JP2001524525A - エストロンスルファターゼのインヒビターとしてのステロイド３−ｏ−スルファメート誘導体 - Google Patents
エストロンスルファターゼのインヒビターとしてのステロイド３−ｏ−スルファメート誘導体Info
- Publication number
- JP2001524525A JP2001524525A JP2000522921A JP2000522921A JP2001524525A JP 2001524525 A JP2001524525 A JP 2001524525A JP 2000522921 A JP2000522921 A JP 2000522921A JP 2000522921 A JP2000522921 A JP 2000522921A JP 2001524525 A JP2001524525 A JP 2001524525A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- sulfamate
- group
- compound according
- oxime
- 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.)
- Pending
Links
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- 239000003112 inhibitor Substances 0.000 title claims abstract description 9
- 150000003431 steroids Chemical class 0.000 title claims description 16
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- -1 polycyclic compound Chemical class 0.000 claims abstract description 62
- 108010087999 Steryl-Sulfatase Proteins 0.000 claims abstract description 26
- 125000003544 oxime group Chemical group 0.000 claims abstract description 21
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims abstract description 10
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- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical class NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 25
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
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- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000007933 dermal patch Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 238000002657 hormone replacement therapy Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000937 inactivator Effects 0.000 description 1
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- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical class [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 159000000002 lithium salts Chemical class 0.000 description 1
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- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
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- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical class C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001147 pentyl group Chemical class C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 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 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
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- 230000002265 prevention Effects 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002914 sec-butyl group Chemical class [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9725749A GB2331987B (en) | 1997-12-04 | 1997-12-04 | Polycyclic sulphamate inhibitors of oestrone sulphatase |
| GB9725749.7 | 1997-12-04 | ||
| PCT/GB1998/003620 WO1999027936A1 (en) | 1997-12-04 | 1998-12-03 | Steroid 3-o-sulphamate derivatives as inhibitors of oestrone sulphatase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001524525A true JP2001524525A (ja) | 2001-12-04 |
| JP2001524525A5 JP2001524525A5 (enExample) | 2006-01-05 |
Family
ID=10823155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000522921A Pending JP2001524525A (ja) | 1997-12-04 | 1998-12-03 | エストロンスルファターゼのインヒビターとしてのステロイド３−ｏ−スルファメート誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6670353B2 (enExample) |
| EP (1) | EP1051178B1 (enExample) |
| JP (1) | JP2001524525A (enExample) |
| AT (1) | ATE451107T1 (enExample) |
| AU (1) | AU1345899A (enExample) |
| DE (1) | DE69841374D1 (enExample) |
| ES (1) | ES2337427T3 (enExample) |
| GB (1) | GB2331987B (enExample) |
| WO (1) | WO1999027936A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040127473A1 (en) * | 1996-12-05 | 2004-07-01 | Reed Michael John | Compound |
| GB2331987B (en) | 1997-12-04 | 2002-11-27 | Imperial College | Polycyclic sulphamate inhibitors of oestrone sulphatase |
| 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 |
| GB9913536D0 (en) * | 1999-06-10 | 1999-08-11 | Sterix Ltd | Use |
| JP4931312B2 (ja) * | 1999-12-13 | 2012-05-16 | ステリックス リミテッド | ステロイドスルファターゼのインヒビターとしてのハロゲン化スルファメート−、ホスホネート−、チオホスホネート−、スルホネート−、およびスルホンアミド−化合物 |
| US7335650B2 (en) | 2000-01-14 | 2008-02-26 | Sterix Limited | Composition |
| JPWO2001081364A1 (ja) | 2000-04-24 | 2004-01-08 | 協和醗酵工業株式会社 | エストラ−１，３，５（１０）−トリエン誘導体 |
| GB0025788D0 (en) * | 2000-10-20 | 2000-12-06 | Sterix Ltd | Use |
| AU2004224053B2 (en) * | 2003-03-24 | 2011-06-09 | Sterix Limited | Oestrogen derivatives as inhibitors of steroid sulphatase |
| GB0306718D0 (en) * | 2003-03-24 | 2003-04-30 | Sterix Ltd | Compound |
| GB0306717D0 (en) * | 2003-03-24 | 2003-04-30 | Sterix Ltd | Compound |
| GB0511190D0 (en) * | 2005-06-01 | 2005-07-06 | Sterix Ltd | Use |
| GB0624105D0 (en) * | 2006-12-01 | 2007-01-10 | Sterix Ltd | Use |
| EP2149371A1 (en) * | 2008-07-28 | 2010-02-03 | PregLem S.A. | Use of steroid sulfatase inhibitors for the treatment of preterm labor |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1398026A (en) * | 1972-11-10 | 1975-06-18 | Jenapharm Veb | Steroid esters |
| DE3046719C2 (de) * | 1980-12-11 | 1983-02-17 | Klinge Pharma GmbH, 8000 München | 1,1,2-Triphenyl-but-1-en-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel |
| US5273993A (en) * | 1989-06-12 | 1993-12-28 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfonyloxy radicals useful as pharmaceuticals |
| GB9625334D0 (en) * | 1996-12-05 | 1997-01-22 | Imperial College | Compound |
| GB9118478D0 (en) * | 1991-08-29 | 1991-10-16 | Imperial College | Steroid sulphatase inhibitors |
| US6083978A (en) * | 1996-03-05 | 2000-07-04 | Sterix Limited | Compounds with a sulfamate group |
| US6011024A (en) * | 1991-08-28 | 2000-01-04 | Imperial College Of Science Technology & Medicine | Steroid sulphatase inhibitors |
| GB9118465D0 (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 |
| US5763492A (en) | 1996-10-01 | 1998-06-09 | Duguesne University Of The Holy Ghost | Methods for effecting memory enhancement mediated by non-steroidal sulfatase inhibitors |
| GB2331987B (en) | 1997-12-04 | 2002-11-27 | Imperial College | Polycyclic sulphamate inhibitors of oestrone sulphatase |
| 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 |
-
1997
- 1997-12-04 GB GB9725749A patent/GB2331987B/en not_active Expired - Fee Related
-
1998
- 1998-12-03 JP JP2000522921A patent/JP2001524525A/ja active Pending
- 1998-12-03 AU AU13458/99A patent/AU1345899A/en not_active Abandoned
- 1998-12-03 DE DE69841374T patent/DE69841374D1/de not_active Expired - Lifetime
- 1998-12-03 AT AT98957034T patent/ATE451107T1/de not_active IP Right Cessation
- 1998-12-03 ES ES98957034T patent/ES2337427T3/es not_active Expired - Lifetime
- 1998-12-03 EP EP98957034A patent/EP1051178B1/en not_active Expired - Lifetime
- 1998-12-03 WO PCT/GB1998/003620 patent/WO1999027936A1/en not_active Ceased
-
2000
- 2000-05-17 US US09/572,237 patent/US6670353B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20020198396A1 (en) | 2002-12-26 |
| ATE451107T1 (de) | 2009-12-15 |
| DE69841374D1 (de) | 2010-01-21 |
| GB2331987B (en) | 2002-11-27 |
| ES2337427T3 (es) | 2010-04-23 |
| GB2331987A (en) | 1999-06-09 |
| GB2331987A9 (en) | 1900-01-01 |
| EP1051178B1 (en) | 2009-12-09 |
| US6670353B2 (en) | 2003-12-30 |
| AU1345899A (en) | 1999-06-16 |
| EP1051178A1 (en) | 2000-11-15 |
| WO1999027936A1 (en) | 1999-06-10 |
| GB9725749D0 (en) | 1998-02-04 |
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