WO2007096647A3 - 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 - Google Patents

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 Download PDF

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WO2007096647A3
WO2007096647A3 PCT/GB2007/000655 GB2007000655W WO2007096647A3 WO 2007096647 A3 WO2007096647 A3 WO 2007096647A3 GB 2007000655 W GB2007000655 W GB 2007000655W WO 2007096647 A3 WO2007096647 A3 WO 2007096647A3
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group
substituted
alkyl
optionally substituted
hydrocarbyl
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PCT/GB2007/000655
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French (fr)
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WO2007096647A2 (en
Inventor
Nigel Vicker
Gillian Margaret Allan
Harshani Rithma Ruchi Lawrence
Joanna Mary Day
Atul Purohit
Michael John Reed
Barry Victor Lloyd Potter
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Sterix Ltd
Nigel Vicker
Gillian Margaret Allan
Harshani Rithma Ruchi Lawrence
Joanna Mary Day
Atul Purohit
Michael John Reed
Barry Victor Lloyd Potter
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Priority claimed from GB0603894A external-priority patent/GB0603894D0/en
Priority claimed from GB0615464A external-priority patent/GB0615464D0/en
Application filed by Sterix Ltd, Nigel Vicker, Gillian Margaret Allan, Harshani Rithma Ruchi Lawrence, Joanna Mary Day, Atul Purohit, Michael John Reed, Barry Victor Lloyd Potter filed Critical Sterix Ltd
Priority to CA002643670A priority Critical patent/CA2643670A1/en
Priority to EP07712778A priority patent/EP2013176A2/en
Publication of WO2007096647A2 publication Critical patent/WO2007096647A2/en
Publication of WO2007096647A3 publication Critical patent/WO2007096647A3/en
Priority to US12/199,364 priority patent/US20090186900A1/en

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Abstract

There is provided a compound of Formula (I): wherein R3, R4, R5, R6, R7, R9, and R10, are independently selected from -H, -OH, hydrocarbyl groups, oxyhydrocarbyl groups, cyano (-CN), nitro (-NO2), and halogens; wherein ring A is optionally further substituted wherein X is a bond or a linker group wherein (A) (i) R9 is selected from alkyl and halogen groups; and (ii) R10 is selected from -OH, oxyhydrocarbyl and -OSO2NR1R2; wherein R1 and R2 are independently selected from H and hydrocarbyl or (B) at least one of R3, R4, R5, R6 and R7 is the group -C(=0)-CR11 R12-R8 wherein R8 is a selected from (i) an alkyloxyalkyl group (ii) a nitrile group, (iii) alkylaryl group, wherein the aryl group is substituted by other than a C1-10 group (iv) alkenylaryl group wherein the aryl group is substituted (v) alkylheteroaryl group, wherein when heteroaryl group comprises only C and N in the ring, the aryl group is substituted by other than a methyl group (vi) alkenylheteroaryl group (vii) =N-O-alkyl or =N-O-H group (viii) branched alkenyl (ix) alkyl-alcohol group or alkenyl-alcohol group (x) amide or alkylamide wherein (a) the alkyl of the alkylamide is -CH2- or - CH2CH2-, (b) the amide is di-substituted and/or (c) the amide is substituted with at least one of alkylheterocycle group, alkenylheterocycle group, alkylheteroaryl group, alkenylheteroaryl group, heteroaryl group, alkylamine group, alkyloxyalkyl group, alkylaryl group, straight or branched alkyl group, (xi) -CHO, or together with another of R3, R4, R5, R6 and R7 the enol tautomer thereof wherein R11 and R12 are independently selected from H and hydrocarbyl; or (C) at least one of R3, R4, R5, R6 and R7 together with another of R3, R4, R5, R6 and R7 forms a ring containing -C(=O)-; or (D) at least one of R3, R4, R5, R6 and R7 is selected from alkylheterocycle group, alkenylheterocycle group, alkylheteroaryl group, alkenylheteroaryl group, and heteroaryl groups or (E) at least one of R3, R4, R5, R6 and R7 is selected from -CN, -C(R13)=N-O-alkyl group, - C(R14)=N-O-H group, optionally substituted pyrazole, optionally substituted thiazole, optionally substituted oxazole, optionally substituted isoxazole, optionally substituted pyridine, and optionally substituted pyrimidine, or together with another of R3, R4, R5, R6 and R7 forms a nitrogen containing ring; wherein R13 and R14 are independently selected from H and hydrocarbyl.
PCT/GB2007/000655 2006-02-27 2007-02-26 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 WO2007096647A2 (en)

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Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0722779D0 (en) 2007-11-20 2008-01-02 Sterix Ltd Compound
FR2926297B1 (en) * 2008-01-10 2013-03-08 Centre Nat Rech Scient INHIBITORY CHEMICAL MOLECULES IN THE SPLICE MECHANISM FOR TREATING DISEASES RESULTING FROM SPLICE ANOMALIES.
US8455499B2 (en) 2008-12-11 2013-06-04 Amira Pharmaceuticals, Inc. Alkyne antagonists of lysophosphatidic acid receptors
GB2466121B (en) 2008-12-15 2010-12-08 Amira Pharmaceuticals Inc Antagonists of lysophosphatidic acid receptors
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WO2012099904A1 (en) 2011-01-18 2012-07-26 General Atomics Hydrolase enzyme substrates and uses thereof
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WO2021003295A1 (en) * 2019-07-02 2021-01-07 Regeneron Pharmaceuticals, Inc. Modulators of hsd17b13 and methods of use thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1522570A (en) * 1966-09-08 1968-04-26 Merck & Co Inc Phenylbenzoic acid compounds
WO2003068217A1 (en) * 2002-02-15 2003-08-21 Endorecherche, Inc. Biphenil derivatives and their use as antiandrogenic agents
WO2004110459A1 (en) * 2003-06-10 2004-12-23 Solvay Pharmaceuticals B.V. Thiophenepyrimidinones as 17-beta-hydroxysteroid dehydrogenase inhibitors
WO2005047303A2 (en) * 2003-11-12 2005-05-26 Solvay Pharmaceuticals Gmbh NOVEL 17β HYDROXYSTEROID DEHYDROGENASE TYPE I INHIBITORS
US20050192310A1 (en) * 2004-03-01 2005-09-01 Gavai Ashvinikumar V. Fused heterotricyclic compounds as inhibitors of 17beta-hydroxysteroid dehydrogenase 3

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB750155A (en) * 1953-03-17 1956-06-13 Nat Res Dev Substituted alanines
NL242386A (en) * 1958-09-24
US3074937A (en) * 1960-08-27 1963-01-22 Vismara Francesco Spa Diphenylcarbonylmethinylhydrazidoalkyl quaternary salts
BE759053A (en) * 1969-11-17 1971-05-17 Thomae Gmbh Dr K NEW HYDROXYCROTONIC ACIDS AND METHODS FOR MAKING THEM
GB1396726A (en) * 1972-06-15 1975-06-04 Boots Co Ltd Phenylalkanoic acids
JPS52142683A (en) * 1976-05-25 1977-11-28 Citizen Watch Co Ltd Liquid crystal composite
US5516931A (en) * 1982-02-01 1996-05-14 Northeastern University Release tag compounds producing ketone signal groups
US4536517A (en) * 1983-04-25 1985-08-20 American Cyanamid Company Method of treating diabetes mellitus using arylglyoxals
JPH0794406B2 (en) * 1984-02-08 1995-10-11 チッソ株式会社 Liquid crystalline substituted biphenyl esters

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1522570A (en) * 1966-09-08 1968-04-26 Merck & Co Inc Phenylbenzoic acid compounds
WO2003068217A1 (en) * 2002-02-15 2003-08-21 Endorecherche, Inc. Biphenil derivatives and their use as antiandrogenic agents
WO2004110459A1 (en) * 2003-06-10 2004-12-23 Solvay Pharmaceuticals B.V. Thiophenepyrimidinones as 17-beta-hydroxysteroid dehydrogenase inhibitors
WO2005047303A2 (en) * 2003-11-12 2005-05-26 Solvay Pharmaceuticals Gmbh NOVEL 17β HYDROXYSTEROID DEHYDROGENASE TYPE I INHIBITORS
US20050192310A1 (en) * 2004-03-01 2005-09-01 Gavai Ashvinikumar V. Fused heterotricyclic compounds as inhibitors of 17beta-hydroxysteroid dehydrogenase 3

Non-Patent Citations (23)

* Cited by examiner, † Cited by third party
Title
BUU-HOI ET AL., BULL. SOC. CHIM. FR, 1959, pages 477 *
BUU-HOI ET AL., J. ORG. CHEM., 1957, pages 666 *
CINCINELLI ET AL., J. MED. CHEM, 2005, pages 4931 - 4946 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002444435 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002444436 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002444437 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002444438 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002444439 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002444440 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002444441 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002444442 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002444443 *
DAVIS ET AL., J. CHEM. SOC. PERKIN TRANS. I, 1982, pages 1499 - 1508 *
GFESSER ET AL., BIOORG. MED. CHEM. LETT., 2005, pages 2559 - 2564 *
GUNN, DAVID ET AL: "4,5-Disubstituted cis-pyrrolidinones as inhibitors of type II 17 . beta .- hydroxysteroid dehydrogenase . Part 2. SAR", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 15(12), 3053-3057 CODEN: BMCLE8; ISSN: 0960-894X, 2005, XP002444432 *
HANNAH ET AL., J. MED. CHEM, 1978, pages 1093 - 1100 *
HEWGILL ET AL., AUST. J. CHEM., 1978, pages 1070 - 1072 *
KELLY ET AL., HELV. CHIM. ACTA, 1989, pages 594 - 607 *
KOELBEL ET AL., J. AM. CHEM. SOC., 2001, pages 6809 - 6818 *
LAMARTINE ET AL., CAN. J. CHEM., 1972, pages 2882 *
MOORE ET AL., J. ORG. CHEM., 1979, pages 925 - 929 *
OKADA, MAKOTO ET AL: "Development of novel steroid sulfatase inhibitors I. Synthesis and biological evaluation of biphenyl-4-O-sulfamates", JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY , VOLUME DATE 2003, 87(2-3), 141-148 CODEN: JSBBEZ; ISSN: 0960-0760, 2004, XP002444433 *
SAITO, TOMOYUKI ET AL: "Development of novel steroid sulfatase inhibitors II. TZS-8478 potently inhibits the growth of breast tumors in postmenopausal breast cancer model rats", JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY , 88(2), 167-173 CODEN: JSBBEZ; ISSN: 0960-0760, 2004, XP002444434 *

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