JP2005525337A5 - - Google Patents
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- JP2005525337A5 JP2005525337A5 JP2003567399A JP2003567399A JP2005525337A5 JP 2005525337 A5 JP2005525337 A5 JP 2005525337A5 JP 2003567399 A JP2003567399 A JP 2003567399A JP 2003567399 A JP2003567399 A JP 2003567399A JP 2005525337 A5 JP2005525337 A5 JP 2005525337A5
- Authority
- JP
- Japan
- Prior art keywords
- inhibitor
- pharmaceutical composition
- alkyl
- reductase
- group
- 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.)
- Withdrawn
Links
- 239000003112 inhibitor Substances 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 108010070743 3(or 17)-beta-hydroxysteroid dehydrogenase Proteins 0.000 claims description 6
- 101000800383 Arabidopsis thaliana Xanthoxin dehydrogenase Proteins 0.000 claims description 6
- 102100034067 Dehydrogenase/reductase SDR family member 11 Human genes 0.000 claims description 6
- 210000002307 prostate Anatomy 0.000 claims description 6
- 230000002280 anti-androgenic effect Effects 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- -1 sulfamic Chemical group 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 5
- 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 claims 4
- WPBXOELOQKLBDF-UHFFFAOYSA-N cyanogen iodide Chemical compound IC#N WPBXOELOQKLBDF-UHFFFAOYSA-N 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- FAQOZARUOBFXBH-UHFFFAOYSA-N nitroformamide Chemical compound NC(=O)[N+]([O-])=O FAQOZARUOBFXBH-UHFFFAOYSA-N 0.000 claims 2
- BTHYQSCYAWQGHC-UHFFFAOYSA-N 2-chloro-4-(2,4-difluorophenyl)benzonitrile Chemical compound FC1=CC(F)=CC=C1C1=CC=C(C#N)C(Cl)=C1 BTHYQSCYAWQGHC-UHFFFAOYSA-N 0.000 claims 1
- JVLVYIRWZGBIPV-UHFFFAOYSA-N 2-chloro-4-(2,6-difluorophenyl)benzonitrile Chemical compound FC1=CC=CC(F)=C1C1=CC=C(C#N)C(Cl)=C1 JVLVYIRWZGBIPV-UHFFFAOYSA-N 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- 206010020112 Hirsutism Diseases 0.000 claims 1
- 206010039792 Seborrhoea Diseases 0.000 claims 1
- ZIHQUWYJSTVYAT-UHFFFAOYSA-N [NH-][N+]([O-])=O Chemical compound [NH-][N+]([O-])=O ZIHQUWYJSTVYAT-UHFFFAOYSA-N 0.000 claims 1
- 206010000496 acne Diseases 0.000 claims 1
- 201000002996 androgenic alopecia Diseases 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 208000008742 seborrheic dermatitis Diseases 0.000 claims 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 3
- 239000000051 antiandrogen Substances 0.000 description 3
- 238000002648 combination therapy Methods 0.000 description 3
- 210000004907 gland Anatomy 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OFUGESGXTBBDMB-UHFFFAOYSA-N 2-[4-cyano-3-(trifluoromethyl)phenyl]-5-fluorobenzamide Chemical compound NC(=O)C1=CC(F)=CC=C1C1=CC=C(C#N)C(C(F)(F)F)=C1 OFUGESGXTBBDMB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- ADJBXDCXYMCCAD-UHFFFAOYSA-N (4-fluoro-2-methoxyphenyl)boronic acid Chemical compound COC1=CC(F)=CC=C1B(O)O ADJBXDCXYMCCAD-UHFFFAOYSA-N 0.000 description 1
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 1
- 108010029908 3-oxo-5-alpha-steroid 4-dehydrogenase Proteins 0.000 description 1
- 102000001779 3-oxo-5-alpha-steroid 4-dehydrogenase Human genes 0.000 description 1
- FICSINKSXAWTPE-UHFFFAOYSA-N 4-(4-fluoro-2-methoxyphenyl)-2-(trifluoromethyl)benzonitrile Chemical compound COC1=CC(F)=CC=C1C1=CC=C(C#N)C(C(F)(F)F)=C1 FICSINKSXAWTPE-UHFFFAOYSA-N 0.000 description 1
- XZZVLHLYHDELAI-UHFFFAOYSA-N 4-bromo-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(Br)=CC=C1C#N XZZVLHLYHDELAI-UHFFFAOYSA-N 0.000 description 1
- 229940113178 5 Alpha reductase inhibitor Drugs 0.000 description 1
- 239000002677 5-alpha reductase inhibitor Substances 0.000 description 1
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229940124139 Hydroxysteroid dehydrogenase inhibitor Drugs 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229960003473 androstanolone Drugs 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229940117382 propecia Drugs 0.000 description 1
- 229940072254 proscar Drugs 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35778502P | 2002-02-15 | 2002-02-15 | |
| PCT/CA2003/000208 WO2003068217A1 (en) | 2002-02-15 | 2003-02-14 | Biphenil derivatives and their use as antiandrogenic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005525337A JP2005525337A (ja) | 2005-08-25 |
| JP2005525337A5 true JP2005525337A5 (enExample) | 2006-01-05 |
Family
ID=27734763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003567399A Withdrawn JP2005525337A (ja) | 2002-02-15 | 2003-02-14 | ビフェニル誘導体およびその抗アンドロゲン薬としての使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6933321B2 (enExample) |
| EP (1) | EP1474127B1 (enExample) |
| JP (1) | JP2005525337A (enExample) |
| CN (1) | CN1633287A (enExample) |
| AT (1) | ATE345125T1 (enExample) |
| AU (1) | AU2003205461B2 (enExample) |
| CA (1) | CA2474171A1 (enExample) |
| DE (1) | DE60309667D1 (enExample) |
| MX (1) | MXPA04007870A (enExample) |
| WO (1) | WO2003068217A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101536701B1 (ko) | 2004-01-07 | 2015-07-14 | 앙도르쉐르슈 인코포레이티드 | 헬릭스 12 배향형 스테로이드계 약학 제품 |
| JP3997255B2 (ja) | 2004-02-13 | 2007-10-24 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | アンドロゲンレセプターモジュレーター |
| BRPI0509759A (pt) | 2004-04-13 | 2007-10-16 | Warner Lambert Co | moduladores de androgênio |
| CA2562672C (en) | 2004-04-22 | 2009-09-29 | Warner-Lambert Company Llc | 4-cyano-phenoxy derivatives as androgen modulators |
| MXPA06015169A (es) * | 2004-07-08 | 2007-08-21 | Warner Lambert Co | Moduladores de androgenos. |
| US20090105349A1 (en) * | 2004-08-18 | 2009-04-23 | Warner-Lambert Company Llc | Androgen modulators |
| EP1781599A1 (en) * | 2004-08-18 | 2007-05-09 | Warner-Lambert Company LLC | Androgen modulators |
| TW200724139A (en) | 2005-05-05 | 2007-07-01 | Warner Lambert Co | Androgen modulators |
| US7709516B2 (en) | 2005-06-17 | 2010-05-04 | Endorecherche, Inc. | Helix 12 directed non-steroidal antiandrogens |
| WO2007007149A1 (en) * | 2005-07-12 | 2007-01-18 | Warner-Lambert Company Llc | Androgen modulators |
| US20090170886A1 (en) * | 2005-08-08 | 2009-07-02 | Pfizer Inc | Androgen modulators |
| EP2013176A2 (en) * | 2006-02-27 | 2009-01-14 | Sterix Limited | Diaryl compounds as non-steroidal inhibitors of 17-beta hydroxysteroid dehydrogenase and/or steroid sulphatase for the treatment of oestrogen-related diseases such as hormone dependent breast cancer |
| US8067448B2 (en) | 2008-02-22 | 2011-11-29 | Radius Health, Inc. | Selective androgen receptor modulators |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | 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 |
| AU2011312490B2 (en) | 2010-09-28 | 2015-06-25 | Radius Pharmaceuticals, Inc. | Selective androgen receptor modulators |
| WO2012117097A1 (en) * | 2011-03-03 | 2012-09-07 | Universität des Saarlandes | Biaryl derivatives as selective 17beta-hydroxysteroid dehydrogenase type 2 inhibitors |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| PT3122426T (pt) | 2014-03-28 | 2023-02-28 | Univ Duke | Tratamento de cancro da mama utilizando moduladores seletivos do recetor de estrogénio |
| JP6529286B2 (ja) * | 2015-03-09 | 2019-06-12 | 株式会社カネカ | 発光材料および有機ｅｌ素子 |
| HRP20220619T1 (hr) | 2016-06-22 | 2023-02-03 | Ellipses Pharma Ltd | Postupci za liječenje ar+ raka dojke |
| ES2981967T3 (es) | 2017-01-05 | 2024-10-14 | Radius Pharmaceuticals Inc | Formas polimórficas de RAD1901-2HCl |
| 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 |
| CN112961041B (zh) * | 2021-01-25 | 2022-06-21 | 心远(广州)药物研究有限公司 | 儿茶酚类化合物及其制备方法和应用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3281280A (en) * | 1963-10-28 | 1966-10-25 | Union Carbide Corp | Corrosion inhibitors |
| US3797494A (en) | 1969-04-01 | 1974-03-19 | Alza Corp | Bandage for the administration of drug by controlled metering through microporous materials |
| US3742951A (en) | 1971-08-09 | 1973-07-03 | Alza Corp | Bandage for controlled release of vasodilators |
| DE2832112C2 (de) * | 1978-07-21 | 1985-06-05 | Merck Patent Gmbh, 6100 Darmstadt | Flüssigkristallines Dielektrikum |
| DE3247215A1 (de) * | 1982-12-18 | 1984-06-20 | Riedel-De Haen Ag, 3016 Seelze | Fluorhaltige biphenylverbindung und verfahren zu ihrer herstellung |
| DE3333240A1 (de) | 1983-09-12 | 1985-03-28 | Schering AG, 1000 Berlin und 4709 Bergkamen | Mittel zur transdermalen applikation von arzneimittelwirkstoffen |
| US4568343A (en) | 1984-10-09 | 1986-02-04 | Alza Corporation | Skin permeation enhancer compositions |
| US4816258A (en) | 1987-02-26 | 1989-03-28 | Alza Corporation | Transdermal contraceptive formulations |
| US5064654A (en) | 1989-01-11 | 1991-11-12 | Ciba-Geigy Corporation | Mixed solvent mutually enhanced transdermal therapeutic system |
| GB8928282D0 (en) * | 1989-12-14 | 1990-02-21 | Secr Defence | Pdlc materials |
| US5071644A (en) | 1990-08-07 | 1991-12-10 | Mediventures, Inc. | Topical drug delivery with thermo-irreversible gels |
| US6060503A (en) | 1991-12-02 | 2000-05-09 | Endorecherche, Inc. | Benzopyran-containing compounds and method for their use |
| JPH05273771A (ja) * | 1992-03-27 | 1993-10-22 | Kao Corp | 電子写真感光体 |
| JPH08501100A (ja) | 1992-09-09 | 1996-02-06 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 除草性ベンゼン化合物 |
| CA2161544A1 (en) * | 1993-04-27 | 1994-11-10 | Simon Teanby Hodgson | Cyclooxygenase and 5-lipoxygenase inhibiting n(3-biphenylyl- 1(s)-methyl-2-propenyl) acetohydroxamic acid derivatives |
| DE4423061C1 (de) * | 1994-07-01 | 1996-01-18 | Hoechst Ag | Verfahren zur Herstellung von Biphenylen mit Palladacyclen als Katalysatoren |
| FR2737721B1 (fr) * | 1995-08-08 | 1997-09-05 | Roussel Uclaf | Nouveaux composes biphenyles, leur procede de preparation et les intermediaires de ce procede, leur application a titre de medicament et les compositions pharmaceutiques les contenant |
| DE19607135C1 (de) * | 1996-02-26 | 1997-04-24 | Great Lakes Chem Konstanz Gmbh | Verfahren zur Herstellung von unsymmetrisch substituierten Biphenylen |
| AU3536699A (en) * | 1998-04-27 | 1999-11-16 | Ihara Chemical Industry Co. Ltd. | 3-arylphenyl sulfide derivatives and insecticides and miticides |
| JP2000001431A (ja) | 1998-06-15 | 2000-01-07 | Kotobuki Seiyaku Kk | 尿酸排泄剤 |
| DE10014645A1 (de) * | 2000-03-24 | 2001-09-27 | Merck Patent Gmbh | Substituierte Biphenylderivate |
-
2003
- 2003-02-14 US US10/369,267 patent/US6933321B2/en not_active Expired - Fee Related
- 2003-02-14 AT AT03702233T patent/ATE345125T1/de not_active IP Right Cessation
- 2003-02-14 AU AU2003205461A patent/AU2003205461B2/en not_active Ceased
- 2003-02-14 DE DE60309667T patent/DE60309667D1/de not_active Expired - Lifetime
- 2003-02-14 MX MXPA04007870A patent/MXPA04007870A/es not_active Application Discontinuation
- 2003-02-14 CA CA002474171A patent/CA2474171A1/en not_active Abandoned
- 2003-02-14 EP EP03702233A patent/EP1474127B1/en not_active Expired - Lifetime
- 2003-02-14 JP JP2003567399A patent/JP2005525337A/ja not_active Withdrawn
- 2003-02-14 CN CNA038039729A patent/CN1633287A/zh active Pending
- 2003-02-14 WO PCT/CA2003/000208 patent/WO2003068217A1/en not_active Ceased
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