ZA200504104B - Calcilytic compounds - Google Patents
Calcilytic compounds Download PDFInfo
- Publication number
- ZA200504104B ZA200504104B ZA200504104A ZA200504104A ZA200504104B ZA 200504104 B ZA200504104 B ZA 200504104B ZA 200504104 A ZA200504104 A ZA 200504104A ZA 200504104 A ZA200504104 A ZA 200504104A ZA 200504104 B ZA200504104 B ZA 200504104B
- Authority
- ZA
- South Africa
- Prior art keywords
- indan
- dimethyl
- hydroxy
- phenyl
- propoxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 33
- 230000001126 calcilytic effect Effects 0.000 title description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 108090000445 Parathyroid hormone Proteins 0.000 claims description 11
- 230000002159 abnormal effect Effects 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000004494 ethyl ester group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 210000000988 bone and bone Anatomy 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000035876 healing Effects 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- -1 2-indan-2-yl- 1,1-dimethyl-ethylamino Chemical group 0.000 claims description 2
- 208000010392 Bone Fractures Diseases 0.000 claims description 2
- 206010017076 Fracture Diseases 0.000 claims description 2
- 208000037147 Hypercalcaemia Diseases 0.000 claims description 2
- 208000010191 Osteitis Deformans Diseases 0.000 claims description 2
- 208000027868 Paget disease Diseases 0.000 claims description 2
- 102000003982 Parathyroid hormone Human genes 0.000 claims description 2
- 230000000148 hypercalcaemia Effects 0.000 claims description 2
- 208000030915 hypercalcemia disease Diseases 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 208000027202 mammary Paget disease Diseases 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 230000004079 mineral homeostasis Effects 0.000 claims description 2
- 239000000199 parathyroid hormone Substances 0.000 claims description 2
- 229960001319 parathyroid hormone Drugs 0.000 claims description 2
- 208000028169 periodontal disease Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- MBEVSMZJMIQVBG-UHFFFAOYSA-N 2-(hydroxymethyl)guanidine Chemical compound NC(N)=NCO MBEVSMZJMIQVBG-UHFFFAOYSA-N 0.000 claims 1
- NOYLNBROWKEFEX-JOCHJYFZSA-N 3-[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)=C1 NOYLNBROWKEFEX-JOCHJYFZSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- YJJCBPAEWVURMJ-UHFFFAOYSA-N ethyl propanoate;hydrochloride Chemical compound Cl.CCOC(=O)CC YJJCBPAEWVURMJ-UHFFFAOYSA-N 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- 239000011575 calcium Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 11
- 229910052791 calcium Inorganic materials 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 102100036893 Parathyroid hormone Human genes 0.000 description 9
- 102000013830 Calcium-Sensing Receptors Human genes 0.000 description 8
- 108010050543 Calcium-Sensing Receptors Proteins 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 229940095574 propionic acid Drugs 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 230000028327 secretion Effects 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 230000000849 parathyroid Effects 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 230000004094 calcium homeostasis Effects 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 210000003771 C cell Anatomy 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000000763 evoking effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 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 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZYUZXUFBGPSCBM-ZCFIWIBFSA-N (2r)-2-[(5-bromo-2,3-difluorophenoxy)methyl]oxirane Chemical compound FC1=CC(Br)=CC(OC[C@@H]2OC2)=C1F ZYUZXUFBGPSCBM-ZCFIWIBFSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RPEPGIOVXBBUMJ-UHFFFAOYSA-N 2,3-difluorophenol Chemical compound OC1=CC=CC(F)=C1F RPEPGIOVXBBUMJ-UHFFFAOYSA-N 0.000 description 1
- MPGSHUYHOPADTQ-ZMBIFBSDSA-N 3-[3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]-4-fluorophenyl]propanoic acid;hydrochloride Chemical compound Cl.C([C@H](O)CNC(C)(CC1CC2=CC=CC=C2C1)C)OC1=CC(CCC(O)=O)=CC=C1F MPGSHUYHOPADTQ-ZMBIFBSDSA-N 0.000 description 1
- JZAVCMMYGSROJP-UHFFFAOYSA-N 4-bromo-2,3-difluorophenol Chemical compound OC1=CC=C(Br)C(F)=C1F JZAVCMMYGSROJP-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- 208000006386 Bone Resorption Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229910004250 CaCoO Inorganic materials 0.000 description 1
- 229940123613 Calcium receptor antagonist Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- PTVSRINJXWDIKP-UHFFFAOYSA-N Ethyl 4-pentenoate Chemical compound CCOC(=O)CCC=C PTVSRINJXWDIKP-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 241001272567 Hominoidea Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 208000000038 Hypoparathyroidism Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 102000018697 Membrane Proteins Human genes 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 101100382264 Mus musculus Ca14 gene Proteins 0.000 description 1
- 101100112373 Mus musculus Ctsm gene Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000215040 Neso Species 0.000 description 1
- 101100094962 Salmo salar salarin gene Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000005841 biaryl group Chemical group 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 230000024279 bone resorption Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 230000036755 cellular response Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000001739 density measurement Methods 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- BFTJMPDRAYEKQT-UHFFFAOYSA-N ethyl 3-(4-bromo-3-hydroxyphenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=C(Br)C(O)=C1 BFTJMPDRAYEKQT-UHFFFAOYSA-N 0.000 description 1
- BBYKLXWMRXTOPK-GNAFDRTKSA-N ethyl 3-[3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]-4-fluorophenyl]propanoate;hydrochloride Chemical compound Cl.CCOC(=O)CCC1=CC=C(F)C(OC[C@H](O)CNC(C)(C)CC2CC3=CC=CC=C3C2)=C1 BBYKLXWMRXTOPK-GNAFDRTKSA-N 0.000 description 1
- IUEWFQCGYNJBBU-GNAFDRTKSA-N ethyl 3-[4-bromo-3-[(2r)-3-[[1-(2,3-dihydro-1h-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoate;hydrochloride Chemical compound Cl.CCOC(=O)CCC1=CC=C(Br)C(OC[C@H](O)CNC(C)(C)CC2CC3=CC=CC=C3C2)=C1 IUEWFQCGYNJBBU-GNAFDRTKSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003722 extracellular fluid Anatomy 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000003284 homeostatic effect Effects 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 210000002997 osteoclast Anatomy 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
-
- 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
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/34—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- 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
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US42910502P | 2002-11-26 | 2002-11-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200504104B true ZA200504104B (en) | 2006-03-29 |
Family
ID=32393505
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200504104A ZA200504104B (en) | 2002-11-26 | 2006-02-07 | Calcilytic compounds |
Country Status (33)
Country | Link |
---|---|
US (6) | US7514473B2 (pt) |
EP (1) | EP1569892B1 (pt) |
JP (1) | JP4489597B2 (pt) |
KR (2) | KR20050086786A (pt) |
CN (1) | CN1325466C (pt) |
AP (1) | AP2113A (pt) |
AR (1) | AR042132A1 (pt) |
AU (1) | AU2003291157C1 (pt) |
BR (1) | BR0316544A (pt) |
CA (1) | CA2507226C (pt) |
CO (1) | CO5570664A2 (pt) |
CY (1) | CY1113083T1 (pt) |
DK (1) | DK1569892T3 (pt) |
EA (1) | EA009603B1 (pt) |
ES (1) | ES2388277T3 (pt) |
HK (1) | HK1082914A1 (pt) |
IL (1) | IL168704A (pt) |
IS (1) | IS2897B (pt) |
MA (1) | MA27528A1 (pt) |
MX (1) | MXPA05005574A (pt) |
MY (1) | MY143244A (pt) |
NO (1) | NO332304B1 (pt) |
NZ (1) | NZ540275A (pt) |
OA (1) | OA12962A (pt) |
PE (1) | PE20040845A1 (pt) |
PL (1) | PL211571B1 (pt) |
PT (1) | PT1569892E (pt) |
SI (1) | SI1569892T1 (pt) |
TW (1) | TWI316511B (pt) |
UA (1) | UA81642C2 (pt) |
UY (1) | UY28089A1 (pt) |
WO (1) | WO2004047751A2 (pt) |
ZA (1) | ZA200504104B (pt) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI316511B (en) | 2002-11-26 | 2009-11-01 | Smithkline Beecham Corp | Calcilytic compounds |
WO2005077886A1 (en) * | 2004-02-06 | 2005-08-25 | Smithkline Beecham Corporation | Calcilytic compounds |
TW200845956A (en) * | 2006-12-18 | 2008-12-01 | Smithkline Beecham Corp | Calcilytic compounds |
JP5025795B2 (ja) * | 2008-06-05 | 2012-09-12 | 旭化成ファーマ株式会社 | スルホンアミド化合物及びその用途 |
CN102307847A (zh) | 2008-12-24 | 2012-01-04 | 第一三共株式会社 | 茚满基化合物 |
GB201217330D0 (en) | 2012-09-28 | 2012-11-14 | Univ Cardiff | Therapeutic for treating inflammatory lung disorders |
WO2015196205A1 (en) * | 2014-06-20 | 2015-12-23 | Glaxosmithkline Llc | Method of using calcilytic compounds to treat diseases of abnormal glucose or insulin levels |
Family Cites Families (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE298506C (pt) | ||||
US643656A (en) * | 1898-09-03 | 1900-02-20 | Francis Keil | Mold for lock-cylinders and key-hubs. |
ES421076A1 (es) | 1973-12-01 | 1976-04-01 | Andreu Sa Dr | Procedimiento para la obtencion de 1-ariloxi-3-aralquilami-no-2-propanoles. |
ES442062A1 (es) | 1975-10-24 | 1977-04-01 | Andreu Sa Dr | Procedimiento para la obtencion de 1-ariloxi-2-hidroxi-3- alquilaminopropanos. |
DE2644833A1 (de) | 1976-10-05 | 1978-04-20 | Boehringer Sohn Ingelheim | Neue 1-aryloxy-2-hydroxy-3-alkylenaminopropane und verfahren zu ihrer herstellung |
CH618335A5 (pt) * | 1977-05-31 | 1980-07-31 | Arnegger Richard E | |
US4234595A (en) * | 1977-07-13 | 1980-11-18 | Mead Johnson & Company | 3-Indolyl-tertiary butylaminopropanols |
IT1101724B (it) * | 1978-12-05 | 1985-10-07 | Erba Carlo Spa | Derivati morfolinici e fenossiprofanolaminici e procedimento per la loro preparazione |
IL56369A (en) | 1978-01-20 | 1984-05-31 | Erba Farmitalia | Alpha-phenoxybenzyl propanolamine derivatives,their preparation and pharmaceutical compositions comprising them |
GB2014968A (en) | 1978-02-24 | 1979-09-05 | Pearson J | Article handling apparatus |
US4495352A (en) | 1979-02-13 | 1985-01-22 | Mead Johnson & Company | Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols |
ES480066A1 (es) | 1979-04-28 | 1980-04-01 | Especialid Latin Medicam Unive | Procedimiento de obtencion de 1-4-cloro-&,&-dimetil-benceno-etanamino-2-oxi-3 ariloxi propanos. |
DE3544172A1 (de) | 1985-12-13 | 1987-06-19 | Lentia Gmbh | Neue kristalline salze von aryloxy-propanolaminen, verfahren zu ihrer herstellung und ihre verwendung |
FR2601008B1 (fr) | 1986-07-03 | 1990-03-30 | Sanofi Sa | Procede de synthese stereospecifique de derives de l'indole |
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 |
HN1996000101A (es) | 1996-02-28 | 1997-06-26 | Inc Pfizer | Terapia combinada para la osteoporosis |
EA002984B1 (ru) | 1996-04-09 | 2002-12-26 | Эн Пи Эс Фармасьютикалз, Инк. | Кальцилитические соединения, фармацевтические композиции и способ скрининга кальцилитических соединений |
US6818660B2 (en) | 1996-04-09 | 2004-11-16 | Nps Pharmaceuticals, Inc. | Calcilytic compounds |
US20020019440A1 (en) | 1996-11-05 | 2002-02-14 | Virbac Sa | Aryloxypropanolamine derivatives, method of preparation and applications thereof |
TW483881B (en) | 1996-12-03 | 2002-04-21 | Nps Pharma Inc | Calcilytic compounds |
US7202261B2 (en) | 1996-12-03 | 2007-04-10 | Nps Pharmaceuticals, Inc. | Calcilytic compounds |
JP2001519813A (ja) | 1997-04-04 | 2001-10-23 | スミスクライン・ビーチャム・コーポレイション | カルシウム溶解性化合物 |
UY24949A1 (es) | 1997-04-08 | 2001-04-30 | Smithkline Beecham Corp | Compuestos calcilíticos |
DE19913753A1 (de) | 1998-04-01 | 1999-10-07 | Mannesmann Rexroth Ag | Verfahren zur Bildung des Mittelwertes |
MY121054A (en) | 1998-04-08 | 2005-12-30 | Smithkline Beecham Corp | Calcilytic compounds as calcium receptor antagonists. |
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 |
US6291459B1 (en) | 1998-08-12 | 2001-09-18 | Smithkline Beecham Corporation | Calcilytic compounds |
WO2000009491A1 (en) | 1998-08-12 | 2000-02-24 | Smithkline Beecham Corporation | Calcilytic compounds |
PE20001456A1 (es) | 1999-02-02 | 2001-01-28 | Smithkline Beecham Corp | Compuestos calcioliticos |
WO2001007026A2 (en) | 1999-07-22 | 2001-02-01 | Eli Lilly And Company | Improved method of treating type ii diabetes and obesity |
ECSP003590A (es) | 1999-07-31 | 2002-02-25 | Smithkline Beecham Corp | Compuestos calcioliticos |
US20030018203A1 (en) | 2002-07-17 | 2003-01-23 | Largo Maria Amparo | Calcilytic compounds |
AR030684A1 (es) | 2000-01-24 | 2003-09-03 | Smithkline Beecham Corp | Compuestos calciliticos, uso de dichos compuestos en la manufactura de medicamentos, e intermediarios utiles en la preparacion de dichos compuestos |
CZ2003142A3 (cs) | 2000-07-21 | 2003-06-18 | Smithkline Beecham Corporation | Kalcilytické sloučeniny |
EP1383511B1 (en) | 2000-10-25 | 2006-10-25 | SmithKline Beecham Corporation | Calcilytic compounds |
CZ20031144A3 (cs) | 2000-10-25 | 2004-08-18 | Smithklineábeechamácorporation | Kalcilytické sloučeniny |
WO2002072760A2 (en) | 2001-03-08 | 2002-09-19 | Smithkline Beecham Corporation | Pcra helicase inhibitors |
US6864267B2 (en) | 2001-07-16 | 2005-03-08 | Smithkline Beecham Corporation | Calcilytic compounds |
TWI316511B (en) * | 2002-11-26 | 2009-11-01 | Smithkline Beecham Corp | Calcilytic compounds |
ATE489368T1 (de) | 2003-04-07 | 2010-12-15 | Nps Pharma Inc | Pyrimidinonverbindungen als calcilytica |
WO2005018561A2 (en) | 2003-08-20 | 2005-03-03 | Nitromed, Inc. | Nitrosated and nitrosylated cardiovascular compounds, compositions and methods of use |
TW200524892A (en) | 2003-09-24 | 2005-08-01 | Glaxo Group Ltd | Calcilytic compounds |
WO2005030746A1 (en) | 2003-09-24 | 2005-04-07 | Glaxo Group Limited | 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 |
NL1025457C1 (nl) | 2004-02-11 | 2005-08-12 | Rudolf Johannes Gerardus Hoorn | Haspelrem. |
US20080300292A1 (en) | 2004-11-08 | 2008-12-04 | Nitromed, Inc | Nitrosated and Nitrosylated Compounds, Compositions and Methods for the Treatment of Ophthalmic Disorders |
WO2006078995A1 (en) | 2005-01-21 | 2006-07-27 | Nitromed, Inc. | Cardiovascular compounds comprising heterocyclic nitric oxide donor group compositions and methods of use |
-
2003
- 2003-11-24 TW TW092132853A patent/TWI316511B/zh not_active IP Right Cessation
- 2003-11-24 AR ARP030104333A patent/AR042132A1/es not_active Application Discontinuation
- 2003-11-24 UY UY28089A patent/UY28089A1/es unknown
- 2003-11-24 MY MYPI20034511A patent/MY143244A/en unknown
- 2003-11-25 OA OA1200500152A patent/OA12962A/en unknown
- 2003-11-25 DK DK03783752.3T patent/DK1569892T3/da active
- 2003-11-25 PL PL376965A patent/PL211571B1/pl unknown
- 2003-11-25 BR BR0316544-2A patent/BR0316544A/pt active Search and Examination
- 2003-11-25 UA UAA200505005A patent/UA81642C2/ru unknown
- 2003-11-25 KR KR1020057009379A patent/KR20050086786A/ko not_active Application Discontinuation
- 2003-11-25 JP JP2004555635A patent/JP4489597B2/ja not_active Expired - Fee Related
- 2003-11-25 EA EA200500878A patent/EA009603B1/ru not_active IP Right Cessation
- 2003-11-25 ES ES03783752T patent/ES2388277T3/es not_active Expired - Lifetime
- 2003-11-25 SI SI200332179T patent/SI1569892T1/sl unknown
- 2003-11-25 CA CA2507226A patent/CA2507226C/en not_active Expired - Fee Related
- 2003-11-25 EP EP03783752A patent/EP1569892B1/en not_active Expired - Lifetime
- 2003-11-25 KR KR1020117025893A patent/KR101142697B1/ko not_active IP Right Cessation
- 2003-11-25 PT PT03783752T patent/PT1569892E/pt unknown
- 2003-11-25 WO PCT/US2003/037461 patent/WO2004047751A2/en active Application Filing
- 2003-11-25 AU AU2003291157A patent/AU2003291157C1/en not_active Ceased
- 2003-11-25 CN CNB2003801092068A patent/CN1325466C/zh not_active Expired - Fee Related
- 2003-11-25 NZ NZ540275A patent/NZ540275A/en not_active IP Right Cessation
- 2003-11-25 PE PE2003001196A patent/PE20040845A1/es not_active Application Discontinuation
- 2003-11-25 MX MXPA05005574A patent/MXPA05005574A/es active IP Right Grant
- 2003-11-25 AP AP2005003320A patent/AP2113A/xx active
- 2003-11-25 US US10/536,416 patent/US7514473B2/en not_active Expired - Fee Related
-
2005
- 2005-05-19 IL IL168704A patent/IL168704A/en not_active IP Right Cessation
- 2005-05-23 MA MA28294A patent/MA27528A1/fr unknown
- 2005-05-24 CO CO05050416A patent/CO5570664A2/es active IP Right Grant
- 2005-06-02 IS IS7880A patent/IS2897B/is unknown
- 2005-06-22 NO NO20053071A patent/NO332304B1/no not_active IP Right Cessation
-
2006
- 2006-02-07 ZA ZA200504104A patent/ZA200504104B/en unknown
- 2006-03-02 HK HK06102773.3A patent/HK1082914A1/xx not_active IP Right Cessation
-
2009
- 2009-02-26 US US12/393,284 patent/US7829594B2/en not_active Expired - Fee Related
-
2010
- 2010-09-30 US US12/894,644 patent/US8399517B2/en not_active Expired - Fee Related
-
2012
- 2012-09-03 CY CY20121100784T patent/CY1113083T1/el unknown
-
2013
- 2013-02-11 US US13/764,126 patent/US8586631B2/en not_active Expired - Fee Related
- 2013-11-01 US US14/069,447 patent/US8980950B2/en not_active Expired - Fee Related
-
2015
- 2015-03-06 US US14/640,711 patent/US9227914B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200504104B (en) | Calcilytic compounds | |
RU2319698C2 (ru) | АЛЬФА-ФЕНИЛ ИЛИ ПИРИДИЛ-ЭТАНОЛАМИНЫ И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ АГОНИСТОВ β3 АДРЕНЕРГИЧЕСКИХ РЕЦЕПТОРОВ | |
US20080234370A1 (en) | Calcilytic Compounds | |
AU764746B2 (en) | Calcilytic compounds | |
US4515814A (en) | 3-Phenoxypropan-2-ol derivatives for treating glaucoma | |
US20040192741A1 (en) | Calcilytic compounds | |
TWI268919B (en) | Ethers of O-desmethyl venlafaxine | |
JPH11286483A (ja) | クロマン誘導体およびこれを有効成分とするngf産生誘導剤 | |
HU190453B (en) | Process for preparing new 1-alkyl-amino-3-/4-/p-alkoxy-benzoyl-amino/-phenoxy/-2-propanol derivatives and salts thereof | |
CZ220392A3 (en) | Substituted 1-phenyl-1-benzoylamino-5-aminopentanes, their preparation and use |