JP7440934B2 - Abcc11阻害剤 - Google Patents
Abcc11阻害剤 Download PDFInfo
- Publication number
- JP7440934B2 JP7440934B2 JP2021540992A JP2021540992A JP7440934B2 JP 7440934 B2 JP7440934 B2 JP 7440934B2 JP 2021540992 A JP2021540992 A JP 2021540992A JP 2021540992 A JP2021540992 A JP 2021540992A JP 7440934 B2 JP7440934 B2 JP 7440934B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- abcc11
- inhibitor
- carbon atoms
- branched alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 102100037129 ATP-binding cassette sub-family C member 11 Human genes 0.000 title claims description 97
- 101001029057 Homo sapiens ATP-binding cassette sub-family C member 11 Proteins 0.000 title claims description 97
- 239000003112 inhibitor Substances 0.000 title claims description 66
- 229960005101 febuxostat Drugs 0.000 claims description 44
- BQSJTQLCZDPROO-UHFFFAOYSA-N febuxostat Chemical compound C1=C(C#N)C(OCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)S1 BQSJTQLCZDPROO-UHFFFAOYSA-N 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 43
- 210000000170 cell membrane Anatomy 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 229960003838 lesinurad Drugs 0.000 claims description 13
- FGQFOYHRJSUHMR-UHFFFAOYSA-N lesinurad Chemical compound OC(=O)CSC1=NN=C(Br)N1C(C1=CC=CC=C11)=CC=C1C1CC1 FGQFOYHRJSUHMR-UHFFFAOYSA-N 0.000 claims description 13
- 239000002537 cosmetic Substances 0.000 claims description 12
- 230000001404 mediated effect Effects 0.000 claims description 12
- 238000000338 in vitro Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229960002529 benzbromarone Drugs 0.000 claims description 8
- WHQCHUCQKNIQEC-UHFFFAOYSA-N benzbromarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(Br)=C(O)C(Br)=C1 WHQCHUCQKNIQEC-UHFFFAOYSA-N 0.000 claims description 8
- HXNFUBHNUDHIGC-UHFFFAOYSA-N oxypurinol Chemical compound O=C1NC(=O)N=C2NNC=C21 HXNFUBHNUDHIGC-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 239000002781 deodorant agent Substances 0.000 claims description 5
- 239000006210 lotion Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 230000001166 anti-perspirative effect Effects 0.000 claims description 4
- 239000003213 antiperspirant Substances 0.000 claims description 4
- 239000000499 gel Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000002674 ointment Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims 1
- 230000032258 transport Effects 0.000 description 57
- 229950009829 prasterone sulfate Drugs 0.000 description 43
- 230000000694 effects Effects 0.000 description 40
- CZWCKYRVOZZJNM-UHFFFAOYSA-N Prasterone sodium sulfate Natural products C1C(OS(O)(=O)=O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 CZWCKYRVOZZJNM-UHFFFAOYSA-N 0.000 description 39
- CZWCKYRVOZZJNM-USOAJAOKSA-N dehydroepiandrosterone sulfate Chemical compound C1[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 CZWCKYRVOZZJNM-USOAJAOKSA-N 0.000 description 39
- 101000956263 Homo sapiens Uncharacterized protein C19orf48 Proteins 0.000 description 30
- 102100038573 Uncharacterized protein C19orf48 Human genes 0.000 description 30
- 230000001419 dependent effect Effects 0.000 description 23
- 101000986629 Homo sapiens ATP-binding cassette sub-family C member 4 Proteins 0.000 description 18
- 102100028161 ATP-binding cassette sub-family C member 2 Human genes 0.000 description 17
- 102100028163 ATP-binding cassette sub-family C member 4 Human genes 0.000 description 17
- 108010066419 Multidrug Resistance-Associated Protein 2 Proteins 0.000 description 17
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 16
- 201000001431 Hyperuricemia Diseases 0.000 description 14
- 235000019645 odor Nutrition 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- 229940121649 protein inhibitor Drugs 0.000 description 12
- 239000012268 protein inhibitor Substances 0.000 description 12
- 230000002401 inhibitory effect Effects 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 11
- 229940079593 drug Drugs 0.000 description 10
- 239000000758 substrate Substances 0.000 description 9
- 239000002246 antineoplastic agent Substances 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 102100028186 ATP-binding cassette sub-family C member 5 Human genes 0.000 description 7
- 101000986622 Homo sapiens ATP-binding cassette sub-family C member 5 Proteins 0.000 description 7
- 229940041181 antineoplastic drug Drugs 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 7
- 229960003081 probenecid Drugs 0.000 description 7
- 102100037131 ATP-binding cassette sub-family C member 12 Human genes 0.000 description 6
- 101001029062 Homo sapiens ATP-binding cassette sub-family C member 12 Proteins 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 6
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 6
- 229960003459 allopurinol Drugs 0.000 description 6
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 6
- 150000001413 amino acids Chemical group 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 6
- 229960005309 estradiol Drugs 0.000 description 6
- 229930182833 estradiol Natural products 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 230000028327 secretion Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 229940116269 uric acid Drugs 0.000 description 6
- 208000035985 Body Odor Diseases 0.000 description 5
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 229960002949 fluorouracil Drugs 0.000 description 5
- 108010078791 Carrier Proteins Proteins 0.000 description 4
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 4
- DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 description 4
- 206010040904 Skin odour abnormal Diseases 0.000 description 4
- 210000000040 apocrine gland Anatomy 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 229960000485 methotrexate Drugs 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000001356 surgical procedure Methods 0.000 description 4
- 241000701161 unidentified adenovirus Species 0.000 description 4
- 102000005416 ATP-Binding Cassette Transporters Human genes 0.000 description 3
- 108010006533 ATP-Binding Cassette Transporters Proteins 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 102000004855 Multi drug resistance-associated proteins Human genes 0.000 description 3
- 108090001099 Multi drug resistance-associated proteins Proteins 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 210000001099 axilla Anatomy 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- JKKFKPJIXZFSSB-UHFFFAOYSA-N 1,3,5(10)-estratrien-17-one 3-sulfate Natural products OS(=O)(=O)OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 JKKFKPJIXZFSSB-UHFFFAOYSA-N 0.000 description 2
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 101150110927 ABCC11 gene Proteins 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000000846 Bartlett's test Methods 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 102000004420 Creatine Kinase Human genes 0.000 description 2
- 108010042126 Creatine kinase Proteins 0.000 description 2
- 206010059866 Drug resistance Diseases 0.000 description 2
- 238000001061 Dunnett's test Methods 0.000 description 2
- 108010024636 Glutathione Proteins 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 101100131294 Homo sapiens ABCC2 gene Proteins 0.000 description 2
- GWNVDXQDILPJIG-SHSCPDMUSA-N Leukotriene C4 Natural products CCCCCC=C/CC=C/C=C/C=C/C(SCC(NC(=O)CCC(N)C(=O)O)C(=O)NCC(=O)O)C(O)CCCC(=O)O GWNVDXQDILPJIG-SHSCPDMUSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FXEUKVKGTKDDIQ-UWVGGRQHSA-N S-(2,4-dinitrophenyl)glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@H](C(=O)NCC(O)=O)CSC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O FXEUKVKGTKDDIQ-UWVGGRQHSA-N 0.000 description 2
- 108700002781 S-(2,4-dinitrophenyl)glutathione Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006180 TBST buffer Substances 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- SUPKOOSCJHTBAH-UHFFFAOYSA-N adefovir Chemical compound NC1=NC=NC2=C1N=CN2CCOCP(O)(O)=O SUPKOOSCJHTBAH-UHFFFAOYSA-N 0.000 description 2
- WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000001548 androgenic effect Effects 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 239000003833 bile salt Substances 0.000 description 2
- 229940093761 bile salts Drugs 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 108010048367 enhanced green fluorescent protein Proteins 0.000 description 2
- JKKFKPJIXZFSSB-CBZIJGRNSA-M estrone 3-sulfate(1-) Chemical compound [O-]S(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JKKFKPJIXZFSSB-CBZIJGRNSA-M 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 229960003180 glutathione Drugs 0.000 description 2
- 238000003119 immunoblot Methods 0.000 description 2
- 229940027941 immunoglobulin g Drugs 0.000 description 2
- GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000036457 multidrug resistance Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 102200104243 rs17822931 Human genes 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 235000020183 skimmed milk Nutrition 0.000 description 2
- 210000003491 skin Anatomy 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 101150036119 ABCC5 gene Proteins 0.000 description 1
- 102100037128 ATP-binding cassette sub-family C member 10 Human genes 0.000 description 1
- 102100028162 ATP-binding cassette sub-family C member 3 Human genes 0.000 description 1
- 102100028187 ATP-binding cassette sub-family C member 6 Human genes 0.000 description 1
- 101150092939 Abcc4 gene Proteins 0.000 description 1
- 238000009020 BCA Protein Assay Kit Methods 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000283074 Equus asinus Species 0.000 description 1
- 238000001134 F-test Methods 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 101001029059 Homo sapiens ATP-binding cassette sub-family C member 10 Proteins 0.000 description 1
- 101000986633 Homo sapiens ATP-binding cassette sub-family C member 3 Proteins 0.000 description 1
- 101000986621 Homo sapiens ATP-binding cassette sub-family C member 6 Proteins 0.000 description 1
- 101000969812 Homo sapiens Multidrug resistance-associated protein 1 Proteins 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102100021339 Multidrug resistance-associated protein 1 Human genes 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 108091008109 Pseudogenes Proteins 0.000 description 1
- 102000057361 Pseudogenes Human genes 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 108010093894 Xanthine oxidase Proteins 0.000 description 1
- 102100033220 Xanthine oxidase Human genes 0.000 description 1
- 101150067199 abcC12 gene Proteins 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 208000026816 acute arthritis Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 238000012742 biochemical analysis Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013861 fat-free Nutrition 0.000 description 1
- -1 febuxostat Chemical class 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- 210000003780 hair follicle Anatomy 0.000 description 1
- 102000044501 human ABCC4 Human genes 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 230000002601 intratumoral effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229960002847 prasterone Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000004063 proteosomal degradation Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 239000003656 tris buffered saline Substances 0.000 description 1
- 238000012762 unpaired Student’s t-test Methods 0.000 description 1
- 230000028973 vesicle-mediated transport Effects 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Images
Classifications
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/92—Oral administration
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962890053P | 2019-08-21 | 2019-08-21 | |
| US62/890,053 | 2019-08-21 | ||
| PCT/JP2020/031672 WO2021033773A1 (ja) | 2019-08-21 | 2020-08-21 | Abcc11阻害剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPWO2021033773A1 JPWO2021033773A1 (https=) | 2021-02-25 |
| JP7440934B2 true JP7440934B2 (ja) | 2024-02-29 |
Family
ID=74659662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021540992A Active JP7440934B2 (ja) | 2019-08-21 | 2020-08-21 | Abcc11阻害剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20220288038A1 (https=) |
| EP (1) | EP4019048A4 (https=) |
| JP (1) | JP7440934B2 (https=) |
| CN (1) | CN114341120A (https=) |
| WO (1) | WO2021033773A1 (https=) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007148835A1 (ja) | 2006-06-22 | 2007-12-27 | Nippon Chemiphar Co., Ltd. | 抗ガン剤耐性克服剤 |
| WO2018023126A1 (en) | 2016-07-29 | 2018-02-01 | Kaspar Roger L | Methods of treating osmidrosis |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2092580T3 (es) | 1990-11-30 | 1996-12-01 | Teijin Ltd | Derivado de 2-ariltiazol y composicion farmaceutica que contiene el mismo. |
| EP1206937B1 (en) * | 1999-07-16 | 2008-01-23 | Shoei Co., Ltd. | Nitroimidazole external preparations for the treatment of atopic dermatitis |
| DE10352511A1 (de) * | 2003-11-07 | 2005-06-16 | Ernst-Moritz-Arndt-Universität Greifswald | Verwendung von MRP4-Inhibitoren zur Behandlung und/oder Prophylaxe kardiovaskulärer Erkrankungen |
| WO2007018687A1 (en) * | 2005-07-21 | 2007-02-15 | University Of Florida Research Foundation, Inc. | Compositions and methods for treatment and prevention of hyperuricemia related health consequences |
| CN102093309B (zh) * | 2006-12-07 | 2012-07-04 | 重庆医药工业研究院有限责任公司 | 非布司他的晶型及其制备方法 |
| DE102008001811A1 (de) * | 2008-05-15 | 2009-11-19 | Beiersdorf Ag | Kosmetische Zubereitungen zur Verminderung von Schweißgeruch mit ABCC-Modulatoren |
| EP2582683B1 (en) * | 2010-06-15 | 2018-03-21 | Ardea Biosciences, Inc. | Treatment of gout and hyperuricemia |
| WO2012122532A2 (en) * | 2011-03-09 | 2012-09-13 | Biocryst Pharmaceuticals, Inc. | Compositions and methods for treatment of hyperuricemia |
| CN105399694B (zh) * | 2015-12-11 | 2017-09-15 | 浙江京新药业股份有限公司 | 药物Lesinurad轴手性对映体 |
| CN105949156A (zh) * | 2016-05-15 | 2016-09-21 | 刘雨 | 一种伊曲康唑的药物组合物及其医药用途 |
-
2020
- 2020-08-21 US US17/636,151 patent/US20220288038A1/en not_active Abandoned
- 2020-08-21 CN CN202080058788.5A patent/CN114341120A/zh active Pending
- 2020-08-21 JP JP2021540992A patent/JP7440934B2/ja active Active
- 2020-08-21 EP EP20854802.4A patent/EP4019048A4/en not_active Withdrawn
- 2020-08-21 WO PCT/JP2020/031672 patent/WO2021033773A1/ja not_active Ceased
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007148835A1 (ja) | 2006-06-22 | 2007-12-27 | Nippon Chemiphar Co., Ltd. | 抗ガン剤耐性克服剤 |
| WO2018023126A1 (en) | 2016-07-29 | 2018-02-01 | Kaspar Roger L | Methods of treating osmidrosis |
Non-Patent Citations (4)
| Title |
|---|
| EL-SHEIKH, AAK, et al.,Effect of hypouricaemic and hyperuricaemic drugs on the renal urate efflux transporter, multidrug re,British Journal of Pharmacology,2008年08月25日,Vol. 155,p. 1066-1075 |
| KEPPLER, Dietrich,Multidrug Resistance Proteins (MRPs, ABCCs): Importance for Pathophysiology and Drug Therapy,Handbook of Experimental Pharmacology,2010年10月26日,Vol. 201,p. 299-323 |
| SHEN, Zancong, et al.,In Vitro and In Vivo Interaction Studies Between Lesinurad, a Selective Urate Reabsorption Inhibitor,Clin. Drug Investig.,2016年03月07日,Vol. 36,p. 443-452 |
| Zhe-Sheng CHEN et al.,"Transport of Bile Acids, Sulfated Steroids, Estradiol 17-β-d-Glucuronide, and Leukotriene C4 by Human Multidrug Resistance Protein 8 (ABCC11)",Molecular Pharmacology,2004年11月10日,Vol. 67, No. 2,p.545-557,DOI: 10.1124/mol.104.007138 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2021033773A1 (https=) | 2021-02-25 |
| US20220288038A1 (en) | 2022-09-15 |
| EP4019048A4 (en) | 2023-10-04 |
| CN114341120A (zh) | 2022-04-12 |
| WO2021033773A1 (ja) | 2021-02-25 |
| EP4019048A1 (en) | 2022-06-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Olesen et al. | Aquaporin 2 regulation: implications for water balance and polycystic kidney diseases | |
| Birudaraj et al. | Buccal permeation of buspirone: mechanistic studies on transport pathways | |
| Guitart et al. | Biased G protein-independent signaling of dopamine D1-D3 receptor heteromers in the nucleus accumbens | |
| Lin et al. | Mevastatin blockade of autolysosome maturation stimulates LBH589-induced cell death in triple-negative breast cancer cells | |
| Morgan et al. | A role for Cav1. 3 in rat intestinal calcium absorption | |
| US20150010614A1 (en) | Methods and use of inducing apoptosis in cancer cells | |
| JP2020121997A (ja) | 皮膚反応を治療するためのbraf阻害剤の使用 | |
| JP2016523960A (ja) | 限局性強皮症の膏薬療法 | |
| US8431617B2 (en) | Use of resveratrol for the preparation of a medicament useful for the treatment of influenza virus infections | |
| JP5832302B2 (ja) | ケラチンへの局所薬剤デリバリーにおける表面活性タンパク質の組成物、使用及び使用方法 | |
| JP2008536865A (ja) | 抗egfr療法に二次的な皮疹の予防および処置のためのビタミンk | |
| JP7440934B2 (ja) | Abcc11阻害剤 | |
| Pinheiro et al. | Expression and pharmacological inhibition of TrkB and EGFR in glioblastoma | |
| KR102444113B1 (ko) | 안정한 글루코코르티코이드 제제 | |
| AU2023343607A1 (en) | Methods of using a small molecule chemical compound to reduce the appearance of rhytids and wrinkles | |
| US20040116350A1 (en) | Methods and compositions relating to hydrogen peroxide and superoxide production by antibodies | |
| US11583509B2 (en) | Compound for treating cancer and diabetes | |
| US12508260B2 (en) | Combination treatments | |
| US20080132568A1 (en) | Compounds with anti-androgenic activity and the use thereof | |
| US9801848B2 (en) | Prevention of rosacea inflammation | |
| Lu et al. | Pregnancy impacts entecavir pharmacokinetics but does not alter its renal excretion | |
| Van Rensburg et al. | α-Tocopherol antagonizes the multidrug-resistance-reversal activity of cyclosporin A, verapamil, GF120918, clofazimine and B669 | |
| US6706691B1 (en) | Immunosupportive drug sparing diet | |
| JP2007145745A (ja) | 変異型EGFR下流シグナルを抑制するSrcファミリーチロシンキナーゼ阻害剤を含む肺癌治療剤およびその利用 | |
| Serafino et al. | Synergistic antiproliferative and differentiating effect of 2, 4-monofurfurylidene-tetra-O-methylsorbitol and 4, 6-dimethyl-2-(3, 4, 5-trimethoxyphenylamino) pyrimidine on primary and immortalized keratinocytes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20220208 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230404 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230602 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230822 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20231017 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20240116 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20240208 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 7440934 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |