BRPI0710180A2 - derivados de benzimidazol - Google Patents
derivados de benzimidazol Download PDFInfo
- Publication number
- BRPI0710180A2 BRPI0710180A2 BRPI0710180-5A BRPI0710180A BRPI0710180A2 BR PI0710180 A2 BRPI0710180 A2 BR PI0710180A2 BR PI0710180 A BRPI0710180 A BR PI0710180A BR PI0710180 A2 BRPI0710180 A2 BR PI0710180A2
- Authority
- BR
- Brazil
- Prior art keywords
- methoxy
- formula
- compound
- ethyl
- isopropyl
- Prior art date
Links
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- 229940002612 prodrug Drugs 0.000 claims abstract description 9
- 239000000651 prodrug Substances 0.000 claims abstract description 9
- -1 amino, carboxy Chemical group 0.000 claims description 34
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 18
- 108090000445 Parathyroid hormone Proteins 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 16
- 239000011575 calcium Substances 0.000 claims description 16
- 229910052791 calcium Inorganic materials 0.000 claims description 16
- 102000003982 Parathyroid hormone Human genes 0.000 claims description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 15
- 239000000199 parathyroid hormone Substances 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229960001319 parathyroid hormone Drugs 0.000 claims description 13
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 150000002825 nitriles Chemical class 0.000 claims description 11
- 230000011164 ossification Effects 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
- 208000020084 Bone disease Diseases 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
- 230000000638 stimulation Effects 0.000 claims description 8
- 206010006956 Calcium deficiency Diseases 0.000 claims description 7
- 210000000988 bone and bone Anatomy 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 239000012634 fragment Substances 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 102100036893 Parathyroid hormone Human genes 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 229940122361 Bisphosphonate Drugs 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 229930003316 Vitamin D Natural products 0.000 claims description 3
- 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 3
- 239000013543 active substance Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 150000004663 bisphosphonates Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 239000003270 steroid hormone Substances 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 235000019166 vitamin D Nutrition 0.000 claims description 3
- 239000011710 vitamin D Substances 0.000 claims description 3
- 150000003710 vitamin D derivatives Chemical class 0.000 claims description 3
- 229940046008 vitamin d Drugs 0.000 claims description 3
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- 229940122156 Cathepsin K inhibitor Drugs 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 102000015694 estrogen receptors Human genes 0.000 claims description 2
- 108010038795 estrogen receptors Proteins 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 239000012038 nucleophile Substances 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- YZRCEDKJCYMCGB-UHFFFAOYSA-N 2-[3-[[7-methoxy-1-(2-methoxyethyl)-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazol-5-yl]methyl]pyridin-2-yl]oxy-n,n-dimethylethanamine Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1OCCN(C)C YZRCEDKJCYMCGB-UHFFFAOYSA-N 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 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 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 59
- 229910001868 water Inorganic materials 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 235000019439 ethyl acetate Nutrition 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000001514 detection method Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 239000012267 brine Substances 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 238000002560 therapeutic procedure Methods 0.000 description 8
- XNEWILNREVDHDJ-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfonylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1S(C)(=O)=O XNEWILNREVDHDJ-UHFFFAOYSA-N 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000003643 water by type Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- XJIQNOQRLZSHST-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfanylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1SC XJIQNOQRLZSHST-UHFFFAOYSA-N 0.000 description 4
- 108060001064 Calcitonin Proteins 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QCOLDAACMNYDIP-UHFFFAOYSA-N 1-(trifluoromethyl)benzimidazole Chemical compound C1=CC=C2N(C(F)(F)F)C=NC2=C1 QCOLDAACMNYDIP-UHFFFAOYSA-N 0.000 description 3
- UZRUCGBRGXJVHQ-UHFFFAOYSA-N 3-bromo-2-methylsulfanylpyridine Chemical compound CSC1=NC=CC=C1Br UZRUCGBRGXJVHQ-UHFFFAOYSA-N 0.000 description 3
- 102000055006 Calcitonin Human genes 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 208000001132 Osteoporosis Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000003302 alkenyloxy group Chemical group 0.000 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 description 3
- 229960004015 calcitonin Drugs 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229940095743 selective estrogen receptor modulator Drugs 0.000 description 3
- 239000000333 selective estrogen receptor modulator Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- UTKCWZWWIQFORB-UHFFFAOYSA-N (2-methylsulfanylpyridin-3-yl)methanol Chemical compound CSC1=NC=CC=C1CO UTKCWZWWIQFORB-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- HNXCBYBLDPXLMN-UHFFFAOYSA-N 4-bromo-7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfanylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(Br)C=1CC1=CC=CN=C1SC HNXCBYBLDPXLMN-UHFFFAOYSA-N 0.000 description 2
- NIQSGWJDOXIURI-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-5-[(2-methoxypyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1OC NIQSGWJDOXIURI-UHFFFAOYSA-N 0.000 description 2
- STKOFLRHQQCLDD-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfinylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1S(C)=O STKOFLRHQQCLDD-UHFFFAOYSA-N 0.000 description 2
- MFUFZKHPBQXMBL-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-5-[(2-propan-2-yloxypyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1OC(C)C MFUFZKHPBQXMBL-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- INAPMGSXUVUWAF-GCVPSNMTSA-N [(2r,3s,5r,6r)-2,3,4,5,6-pentahydroxycyclohexyl] dihydrogen phosphate Chemical compound OC1[C@H](O)[C@@H](O)C(OP(O)(O)=O)[C@H](O)[C@@H]1O INAPMGSXUVUWAF-GCVPSNMTSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000001195 anabolic effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229960000817 bazedoxifene Drugs 0.000 description 2
- UCJGJABZCDBEDK-UHFFFAOYSA-N bazedoxifene Chemical compound C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 UCJGJABZCDBEDK-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 208000037765 diseases and disorders Diseases 0.000 description 2
- 210000002950 fibroblast Anatomy 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229960000367 inositol Drugs 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 2
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 2
- 229910000367 silver sulfate Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- WZDGZWOAQTVYBX-XOINTXKNSA-N tibolone Chemical compound C([C@@H]12)C[C@]3(C)[C@@](C#C)(O)CC[C@H]3[C@@H]1[C@H](C)CC1=C2CCC(=O)C1 WZDGZWOAQTVYBX-XOINTXKNSA-N 0.000 description 2
- 239000011345 viscous material Substances 0.000 description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- HDYNIWBNWMFBDO-UHFFFAOYSA-N 3-bromo-2-chloropyridine Chemical compound ClC1=NC=CC=C1Br HDYNIWBNWMFBDO-UHFFFAOYSA-N 0.000 description 1
- PORGLLGXCAQORO-UHFFFAOYSA-N 3-bromo-2-methoxypyridine Chemical compound COC1=NC=CC=C1Br PORGLLGXCAQORO-UHFFFAOYSA-N 0.000 description 1
- ZJKMBBWISFOMSY-UHFFFAOYSA-N 4-bromo-7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfinylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(Br)C=1CC1=CC=CN=C1S(C)=O ZJKMBBWISFOMSY-UHFFFAOYSA-N 0.000 description 1
- GRBVSNFJJZRAQP-UHFFFAOYSA-N 4-iodo-7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfinylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(I)C=1CC1=CC=CN=C1S(C)=O GRBVSNFJJZRAQP-UHFFFAOYSA-N 0.000 description 1
- MXMSONJMVWOEPO-UHFFFAOYSA-N 5-[(2-ethoxypyridin-3-yl)methyl]-7-methoxy-1-(2-methoxyethyl)-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound CCOC1=NC=CC=C1CC1=CC(OC)=C(N(CCOC)C(=N2)C=3C=CC(=CC=3)C(C)C)C2=C1C(F)(F)F MXMSONJMVWOEPO-UHFFFAOYSA-N 0.000 description 1
- WOFFMODEYRHQGY-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-2-(4-propan-2-ylphenyl)-5-[(2-prop-2-ynoxypyridin-3-yl)methyl]-4-(trifluoromethyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=C(C(F)(F)F)C=1CC1=CC=CN=C1OCC#C WOFFMODEYRHQGY-UHFFFAOYSA-N 0.000 description 1
- JLTPTSWOAQALBQ-UHFFFAOYSA-N 7-methoxy-1-(2-methoxyethyl)-5-[(2-methylsulfanylpyridin-3-yl)methyl]-2-(4-propan-2-ylphenyl)benzimidazole Chemical compound C=1C(OC)=C2N(CCOC)C(C=3C=CC(=CC=3)C(C)C)=NC2=CC=1CC1=CC=CN=C1SC JLTPTSWOAQALBQ-UHFFFAOYSA-N 0.000 description 1
- GXMQKRXNPGPMHC-UHFFFAOYSA-N 7-methoxy-5-[[2-(2-methoxyethoxy)pyridin-3-yl]methyl]-1-(2-methoxyethyl)-2-(4-propan-2-ylphenyl)-4-(trifluoromethyl)benzimidazole Chemical compound COCCOC1=NC=CC=C1CC1=CC(OC)=C(N(CCOC)C(=N2)C=3C=CC(=CC=3)C(C)C)C2=C1C(F)(F)F GXMQKRXNPGPMHC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 208000002679 Alveolar Bone Loss Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 208000006386 Bone Resorption Diseases 0.000 description 1
- 206010065687 Bone loss Diseases 0.000 description 1
- 229940078581 Bone resorption inhibitor Drugs 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 102000013830 Calcium-Sensing Receptors Human genes 0.000 description 1
- 108010050543 Calcium-Sensing Receptors Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 102000004171 Cathepsin K Human genes 0.000 description 1
- 108090000625 Cathepsin K Proteins 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010049119 Emotional distress Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 101000741445 Homo sapiens Calcitonin Proteins 0.000 description 1
- 101001135770 Homo sapiens Parathyroid hormone Proteins 0.000 description 1
- 101001135995 Homo sapiens Probable peptidyl-tRNA hydrolase Proteins 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000000038 Hypoparathyroidism Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- MPBVHIBUJCELCL-UHFFFAOYSA-N Ibandronate Chemical compound CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O MPBVHIBUJCELCL-UHFFFAOYSA-N 0.000 description 1
- 101710144867 Inositol monophosphatase Proteins 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 208000030886 Traumatic Brain injury Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- AMJRSUWJSRKGNO-UHFFFAOYSA-N acetyloxymethyl 2-[n-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]-5-(2,7-dichloro-3-hydroxy-6-oxoxanthen-9-yl)phenoxy]ethoxy]-4-methylanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC=C(C)C=C1OCCOC1=CC(C2=C3C=C(Cl)C(=O)C=C3OC3=CC(O)=C(Cl)C=C32)=CC=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O AMJRSUWJSRKGNO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000005571 anion exchange chromatography Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 229950005529 arzoxifene Drugs 0.000 description 1
- MCGDSOGUHLTADD-UHFFFAOYSA-N arzoxifene Chemical compound C1=CC(OC)=CC=C1C1=C(OC=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 MCGDSOGUHLTADD-UHFFFAOYSA-N 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229950001536 balicatib Drugs 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 150000005347 biaryls Chemical group 0.000 description 1
- 230000024279 bone resorption Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000001727 carbonic acid monoesters Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 208000037887 cell injury Diseases 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000005115 demineralization Methods 0.000 description 1
- 230000002328 demineralizing effect Effects 0.000 description 1
- 229960001251 denosumab Drugs 0.000 description 1
- 230000009429 distress Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 238000002825 functional assay Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 229940045644 human calcitonin Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 229940015872 ibandronate Drugs 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 102000006029 inositol monophosphatase Human genes 0.000 description 1
- 230000008991 intestinal motility Effects 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-M methanethiolate Chemical compound [S-]C LSDPWZHWYPCBBB-UHFFFAOYSA-M 0.000 description 1
- GQJCAQADCPTHKN-UHFFFAOYSA-N methyl 2,2-difluoro-2-fluorosulfonylacetate Chemical compound COC(=O)C(F)(F)S(F)(=O)=O GQJCAQADCPTHKN-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- LLCRBOWRJOUJAE-UHFFFAOYSA-N n-[1-(cyanomethylcarbamoyl)cyclohexyl]-4-(4-propylpiperazin-1-yl)benzamide Chemical compound C1CN(CCC)CCN1C1=CC=C(C(=O)NC2(CCCCC2)C(=O)NCC#N)C=C1 LLCRBOWRJOUJAE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 208000005368 osteomalacia Diseases 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 230000000849 parathyroid Effects 0.000 description 1
- 108010073509 parathyroid hormone (1-31) Proteins 0.000 description 1
- 108010073230 parathyroid hormone (1-38) Proteins 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229960004622 raloxifene Drugs 0.000 description 1
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 108010068072 salmon calcitonin Proteins 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000012679 serum free medium Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- OGBMKVWORPGQRR-UMXFMPSGSA-N teriparatide Chemical compound C([C@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H](N)CO)C(C)C)[C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)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](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CNC=N1 OGBMKVWORPGQRR-UMXFMPSGSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 229960001023 tibolone Drugs 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 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
- 230000009529 traumatic brain injury Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
- 229960004276 zoledronic acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A61P25/10—Antiepileptics; Anticonvulsants for petit-mal
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A61P25/12—Antiepileptics; Anticonvulsants for grand-mal
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0606426.5 | 2006-03-30 | ||
| GBGB0606426.5A GB0606426D0 (en) | 2006-03-30 | 2006-03-30 | Benzimidazole derivatives |
| PCT/EP2007/002763 WO2007112913A2 (en) | 2006-03-30 | 2007-03-28 | Benzimidazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0710180A2 true BRPI0710180A2 (pt) | 2011-08-09 |
Family
ID=36424926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0710180-5A BRPI0710180A2 (pt) | 2006-03-30 | 2007-03-28 | derivados de benzimidazol |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US20100227889A1 (enExample) |
| EP (1) | EP2004629A2 (enExample) |
| JP (1) | JP2009531363A (enExample) |
| KR (1) | KR20080110769A (enExample) |
| CN (1) | CN101400669A (enExample) |
| AR (1) | AR060334A1 (enExample) |
| AU (1) | AU2007234021B2 (enExample) |
| BR (1) | BRPI0710180A2 (enExample) |
| CA (1) | CA2644380A1 (enExample) |
| CL (1) | CL2007000850A1 (enExample) |
| CR (1) | CR10199A (enExample) |
| EC (1) | ECSP088781A (enExample) |
| GB (1) | GB0606426D0 (enExample) |
| GT (1) | GT200800200A (enExample) |
| IL (1) | IL193475A0 (enExample) |
| MA (1) | MA30341B1 (enExample) |
| MX (1) | MX2008012403A (enExample) |
| NO (1) | NO20084543L (enExample) |
| PE (1) | PE20071149A1 (enExample) |
| RU (1) | RU2008142831A (enExample) |
| TN (1) | TNSN08369A1 (enExample) |
| TW (1) | TW200806647A (enExample) |
| WO (1) | WO2007112913A2 (enExample) |
| ZA (1) | ZA200806833B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2904546T3 (es) | 2006-02-03 | 2022-04-05 | Opko Renal Llc | Tratamiento de la insuficiencia y deficiencia de vitamina D con 25-hidroxivitamina D2 y 25-hidroxivitamina D3 |
| SI2037936T1 (sl) | 2006-06-21 | 2014-11-28 | Opko Renal, Llc | Postopek zdravljenja in prepreäśevanja sekundarnega hiperparatiroidizma |
| PT2148661E (pt) | 2007-04-25 | 2013-03-06 | Proventiv Therapeutics Llc | Composições orais de libertação controlada compreendendo um composto de vitamina d e veículo ceroso |
| CA2683628C (en) | 2007-04-25 | 2018-03-06 | Cytochroma Inc. | Method of treating vitamin d insufficiency and deficiency |
| CN105796530A (zh) | 2010-03-29 | 2016-07-27 | 赛特克罗公司 | 用于降低甲状旁腺水平的方法和组合物 |
| CN103228629A (zh) * | 2010-11-26 | 2013-07-31 | 利奥制药有限公司 | 作为CaSR活性化合物的被取代的环戊基-氮杂苯类 |
| KR101847947B1 (ko) | 2013-03-15 | 2018-05-28 | 옵코 아이피 홀딩스 Ⅱ 인코포레이티드 | 안정화되고 변형된 비타민 ｄ 방출 제형 |
| US10220047B2 (en) | 2014-08-07 | 2019-03-05 | Opko Ireland Global Holdings, Ltd. | Adjunctive therapy with 25-hydroxyvitamin D and articles therefor |
| UA129792C2 (uk) | 2016-03-28 | 2025-08-06 | Ейрджен Фарма Лтд. | Способи лікування вітаміном d |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000026430A (ja) * | 1998-07-02 | 2000-01-25 | Taisho Pharmaceut Co Ltd | ２、５、６−置換ベンズイミダゾール化合物誘導体 |
| US6362202B1 (en) * | 1999-03-02 | 2002-03-26 | Sepracor Inc. | Methods and compositions using (−) norcisapride in combination with proton pump inhibitors or H2 receptor antagonists |
| WO2004041277A1 (en) * | 2002-11-01 | 2004-05-21 | Merck & Co., Inc. | Carbonylamino-benzimidazole derivatives as androgen receptor modulators |
| GB0400781D0 (en) * | 2004-01-14 | 2004-02-18 | Novartis Ag | Organic compounds |
| EP1964548A1 (en) * | 2007-03-02 | 2008-09-03 | Novartis AG | Pharmaceutical compositions comprising a calcilytic agent |
-
2006
- 2006-03-30 GB GBGB0606426.5A patent/GB0606426D0/en not_active Ceased
-
2007
- 2007-03-28 US US12/295,381 patent/US20100227889A1/en not_active Abandoned
- 2007-03-28 KR KR1020087023787A patent/KR20080110769A/ko not_active Withdrawn
- 2007-03-28 JP JP2009501943A patent/JP2009531363A/ja not_active Withdrawn
- 2007-03-28 MX MX2008012403A patent/MX2008012403A/es not_active Application Discontinuation
- 2007-03-28 AU AU2007234021A patent/AU2007234021B2/en not_active Ceased
- 2007-03-28 AR ARP070101297A patent/AR060334A1/es not_active Application Discontinuation
- 2007-03-28 WO PCT/EP2007/002763 patent/WO2007112913A2/en not_active Ceased
- 2007-03-28 BR BRPI0710180-5A patent/BRPI0710180A2/pt not_active IP Right Cessation
- 2007-03-28 PE PE2007000352A patent/PE20071149A1/es not_active Application Discontinuation
- 2007-03-28 RU RU2008142831/04A patent/RU2008142831A/ru not_active Application Discontinuation
- 2007-03-28 EP EP07723708A patent/EP2004629A2/en not_active Withdrawn
- 2007-03-28 CA CA002644380A patent/CA2644380A1/en not_active Abandoned
- 2007-03-28 CN CNA2007800087520A patent/CN101400669A/zh active Pending
- 2007-03-29 CL CL200700850A patent/CL2007000850A1/es unknown
- 2007-03-29 TW TW096111055A patent/TW200806647A/zh unknown
-
2008
- 2008-08-07 ZA ZA200806833A patent/ZA200806833B/xx unknown
- 2008-08-11 CR CR10199A patent/CR10199A/es not_active Application Discontinuation
- 2008-08-14 IL IL193475A patent/IL193475A0/en unknown
- 2008-09-22 TN TNP2008000369A patent/TNSN08369A1/en unknown
- 2008-09-29 GT GT200800200A patent/GT200800200A/es unknown
- 2008-09-30 EC EC2008008781A patent/ECSP088781A/es unknown
- 2008-10-17 MA MA31302A patent/MA30341B1/fr unknown
- 2008-10-28 NO NO20084543A patent/NO20084543L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ECSP088781A (es) | 2008-10-31 |
| TW200806647A (en) | 2008-02-01 |
| PE20071149A1 (es) | 2007-12-04 |
| JP2009531363A (ja) | 2009-09-03 |
| GT200800200A (es) | 2008-11-10 |
| CN101400669A (zh) | 2009-04-01 |
| AU2007234021A1 (en) | 2007-10-11 |
| WO2007112913A3 (en) | 2007-12-21 |
| WO2007112913A2 (en) | 2007-10-11 |
| RU2008142831A (ru) | 2010-05-10 |
| AR060334A1 (es) | 2008-06-11 |
| CR10199A (es) | 2008-10-16 |
| MA30341B1 (fr) | 2009-04-01 |
| EP2004629A2 (en) | 2008-12-24 |
| US20100227889A1 (en) | 2010-09-09 |
| CL2007000850A1 (es) | 2008-03-14 |
| IL193475A0 (en) | 2009-05-04 |
| AU2007234021B2 (en) | 2011-04-28 |
| KR20080110769A (ko) | 2008-12-19 |
| NO20084543L (no) | 2008-10-21 |
| MX2008012403A (es) | 2008-10-07 |
| TNSN08369A1 (en) | 2009-12-29 |
| ZA200806833B (en) | 2009-05-27 |
| CA2644380A1 (en) | 2007-10-11 |
| GB0606426D0 (en) | 2006-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BRPI0710180A2 (pt) | derivados de benzimidazol | |
| JP6014154B2 (ja) | ベンゼンスルホンアミド化合物および治療剤としてのそれらの使用 | |
| EP3484464B1 (en) | N1-phenylpropane-1,2-diamine compounds with selective activity in voltage-gated sodium channels | |
| EP3725780B1 (en) | Sulfonamide derivative or pharmaceutically acceptable acid-addition salt | |
| JP2010518026A (ja) | ナトリウムチャネルが介在する疾患または状態の治療に有用なピリドピリミジノン化合物 | |
| TW200836743A (en) | Quinazolinone and fused pyrimidinone compounds and their use in treating sodium channel-mediated diseases or conditions | |
| BRPI0614544A2 (pt) | derivados de benzoquinazolina e uso dos mesmos no tratamento de doenças ósseas | |
| JP4571863B2 (ja) | 抗痛覚過敏剤として有用なキナゾリノン誘導体 | |
| JP7357057B2 (ja) | １－メチル－４－［（４－フェニルフェニル）スルホニルメチル］シクロヘキサノール化合物及び１－メチル－４－［［４－（２－ピリジル）フェニル］スルホニルメチル］シクロヘキサノール化合物並びにそれらの治療的使用 | |
| JPWO2012039371A1 (ja) | シクロプロパン化合物 | |
| JP6854823B2 (ja) | ３−（カルボキシメチル）−８−アミノ−２−オキソ−１，３−ジアザ−スピロ−［４．５］−デカン誘導体 | |
| AU2003296710A1 (en) | Derivatives of aryl-quinazoline/aryl-2-amino-phenyl methanone which promote the release of parathyroid hormone | |
| CA2921742A1 (en) | Amide derivatives as lysophosphatidic acid receptor antagonists | |
| CA2566053A1 (en) | Phenyl carboxamide compounds useful as beta-secretase inhibitors for the treatment of alzheimer's disease | |
| US8030497B2 (en) | Benzimidazole derivatives | |
| KR20090074179A (ko) | Ｐｐａｒ 조절제로서 유용한 １ｈ인돌２카르복실산 유도체 | |
| US20100099670A1 (en) | Benzoquinazoline derivatives | |
| TW202241845A (zh) | 經取代的環己烷甲醯胺、其製備方法及其治療用途 | |
| KR20250134083A (ko) | NaV1.8의 저해제로서의 설폭시민 | |
| EP3892614A1 (en) | (1h-indol-5-yl)acrylamide derivatives as inhibitors of tead proteins and the hippo-yap1/taz signaling cascade for the treatment of cancer | |
| HK1196818A (en) | Benzenesulfonamide compounds and their use as therapeutic agents | |
| HK1196818B (en) | Benzenesulfonamide compounds and their use as therapeutic agents | |
| NZ710293B2 (en) | Amides as modulators of sodium channels | |
| NZ710293A (en) | Amides as modulators of sodium channels |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B08F | Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette] |
Free format text: REFERENTE 6A. ANUIDADE(S). |
|
| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: REFERENTE AO DESPACHO 8.6 PUBLICADO NA RPI 2225 DE 27/08/2013. |