CA2528764A1 - Thiazoline derivatives as selective androgen receptor modulators (sarms) - Google Patents
Thiazoline derivatives as selective androgen receptor modulators (sarms) Download PDFInfo
- Publication number
- CA2528764A1 CA2528764A1 CA002528764A CA2528764A CA2528764A1 CA 2528764 A1 CA2528764 A1 CA 2528764A1 CA 002528764 A CA002528764 A CA 002528764A CA 2528764 A CA2528764 A CA 2528764A CA 2528764 A1 CA2528764 A1 CA 2528764A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- lower alkyl
- phenyl
- hydrogen
- trifluoromethyl
- 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.)
- Abandoned
Links
- 150000003549 thiazolines Chemical class 0.000 title abstract 2
- 239000000849 selective androgen receptor modulator Substances 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
- 102000001307 androgen receptors Human genes 0.000 claims abstract 2
- 108010080146 androgen receptors Proteins 0.000 claims abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 2
- 208000035475 disorder Diseases 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 229910052739 hydrogen Inorganic materials 0.000 claims 24
- 239000001257 hydrogen Substances 0.000 claims 24
- -1 hydroxy, carboxy Chemical group 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000005907 alkyl ester group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 3
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims 2
- 201000004384 Alopecia Diseases 0.000 claims 2
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010006895 Cachexia Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 206010000496 acne Diseases 0.000 claims 2
- 231100000360 alopecia Toxicity 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 201000001514 prostate carcinoma Diseases 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 206010020112 Hirsutism Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 0 *C1(*)SC(*)=NC1(*)C(N(*)*)=O Chemical compound *C1(*)SC(*)=NC1(*)C(N(*)*)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
-
- 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
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- 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
- A61P17/14—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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P5/26—Androgens
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Virology (AREA)
- Dermatology (AREA)
- Reproductive Health (AREA)
- Pregnancy & Childbirth (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Gynecology & Obstetrics (AREA)
- Diabetes (AREA)
- Tropical Medicine & Parasitology (AREA)
- Urology & Nephrology (AREA)
- AIDS & HIV (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47871203P | 2003-06-13 | 2003-06-13 | |
| US60/478,712 | 2003-06-13 | ||
| PCT/US2004/018665 WO2004113309A1 (en) | 2003-06-13 | 2004-06-12 | Thiazoline derivatives as selective androgen receptor modulators (sarms) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2528764A1 true CA2528764A1 (en) | 2004-12-29 |
Family
ID=33539114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002528764A Abandoned CA2528764A1 (en) | 2003-06-13 | 2004-06-12 | Thiazoline derivatives as selective androgen receptor modulators (sarms) |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20050014952A1 (https=) |
| EP (1) | EP1656360B1 (https=) |
| JP (1) | JP4898446B2 (https=) |
| CN (1) | CN1835937B (https=) |
| AT (1) | ATE370133T1 (https=) |
| AU (1) | AU2004249697B2 (https=) |
| CA (1) | CA2528764A1 (https=) |
| CY (1) | CY1106973T1 (https=) |
| DE (1) | DE602004008300T2 (https=) |
| DK (1) | DK1656360T3 (https=) |
| ES (1) | ES2291906T3 (https=) |
| PL (1) | PL1656360T3 (https=) |
| PT (1) | PT1656360E (https=) |
| WO (1) | WO2004113309A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104803916B (zh) | 2004-11-16 | 2017-08-11 | 詹森药业有限公司 | 用作选择性雄激素受体调节剂(sarms)的杂环衍生物 |
| US7709516B2 (en) | 2005-06-17 | 2010-05-04 | Endorecherche, Inc. | Helix 12 directed non-steroidal antiandrogens |
| US9284345B2 (en) | 2007-04-12 | 2016-03-15 | Endorecherche, Inc. | 17alpha-substituted steroids as systemic antiandrogens and selective androgen receptor modulators |
| CA2861066C (en) * | 2012-01-12 | 2024-01-02 | Yale University | Compounds and methods for the enhanced degradation of targeted proteins and other polypeptides by an e3 ubiquitin ligase |
| CN103450112B (zh) * | 2013-08-07 | 2019-09-13 | 华东理工大学 | 一种n-桥连接的含氮五元杂环化合物及其制备与用途 |
| US9682960B2 (en) | 2013-12-19 | 2017-06-20 | Endorecherche, Inc. | Non-steroidal antiandrogens and selective androgen receptor modulators with a pyridyl moiety |
| WO2019222272A1 (en) | 2018-05-14 | 2019-11-21 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| CN113811333B (zh) | 2019-05-14 | 2024-03-12 | 诺维逊生物股份有限公司 | 靶向抗癌核激素受体的化合物 |
| WO2021097046A1 (en) | 2019-11-13 | 2021-05-20 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| KR20230160299A (ko) | 2021-03-23 | 2023-11-23 | 누베이션 바이오 인크. | 항암 핵 호르몬 수용체 표적화 화합물 |
| US12006314B2 (en) | 2021-05-03 | 2024-06-11 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9602949A (es) * | 1994-01-24 | 1997-06-28 | Du Pont | 2-oxa y tia-zolinas artropodicidas. |
| US6403623B1 (en) * | 1999-05-27 | 2002-06-11 | Unuversity Of Notre Dame Du Lac | Heterocyclic antituberculosis agents |
| EP1401801B1 (en) * | 2000-08-24 | 2006-11-02 | The University Of Tennessee Research Corporation | Selective androgen receptor modulators and methods of use thereof |
-
2004
- 2004-06-12 CN CN2004800230915A patent/CN1835937B/zh not_active Expired - Fee Related
- 2004-06-12 WO PCT/US2004/018665 patent/WO2004113309A1/en not_active Ceased
- 2004-06-12 DE DE602004008300T patent/DE602004008300T2/de not_active Expired - Lifetime
- 2004-06-12 AT AT04755044T patent/ATE370133T1/de active
- 2004-06-12 AU AU2004249697A patent/AU2004249697B2/en not_active Ceased
- 2004-06-12 PL PL04755044T patent/PL1656360T3/pl unknown
- 2004-06-12 DK DK04755044T patent/DK1656360T3/da active
- 2004-06-12 JP JP2006533745A patent/JP4898446B2/ja not_active Expired - Fee Related
- 2004-06-12 CA CA002528764A patent/CA2528764A1/en not_active Abandoned
- 2004-06-12 EP EP04755044A patent/EP1656360B1/en not_active Expired - Lifetime
- 2004-06-12 US US10/866,591 patent/US20050014952A1/en not_active Abandoned
- 2004-06-12 ES ES04755044T patent/ES2291906T3/es not_active Expired - Lifetime
- 2004-06-12 PT PT04755044T patent/PT1656360E/pt unknown
-
2007
- 2007-11-05 CY CY20071101413T patent/CY1106973T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004249697A1 (en) | 2004-12-29 |
| EP1656360A1 (en) | 2006-05-17 |
| AU2004249697B2 (en) | 2010-04-22 |
| ES2291906T3 (es) | 2008-03-01 |
| DE602004008300T2 (de) | 2008-05-08 |
| PL1656360T3 (pl) | 2008-01-31 |
| PT1656360E (pt) | 2007-10-22 |
| JP2007501287A (ja) | 2007-01-25 |
| DK1656360T3 (da) | 2007-12-27 |
| EP1656360B1 (en) | 2007-08-15 |
| ATE370133T1 (de) | 2007-09-15 |
| US20050014952A1 (en) | 2005-01-20 |
| CN1835937A (zh) | 2006-09-20 |
| CY1106973T1 (el) | 2012-09-26 |
| WO2004113309A1 (en) | 2004-12-29 |
| CN1835937B (zh) | 2012-07-18 |
| JP4898446B2 (ja) | 2012-03-14 |
| DE602004008300D1 (de) | 2007-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20130905 |