JP2016520622A5 - - Google Patents
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- JP2016520622A5 JP2016520622A5 JP2016517073A JP2016517073A JP2016520622A5 JP 2016520622 A5 JP2016520622 A5 JP 2016520622A5 JP 2016517073 A JP2016517073 A JP 2016517073A JP 2016517073 A JP2016517073 A JP 2016517073A JP 2016520622 A5 JP2016520622 A5 JP 2016520622A5
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- Prior art keywords
- inhibitor
- group
- hexitol derivative
- treatment
- administration
- 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.)
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- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical class OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 claims 156
- 239000003814 drug Substances 0.000 claims 85
- 238000011282 treatment Methods 0.000 claims 83
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- 208000003174 Brain Neoplasms Diseases 0.000 claims 70
- 206010018338 Glioma Diseases 0.000 claims 66
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- 230000000306 recurrent effect Effects 0.000 claims 66
- 239000003112 inhibitor Substances 0.000 claims 57
- 230000000750 progressive effect Effects 0.000 claims 54
- 208000032612 Glial tumor Diseases 0.000 claims 46
- 238000000034 method Methods 0.000 claims 44
- 239000003795 chemical substances by application Substances 0.000 claims 43
- 230000001965 increasing effect Effects 0.000 claims 43
- 229940079593 drug Drugs 0.000 claims 35
- 229940002612 prodrug Drugs 0.000 claims 33
- 239000000651 prodrug Substances 0.000 claims 33
- 230000006872 improvement Effects 0.000 claims 29
- 239000000203 mixture Substances 0.000 claims 27
- 239000008194 pharmaceutical composition Substances 0.000 claims 22
- 229940124597 therapeutic agent Drugs 0.000 claims 15
- 238000002651 drug therapy Methods 0.000 claims 13
- 108090000623 proteins and genes Proteins 0.000 claims 13
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims 12
- 230000014509 gene expression Effects 0.000 claims 12
- 239000000126 substance Substances 0.000 claims 12
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims 11
- 238000002360 preparation method Methods 0.000 claims 11
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- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 10
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- AAFJXZWCNVJTMK-GUCUJZIJSA-N (1s,2r)-1-[(2s)-oxiran-2-yl]-2-[(2r)-oxiran-2-yl]ethane-1,2-diol Chemical compound C([C@@H]1[C@H](O)[C@H](O)[C@H]2OC2)O1 AAFJXZWCNVJTMK-GUCUJZIJSA-N 0.000 claims 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 9
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- DOUMFZQKYFQNTF-WUTVXBCWSA-N (R)-rosmarinic acid Chemical compound C([C@H](C(=O)O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-WUTVXBCWSA-N 0.000 claims 8
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- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 8
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 claims 8
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- 102000004190 Enzymes Human genes 0.000 claims 6
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- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 6
- RADKZDMFGJYCBB-UHFFFAOYSA-N Pyridoxal Chemical compound CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 claims 6
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- 239000011616 biotin Substances 0.000 claims 6
- 229960001948 caffeine Drugs 0.000 claims 6
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims 6
- 229950000758 dianhydrogalactitol Drugs 0.000 claims 6
- 239000003085 diluting agent Substances 0.000 claims 6
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- 230000036457 multidrug resistance Effects 0.000 claims 6
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- 239000012730 sustained-release form Substances 0.000 claims 6
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- 206010065553 Bone marrow failure Diseases 0.000 claims 5
- 102000004877 Insulin Human genes 0.000 claims 5
- 108090001061 Insulin Proteins 0.000 claims 5
- 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 5
- 229940093265 berberine Drugs 0.000 claims 5
- QISXPYZVZJBNDM-UHFFFAOYSA-N berberine Natural products COc1ccc2C=C3N(Cc2c1OC)C=Cc4cc5OCOc5cc34 QISXPYZVZJBNDM-UHFFFAOYSA-N 0.000 claims 5
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- 229920001223 polyethylene glycol Polymers 0.000 claims 5
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- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims 5
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical group N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims 4
- WVTKBKWTSCPRNU-KYJUHHDHSA-N (+)-Tetrandrine Chemical compound C([C@H]1C=2C=C(C(=CC=2CCN1C)OC)O1)C(C=C2)=CC=C2OC(=C2)C(OC)=CC=C2C[C@@H]2N(C)CCC3=CC(OC)=C(OC)C1=C23 WVTKBKWTSCPRNU-KYJUHHDHSA-N 0.000 claims 4
- 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 claims 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 4
- FAWLNURBQMTKEB-URDPEVQOSA-N 213546-53-3 Chemical compound N([C@@H](C)C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N1[C@@H](CCC1)C(O)=O)C(C)C)C(C)C)C(=O)[C@@H]1CCCN1C(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)N)C(C)C FAWLNURBQMTKEB-URDPEVQOSA-N 0.000 claims 4
- 108010088751 Albumins Proteins 0.000 claims 4
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- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 4
- 102000003964 Histone deacetylase Human genes 0.000 claims 4
- 108090000353 Histone deacetylase Proteins 0.000 claims 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 4
- 108091000080 Phosphotransferase Proteins 0.000 claims 4
- ZZAFFYPNLYCDEP-HNNXBMFYSA-N Rosmarinsaeure Natural products OC(=O)[C@H](Cc1cccc(O)c1O)OC(=O)C=Cc2ccc(O)c(O)c2 ZZAFFYPNLYCDEP-HNNXBMFYSA-N 0.000 claims 4
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- 229940122149 Thymidylate synthase inhibitor Drugs 0.000 claims 4
- 229940122803 Vinca alkaloid Drugs 0.000 claims 4
- MMAXAFOTGLVFQZ-UHFFFAOYSA-N [2-acetyloxy-1,2-bis(oxiran-2-yl)ethyl] acetate Chemical compound C1OC1C(OC(=O)C)C(OC(C)=O)C1CO1 MMAXAFOTGLVFQZ-UHFFFAOYSA-N 0.000 claims 4
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Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014179528A2 (en) * | 2013-05-01 | 2014-11-06 | Brown Dennis M | Compositions and methods to improve the therapeutic benefit of suboptimally administered chemical compounds including substituted naphthalimides such as amonafide for the treatment of immunological, metabolic, infectious, and benign or neoplastic hyperproliferative disease conditions |
| CA2974651A1 (en) | 2014-01-24 | 2015-07-30 | Children's Hospital Of Eastern Ontario Research Institute Inc. | Smc combination therapy for the treatment of cancer |
| WO2016138542A1 (en) * | 2015-02-28 | 2016-09-01 | Cyprus Therapeutics, Inc. | Methods for inhibiting tumors and drug resistance |
| TW201722421A (zh) * | 2015-09-10 | 2017-07-01 | 德瑪製藥公司 | 雙脫水半乳糖醇或其衍生物和類似物藉由dna損傷之誘導和細胞周期之延宕治療非小細胞肺癌、神經膠母細胞瘤及卵巢癌之用途 |
| AU2016382786A1 (en) * | 2015-12-29 | 2018-07-19 | Outlook Therapeutics, Inc. | Buffered formulations of bevacizumab |
| WO2018204323A1 (en) * | 2017-05-01 | 2018-11-08 | Del Mar Pharmaceuticals (Bc) Ltd. | Use of dianhydrogalactitol or analogs and derivatives in combination with vegf inhibitors to treat cancer |
| US10624869B2 (en) | 2017-05-08 | 2020-04-21 | Stanislaw R. Burzynski | Methods for the treatment of recurrent glioblastoma (RGBM) |
| WO2018226939A1 (en) * | 2017-06-07 | 2018-12-13 | Ranedis Pharmaceuticals, Llc | Compositions and methods of treating and/or preventing cancer |
| US11344521B2 (en) | 2017-06-12 | 2022-05-31 | Burzynski Research Institute, Inc. | Methods for the treatment of leptomeningeal disease |
| KR20230124107A (ko) * | 2017-06-12 | 2023-08-24 | 스탠니슬로우 알 벌진스키 | 연수막 질환의 치료 방법 |
| KR20200052349A (ko) | 2017-09-11 | 2020-05-14 | 아토사 테라퓨틱스, 인크. | 엔독시펜을 제조 및 사용하는 방법 |
| WO2019211708A1 (en) * | 2018-05-04 | 2019-11-07 | Kashiv Biosciences, Llc | Stable pharmaceutical compositions of dianhydrogalactitol |
| CN109337884B9 (zh) * | 2018-12-21 | 2021-10-29 | 中国农业科学院北京畜牧兽医研究所 | 一种丙酮酸激酶基因及其应用 |
| US12201591B2 (en) | 2019-07-03 | 2025-01-21 | Atossa Therapeutics, Inc. | Sustained release compositions of endoxifen |
| KR102415193B1 (ko) | 2020-04-16 | 2022-06-29 | 사회복지법인 삼성생명공익재단 | 벤즈브로마론을 유효성분으로 포함하는 뇌암 예방 또는 치료용 약학 조성물 |
| WO2021252432A1 (en) * | 2020-06-08 | 2021-12-16 | Neonc Technologies, Inc. | Compositions and methods for delivering polynucleotides |
| CN114796522A (zh) * | 2022-01-06 | 2022-07-29 | 宁波大学 | 一种靶向线粒体放大氧化应激的新型抗肿瘤纳米药物 |
| WO2024039764A2 (en) * | 2022-08-17 | 2024-02-22 | Ohio State Innovation Foundation | Epitranscriptomic analysis of glioma |
| KR20250052523A (ko) | 2023-10-11 | 2025-04-21 | 서울대학교병원 | 재발성 뇌 종양 진단, 예방 또는 치료에서의 cxcr-4의 용도 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4785077A (en) | 1986-05-05 | 1988-11-15 | Scripps Clinic And Research Foundation | Substantially pure cytotoxicity triggering factor |
| US4801575A (en) * | 1986-07-30 | 1989-01-31 | The Regents Of The University Of California | Chimeric peptides for neuropeptide delivery through the blood-brain barrier |
| US5294430A (en) * | 1988-09-12 | 1994-03-15 | University Of Rochester | Use of dithiocarbamates to treat myelosuppression |
| EP2605650A4 (en) * | 2010-08-18 | 2014-05-21 | Del Mar Pharmaceuticals | COMPOSITIONS AND METHODS FOR INCREASING THE THERAPEUTIC UTILITY OF SUBOPTIMALLY ADMINISTERED CHEMICAL COMPOUNDS INCLUDING SUBSTITUTED HEXITOLS SUCH AS DIANHYDROGALACTITOL AND DIACETYL DIANHYDROGALACTITOL |
| CN110711188A (zh) | 2012-01-20 | 2020-01-21 | 德玛公司 | 经取代的己糖醇类用于治疗恶性肿瘤的用途 |
| US9814693B2 (en) * | 2012-05-09 | 2017-11-14 | Delmar Pharmaceuticals, Inc. | Veterinary use of dianhydrogalactitol, diacetyldianhydrogalactitol, and dibromodulcitol to treat malignancies |
-
2014
- 2014-05-30 TW TW103118945A patent/TW201536278A/zh unknown
- 2014-06-02 MX MX2015016404A patent/MX382824B/es unknown
- 2014-06-02 WO PCT/US2014/040461 patent/WO2014194312A2/en not_active Ceased
- 2014-06-02 AU AU2014273911A patent/AU2014273911B2/en not_active Ceased
- 2014-06-02 BR BR112015029989A patent/BR112015029989A2/pt not_active Application Discontinuation
- 2014-06-02 KR KR1020217025060A patent/KR20210100754A/ko not_active Ceased
- 2014-06-02 JP JP2016517073A patent/JP2016520622A/ja active Pending
- 2014-06-02 CN CN201480042784.2A patent/CN105579044A/zh active Pending
- 2014-06-02 EP EP14804823.4A patent/EP3003321A4/en not_active Withdrawn
- 2014-06-02 KR KR1020227018071A patent/KR20220080199A/ko not_active Ceased
- 2014-06-02 SG SG11201509837QA patent/SG11201509837QA/en unknown
- 2014-06-02 KR KR1020237027741A patent/KR20230124765A/ko not_active Ceased
- 2014-06-02 KR KR1020157037286A patent/KR20160065776A/ko not_active Ceased
- 2014-06-02 CA CA2914025A patent/CA2914025C/en active Active
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2015
- 2015-04-09 US US14/682,226 patent/US11026914B2/en active Active
- 2015-11-30 IL IL242853A patent/IL242853B/en unknown
- 2015-11-30 CL CL2015003512A patent/CL2015003512A1/es unknown
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2019
- 2019-12-18 AU AU2019283893A patent/AU2019283893B2/en not_active Ceased
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2020
- 2020-01-30 JP JP2020013217A patent/JP2020079259A/ja active Pending
-
2022
- 2022-04-04 JP JP2022062257A patent/JP2022088616A/ja active Pending
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