CN104803916B - 用作选择性雄激素受体调节剂(sarms)的杂环衍生物 - Google Patents
用作选择性雄激素受体调节剂(sarms)的杂环衍生物 Download PDFInfo
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- CN104803916B CN104803916B CN201510087784.0A CN201510087784A CN104803916B CN 104803916 B CN104803916 B CN 104803916B CN 201510087784 A CN201510087784 A CN 201510087784A CN 104803916 B CN104803916 B CN 104803916B
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- Prior art keywords
- trifluoromethyl
- methyl
- phenyls
- dihydro
- cyano group
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- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940083608 sodium hydroxide Drugs 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
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- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N thianaphthalene Natural products C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
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- 230000037317 transdermal delivery Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A—HUMAN NECESSITIES
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
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- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
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- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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| JP5230448B2 (ja) * | 2006-02-10 | 2013-07-10 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 選択的アンドローゲン受容体モジュレーターとして有用な新イミダゾロピラゾール誘導体 |
| DE102006047617B4 (de) * | 2006-10-09 | 2008-11-27 | Clariant International Limited | Verfahren zur Herstellung basischer (Meth)acrylamide |
| US8268872B2 (en) * | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| US8067448B2 (en) | 2008-02-22 | 2011-11-29 | Radius Health, Inc. | Selective androgen receptor modulators |
| MX338831B (es) | 2010-02-04 | 2016-05-03 | Radius Health Inc | Moduladores selectivos de receptores de androgenos. |
| SI2568806T1 (sl) | 2010-05-12 | 2016-09-30 | Radius Health, Inc. | Režimi zdravljenja |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| US9290485B2 (en) | 2010-08-04 | 2016-03-22 | Novartis Ag | N-((6-amino-pyridin-3-yl)methyl)-heteroaryl-carboxamides |
| AU2011312490B2 (en) | 2010-09-28 | 2015-06-25 | Radius Pharmaceuticals, Inc. | Selective androgen receptor modulators |
| PT3122426T (pt) | 2014-03-28 | 2023-02-28 | Univ Duke | Tratamento de cancro da mama utilizando moduladores seletivos do recetor de estrogénio |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| US10654809B2 (en) | 2016-06-10 | 2020-05-19 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| HRP20220619T1 (hr) | 2016-06-22 | 2023-02-03 | Ellipses Pharma Ltd | Postupci za liječenje ar+ raka dojke |
| CN109661229B (zh) * | 2016-06-29 | 2022-06-28 | 加利福尼亚大学董事会 | 用于治疗癌症的化合物和组合物 |
| CN106748884B (zh) * | 2016-12-13 | 2021-08-20 | 山西振东制药股份有限公司 | 一种比卡鲁胺中间体的制备方法 |
| ES2981967T3 (es) | 2017-01-05 | 2024-10-14 | Radius Pharmaceuticals Inc | Formas polimórficas de RAD1901-2HCl |
| WO2018175449A1 (en) | 2017-03-21 | 2018-09-27 | AbbVie Deutschland GmbH & Co. KG | Proline amide compounds and their azetidine analogues carrying a specifically substituted benzyl radical |
| US20190375732A1 (en) | 2018-05-14 | 2019-12-12 | David Hung | Anti-cancer nuclear hormone receptor-targeting compounds |
| JP7473486B2 (ja) | 2018-07-04 | 2024-04-23 | ラジウス ファーマシューティカルズ，インコーポレイテッド | Ｒａｄ１９０１－２ｈｃｌの多形形態 |
| JOP20210218A1 (ar) | 2019-02-12 | 2023-01-30 | Radius Pharmaceuticals Inc | عمليات ومركبات |
| KR20220008869A (ko) | 2019-05-14 | 2022-01-21 | 누베이션 바이오 인크. | 항암 핵 호르몬 수용체-표적화 화합물 |
| TW202131930A (zh) | 2019-11-13 | 2021-09-01 | 美商諾維雪碧歐公司 | 抗癌核荷爾蒙受體標靶化合物 |
| BR112023019420A2 (pt) | 2021-03-23 | 2023-10-24 | Nuvation Bio Inc | Compostos de direcionamento ao receptor de hormônio nuclear anticâncer |
| EP4334314A1 (en) | 2021-05-03 | 2024-03-13 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| WO2024010817A2 (en) * | 2022-07-07 | 2024-01-11 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (sard) o-linked ligands and methods of use thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998022432A1 (en) * | 1996-11-18 | 1998-05-28 | Yamanouchi Pharmaceutical Co., Ltd. | Novel acylamino-substituted acylanilide derivatives or pharmaceutical composition comprising the same |
| CN1416416A (zh) * | 2000-02-11 | 2003-05-07 | 生物物理公司 | 前列腺癌、脱发和其他雄激素过多综合征的治疗和诊断中的雄激素受体抑制剂 |
| CN1492869A (zh) * | 2001-02-23 | 2004-04-28 | ���ʵ�ҩƷ��˾ | 三环雄激素受体调节剂化合物和方法 |
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| US6339099B1 (en) * | 1997-06-20 | 2002-01-15 | Dupont Pharmaceuticals Company | Guanidine mimics as factor Xa inhibitors |
| DE69914931T2 (de) * | 1998-10-09 | 2004-12-16 | Janssen Pharmaceutica N.V. | 4,5-dehydroisoxazole derivate und ihre pharmazeutische verwendung |
| AU2001273040A1 (en) | 2000-06-27 | 2002-01-08 | Du Pont Pharmaceuticals Company | Factor xa inhibitors |
| US6657770B2 (en) * | 2001-06-22 | 2003-12-02 | Lucent Technologies Inc. | Programmable optical multiplexer/demultiplexer |
| US6738540B2 (en) * | 2001-06-22 | 2004-05-18 | Lucent Technologies Inc. | Optical cross-connect switch using programmable multiplexers/demultiplexers |
| US7030141B2 (en) * | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| EP1656360B1 (en) | 2003-06-13 | 2007-08-15 | Janssen Pharmaceutica N.V. | Thiazoline derivatives as selective androgen receptor modulators (sarms) |
| EP1791821B1 (en) * | 2004-09-10 | 2013-06-05 | Janssen Pharmaceutica NV | Novel imidazolidin-2-one derivatives as selective androgen receptor modulators (sarms) |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998022432A1 (en) * | 1996-11-18 | 1998-05-28 | Yamanouchi Pharmaceutical Co., Ltd. | Novel acylamino-substituted acylanilide derivatives or pharmaceutical composition comprising the same |
| CN1416416A (zh) * | 2000-02-11 | 2003-05-07 | 生物物理公司 | 前列腺癌、脱发和其他雄激素过多综合征的治疗和诊断中的雄激素受体抑制剂 |
| CN1492869A (zh) * | 2001-02-23 | 2004-04-28 | ���ʵ�ҩƷ��˾ | 三环雄激素受体调节剂化合物和方法 |
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| US7781473B2 (en) | 2010-08-24 |
| CN101103003A (zh) | 2008-01-09 |
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| CA2587678A1 (en) | 2006-05-26 |
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| US20060211756A1 (en) | 2006-09-21 |
| JP4969451B2 (ja) | 2012-07-04 |
| EP1817292A2 (en) | 2007-08-15 |
| TWI483725B (zh) | 2015-05-11 |
| TW200621235A (en) | 2006-07-01 |
| AU2005307003A1 (en) | 2006-05-26 |
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| EP1817292B1 (en) | 2015-04-08 |
| JP2008520665A (ja) | 2008-06-19 |
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| WO2006055184A2 (en) | 2006-05-26 |
| US20100267670A1 (en) | 2010-10-21 |
| MY142048A (en) | 2010-08-30 |
| US7465809B2 (en) | 2008-12-16 |
| US20090131365A1 (en) | 2009-05-21 |
| CN104803916A (zh) | 2015-07-29 |
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