BG106942A - Калцилитични съединения - Google Patents
Калцилитични съединения Download PDFInfo
- Publication number
- BG106942A BG106942A BG106942A BG10694202A BG106942A BG 106942 A BG106942 A BG 106942A BG 106942 A BG106942 A BG 106942A BG 10694202 A BG10694202 A BG 10694202A BG 106942 A BG106942 A BG 106942A
- Authority
- BG
- Bulgaria
- Prior art keywords
- hydroxy
- phenyl
- propoxy
- cyano
- indan
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 152
- 230000001126 calcilytic effect Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 32
- -1 3- {4-Cyano-3 - [(S) -2-hydroxy-3- (2-indan-yl-1,1-dimethyl-ethylamino) propoxy] -phenyl} -propionic acid Chemical compound 0.000 claims description 82
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 235000019260 propionic acid Nutrition 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 210000002966 serum Anatomy 0.000 claims description 13
- 210000000988 bone and bone Anatomy 0.000 claims description 12
- 125000004494 ethyl ester group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 102000013830 Calcium-Sensing Receptors Human genes 0.000 claims description 11
- 108010050543 Calcium-Sensing Receptors Proteins 0.000 claims description 11
- 230000002159 abnormal effect Effects 0.000 claims description 11
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 10
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 208000010392 Bone Fractures Diseases 0.000 claims description 6
- 206010017076 Fracture Diseases 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- PYDOOGXGXVMZSG-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-amine Chemical compound C1=CC=C2CC(CC(C)(N)C)CC2=C1 PYDOOGXGXVMZSG-UHFFFAOYSA-N 0.000 claims description 5
- NJBFJCJKWWIKRD-HSZRJFAPSA-N 3-[4-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoic acid Chemical compound C([C@H](O)CNC(C)(CC1CC2=CC=CC=C2C1)C)OC1=CC(CCC(O)=O)=CC=C1C#N NJBFJCJKWWIKRD-HSZRJFAPSA-N 0.000 claims description 5
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- FICQFRCPSFCFBY-UHFFFAOYSA-N 2-[bis(methylsulfanyl)methylidene]propanedinitrile Chemical compound CSC(SC)=C(C#N)C#N FICQFRCPSFCFBY-UHFFFAOYSA-N 0.000 claims description 4
- QTTZOKJQOMEHAT-XMMPIXPASA-N 3-[3-cyano-4-[(2r)-2-hydroxy-3-[[2-methyl-1-(5,6,7,8-tetrahydronaphthalen-2-yl)propan-2-yl]amino]propoxy]phenyl]propanoic acid Chemical compound C([C@H](O)CNC(C)(CC=1C=C2CCCCC2=CC=1)C)OC1=CC=C(CCC(O)=O)C=C1C#N QTTZOKJQOMEHAT-XMMPIXPASA-N 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 230000000123 anti-resoprtive effect Effects 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- DMWBVRRUBDZTBK-RUZDIDTESA-N ethyl 3-[4-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoate Chemical compound CCOC(=O)CCC1=CC=C(C#N)C(OC[C@H](O)CNC(C)(C)CC2CC3=CC=CC=C3C2)=C1 DMWBVRRUBDZTBK-RUZDIDTESA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000004079 mineral homeostasis Effects 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 201000008968 osteosarcoma Diseases 0.000 claims description 4
- 208000028169 periodontal disease Diseases 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- XGBRVSSTLMUVLT-IAIRZMIISA-N 1-methoxypropan-2-yl 3-[4-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoate Chemical group COCC(C)OC(=O)CCC1=CC=C(C#N)C(OC[C@H](O)CNC(C)(C)CC2CC3=CC=CC=C3C2)=C1 XGBRVSSTLMUVLT-IAIRZMIISA-N 0.000 claims description 3
- KJKUMORDTVRNOE-HSZRJFAPSA-N 3-[4-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-5-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoic acid Chemical compound C([C@H](O)CNC(C)(CC=1C=C2CCCC2=CC=1)C)OC1=CC(CCC(O)=O)=CC=C1C#N KJKUMORDTVRNOE-HSZRJFAPSA-N 0.000 claims description 3
- 102000055006 Calcitonin Human genes 0.000 claims description 3
- 108060001064 Calcitonin Proteins 0.000 claims description 3
- 208000037147 Hypercalcaemia Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000010191 Osteitis Deformans Diseases 0.000 claims description 3
- 208000027868 Paget disease Diseases 0.000 claims description 3
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims description 3
- 229960004015 calcitonin Drugs 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- GCILJQRRDBBUBX-UHFFFAOYSA-N ethyl 3-(4-cyano-3-hydroxyphenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=C(C#N)C(O)=C1 GCILJQRRDBBUBX-UHFFFAOYSA-N 0.000 claims description 3
- 230000000148 hypercalcaemia Effects 0.000 claims description 3
- 208000030915 hypercalcemia disease Diseases 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 230000036210 malignancy Effects 0.000 claims description 3
- 208000027202 mammary Paget disease Diseases 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- BFZDZPCIGYEJHA-YADHBBJMSA-N (2s)-2-amino-3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1-naphthalen-2-ylpropan-2-yl)amino]propoxy]-3-nitrophenyl]propanoic acid Chemical compound C([C@H](O)CNC(C)(CC=1C=C2C=CC=CC2=CC=1)C)OC1=CC=C(C[C@H](N)C(O)=O)C=C1[N+]([O-])=O BFZDZPCIGYEJHA-YADHBBJMSA-N 0.000 claims description 2
- 125000004893 1,1-dimethylethylamino group Chemical group CC(C)(C)N* 0.000 claims description 2
- ZCKMKRGGJZFAOG-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-ol Chemical compound C1=CC=C2CC(CC(C)(O)C)CC2=C1 ZCKMKRGGJZFAOG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004889 1-methylethylamino group Chemical group CC(C)N* 0.000 claims description 2
- RQPPSXWWVZBILZ-JOCHJYFZSA-N 3-[2-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoic acid Chemical compound C([C@H](O)CNC(C)(CC1CC2=CC=CC=C2C1)C)OC1=CC=CC(CCC(O)=O)=C1C#N RQPPSXWWVZBILZ-JOCHJYFZSA-N 0.000 claims description 2
- XITQUPZFKAOAOI-JOCHJYFZSA-N 3-[4-cyano-5-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]-2-fluorophenyl]propanoic acid Chemical compound C([C@H](O)CNC(C)(CC1CC2=CC=CC=C2C1)C)OC1=CC(CCC(O)=O)=C(F)C=C1C#N XITQUPZFKAOAOI-JOCHJYFZSA-N 0.000 claims description 2
- PKHQFUWTTXDRID-XMMPIXPASA-N 4-[2-cyano-3-[(2r)-2-hydroxy-3-[(2-methyl-1-naphthalen-2-ylpropan-2-yl)amino]propoxy]phenyl]butanoic acid Chemical compound C([C@H](O)CNC(C)(CC=1C=C2C=CC=CC2=CC=1)C)OC1=CC=CC(CCCC(O)=O)=C1C#N PKHQFUWTTXDRID-XMMPIXPASA-N 0.000 claims description 2
- MRESEBKQONYCSN-HSZRJFAPSA-N 4-[2-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]butanoic acid Chemical compound C([C@H](O)CNC(C)(CC1CC2=CC=CC=C2C1)C)OC1=CC=CC(CCCC(O)=O)=C1C#N MRESEBKQONYCSN-HSZRJFAPSA-N 0.000 claims description 2
- ANDWNEZTVWCWTQ-RUZDIDTESA-N 4-[4-cyano-3-[(2r)-2-hydroxy-3-[(2-methyl-1-naphthalen-2-ylpropan-2-yl)amino]propoxy]phenyl]butanoic acid Chemical compound C([C@H](O)CNC(C)(CC=1C=C2C=CC=CC2=CC=1)C)OC1=CC(CCCC(O)=O)=CC=C1C#N ANDWNEZTVWCWTQ-RUZDIDTESA-N 0.000 claims description 2
- RPOHCNSBSXNRIJ-XMMPIXPASA-N 4-[4-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]butanoic acid Chemical compound C([C@H](O)CNC(C)(CC1CC2=CC=CC=C2C1)C)OC1=CC(CCCC(O)=O)=CC=C1C#N RPOHCNSBSXNRIJ-XMMPIXPASA-N 0.000 claims description 2
- JCVLICPIZSYQEL-RUZDIDTESA-N 5-[4-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]pentanoic acid Chemical compound C([C@H](O)CNC(C)(CC1CC2=CC=CC=C2C1)C)OC1=CC(CCCCC(O)=O)=CC=C1C#N JCVLICPIZSYQEL-RUZDIDTESA-N 0.000 claims description 2
- 229940122361 Bisphosphonate Drugs 0.000 claims description 2
- 102000004171 Cathepsin K Human genes 0.000 claims description 2
- 108090000625 Cathepsin K Proteins 0.000 claims description 2
- 102100022337 Integrin alpha-V Human genes 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims description 2
- 108010048673 Vitronectin Receptors Proteins 0.000 claims description 2
- 239000000362 adenosine triphosphatase inhibitor Substances 0.000 claims description 2
- 239000005557 antagonist Substances 0.000 claims description 2
- 150000004663 bisphosphonates Chemical class 0.000 claims description 2
- 229940011871 estrogen Drugs 0.000 claims description 2
- 239000000262 estrogen Substances 0.000 claims description 2
- GKLSGASRWCMBDB-UHFFFAOYSA-N ethyl 3-(3-acetyloxy-4-cyanophenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=C(C#N)C(OC(C)=O)=C1 GKLSGASRWCMBDB-UHFFFAOYSA-N 0.000 claims description 2
- XZRINIMKJJEFMT-UHFFFAOYSA-N ethyl 3-(4-formyl-3-hydroxyphenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=C(C=O)C(O)=C1 XZRINIMKJJEFMT-UHFFFAOYSA-N 0.000 claims description 2
- PJWYQJZOMUBZBV-RUZDIDTESA-N ethyl 3-[2-cyano-3-[(2r)-2-hydroxy-3-[(2-methyl-1-naphthalen-2-ylpropan-2-yl)amino]propoxy]phenyl]propanoate Chemical compound CCOC(=O)CCC1=CC=CC(OC[C@H](O)CNC(C)(C)CC=2C=C3C=CC=CC3=CC=2)=C1C#N PJWYQJZOMUBZBV-RUZDIDTESA-N 0.000 claims description 2
- ZJWJGKAOAYRABW-UHFFFAOYSA-N ethyl 3-[3-hydroxy-4-(hydroxyiminomethyl)phenyl]propanoate Chemical compound CCOC(=O)CCC1=CC=C(C=NO)C(O)=C1 ZJWJGKAOAYRABW-UHFFFAOYSA-N 0.000 claims description 2
- WFBZUHNCOPBPPA-AREMUKBSSA-N ethyl 4-[2-cyano-3-[(2r)-2-hydroxy-3-[(2-methyl-1-naphthalen-2-ylpropan-2-yl)amino]propoxy]phenyl]butanoate Chemical compound CCOC(=O)CCCC1=CC=CC(OC[C@H](O)CNC(C)(C)CC=2C=C3C=CC=CC3=CC=2)=C1C#N WFBZUHNCOPBPPA-AREMUKBSSA-N 0.000 claims description 2
- JVTKSWDOADOJRM-HHHXNRCGSA-N ethyl 4-[3-cyano-4-[(2r)-2-hydroxy-3-[(2-methyl-1-naphthalen-2-ylpropan-2-yl)amino]propoxy]phenyl]butanoate Chemical compound N#CC1=CC(CCCC(=O)OCC)=CC=C1OC[C@H](O)CNC(C)(C)CC1=CC=C(C=CC=C2)C2=C1 JVTKSWDOADOJRM-HHHXNRCGSA-N 0.000 claims description 2
- JAOMNVGHIRSQDO-AREMUKBSSA-N ethyl 4-[3-cyano-4-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]butanoate Chemical compound N#CC1=CC(CCCC(=O)OCC)=CC=C1OC[C@H](O)CNC(C)(C)CC1CC2=CC=CC=C2C1 JAOMNVGHIRSQDO-AREMUKBSSA-N 0.000 claims description 2
- SYADYOYIVXAQAO-HHHXNRCGSA-N ethyl 4-[4-cyano-3-[(2r)-2-hydroxy-3-[(2-methyl-1-naphthalen-2-ylpropan-2-yl)amino]propoxy]phenyl]butanoate Chemical compound CCOC(=O)CCCC1=CC=C(C#N)C(OC[C@H](O)CNC(C)(C)CC=2C=C3C=CC=CC3=CC=2)=C1 SYADYOYIVXAQAO-HHHXNRCGSA-N 0.000 claims description 2
- ITYDRDKUXNKSAY-UHFFFAOYSA-N methyl 2-(2,3-dihydro-1h-inden-2-yl)acetate Chemical compound C1=CC=C2CC(CC(=O)OC)CC2=C1 ITYDRDKUXNKSAY-UHFFFAOYSA-N 0.000 claims description 2
- PEWPUBAXAIXKCY-HHHXNRCGSA-N pentan-3-yl 3-[4-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoate Chemical compound CCC(CC)OC(=O)CCC1=CC=C(C#N)C(OC[C@H](O)CNC(C)(C)CC2CC3=CC=CC=C3C2)=C1 PEWPUBAXAIXKCY-HHHXNRCGSA-N 0.000 claims description 2
- QSYUQBQDXRVKLI-MUUNZHRXSA-N pentyl 3-[4-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoate Chemical compound CCCCCOC(=O)CCC1=CC=C(C#N)C(OC[C@H](O)CNC(C)(C)CC2CC3=CC=CC=C3C2)=C1 QSYUQBQDXRVKLI-MUUNZHRXSA-N 0.000 claims description 2
- 229940044551 receptor antagonist Drugs 0.000 claims description 2
- 239000002464 receptor antagonist Substances 0.000 claims description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 2
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 claims description 2
- 235000005282 vitamin D3 Nutrition 0.000 claims description 2
- 239000011647 vitamin D3 Substances 0.000 claims description 2
- 229940021056 vitamin d3 Drugs 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- PJOYQRCYAHRICJ-AREMUKBSSA-N 2-methoxyethyl 3-[4-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoate Chemical compound COCCOC(=O)CCC1=CC=C(C#N)C(OC[C@H](O)CNC(C)(C)CC2CC3=CC=CC=C3C2)=C1 PJOYQRCYAHRICJ-AREMUKBSSA-N 0.000 claims 1
- XCBMSUBJOOBHIW-XMMPIXPASA-N 3-[4-cyano-3-[(2r)-2-hydroxy-3-[[2-methyl-1-(5,6,7,8-tetrahydronaphthalen-2-yl)propan-2-yl]amino]propoxy]phenyl]propanoic acid Chemical compound C([C@H](O)CNC(C)(CC=1C=C2CCCCC2=CC=1)C)OC1=CC(CCC(O)=O)=CC=C1C#N XCBMSUBJOOBHIW-XMMPIXPASA-N 0.000 claims 1
- HRMPEVZAIUQZGU-MUUNZHRXSA-N 5-aminopentyl 3-[4-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoate Chemical compound C([C@H](O)CNC(C)(CC1CC2=CC=CC=C2C1)C)OC1=CC(CCC(=O)OCCCCCN)=CC=C1C#N HRMPEVZAIUQZGU-MUUNZHRXSA-N 0.000 claims 1
- UZQKAIDDBSCMPT-HHHXNRCGSA-N butyl 3-[4-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoate Chemical compound CCCCOC(=O)CCC1=CC=C(C#N)C(OC[C@H](O)CNC(C)(C)CC2CC3=CC=CC=C3C2)=C1 UZQKAIDDBSCMPT-HHHXNRCGSA-N 0.000 claims 1
- 102000015694 estrogen receptors Human genes 0.000 claims 1
- 108010038795 estrogen receptors Proteins 0.000 claims 1
- DMWBVRRUBDZTBK-VWLOTQADSA-N ethyl 3-[4-cyano-3-[(2s)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoate Chemical compound CCOC(=O)CCC1=CC=C(C#N)C(OC[C@@H](O)CNC(C)(C)CC2CC3=CC=CC=C3C2)=C1 DMWBVRRUBDZTBK-VWLOTQADSA-N 0.000 claims 1
- STTWWZRVCGJXQP-XMMPIXPASA-N ethyl 3-[4-cyano-5-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]-2-fluorophenyl]propanoate Chemical compound C1=C(F)C(CCC(=O)OCC)=CC(OC[C@H](O)CNC(C)(C)CC2CC3=CC=CC=C3C2)=C1C#N STTWWZRVCGJXQP-XMMPIXPASA-N 0.000 claims 1
- GCLKSISMFRGUIM-WJOKGBTCSA-N octyl 3-[4-cyano-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoate Chemical compound CCCCCCCCOC(=O)CCC1=CC=C(C#N)C(OC[C@H](O)CNC(C)(C)CC2CC3=CC=CC=C3C2)=C1 GCLKSISMFRGUIM-WJOKGBTCSA-N 0.000 claims 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 59
- 239000011575 calcium Substances 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000003921 oil Substances 0.000 description 26
- 235000019198 oils Nutrition 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 23
- 235000019439 ethyl acetate Nutrition 0.000 description 20
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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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
- A61P5/22—Drugs for disorders of the endocrine system of the parathyroid hormones for decreasing, blocking or antagonising the activity of calcitonin
-
- 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
- C07C211/30—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 the six-membered aromatic ring being part of a condensed ring system formed by two rings
-
- 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
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/616—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17768300P | 2000-01-24 | 2000-01-24 | |
| PCT/US2001/002402 WO2001053254A1 (en) | 2000-01-24 | 2001-01-24 | Calcilytic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG106942A true BG106942A (bg) | 2003-01-31 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG106942A BG106942A (bg) | 2000-01-24 | 2002-07-23 | Калцилитични съединения |
Country Status (31)
| Country | Link |
|---|---|
| EP (2) | EP2141146A1 (de) |
| JP (1) | JP2003520265A (de) |
| KR (1) | KR20020073179A (de) |
| CN (1) | CN1396906A (de) |
| AP (1) | AP2002002547A0 (de) |
| AR (1) | AR030684A1 (de) |
| AT (1) | ATE423762T1 (de) |
| AU (1) | AU764746B2 (de) |
| BG (1) | BG106942A (de) |
| BR (1) | BR0107592A (de) |
| CA (1) | CA2397802A1 (de) |
| CO (1) | CO5251398A1 (de) |
| DE (1) | DE60137755D1 (de) |
| DZ (1) | DZ3284A1 (de) |
| EA (1) | EA200200798A1 (de) |
| ES (1) | ES2322641T3 (de) |
| HK (1) | HK1051356A1 (de) |
| HU (1) | HUP0204106A3 (de) |
| IL (1) | IL150398A0 (de) |
| MA (1) | MA25651A1 (de) |
| MX (1) | MXPA02007173A (de) |
| MY (1) | MY159417A (de) |
| NO (1) | NO20023508L (de) |
| NZ (1) | NZ519480A (de) |
| OA (1) | OA12163A (de) |
| PE (1) | PE20011062A1 (de) |
| PL (1) | PL356808A1 (de) |
| SK (1) | SK10742002A3 (de) |
| UY (1) | UY26556A1 (de) |
| WO (1) | WO2001053254A1 (de) |
| ZA (1) | ZA200205832B (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1308436B1 (de) * | 2000-08-11 | 2008-10-15 | Japan Tobacco Inc. | Calciumrezeptor-antagonisten |
| JP2004514659A (ja) * | 2000-10-25 | 2004-05-20 | スミスクライン・ビーチャム・コーポレイション | カルシライティック化合物 |
| MY143244A (en) * | 2002-11-26 | 2011-04-15 | Smithkline Beecham Corp | Calcilytic compounds |
| EP1619180B1 (de) | 2003-04-23 | 2009-12-16 | Japan Tobacco Inc. | CaSR-ANTAGONIST |
| JP2007523076A (ja) * | 2004-02-06 | 2007-08-16 | スミスクライン・ビーチャム・コーポレイション | カルシウム受容体アンタゴニスト化合物 |
| WO2005077886A1 (en) * | 2004-02-06 | 2005-08-25 | Smithkline Beecham Corporation | Calcilytic compounds |
| AU2009255156B2 (en) | 2008-06-05 | 2013-03-14 | Asahi Kasei Pharma Corporation | Sulfonamide compound and application thereof |
| CN102307847A (zh) | 2008-12-24 | 2012-01-04 | 第一三共株式会社 | 茚满基化合物 |
| CN107417594B (zh) * | 2017-05-08 | 2020-03-27 | 凯莱英医药集团（天津）股份有限公司 | 一种酰胺醇解的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE2530613A1 (de) * | 1974-11-01 | 1976-05-06 | Haessle Ab | Aminderivate, verfahren zu deren herstellung und sie enthaltende arzneimittel |
| US4234595A (en) * | 1977-07-13 | 1980-11-18 | Mead Johnson & Company | 3-Indolyl-tertiary butylaminopropanols |
| FR2533210A1 (fr) * | 1982-09-17 | 1984-03-23 | Lyon I Universite Claude | Edulcorants de synthese |
| DD298506A5 (de) * | 1988-12-30 | 1992-02-27 | Ernst-Moritz-Arndt-Universitaet Greifswald,De | Verfahren zur herstellung halogensubstituierter 1-phenoxy-3-alkylamino-propan-2-ole |
| DE4040186A1 (de) * | 1989-12-20 | 1991-06-27 | Hoechst Ag | Hypoglykaemisch aktive propandiolaminderivate mit insulin-aehnlicher wirkung und deren verwendung, neue propandiolaminderivate, diese substanzen enthaltende pharmazeutische zubereitungen und ihre verwendung zur behandlung von krankheiten |
| WO1997037967A1 (en) * | 1996-04-09 | 1997-10-16 | Nps Pharmaceuticals, Inc. | Calcilytic compounds |
| UY24949A1 (es) * | 1997-04-08 | 2001-04-30 | Smithkline Beecham Corp | Compuestos calcilíticos |
| AR014975A1 (es) * | 1998-04-08 | 2001-04-11 | Nps Pharma Inc | Compuestos calciliticos, una composicion farmaceutica que los comprende, y el uso de los mismos para la fabricacion de un medicamento |
| MY121054A (en) * | 1998-04-08 | 2005-12-30 | Smithkline Beecham Corp | Calcilytic compounds as calcium receptor antagonists. |
| ECSP003590A (es) * | 1999-07-31 | 2002-02-25 | Smithkline Beecham Corp | Compuestos calcioliticos |
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2001
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- 2001-01-24 DZ DZ013284A patent/DZ3284A1/fr active
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- 2001-01-24 HK HK03102155.4A patent/HK1051356A1/zh unknown
- 2001-01-24 AU AU37966/01A patent/AU764746B2/en not_active Expired
- 2001-01-24 EA EA200200798A patent/EA200200798A1/ru unknown
- 2001-01-24 KR KR1020027009415A patent/KR20020073179A/ko not_active Withdrawn
- 2001-01-24 HU HU0204106A patent/HUP0204106A3/hu unknown
- 2001-01-24 EP EP01910349A patent/EP1254106B1/de not_active Expired - Lifetime
- 2001-01-24 CO CO01005224A patent/CO5251398A1/es not_active Application Discontinuation
- 2001-01-24 SK SK1074-2002A patent/SK10742002A3/sk not_active Application Discontinuation
- 2001-01-24 JP JP2001553259A patent/JP2003520265A/ja not_active Withdrawn
- 2001-01-24 DE DE60137755T patent/DE60137755D1/de not_active Expired - Lifetime
- 2001-01-24 AT AT01910349T patent/ATE423762T1/de not_active IP Right Cessation
- 2001-01-24 BR BR0107592-6A patent/BR0107592A/pt not_active IP Right Cessation
- 2001-01-24 MX MXPA02007173A patent/MXPA02007173A/es unknown
- 2001-01-24 PL PL01356808A patent/PL356808A1/xx not_active Application Discontinuation
- 2001-01-24 AP APAP/P/2002/002547A patent/AP2002002547A0/en unknown
-
2002
- 2002-07-22 ZA ZA200205832A patent/ZA200205832B/en unknown
- 2002-07-23 BG BG106942A patent/BG106942A/bg unknown
- 2002-07-23 NO NO20023508A patent/NO20023508L/no unknown
- 2002-07-24 MA MA26743A patent/MA25651A1/fr unknown
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