CA2883545C - Imidazoline derivatives, preparation methods thereof, and their applications in medicine - Google Patents

Imidazoline derivatives, preparation methods thereof, and their applications in medicine Download PDF

Info

Publication number
CA2883545C
CA2883545C CA2883545A CA2883545A CA2883545C CA 2883545 C CA2883545 C CA 2883545C CA 2883545 A CA2883545 A CA 2883545A CA 2883545 A CA2883545 A CA 2883545A CA 2883545 C CA2883545 C CA 2883545C
Authority
CA
Canada
Prior art keywords
oxo
compound
formula
alkyl
mmol
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.)
Active
Application number
CA2883545A
Other languages
English (en)
French (fr)
Other versions
CA2883545A1 (en
Inventor
Hejun Lu
Piaoyang Sun
Hongbo Fei
Hongjian Jiang
Haowei Wang
Qing Dong
Original Assignee
Jiangsu Hengrui Medicine Co Ltd
Shanghai Hengrui Pharmaceutical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Jiangsu Hengrui Medicine Co Ltd, Shanghai Hengrui Pharmaceutical Co Ltd filed Critical Jiangsu Hengrui Medicine Co Ltd
Publication of CA2883545A1 publication Critical patent/CA2883545A1/en
Application granted granted Critical
Publication of CA2883545C publication Critical patent/CA2883545C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • 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
    • 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
    • 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
    • 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
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/08—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis for Pneumocystis carinii
    • 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
    • C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—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
    • C07D405/02—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
    • C07D405/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—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
    • C07D409/12—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 linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Endocrinology (AREA)
  • Dermatology (AREA)
  • Urology & Nephrology (AREA)
  • Diabetes (AREA)
  • Gynecology & Obstetrics (AREA)
  • Reproductive Health (AREA)
  • Nutrition Science (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2883545A 2012-09-04 2013-08-26 Imidazoline derivatives, preparation methods thereof, and their applications in medicine Active CA2883545C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN201210323870.3 2012-09-04
CN201210323870 2012-09-04
PCT/CN2013/082273 WO2014036897A1 (zh) 2012-09-04 2013-08-26 咪唑啉类衍生物、其制备方法及其在医药上的应用

Publications (2)

Publication Number Publication Date
CA2883545A1 CA2883545A1 (en) 2014-03-13
CA2883545C true CA2883545C (en) 2020-07-07

Family

ID=50236528

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2883545A Active CA2883545C (en) 2012-09-04 2013-08-26 Imidazoline derivatives, preparation methods thereof, and their applications in medicine

Country Status (22)

Country Link
US (2) US9586947B2 (https=)
EP (1) EP2894151B1 (https=)
JP (1) JP6262733B2 (https=)
KR (1) KR102189940B1 (https=)
CN (1) CN103958480B (https=)
AU (1) AU2013312587B2 (https=)
BR (1) BR112015004637B1 (https=)
CA (1) CA2883545C (https=)
CY (1) CY1123649T1 (https=)
DK (1) DK2894151T3 (https=)
ES (1) ES2835248T3 (https=)
HR (1) HRP20202050T1 (https=)
HU (1) HUE052904T2 (https=)
LT (1) LT2894151T (https=)
MX (1) MX368844B (https=)
PT (1) PT2894151T (https=)
RS (1) RS61242B1 (https=)
RU (1) RU2639145C2 (https=)
SI (1) SI2894151T1 (https=)
SM (1) SMT202000672T1 (https=)
TW (1) TWI617546B (https=)
WO (1) WO2014036897A1 (https=)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RS61242B1 (sr) * 2012-09-04 2021-01-29 Shanghai hengrui pharmaceutical co ltd Derivati imidazolina, postupci njihove pripreme i njihove primene u medicini
JP6817962B2 (ja) * 2015-01-20 2021-01-20 アルビナス・オペレーションズ・インコーポレイテッドＡｒｖｉｎａｓ Ｏｐｅｒａｔｉｏｎｓ， Ｉｎｃ． ターゲティングされたアンドロゲン受容体分解のための化合物および方法
US12312316B2 (en) 2015-01-20 2025-05-27 Arvinas Operations, Inc. Compounds and methods for the targeted degradation of androgen receptor
WO2017011371A1 (en) 2015-07-10 2017-01-19 Arvinas, Inc Mdm2-based modulators of proteolysis and associated methods of use
CA2988436A1 (en) * 2015-07-13 2017-01-19 Arvinas, Inc. Alanine-based modulators of proteolysis and associated methods of use
SI3348546T1 (sl) * 2015-09-10 2020-09-30 Jiangsu Hengrui Medicine Co., Ltd. Kristalinična oblika zaviralca androgenega receptorja in postopek priprave le-tega
CN106518773A (zh) * 2015-09-10 2017-03-22 江苏恒瑞医药股份有限公司 一种雄性激素受体抑制剂的结晶形式及其制备方法
TWI726969B (zh) 2016-01-11 2021-05-11 比利時商健生藥品公司 用作雄性激素受體拮抗劑之經取代之硫尿囊素衍生物
US9963433B2 (en) * 2016-01-29 2018-05-08 Wayne State University Anticancer drugs including the chemical structures of an androgen receptor ligand and a histone deacetylase inhibitor
AU2017220970B2 (en) * 2016-02-19 2021-12-16 Jiangsu Hengrui Medicine Co., Ltd. Pharmaceutical composition containing imidazoline derivative
EP3481394A1 (en) * 2016-07-08 2019-05-15 Janssen Pharmaceutica N.V. Thiohydantoin androgen receptor antagonists for the treatment of cancer
CN110023297A (zh) * 2016-07-08 2019-07-16 詹森药业有限公司 作为雄性激素受体拮抗剂的取代的乙内酰脲和硫代己内酰脲衍生物
AU2017202864B2 (en) 2017-02-13 2020-04-23 Kangpu Biopharmaceuticals, Ltd. Combination treating prostate cancer, pharmaceutical composition and treatment method
CN112300076B (zh) * 2017-12-13 2022-10-25 江苏恒瑞医药股份有限公司 一种雄性激素受体抑制剂的晶型及其制备方法
CN110684046B (zh) * 2018-07-06 2023-05-12 江苏恒瑞医药股份有限公司 一种新的咪唑啉类衍生物的制备方法
CN108976171B (zh) * 2018-08-27 2020-06-16 长沙泽达医药科技有限公司 化合物、组合物及其在药物制备中的用途
JP7542538B2 (ja) 2018-09-18 2024-08-30 ニカング セラピューティクス， インコーポレイテッド Ｓｒｃホモロジー－２ホスファターゼ阻害剤としての縮合三環式環誘導体
WO2020083187A1 (zh) * 2018-10-22 2020-04-30 江苏恒瑞医药股份有限公司 一种ar拮抗剂联合parp抑制剂在制备治疗前列腺癌的药物中的用途
US11325889B2 (en) * 2018-12-19 2022-05-10 Celgene Corporation Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewith
PL3897636T3 (pl) 2018-12-19 2025-04-28 Celgene Corporation Podstawione związki 3-((3-aminofenylo)amino)piperydyno-2,6-dionu, ich kompozycje i sposoby leczenia nimi
GB201908511D0 (en) 2019-06-13 2019-07-31 Adorx Therapeutics Ltd Hydroxamate compounds
CN113929628A (zh) * 2020-06-29 2022-01-14 江苏恒瑞医药股份有限公司 一种咪唑啉衍生物的制备方法
CN113024513A (zh) * 2021-03-22 2021-06-25 中国药科大学 新型雄激素受体降解剂、制备方法和医药用途
CN117327019A (zh) * 2022-06-23 2024-01-02 南京思聚生物医药有限公司 一种局部作用的雄激素受体拮抗剂的应用
CN115850186B (zh) * 2023-02-07 2024-04-09 长沙泽达医药科技有限公司 一种乙撑硫脲衍生物的晶型及用途
CN118993935B (zh) * 2024-10-23 2025-02-14 江苏恒瑞医药股份有限公司 咪唑啉衍生物或其盐的制备方法

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6713474B2 (en) 1998-09-18 2004-03-30 Abbott Gmbh & Co. Kg Pyrrolopyrimidines as therapeutic agents
SE0100902D0 (sv) * 2001-03-15 2001-03-15 Astrazeneca Ab Compounds
CN100562516C (zh) 2001-12-27 2009-11-25 第一制药株式会社 β-淀粉样蛋白产生和分泌的抑制剂
US20060025589A1 (en) * 2002-10-01 2006-02-02 Jean Binet 2-Thiohydantoine derivative compounds and use thereof for the treatment of diabetes
TW200621723A (en) * 2004-09-09 2006-07-01 Chugai Pharmaceutical Co Ltd Novel imidazolidine derivative and use thereof
US20070015782A1 (en) 2005-04-15 2007-01-18 Eisai Co., Ltd. Benzimidazole compound
US7709517B2 (en) * 2005-05-13 2010-05-04 The Regents Of The University Of California Diarylhydantoin compounds
JP4644737B2 (ja) * 2005-05-13 2011-03-02 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア ジアリールヒダントイン化合物
BRPI0713378A8 (pt) 2006-06-27 2018-01-02 Takeda Pharmaceutical composto, pró-droga, modulador da função do receptor gpr40, agente farmacêutico uso do composto, e, método de produção de uma forma opticamente ativa de um composto
ES2427917T3 (es) 2009-02-10 2013-11-04 Astrazeneca Ab Derivados de triazolo [4,3-b] piridazina y sus usos para el cáncer de próstata
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
EP2416657A4 (en) * 2009-04-09 2012-09-05 Medivation Prostate Therapeutics Inc COMPOUNDS COMPRISING SUBSTITUTED DI-ARYLHYDANTOIDS AND DI-ARYLTHIOHYDANTOINES AND METHODS OF USE THEREOF
US8450374B2 (en) 2009-06-29 2013-05-28 University Of Delaware Pan-antagonists for the androgen receptor and androgen receptor mutants associated with anti-androgen withdrawal
JP2013505295A (ja) 2009-09-22 2013-02-14 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Ｃｂ２受容体を選択的に調節する化合物
MX2012009561A (es) 2010-02-17 2012-11-23 Amgen Inc Carboxamidas como inhibidores de canales de sodio dependientes del voltaje.
RU2434851C1 (ru) 2010-07-22 2011-11-27 Александр Васильевич Иващенко Циклические n, n'-диарилтиомочевины или n, n'-диарилмочевины - антагонисты андрогенных рецепторов, противораковое средство, способ получения и применения
CN103209960A (zh) 2010-07-26 2013-07-17 百时美施贵宝公司 用作cyp17抑制剂的磺酰胺化合物
WO2012050868A1 (en) * 2010-09-28 2012-04-19 Georgia Tech Research Corporation Histone deacetylase (hdac) inhibitors targeting prostate tumors and methods of making and using thereof
RU2576316C2 (ru) 2010-11-03 2016-02-27 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Пестицидная композиция, способ контроля вредителей, способ контроля эндопаразитов, эктопаразитов или обоих и способ усиления жизнестойкости растений
DK2683694T3 (en) 2011-03-10 2016-07-18 Suzhou Kintor Pharmaceuticals Inc ANDROGEN RECEPTOR ANTAGONISTS AND APPLICATIONS THEREOF
RS61242B1 (sr) * 2012-09-04 2021-01-29 Shanghai hengrui pharmaceutical co ltd Derivati imidazolina, postupci njihove pripreme i njihove primene u medicini

Also Published As

Publication number Publication date
JP2015526487A (ja) 2015-09-10
RU2639145C2 (ru) 2017-12-20
AU2013312587A1 (en) 2015-03-19
KR20150047591A (ko) 2015-05-04
MX368844B (es) 2019-10-16
SMT202000672T1 (it) 2021-01-05
HK1198476A1 (zh) 2015-05-08
CN103958480A (zh) 2014-07-30
US20150225381A1 (en) 2015-08-13
RU2015110122A (ru) 2016-10-27
JP6262733B2 (ja) 2018-01-17
US9895355B2 (en) 2018-02-20
PT2894151T (pt) 2020-12-07
MX2015002602A (es) 2015-06-10
HUE052904T2 (hu) 2021-05-28
AU2013312587B2 (en) 2017-03-16
SI2894151T1 (sl) 2021-01-29
HRP20202050T1 (hr) 2021-02-19
RS61242B1 (sr) 2021-01-29
KR102189940B1 (ko) 2020-12-14
CN103958480B (zh) 2016-04-06
CY1123649T1 (el) 2022-03-24
BR112015004637A2 (pt) 2017-07-04
EP2894151A4 (en) 2016-01-20
US20170128422A1 (en) 2017-05-11
DK2894151T3 (da) 2021-01-11
ES2835248T3 (es) 2021-06-22
TW201410655A (zh) 2014-03-16
BR112015004637B1 (pt) 2022-04-05
LT2894151T (lt) 2021-09-10
WO2014036897A1 (zh) 2014-03-13
EP2894151B1 (en) 2020-11-11
CA2883545A1 (en) 2014-03-13
EP2894151A1 (en) 2015-07-15
TWI617546B (zh) 2018-03-11
US9586947B2 (en) 2017-03-07

Similar Documents

Publication Publication Date Title
CA2883545C (en) Imidazoline derivatives, preparation methods thereof, and their applications in medicine
TWI762544B (zh) 新穎cyp11a1抑制劑
CN102264707B (zh) 双环型杂环化合物
EP2994469B1 (en) Benzimidazole derivatives as bromodomain inhibitors
EP2921480B1 (en) Nitrogen-containing heterocyclic compound
JP6907351B2 (ja) 選択的アンドロゲン受容体モジュレーターとしてのカルボニトリル誘導体
US11084784B2 (en) ROR-gamma modulators and uses thereof
KR102082331B1 (ko) Cot 조정제로서의 6-아미노-퀴놀린-3-카르보니트릴
JP2022548028A (ja) Ｍａｇｌ阻害剤としての４，４ａ，５，７，８，８ａ－ヘキサピリド［４，３－ｂ］［１，４］オキサジン－３－オン化合物
CN115572252A (zh) 具有抗癌活性的mdm2-p53相互作用的异吲哚啉酮抑制剂
CA2923269A1 (en) Cycloalkyl acid derivative, preparation method thereof, and pharmaceutical application thereof
WO2025262003A1 (en) Dihydro benzoxazine derivatives
TW200906820A (en) Piperidine derivative
HK1198476B (en) Imidazoline derivatives, preparation methods thereof, and their applications in medicine
NZ740737B2 (en) Isoindolinone inhibitors of the mdm2-p53 interaction having anticancer activity
HK1162504B (en) Novel bicyclic heterocyclic compound
HK1163676B (en) Bicyclic heterocyclic compound

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20180529

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 11TH ANNIV.) - STANDARD

Year of fee payment: 11

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20240724

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20240724

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20240724

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 12TH ANNIV.) - STANDARD

Year of fee payment: 12

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20250725

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20250828