AU2003265585B2 - Calcium receptor modulating compound and use thereof - Google Patents
Calcium receptor modulating compound and use thereof Download PDFInfo
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- AU2003265585B2 AU2003265585B2 AU2003265585A AU2003265585A AU2003265585B2 AU 2003265585 B2 AU2003265585 B2 AU 2003265585B2 AU 2003265585 A AU2003265585 A AU 2003265585A AU 2003265585 A AU2003265585 A AU 2003265585A AU 2003265585 B2 AU2003265585 B2 AU 2003265585B2
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- amino
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- 150000001875 compounds Chemical class 0.000 title claims description 263
- 102000013830 Calcium-Sensing Receptors Human genes 0.000 title claims description 13
- 108010050543 Calcium-Sensing Receptors Proteins 0.000 title claims description 13
- -1 amidino, carbamoyl Chemical group 0.000 claims description 465
- LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 claims description 252
- 125000001424 substituent group Chemical group 0.000 claims description 250
- 150000002430 hydrocarbons Chemical group 0.000 claims description 223
- 125000000623 heterocyclic group Chemical group 0.000 claims description 212
- 125000000217 alkyl group Chemical group 0.000 claims description 205
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 160
- 150000003839 salts Chemical class 0.000 claims description 154
- 125000003277 amino group Chemical group 0.000 claims description 148
- 125000003118 aryl group Chemical group 0.000 claims description 142
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 126
- 229920006395 saturated elastomer Polymers 0.000 claims description 104
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 100
- 229910052757 nitrogen Inorganic materials 0.000 claims description 95
- 229910052717 sulfur Inorganic materials 0.000 claims description 89
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 88
- 125000005843 halogen group Chemical group 0.000 claims description 84
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 84
- 125000004434 sulfur atom Chemical group 0.000 claims description 83
- 125000005842 heteroatom Chemical group 0.000 claims description 80
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 77
- 125000003545 alkoxy group Chemical group 0.000 claims description 72
- 125000001931 aliphatic group Chemical group 0.000 claims description 70
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 69
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 65
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 60
- 125000002619 bicyclic group Chemical group 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 53
- 150000002367 halogens Chemical class 0.000 claims description 53
- 125000002723 alicyclic group Chemical group 0.000 claims description 52
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 51
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 51
- 239000011575 calcium Substances 0.000 claims description 51
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 46
- 125000002252 acyl group Chemical group 0.000 claims description 46
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 46
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 43
- 125000003282 alkyl amino group Chemical group 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 41
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 37
- 125000004414 alkyl thio group Chemical group 0.000 claims description 35
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 32
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 28
- 229930195733 hydrocarbon Natural products 0.000 claims description 27
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
- 239000004215 Carbon black (E152) Substances 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 23
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 22
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 22
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 20
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 20
- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 15
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 13
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 12
- 208000020084 Bone disease Diseases 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- 208000001132 Osteoporosis Diseases 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 238000009833 condensation Methods 0.000 claims description 10
- 230000005494 condensation Effects 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000005750 substituted cyclic group Chemical group 0.000 claims description 9
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 7
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 7
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
- 230000027455 binding Effects 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229940123613 Calcium receptor antagonist Drugs 0.000 claims description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 3
- 230000005856 abnormality Effects 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 229940075993 receptor modulator Drugs 0.000 claims description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical group 0.000 claims 4
- UBDSIWCNQHLBBQ-UHFFFAOYSA-N 5-(2-fluorophenyl)-7,7-dimethyl-N-[3-(4-methylphenyl)pentan-3-yl]-5,6-dihydro-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=C(C)C=CC=1C(CC)(CC)NC(=O)C=1C=NN(C(C2)(C)C)C=1NC2C1=CC=CC=C1F UBDSIWCNQHLBBQ-UHFFFAOYSA-N 0.000 claims 1
- CSNWDSWUGSIAQN-UHFFFAOYSA-N 7,7-dimethyl-5,6-dihydro-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1(CCNC=2N1N=CC=2C(=O)N)C CSNWDSWUGSIAQN-UHFFFAOYSA-N 0.000 claims 1
- 101100072620 Streptomyces griseus ind2 gene Proteins 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- HUZMHENQDRSAGB-UHFFFAOYSA-N chembl1687946 Chemical compound C=1C=C(C)C=CC=1C(CC)(CC)NC(=O)C=1C=NN(C(C2)(C)C)C=1NC2C1=CC=CC=C1 HUZMHENQDRSAGB-UHFFFAOYSA-N 0.000 claims 1
- FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 74
- 239000002904 solvent Substances 0.000 description 63
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 59
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
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- 102000005962 receptors Human genes 0.000 description 33
- 108020003175 receptors Proteins 0.000 description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 30
- 125000003944 tolyl group Chemical group 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
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- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 20
- 229910052783 alkali metal Inorganic materials 0.000 description 20
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
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- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 7
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- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
- POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- ATYCFPYEKYTCCV-UHFFFAOYSA-J tetrachlorotitanium titanium Chemical class [Ti].Cl[Ti](Cl)(Cl)Cl ATYCFPYEKYTCCV-UHFFFAOYSA-J 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000008359 toxicosis Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 208000017997 tumor of parathyroid gland Diseases 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- 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
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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
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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
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- 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]
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- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- 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
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Endocrinology (AREA)
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- Hematology (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40601202P | 2002-08-26 | 2002-08-26 | |
| US60/406,012 | 2002-08-26 | ||
| US46612903P | 2003-04-28 | 2003-04-28 | |
| US60/466,129 | 2003-04-28 | ||
| PCT/US2003/026317 WO2004017908A2 (en) | 2002-08-26 | 2003-08-21 | Calcium receptor modulating compound and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003265585A1 AU2003265585A1 (en) | 2004-03-11 |
| AU2003265585B2 true AU2003265585B2 (en) | 2008-07-03 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003265585A Ceased AU2003265585B2 (en) | 2002-08-26 | 2003-08-21 | Calcium receptor modulating compound and use thereof |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US7514441B2 (enExample) |
| EP (1) | EP1572113B1 (enExample) |
| JP (1) | JP4494205B2 (enExample) |
| KR (1) | KR101050700B1 (enExample) |
| AU (1) | AU2003265585B2 (enExample) |
| BR (1) | BRPI0313880B8 (enExample) |
| CA (1) | CA2494700C (enExample) |
| ES (1) | ES2635838T3 (enExample) |
| NO (1) | NO332991B1 (enExample) |
| NZ (1) | NZ538223A (enExample) |
| PL (1) | PL382706A1 (enExample) |
| WO (1) | WO2004017908A2 (enExample) |
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| AU2003265585B2 (en) * | 2002-08-26 | 2008-07-03 | Takeda Pharmaceutical Company Limited | Calcium receptor modulating compound and use thereof |
| US7453002B2 (en) | 2004-06-15 | 2008-11-18 | Bristol-Myers Squibb Company | Five-membered heterocycles useful as serine protease inhibitors |
| US7361789B1 (en) | 2004-07-28 | 2008-04-22 | Amgen Inc. | Dihydronaphthalene compounds, compositions, uses thereof, and methods for synthesis |
| US7790770B2 (en) | 2005-11-23 | 2010-09-07 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| JPWO2007102531A1 (ja) * | 2006-03-08 | 2009-07-23 | 武田薬品工業株式会社 | 併用薬 |
| US8779004B2 (en) | 2006-04-20 | 2014-07-15 | Amgen, Inc. | Stable emulsion formulations |
| EP1975165A1 (de) | 2007-03-27 | 2008-10-01 | Boehringer Ingelheim Pharma GmbH & Co. KG | Substituierte Pyrrolidinamide, deren Herstellung und deren Verwendung als Arzneimittel |
| US8093299B2 (en) | 2007-03-30 | 2012-01-10 | Amgen Inc. | Methods of treating bowel disorders |
| WO2008139947A1 (ja) * | 2007-05-08 | 2008-11-20 | Ajinomoto Co., Inc. | 下痢の予防又は治療剤 |
| EP2197280B1 (en) | 2007-08-27 | 2013-06-19 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| US8586571B2 (en) * | 2007-10-18 | 2013-11-19 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| KR101479371B1 (ko) | 2008-06-05 | 2015-01-05 | 아사히 가세이 파마 가부시키가이샤 | 술폰아미드 화합물 및 그 용도 |
| KR20110010781A (ko) * | 2008-06-16 | 2011-02-07 | 에프. 호프만-라 로슈 아게 | Ｎｋ2 수용체 길항제로서의 피롤리딘 유도체 |
| WO2010034737A1 (en) | 2008-09-24 | 2010-04-01 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| BRPI0919085B1 (pt) | 2008-09-24 | 2021-05-11 | Basf Se | métodos não terapêuticos para controlar pragas invertebradas e para proteger material de propagação de plantas e/ou plantas que se desenvolvem dos mesmos, compostos de pirazol ou um sal ou um n-óxido dos mesmos, e, composição agrícola |
| US8809344B2 (en) | 2008-10-29 | 2014-08-19 | Apath, Llc | Compounds, compositions, and methods for control of hepatitis C viral infections |
| US8318759B2 (en) * | 2009-02-18 | 2012-11-27 | Hoffmann-La Roche Inc. | Pyrrolidine derivatives as NK3 receptor antagonists |
| WO2010104882A1 (en) | 2009-03-10 | 2010-09-16 | Amgen Inc. | Methods of modulating sperm motility |
| EP2451804B1 (en) | 2009-07-06 | 2014-04-30 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
| BR112012000149B8 (pt) | 2009-07-06 | 2021-01-12 | Basf Se | compostos de piridazina, método para controlar pragas invertebradas e método para proteger material de propagação de planta e/ou as plantas |
| US9125414B2 (en) | 2009-07-24 | 2015-09-08 | Basf Se | Pyridine derivatives compounds for controlling invertebrate pests |
| EP2608669B1 (en) | 2010-08-23 | 2016-06-22 | Merck Sharp & Dohme Corp. | NOVEL PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVES AS mTOR INHIBITORS |
| JP2014511894A (ja) * | 2011-04-20 | 2014-05-19 | グラクソ グループ リミテッド | 抗結核化合物としてのテトラヒドロピラゾロ［１，５‐ａ］ピリミジン |
| JO3407B1 (ar) | 2012-05-31 | 2019-10-20 | Eisai R&D Man Co Ltd | مركبات رباعي هيدرو بيرازولو بيريميدين |
| GB201217330D0 (en) | 2012-09-28 | 2012-11-14 | Univ Cardiff | Therapeutic for treating inflammatory lung disorders |
| AU2013344716B2 (en) | 2012-11-16 | 2018-03-01 | University Health Network | Pyrazolopyrimidine compounds |
| EP2970307B1 (en) | 2013-03-13 | 2020-03-11 | Genentech, Inc. | Pyrazolo compounds and uses thereof |
| CN104884458B (zh) | 2013-04-25 | 2017-04-12 | 百济神州有限公司 | 作为蛋白质激酶抑制剂的稠合杂环化合物 |
| TW201602062A (zh) | 2013-08-12 | 2016-01-16 | 魯賓有限公司 | 取代聯苯基化合物作為鈣敏感受體調節劑 |
| SG11201601844TA (en) | 2013-09-13 | 2016-04-28 | Beigene Ltd | Anti-pd1 antibodies and their use as therapeutics and diagnostics |
| CA2941206C (en) | 2014-03-27 | 2022-09-20 | Janssen Pharmaceutica Nv | Substituted 4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidine derivatives and 2,3-dihydro-1h-imidazo[1,2-b]pyrazole derivatives as ros1 inhibitors |
| CA2940918C (en) | 2014-03-27 | 2023-10-24 | Janssen Pharmaceutica Nv | Substituted 4,5,6,7-tetrahydro-pyrazolo[1,5-.alpha.]pyrazine derivatives and 5,6,7,8-tetrahydro-4h-pyrazolo[1,5-.alpha.][1,4]diazepine derivatives as ros1 inhibitors |
| WO2015162538A1 (en) | 2014-04-21 | 2015-10-29 | Lupin Limited | Heterocyclic compounds as calcium sensing receptor modulators for the treatment of hyperparathyroidism, chronic renal failure and chronic kidney disease |
| CN110156892B (zh) | 2014-07-03 | 2023-05-16 | 百济神州有限公司 | 抗pd-l1抗体及其作为治疗剂及诊断剂的用途 |
| WO2017037616A1 (en) | 2015-08-31 | 2017-03-09 | Lupin Limited | Arylalkylamine compounds as calcium sensing receptor modulators |
| EP3156405A1 (en) | 2015-10-13 | 2017-04-19 | Boehringer Ingelheim International GmbH | Spirocyclic ether derivatives of pyrazolo[1,5-a]pyrimidine-3-carboxamide |
| AU2016338679B2 (en) | 2015-10-16 | 2021-05-06 | Eisai R&D Management Co., Ltd. | EP4 antagonists |
| JP6839097B2 (ja) * | 2015-12-25 | 2021-03-03 | 武田薬品工業株式会社 | 医薬 |
| ES2882175T3 (es) * | 2016-03-28 | 2021-12-01 | Takeda Pharmaceuticals Co | Compuestos para su uso en el tratamiento de la hipertensión pulmonar |
| WO2018007885A1 (en) | 2016-07-05 | 2018-01-11 | Beigene, Ltd. | COMBINATION OF A PD-l ANTAGONIST AND A RAF INHIBITOR FOR TREATING CANCER |
| EA201990519A1 (ru) | 2016-08-16 | 2019-08-30 | Бейджин, Лтд. | КРИСТАЛЛИЧЕСКАЯ ФОРМА (S)-7-(1-АКРИЛОИЛПИПЕРИДИН-4-ИЛ)-2-(4-ФЕНОКСИФЕНИЛ)-4,5,6,7-ТЕТРАГИДРОПИРАЗОЛО[1,5-a]ПИРИМИДИН-3-КАРБОКСАМИДА, ЕЕ ПОЛУЧЕНИЕ И ПРИМЕНЕНИЯ |
| AU2017313085B2 (en) | 2016-08-19 | 2024-06-20 | Beone Medicines I Gmbh | Use of a combination comprising a Btk inhibitor for treating cancers |
| CR20190157A (es) | 2016-08-31 | 2019-08-13 | Agios Pharmaceuticals Inc | Inhibidores de procesos metabólicos celulares |
| JOP20190060A1 (ar) | 2016-09-26 | 2019-03-26 | Chugai Pharmaceutical Co Ltd | مشتق بيرازولو بيريدين له تأثير مساعد لمستقبل glp-1 |
| WO2018100070A1 (en) | 2016-12-02 | 2018-06-07 | F. Hoffmann-La Roche Ag | Bicyclic amide compounds and methods of use thereof |
| TWI774726B (zh) | 2017-01-25 | 2022-08-21 | 英屬開曼群島商百濟神州有限公司 | (S)-7-(1-(丁-2-炔醯基)哌啶-4-基)-2-(4-苯氧基苯基)-4,5,6,7-四氫吡唑并[1,5-a]嘧啶-3-甲醯胺的晶型、及其製備和用途 |
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| WO2018199236A1 (ja) * | 2017-04-27 | 2018-11-01 | 武田薬品工業株式会社 | 複素環化合物 |
| TWI877099B (zh) | 2017-06-26 | 2025-03-21 | 英屬開曼群島商百濟神州有限公司 | 抗ｐｄ－１抗體或其抗原結合片段在製備治療用於患有肝細胞癌（ｈｃｃ）之藥物的用途 |
| CN119613408A (zh) | 2017-07-14 | 2025-03-14 | 豪夫迈·罗氏有限公司 | 二环酮化合物及其使用方法 |
| US11377449B2 (en) | 2017-08-12 | 2022-07-05 | Beigene, Ltd. | BTK inhibitors with improved dual selectivity |
| US11072617B2 (en) | 2017-10-31 | 2021-07-27 | Genentech, Inc. | Bicyclic sulfones and sulfoxides and methods of use thereof |
| US11786529B2 (en) | 2017-11-29 | 2023-10-17 | Beigene Switzerland Gmbh | Treatment of indolent or aggressive B-cell lymphomas using a combination comprising BTK inhibitors |
| JP7461104B2 (ja) * | 2017-11-29 | 2024-04-03 | 中外製薬株式会社 | Ｇｌｐ－１受容体アゴニスト作用を持つピラゾロピリジン誘導体を含有する医薬組成物 |
| EP3908586B1 (en) | 2019-01-11 | 2022-12-21 | F. Hoffmann-La Roche AG | Bicyclic pyrrolotriazolr ketone compounds and methods of use thereof |
| EP3981399A4 (en) | 2019-06-10 | 2023-05-31 | BeiGene Switzerland GmbH | ORAL SOLID TABLET WITH A TYROSINE KINAS INHIBITOR AND METHOD OF MANUFACTURE THEREOF |
| US11786531B1 (en) | 2022-06-08 | 2023-10-17 | Beigene Switzerland Gmbh | Methods of treating B-cell proliferative disorder |
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| AU2003265585B2 (en) * | 2002-08-26 | 2008-07-03 | Takeda Pharmaceutical Company Limited | Calcium receptor modulating compound and use thereof |
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2003
- 2003-08-21 AU AU2003265585A patent/AU2003265585B2/en not_active Ceased
- 2003-08-21 WO PCT/US2003/026317 patent/WO2004017908A2/en not_active Ceased
- 2003-08-21 NZ NZ538223A patent/NZ538223A/en not_active IP Right Cessation
- 2003-08-21 CA CA2494700A patent/CA2494700C/en not_active Expired - Lifetime
- 2003-08-21 JP JP2004529835A patent/JP4494205B2/ja not_active Expired - Lifetime
- 2003-08-21 KR KR1020057003335A patent/KR101050700B1/ko not_active Expired - Fee Related
- 2003-08-21 BR BRPI0313880A patent/BRPI0313880B8/pt not_active IP Right Cessation
- 2003-08-21 US US10/525,158 patent/US7514441B2/en not_active Expired - Lifetime
- 2003-08-21 ES ES03793273.8T patent/ES2635838T3/es not_active Expired - Lifetime
- 2003-08-21 PL PL382706A patent/PL382706A1/pl not_active Application Discontinuation
- 2003-08-21 EP EP03793273.8A patent/EP1572113B1/en not_active Expired - Lifetime
-
2005
- 2005-03-15 NO NO20051328A patent/NO332991B1/no not_active IP Right Cessation
-
2008
- 2008-10-31 US US12/263,426 patent/US20090215746A1/en not_active Abandoned
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2013
- 2013-11-25 US US14/089,747 patent/US9447100B2/en not_active Expired - Fee Related
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| WO2001053266A1 (en) * | 2000-01-24 | 2001-07-26 | Kinacia Pty Ltd. | Therapeutic morpholino-substituted compounds |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1572113A2 (en) | 2005-09-14 |
| PL382706A1 (pl) | 2007-11-26 |
| WO2004017908A3 (en) | 2006-01-05 |
| US20090215746A1 (en) | 2009-08-27 |
| US20060079536A1 (en) | 2006-04-13 |
| CA2494700A1 (en) | 2004-03-04 |
| CA2494700C (en) | 2011-06-28 |
| KR101050700B1 (ko) | 2011-07-20 |
| NO20051328L (no) | 2005-03-15 |
| EP1572113A4 (en) | 2006-11-22 |
| BRPI0313880B1 (pt) | 2016-09-27 |
| JP2006510582A (ja) | 2006-03-30 |
| WO2004017908A2 (en) | 2004-03-04 |
| BR0313880A (pt) | 2007-11-06 |
| NZ538223A (en) | 2008-03-28 |
| BRPI0313880B8 (pt) | 2021-05-25 |
| ES2635838T3 (es) | 2017-10-05 |
| US9447100B2 (en) | 2016-09-20 |
| US20140155416A1 (en) | 2014-06-05 |
| NO332991B1 (no) | 2013-02-11 |
| AU2003265585A1 (en) | 2004-03-11 |
| KR20050038641A (ko) | 2005-04-27 |
| US7514441B2 (en) | 2009-04-07 |
| EP1572113B1 (en) | 2017-05-17 |
| JP4494205B2 (ja) | 2010-06-30 |
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