TWI737683B - 用於治療肝癌的組成物和方法 - Google Patents
用於治療肝癌的組成物和方法 Download PDFInfo
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- TWI737683B TWI737683B TW106105214A TW106105214A TWI737683B TW I737683 B TWI737683 B TW I737683B TW 106105214 A TW106105214 A TW 106105214A TW 106105214 A TW106105214 A TW 106105214A TW I737683 B TWI737683 B TW I737683B
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- Prior art keywords
- alkyl
- hydrogen
- methyl
- compound
- heteroaryl
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- 201000007270 liver cancer Diseases 0.000 title claims abstract description 24
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- 238000000034 method Methods 0.000 title abstract description 10
- 239000000203 mixture Substances 0.000 title abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 101
- 125000000217 alkyl group Chemical group 0.000 claims description 86
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 59
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
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- HBZBAMXERPYTFS-SECBINFHSA-N (4S)-2-(6,7-dihydro-5H-pyrrolo[3,2-f][1,3]benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)[C@H]1CSC(=N1)c1nc2cc3CCNc3cc2s1 HBZBAMXERPYTFS-SECBINFHSA-N 0.000 description 1
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- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/20—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- 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
- A61K31/12—Ketones
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- 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
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/543—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings to a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/557—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
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|---|---|---|---|
| US201662296097P | 2016-02-17 | 2016-02-17 | |
| US62/296,097 | 2016-02-17 |
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| TW201733976A TW201733976A (zh) | 2017-10-01 |
| TWI737683B true TWI737683B (zh) | 2021-09-01 |
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| TW106105214A TWI737683B (zh) | 2016-02-17 | 2017-02-17 | 用於治療肝癌的組成物和方法 |
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| KR (1) | KR102399856B1 (OSRAM) |
| CN (1) | CN109069448B (OSRAM) |
| AU (1) | AU2017219871B2 (OSRAM) |
| ES (1) | ES2961932T3 (OSRAM) |
| TW (1) | TWI737683B (OSRAM) |
| WO (1) | WO2017143106A1 (OSRAM) |
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| TW202532056A (zh) * | 2024-01-31 | 2025-08-16 | 國鼎生物科技股份有限公司 | 用於治療肝癌的治療組合物 |
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| EP2233463A1 (en) * | 2007-10-24 | 2010-09-29 | Golden Biotechnology Corporation | New compounds isolated from extract of antrodia camphorata |
| US20150018567A1 (en) * | 2013-02-20 | 2015-01-15 | Golden Biotechnology Corporation | Cyclohexenone Compositions and Process for Making Thereof |
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| TWI394573B (zh) * | 2007-06-14 | 2013-05-01 | 國鼎生物科技股份有限公司 | Application of Cynanchum auranthone Cyclohexenone Compounds in the Preparation of Drugs for Liver Protection |
| FR2987264A1 (fr) * | 2012-02-23 | 2013-08-30 | Golden Biotechnology Corp | Methodes et compositions pour le traitement des metastases cancereuses |
| TWI597061B (zh) * | 2013-02-20 | 2017-09-01 | 國鼎生物科技股份有限公司 | 治療白血病之方法及組成物 |
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2017
- 2017-02-16 CN CN201780011693.6A patent/CN109069448B/zh active Active
- 2017-02-16 WO PCT/US2017/018236 patent/WO2017143106A1/en not_active Ceased
- 2017-02-16 AU AU2017219871A patent/AU2017219871B2/en active Active
- 2017-02-16 US US15/999,358 patent/US10858307B2/en active Active
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- 2017-02-16 JP JP2018539985A patent/JP6932342B2/ja active Active
- 2017-02-17 TW TW106105214A patent/TWI737683B/zh active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2233463A1 (en) * | 2007-10-24 | 2010-09-29 | Golden Biotechnology Corporation | New compounds isolated from extract of antrodia camphorata |
| US20150018567A1 (en) * | 2013-02-20 | 2015-01-15 | Golden Biotechnology Corporation | Cyclohexenone Compositions and Process for Making Thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2017143106A1 (en) | 2017-08-24 |
| JP2019507133A (ja) | 2019-03-14 |
| CN109069448B (zh) | 2021-09-21 |
| US20190112258A1 (en) | 2019-04-18 |
| JP6932342B2 (ja) | 2021-09-08 |
| CA3014057A1 (en) | 2017-08-24 |
| AU2017219871B2 (en) | 2020-09-03 |
| AU2017219871A1 (en) | 2018-08-16 |
| EP3416630B1 (en) | 2023-10-25 |
| EP3416630C0 (en) | 2023-10-25 |
| EP3416630A4 (en) | 2019-10-09 |
| EP3416630A1 (en) | 2018-12-26 |
| US10858307B2 (en) | 2020-12-08 |
| KR20180118634A (ko) | 2018-10-31 |
| CN109069448A (zh) | 2018-12-21 |
| ES2961932T3 (es) | 2024-03-14 |
| KR102399856B1 (ko) | 2022-05-20 |
| TW201733976A (zh) | 2017-10-01 |
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