JP2018517666A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018517666A5 JP2018517666A5 JP2017552432A JP2017552432A JP2018517666A5 JP 2018517666 A5 JP2018517666 A5 JP 2018517666A5 JP 2017552432 A JP2017552432 A JP 2017552432A JP 2017552432 A JP2017552432 A JP 2017552432A JP 2018517666 A5 JP2018517666 A5 JP 2018517666A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- derivative
- analogue
- moiety derived
- pharmaceutical composition
- 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.)
- Pending
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 66
- 239000008194 pharmaceutical composition Substances 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 46
- 229940093265 berberine Drugs 0.000 claims description 35
- QISXPYZVZJBNDM-UHFFFAOYSA-N berberine Natural products COc1ccc2C=C3N(Cc2c1OC)C=Cc4cc5OCOc5cc34 QISXPYZVZJBNDM-UHFFFAOYSA-N 0.000 claims description 35
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims description 33
- 201000010099 disease Diseases 0.000 claims description 33
- 208000035475 disorder Diseases 0.000 claims description 33
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 claims description 26
- YBHILYKTIRIUTE-UHFFFAOYSA-N berberine Chemical compound C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 YBHILYKTIRIUTE-UHFFFAOYSA-N 0.000 claims description 26
- RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 claims description 26
- 229960001661 ursodiol Drugs 0.000 claims description 26
- 150000007524 organic acids Chemical class 0.000 claims description 19
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 18
- 229960003105 metformin Drugs 0.000 claims description 18
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 17
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 17
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 16
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 16
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 14
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims description 14
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 14
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 14
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 14
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 claims description 12
- FRWNAQDBODEVAL-VMPITWQZSA-N (5e)-5-[(4-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1\C=C\1C(=O)NC(=S)S/1 FRWNAQDBODEVAL-VMPITWQZSA-N 0.000 claims description 12
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 claims description 12
- QNMKGMUGYVWVFQ-UHFFFAOYSA-N 2alpha-Hydroxyursolic acid Natural products CC12CC(O)C(O)C(C)(C)C1CCC1(C)C2CC=C2C3C(C)C(C)(C)CCC3(C(O)=O)CCC21C QNMKGMUGYVWVFQ-UHFFFAOYSA-N 0.000 claims description 12
- ZMJBYMUCKBYSCP-UHFFFAOYSA-N Hydroxycitric acid Chemical compound OC(=O)C(O)C(O)(C(O)=O)CC(O)=O ZMJBYMUCKBYSCP-UHFFFAOYSA-N 0.000 claims description 12
- 229940089491 hydroxycitric acid Drugs 0.000 claims description 12
- 229940096998 ursolic acid Drugs 0.000 claims description 12
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 claims description 12
- AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims description 11
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 9
- 208000002249 Diabetes Complications Diseases 0.000 claims description 9
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 9
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 9
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 9
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 9
- 206010028289 Muscle atrophy Diseases 0.000 claims description 9
- 208000008589 Obesity Diseases 0.000 claims description 9
- 208000001280 Prediabetic State Diseases 0.000 claims description 9
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 9
- 150000003836 berberines Chemical group 0.000 claims description 9
- 239000003613 bile acid Substances 0.000 claims description 9
- 206010012601 diabetes mellitus Diseases 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 230000004054 inflammatory process Effects 0.000 claims description 9
- 230000020763 muscle atrophy Effects 0.000 claims description 9
- 201000000585 muscular atrophy Diseases 0.000 claims description 9
- 235000020824 obesity Nutrition 0.000 claims description 9
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 9
- 206010012655 Diabetic complications Diseases 0.000 claims description 8
- 208000019423 liver disease Diseases 0.000 claims description 8
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 8
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 8
- 229960004889 salicylic acid Drugs 0.000 claims description 8
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims description 7
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims description 7
- XUHLIQGRKRUKPH-UHFFFAOYSA-N (R)C(S)S-Alliin Chemical compound OC(=O)C(N)CS(=O)CC=C XUHLIQGRKRUKPH-UHFFFAOYSA-N 0.000 claims description 7
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 7
- QGJZLNKBHJESQX-UHFFFAOYSA-N 3-Epi-Betulin-Saeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CCC3C21C QGJZLNKBHJESQX-UHFFFAOYSA-N 0.000 claims description 7
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 claims description 7
- CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 claims description 7
- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 claims description 7
- DIZWSDNSTNAYHK-XGWVBXMLSA-N Betulinic acid Natural products CC(=C)[C@@H]1C[C@H]([C@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O DIZWSDNSTNAYHK-XGWVBXMLSA-N 0.000 claims description 7
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 claims description 7
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 claims description 7
- 239000004380 Cholic acid Substances 0.000 claims description 7
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 7
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 claims description 7
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 claims description 7
- RDHQFKQIGNGIED-MRVPVSSYSA-N O-acetyl-L-carnitine Chemical compound CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C RDHQFKQIGNGIED-MRVPVSSYSA-N 0.000 claims description 7
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 claims description 7
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 claims description 7
- FCDLCPWAQCPTKC-UHFFFAOYSA-N Rhein Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC(O)=C3C(=O)C2=C1O FCDLCPWAQCPTKC-UHFFFAOYSA-N 0.000 claims description 7
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 7
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 7
- 229960005070 ascorbic acid Drugs 0.000 claims description 7
- 235000010323 ascorbic acid Nutrition 0.000 claims description 7
- 239000011668 ascorbic acid Substances 0.000 claims description 7
- QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 claims description 7
- 229960002685 biotin Drugs 0.000 claims description 7
- 235000020958 biotin Nutrition 0.000 claims description 7
- 239000011616 biotin Substances 0.000 claims description 7
- 235000004883 caffeic acid Nutrition 0.000 claims description 7
- 229940074360 caffeic acid Drugs 0.000 claims description 7
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 claims description 7
- 235000001368 chlorogenic acid Nutrition 0.000 claims description 7
- 229940074393 chlorogenic acid Drugs 0.000 claims description 7
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 claims description 7
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims description 7
- 229960002471 cholic acid Drugs 0.000 claims description 7
- 235000019416 cholic acid Nutrition 0.000 claims description 7
- 235000013985 cinnamic acid Nutrition 0.000 claims description 7
- 229930016911 cinnamic acid Natural products 0.000 claims description 7
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 claims description 7
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 claims description 7
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims description 7
- PZXJOHSZQAEJFE-UHFFFAOYSA-N dihydrobetulinic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(C)C)C5C4CCC3C21C PZXJOHSZQAEJFE-UHFFFAOYSA-N 0.000 claims description 7
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 7
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 7
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 7
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 7
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 7
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 7
- MQYXUWHLBZFQQO-UHFFFAOYSA-N nepehinol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C MQYXUWHLBZFQQO-UHFFFAOYSA-N 0.000 claims description 7
- 229960003512 nicotinic acid Drugs 0.000 claims description 7
- 235000001968 nicotinic acid Nutrition 0.000 claims description 7
- 239000011664 nicotinic acid Substances 0.000 claims description 7
- 229940100243 oleanolic acid Drugs 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 7
- 229940055726 pantothenic acid Drugs 0.000 claims description 7
- 235000019161 pantothenic acid Nutrition 0.000 claims description 7
- 239000011713 pantothenic acid Substances 0.000 claims description 7
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 claims description 7
- 229930002330 retinoic acid Natural products 0.000 claims description 7
- 229960001727 tretinoin Drugs 0.000 claims description 7
- ZZLHPCSGGOGHFW-ZMQIUWNVSA-N (2s)-2-amino-3-methylsulfinylpropanoic acid Chemical compound CS(=O)C[C@@H](N)C(O)=O ZZLHPCSGGOGHFW-ZMQIUWNVSA-N 0.000 claims description 6
- 208000002231 Muscle Neoplasms Diseases 0.000 claims description 6
- 201000002481 Myositis Diseases 0.000 claims description 6
- 201000002077 muscle cancer Diseases 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 229940093915 gynecological organic acid Drugs 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 206010008635 Cholestasis Diseases 0.000 claims description 4
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 208000024908 graft versus host disease Diseases 0.000 claims description 4
- 210000004185 liver Anatomy 0.000 claims description 4
- QUCQEUCGKKTEBI-UHFFFAOYSA-N palmatine Chemical compound COC1=CC=C2C=C(C3=C(C=C(C(=C3)OC)OC)CC3)[N+]3=CC2=C1OC QUCQEUCGKKTEBI-UHFFFAOYSA-N 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 235000019136 lipoic acid Nutrition 0.000 claims 1
- 229960002663 thioctic acid Drugs 0.000 claims 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- -1 copticin Chemical compound 0.000 description 3
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 2
- SEBFKMXJBCUCAI-UHFFFAOYSA-N NSC 227190 Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC=C(C=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-UHFFFAOYSA-N 0.000 description 2
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 description 2
- MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical compound O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H](N)C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-N 0.000 description 2
- IDIDJDIHTAOVLG-VKHMYHEASA-N S-methylcysteine Chemical compound CSC[C@H](N)C(O)=O IDIDJDIHTAOVLG-VKHMYHEASA-N 0.000 description 2
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 description 2
- 229930003316 Vitamin D Natural products 0.000 description 2
- 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 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- 229960004308 acetylcysteine Drugs 0.000 description 2
- 229960001570 ademetionine Drugs 0.000 description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 2
- 229940012843 omega-3 fatty acid Drugs 0.000 description 2
- 239000006014 omega-3 oil Substances 0.000 description 2
- 229940016667 resveratrol Drugs 0.000 description 2
- 235000021283 resveratrol Nutrition 0.000 description 2
- SEBFKMXJBCUCAI-HKTJVKLFSA-N silibinin Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC=C(C=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-HKTJVKLFSA-N 0.000 description 2
- 229960004245 silymarin Drugs 0.000 description 2
- 235000017700 silymarin Nutrition 0.000 description 2
- 235000019166 vitamin D Nutrition 0.000 description 2
- 239000011710 vitamin D Substances 0.000 description 2
- 150000003710 vitamin D derivatives Chemical class 0.000 description 2
- 235000019165 vitamin E Nutrition 0.000 description 2
- 229940046009 vitamin E Drugs 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- 229940046008 vitamin d Drugs 0.000 description 2
- IDIDJDIHTAOVLG-UHFFFAOYSA-N S-methyl-L-cysteine Natural products CSCC(N)C(O)=O IDIDJDIHTAOVLG-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562143734P | 2015-04-06 | 2015-04-06 | |
| US62/143,734 | 2015-04-06 | ||
| PCT/CN2016/078414 WO2016161921A1 (en) | 2015-04-06 | 2016-04-05 | Conjugate compounds of ursodeoxycholic, berberine or l-carnitine, and compositions and methods thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018517666A JP2018517666A (ja) | 2018-07-05 |
| JP2018517666A5 true JP2018517666A5 (enExample) | 2019-05-16 |
Family
ID=57072197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017552432A Pending JP2018517666A (ja) | 2015-04-06 | 2016-04-05 | ウルソデオキシコール酸、ベルベリンまたはｌ−カルニチンのコンジュゲート化合物、ならびにその組成物および方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US20180050048A1 (enExample) |
| EP (1) | EP3280712A4 (enExample) |
| JP (1) | JP2018517666A (enExample) |
| CN (1) | CN108137575A (enExample) |
| AU (1) | AU2016245590A1 (enExample) |
| CA (1) | CA2981754A1 (enExample) |
| IL (1) | IL254831A0 (enExample) |
| SG (1) | SG11201708030XA (enExample) |
| WO (1) | WO2016161921A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019050850A1 (en) * | 2017-09-05 | 2019-03-14 | Primetime Life Sciences, Llc | BIGUANIDINE DERIVATIVES OF THERAPEUTIC AGENTS, AND PREPARATION METHODS AND METHODS OF USING SAME |
| CN108395429A (zh) * | 2018-01-23 | 2018-08-14 | 北京宜生堂医药科技研究有限公司 | 一种化合物及其制备方法和用途 |
| IL281761B2 (en) | 2018-09-25 | 2025-09-01 | Ponce De Leon Health Designated Activity Company | Process for preparing calcium alpha-ketoglutarate |
| WO2021197333A1 (zh) * | 2020-03-31 | 2021-10-07 | 浙江养生堂天然药物研究所有限公司 | 药物组合及其用途 |
| US20230181547A1 (en) * | 2020-05-15 | 2023-06-15 | Nguyen Anh VAN | Solid lipid nano-composition containing berberine and cinnamonaldehyde effective in treating diabetes, dyslipidemia, and method of preparing the same |
| CN113943312A (zh) * | 2020-07-17 | 2022-01-18 | 轶诺(浙江)药业有限公司 | 一类肠道裂解型共药及其制备和用途 |
| CN114195850B (zh) * | 2020-09-18 | 2024-08-16 | 成都贝诺科成生物科技有限公司 | 一种用于防治肝病的化合物及其制药用途 |
| CN113045689B (zh) * | 2021-03-24 | 2022-03-29 | 齐鲁工业大学 | 一种小檗碱-环糊精缀合物 |
| US20230102471A1 (en) * | 2021-09-29 | 2023-03-30 | Cannogen Biosciences, Inc. | Composition And Method for Modulating Hydrogen Ion Physiology Related to Weight Loss and Metabolism |
| CN114716498B (zh) * | 2022-01-20 | 2024-01-23 | 成都贝诺科成生物科技有限公司 | 一种高稳定性的失碳熊去氧胆酸小檗碱盐晶型及其制备方法 |
| CN114747570B (zh) * | 2022-03-15 | 2023-03-28 | 浙江蓝德能源科技发展有限公司 | 一种超分子盐抑菌液及其制备方法 |
| EP4642454A1 (en) * | 2022-12-30 | 2025-11-05 | Shenzhen Hightide Biopharmaceutical Ltd. | Pharmaceutical combinations and compositions, and methods of use thereof |
| WO2024179570A1 (en) * | 2023-03-01 | 2024-09-06 | Shenzhen Hightide Biopharmaceutical Ltd. | Compositions and methods for treating severe hypertriglyceridemia |
| CN116621904A (zh) * | 2023-05-31 | 2023-08-22 | 中国医学科学院药用植物研究所 | 肉桂酰熊去氧胆酸类化合物及其制法、药物组合物和应用 |
| WO2024245371A1 (zh) * | 2023-05-31 | 2024-12-05 | 上海复宏汉霖生物技术股份有限公司 | 一种组合产品、盐及其用于治疗神经退行性疾病或病症的用途 |
| CN117530876A (zh) * | 2023-11-20 | 2024-02-09 | 浙江睿颜新材料科技有限公司 | 一种超分子异槲皮素制剂及其制备方法 |
| KR20250116419A (ko) * | 2024-01-25 | 2025-08-01 | 주식회사 알트메디칼 | 이소퀴놀린 유도체 화합물을 유효성분으로 포함하는 당뇨병성 신증의 예방 또는 치료용 약학적 조성물 |
| CN118638020B (zh) * | 2024-08-08 | 2024-11-19 | 杭州海尔希畜牧科技有限公司 | L-天门冬氨酸l(-)肉碱(1:1)的制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2350124C2 (ru) * | 2004-01-28 | 2009-03-27 | Нестек С.А. | Питательная композиция для улучшения состояния кожи и предотвращения кожных заболеваний |
| US8318954B2 (en) * | 2006-02-23 | 2012-11-27 | Nou Life Sciences, Inc. | Cleavable carnitine compound |
| CN101113149B (zh) * | 2006-07-25 | 2011-04-27 | 复旦大学 | 小檗碱类生物碱的脂肪族有机酸盐及其制备方法和应用 |
| CN102060809B (zh) * | 2009-05-01 | 2015-05-20 | 常州高新技术产业开发区三维工业技术研究所有限公司 | 一种大黄酸衍生物及其制备和用途 |
| CN101935319A (zh) * | 2010-09-09 | 2011-01-05 | 陕西科技大学 | 一种黄连素有机酸盐和黄连素有机酸盐包合物及其制备方法 |
| CN102225913B (zh) * | 2011-04-07 | 2013-09-04 | 栗进才 | 大黄酸衍生物以及它们的治疗用途 |
| CN102229636A (zh) * | 2011-04-21 | 2011-11-02 | 东北林业大学 | 小檗碱9位酯键偶合胆酸的新衍生物及其制备方法 |
| CN102225962A (zh) * | 2011-04-21 | 2011-10-26 | 东北林业大学 | 小檗碱9位酰胺键合胆酸的新衍生物及制备方法 |
| CN102225961A (zh) * | 2011-04-21 | 2011-10-26 | 东北林业大学 | 小檗碱9位偶合胆酸新衍生物及其制备方法 |
| JP2014513125A (ja) * | 2011-05-02 | 2014-05-29 | バイオキアー・インコーポレイテッド | 糖尿病の治療用組成物および方法 |
| CN103319479B (zh) * | 2012-03-20 | 2015-08-26 | 王从品 | 大黄酸小檗碱离子对化合物、制备方法及应用 |
| CN103989677A (zh) * | 2013-12-20 | 2014-08-20 | 中国药科大学 | 去亚甲基小檗碱在制备降血糖药物中的应用 |
| NZ728488A (en) * | 2014-07-29 | 2023-03-31 | Shenzhen Hightide Biopharmaceutical Ltd | Berberine salts, ursodeoxycholic salts and combinations, methods of preparation and application thereof |
-
2016
- 2016-04-05 US US15/557,199 patent/US20180050048A1/en not_active Abandoned
- 2016-04-05 CN CN201680032575.9A patent/CN108137575A/zh active Pending
- 2016-04-05 CA CA2981754A patent/CA2981754A1/en not_active Abandoned
- 2016-04-05 WO PCT/CN2016/078414 patent/WO2016161921A1/en not_active Ceased
- 2016-04-05 AU AU2016245590A patent/AU2016245590A1/en not_active Abandoned
- 2016-04-05 SG SG11201708030XA patent/SG11201708030XA/en unknown
- 2016-04-05 EP EP16776096.6A patent/EP3280712A4/en not_active Withdrawn
- 2016-04-05 JP JP2017552432A patent/JP2018517666A/ja active Pending
-
2017
- 2017-10-02 IL IL254831A patent/IL254831A0/en unknown
-
2019
- 2019-04-23 US US16/392,385 patent/US20200022992A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018517666A5 (enExample) | ||
| JP2017522264A5 (enExample) | ||
| AU2019222911A1 (en) | Berberine salts, ursodeoxycholic salts and combinations, methods of prepration and application thereof | |
| JP7458443B2 (ja) | スルホラファン及び／又はスルホラファンの誘導体及びオオアザミ抽出物又は粉末を含む組成物 | |
| RU2018133298A (ru) | Способы применения агонистов fxr | |
| JP2020128412A5 (enExample) | ||
| BR112012011784A2 (pt) | "formulações parenterais de derivados de gencitabina". | |
| US20200022992A1 (en) | Conjugate compounds of ursodeoxycholic, berberine or l-carnitine, and compositions and methods thereof | |
| HRP20210686T1 (hr) | Pripravci i postupci za liječenje moždanog udara kod subjekta na istodobnoj terapiji statinom | |
| JP2018514534A5 (enExample) | ||
| JP2020522514A5 (enExample) | ||
| MX2014004948A (es) | Formulaciones orales mimeticas de las acciones de la derivacion gastrica en y de roux en el freno ileal; composiciones, metodos de tratamiento, diagnostico y sistemas para el tratamiento de las manifestaciones del sindrome metabolico, incluyendo resistencia a la isulina, enfermedad de higado graso, hiperlipidemia y diabetes del tipo 2. | |
| JP2019048843A5 (enExample) | ||
| NZ600167A (en) | Concentrated therapeutic phospholipid compositions | |
| CN105120872B (zh) | 包含15-hepe的组合物以及其使用方法 | |
| US6340705B1 (en) | Use of α-linolenic acid metabolites for treatment or prevention of cancer | |
| CA3116858A1 (en) | Novel compositions for the treatment of inflammatory diseases | |
| JP2018507914A5 (enExample) | ||
| JP2004526745A5 (enExample) | ||
| WO2010121128A3 (en) | Compositions and methods for treating or inhibiting liver injury | |
| CA3146071A1 (en) | Preparation comprising omega-3 fatty acid salts and extracts of gum resins from boswellia species | |
| JP2022031813A (ja) | １５－ｈｅｐｅを含む組成物、およびそれを用いて線維症を処置または防止する方法 | |
| AR094374A1 (es) | Composiciones y métodos para el tratamiento de trastornos metabólicos | |
| JP2016511753A5 (enExample) | ||
| EP3846821A1 (en) | Combination therapy for the treatment of liver disease |