JP2008520665A5 - - Google Patents
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- Publication number
- JP2008520665A5 JP2008520665A5 JP2007543066A JP2007543066A JP2008520665A5 JP 2008520665 A5 JP2008520665 A5 JP 2008520665A5 JP 2007543066 A JP2007543066 A JP 2007543066A JP 2007543066 A JP2007543066 A JP 2007543066A JP 2008520665 A5 JP2008520665 A5 JP 2008520665A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- hydrogen
- phenyl
- methyl
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 235
- 229910052739 hydrogen Inorganic materials 0.000 claims 112
- 239000001257 hydrogen Substances 0.000 claims 112
- -1 cyano, nitro, amino Chemical group 0.000 claims 85
- 150000002431 hydrogen Chemical class 0.000 claims 72
- 125000004093 cyano group Chemical group *C#N 0.000 claims 38
- 229910052736 halogen Inorganic materials 0.000 claims 38
- 150000002367 halogens Chemical class 0.000 claims 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 37
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 23
- 125000003545 alkoxy group Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 13
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 12
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 11
- 239000000203 mixture Substances 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 125000003282 alkyl amino group Chemical group 0.000 claims 9
- 102000001307 androgen receptors Human genes 0.000 claims 9
- 108010080146 androgen receptors Proteins 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 9
- 230000001404 mediated effect Effects 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 208000030507 AIDS Diseases 0.000 claims 6
- 208000002874 Acne Vulgaris Diseases 0.000 claims 6
- 201000004384 Alopecia Diseases 0.000 claims 6
- 206010006187 Breast cancer Diseases 0.000 claims 6
- 208000026310 Breast neoplasm Diseases 0.000 claims 6
- 206010006895 Cachexia Diseases 0.000 claims 6
- 206010020112 Hirsutism Diseases 0.000 claims 6
- 206010060862 Prostate cancer Diseases 0.000 claims 6
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 6
- 206010000496 acne Diseases 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 6
- 231100000360 alopecia Toxicity 0.000 claims 6
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 208000022531 anorexia Diseases 0.000 claims 5
- 206010061428 decreased appetite Diseases 0.000 claims 5
- 238000009472 formulation Methods 0.000 claims 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- RYBKPGYFXRNMMU-GFCCVEGCSA-N (5r)-n-[4-cyano-3-(trifluoromethyl)phenyl]-5-methyl-3-(trifluoromethyl)-1,4-dihydropyrazole-5-carboxamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)[C@@]1(C)CC(C(F)(F)F)=NN1 RYBKPGYFXRNMMU-GFCCVEGCSA-N 0.000 claims 1
- RYBKPGYFXRNMMU-LBPRGKRZSA-N (5s)-n-[4-cyano-3-(trifluoromethyl)phenyl]-5-methyl-3-(trifluoromethyl)-1,4-dihydropyrazole-5-carboxamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)[C@]1(C)CC(C(F)(F)F)=NN1 RYBKPGYFXRNMMU-LBPRGKRZSA-N 0.000 claims 1
- FPUAWRPFLJJPKB-UHFFFAOYSA-N 3-(4-acetamidophenyl)-5-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]-1,4-dihydropyrazole-5-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NNC(C)(C(=O)NC=2C=C(C(=CC=2)[N+]([O-])=O)C(F)(F)F)C1 FPUAWRPFLJJPKB-UHFFFAOYSA-N 0.000 claims 1
- GNIPHYAQVFFVFB-UHFFFAOYSA-N 3-(4-acetamidophenyl)-n-[4-cyano-3-(trifluoromethyl)phenyl]-5-methyl-1,4-dihydropyrazole-5-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NNC(C)(C(=O)NC=2C=C(C(C#N)=CC=2)C(F)(F)F)C1 GNIPHYAQVFFVFB-UHFFFAOYSA-N 0.000 claims 1
- FZVBSNLCPFQYET-UHFFFAOYSA-N 5-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]-3-[4-[(2,2,2-trifluoroacetyl)amino]phenyl]-1,4-dihydropyrazole-5-carboxamide Chemical compound N=1NC(C)(C(=O)NC=2C=C(C(=CC=2)[N+]([O-])=O)C(F)(F)F)CC=1C1=CC=C(NC(=O)C(F)(F)F)C=C1 FZVBSNLCPFQYET-UHFFFAOYSA-N 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- DLPFHGUGJWOGOG-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-5-ethyl-3-(trifluoromethyl)-1,4-dihydropyrazole-5-carboxamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C1(CC)CC(C(F)(F)F)=NN1 DLPFHGUGJWOGOG-UHFFFAOYSA-N 0.000 claims 1
- RYBKPGYFXRNMMU-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-5-methyl-3-(trifluoromethyl)-1,4-dihydropyrazole-5-carboxamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C1(C)CC(C(F)(F)F)=NN1 RYBKPGYFXRNMMU-UHFFFAOYSA-N 0.000 claims 1
- GQIZGAPVUDOSCA-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-n'-ethyl-5-methyl-3-(trifluoromethyl)-1,4-dihydropyrazole-5-carboximidamide Chemical compound C1C(C(F)(F)F)=NNC1(C)C(/NCC)=N/C1=CC=C(C#N)C(C(F)(F)F)=C1 GQIZGAPVUDOSCA-UHFFFAOYSA-N 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 1
- 0 *C1=NN(*)CC1 Chemical compound *C1=NN(*)CC1 0.000 description 11
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62833704P | 2004-11-16 | 2004-11-16 | |
| US60/628,337 | 2004-11-16 | ||
| PCT/US2005/038292 WO2006055184A2 (en) | 2004-11-16 | 2005-10-25 | Novel heterocycle derivatives useful as selective androgen receptor modulators (sarms) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008520665A JP2008520665A (ja) | 2008-06-19 |
| JP2008520665A5 true JP2008520665A5 (https=) | 2008-12-25 |
| JP4969451B2 JP4969451B2 (ja) | 2012-07-04 |
Family
ID=36218098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007543066A Expired - Lifetime JP4969451B2 (ja) | 2004-11-16 | 2005-10-25 | 選択的アンドロゲン受容体モジュレーター（ｓａｒｍ）として有用な新規な複素環誘導体 |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US7465809B2 (https=) |
| EP (1) | EP1817292B1 (https=) |
| JP (1) | JP4969451B2 (https=) |
| CN (2) | CN104803916B (https=) |
| AR (1) | AR051958A1 (https=) |
| AU (1) | AU2005307003B2 (https=) |
| CA (1) | CA2587678C (https=) |
| MY (1) | MY142048A (https=) |
| TW (1) | TWI483725B (https=) |
| WO (1) | WO2006055184A2 (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7655683B2 (en) * | 2006-02-10 | 2010-02-02 | Janssen Pharmaceutica Nv | Imidazolopyrazole derivatives useful as selective androgen receptor modulators |
| 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 |
| ES2488990T3 (es) | 2008-02-22 | 2014-09-01 | Radius Health, Inc. | Moduladores selectivos del receptor de andrógenos |
| MX338831B (es) | 2010-02-04 | 2016-05-03 | Radius Health Inc | Moduladores selectivos de receptores de androgenos. |
| EP2568806B1 (en) | 2010-05-12 | 2016-05-11 | Radius Health, Inc. | Therapeutic regimens |
| 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 |
| US9133182B2 (en) | 2010-09-28 | 2015-09-15 | Radius Health, Inc. | Selective androgen receptor modulators |
| FI3834824T3 (fi) | 2014-03-28 | 2025-12-05 | Univ Duke | Estrogeenireseptoripositiivisen rintasyövän hoito selektiivisellä estrogeenireseptorin modulaattorilla |
| 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 |
| LT3474841T (lt) | 2016-06-22 | 2022-06-10 | Ellipses Pharma Ltd | Ar+ krūties vėžio gydymo būdai |
| 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 |
| KR102707399B1 (ko) | 2017-01-05 | 2024-09-13 | 래디어스 파마슈티컬스, 인코포레이티드 | Rad1901-2hcl의 다형 형태 |
| EP3601255A1 (en) | 2017-03-21 | 2020-02-05 | AbbVie Deutschland GmbH & Co. KG | Proline amide compounds and their azetidine analogues carrying a specifically substituted benzyl radical |
| WO2019222272A1 (en) | 2018-05-14 | 2019-11-21 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| IL279853B2 (en) | 2018-07-04 | 2025-01-01 | Radius Pharmaceuticals Inc | Polymorphic forms of RAD 1901-2HCL |
| CN113348163B (zh) | 2019-02-12 | 2024-10-08 | 雷迪厄斯制药公司 | 方法和化合物 |
| 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 |
| EP4015501A1 (en) * | 2020-12-16 | 2022-06-22 | Consejo Superior de Investigaciones Científicas (CSIC) | N-benzyl-alpha-aminoamides as anaphase-promoting complex/cyclosome (apc/c) inhibitors |
| 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 |
| 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 |
Family Cites Families (11)
| 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 |
| US6339099B1 (en) | 1997-06-20 | 2002-01-15 | Dupont Pharmaceuticals Company | Guanidine mimics as factor Xa inhibitors |
| JP2002527438A (ja) | 1998-10-09 | 2002-08-27 | 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 | ４，５−ジヒドロ−イソオキサゾール誘導体及びそれらの製薬学的使用 |
| US6472415B1 (en) * | 1998-12-18 | 2002-10-29 | Biophysica, Inc. | Androgen receptor suppressors in the therapy and diagnosis of prostate cancer, alopecia and other hyper-androgenic syndromes |
| WO2002000651A2 (en) | 2000-06-27 | 2002-01-03 | Bristol-Myers Squibb Pharma Company | Factor xa inhibitors |
| US7026484B2 (en) * | 2001-02-23 | 2006-04-11 | Ligand Pharmaceuticals Incorporated | Tricyclic androgen receptor modulator compounds and methods |
| US6738540B2 (en) * | 2001-06-22 | 2004-05-18 | Lucent Technologies Inc. | Optical cross-connect switch using programmable multiplexers/demultiplexers |
| US6657770B2 (en) * | 2001-06-22 | 2003-12-02 | Lucent Technologies Inc. | Programmable optical multiplexer/demultiplexer |
| US7030141B2 (en) * | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| CN1835937B (zh) | 2003-06-13 | 2012-07-18 | 詹森药业有限公司 | 作为选择性雄激素受体调节剂(sarms)的噻唑啉衍生物 |
| EP1791821B1 (en) | 2004-09-10 | 2013-06-05 | Janssen Pharmaceutica NV | Novel imidazolidin-2-one derivatives as selective androgen receptor modulators (sarms) |
-
2005
- 2005-10-25 CN CN201510087784.0A patent/CN104803916B/zh not_active Expired - Fee Related
- 2005-10-25 CN CNA2005800466829A patent/CN101103003A/zh active Pending
- 2005-10-25 US US11/258,448 patent/US7465809B2/en not_active Expired - Lifetime
- 2005-10-25 WO PCT/US2005/038292 patent/WO2006055184A2/en not_active Ceased
- 2005-10-25 AU AU2005307003A patent/AU2005307003B2/en not_active Ceased
- 2005-10-25 JP JP2007543066A patent/JP4969451B2/ja not_active Expired - Lifetime
- 2005-10-25 CA CA2587678A patent/CA2587678C/en not_active Expired - Fee Related
- 2005-10-25 EP EP05815801.5A patent/EP1817292B1/en not_active Expired - Lifetime
- 2005-11-14 MY MYPI20055325A patent/MY142048A/en unknown
- 2005-11-15 AR ARP050104794A patent/AR051958A1/es not_active Application Discontinuation
- 2005-11-15 TW TW094140006A patent/TWI483725B/zh not_active IP Right Cessation
-
2008
- 2008-05-27 US US12/127,388 patent/US7781473B2/en not_active Expired - Fee Related
-
2010
- 2010-07-06 US US12/830,733 patent/US8088811B2/en not_active Expired - Fee Related
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