JP2013545729A5 - - Google Patents
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- JP2013545729A5 JP2013545729A5 JP2013535214A JP2013535214A JP2013545729A5 JP 2013545729 A5 JP2013545729 A5 JP 2013545729A5 JP 2013535214 A JP2013535214 A JP 2013535214A JP 2013535214 A JP2013535214 A JP 2013535214A JP 2013545729 A5 JP2013545729 A5 JP 2013545729A5
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- JP
- Japan
- Prior art keywords
- compound
- pharmaceutical composition
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- dysfunction
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 13
- 206010016654 Fibrosis Diseases 0.000 claims description 9
- 230000004761 fibrosis Effects 0.000 claims description 8
- 210000003734 kidney Anatomy 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 208000017169 kidney disease Diseases 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 3
- 208000019838 Blood disease Diseases 0.000 claims 2
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims 2
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 claims 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000014951 hematologic disease Diseases 0.000 claims 2
- 208000018706 hematopoietic system disease Diseases 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 230000004768 organ dysfunction Effects 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 206010071155 Autoimmune arthritis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010014664 Endocardial fibrosis Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 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 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 201000002481 Myositis Diseases 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 208000033464 Reiter syndrome Diseases 0.000 claims 1
- 206010062237 Renal impairment Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 1
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- 239000002246 antineoplastic agent Substances 0.000 claims 1
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- 239000010836 blood and blood product Substances 0.000 claims 1
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- 229910052791 calcium Inorganic materials 0.000 claims 1
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- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 229940109239 creatinine Drugs 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 230000010437 erythropoiesis Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims 1
- 230000005977 kidney dysfunction Effects 0.000 claims 1
- 230000003907 kidney function Effects 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 230000005976 liver dysfunction Effects 0.000 claims 1
- 230000005980 lung dysfunction Effects 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 230000001607 nephroprotective effect Effects 0.000 claims 1
- 208000004235 neutropenia Diseases 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
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- 229910052708 sodium Inorganic materials 0.000 claims 1
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- 229940116269 uric acid Drugs 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 241000700159 Rattus Species 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960004679 doxorubicin Drugs 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 102100031168 CCN family member 2 Human genes 0.000 description 3
- 101000777550 Homo sapiens CCN family member 2 Proteins 0.000 description 3
- 101001066129 Homo sapiens Glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000692 Student's t-test Methods 0.000 description 3
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- 108090001012 Transforming Growth Factor beta Proteins 0.000 description 3
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- 238000003633 gene expression assay Methods 0.000 description 3
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- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 3
- XUDCMQBOWOLYCF-UHFFFAOYSA-N 2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)CC2=C1 XUDCMQBOWOLYCF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 102100021943 C-C motif chemokine 2 Human genes 0.000 description 2
- 101710155857 C-C motif chemokine 2 Proteins 0.000 description 2
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 2
- 102000014158 Interleukin-12 Subunit p40 Human genes 0.000 description 2
- 108010011429 Interleukin-12 Subunit p40 Proteins 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 210000002798 bone marrow cell Anatomy 0.000 description 2
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229960004397 cyclophosphamide Drugs 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000009795 derivation Methods 0.000 description 2
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000010172 mouse model Methods 0.000 description 2
- 230000003589 nefrotoxic effect Effects 0.000 description 2
- 231100000381 nephrotoxic Toxicity 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- GPSYEIQMLURUMM-UHFFFAOYSA-N 3-octanoylbenzoic acid Chemical compound CCCCCCCC(=O)C1=CC=CC(C(O)=O)=C1 GPSYEIQMLURUMM-UHFFFAOYSA-N 0.000 description 1
- JOIPQZKGYUBRSR-UHFFFAOYSA-N 5-octanoyl-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound CCCCCCCC(=O)C1=CC=C2CC(C(O)=O)CC2=C1 JOIPQZKGYUBRSR-UHFFFAOYSA-N 0.000 description 1
- 102000000905 Cadherin Human genes 0.000 description 1
- 108050007957 Cadherin Proteins 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 101000984015 Homo sapiens Cadherin-1 Proteins 0.000 description 1
- 238000000636 Northern blotting Methods 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 208000004608 Ureteral Obstruction Diseases 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229960003624 creatine Drugs 0.000 description 1
- 239000006046 creatine Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- BWGYNDFMGAWDHP-UHFFFAOYSA-N ethyl 2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=CC=C2CC(C(=O)OCC)CC2=C1 BWGYNDFMGAWDHP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000001434 glomerular Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000019734 interleukin-12 production Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- GRYDGXUVWLGHPL-UHFFFAOYSA-M magnesium;heptane;bromide Chemical compound [Mg+2].[Br-].CCCCCC[CH2-] GRYDGXUVWLGHPL-UHFFFAOYSA-M 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- WPVVTAWPRPQICY-UHFFFAOYSA-N methyl 3-(1-hydroxyoctyl)benzoate Chemical compound CCCCCCCC(O)C1=CC=CC(C(=O)OC)=C1 WPVVTAWPRPQICY-UHFFFAOYSA-N 0.000 description 1
- UVSBCUAQEZINCQ-UHFFFAOYSA-N methyl 3-formylbenzoate Chemical compound COC(=O)C1=CC=CC(C=O)=C1 UVSBCUAQEZINCQ-UHFFFAOYSA-N 0.000 description 1
- RIUOQYKCNCKIOI-UHFFFAOYSA-N methyl 3-octanoylbenzoate Chemical compound CCCCCCCC(=O)C1=CC=CC(C(=O)OC)=C1 RIUOQYKCNCKIOI-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 201000001474 proteinuria Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 231100001028 renal lesion Toxicity 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RCDRMMBMVZWZIM-UHFFFAOYSA-M sodium;3-octanoylbenzoate Chemical compound [Na+].CCCCCCCC(=O)C1=CC=CC(C([O-])=O)=C1 RCDRMMBMVZWZIM-UHFFFAOYSA-M 0.000 description 1
- MJZZWEMOZZGWDU-UHFFFAOYSA-M sodium;5-octanoyl-2,3-dihydro-1h-indene-2-carboxylate Chemical compound [Na+].CCCCCCCC(=O)C1=CC=C2CC(C([O-])=O)CC2=C1 MJZZWEMOZZGWDU-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40706810P | 2010-10-27 | 2010-10-27 | |
| US61/407,068 | 2010-10-27 | ||
| PCT/CA2011/001176 WO2012055014A1 (en) | 2010-10-27 | 2011-10-26 | Phenylketone carboxylate compounds and pharmaceutical uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016180777A Division JP2016210814A (ja) | 2010-10-27 | 2016-09-15 | カルボン酸フェニルケトン化合物およびその薬学的使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013545729A JP2013545729A (ja) | 2013-12-26 |
| JP2013545729A5 true JP2013545729A5 (https=) | 2014-12-11 |
| JP6055771B2 JP6055771B2 (ja) | 2016-12-27 |
Family
ID=45992998
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013535214A Expired - Fee Related JP6055771B2 (ja) | 2010-10-27 | 2011-10-26 | カルボン酸フェニルケトン化合物およびその薬学的使用 |
| JP2016180777A Withdrawn JP2016210814A (ja) | 2010-10-27 | 2016-09-15 | カルボン酸フェニルケトン化合物およびその薬学的使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016180777A Withdrawn JP2016210814A (ja) | 2010-10-27 | 2016-09-15 | カルボン酸フェニルケトン化合物およびその薬学的使用 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US9475750B2 (https=) |
| EP (1) | EP2632885B1 (https=) |
| JP (2) | JP6055771B2 (https=) |
| KR (1) | KR101870468B1 (https=) |
| CN (1) | CN103298777B (https=) |
| AU (1) | AU2011320057B2 (https=) |
| BR (1) | BR112013010508B8 (https=) |
| CA (1) | CA2816084C (https=) |
| CL (1) | CL2013001153A1 (https=) |
| DK (1) | DK2632885T3 (https=) |
| EA (1) | EA022988B9 (https=) |
| ES (1) | ES2664816T3 (https=) |
| IL (1) | IL225600A0 (https=) |
| MX (1) | MX348253B (https=) |
| MY (1) | MY164375A (https=) |
| NZ (1) | NZ610853A (https=) |
| PH (1) | PH12013500763B1 (https=) |
| PT (1) | PT2632885T (https=) |
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| WO (1) | WO2012055014A1 (https=) |
| ZA (1) | ZA201303032B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016027283A2 (en) * | 2014-08-22 | 2016-02-25 | Reddy G Pratap | A process for preparing indacaterol and salts thereof |
| DK3204000T3 (da) | 2014-10-10 | 2020-04-06 | Liminal Biosciences Ltd | Phenylketoncarboxylatforbindelser og farmaceutiske sammensætninger til forebyggelse og behandling af osteoporose |
| ES2785317T3 (es) * | 2014-10-10 | 2020-10-06 | Liminal Biosciences Ltd | Compuestos aromáticos sustituidos y composiciones farmacéuticas para la prevención y el tratamiento de la osteoporosis |
| KR20170072352A (ko) | 2014-11-12 | 2017-06-26 | 프로메틱 파마 에스엠티 리미티드 | 조직 자가-회복 및 재생을 위한 치환된 방향족 화합물 및 약제학적 조성물 |
| CN112457188B (zh) * | 2020-11-24 | 2022-07-08 | 苏州博萃循环科技有限公司 | 一种羧酸类化合物及其制备方法与应用 |
| CN116173056B (zh) * | 2021-11-26 | 2025-03-25 | 兰州大学 | 核苷类化合物在制备具有防醉、解酒功效的药物中的应用 |
Family Cites Families (14)
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| US3251064A (en) * | 1962-11-13 | 1966-05-10 | Everett M Schultz | beta-aminoacylphenoxy-and beta-aminoacylphenylmercapto-derivatives of monocarboxylicacids |
| GB1415295A (en) | 1971-10-14 | 1975-11-26 | Orchimed Sa | Substituted phenoxy-alkyl-carboxylic acids and derivatives thereof |
| US3907792A (en) * | 1969-01-31 | 1975-09-23 | Andre Mieville | Phenoxy-alkyl-carboxylic acid derivatives and the preparation thereof |
| JPS4918237B2 (https=) * | 1971-10-12 | 1974-05-08 | ||
| US3870752A (en) * | 1973-08-31 | 1975-03-11 | Sandoz Ag | Acyl substituted indane carboxylic acids |
| JPS56100739A (en) * | 1980-01-16 | 1981-08-12 | Yamanouchi Pharmaceut Co Ltd | Substituted phenoxyalkanoic acid derivative and its preparation |
| US5928912A (en) * | 1991-12-24 | 1999-07-27 | Basf Aktiengesellschaft | Process for the hydroxylation of aromatic acids using strains of the fungus Beauveria |
| ES2050072B1 (es) * | 1992-07-28 | 1994-12-16 | Menarini Lab | "procedimiento para obtener acidos meta- y para-acilbenzoicos" |
| IT1270846B (it) | 1993-05-10 | 1997-05-13 | Alfa Wassermann Spa | Uso di sulodexide e delle specialita' medicinali che lo contengono nel trattamento della nefropatia diabetica. |
| US6830751B1 (en) | 1994-03-14 | 2004-12-14 | Genetics Institute, Llc | Use of IL-12 antagonists in the treatment of rheumatoid arthritis |
| US7030146B2 (en) | 1996-09-10 | 2006-04-18 | University Of South Carolina | Methods for treating diabetic neuropathy |
| US6693097B2 (en) | 2001-11-30 | 2004-02-17 | Synta Pharmaceuticals Corp. | Pyrimidine compounds |
| CN1243541C (zh) * | 2002-05-09 | 2006-03-01 | 中国医学科学院药物研究所 | 2－(α－羟基戊基)苯甲酸盐及其制法和用途 |
| CN100422133C (zh) * | 2003-09-01 | 2008-10-01 | 北京天衡药物研究院 | 2-（α-羟基戊基）苯甲酸盐及其制法和用途 |
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