JP2005527625A5 - - Google Patents
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- Publication number
- JP2005527625A5 JP2005527625A5 JP2004507434A JP2004507434A JP2005527625A5 JP 2005527625 A5 JP2005527625 A5 JP 2005527625A5 JP 2004507434 A JP2004507434 A JP 2004507434A JP 2004507434 A JP2004507434 A JP 2004507434A JP 2005527625 A5 JP2005527625 A5 JP 2005527625A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- phenyl
- methyl
- methyloxy
- alkyl
- 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 85
- 150000001875 compounds Chemical class 0.000 claims 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 48
- 125000005843 halogen group Chemical group 0.000 claims 40
- 125000001188 haloalkyl group Chemical group 0.000 claims 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims 36
- 150000003839 salts Chemical class 0.000 claims 32
- 125000001424 substituent group Chemical group 0.000 claims 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 28
- 125000004429 atom Chemical group 0.000 claims 27
- 125000000623 heterocyclic group Chemical group 0.000 claims 26
- 229910052760 oxygen Inorganic materials 0.000 claims 26
- 125000004430 oxygen atom Chemical group O* 0.000 claims 25
- 125000004434 sulfur atom Chemical group 0.000 claims 25
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 22
- 125000001624 naphthyl group Chemical group 0.000 claims 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 229920006395 saturated elastomer Polymers 0.000 claims 11
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 9
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 9
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- -1 2,4-dimethylphenyl group Chemical group 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 201000002980 Hyperparathyroidism Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- GSOMMFLMCBOYKC-OAHLLOKOSA-N (1r)-1-(3-chlorophenyl)-n-[[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]ethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=CC(=CC=2)C(F)(F)F)OC)=CC=CC(Cl)=C1 GSOMMFLMCBOYKC-OAHLLOKOSA-N 0.000 claims 1
- XLHSNWIFKVHFLT-OAHLLOKOSA-N (1r)-1-(3-fluorophenyl)-n-[[3-(4-fluorophenyl)-4-methoxyphenyl]methyl]ethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=CC(F)=CC=2)OC)=CC=CC(F)=C1 XLHSNWIFKVHFLT-OAHLLOKOSA-N 0.000 claims 1
- VWINXACDKLTYJX-OAHLLOKOSA-N (1r)-1-(3-fluorophenyl)-n-[[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]ethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=CC(=CC=2)C(F)(F)F)OC)=CC=CC(F)=C1 VWINXACDKLTYJX-OAHLLOKOSA-N 0.000 claims 1
- CEPPLCAAVYJNIS-MRXNPFEDSA-N (1r)-1-(3-methoxyphenyl)-n-[(4-methoxy-3-pyridin-3-ylphenyl)methyl]ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2C=NC=CC=2)=C1 CEPPLCAAVYJNIS-MRXNPFEDSA-N 0.000 claims 1
- RQADPXJMIZWVPT-GOSISDBHSA-N (1r)-1-(3-methoxyphenyl)-n-[(4-methoxy-3-quinolin-6-ylphenyl)methyl]ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2C=C3C=CC=NC3=CC=2)=C1 RQADPXJMIZWVPT-GOSISDBHSA-N 0.000 claims 1
- BSFGFDBHPRSHLE-OAHLLOKOSA-N (1r)-1-(3-methoxyphenyl)-n-[(4-methoxy-3-thiophen-2-ylphenyl)methyl]ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2SC=CC=2)=C1 BSFGFDBHPRSHLE-OAHLLOKOSA-N 0.000 claims 1
- XSZFLTHQEHLQFO-OAHLLOKOSA-N (1r)-1-(3-methoxyphenyl)-n-[[4-(trifluoromethyl)-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(=CC=2)C(F)(F)F)C=2C=CC(=CC=2)C(F)(F)F)=C1 XSZFLTHQEHLQFO-OAHLLOKOSA-N 0.000 claims 1
- QIJDSWCRIIVSBQ-MRXNPFEDSA-N (1r)-1-(3-methoxyphenyl)-n-[[4-methoxy-3-[3-(trifluoromethoxy)phenyl]phenyl]methyl]ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2C=C(OC(F)(F)F)C=CC=2)=C1 QIJDSWCRIIVSBQ-MRXNPFEDSA-N 0.000 claims 1
- WAHHHNYICCZJFL-MRXNPFEDSA-N (1r)-1-(3-methoxyphenyl)-n-[[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 WAHHHNYICCZJFL-MRXNPFEDSA-N 0.000 claims 1
- LLXSNCFTBASYEL-MRXNPFEDSA-N (1r)-1-(3-methoxyphenyl)-n-[[4-methoxy-3-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]phenyl]methyl]ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2C=NC(OCC(F)(F)F)=CC=2)=C1 LLXSNCFTBASYEL-MRXNPFEDSA-N 0.000 claims 1
- LCFIMLWBRYBGEW-OAHLLOKOSA-N (1r)-1-(3-methoxyphenyl)-n-[[4-methoxy-3-[6-(trifluoromethyl)pyridin-3-yl]phenyl]methyl]ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2C=NC(=CC=2)C(F)(F)F)=C1 LCFIMLWBRYBGEW-OAHLLOKOSA-N 0.000 claims 1
- RTAQFBDJXHNNOO-QGZVFWFLSA-N (1r)-1-naphthalen-1-yl-n-[[3-[6-(trifluoromethyl)pyridin-3-yl]phenyl]methyl]ethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(C=1)=CC=CC=1C1=CC=C(C(F)(F)F)N=C1 RTAQFBDJXHNNOO-QGZVFWFLSA-N 0.000 claims 1
- MLOYLNMJZHVRSN-OAHLLOKOSA-N (1r)-n-[(4-chloro-3-pyridin-3-ylphenyl)methyl]-1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(Cl)=CC=2)C=2C=NC=CC=2)=C1 MLOYLNMJZHVRSN-OAHLLOKOSA-N 0.000 claims 1
- VUOVDNBYCMNUQV-LJQANCHMSA-N (1r)-n-[(4-methoxy-3-naphthalen-2-ylphenyl)methyl]-1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2C=C3C=CC=CC3=CC=2)=C1 VUOVDNBYCMNUQV-LJQANCHMSA-N 0.000 claims 1
- XTJHZNKRDGKTAT-OAQYLSRUSA-N (1r)-n-[(4-methoxy-3-naphthalen-2-ylphenyl)methyl]-1-naphthalen-1-ylethanamine Chemical compound C1=CC=CC2=CC(C3=CC(CN[C@H](C)C=4C5=CC=CC=C5C=CC=4)=CC=C3OC)=CC=C21 XTJHZNKRDGKTAT-OAQYLSRUSA-N 0.000 claims 1
- LEQFNLGTEITPTE-LJQANCHMSA-N (1r)-n-[(4-methoxy-3-naphthalen-2-ylphenyl)methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=C3C=CC=CC3=CC=2)OC)=CC=CC=C1 LEQFNLGTEITPTE-LJQANCHMSA-N 0.000 claims 1
- OTEFLXQBXZRJIK-GOSISDBHSA-N (1r)-n-[(4-methoxy-3-phenylphenyl)methyl]-1-(4-methylphenyl)ethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=CC=CC=2)OC)=CC=C(C)C=C1 OTEFLXQBXZRJIK-GOSISDBHSA-N 0.000 claims 1
- DSCAEVVCTKZVDK-QGZVFWFLSA-N (1r)-n-[(4-methoxy-3-pyrazin-2-ylphenyl)methyl]-1-naphthalen-1-ylethanamine Chemical compound COC1=CC=C(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C=C1C1=CN=CC=N1 DSCAEVVCTKZVDK-QGZVFWFLSA-N 0.000 claims 1
- ALFLSQSRGRWMMK-GOSISDBHSA-N (1r)-n-[(4-methoxy-3-pyridin-2-ylphenyl)methyl]-1-naphthalen-1-ylethanamine Chemical compound COC1=CC=C(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C=C1C1=CC=CC=N1 ALFLSQSRGRWMMK-GOSISDBHSA-N 0.000 claims 1
- BAVLQVRFDZOBIH-GOSISDBHSA-N (1r)-n-[(4-methoxy-3-pyridin-3-ylphenyl)methyl]-1-naphthalen-1-ylethanamine Chemical compound COC1=CC=C(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C=C1C1=CC=CN=C1 BAVLQVRFDZOBIH-GOSISDBHSA-N 0.000 claims 1
- XEWKUHVPJNSANG-GOSISDBHSA-N (1r)-n-[(4-methoxy-3-pyrrol-1-ylphenyl)methyl]-1-naphthalen-1-ylethanamine Chemical compound COC1=CC=C(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C=C1N1C=CC=C1 XEWKUHVPJNSANG-GOSISDBHSA-N 0.000 claims 1
- FOYXABQEUUUOCT-MRXNPFEDSA-N (1r)-n-[(4-methoxy-3-pyrrol-1-ylphenyl)methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)N2C=CC=C2)OC)=CC=CC=C1 FOYXABQEUUUOCT-MRXNPFEDSA-N 0.000 claims 1
- CYMWPTPYYAVYRB-MRXNPFEDSA-N (1r)-n-[(4-methoxy-3-pyrrolidin-1-ylphenyl)methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)N2CCCC2)OC)=CC=CC=C1 CYMWPTPYYAVYRB-MRXNPFEDSA-N 0.000 claims 1
- OVVWUZGGYFWTPZ-HXUWFJFHSA-N (1r)-n-[(4-methoxy-3-quinolin-6-ylphenyl)methyl]-1-naphthalen-1-ylethanamine Chemical compound N1=CC=CC2=CC(C3=CC(CN[C@H](C)C=4C5=CC=CC=C5C=CC=4)=CC=C3OC)=CC=C21 OVVWUZGGYFWTPZ-HXUWFJFHSA-N 0.000 claims 1
- MJIOXYXMGSOJKY-GOSISDBHSA-N (1r)-n-[(4-methoxy-3-quinolin-6-ylphenyl)methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=C3C=CC=NC3=CC=2)OC)=CC=CC=C1 MJIOXYXMGSOJKY-GOSISDBHSA-N 0.000 claims 1
- DIZNYPAVOLTXLB-LJQANCHMSA-N (1r)-n-[(4-methoxy-3-quinoxalin-6-ylphenyl)methyl]-1-naphthalen-1-ylethanamine Chemical compound N1=CC=NC2=CC(C3=CC(CN[C@H](C)C=4C5=CC=CC=C5C=CC=4)=CC=C3OC)=CC=C21 DIZNYPAVOLTXLB-LJQANCHMSA-N 0.000 claims 1
- XAJBBIXNWPPZIL-QGZVFWFLSA-N (1r)-n-[(4-methoxy-3-quinoxalin-6-ylphenyl)methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=C3N=CC=NC3=CC=2)OC)=CC=CC=C1 XAJBBIXNWPPZIL-QGZVFWFLSA-N 0.000 claims 1
- CNHQLJUQQJEHLV-QGZVFWFLSA-N (1r)-n-[(4-methoxy-3-thiophen-2-ylphenyl)methyl]-1-naphthalen-1-ylethanamine Chemical compound COC1=CC=C(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C=C1C1=CC=CS1 CNHQLJUQQJEHLV-QGZVFWFLSA-N 0.000 claims 1
- ZWSUNHQVYZFJSB-OAHLLOKOSA-N (1r)-n-[(4-methoxy-3-thiophen-2-ylphenyl)methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2SC=CC=2)OC)=CC=CC=C1 ZWSUNHQVYZFJSB-OAHLLOKOSA-N 0.000 claims 1
- KDIVLDLVXSFWGT-MRXNPFEDSA-N (1r)-n-[[3-(1,3-benzothiazol-2-yl)-4-methoxyphenyl]methyl]-1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2SC3=CC=CC=C3N=2)=C1 KDIVLDLVXSFWGT-MRXNPFEDSA-N 0.000 claims 1
- MLJLWOLFBPENHB-MRXNPFEDSA-N (1r)-n-[[3-(1,3-benzothiazol-2-yl)-4-methoxyphenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2SC3=CC=CC=C3N=2)OC)=CC=CC=C1 MLJLWOLFBPENHB-MRXNPFEDSA-N 0.000 claims 1
- UAHSVSJVRITSCG-GOSISDBHSA-N (1r)-n-[[3-(1,3-benzoxazol-5-yl)-4-methoxyphenyl]methyl]-1-naphthalen-1-ylethanamine Chemical compound C1=C2OC=NC2=CC(C2=CC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)=CC=C2OC)=C1 UAHSVSJVRITSCG-GOSISDBHSA-N 0.000 claims 1
- OQOVGTNMORGUEU-QGZVFWFLSA-N (1r)-n-[[3-(1-benzothiophen-3-yl)-4-methoxyphenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C3=CC=CC=C3SC=2)OC)=CC=CC=C1 OQOVGTNMORGUEU-QGZVFWFLSA-N 0.000 claims 1
- LKTFBEPQGHDSFD-OAHLLOKOSA-N (1r)-n-[[3-(2,1,3-benzothiadiazol-5-yl)-4-methoxyphenyl]methyl]-1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C2=CC3=NSN=C3C=C2)=C1 LKTFBEPQGHDSFD-OAHLLOKOSA-N 0.000 claims 1
- ASOUJWKMTRGINA-OAHLLOKOSA-N (1r)-n-[[3-(2,1,3-benzothiadiazol-5-yl)-4-methoxyphenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C2=CC3=NSN=C3C=C2)OC)=CC=CC=C1 ASOUJWKMTRGINA-OAHLLOKOSA-N 0.000 claims 1
- APXNHCQYZZUWBZ-OAHLLOKOSA-N (1r)-n-[[3-(2,1,3-benzoxadiazol-5-yl)-4-methoxyphenyl]methyl]-1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C2=CC3=NON=C3C=C2)=C1 APXNHCQYZZUWBZ-OAHLLOKOSA-N 0.000 claims 1
- AOQMKDMVAHVRMW-QGZVFWFLSA-N (1r)-n-[[3-(2,1,3-benzoxadiazol-5-yl)-4-methoxyphenyl]methyl]-1-naphthalen-1-ylethanamine Chemical compound C1=CC2=NON=C2C=C1C1=CC(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C1OC AOQMKDMVAHVRMW-QGZVFWFLSA-N 0.000 claims 1
- RXIHFECCUGCJJK-OAHLLOKOSA-N (1r)-n-[[3-(2,1,3-benzoxadiazol-5-yl)-4-methoxyphenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C2=CC3=NON=C3C=C2)OC)=CC=CC=C1 RXIHFECCUGCJJK-OAHLLOKOSA-N 0.000 claims 1
- UMYUUBDMQLDDTH-OAHLLOKOSA-N (1r)-n-[[3-(2,2-difluoro-1,3-benzodioxol-5-yl)-4-methoxyphenyl]methyl]-1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2C=C3OC(F)(F)OC3=CC=2)=C1 UMYUUBDMQLDDTH-OAHLLOKOSA-N 0.000 claims 1
- AXGRUOYVIIUWLD-QGZVFWFLSA-N (1r)-n-[[3-(2,2-difluoro-1,3-benzodioxol-5-yl)-4-methoxyphenyl]methyl]-1-naphthalen-1-ylethanamine Chemical compound C1=C2OC(F)(F)OC2=CC(C2=CC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)=CC=C2OC)=C1 AXGRUOYVIIUWLD-QGZVFWFLSA-N 0.000 claims 1
- HVLRTSLDGIJEKQ-OAHLLOKOSA-N (1r)-n-[[3-(2,2-difluoro-1,3-benzodioxol-5-yl)-4-methoxyphenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=C3OC(F)(F)OC3=CC=2)OC)=CC=CC=C1 HVLRTSLDGIJEKQ-OAHLLOKOSA-N 0.000 claims 1
- ITCGXXYGFCHYIR-QGZVFWFLSA-N (1r)-n-[[3-(2,3-dihydro-1-benzofuran-5-yl)-4-methoxyphenyl]methyl]-1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2C=C3CCOC3=CC=2)=C1 ITCGXXYGFCHYIR-QGZVFWFLSA-N 0.000 claims 1
- NIJPOMBROVGNOL-LJQANCHMSA-N (1r)-n-[[3-(2,3-dihydro-1-benzofuran-5-yl)-4-methoxyphenyl]methyl]-1-naphthalen-1-ylethanamine Chemical compound C1=C2OCCC2=CC(C2=CC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)=CC=C2OC)=C1 NIJPOMBROVGNOL-LJQANCHMSA-N 0.000 claims 1
- MEHPPZLMBARNEC-QGZVFWFLSA-N (1r)-n-[[3-(2,3-dihydro-1-benzofuran-5-yl)-4-methoxyphenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=C3CCOC3=CC=2)OC)=CC=CC=C1 MEHPPZLMBARNEC-QGZVFWFLSA-N 0.000 claims 1
- ZHBHMTSYFTZGJU-QGZVFWFLSA-N (1r)-n-[[3-(2-ethylbenzotriazol-5-yl)-4-methoxyphenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC=2C=C(C(=CC=2)OC)C=2C=CC3=NN(N=C3C=2)CC)=CC=CC=C1 ZHBHMTSYFTZGJU-QGZVFWFLSA-N 0.000 claims 1
- ZLEILCZRYNIVKH-QGZVFWFLSA-N (1r)-n-[[3-(2-fluorophenyl)phenyl]methyl]-1-(4-methylphenyl)ethanamine Chemical compound N([C@H](C)C=1C=CC(C)=CC=1)CC(C=1)=CC=CC=1C1=CC=CC=C1F ZLEILCZRYNIVKH-QGZVFWFLSA-N 0.000 claims 1
- GIWRDDJDHCHBFX-OAHLLOKOSA-N (1r)-n-[[3-(2-fluoropyridin-3-yl)-4-methoxyphenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C(=NC=CC=2)F)OC)=CC=CC=C1 GIWRDDJDHCHBFX-OAHLLOKOSA-N 0.000 claims 1
- KBLCBTOCUIGXOK-MRXNPFEDSA-N (1r)-n-[[3-(4-chlorophenyl)-4-methoxyphenyl]methyl]-1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2C=CC(Cl)=CC=2)=C1 KBLCBTOCUIGXOK-MRXNPFEDSA-N 0.000 claims 1
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- RXXMPHSVIZFZFZ-MRXNPFEDSA-N (1r)-n-[[3-(4-chlorophenyl)-4-methoxyphenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=CC(Cl)=CC=2)OC)=CC=CC=C1 RXXMPHSVIZFZFZ-MRXNPFEDSA-N 0.000 claims 1
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- SNTFBFJNEYIDNA-UHFFFAOYSA-N 1-(3,5-difluorophenyl)-n-[[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]ethanamine Chemical compound C1=C(C=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CNC(C)C1=CC(F)=CC(F)=C1 SNTFBFJNEYIDNA-UHFFFAOYSA-N 0.000 claims 1
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- VWINXACDKLTYJX-UHFFFAOYSA-N 1-(3-fluorophenyl)-n-[[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]ethanamine Chemical compound C1=C(C=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CNC(C)C1=CC=CC(F)=C1 VWINXACDKLTYJX-UHFFFAOYSA-N 0.000 claims 1
- CJWGCBRQAHCVHW-UHFFFAOYSA-N 1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC(C(C)N)=C1 CJWGCBRQAHCVHW-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- LLFDODCZVIRMQP-GOSISDBHSA-N 3-[2-methoxy-5-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]benzamide Chemical compound COC1=CC=C(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C=C1C1=CC=CC(C(N)=O)=C1 LLFDODCZVIRMQP-GOSISDBHSA-N 0.000 claims 1
- ZWTAIWLCPPSPMZ-LJQANCHMSA-N 3-[2-methoxy-5-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]benzonitrile Chemical compound COC1=CC=C(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C=C1C1=CC=CC(C#N)=C1 ZWTAIWLCPPSPMZ-LJQANCHMSA-N 0.000 claims 1
- KGAFHQDYISCNRP-QGZVFWFLSA-N 3-[2-methoxy-5-[[[(1r)-1-phenylethyl]amino]methyl]phenyl]benzonitrile Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=C(C=CC=2)C#N)OC)=CC=CC=C1 KGAFHQDYISCNRP-QGZVFWFLSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- KVVPUSAEZVYAAJ-HXUWFJFHSA-N 4-[2-methoxy-5-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]-n,n-dimethylbenzamide Chemical compound COC1=CC=C(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C=C1C1=CC=C(C(=O)N(C)C)C=C1 KVVPUSAEZVYAAJ-HXUWFJFHSA-N 0.000 claims 1
- MRETXOIWVVGKIL-CYBMUJFWSA-N 4-[2-methoxy-5-[[[(1r)-1-phenylethyl]amino]methyl]phenyl]-1,3-thiazol-2-amine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2N=C(N)SC=2)OC)=CC=CC=C1 MRETXOIWVVGKIL-CYBMUJFWSA-N 0.000 claims 1
- PPXQVKBDPQGWHY-GOSISDBHSA-N 4-[2-methoxy-5-[[[(1r)-1-phenylethyl]amino]methyl]phenyl]-n,n-dimethylbenzamide Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=CC(=CC=2)C(=O)N(C)C)OC)=CC=CC=C1 PPXQVKBDPQGWHY-GOSISDBHSA-N 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- QSJHRIXZZSOGNS-GOSISDBHSA-N C[C@H](C1=CC=CC2=CC=CC=C12)NCC(C=C1)=CC(C(CC2)=CCN2C(O)=O)=C1OC Chemical compound C[C@H](C1=CC=CC2=CC=CC=C12)NCC(C=C1)=CC(C(CC2)=CCN2C(O)=O)=C1OC QSJHRIXZZSOGNS-GOSISDBHSA-N 0.000 claims 1
- FQNGSKRLVSEUAE-OAHLLOKOSA-N C[C@H](C1=CC=CC=C1)NCC(C=C1)=CC(C2=CC=CN=C2N)=C1OC Chemical compound C[C@H](C1=CC=CC=C1)NCC(C=C1)=CC(C2=CC=CN=C2N)=C1OC FQNGSKRLVSEUAE-OAHLLOKOSA-N 0.000 claims 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- WJWBKGUSFBLECB-HXUWFJFHSA-N ethyl 4-[2-methoxy-5-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=CC(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C1OC WJWBKGUSFBLECB-HXUWFJFHSA-N 0.000 claims 1
- FWBKPMQCXOSKNU-GOSISDBHSA-N ethyl 4-[2-methoxy-5-[[[(1r)-1-phenylethyl]amino]methyl]phenyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=CC(CN[C@H](C)C=2C=CC=CC=2)=CC=C1OC FWBKPMQCXOSKNU-GOSISDBHSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- DPVDYMFQKDPRNX-UHFFFAOYSA-N n-[[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-1-(3-methylphenyl)ethanamine Chemical compound C1=C(C=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CNC(C)C1=CC=CC(C)=C1 DPVDYMFQKDPRNX-UHFFFAOYSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 0 C*(C)(C(*)*)C(*)(*)c1cccc(*)c1 Chemical compound C*(C)(C(*)*)C(*)(*)c1cccc(*)c1 0.000 description 5
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| KR101020350B1 (ko) * | 2003-03-13 | 2011-03-08 | 이데미쓰 고산 가부시키가이샤 | 신규한 질소 함유 헤테로환 유도체 및 이를 이용한 유기 전기발광 소자 |
| WO2005065050A2 (ja) * | 2003-12-25 | 2005-07-21 | Asahi Kasei Pharma Corporation | ２環化合物 |
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| KR101182690B1 (ko) * | 2004-03-02 | 2012-09-14 | 아벤티스 파마슈티칼스 인크. | 트립타제 억제제의 제조방법 |
| PT1757582E (pt) | 2004-05-28 | 2016-03-04 | Mitsubishi Tanabe Pharma Corp | Arilalquilaminas e processo para a sua produção |
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| WO2009051718A2 (en) * | 2007-10-15 | 2009-04-23 | Amgen Inc. | Calcium receptor modulating agents |
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| US9056814B2 (en) | 2010-06-30 | 2015-06-16 | Leo Pharma A/S | Polymorphic form of a calcimimetic compound |
| RU2599788C2 (ru) | 2010-06-30 | 2016-10-20 | Лео Фарма А/С | Новая полиморфная форма кальцимиметического соединения |
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-
2003
- 2003-05-22 US US10/444,946 patent/US6908935B2/en not_active Expired - Lifetime
- 2003-05-23 PL PL03376438A patent/PL376438A1/xx unknown
- 2003-05-23 AU AU2003233671A patent/AU2003233671B2/en not_active Ceased
- 2003-05-23 MX MXPA04011471A patent/MXPA04011471A/es active IP Right Grant
- 2003-05-23 CA CA2486399A patent/CA2486399C/en not_active Expired - Fee Related
- 2003-05-23 JP JP2004507434A patent/JP4486882B2/ja not_active Expired - Fee Related
- 2003-05-23 WO PCT/US2003/016401 patent/WO2003099776A1/en not_active Ceased
- 2003-05-23 EP EP03729111A patent/EP1509497A1/en not_active Withdrawn
-
2005
- 2005-02-18 US US11/061,084 patent/US7196102B2/en not_active Expired - Fee Related
-
2007
- 2007-01-30 US US11/700,336 patent/US7524873B2/en not_active Expired - Fee Related
-
2010
- 2010-02-10 JP JP2010027494A patent/JP2010150268A/ja active Pending
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