AU729325B2 - Steroid sulfatase inhibitors and methods for making and using the same - Google Patents
Steroid sulfatase inhibitors and methods for making and using the same Download PDFInfo
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- AU729325B2 AU729325B2 AU85687/98A AU8568798A AU729325B2 AU 729325 B2 AU729325 B2 AU 729325B2 AU 85687/98 A AU85687/98 A AU 85687/98A AU 8568798 A AU8568798 A AU 8568798A AU 729325 B2 AU729325 B2 AU 729325B2
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- 238000000034 method Methods 0.000 title claims abstract description 45
- 229940123142 Steroid sulfatase inhibitor Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
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- 229940011871 estrogen Drugs 0.000 claims abstract description 22
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- 238000011282 treatment Methods 0.000 claims abstract description 10
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- 239000000203 mixture Substances 0.000 claims description 18
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 13
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 201000002595 endometriosis of ovary Diseases 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- VDDXQSUSMHZCLS-UHFFFAOYSA-N ethenyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC=C VDDXQSUSMHZCLS-UHFFFAOYSA-N 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 230000006993 memory improvement Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 210000001589 microsome Anatomy 0.000 description 1
- YRCHYHRCBXNYNU-UHFFFAOYSA-N n-[[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]carbamothioyl]-2-(4-fluorophenyl)acetamide Chemical compound N1=CC(CNCCOC)=CC=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=S)NC(=O)CC=4C=CC(F)=CC=4)=CC=3)F)=C2S1 YRCHYHRCBXNYNU-UHFFFAOYSA-N 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 208000030747 ovarian endometriosis Diseases 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 206010046885 vaginal cancer Diseases 0.000 description 1
- 208000013139 vaginal neoplasm Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
-
- 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
- A61P5/32—Antioestrogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0072—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the A ring of the steroid being aromatic
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/897,247 US5880115A (en) | 1997-07-18 | 1997-07-18 | Steroid sulfatase inhibitors and methods for making and using the same |
| US08/897247 | 1997-07-18 | ||
| PCT/US1998/014206 WO1999003876A1 (en) | 1997-07-18 | 1998-07-08 | Steroid sulfatase inhibitors and methods for making and using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU8568798A AU8568798A (en) | 1999-02-10 |
| AU729325B2 true AU729325B2 (en) | 2001-02-01 |
Family
ID=25407613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU85687/98A Ceased AU729325B2 (en) | 1997-07-18 | 1998-07-08 | Steroid sulfatase inhibitors and methods for making and using the same |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5880115A (https=) |
| EP (1) | EP1009755B1 (https=) |
| JP (1) | JP2001510200A (https=) |
| AT (1) | ATE250077T1 (https=) |
| AU (1) | AU729325B2 (https=) |
| CA (1) | CA2296498A1 (https=) |
| DE (1) | DE69818278T2 (https=) |
| WO (1) | WO1999003876A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6011024A (en) | 1991-08-28 | 2000-01-04 | Imperial College Of Science Technology & Medicine | Steroid sulphatase inhibitors |
| US6476011B1 (en) * | 1991-08-28 | 2002-11-05 | Sterix Limited | Methods for introducing an estrogenic compound |
| GB9118478D0 (en) * | 1991-08-29 | 1991-10-16 | Imperial College | Steroid sulphatase inhibitors |
| US6288050B1 (en) * | 1997-07-18 | 2001-09-11 | Duquesne University Of The Holy Ghost | Steroid sulfatase inhibitors and methods for making and using the same |
| US6376687B1 (en) * | 1997-07-18 | 2002-04-23 | Duquesne University Of The Holy Ghost | Steroid sulfatase inhibitors and methods for making and using the same |
| ES2347027T3 (es) | 1998-05-22 | 2010-10-22 | The Board Of Trustees Of The Leland Stanford Junior University | Moleculas bifuncionales y terapias basadas en las mismas. |
| ATE401896T1 (de) | 1998-06-10 | 2008-08-15 | Sterix Ltd | Pharmazeutische zusammensetzungen mit tumor nekrose faktor und 2-methoxyestron-3-o-sulphamat als estrone sulphatasehemmern |
| US6248780B1 (en) | 1998-10-01 | 2001-06-19 | Duquesne University Of The Holy Ghost | Compounds for the treatment of estrogen-dependent illnesses and methods for making and using the same |
| JP2000309599A (ja) | 1999-04-13 | 2000-11-07 | Kyowa Hakko Kogyo Co Ltd | エストラ−１，３，５（１０），１６−テトラエン誘導体 |
| AU783910B2 (en) | 1999-04-30 | 2005-12-22 | Sterix Limited | Use of estrone derivatives as antitumour agents |
| US7078395B1 (en) | 1999-06-16 | 2006-07-18 | Sterix Limited | Methods for treating or preventing cancer by preventing, inhibiting or arresting cell cycling |
| US7335650B2 (en) * | 2000-01-14 | 2008-02-26 | Sterix Limited | Composition |
| US6953785B2 (en) * | 2000-04-24 | 2005-10-11 | Kyowa Hakko Kogyo Co., Ltd. | Estra-1,3,5(10)-triene derivatives |
| GB0025788D0 (en) * | 2000-10-20 | 2000-12-06 | Sterix Ltd | Use |
| WO2002043704A1 (fr) | 2000-12-01 | 2002-06-06 | Kyowa Hakko Kogyo Co., Ltd. | Composition a solubilite ou absorbabilite orale amelioree |
| JP4202250B2 (ja) | 2001-07-25 | 2008-12-24 | バイオマリン ファーマシューティカル インコーポレイテッド | 血液脳関門輸送を調節するための組成物および方法 |
| US8026229B2 (en) * | 2001-08-13 | 2011-09-27 | Sterix Limited | Antitumor-active 2-alkoxyestradiol sulfamates |
| GB0306718D0 (en) * | 2003-03-24 | 2003-04-30 | Sterix Ltd | Compound |
| EP2671507A3 (en) | 2005-04-28 | 2014-02-19 | Proteus Digital Health, Inc. | Pharma-informatics system |
| US9062126B2 (en) | 2005-09-16 | 2015-06-23 | Raptor Pharmaceuticals Inc. | Compositions comprising receptor-associated protein (RAP) variants specific for CR-containing proteins and uses thereof |
| CA2752373C (en) | 2009-02-20 | 2017-10-10 | To-Bbb Holding B.V. | Glutathione-based drug delivery system |
| IL255113B (en) | 2009-05-06 | 2022-09-01 | Laboratory Skin Care Inc | Dermal delivery compositions comprising active agent-calcium phosphate particle complexes and methods of using the same |
| CN111647037B (zh) * | 2020-06-02 | 2021-12-07 | 南宁师范大学 | 17-酰胺雌甾类化合物及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE86393C (https=) * | ||||
| GB9118478D0 (en) * | 1991-08-29 | 1991-10-16 | Imperial College | Steroid sulphatase inhibitors |
| US5556847A (en) * | 1994-10-27 | 1996-09-17 | Duquesne University Of The Holy Ghost | Methods of effecting memory enhancement mediated by steroid sulfatase inhibitors |
| US5571933A (en) * | 1994-11-17 | 1996-11-05 | Duquesne University Of The Holy Ghost | Derivatives of estra 1,3,5(10)triene-17-one, 3-amino compounds and their use |
| US5567831A (en) * | 1995-08-16 | 1996-10-22 | Duguesne University Of The Holy Ghost | Non-steroidal sulfatase inhibitor compounds and their method of use |
-
1997
- 1997-07-18 US US08/897,247 patent/US5880115A/en not_active Expired - Fee Related
-
1998
- 1998-07-08 EP EP98936825A patent/EP1009755B1/en not_active Expired - Lifetime
- 1998-07-08 CA CA002296498A patent/CA2296498A1/en not_active Abandoned
- 1998-07-08 WO PCT/US1998/014206 patent/WO1999003876A1/en not_active Ceased
- 1998-07-08 JP JP2000503098A patent/JP2001510200A/ja active Pending
- 1998-07-08 AU AU85687/98A patent/AU729325B2/en not_active Ceased
- 1998-07-08 AT AT98936825T patent/ATE250077T1/de not_active IP Right Cessation
- 1998-07-08 DE DE69818278T patent/DE69818278T2/de not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1009755B1 (en) | 2003-09-17 |
| DE69818278T2 (de) | 2004-04-08 |
| ATE250077T1 (de) | 2003-10-15 |
| DE69818278D1 (de) | 2003-10-23 |
| US5880115A (en) | 1999-03-09 |
| CA2296498A1 (en) | 1999-01-28 |
| JP2001510200A (ja) | 2001-07-31 |
| EP1009755A4 (en) | 2002-11-06 |
| WO1999003876A1 (en) | 1999-01-28 |
| AU8568798A (en) | 1999-02-10 |
| EP1009755A1 (en) | 2000-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |