JP2016519167A5 - - Google Patents
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- JP2016519167A5 JP2016519167A5 JP2016515609A JP2016515609A JP2016519167A5 JP 2016519167 A5 JP2016519167 A5 JP 2016519167A5 JP 2016515609 A JP2016515609 A JP 2016515609A JP 2016515609 A JP2016515609 A JP 2016515609A JP 2016519167 A5 JP2016519167 A5 JP 2016519167A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- alkyl
- halo
- phenyl
- 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
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- -1 phosphoryl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000005843 halogen group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 10
- 125000003277 amino group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000002252 acyl group Chemical group 0.000 claims 8
- 230000005856 abnormality Effects 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000003435 aroyl group Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 239000007924 injection Substances 0.000 claims 5
- 238000002347 injection Methods 0.000 claims 5
- 229910052805 deuterium Inorganic materials 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000003147 glycosyl group Chemical group 0.000 claims 4
- 230000003287 optical effect Effects 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 239000000843 powder Substances 0.000 claims 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- 102000003903 Cyclin-dependent kinases Human genes 0.000 claims 2
- 108090000266 Cyclin-dependent kinases Proteins 0.000 claims 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims 2
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims 2
- 101000617830 Homo sapiens Sterol O-acyltransferase 1 Proteins 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 102100021993 Sterol O-acyltransferase 1 Human genes 0.000 claims 2
- 101000697584 Streptomyces lavendulae Streptothricin acetyltransferase Proteins 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 125000000089 arabinosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)CO1)* 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000004153 glucose metabolism Effects 0.000 claims 2
- 208000018914 glucose metabolism disease Diseases 0.000 claims 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 2
- 229940093915 gynecological organic acid Drugs 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 235000005985 organic acids Nutrition 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- 230000019491 signal transduction Effects 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 claims 2
- 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 1
- 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 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NBGQZFQREPIKMG-UHFFFAOYSA-N 3beta-hydroxy-beta-boswellic acid Natural products C1CC(O)C(C)(C(O)=O)C2CCC3(C)C4(C)CCC5(C)CCC(C)C(C)C5C4=CCC3C21C NBGQZFQREPIKMG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 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 1
- NBGQZFQREPIKMG-PONOSELZSA-N Boswellic acid Chemical compound C1C[C@@H](O)[C@](C)(C(O)=O)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C NBGQZFQREPIKMG-PONOSELZSA-N 0.000 claims 1
- 229940126074 CDK kinase inhibitor Drugs 0.000 claims 1
- 108091007914 CDKs Proteins 0.000 claims 1
- BQENDLAVTKRQMS-SBBGFIFASA-L Carbenoxolone sodium Chemical compound [Na+].[Na+].C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C([O-])=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](OC(=O)CCC([O-])=O)C1(C)C BQENDLAVTKRQMS-SBBGFIFASA-L 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 102100034770 Cyclin-dependent kinase inhibitor 3 Human genes 0.000 claims 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 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 1
- 229940123856 Glycogen synthase kinase 3 inhibitor Drugs 0.000 claims 1
- MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 claims 1
- 101000945639 Homo sapiens Cyclin-dependent kinase inhibitor 3 Proteins 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
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- 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 1
- 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 1
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- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
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- 235000011054 acetic acid Nutrition 0.000 claims 1
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- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
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- 229960005070 ascorbic acid Drugs 0.000 claims 1
- JXSVIVRDWWRQRT-UYDOISQJSA-N asiatic acid Chemical compound C1[C@@H](O)[C@H](O)[C@@](C)(CO)[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 JXSVIVRDWWRQRT-UYDOISQJSA-N 0.000 claims 1
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- LBGFKBYMNRAMFC-PYSQTNCISA-N asiatic acid Natural products C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@@]34C)[C@]2(C)[C@H]1C)C(=O)O LBGFKBYMNRAMFC-PYSQTNCISA-N 0.000 claims 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
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- 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 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
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- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
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| PCT/CN2014/000525 WO2014190758A1 (zh) | 2013-05-28 | 2014-05-26 | 苯并呋喃酮与吲哚或氮杂吲哚偶合物及其制备与应用 |
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| CN103333161B (zh) * | 2013-05-28 | 2015-09-30 | 滁州市洛达生物科技有限公司 | 1’-氧代靛玉红的制备和用途 |
| CN108721279B (zh) * | 2017-04-19 | 2021-06-29 | 安尼根有限公司 | 包含5′-羟基-5-硝基-靛玉红-3′-肟作为活性成分的乳腺癌治疗剂 |
| CN106946760A (zh) * | 2017-04-28 | 2017-07-14 | 遵义医学院 | 靛玉红衍生物或药学上能接受的盐用于抗肿瘤药物及制备方法 |
| CN111233741B (zh) * | 2020-03-04 | 2021-04-16 | 大连理工大学 | 一种有机催化靛红自缩合制备异靛蓝类化合物的方法 |
| WO2021188855A1 (en) * | 2020-03-19 | 2021-09-23 | Board Of Regents Of The University Of Nebraska | Symbiotic prodrugs for the treatment of cancer and other diseases |
| WO2022171265A1 (en) * | 2021-02-09 | 2022-08-18 | Boehringer Ingelheim International Gmbh | Modulators of complex i |
| CN113072540B (zh) * | 2021-03-29 | 2023-07-14 | 贵州医科大学 | 一种靛玉红衍生的降解剂及其制备与应用 |
| WO2023090935A1 (ko) * | 2021-11-18 | 2023-05-25 | 애니젠 주식회사 | 뉴클레오린에 특이적으로 결합하는 agm 펩타이드를 제조하는 방법 |
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| JPS609022B2 (ja) * | 1981-06-19 | 1985-03-07 | イスクラ産業株式会社 | インジルビン誘導体およびそれを含有する抗腫瘍剤 |
| JPS617254A (ja) * | 1984-06-20 | 1986-01-13 | Isukura Sangyo Kk | ビスインドリノンおよびそれを主成分とする制癌剤 |
| CA2333661A1 (en) * | 1998-05-29 | 1999-12-09 | Cnrs (Centre National De Recherche Scientifique) France Innovation Scien Tifique Et Transfernt | Use of indigoid bisindole derivatives for the manufacture of a medicament to inhibit cyclin dependent kinases |
| US6503937B1 (en) * | 1998-10-22 | 2003-01-07 | Ciba Specialty Chemicals Corporation | Oxobenzofuranylide-dihydroindolone |
| JP2002541244A (ja) * | 1999-04-12 | 2002-12-03 | ゲルハルト アイゼンブランド | インジゴイドビスインドール誘導体 |
| WO2000061124A2 (en) * | 1999-04-12 | 2000-10-19 | Gerhard Eisenbrand | Use off cell membrane penetrating indigoid bisindole derivatives |
| DE10053474A1 (de) * | 2000-10-24 | 2002-05-02 | Schering Ag | Schwefelhaltige Indirubinderivate, deren Herstellung und Verwendung |
| DE10061162A1 (de) * | 2000-11-30 | 2002-07-11 | Schering Ag | Aryl-substituierte Indirubinderivate, deren Herstellung und Verwendung |
| DE10125763A1 (de) * | 2001-05-17 | 2002-11-28 | Schering Ag | Verwendung selektiver Indirubinderivate als VEGF-R Inhibitoren |
| DE10129028A1 (de) * | 2001-06-11 | 2003-01-02 | Schering Ag | Lösliche Cdk-inhibitorische Indirubinderivate |
| US20050154046A1 (en) * | 2004-01-12 | 2005-07-14 | Longgui Wang | Methods of treating an inflammatory-related disease |
| US20100098702A1 (en) * | 2008-09-16 | 2010-04-22 | Longgui Wang | Method of treating androgen independent prostate cancer |
| CA2469649C (en) * | 2001-12-13 | 2011-05-03 | Natrogen Therapeutics, Inc. | Derivatives of isoindigo, indigo and indirubin and use in treating cancer |
| CN1199946C (zh) * | 2002-10-29 | 2005-05-04 | 无锡杰西医药科技有限公司 | 一种特异性吲哚类化合物及制备方法与其在治疗和预防癌症等疾病中的应用 |
| KR100588803B1 (ko) * | 2004-01-27 | 2006-06-12 | 학교법인조선대학교 | 암세포주에 항암활성을 지닌 인디루빈 유도체 |
| US8552053B2 (en) * | 2005-12-23 | 2013-10-08 | Centre National De La Recherche Scientifique | 7-substituted indirubin-3′oximes and their applications |
| CN101023944A (zh) * | 2006-02-23 | 2007-08-29 | 黎明涛 | 靛玉红衍生物在制备治疗神经退行性变疾病药物中的应用 |
| CN101314584A (zh) * | 2007-05-28 | 2008-12-03 | 中国人民解放军军事医学科学院放射与辐射医学研究所 | HGF/c-Met信号通道抑制剂及其制备方法和用途 |
| CN101074229B (zh) | 2007-06-08 | 2010-09-01 | 无锡杰西医药科技有限公司 | 7-氮杂靛玉红和7-氮杂异靛蓝衍生物制备及其药学用途 |
| EP2199292A1 (en) * | 2008-12-22 | 2010-06-23 | Technische Universität Kaiserlautern | 7-azaindirubins, 7'-azaindirubins, 7-7'-diazaindirubin and the corresponding 3'-oxime ether derivates: production thereof, their production and use as a medicament |
| EP2379549B1 (en) * | 2008-12-22 | 2016-09-21 | Eisenbrand, Gerhard | 7-azaindirubins, 7'-azaindirubins, 7-7'-diazaindirubin and the corresponding 3'-oxime ether derivates: production thereof, their production and use as a medicament |
| CN101492465A (zh) * | 2009-03-05 | 2009-07-29 | 上海交通大学 | 用于抗肿瘤药物的7，7＇-二氮杂靛玉红类化合物 |
| CN101492448B (zh) * | 2009-03-05 | 2012-09-19 | 上海交通大学 | 用于抗肿瘤药物的7＇-氮杂靛玉红类化合物 |
| CN101492410B (zh) * | 2009-03-05 | 2011-06-22 | 上海交通大学 | 用于抗肿瘤药物的靛玉红类化合物 |
| CN101704813B (zh) * | 2009-11-25 | 2011-11-16 | 上海交通大学 | 1′-硫代靛玉红类化合物、用途及其制备方法 |
| CN101747339B (zh) * | 2009-11-25 | 2012-04-25 | 上海交通大学 | 1′-硫代氮杂靛玉红类化合物、用途及其制备方法 |
| KR101180030B1 (ko) * | 2010-02-05 | 2012-09-05 | 광주과학기술원 | 사이클린-의존적 키나제 저해제로서 항암 활성을 지닌 인디루빈-3'-옥심 유도체 |
| US9051306B2 (en) * | 2011-07-15 | 2015-06-09 | Nihon University | Indirubin derivative having highly selective cytotoxicity for malignant tumors |
| CN103333161B (zh) * | 2013-05-28 | 2015-09-30 | 滁州市洛达生物科技有限公司 | 1’-氧代靛玉红的制备和用途 |
| CN103627748B (zh) * | 2013-11-21 | 2016-03-30 | 华侨大学 | 一种靛玉红衍生物的制备方法 |
-
2013
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2014
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- 2014-05-26 US US14/779,719 patent/US9868734B2/en not_active Expired - Fee Related
- 2014-05-26 AU AU2014273751A patent/AU2014273751A1/en not_active Abandoned
- 2014-05-26 MX MX2015016217A patent/MX2015016217A/es unknown
- 2014-05-26 KR KR1020157026851A patent/KR20160012984A/ko not_active Withdrawn
- 2014-05-26 EP EP14803761.7A patent/EP3006442A4/en not_active Withdrawn
- 2014-05-26 WO PCT/CN2014/000525 patent/WO2014190758A1/zh not_active Ceased
- 2014-05-26 CN CN201480016601.XA patent/CN105189486B/zh not_active Expired - Fee Related
- 2014-05-26 CA CA2912943A patent/CA2912943A1/en not_active Abandoned
- 2014-05-26 RU RU2015140611A patent/RU2015140611A/ru unknown
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