EA017429B1 - Циклические аминные соединения - Google Patents
Циклические аминные соединения Download PDFInfo
- Publication number
- EA017429B1 EA017429B1 EA201070246A EA201070246A EA017429B1 EA 017429 B1 EA017429 B1 EA 017429B1 EA 201070246 A EA201070246 A EA 201070246A EA 201070246 A EA201070246 A EA 201070246A EA 017429 B1 EA017429 B1 EA 017429B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- mixture
- solution
- group
- ethyl
- hydroxy
- Prior art date
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- -1 Cyclic amine compounds Chemical class 0.000 title claims description 124
- 150000001875 compounds Chemical class 0.000 claims abstract description 321
- 150000003839 salts Chemical class 0.000 claims abstract description 57
- 108010080146 androgen receptors Proteins 0.000 claims abstract description 12
- 102000001307 androgen receptors Human genes 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 85
- 238000002360 preparation method Methods 0.000 claims description 68
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- 210000003205 muscle Anatomy 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 210000002307 prostate Anatomy 0.000 claims description 14
- 206010006895 Cachexia Diseases 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
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- 208000001132 Osteoporosis Diseases 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
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Classifications
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007205966 | 2007-08-07 | ||
| JP2007299658 | 2007-11-19 | ||
| PCT/JP2008/064500 WO2009020234A2 (en) | 2007-08-07 | 2008-08-06 | Pyrrolidin-2 -one derivatives as androgen receptor modulator |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201070246A1 EA201070246A1 (ru) | 2010-08-30 |
| EA017429B1 true EA017429B1 (ru) | 2012-12-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201070246A EA017429B1 (ru) | 2007-08-07 | 2008-08-06 | Циклические аминные соединения |
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| WO (1) | WO2009020234A2 (https=) |
| ZA (1) | ZA201001289B (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ME01579B (me) * | 2007-08-07 | 2014-09-20 | Takeda Pharmaceuticals Co | Derivati pirolidin-2-ona kao modulatori androgenskih receptora |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| CA2716320C (en) * | 2008-02-22 | 2014-01-28 | Radius Health, Inc. | Selective androgen receptor modulators |
| PE20091653A1 (es) * | 2008-03-26 | 2009-11-14 | Takeda Pharmaceutical | Derivados sustituidos de pirazol y su uso |
| AU2011212813B2 (en) | 2010-02-04 | 2014-10-23 | Radius Health, Inc. | Selective androgen receptor modulators |
| HUE030072T2 (en) | 2010-05-12 | 2017-04-28 | Radius Health Inc | Therapeutic prescriptions |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| US9133182B2 (en) | 2010-09-28 | 2015-09-15 | Radius Health, Inc. | Selective androgen receptor modulators |
| EP2834216A1 (en) * | 2012-04-04 | 2015-02-11 | Catylix Inc. | Selective androgen receptor modulators |
| EP3158995B1 (en) | 2012-08-09 | 2018-05-23 | Dynamis Therapeutics, Inc. | Meglumine for reducing high triglyceride levels |
| KR102069008B1 (ko) * | 2012-09-21 | 2020-02-11 | 메르크 파텐트 게엠베하 | C-c 삼중 결합을 갖는 화합물 및 액정 혼합물에서 이의 용도 |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| ES3055185T3 (en) | 2014-03-28 | 2026-02-10 | Univ Duke | Treatment of an estrogen receptor positive breast cancer using a selective estrogen receptor modulator |
| KR101597327B1 (ko) * | 2014-04-24 | 2016-02-24 | 동아에스티 주식회사 | 옥사졸리딘계 화합물 및 이를 포함하는 선택적 안드로겐 수용체 효능제 |
| CN103951688B (zh) * | 2014-05-06 | 2016-04-20 | 成都安斯利生物医药有限公司 | 一种制备3,5-二氟-4-甲基苯硼酸的方法 |
| MX389702B (es) | 2016-06-22 | 2025-03-20 | Ellipses Pharma Ltd | Compuestos para usarse en el tratamiento de cancer de mama que expresa el receptor de androgenos (ar+). |
| JP7481115B2 (ja) | 2017-01-05 | 2024-05-10 | 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の多形性形態 |
| MX2020013713A (es) | 2018-07-04 | 2021-03-02 | Radius Pharmaceuticals Inc | Formas polimorficas de rad1901-2hcl. |
| BR112021013557A2 (pt) | 2019-01-11 | 2021-09-21 | Grünenthal GmbH | Amidas de pirrolidina substituídas iii |
| EP3924328A1 (en) | 2019-02-12 | 2021-12-22 | Radius Pharmaceuticals, Inc. | Processes and compounds |
| CN110204505B (zh) * | 2019-05-31 | 2023-02-03 | 荆门医药工业技术研究院 | (s)-3-苄氧羰基-4-异丙基-2,5-恶唑烷二酮的制备工艺 |
| US20230012570A1 (en) * | 2019-11-20 | 2023-01-19 | Medshine Discovery Inc. | Bicyclic compound used as selective androgen receptor modulator |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002088073A (ja) * | 2000-09-08 | 2002-03-27 | Yamanouchi Pharmaceut Co Ltd | 抗アンドロゲン剤 |
| WO2005090282A1 (en) * | 2004-03-12 | 2005-09-29 | Ligand Pharmaceuticals Incorporated | Androgen receptor modulator compounds and methods |
| WO2005108351A1 (en) * | 2004-05-11 | 2005-11-17 | Pfizer Products Inc. | Benzonitrile derivatives to treat musculoskeletal frailty |
| WO2006117677A1 (en) * | 2005-05-05 | 2006-11-09 | Warner-Lambert Company Llc | Androgen modulators |
| WO2008011072A2 (en) * | 2006-07-19 | 2008-01-24 | Osurf (Ohio State University Research Foundation) | Selective androgen receptor modulators, analogs and derivatives thereof and uses thereof |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4141399A1 (de) | 1991-12-16 | 1993-06-17 | Bayer Ag | 4-(substituierte)amino-3-arylpyrrolinon-derivate |
| CN1129581C (zh) * | 1998-09-22 | 2003-12-03 | 山之内制药株式会社 | 氰基苯基衍生物 |
| US6258833B1 (en) | 1999-12-23 | 2001-07-10 | Icos Corporation | Cyclic AMP-specific phosphodiesterase inhibitors |
| US7026500B2 (en) | 2000-08-24 | 2006-04-11 | University Of Tennessee Research Foundation | Halogenated selective androgen receptor modulators and methods of use thereof |
| FR2817472B1 (fr) | 2000-12-06 | 2003-01-03 | Oreal | Composition de teinture d'oxydation a base de 1-(4-aminophenyl)pyrrolidines substituees au moins en position 2 et 3 et procede de teinture de mise en oeuvre |
| DK1463497T3 (da) | 2001-12-06 | 2012-01-30 | Gtx Inc | Behandling af muskelsvind med selektive androgenreceptormodulatorer |
| JP4316232B2 (ja) | 2001-12-28 | 2009-08-19 | 武田薬品工業株式会社 | アンドロゲン受容体拮抗剤 |
| AU2002367424A1 (en) * | 2001-12-28 | 2003-07-24 | Takeda Chemical Industries, Ltd. | Androgen receptor antagonists |
| JP2005529952A (ja) | 2002-06-17 | 2005-10-06 | ユニバーシティ・オブ・テネシー・リサーチ・ファウンデーション | Ｎ架橋選択的アンドロゲン受容体修飾物質及びその使用方法 |
| PL375042A1 (en) | 2002-08-12 | 2005-11-14 | Takeda Pharmaceutical Company Limited | Fused benzene derivative and use |
| GB0402492D0 (en) | 2004-02-04 | 2004-03-10 | Pfizer Ltd | Pharmaceutically active compounds |
| EP1756101A2 (en) | 2004-05-17 | 2007-02-28 | Acadia Pharmaceuticals Inc. | Androgen receptor modulators and method of treating disease using the same |
| PL1753417T3 (pl) | 2004-06-07 | 2012-09-28 | Univ Tennessee Res Found | Selektywny modulator receptora androgenowego i jego zastosowania medyczne |
| CN101119993B (zh) | 2005-01-10 | 2015-03-04 | 阿卡蒂亚药品公司 | 作为选择性雄激素受体调节剂的氨基苯基衍生物 |
| PL1891038T3 (pl) | 2005-05-13 | 2009-04-30 | Lilly Co Eli | Podstawione n-arylopirolidyny jako selektywne modulatory receptora androgenowego |
| JP5070054B2 (ja) | 2005-08-01 | 2012-11-07 | 武田薬品工業株式会社 | 環状アミン化合物 |
| US20090042857A1 (en) * | 2006-02-20 | 2009-02-12 | Masuo Yamaoka | Novel Pharmaceutical |
| KR20090034395A (ko) * | 2006-07-26 | 2009-04-07 | 노파르티스 아게 | 운데카프레닐 피로포스페이트 합성효소의 억제제 |
| JP5241507B2 (ja) | 2006-11-30 | 2013-07-17 | 武田薬品工業株式会社 | 環状アミン化合物 |
| ME01579B (me) * | 2007-08-07 | 2014-09-20 | Takeda Pharmaceuticals Co | Derivati pirolidin-2-ona kao modulatori androgenskih receptora |
-
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- 2008-08-06 ME MEP-2013-64A patent/ME01579B/me unknown
- 2008-08-06 SI SI200830941T patent/SI2176220T1/sl unknown
- 2008-08-06 WO PCT/JP2008/064500 patent/WO2009020234A2/en not_active Ceased
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- 2008-08-06 CA CA2695852A patent/CA2695852C/en active Active
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-
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- 2010-03-05 CO CO10026475A patent/CO6160326A2/es unknown
-
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- 2013-06-21 CY CY20131100507T patent/CY1114067T1/el unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002088073A (ja) * | 2000-09-08 | 2002-03-27 | Yamanouchi Pharmaceut Co Ltd | 抗アンドロゲン剤 |
| WO2005090282A1 (en) * | 2004-03-12 | 2005-09-29 | Ligand Pharmaceuticals Incorporated | Androgen receptor modulator compounds and methods |
| WO2005108351A1 (en) * | 2004-05-11 | 2005-11-17 | Pfizer Products Inc. | Benzonitrile derivatives to treat musculoskeletal frailty |
| WO2006117677A1 (en) * | 2005-05-05 | 2006-11-09 | Warner-Lambert Company Llc | Androgen modulators |
| WO2008011072A2 (en) * | 2006-07-19 | 2008-01-24 | Osurf (Ohio State University Research Foundation) | Selective androgen receptor modulators, analogs and derivatives thereof and uses thereof |
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