JPWO2019224790A5 - - Google Patents
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- Publication number
- JPWO2019224790A5 JPWO2019224790A5 JP2021515306A JP2021515306A JPWO2019224790A5 JP WO2019224790 A5 JPWO2019224790 A5 JP WO2019224790A5 JP 2021515306 A JP2021515306 A JP 2021515306A JP 2021515306 A JP2021515306 A JP 2021515306A JP WO2019224790 A5 JPWO2019224790 A5 JP WO2019224790A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- aryl
- alkyl
- optionally substituted
- group
- 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.)
- Granted
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- 125000003118 aryl group Chemical group 0.000 claims description 108
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 95
- 125000001072 heteroaryl group Chemical group 0.000 claims description 94
- 229910052739 hydrogen Inorganic materials 0.000 claims description 86
- 239000001257 hydrogen Substances 0.000 claims description 86
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 80
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 77
- 125000003342 alkenyl group Chemical group 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 125000000304 alkynyl group Chemical group 0.000 claims description 69
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 67
- 229910019142 PO4 Inorganic materials 0.000 claims description 56
- 239000010452 phosphate Substances 0.000 claims description 56
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
- 239000012453 solvate Substances 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 28
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 28
- -1 alkyl phosphate Chemical compound 0.000 claims description 28
- 125000004414 alkyl thio group Chemical group 0.000 claims description 28
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 28
- 229920006395 saturated elastomer Polymers 0.000 claims description 28
- 125000002252 acyl group Chemical group 0.000 claims description 26
- 238000006467 substitution reaction Methods 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 14
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 14
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000003107 substituted aryl group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 210000000481 breast Anatomy 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 230000003211 malignant effect Effects 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 210000000056 organ Anatomy 0.000 claims description 5
- 230000001850 reproductive effect Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 2
- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 210000005000 reproductive tract Anatomy 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical class C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical class C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001541 aziridines Chemical class 0.000 claims 1
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical class C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 229940126585 therapeutic drug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 description 8
- 229940002612 prodrug Drugs 0.000 description 8
- 238000000034 method Methods 0.000 description 4
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 2
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023191446A JP7653092B2 (ja) | 2018-05-24 | 2023-11-09 | フルベストラントのプロドラッグ |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN201821019542 | 2018-05-24 | ||
| IN201821019542 | 2018-05-24 | ||
| IN201821047939 | 2018-12-18 | ||
| IN201821047939 | 2018-12-18 | ||
| PCT/IB2019/054315 WO2019224790A2 (en) | 2018-05-24 | 2019-05-24 | Prodrugs of fulvestrant |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023191446A Division JP7653092B2 (ja) | 2018-05-24 | 2023-11-09 | フルベストラントのプロドラッグ |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2021525278A JP2021525278A (ja) | 2021-09-24 |
| JP2021525278A5 JP2021525278A5 (https=) | 2022-06-13 |
| JPWO2019224790A5 true JPWO2019224790A5 (https=) | 2022-06-13 |
| JP7384903B2 JP7384903B2 (ja) | 2023-11-21 |
Family
ID=68615936
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021515306A Active JP7384903B2 (ja) | 2018-05-24 | 2019-05-24 | フルベストラントのプロドラッグ |
| JP2023191446A Active JP7653092B2 (ja) | 2018-05-24 | 2023-11-09 | フルベストラントのプロドラッグ |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023191446A Active JP7653092B2 (ja) | 2018-05-24 | 2023-11-09 | フルベストラントのプロドラッグ |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20210253626A1 (https=) |
| EP (1) | EP3801553B1 (https=) |
| JP (2) | JP7384903B2 (https=) |
| AU (1) | AU2019274815B2 (https=) |
| CA (1) | CA3101421C (https=) |
| WO (1) | WO2019224790A2 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7384903B2 (ja) * | 2018-05-24 | 2023-11-21 | ケーアイ ファーマシューティカルズ，リミテッド・ライアビリティ・カンパニー | フルベストラントのプロドラッグ |
| EP4061376A4 (en) * | 2019-11-24 | 2024-03-13 | Kashiv Biosciences, LLC | Prodrugs of fulvestrant |
| TW202146405A (zh) * | 2020-02-25 | 2021-12-16 | 日商大日本住友製藥股份有限公司 | Cdk9抑制劑前體藥物及內封其之脂質體 |
| WO2022034587A1 (en) * | 2020-08-10 | 2022-02-17 | Tnik Therapeutics Ltd | Traf2- AND Nck-INTERACTING KINASE (TNIK) INHIBITORS AND USES THEREOF |
| WO2023027032A1 (ja) * | 2021-08-23 | 2023-03-02 | 住友ファーマ株式会社 | 自己分解型ｃｄｋ９阻害剤プロドラッグ及びそれを内封するリポソーム |
| AU2022377397A1 (en) * | 2021-10-29 | 2024-06-13 | Kashiv Biosciences, Llc | Inectable pharmaceutical composition for treatment of breast cancer |
| CN117957238A (zh) * | 2021-12-06 | 2024-04-30 | 江苏亚虹医药科技股份有限公司 | 氟维司群衍生物及其制备方法和医药用途 |
| EP4444318A4 (en) * | 2021-12-06 | 2026-01-28 | Amneal Pharmaceuticals Llc | COMPOUNDS FOR CANCER TREATMENT |
| CN119751533B (zh) * | 2025-03-10 | 2026-01-13 | 山东大学 | 一种基于雌甾三烯结构的雌激素受体蛋白靶向降解嵌合体衍生物及其制备方法和应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0000313D0 (en) | 2000-01-10 | 2000-03-01 | Astrazeneca Uk Ltd | Formulation |
| GB0008172D0 (en) * | 2000-04-05 | 2000-05-24 | Astrazeneca Ab | Therapy |
| CN102600073B (zh) * | 2012-03-31 | 2014-01-01 | 莱普德制药有限公司 | 以乳酸酯为基础的氟维司群或其衍生物油性制剂及其制备方法 |
| CA2909418A1 (en) * | 2013-04-18 | 2014-10-23 | Xi'an Libang Pharmaceutical Technology Co., Ltd. | Ester derivative of 7-.alpha.-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)n onyl]-estra-1,3,5(10)-triene-3,17.beta.-diol having anticancer activity and preparation method thereof |
| CN103421069A (zh) | 2013-05-23 | 2013-12-04 | 中国海洋大学 | 氟维司群磷酸酯衍生物及其制备方法和应用 |
| US10112962B2 (en) | 2014-07-02 | 2018-10-30 | Xavier University | Boron-based prodrug strategy for increased bioavailability and lower-dosage requirements for drug molecules containing at least one phenol (or aromatic hydroxyl) group |
| 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 |
| CN108159055A (zh) * | 2018-01-04 | 2018-06-15 | 西安力邦医药科技有限责任公司 | 治疗乳腺癌的长效递药系统、其制备方法及应用 |
| JP7384903B2 (ja) * | 2018-05-24 | 2023-11-21 | ケーアイ ファーマシューティカルズ，リミテッド・ライアビリティ・カンパニー | フルベストラントのプロドラッグ |
-
2019
- 2019-05-24 JP JP2021515306A patent/JP7384903B2/ja active Active
- 2019-05-24 AU AU2019274815A patent/AU2019274815B2/en active Active
- 2019-05-24 WO PCT/IB2019/054315 patent/WO2019224790A2/en not_active Ceased
- 2019-05-24 US US17/058,390 patent/US20210253626A1/en active Pending
- 2019-05-24 CA CA3101421A patent/CA3101421C/en active Active
- 2019-05-24 EP EP19808360.2A patent/EP3801553B1/en active Active
-
2023
- 2023-11-09 JP JP2023191446A patent/JP7653092B2/ja active Active
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