CA2486399C - Calcium receptor modulating agents - Google Patents
Calcium receptor modulating agents Download PDFInfo
- Publication number
- CA2486399C CA2486399C CA2486399A CA2486399A CA2486399C CA 2486399 C CA2486399 C CA 2486399C CA 2486399 A CA2486399 A CA 2486399A CA 2486399 A CA2486399 A CA 2486399A CA 2486399 C CA2486399 C CA 2486399C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- methyloxy
- phenyl
- ethanamine
- 6alkyl
- 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.)
- Expired - Fee Related
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- 239000003795 chemical substances by application Substances 0.000 title description 7
- 102000013830 Calcium-Sensing Receptors Human genes 0.000 title description 5
- 108010050543 Calcium-Sensing Receptors Proteins 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 258
- 238000000034 method Methods 0.000 claims abstract description 118
- 239000000203 mixture Substances 0.000 claims abstract description 96
- 150000003839 salts Chemical class 0.000 claims abstract description 50
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 108090000445 Parathyroid hormone Proteins 0.000 claims abstract description 19
- 230000028327 secretion Effects 0.000 claims abstract description 17
- 201000010099 disease Diseases 0.000 claims abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
- 201000002980 Hyperparathyroidism Diseases 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 8
- 208000020084 Bone disease Diseases 0.000 claims abstract description 7
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 268
- -1 -C(=O)OH Chemical group 0.000 claims description 168
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 105
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 99
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 97
- 229910052736 halogen Inorganic materials 0.000 claims description 71
- 150000002367 halogens Chemical class 0.000 claims description 71
- 150000001412 amines Chemical class 0.000 claims description 69
- 125000000623 heterocyclic group Chemical group 0.000 claims description 65
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 64
- 125000001424 substituent group Chemical group 0.000 claims description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 62
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 125000004429 atom Chemical group 0.000 claims description 49
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 48
- 125000001624 naphthyl group Chemical group 0.000 claims description 48
- 229910052760 oxygen Inorganic materials 0.000 claims description 48
- 229910052717 sulfur Inorganic materials 0.000 claims description 48
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 229920006395 saturated elastomer Chemical group 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000001188 haloalkyl group Chemical group 0.000 claims description 27
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- IVLVBSIHYPPSBB-LJQANCHMSA-N (1r)-n-[[3-(6-ethoxypyridin-3-yl)-4-methoxyphenyl]methyl]-1-naphthalen-1-ylethanamine Chemical compound C1=NC(OCC)=CC=C1C1=CC(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C1OC IVLVBSIHYPPSBB-LJQANCHMSA-N 0.000 claims description 4
- DNJNIVCXNVKPGI-GOSISDBHSA-N (1r)-n-[[4-(2-methoxyethoxy)-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=CC(=CC=2)C(F)(F)F)OCCOC)=CC=CC=C1 DNJNIVCXNVKPGI-GOSISDBHSA-N 0.000 claims description 4
- FPTSTHKGNCSJHO-OAHLLOKOSA-N (1r)-n-[[4-chloro-3-[4-(trifluoromethoxy)phenyl]phenyl]methyl]-1-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(Cl)=CC=2)C=2C=CC(OC(F)(F)F)=CC=2)=C1 FPTSTHKGNCSJHO-OAHLLOKOSA-N 0.000 claims description 4
- CFKONZIMXTYJHT-QGZVFWFLSA-N (1r)-n-[[4-chloro-3-[4-(trifluoromethoxy)phenyl]phenyl]methyl]-1-naphthalen-1-ylethanamine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CC(C=1)=CC=C(Cl)C=1C1=CC=C(OC(F)(F)F)C=C1 CFKONZIMXTYJHT-QGZVFWFLSA-N 0.000 claims description 4
- OWONWIQJYVNGBG-GOSISDBHSA-N (1r)-n-[[4-ethoxy-3-(4-methoxyphenyl)phenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=CC(OC)=CC=2)OCC)=CC=CC=C1 OWONWIQJYVNGBG-GOSISDBHSA-N 0.000 claims description 4
- CETUQNBULBNBNJ-MRXNPFEDSA-N (1r)-n-[[4-fluoro-3-(4-methoxyphenyl)phenyl]methyl]-1-(4-methoxyphenyl)ethanamine Chemical compound C1=CC(OC)=CC=C1[C@@H](C)NCC1=CC=C(F)C(C=2C=CC(OC)=CC=2)=C1 CETUQNBULBNBNJ-MRXNPFEDSA-N 0.000 claims description 4
- ZBRFTRYQMDAJBZ-LJQANCHMSA-N (1r)-n-[[4-methoxy-3-(1-methylindazol-5-yl)phenyl]methyl]-1-naphthalen-1-ylethanamine Chemical compound C1=C2N(C)N=CC2=CC(C2=CC(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)=CC=C2OC)=C1 ZBRFTRYQMDAJBZ-LJQANCHMSA-N 0.000 claims description 4
- NEBIMYHJRKARGF-QGZVFWFLSA-N (1r)-n-[[4-methoxy-3-(1-methylindazol-5-yl)phenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=C3C=NN(C)C3=CC=2)OC)=CC=CC=C1 NEBIMYHJRKARGF-QGZVFWFLSA-N 0.000 claims description 4
- XECXXTPSLPEQBL-GOSISDBHSA-N (1r)-n-[[4-methoxy-3-(1-methylindol-6-yl)phenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=C3N(C)C=CC3=CC=2)OC)=CC=CC=C1 XECXXTPSLPEQBL-GOSISDBHSA-N 0.000 claims description 4
- JMKYAESRILIBMO-LJQANCHMSA-N (1r)-n-[[4-methoxy-3-(2-methylindazol-5-yl)phenyl]methyl]-1-naphthalen-1-ylethanamine Chemical compound C1=CC2=NN(C)C=C2C=C1C1=CC(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)=CC=C1OC JMKYAESRILIBMO-LJQANCHMSA-N 0.000 claims description 4
- MHCPDJPPPAXLJD-GOSISDBHSA-N (1r)-n-[[4-methoxy-3-[3-(trifluoromethoxy)phenyl]phenyl]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(OC(F)(F)F)=C1 MHCPDJPPPAXLJD-GOSISDBHSA-N 0.000 claims description 4
- UGWMKLSZBLVUJS-OAHLLOKOSA-N (1r)-n-[[4-methoxy-3-[6-(trifluoromethyl)pyridin-3-yl]phenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=NC(=CC=2)C(F)(F)F)OC)=CC=CC=C1 UGWMKLSZBLVUJS-OAHLLOKOSA-N 0.000 claims description 4
- 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 description 4
- AIKXYHWIVVEIQJ-QGZVFWFLSA-N 5-[2-methoxy-5-[[[(1r)-1-phenylethyl]amino]methyl]phenyl]-n,n-dimethylpyridin-2-amine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=NC(=CC=2)N(C)C)OC)=CC=CC=C1 AIKXYHWIVVEIQJ-QGZVFWFLSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- INKISUITZNDWBK-HXUWFJFHSA-N ethyl 4-[2-methoxy-5-[[[(1r)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C(=CC=C(CN[C@H](C)C=3C4=CC=CC=C4C=CC=3)C=2)OC)=C1 INKISUITZNDWBK-HXUWFJFHSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- YAOTUHPBMUVMDI-OAHLLOKOSA-N (1r)-1-(3-methoxyphenyl)-n-[[4-methoxy-3-[2-(2,2,2-trifluoroethoxy)pyrimidin-5-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)=NC=2)=C1 YAOTUHPBMUVMDI-OAHLLOKOSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
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- 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 description 3
- 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 description 3
- IIBDGGYPQWHSBE-GOSISDBHSA-N (1r)-n-[[3-(4-chlorophenyl)-4-methoxyphenyl]methyl]-1-naphthalen-1-ylethanamine Chemical compound COC1=CC=C(CN[C@H](C)C=2C3=CC=CC=C3C=CC=2)C=C1C1=CC=C(Cl)C=C1 IIBDGGYPQWHSBE-GOSISDBHSA-N 0.000 claims description 3
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- QJXDHSSSGPGEQC-UHFFFAOYSA-N 1-(3-bromophenyl)-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(Br)=C1 QJXDHSSSGPGEQC-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- YRPYIMZSUOZJTN-GOSISDBHSA-N 4-[2-methoxy-5-[[[(1r)-1-(3-methoxyphenyl)ethyl]amino]methyl]phenyl]-n,n-dimethylbenzamide Chemical compound COC1=CC=CC([C@@H](C)NCC=2C=C(C(OC)=CC=2)C=2C=CC(=CC=2)C(=O)N(C)C)=C1 YRPYIMZSUOZJTN-GOSISDBHSA-N 0.000 claims description 3
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- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/18—Drugs for disorders of the endocrine system of the parathyroid hormones
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/18—Drugs for disorders of the endocrine system of the parathyroid hormones
- A61P5/20—Drugs for disorders of the endocrine system of the parathyroid hormones for decreasing, blocking or antagonising the activity of PTH
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
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| RU2599788C2 (ru) | 2010-06-30 | 2016-10-20 | Лео Фарма А/С | Новая полиморфная форма кальцимиметического соединения |
| EP2643292A1 (en) | 2010-11-26 | 2013-10-02 | Leo Pharma A/S | Calcium-sensing receptor-active compounds |
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2003
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- 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
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- 2003-05-23 JP JP2004507434A patent/JP4486882B2/ja not_active Expired - Fee Related
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- 2003-05-23 EP EP03729111A patent/EP1509497A1/en not_active Withdrawn
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2005
- 2005-02-18 US US11/061,084 patent/US7196102B2/en not_active Expired - Fee Related
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2007
- 2007-01-30 US US11/700,336 patent/US7524873B2/en not_active Expired - Fee Related
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2010
- 2010-02-10 JP JP2010027494A patent/JP2010150268A/ja active Pending
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| US7196102B2 (en) | 2007-03-27 |
| AU2003233671A1 (en) | 2003-12-12 |
| AU2003233671B2 (en) | 2007-08-16 |
| JP2005527625A (ja) | 2005-09-15 |
| WO2003099776A1 (en) | 2003-12-04 |
| CA2486399A1 (en) | 2003-12-04 |
| US6908935B2 (en) | 2005-06-21 |
| AU2003233671B8 (en) | 2003-12-12 |
| US20050143426A1 (en) | 2005-06-30 |
| US7524873B2 (en) | 2009-04-28 |
| MXPA04011471A (es) | 2005-02-14 |
| JP2010150268A (ja) | 2010-07-08 |
| JP4486882B2 (ja) | 2010-06-23 |
| US20070142381A1 (en) | 2007-06-21 |
| EP1509497A1 (en) | 2005-03-02 |
| PL376438A1 (en) | 2005-12-27 |
| US20040082625A1 (en) | 2004-04-29 |
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