JP2017524003A5 - - Google Patents
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- JP2017524003A5 JP2017524003A5 JP2017506896A JP2017506896A JP2017524003A5 JP 2017524003 A5 JP2017524003 A5 JP 2017524003A5 JP 2017506896 A JP2017506896 A JP 2017506896A JP 2017506896 A JP2017506896 A JP 2017506896A JP 2017524003 A5 JP2017524003 A5 JP 2017524003A5
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- JP
- Japan
- Prior art keywords
- linear
- branched alkyl
- halogen
- alkyl
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims description 138
- 238000000034 method Methods 0.000 claims description 125
- 229960001592 paclitaxel Drugs 0.000 claims description 100
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 100
- 229910052736 halogen Inorganic materials 0.000 claims description 83
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 76
- 150000002367 halogens Chemical class 0.000 claims description 72
- 206010028980 Neoplasm Diseases 0.000 claims description 58
- 229930012538 Paclitaxel Natural products 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 54
- 229940123469 Fatty acid synthase inhibitor Drugs 0.000 claims description 52
- 201000011510 cancer Diseases 0.000 claims description 44
- 239000008194 pharmaceutical composition Substances 0.000 claims description 44
- 108010058566 130-nm albumin-bound paclitaxel Proteins 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 35
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 239000001301 oxygen Substances 0.000 claims description 35
- 229940123237 Taxane Drugs 0.000 claims description 32
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims description 32
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 230000035945 sensitivity Effects 0.000 claims description 14
- 208000016691 refractory malignant neoplasm Diseases 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 8
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 6
- 206010009944 Colon cancer Diseases 0.000 claims description 6
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
- 206010033128 Ovarian cancer Diseases 0.000 claims description 6
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 6
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
- 206010060862 Prostate cancer Diseases 0.000 claims description 6
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 6
- 208000029742 colonic neoplasm Diseases 0.000 claims description 6
- 201000005202 lung cancer Diseases 0.000 claims description 6
- 208000020816 lung neoplasm Diseases 0.000 claims description 6
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 6
- 201000002528 pancreatic cancer Diseases 0.000 claims description 6
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 6
- 239000002552 dosage form Substances 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- 230000001965 increasing effect Effects 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 2
- 239000008280 blood Substances 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 210000001519 tissue Anatomy 0.000 claims description 2
- 210000002700 urine Anatomy 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 45
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 2
- 229960001573 cabazitaxel Drugs 0.000 claims 2
- BMQGVNUXMIRLCK-OAGWZNDDSA-N cabazitaxel Chemical compound O([C@H]1[C@@H]2[C@]3(OC(C)=O)CO[C@@H]3C[C@@H]([C@]2(C(=O)[C@H](OC)C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=3C=CC=CC=3)C[C@]1(O)C2(C)C)C)OC)C(=O)C1=CC=CC=C1 BMQGVNUXMIRLCK-OAGWZNDDSA-N 0.000 claims 2
- 229960003668 docetaxel Drugs 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 15
- CXQWRCVTCMQVQX-LSDHHAIUSA-N (+)-taxifolin Chemical compound C1([C@@H]2[C@H](C(C3=C(O)C=C(O)C=C3O2)=O)O)=CC=C(O)C(O)=C1 CXQWRCVTCMQVQX-LSDHHAIUSA-N 0.000 description 10
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 10
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 description 10
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
- RSINKZJTTORDAJ-UHFFFAOYSA-N 1,3-bis[4-[(4-methylpyrimidin-2-yl)sulfamoyl]phenyl]urea Chemical compound CC1=CC=NC(NS(=O)(=O)C=2C=CC(NC(=O)NC=3C=CC(=CC=3)S(=O)(=O)NC=3N=C(C)C=CN=3)=CC=2)=N1 RSINKZJTTORDAJ-UHFFFAOYSA-N 0.000 description 5
- GVEZIHKRYBHEFX-MNOVXSKESA-N 13C-Cerulenin Natural products CC=CCC=CCCC(=O)[C@H]1O[C@@H]1C(N)=O GVEZIHKRYBHEFX-MNOVXSKESA-N 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- WHCKCCDPUOWOSW-UHFFFAOYSA-N 3-(4-hydroxypiperidin-1-yl)phthalic acid Chemical compound C1CC(O)CCN1C1=CC=CC(C(O)=O)=C1C(O)=O WHCKCCDPUOWOSW-UHFFFAOYSA-N 0.000 description 5
- VCWLZDVWHQVAJU-UHFFFAOYSA-N 4-methylidene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid Chemical compound CCCCCCCCC1OC(=O)C(=C)C1C(O)=O VCWLZDVWHQVAJU-UHFFFAOYSA-N 0.000 description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 description 5
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- 239000005642 Oleic acid Substances 0.000 description 5
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 5
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 5
- 108010073771 Soybean Proteins Proteins 0.000 description 5
- GVEZIHKRYBHEFX-UHFFFAOYSA-N caerulein A Natural products CC=CCC=CCCC(=O)C1OC1C(N)=O GVEZIHKRYBHEFX-UHFFFAOYSA-N 0.000 description 5
- GVEZIHKRYBHEFX-NQQPLRFYSA-N cerulenin Chemical group C\C=C\C\C=C\CCC(=O)[C@H]1O[C@H]1C(N)=O GVEZIHKRYBHEFX-NQQPLRFYSA-N 0.000 description 5
- 229950005984 cerulenin Drugs 0.000 description 5
- KQNGHARGJDXHKF-UHFFFAOYSA-N dihydrotamarixetin Natural products C1=C(O)C(OC)=CC=C1C1C(O)C(=O)C2=C(O)C=C(O)C=C2O1 KQNGHARGJDXHKF-UHFFFAOYSA-N 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- 235000008777 kaempferol Nutrition 0.000 description 5
- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 description 5
- LRDGATPGVJTWLJ-UHFFFAOYSA-N luteolin Natural products OC1=CC(O)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 LRDGATPGVJTWLJ-UHFFFAOYSA-N 0.000 description 5
- 235000009498 luteolin Nutrition 0.000 description 5
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 5
- 229960001243 orlistat Drugs 0.000 description 5
- -1 platensymycin Chemical compound 0.000 description 5
- 235000005875 quercetin Nutrition 0.000 description 5
- 229960001285 quercetin Drugs 0.000 description 5
- 229940001941 soy protein Drugs 0.000 description 5
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462038113P | 2014-08-15 | 2014-08-15 | |
| US62/038,113 | 2014-08-15 | ||
| PCT/US2015/045244 WO2016025816A1 (en) | 2014-08-15 | 2015-08-14 | Fatty acid synthase inhibitor for use in the treatment of drug resistant cancer |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020003720A Division JP2020055878A (ja) | 2014-08-15 | 2020-01-14 | 薬物耐性癌の治療で用いるための脂肪酸シンターゼ阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017524003A JP2017524003A (ja) | 2017-08-24 |
| JP2017524003A5 true JP2017524003A5 (OSRAM) | 2018-07-26 |
| JP6691909B2 JP6691909B2 (ja) | 2020-05-13 |
Family
ID=54012293
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017506896A Active JP6691909B2 (ja) | 2014-08-15 | 2015-08-14 | 薬物耐性癌の治療で用いるための脂肪酸シンターゼ阻害剤 |
| JP2020003720A Withdrawn JP2020055878A (ja) | 2014-08-15 | 2020-01-14 | 薬物耐性癌の治療で用いるための脂肪酸シンターゼ阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020003720A Withdrawn JP2020055878A (ja) | 2014-08-15 | 2020-01-14 | 薬物耐性癌の治療で用いるための脂肪酸シンターゼ阻害剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10363249B2 (OSRAM) |
| EP (1) | EP3179990B1 (OSRAM) |
| JP (2) | JP6691909B2 (OSRAM) |
| KR (1) | KR102504168B1 (OSRAM) |
| CN (1) | CN106604746B (OSRAM) |
| ES (1) | ES2833454T3 (OSRAM) |
| WO (1) | WO2016025816A1 (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170119786A1 (en) | 2011-03-08 | 2017-05-04 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| EP2870150B1 (en) * | 2012-07-03 | 2019-06-19 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| KR102504168B1 (ko) | 2014-08-15 | 2023-02-27 | 새지메트 바이오사이언시스, 인코포레이티드 | 약물 내성 암의 치료에서 사용하기 위한 지방산 신타제 억제제 |
| ES2910049T3 (es) * | 2015-03-19 | 2022-05-11 | Sagimet Biosciences Inc | Moduladores heterocíclicos de la síntesis de lípidos |
| US11034690B2 (en) * | 2016-11-11 | 2021-06-15 | Saginiet Biosciences Inc. | Heterocyclic modulators of lipid synthesis |
| CA3102279A1 (en) | 2018-06-01 | 2019-12-05 | Cornell University | Combination therapy for pi3k-associated disease or disorder |
| CN108853060B (zh) * | 2018-09-06 | 2020-09-18 | 中山万汉制药有限公司 | 一种包含奥利司他的纳米微球及其制备方法和用途 |
| WO2020191356A1 (en) * | 2019-03-21 | 2020-09-24 | Goncalves Marcus | Anti-fructose therapy for colorectal and small intestine cancers |
| CN113577053A (zh) * | 2021-08-10 | 2021-11-02 | 重庆大学附属肿瘤医院 | 木犀草素在制备靶向抑制卵巢癌干细胞的药物中的应用 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2396269C2 (ru) | 2005-12-01 | 2010-08-10 | Ф.Хоффманн-Ля Рош Аг | Производные гетероарилзамещенного пиперидина в качестве ингибиторов печеночной карнитин пальмитоилтрансферазы (l-cpt1) |
| JP2010502731A (ja) | 2006-09-05 | 2010-01-28 | バイパー サイエンシズ，インコーポレイティド | Ｐａｒｐ阻害剤による脂肪酸合成の阻害、及びその治療方法 |
| WO2008059214A1 (en) | 2006-11-13 | 2008-05-22 | Astrazeneca Ab | Bisamlde derivatives and use thereof as fatty acid synthase inhibitors |
| WO2008075077A1 (en) | 2006-12-21 | 2008-06-26 | Astrazeneca Ab | Piperidine derivatives for the treatment of obesity |
| TW200833663A (en) | 2006-12-21 | 2008-08-16 | Astrazeneca Ab | Therapeutic agents |
| TW200831092A (en) | 2006-12-21 | 2008-08-01 | Astrazeneca Ab | Therapeutic agents |
| EP2683244B1 (en) * | 2011-03-08 | 2017-02-01 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| TWI522348B (zh) * | 2011-03-08 | 2016-02-21 | ３ Ｖ生物科技公司 | 脂質合成之雜環調節劑 |
| US20170119786A1 (en) | 2011-03-08 | 2017-05-04 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| US9624173B2 (en) | 2011-03-08 | 2017-04-18 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| US20130287791A1 (en) * | 2012-04-25 | 2013-10-31 | C. Wilson Xu | Modulation of histone h2b monoubiquitination and treatment of cancer |
| EP2870150B1 (en) | 2012-07-03 | 2019-06-19 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| CA2934251C (en) | 2013-12-20 | 2024-01-02 | 3-V Biosciences, Inc. | A combination of heterocyclic modulators of lipid synthesis and chemotherapeutic drugs in treatment of cancer |
| RU2766087C2 (ru) | 2014-01-07 | 2022-02-07 | Сагимет Байосайенсиз Инк. | Гетероциклические модуляторы синтеза липидов для применения против рака и вирусных инфекций |
| KR102504168B1 (ko) | 2014-08-15 | 2023-02-27 | 새지메트 바이오사이언시스, 인코포레이티드 | 약물 내성 암의 치료에서 사용하기 위한 지방산 신타제 억제제 |
| ES2910049T3 (es) | 2015-03-19 | 2022-05-11 | Sagimet Biosciences Inc | Moduladores heterocíclicos de la síntesis de lípidos |
-
2015
- 2015-08-14 KR KR1020177003131A patent/KR102504168B1/ko active Active
- 2015-08-14 ES ES15756742T patent/ES2833454T3/es active Active
- 2015-08-14 JP JP2017506896A patent/JP6691909B2/ja active Active
- 2015-08-14 CN CN201580042834.1A patent/CN106604746B/zh active Active
- 2015-08-14 WO PCT/US2015/045244 patent/WO2016025816A1/en not_active Ceased
- 2015-08-14 EP EP15756742.1A patent/EP3179990B1/en active Active
- 2015-08-14 US US15/503,809 patent/US10363249B2/en active Active
-
2020
- 2020-01-14 JP JP2020003720A patent/JP2020055878A/ja not_active Withdrawn
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