CA2701792A1 - Calcium receptor modulating agents - Google Patents
Calcium receptor modulating agents Download PDFInfo
- Publication number
- CA2701792A1 CA2701792A1 CA2701792A CA2701792A CA2701792A1 CA 2701792 A1 CA2701792 A1 CA 2701792A1 CA 2701792 A CA2701792 A CA 2701792A CA 2701792 A CA2701792 A CA 2701792A CA 2701792 A1 CA2701792 A1 CA 2701792A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- ethanamine
- phenyl
- pyrazol
- chlorophenyl
- 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.)
- Abandoned
Links
- 102000013830 Calcium-Sensing Receptors Human genes 0.000 title abstract description 36
- 108010050543 Calcium-Sensing Receptors Proteins 0.000 title abstract description 36
- 239000003795 chemical substances by application Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 149
- 238000000034 method Methods 0.000 claims abstract description 78
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 77
- 201000010099 disease Diseases 0.000 claims abstract description 49
- 208000035475 disorder Diseases 0.000 claims abstract description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 110
- -1 cyano, amino Chemical group 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 210000000557 podocyte Anatomy 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 19
- 230000002159 abnormal effect Effects 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 208000005475 Vascular calcification Diseases 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 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 description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
- 201000002980 Hyperparathyroidism Diseases 0.000 claims description 5
- 230000004094 calcium homeostasis Effects 0.000 claims description 5
- 208000015380 nutritional deficiency disease Diseases 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 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 description 4
- 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 description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 230000008991 intestinal motility Effects 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 208000002720 Malnutrition Diseases 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 230000001071 malnutrition Effects 0.000 claims description 3
- 235000000824 malnutrition Nutrition 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 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 2
- 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
- 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
- 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
- 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 2
- 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 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 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
- 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-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
- 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
- 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
- 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
- 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
- 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
- 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
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Classifications
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
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- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US99893307P | 2007-10-15 | 2007-10-15 | |
| US60/998,933 | 2007-10-15 | ||
| PCT/US2008/011755 WO2009051718A2 (en) | 2007-10-15 | 2008-10-15 | Calcium receptor modulating agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2701792A1 true CA2701792A1 (en) | 2009-04-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2701792A Abandoned CA2701792A1 (en) | 2007-10-15 | 2008-10-15 | Calcium receptor modulating agents |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8334317B2 (enExample) |
| EP (1) | EP2212284B1 (enExample) |
| JP (1) | JP5478496B2 (enExample) |
| AU (1) | AU2008311974B2 (enExample) |
| CA (1) | CA2701792A1 (enExample) |
| ES (1) | ES2476391T3 (enExample) |
| WO (1) | WO2009051718A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
- 2008-10-15 AU AU2008311974A patent/AU2008311974B2/en not_active Ceased
- 2008-10-15 US US12/738,279 patent/US8334317B2/en active Active
- 2008-10-15 CA CA2701792A patent/CA2701792A1/en not_active Abandoned
- 2008-10-15 ES ES08839241.0T patent/ES2476391T3/es active Active
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009051718A2 (en) | 2009-04-23 |
| US20110178133A1 (en) | 2011-07-21 |
| EP2212284B1 (en) | 2014-04-30 |
| AU2008311974B2 (en) | 2013-11-21 |
| ES2476391T3 (es) | 2014-07-14 |
| US8334317B2 (en) | 2012-12-18 |
| WO2009051718A3 (en) | 2009-06-11 |
| EP2212284A2 (en) | 2010-08-04 |
| JP2011500679A (ja) | 2011-01-06 |
| AU2008311974A1 (en) | 2009-04-23 |
| JP5478496B2 (ja) | 2014-04-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20131001 |
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| FZDE | Discontinued |
Effective date: 20151015 |