-[3-[(4-imidazol-1-ylphenyl)methylamino]phenyl]-piperazin-1-ylmethyl]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NCC=2C=CC(=CC=2)N2C=NC=C2)C=CC=1)N1CCNCC1 SUIZQFSAOBAKES-HKBQPEDESA-N 0.000 claims 1
- QTSPCJUTPKIPCS-XIFFEERXSA-N n,n-diethyl-4-[(s)-piperazin-1-yl-[3-[(4-pyridin-3-ylphenyl)methylamino]phenyl]methyl]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1[C@@H](C=1C=C(NCC=2C=CC(=CC=2)C=2C=NC=CC=2)C=CC=1)N1CCNCC1 QTSPCJUTPKIPCS-XIFFEERXSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 208000027753 pain disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 0 CCN(CC)C(c1ccc(*)cc1)=O Chemical compound CCN(CC)C(c1ccc(*)cc1)=O 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0203302A SE0203302D0 (sv) | 2002-11-07 | 2002-11-07 | Novel Compounds |
| PCT/SE2003/001706 WO2004041801A1 (en) | 2002-11-07 | 2003-11-05 | 4(phenyl-piperazinyl-methyl) benzamide derivatives and their use for the treatment of pain or gastrointestinal disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006508946A JP2006508946A (ja) | 2006-03-16 |
| JP2006508946A5 true JP2006508946A5 (https=) | 2006-09-28 |
| JP4527542B2 JP4527542B2 (ja) | 2010-08-18 |
Family
ID=20289506
Family Applications (1)
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|---|---|---|---|
| JP2004549775A Expired - Fee Related JP4527542B2 (ja) | 2002-11-07 | 2003-11-05 | ４（フェニル−ピペラジニル−メチル）ベンズアミド誘導体、および疼痛または胃腸障害の治療のためのその使用 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7241764B2 (https=) |
| EP (1) | EP1562923B1 (https=) |
| JP (1) | JP4527542B2 (https=) |
| AR (1) | AR041896A1 (https=) |
| AT (1) | ATE362923T1 (https=) |
| AU (1) | AU2003278664A1 (https=) |
| DE (1) | DE60314003T2 (https=) |
| ES (1) | ES2286474T3 (https=) |
| SE (1) | SE0203302D0 (https=) |
| TW (1) | TW200418813A (https=) |
| WO (1) | WO2004041801A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1395567E (pt) | 2001-05-18 | 2009-03-26 | Astrazeneca Ab | Derivados de 4(fenil-piperazinil-metil)benzamida e sua utilização para o tratamento da ansiedade da dor ou de distúrbios gastrointestinais |
| SE0203301D0 (sv) * | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
| SE0203303D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
| SE0203300D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
| SE0203302D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
| NZ546834A (en) | 2003-10-01 | 2010-03-26 | Adolor Corp | Spirocyclic heterocyclic derivatives and methods of their use |
| KR101234421B1 (ko) | 2004-08-02 | 2013-02-18 | 아스트라제네카 아베 | 디아릴메틸 피페라진 유도체, 이의 제조 방법 및 용도 |
| SE0401968D0 (sv) * | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Diarylmethyl piperazine derivatives, preparations thereof and uses thereof |
| US7598261B2 (en) | 2005-03-31 | 2009-10-06 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| US7576207B2 (en) | 2006-04-06 | 2009-08-18 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| MX2009000110A (es) * | 2006-06-28 | 2009-01-23 | Glaxo Group Ltd | Derivados de piperazinilo utiles en el tratamiento de enfermedades mediadas por el receptor grp38. |
| US20090291966A1 (en) * | 2008-05-20 | 2009-11-26 | Astrazeneca Ab | Method Of Treating Anxious Major Depressive Disorder |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH583713A5 (https=) * | 1973-06-29 | 1977-01-14 | Cermol Sa | |
| DE2900810A1 (de) | 1979-01-11 | 1980-07-24 | Cassella Ag | Substituierte n-benzhydryl-n'-p- hydroxybenzyl-piperazine und verfahren zu ihrer herstellung |
| IT1140978B (it) | 1980-05-23 | 1986-10-10 | Selvi & C Spa | 1-(4-clorobenzidril)-4-(2,3-diidros sipropil)-piperazina, metodi per la sua preparazione e relative composizione farmaceutiche |
| GB8320701D0 (en) | 1983-08-01 | 1983-09-01 | Wellcome Found | Chemotherapeutic agent |
| IT1196150B (it) | 1984-06-19 | 1988-11-10 | Poli Ind Chimica Spa | Derivati di 1-(bis-(4-fluorofenil)metil)-4-(3-fenil-2-propenil)-esaidro-1h-1,4-diazepina ad attivita' calcio antagonista,sua preparazione e composizioni che lo contengono |
| SE8500573D0 (sv) | 1985-02-08 | 1985-02-08 | Ferrosan Ab | Novel piperazinecarboxamides having a phenoxyalkyl or thiophenoxyalkyl side chain |
| US5028610A (en) | 1987-03-18 | 1991-07-02 | Sankyo Company Limited | N-benzhydryl-substituted heterocyclic derivatives, their preparation and their use |
| US4829065A (en) | 1987-04-24 | 1989-05-09 | Syntex Pharmaceuticals, Ltd. | Substituted imidazolyl-alkyl-piperazine and -diazepine derivatives |
| US4826844A (en) | 1987-09-30 | 1989-05-02 | American Home Products Corporation | Substituted 1-(aralkyl-piperazinoalkyl) cycloalkanols |
| EP0455789B1 (en) | 1989-11-22 | 1994-03-16 | Janssen Pharmaceutica N.V. | Method of preventing or limiting reperfusion damage |
| DK0546102T3 (da) | 1990-08-29 | 1998-06-02 | Upjohn Co | Tropolonderivater og farmaceutisk sammensætning deraf til hindring og behandling af iskæmiske sygdomme |
| GB9202238D0 (en) | 1992-02-03 | 1992-03-18 | Wellcome Found | Compounds |
| US5807858A (en) * | 1996-06-05 | 1998-09-15 | Delta Pharmaceutical, Inc. | Compositions and methods for reducing respiratory depression |
| US5681830A (en) * | 1992-02-03 | 1997-10-28 | Delta Pharmaceuticals, Inc. | Opioid compounds |
| US5985880A (en) * | 1996-06-05 | 1999-11-16 | Delta Pharmaceuticals | Compositions and methods for reducing respiratory depression and attendant side effects of mu opioid compounds |
| US5574159A (en) * | 1992-02-03 | 1996-11-12 | Delta Pharmaceuticals, Inc. | Opioid compounds and methods for making therefor |
| FR2696744B1 (fr) | 1992-10-12 | 1994-12-30 | Logeais Labor Jacques | Dérivés de 2-pyrrolidone, leur procédé de préparation et leurs applications en thérapeutique. |
| RU2124511C1 (ru) | 1993-05-14 | 1999-01-10 | Фармасьютикал Ко., Лтд | Производные пиперазина |
| PT711289E (pt) | 1993-07-30 | 2001-02-28 | Delta Pharmaceuticals Inc | Compostos piperazina utilizados em terapia |
| JP3352184B2 (ja) | 1993-11-12 | 2002-12-03 | 株式会社アズウェル | ピペラジン不飽和脂肪酸誘導体 |
| SE9504661D0 (sv) * | 1995-12-22 | 1995-12-22 | Astra Pharma Inc | New compounds |
| TW548271B (en) | 1996-12-20 | 2003-08-21 | Astra Pharma Inc | Novel piperidine derivatives having an exocyclic double bond with analgesic effects |
| SE9604786D0 (sv) | 1996-12-20 | 1996-12-20 | Astra Pharma Inc | New compounds |
| EP1049676B1 (en) | 1997-12-24 | 2005-10-12 | Ortho-Mcneil Pharmaceutical, Inc. | 4- aryl(piperidin-4-yl)] aminobenzamides which bind to the delta-opioid receptor |
| US6011035A (en) * | 1998-06-30 | 2000-01-04 | Neuromed Technologies Inc. | Calcium channel blockers |
| HN1999000149A (es) * | 1998-09-09 | 2000-01-12 | Pfizer Prod Inc | Derivados de 4,4-biarilpiperidina |
| SE9904673D0 (sv) | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
| SE9904674D0 (sv) | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
| SE0001209D0 (sv) * | 2000-04-04 | 2000-04-04 | Astrazeneca Canada Inc | Novel compounds |
| PT1395567E (pt) * | 2001-05-18 | 2009-03-26 | Astrazeneca Ab | Derivados de 4(fenil-piperazinil-metil)benzamida e sua utilização para o tratamento da ansiedade da dor ou de distúrbios gastrointestinais |
| SE0103313D0 (sv) | 2001-10-03 | 2001-10-03 | Astrazeneca Ab | Novel compounds |
| SE0203303D0 (sv) * | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
| SE0203300D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
| SE0203302D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
| SE0400027D0 (sv) | 2004-01-09 | 2004-01-09 | Astrazeneca Ab | Diarylmethyl piperazine derivatives, preparations thereof and uses thereof |
| SE0401968D0 (sv) * | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Diarylmethyl piperazine derivatives, preparations thereof and uses thereof |
-
2002
- 2002-11-07 SE SE0203302A patent/SE0203302D0/xx unknown
-
2003
- 2003-11-04 TW TW092130829A patent/TW200418813A/zh unknown
- 2003-11-05 WO PCT/SE2003/001706 patent/WO2004041801A1/en not_active Ceased
- 2003-11-05 AU AU2003278664A patent/AU2003278664A1/en not_active Abandoned
- 2003-11-05 AT AT03770197T patent/ATE362923T1/de not_active IP Right Cessation
- 2003-11-05 AR ARP030104054A patent/AR041896A1/es not_active Application Discontinuation
- 2003-11-05 DE DE60314003T patent/DE60314003T2/de not_active Expired - Lifetime
- 2003-11-05 ES ES03770197T patent/ES2286474T3/es not_active Expired - Lifetime
- 2003-11-05 JP JP2004549775A patent/JP4527542B2/ja not_active Expired - Fee Related
- 2003-11-05 US US10/533,764 patent/US7241764B2/en not_active Expired - Fee Related
- 2003-11-05 EP EP03770197A patent/EP1562923B1/en not_active Expired - Lifetime
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