CA2859224C - Imidazolidinedione compounds and their uses - Google Patents
Imidazolidinedione compounds and their uses Download PDFInfo
- Publication number
- CA2859224C CA2859224C CA2859224A CA2859224A CA2859224C CA 2859224 C CA2859224 C CA 2859224C CA 2859224 A CA2859224 A CA 2859224A CA 2859224 A CA2859224 A CA 2859224A CA 2859224 C CA2859224 C CA 2859224C
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- Prior art keywords
- compound
- deuterated
- mmol
- deuterium
- methyl
- Prior art date
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- 150000001468 imidazolidinediones Chemical class 0.000 title abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 98
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 28
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 18
- 206010000496 acne Diseases 0.000 claims abstract description 15
- 230000000694 effects Effects 0.000 claims abstract description 13
- 102000001307 androgen receptors Human genes 0.000 claims abstract description 12
- 108010080146 androgen receptors Proteins 0.000 claims abstract description 12
- 208000002874 Acne Vulgaris Diseases 0.000 claims abstract description 9
- 201000004384 Alopecia Diseases 0.000 claims abstract description 8
- 229940123407 Androgen receptor antagonist Drugs 0.000 claims abstract description 8
- 231100000360 alopecia Toxicity 0.000 claims abstract description 8
- 239000003936 androgen receptor antagonist Substances 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 230000003660 hair regeneration Effects 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 100
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical group C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 13
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 12
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- -1 imidazolidinedione compound Chemical class 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 7
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- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 claims description 6
- IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 claims description 6
- 229910052736 halogen Chemical group 0.000 claims description 6
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- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 claims description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 5
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- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 claims description 4
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 claims description 3
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- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 3
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- 235000011152 sodium sulphate Nutrition 0.000 description 35
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 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 description 1
- 230000035484 reaction time Effects 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
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- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/28—Antiandrogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011104188590A CN103159680A (zh) | 2011-12-14 | 2011-12-14 | 咪唑二酮类化合物及其用途 |
| CN201110418859.0 | 2011-12-14 | ||
| PCT/CN2012/086573 WO2013087004A1 (zh) | 2011-12-14 | 2012-12-13 | 咪唑二酮类化合物及其用途 |
Publications (2)
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| CA2859224A1 CA2859224A1 (en) | 2013-06-20 |
| CA2859224C true CA2859224C (en) | 2019-03-19 |
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| CA2859224A Active CA2859224C (en) | 2011-12-14 | 2012-12-13 | Imidazolidinedione compounds and their uses |
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| EP (1) | EP2792674B1 (OSRAM) |
| JP (1) | JP5933746B2 (OSRAM) |
| CN (2) | CN103159680A (OSRAM) |
| AU (1) | AU2012350482B2 (OSRAM) |
| CA (1) | CA2859224C (OSRAM) |
| ES (1) | ES2587903T3 (OSRAM) |
| PL (1) | PL2792674T3 (OSRAM) |
| WO (1) | WO2013087004A1 (OSRAM) |
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| CN104211683B (zh) * | 2013-05-29 | 2017-01-11 | 成都海创药业有限公司 | 咪唑二酮类化合物及其用途 |
| KR20160055911A (ko) * | 2013-09-19 | 2016-05-18 | 글락소스미스클라인 엘엘씨 | 조합 약물 요법 |
| WO2015054804A1 (zh) * | 2013-10-14 | 2015-04-23 | 杭州普晒医药科技有限公司 | 恩杂鲁胺的固态形式及其制备方法和用途 |
| CN104803919A (zh) * | 2014-01-26 | 2015-07-29 | 上海医药工业研究院 | 用于制备恩杂鲁胺中间体的方法 |
| WO2016051423A2 (en) * | 2014-10-01 | 2016-04-07 | Laurus Labs Private Limited | An improved process for the preparation of enzalutamide |
| CN106432090B (zh) * | 2015-10-30 | 2019-08-20 | 成都海创药业有限公司 | 一种氘代咪唑酮化合物的晶型及其制备方法和用途 |
| CN107303278B (zh) * | 2016-04-25 | 2020-11-13 | 成都海创药业有限公司 | 一种hc-1119固体分散体及其制备方法 |
| CN107954936B (zh) * | 2016-10-17 | 2021-03-19 | 海创药业股份有限公司 | 一种制备氘代咪唑二酮类化合物的方法 |
| ES2899372T3 (es) * | 2017-02-13 | 2022-03-11 | Kangpu Biopharmaceuticals Ltd | Combinación de tratamiento del cáncer de próstata, composición farmacéutica y método de tratamiento |
| WO2019025250A1 (en) | 2017-08-04 | 2019-02-07 | Basf Se | SUBSTITUTED TRIFLUOROMETHYLOXADIAZOLES FOR COMBATING PHYTOPATHOGENIC FUNGI |
| KR20210016515A (ko) * | 2018-03-29 | 2021-02-16 | 하이노바 파마슈티컬스 인코포레이티드 | 중수소화 이미다졸리딘디온 화합물 및 이의 용도 |
| KR102482289B1 (ko) * | 2018-04-13 | 2022-12-27 | 하이노바 파마슈티컬스 인코포레이티드 | 중수소화 아미드 및 중수소화 설폰아미드의 신규 합성방법 |
| US20210290553A1 (en) * | 2018-05-14 | 2021-09-23 | Hinova Pharmaceuticals Inc. | Hc-1119 formulation, preparation method and use thereof |
| EP3876929A1 (en) | 2018-11-05 | 2021-09-15 | Pfizer Inc. | Combination for treating cancer |
| CN112442009B (zh) * | 2019-08-30 | 2023-10-03 | 润佳（苏州）医药科技有限公司 | 氘代化合物及其在治疗癌症方面的应用 |
| CN115380026B (zh) * | 2020-03-17 | 2023-11-07 | 南京明德新药研发有限公司 | 蛋白降解调节剂与其使用方法 |
| IL300581A (en) | 2020-08-13 | 2023-04-01 | Pfizer | Combined treatment |
| CN114181155A (zh) * | 2021-12-21 | 2022-03-15 | 上海朝晖药业有限公司 | 碘-恩杂鲁胺及其制备方法及其应用 |
| CN115181043B (zh) * | 2022-07-27 | 2024-05-07 | 爱斯特（成都）生物制药股份有限公司 | 一种连续流制备4-异硫氰基-2-(三氟甲基)苯甲腈的方法 |
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| KR101332889B1 (ko) * | 2005-05-13 | 2013-11-26 | 더 리전트 오브 더 유니버시티 오브 캘리포니아 | 디아릴히단토인 화합물 |
| AU2007245022A1 (en) | 2006-03-29 | 2007-11-08 | The Regents Of The University Of California | Diarylthiohydantoin compounds |
| EP4385574A3 (en) | 2006-03-27 | 2024-10-02 | The Regents of the University of California | Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases |
| CN101817787B (zh) * | 2009-02-26 | 2013-07-24 | 童友之 | 抗前列腺癌的雄性激素受体拮抗剂 |
| WO2011029392A1 (en) | 2009-09-10 | 2011-03-17 | Youzhi Tong | Androgen receptor antagonists and uses thereof |
| WO2013067151A1 (en) * | 2011-11-02 | 2013-05-10 | Medivation Prostate Therapeutics, Inc. | Treatment methods using diarylthiohydantoin derivatives |
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2011
- 2011-12-14 CN CN2011104188590A patent/CN103159680A/zh active Pending
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2012
- 2012-12-13 JP JP2014546301A patent/JP5933746B2/ja active Active
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- 2012-12-13 US US14/364,147 patent/US9346764B2/en active Active
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Also Published As
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| EP2792674B1 (en) | 2016-05-25 |
| EP2792674A1 (en) | 2014-10-22 |
| US20140371284A1 (en) | 2014-12-18 |
| HK1198166A1 (en) | 2015-03-13 |
| JP5933746B2 (ja) | 2016-06-15 |
| WO2013087004A1 (zh) | 2013-06-20 |
| PL2792674T3 (pl) | 2016-12-30 |
| CA2859224A1 (en) | 2013-06-20 |
| CN104024228A (zh) | 2014-09-03 |
| EP2792674A4 (en) | 2015-06-17 |
| US9346764B2 (en) | 2016-05-24 |
| AU2012350482A1 (en) | 2014-07-10 |
| ES2587903T3 (es) | 2016-10-27 |
| CN104024228B (zh) | 2015-07-08 |
| CN103159680A (zh) | 2013-06-19 |
| JP2015501820A (ja) | 2015-01-19 |
| AU2012350482B2 (en) | 2017-02-16 |
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| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20170620 |