JP2011500679A5 - - Google Patents
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- Publication number
- JP2011500679A5 JP2011500679A5 JP2010529937A JP2010529937A JP2011500679A5 JP 2011500679 A5 JP2011500679 A5 JP 2011500679A5 JP 2010529937 A JP2010529937 A JP 2010529937A JP 2010529937 A JP2010529937 A JP 2010529937A JP 2011500679 A5 JP2011500679 A5 JP 2011500679A5
- Authority
- JP
- Japan
- Prior art keywords
- ethanamine
- methyl
- phenyl
- pyrazol
- pharmaceutical composition
- 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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- 239000008194 pharmaceutical composition Substances 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- -1 (3-chlorophenyl) -N-({1- [4- (trifluoromethyl) phenyl] -1H-pyrazol-3-yl} methyl) ethanamine Chemical compound 0.000 claims 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- IYWUSTZOQHHTTC-SNVBAGLBSA-N (1r)-1-(3-methoxyphenyl)-n-(1,3-thiazol-2-ylmethyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2SC=CN=2)=C1 IYWUSTZOQHHTTC-SNVBAGLBSA-N 0.000 claims 2
- GBRSAEHLQSBSGR-CQSZACIVSA-N (1r)-1-(4-methoxyphenyl)-n-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]ethanamine Chemical compound C1=CC(OC)=CC=C1[C@@H](C)NCC1=C(C)ON=C1C1=CC=CC=C1 GBRSAEHLQSBSGR-CQSZACIVSA-N 0.000 claims 2
- WIHUTMDCVXPBHB-MRXNPFEDSA-N (1r)-1-naphthalen-1-yl-n-[(2-phenyl-1,3-thiazol-4-yl)methyl]ethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(N=1)=CSC=1C1=CC=CC=C1 WIHUTMDCVXPBHB-MRXNPFEDSA-N 0.000 claims 2
- ULQGKCGFKITLFK-CQSZACIVSA-N (1r)-1-phenyl-n-[(2-phenyl-1,3-thiazol-4-yl)methyl]ethanamine Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(N=1)=CSC=1C1=CC=CC=C1 ULQGKCGFKITLFK-CQSZACIVSA-N 0.000 claims 2
- IHQFMTVQRNOMGB-MRXNPFEDSA-N (1r)-n-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-1-naphthalen-1-ylethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC1=C(C)ON=C1C1=CC=CC=C1 IHQFMTVQRNOMGB-MRXNPFEDSA-N 0.000 claims 2
- LQGMRDRGIYAQTP-CQSZACIVSA-N (1r)-n-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-1-phenylethanamine Chemical compound N([C@H](C)C=1C=CC=CC=1)CC1=C(C)ON=C1C1=CC=CC=C1 LQGMRDRGIYAQTP-CQSZACIVSA-N 0.000 claims 2
- QBBASZPHZLDKNJ-CQSZACIVSA-N (1r)-n-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl]-1-(4-methylphenyl)ethanamine Chemical compound N([C@H](C)C=1C=CC(C)=CC=1)CC(N=1)=CSC=1C1=CC=C(Cl)C=C1 QBBASZPHZLDKNJ-CQSZACIVSA-N 0.000 claims 2
- HYHIOQBDNXMQAK-OAHLLOKOSA-N (1r)-n-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl]-1-naphthalen-1-ylethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(N=1)=CSC=1C1=CC=C(Cl)C=C1 HYHIOQBDNXMQAK-OAHLLOKOSA-N 0.000 claims 2
- KFBRHTDRSGYBHW-OAHLLOKOSA-N (1r)-n-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl]-1-naphthalen-2-ylethanamine Chemical compound N([C@H](C)C=1C=C2C=CC=CC2=CC=1)CC(N=1)=CSC=1C1=CC=C(Cl)C=C1 KFBRHTDRSGYBHW-OAHLLOKOSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- RWGKXZWVCMNMFB-ZIAGYGMSSA-N (1r)-1-(3-chlorophenyl)-n-[(1r)-1-[1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]ethyl]ethanamine Chemical compound C1([C@@H](C)N[C@H](C)C2=NN(C=C2)C=2C=CC(=CC=2)C(F)(F)F)=CC=CC(Cl)=C1 RWGKXZWVCMNMFB-ZIAGYGMSSA-N 0.000 claims 1
- HMDSIQLCKCUAPJ-KWCCSABGSA-N (1r)-1-(3-chlorophenyl)-n-[1-[1-(3-chlorophenyl)-5-methoxypyrazol-3-yl]ethyl]ethanamine Chemical compound COC1=CC(C(C)N[C@H](C)C=2C=C(Cl)C=CC=2)=NN1C1=CC=CC(Cl)=C1 HMDSIQLCKCUAPJ-KWCCSABGSA-N 0.000 claims 1
- IGAOIMCWHVGWEL-KWCCSABGSA-N (1r)-1-(3-chlorophenyl)-n-[1-[5-methoxy-1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]ethyl]ethanamine Chemical compound COC1=CC(C(C)N[C@H](C)C=2C=C(Cl)C=CC=2)=NN1C1=CC=C(C(F)(F)F)C=C1 IGAOIMCWHVGWEL-KWCCSABGSA-N 0.000 claims 1
- PQABFCKYZKXUCA-PZORYLMUSA-N (1r)-1-(3-chlorophenyl)-n-[1-[5-methoxy-1-[6-(trifluoromethyl)pyridin-3-yl]pyrazol-3-yl]ethyl]ethanamine Chemical compound COC1=CC(C(C)N[C@H](C)C=2C=C(Cl)C=CC=2)=NN1C1=CC=C(C(F)(F)F)N=C1 PQABFCKYZKXUCA-PZORYLMUSA-N 0.000 claims 1
- PIOMUHHKNVDAOX-GICMACPYSA-N (1r)-1-(3-chlorophenyl)-n-[[1-(4-fluorophenyl)pyrrolidin-3-yl]methyl]ethanamine Chemical compound N([C@H](C)C=1C=C(Cl)C=CC=1)CC(C1)CCN1C1=CC=C(F)C=C1 PIOMUHHKNVDAOX-GICMACPYSA-N 0.000 claims 1
- NMGDKOAGNWGHKG-CYBMUJFWSA-N (1r)-1-(3-chlorophenyl)-n-[[5-methoxy-1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]methyl]ethanamine Chemical compound C1([C@@H](C)NCC=2C=C(N(N=2)C=2C=CC(=CC=2)C(F)(F)F)OC)=CC=CC(Cl)=C1 NMGDKOAGNWGHKG-CYBMUJFWSA-N 0.000 claims 1
- JRFQQSNSQWCOSE-ZIAGYGMSSA-N (1r)-1-(3-fluorophenyl)-n-[(1r)-1-[1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]ethyl]ethanamine Chemical compound C1([C@@H](C)N[C@H](C)C2=NN(C=C2)C=2C=CC(=CC=2)C(F)(F)F)=CC=CC(F)=C1 JRFQQSNSQWCOSE-ZIAGYGMSSA-N 0.000 claims 1
- JRFQQSNSQWCOSE-KWCCSABGSA-N (1r)-1-(3-fluorophenyl)-n-[1-[1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]ethyl]ethanamine Chemical compound C1([C@@H](C)NC(C)C2=NN(C=C2)C=2C=CC(=CC=2)C(F)(F)F)=CC=CC(F)=C1 JRFQQSNSQWCOSE-KWCCSABGSA-N 0.000 claims 1
- BZVPLOCAXOMDOC-KWCCSABGSA-N (1r)-1-(3-fluorophenyl)-n-[1-[5-methoxy-1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]ethyl]ethanamine Chemical compound COC1=CC(C(C)N[C@H](C)C=2C=C(F)C=CC=2)=NN1C1=CC=C(C(F)(F)F)C=C1 BZVPLOCAXOMDOC-KWCCSABGSA-N 0.000 claims 1
- LXGJGJNLXRKFOY-CYBMUJFWSA-N (1r)-1-(3-fluorophenyl)-n-[[5-methoxy-1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]methyl]ethanamine Chemical compound C1([C@@H](C)NCC=2C=C(N(N=2)C=2C=CC(=CC=2)C(F)(F)F)OC)=CC=CC(F)=C1 LXGJGJNLXRKFOY-CYBMUJFWSA-N 0.000 claims 1
- QJVRHVDDJRPWJK-LLVKDONJSA-N (1r)-1-(3-methoxyphenyl)-n-(1h-pyrrol-2-ylmethyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2NC=CC=2)=C1 QJVRHVDDJRPWJK-LLVKDONJSA-N 0.000 claims 1
- JIXRAHPWSVVJSI-GFCCVEGCSA-N (1r)-1-(3-methoxyphenyl)-n-[(1-methylpyrrol-2-yl)methyl]ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2N(C=CC=2)C)=C1 JIXRAHPWSVVJSI-GFCCVEGCSA-N 0.000 claims 1
- AIUQUXSKVQGGPJ-CQSZACIVSA-N (1r)-1-(3-methoxyphenyl)-n-[(2-phenyl-1h-imidazol-5-yl)methyl]ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2N=C(NC=2)C=2C=CC=CC=2)=C1 AIUQUXSKVQGGPJ-CQSZACIVSA-N 0.000 claims 1
- MHCHTLVMUNWNGH-CQSZACIVSA-N (1r)-1-(3-methoxyphenyl)-n-[(5-phenyl-1h-pyrazol-4-yl)methyl]ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C(=NNC=2)C=2C=CC=CC=2)=C1 MHCHTLVMUNWNGH-CQSZACIVSA-N 0.000 claims 1
- KQAVCSCTVKBYTL-CQSZACIVSA-N (1r)-1-(4-methoxyphenyl)-n-[(5-phenyl-1h-pyrazol-4-yl)methyl]ethanamine Chemical compound C1=CC(OC)=CC=C1[C@@H](C)NCC1=CNN=C1C1=CC=CC=C1 KQAVCSCTVKBYTL-CQSZACIVSA-N 0.000 claims 1
- FDDPNMOEFVXXLX-CYBMUJFWSA-N (1r)-1-naphthalen-1-yl-n-(1h-pyrrol-2-ylmethyl)ethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC1=CC=CN1 FDDPNMOEFVXXLX-CYBMUJFWSA-N 0.000 claims 1
- AVIADSFBMJMFLX-MRXNPFEDSA-N (1r)-1-naphthalen-1-yl-n-[(2-phenyl-1h-imidazol-5-yl)methyl]ethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(N=1)=CNC=1C1=CC=CC=C1 AVIADSFBMJMFLX-MRXNPFEDSA-N 0.000 claims 1
- YRCFBMHWNXENGY-QGZVFWFLSA-N (1r)-1-naphthalen-1-yl-n-[(2-phenylpyrazol-3-yl)methyl]ethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC1=CC=NN1C1=CC=CC=C1 YRCFBMHWNXENGY-QGZVFWFLSA-N 0.000 claims 1
- SBMHZUZLEHWPRH-MRXNPFEDSA-N (1r)-1-naphthalen-1-yl-n-[(5-phenyl-1h-pyrazol-4-yl)methyl]ethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC1=CNN=C1C1=CC=CC=C1 SBMHZUZLEHWPRH-MRXNPFEDSA-N 0.000 claims 1
- ZBHFGFCNHUFPPL-MRXNPFEDSA-N (1r)-1-naphthalen-1-yl-n-[[1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]methyl]ethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(=N1)C=CN1C1=CC=C(C(F)(F)F)C=C1 ZBHFGFCNHUFPPL-MRXNPFEDSA-N 0.000 claims 1
- WPWQNJGUHPWYOF-CQSZACIVSA-N (1r)-1-phenyl-n-[(2-phenyl-1h-imidazol-5-yl)methyl]ethanamine Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(N=1)=CNC=1C1=CC=CC=C1 WPWQNJGUHPWYOF-CQSZACIVSA-N 0.000 claims 1
- KNXPHTZAXFZSJI-CQSZACIVSA-N (1r)-1-phenyl-n-[(5-phenyl-1h-pyrazol-4-yl)methyl]ethanamine Chemical compound N([C@H](C)C=1C=CC=CC=1)CC1=CNN=C1C1=CC=CC=C1 KNXPHTZAXFZSJI-CQSZACIVSA-N 0.000 claims 1
- VRVCXHIFTPXAPT-GICMACPYSA-N (1r)-1-phenyl-n-[1-[1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]ethyl]ethanamine Chemical compound C1([C@@H](C)NC(C)C2=NN(C=C2)C=2C=CC(=CC=2)C(F)(F)F)=CC=CC=C1 VRVCXHIFTPXAPT-GICMACPYSA-N 0.000 claims 1
- NZQNVPUXZXHIPG-LLVKDONJSA-N (1r)-n-(1h-imidazol-2-ylmethyl)-1-(4-methylphenyl)ethanamine Chemical compound N([C@H](C)C=1C=CC(C)=CC=1)CC1=NC=CN1 NZQNVPUXZXHIPG-LLVKDONJSA-N 0.000 claims 1
- HCWXAPQJZFCMMZ-GFCCVEGCSA-N (1r)-n-(1h-imidazol-2-ylmethyl)-1-naphthalen-1-ylethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC1=NC=CN1 HCWXAPQJZFCMMZ-GFCCVEGCSA-N 0.000 claims 1
- UMPGQPQDZNXALJ-GFCCVEGCSA-N (1r)-n-(1h-imidazol-5-ylmethyl)-1-naphthalen-1-ylethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC1=CN=CN1 UMPGQPQDZNXALJ-GFCCVEGCSA-N 0.000 claims 1
- GKATVDYZQAVKBK-CQSZACIVSA-N (1r)-n-[(1-methylpyrrol-2-yl)methyl]-1-naphthalen-1-ylethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC1=CC=CN1C GKATVDYZQAVKBK-CQSZACIVSA-N 0.000 claims 1
- HFBZUKXIIVQTEC-CYBMUJFWSA-N (1r)-n-[(2-ethyl-5-methyl-1h-imidazol-4-yl)methyl]-1-naphthalen-1-ylethanamine Chemical compound N1C(CC)=NC(C)=C1CN[C@H](C)C1=CC=CC2=CC=CC=C12 HFBZUKXIIVQTEC-CYBMUJFWSA-N 0.000 claims 1
- ZTFSWJOUIVRWSC-OAHLLOKOSA-N (1r)-n-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC2=C(N(N=C2C)C=2C=CC=CC=2)C)=C1 ZTFSWJOUIVRWSC-OAHLLOKOSA-N 0.000 claims 1
- GXGHTWHZTRCTQS-MRXNPFEDSA-N (1r)-n-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-1-(4-methylphenyl)ethanamine Chemical compound N([C@H](C)C=1C=CC(C)=CC=1)CC(=C1C)C(C)=NN1C1=CC=CC=C1 GXGHTWHZTRCTQS-MRXNPFEDSA-N 0.000 claims 1
- PHWDXZHMAMHCIN-QGZVFWFLSA-N (1r)-n-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-1-naphthalen-1-ylethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(=C1C)C(C)=NN1C1=CC=CC=C1 PHWDXZHMAMHCIN-QGZVFWFLSA-N 0.000 claims 1
- VFSZQOSWMSNJAP-OAHLLOKOSA-N (1r)-n-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-1-phenylethanamine Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(=C1C)C(C)=NN1C1=CC=CC=C1 VFSZQOSWMSNJAP-OAHLLOKOSA-N 0.000 claims 1
- GFEGHMCAICCPKK-SNVBAGLBSA-N (1r)-n-[(4-chloro-1-methylpyrazol-3-yl)methyl]-1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C(=CN(C)N=2)Cl)=C1 GFEGHMCAICCPKK-SNVBAGLBSA-N 0.000 claims 1
- QSZKPFLRDJQHEH-GFCCVEGCSA-N (1r)-n-[(4-chloro-1-methylpyrazol-3-yl)methyl]-1-naphthalen-1-ylethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC1=NN(C)C=C1Cl QSZKPFLRDJQHEH-GFCCVEGCSA-N 0.000 claims 1
- FAOCMFWHCKLMGQ-CQSZACIVSA-N (1r)-n-[(5-chloro-1-methyl-4-phenylimidazol-2-yl)methyl]-1-phenylethanamine Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(N(C=1Cl)C)=NC=1C1=CC=CC=C1 FAOCMFWHCKLMGQ-CQSZACIVSA-N 0.000 claims 1
- CDQPVTKNACDLFC-KWCCSABGSA-N (1r)-n-[1-[1-(3-chlorophenyl)-5-methoxypyrazol-3-yl]ethyl]-1-(3-fluorophenyl)ethanamine Chemical compound COC1=CC(C(C)N[C@H](C)C=2C=C(F)C=CC=2)=NN1C1=CC=CC(Cl)=C1 CDQPVTKNACDLFC-KWCCSABGSA-N 0.000 claims 1
- ASYNYJBSNOSGQN-GICMACPYSA-N (1r)-n-[1-[1-(3-chlorophenyl)-5-methoxypyrazol-3-yl]ethyl]-1-phenylethanamine Chemical compound COC1=CC(C(C)N[C@H](C)C=2C=CC=CC=2)=NN1C1=CC=CC(Cl)=C1 ASYNYJBSNOSGQN-GICMACPYSA-N 0.000 claims 1
- FJXHQJTYKKPMGO-KWCCSABGSA-N (1r)-n-[1-[1-(4-bromophenyl)-5-methoxypyrazol-3-yl]ethyl]-1-(3-chlorophenyl)ethanamine Chemical compound COC1=CC(C(C)N[C@H](C)C=2C=C(Cl)C=CC=2)=NN1C1=CC=C(Br)C=C1 FJXHQJTYKKPMGO-KWCCSABGSA-N 0.000 claims 1
- DCKITMWASKRPTH-GICMACPYSA-N (1r)-n-[1-[5-methoxy-1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]ethyl]-1-phenylethanamine Chemical compound COC1=CC(C(C)N[C@H](C)C=2C=CC=CC=2)=NN1C1=CC=C(C(F)(F)F)C=C1 DCKITMWASKRPTH-GICMACPYSA-N 0.000 claims 1
- VMZFSZUEKQQIPG-KWCCSABGSA-N (1r)-n-[1-[5-methoxy-1-[6-(trifluoromethyl)pyridin-3-yl]pyrazol-3-yl]ethyl]-1-phenylethanamine Chemical compound COC1=CC(C(C)N[C@H](C)C=2C=CC=CC=2)=NN1C1=CC=C(C(F)(F)F)N=C1 VMZFSZUEKQQIPG-KWCCSABGSA-N 0.000 claims 1
- SOWWEPBYESBCRJ-MRXNPFEDSA-N (1r)-n-[[1-(benzenesulfonyl)pyrrol-2-yl]methyl]-1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2N(C=CC=2)S(=O)(=O)C=2C=CC=CC=2)=C1 SOWWEPBYESBCRJ-MRXNPFEDSA-N 0.000 claims 1
- YVYWTBOTIRBULT-GOSISDBHSA-N (1r)-n-[[1-(benzenesulfonyl)pyrrol-2-yl]methyl]-1-naphthalen-1-ylethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC1=CC=CN1S(=O)(=O)C1=CC=CC=C1 YVYWTBOTIRBULT-GOSISDBHSA-N 0.000 claims 1
- SPLZEMSPEQXAQO-MRXNPFEDSA-N (1r)-n-[[3-(4-tert-butylphenyl)-1,2,4-oxadiazol-5-yl]methyl]-1-(4-methylphenyl)ethanamine Chemical compound N([C@H](C)C=1C=CC(C)=CC=1)CC(ON=1)=NC=1C1=CC=C(C(C)(C)C)C=C1 SPLZEMSPEQXAQO-MRXNPFEDSA-N 0.000 claims 1
- YPXHODADJHCSAW-QGZVFWFLSA-N (1r)-n-[[3-(4-tert-butylphenyl)-1,2,4-oxadiazol-5-yl]methyl]-1-naphthalen-2-ylethanamine Chemical compound N([C@H](C)C=1C=C2C=CC=CC2=CC=1)CC(ON=1)=NC=1C1=CC=C(C(C)(C)C)C=C1 YPXHODADJHCSAW-QGZVFWFLSA-N 0.000 claims 1
- WBUZOQAYVRSQOZ-CQSZACIVSA-N (1r)-n-[[5-methoxy-1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC=2C=C(N(N=2)C=2C=CC(=CC=2)C(F)(F)F)OC)=CC=CC=C1 WBUZOQAYVRSQOZ-CQSZACIVSA-N 0.000 claims 1
- FENCNWQHLRRYDF-TZHYSIJRSA-N 1-(4-fluorophenyl)-4-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]pyrrolidin-2-one Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(CC1=O)CN1C1=CC=C(F)C=C1 FENCNWQHLRRYDF-TZHYSIJRSA-N 0.000 claims 1
- QVYKGSXEOYTESD-UJONTBEJSA-N 2-methyl-n-[(1r)-1-phenylethyl]-1-[1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]propan-1-amine Chemical compound C1([C@@H](C)NC(C(C)C)C2=NN(C=C2)C=2C=CC(=CC=2)C(F)(F)F)=CC=CC=C1 QVYKGSXEOYTESD-UJONTBEJSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- YBVMEDQIBORKAI-GICMACPYSA-N 4-[3-[1-[[(1r)-1-(3-chlorophenyl)ethyl]amino]ethyl]-5-methoxypyrazol-1-yl]benzonitrile Chemical compound COC1=CC(C(C)N[C@H](C)C=2C=C(Cl)C=CC=2)=NN1C1=CC=C(C#N)C=C1 YBVMEDQIBORKAI-GICMACPYSA-N 0.000 claims 1
- QFYWVHWQWVATAH-KWCCSABGSA-N 4-[[[(1r)-1-(3-chlorophenyl)ethyl]amino]methyl]-1-(4-fluorophenyl)pyrrolidin-2-one Chemical compound N([C@H](C)C=1C=C(Cl)C=CC=1)CC(CC1=O)CN1C1=CC=C(F)C=C1 QFYWVHWQWVATAH-KWCCSABGSA-N 0.000 claims 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 1
- 201000002980 Hyperparathyroidism Diseases 0.000 claims 1
- 208000005475 Vascular calcification Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000004094 calcium homeostasis Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
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| EP1937233B1 (en) * | 2005-09-02 | 2013-01-09 | Amgen Inc. | Modulating intestinal fluid balance using calcimimetics |
| WO2010042642A1 (en) * | 2008-10-08 | 2010-04-15 | Amgen Inc. | Calcium receptor modulating agents |
| EP2435400A2 (en) | 2009-05-27 | 2012-04-04 | Leo Pharma A/S | Novel calcium sensing receptor modulating compounds and pharmaceutical use thereof |
| CA2762137A1 (en) | 2009-05-27 | 2010-12-02 | Leo Pharma A/S | Novel calcium sensing receptor modulating compounds and pharmaceutical use thereof |
| WO2012069421A1 (en) | 2010-11-26 | 2012-05-31 | Leo Pharma A/S | Calcium-sensing receptor-active compounds |
| US20130244995A1 (en) | 2010-11-26 | 2013-09-19 | Leo Pharma A/S | Calcium-sensing receptor-active compounds |
| EP2643298A1 (en) | 2010-11-26 | 2013-10-02 | Leo Pharma A/S | Substituted cyclopentyl - azines as casr- active compounds |
| WO2012069419A1 (en) | 2010-11-26 | 2012-05-31 | Leo Pharma A/S | Calcium-sensing receptor-active compounds |
| SMT201900506T1 (it) * | 2012-02-24 | 2019-11-13 | Lupin Ltd | Composti cromanici sostituiti come modulatori dei recettori sensibili al calcio |
| CN102827056B (zh) * | 2012-09-03 | 2014-07-23 | 华东理工大学 | N-芳基取代吡咯烷酮衍生物及其用途 |
| US10449216B2 (en) | 2013-09-13 | 2019-10-22 | Georgia State University Research Foundation, Inc. | Modulating drug effects against metabotropic glutamate receptor with extracellular calcium |
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| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6011068A (en) | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6031003A (en) | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| RU2146132C1 (ru) * | 1993-02-23 | 2000-03-10 | Брихэм энд Уимен З Хоспитал, Инк. | Фармацевтическая композиция, активная в отношении рецептора кальция, способ лечения пациента, способ анализа соединения оказывать влияние на активность рецептора неорганического иона, нуклеиновая кислота, кодирующая рецептор, рецептор кальция |
| WO1997041090A1 (en) * | 1996-05-01 | 1997-11-06 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
| EP1020447A4 (en) * | 1997-09-11 | 2000-11-15 | Nissan Chemical Ind Ltd | PYRAZOLE-BASED COMPOUNDS AND PLANT DISEASE CONTROL AGENT |
| IL144717A0 (en) | 1999-02-24 | 2002-06-30 | Hoffmann La Roche | Phenyl-and pyridinyl derivatives |
| EP1074539B1 (en) | 1999-08-04 | 2007-10-17 | Sumitomo Chemical Company, Limited | Process for producing optically active 3,3,3,-trifluoro-2-hydroxy-2-methylpropionic acid, and salt thereof |
| ES2254077T3 (es) | 1999-12-18 | 2006-06-16 | Wella Aktiengesellschaft | Derivados 2-aminoalquil-1,4-diaminobenceno y su utilizacion para el teñido de fibras. |
| FR2809396B1 (fr) | 2000-05-24 | 2005-10-14 | Centre Nat Rech Scient | Nouvelles molecules possedant une activite calcimimetique et leur mode de preparation |
| JP4045722B2 (ja) | 2000-07-19 | 2008-02-13 | 住友化学株式会社 | アミン化合物、中間体、製造法および光学分割剤 |
| FR2812875B1 (fr) | 2000-08-08 | 2003-12-12 | Centre Nat Rech Scient | Nouvelles diamines possedant une activite modulatrice des casr et leur mode de preparation |
| US6908935B2 (en) | 2002-05-23 | 2005-06-21 | Amgen Inc. | Calcium receptor modulating agents |
| US7176322B2 (en) * | 2002-05-23 | 2007-02-13 | Amgen Inc. | Calcium receptor modulating agents |
| AU2003272767A1 (en) | 2002-09-30 | 2004-04-23 | Schering Corporation | Use of tricyclic amides for the treatment of disorders of calcium homeostasis |
| JP4629036B2 (ja) | 2004-05-28 | 2011-02-09 | 田辺三菱製薬株式会社 | アリールアルキルアミン化合物及びその製法 |
| PL1882684T3 (pl) | 2005-05-19 | 2015-08-31 | Astellas Pharma Inc | Pochodna pirolidyny albo jej sól |
| WO2008035381A2 (en) | 2006-09-22 | 2008-03-27 | Ind-Swift Laboratories Limited | Process for the preparation of amine derivatives as calcimimetics |
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- 2008-10-15 WO PCT/US2008/011755 patent/WO2009051718A2/en not_active Ceased
- 2008-10-15 EP EP08839241.0A patent/EP2212284B1/en active Active
- 2008-10-15 JP JP2010529937A patent/JP5478496B2/ja not_active Expired - Fee Related