BG106942A - Калцилитични съединения - Google Patents

Калцилитични съединения Download PDF

Info

Publication number: BG106942A
Authority: BG; Bulgaria
Prior art keywords: hydroxy; phenyl; propoxy; cyano; indan
Prior art date: 2000-01-24

Application number

BG106942A

Other languages

Bulgarian (bg)

English (en)

Inventor

Amparo Lago

James Callahan

Pradio BHATNAGAR

MAR Eric DEL

William BRYAN

Joelle BURGESS

Original Assignee

Smithkline Beecham Corporation

Nps Pharmaceuticals, Inc

Priority date (The priority date 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 date listed.)

2000-01-24

Filing date

2002-07-23

Publication date

2003-01-31

2002-07-23 Application filed by Smithkline Beecham Corporation, Nps Pharmaceuticals, Inc filed Critical Smithkline Beecham Corporation

2003-01-31 Publication of BG106942A publication Critical patent/BG106942A/bg

Links

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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235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
ITVAJPHHXPJNHZ-UHFFFAOYSA-N tert-butyl 2-hydroxyhexanoate Chemical compound CCCCC(O)C(=O)OC(C)(C)C ITVAJPHHXPJNHZ-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
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
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
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230000002588 toxic effect Effects 0.000 description 1
230000007704 transition Effects 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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238000001291 vacuum drying Methods 0.000 description 1
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239000011701 zinc Substances 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
- 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
- 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
- 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
- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- 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
- 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)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Obesity (AREA)
Hematology (AREA)
Immunology (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)

BG106942A 2000-01-24 2002-07-23 Калцилитични съединения BG106942A (bg)

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

ID=22649559

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)	EP1254106B1 (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)	NO20023508D0 (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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE411275T1 (de)	2000-08-11	2008-10-15	Japan Tobacco Inc	Calciumrezeptor-antagonisten
ES2273909T3 (es) *	2000-10-25	2007-05-16	Smithkline Beecham Corporation	Compuestos calciliticos.
TWI316511B (en)	2002-11-26	2009-11-01	Smithkline Beecham Corp	Calcilytic compounds
BRPI0407097A (pt)	2003-04-23	2006-01-24	Japan Tobacco Inc	Antagonista do casr
US20070155819A1 (en) *	2004-02-06	2007-07-05	Marquis Robert W Jr	Calcilytic compounds
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
CN102056897B (zh)	2008-06-05	2014-05-07	旭化成制药株式会社	磺酰胺化合物及其用途
NZ593676A (en)	2008-12-24	2012-06-29	Daiichi Sankyo Co Ltd	Calcium-sensing receptor antagonists
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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
DE69733649T2 (de) *	1996-04-09	2006-05-18	NPS Pharmaceuticals, Inc., Salt Lake City	Calcylitische verbindungen
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
PE20000415A1 (es) *	1998-04-08	2000-05-21	Smithkline Beecham Corp	Compuestos calciliticos
CO5180628A1 (es) *	1999-07-31	2002-07-30	Smithkline Beecham Corp	Compuestos calcioliticos

2001
- 2001-01-22 AR ARP010100268A patent/AR030684A1/es not_active Application Discontinuation
- 2001-01-22 MY MYPI20010288A patent/MY159417A/en unknown
- 2001-01-23 PE PE2001000069A patent/PE20011062A1/es not_active Application Discontinuation
- 2001-01-24 WO PCT/US2001/002402 patent/WO2001053254A1/en not_active Ceased
- 2001-01-24 DZ DZ013284A patent/DZ3284A1/fr active
- 2001-01-24 CO CO01005224A patent/CO5251398A1/es not_active Application Discontinuation
- 2001-01-24 OA OA1200200218A patent/OA12163A/en unknown
- 2001-01-24 DE DE60137755T patent/DE60137755D1/de not_active Expired - Lifetime
- 2001-01-24 HK HK03102155.4A patent/HK1051356A1/zh unknown
- 2001-01-24 EP EP01910349A patent/EP1254106B1/de not_active Expired - Lifetime
- 2001-01-24 AT AT01910349T patent/ATE423762T1/de not_active IP Right Cessation
- 2001-01-24 KR KR1020027009415A patent/KR20020073179A/ko not_active Withdrawn
- 2001-01-24 AP APAP/P/2002/002547A patent/AP2002002547A0/en unknown
- 2001-01-24 AU AU37966/01A patent/AU764746B2/en not_active Expired
- 2001-01-24 MX MXPA02007173A patent/MXPA02007173A/es unknown
- 2001-01-24 BR BR0107592-6A patent/BR0107592A/pt not_active IP Right Cessation
- 2001-01-24 HU HU0204106A patent/HUP0204106A3/hu unknown
- 2001-01-24 IL IL15039801A patent/IL150398A0/xx unknown
- 2001-01-24 EP EP09002553A patent/EP2141146A1/de not_active Withdrawn
- 2001-01-24 NZ NZ519480A patent/NZ519480A/en not_active IP Right Cessation
- 2001-01-24 ES ES01910349T patent/ES2322641T3/es not_active Expired - Lifetime
- 2001-01-24 EA EA200200798A patent/EA200200798A1/ru unknown
- 2001-01-24 UY UY26556A patent/UY26556A1/es not_active Application Discontinuation
- 2001-01-24 PL PL01356808A patent/PL356808A1/xx not_active Application Discontinuation
- 2001-01-24 SK SK1074-2002A patent/SK10742002A3/sk not_active Application Discontinuation
- 2001-01-24 CA CA002397802A patent/CA2397802A1/en not_active Abandoned
- 2001-01-24 JP JP2001553259A patent/JP2003520265A/ja not_active Withdrawn
- 2001-01-24 CN CN01804024A patent/CN1396906A/zh active Pending
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/NO20023508D0/no unknown
- 2002-07-24 MA MA26743A patent/MA25651A1/fr unknown

Also Published As

Publication number	Publication date
DE60137755D1 (de)	2009-04-09
DZ3284A1 (fr)	2001-07-26
EA200200798A1 (ru)	2002-12-26
HK1051356A1 (zh)	2003-08-01
IL150398A0 (en)	2002-12-01
AU3796601A (en)	2001-07-31
NZ519480A (en)	2004-05-28
HUP0204106A2 (hu)	2003-03-28
MY159417A (en)	2017-01-13
EP1254106A1 (de)	2002-11-06
AP2002002547A0 (en)	2002-06-30
SK10742002A3 (sk)	2002-12-03
EP2141146A1 (de)	2010-01-06
HUP0204106A3 (en)	2003-05-28
CA2397802A1 (en)	2001-07-26
KR20020073179A (ko)	2002-09-19
NO20023508L (no)	2002-07-23
MA25651A1 (fr)	2002-12-31
ES2322641T3 (es)	2009-06-24
MXPA02007173A (es)	2004-09-06
PE20011062A1 (es)	2001-11-29
ATE423762T1 (de)	2009-03-15
JP2003520265A (ja)	2003-07-02
ZA200205832B (en)	2003-03-05
AR030684A1 (es)	2003-09-03
EP1254106A4 (de)	2005-09-14
OA12163A (en)	2006-05-08
CN1396906A (zh)	2003-02-12
AU764746B2 (en)	2003-08-28
UY26556A1 (es)	2001-08-27
WO2001053254A1 (en)	2001-07-26
PL356808A1 (en)	2004-07-12
CO5251398A1 (es)	2003-02-28
NO20023508D0 (no)	2002-07-23
EP1254106B1 (de)	2009-02-25
BR0107592A (pt)	2002-11-19

Publication	Publication Date	Title
US6335338B1 (en)	2002-01-01	Calcilytic compounds
US6417215B1 (en)	2002-07-09	Calcilytic compounds
BG106942A (bg)	2003-01-31	Калцилитични съединения
JP2010513564A (ja)	2010-04-30	カルシリティック化合物
US20040009980A1 (en)	2004-01-15	Calcilytic compounds
US6864267B2 (en)	2005-03-08	Calcilytic compounds
WO2002007673A2 (en)	2002-01-31	Calcilytic compounds
AU2001276923A1 (en)	2002-05-02	Calcilytic compounds
EP1383511B1 (de)	2006-10-25	Kalzilytische verbindungen
US7109238B2 (en)	2006-09-19	Calcilytic compounds
US6291459B1 (en)	2001-09-18	Calcilytic compounds
US20070155819A1 (en)	2007-07-05	Calcilytic compounds
EP1664013B1 (de)	2008-05-14	Kalzilytische verbindungen
US20080234370A1 (en)	2008-09-25	Calcilytic Compounds