DK0580459T3 - Substituted phenylimidazolidines, their use as pharmaceuticals and pharmaceuticals containing them - Google Patents
Substituted phenylimidazolidines, their use as pharmaceuticals and pharmaceuticals containing themInfo
- Publication number
- DK0580459T3 DK0580459T3 DK93401361T DK93401361T DK0580459T3 DK 0580459 T3 DK0580459 T3 DK 0580459T3 DK 93401361 T DK93401361 T DK 93401361T DK 93401361 T DK93401361 T DK 93401361T DK 0580459 T3 DK0580459 T3 DK 0580459T3
- Authority
- DK
- Denmark
- Prior art keywords
- pharmaceuticals
- halogen
- image
- oxygen
- substituted
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P5/28—Antiandrogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
Abstract
The subject of the invention is the products of formula (I): <IMAGE> in which: R1 represents cyano, nitro or halogen, R2 represents trifluoromethyl or halogen, the -A-B- group is chosen from the radicals <IMAGE> in which X represents oxygen or sulphur and R3 is chosen from: - a hydrogen, - alkyl, alkenyl, alkynyl, aryl or arylalkyl, these radicals optionally being substituted, - trialkylsilyl, - acyl or acyloxy, Y represents oxygen or sulphur or NH, with the exception of the products in which: the -A-B- group represents the radical <IMAGE> in which X represents oxygen, R3 represents hydrogen, Y represents oxygen or NH, R2 represents halogen or trifluoromethyl and R1 represents nitro or halogen; the preparation and their application as medicaments, in particular as antiandrogens.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR929208431A FR2693461B1 (en) | 1992-07-08 | 1992-07-08 | New substituted phenylimidazolidines, process for their preparation, their use as medicaments and the pharmaceutical compositions containing them. |
Publications (1)
Publication Number | Publication Date |
---|---|
DK0580459T3 true DK0580459T3 (en) | 2001-06-11 |
Family
ID=9431679
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK93401361T DK0580459T3 (en) | 1992-07-08 | 1993-05-28 | Substituted phenylimidazolidines, their use as pharmaceuticals and pharmaceuticals containing them |
Country Status (17)
Country | Link |
---|---|
EP (1) | EP0580459B1 (en) |
JP (1) | JP3845455B2 (en) |
KR (1) | KR100294383B1 (en) |
CN (1) | CN1044234C (en) |
AT (1) | ATE200077T1 (en) |
AU (1) | AU670942B2 (en) |
CA (1) | CA2097248A1 (en) |
DE (1) | DE69330058T2 (en) |
DK (1) | DK0580459T3 (en) |
ES (1) | ES2155067T3 (en) |
FR (1) | FR2693461B1 (en) |
GR (1) | GR3035768T3 (en) |
HU (1) | HUT64527A (en) |
PT (1) | PT580459E (en) |
RU (1) | RU2116298C1 (en) |
UA (1) | UA34428C2 (en) |
ZA (1) | ZA933786B (en) |
Families Citing this family (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW521073B (en) * | 1994-01-05 | 2003-02-21 | Hoechst Marion Roussel Inc | New optionally substituted phenylimidazolidines, their preparation process, their use as anti-androgenic agent and the pharmaceutical compositions containing them |
FR2715402B1 (en) * | 1994-01-05 | 1996-10-04 | Roussel Uclaf | New phenylimidazolines optionally substituted, their process and preparation intermediates, their use as medicaments and the pharmaceutical compositions containing them. |
FR2724169B1 (en) * | 1994-09-06 | 1997-01-03 | Roussel Uclaf | NOVEL PHENYLIMIDAZOLIDINES WHICH MAY BE SUBSTITUTED, THEIR PROCESS AND PREPARATION INTERMEDIATES, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
FR2716110B1 (en) | 1994-02-16 | 1996-04-05 | Roussel Uclaf | Cosmetic or pharmaceutical compositions comprising liposomes. |
AU726572B2 (en) * | 1994-02-16 | 2000-11-09 | Aventis Pharma S.A. | Cosmetics or pharmaceutical compositions consisting of liposomes |
US5656651A (en) * | 1995-06-16 | 1997-08-12 | Biophysica Inc. | Androgenic directed compositions |
FR2741342B1 (en) * | 1995-11-22 | 1998-02-06 | Roussel Uclaf | NOVEL FLUORINATED OR HYDROXYLATED PHENYLIMIDAZOLIDINES, METHOD, PREPARATION MEDIA, APPLICATION AS MEDICAMENTS, NEW USE AND PHARMACEUTICAL COMPOSITIONS |
FR2742749B1 (en) | 1995-12-22 | 1998-02-06 | Roussel Uclaf | NOVEL PHENYLIMIDAZOLIDINES INCLUDING IN PARTICULAR A NITROOXY OR CARBONYLOXY RADICAL, PROCESS AND INTERMEDIATES FOR PREPARATION, APPLICATION AS MEDICAMENTS, NEW USES AND PHARMACEUTICAL COMPOSITIONS |
AU755165B2 (en) * | 1998-10-23 | 2002-12-05 | Aventis Pharma S.A. | Preparations for topical application of substances having antiandrogenic effect |
JP4621335B2 (en) | 2000-06-28 | 2011-01-26 | セイコーエプソン株式会社 | Printer unit for information terminals |
AU2002360932A1 (en) * | 2001-11-23 | 2003-06-10 | Schering Aktiengesellschaft | Piperazine derivatives destabilising androgen receptors |
US6861432B2 (en) | 2001-11-23 | 2005-03-01 | Schering Aktiengesellschaft | Piperazine derivatives that destabilize androgen receptors |
DE10218963A1 (en) * | 2002-04-27 | 2003-11-20 | Aventis Pharma Gmbh | Preparations for the topical application of antiandrogen active substances |
FR2845383B1 (en) * | 2002-10-04 | 2004-12-31 | Fournier Lab Sa | COMPOUNDS DERIVED FROM 2-THIOHYDANTOIN AND THEIR USE IN THERAPEUTICS |
AU2003279442A1 (en) * | 2002-10-04 | 2004-04-23 | Laboratoires Fournier S.A. | 2-thiohydantoine derivative compounds and use thereof for the treatment of diabetes |
DE10322108B4 (en) * | 2003-05-09 | 2008-12-11 | Bayer Schering Pharma Aktiengesellschaft | Antiandrogenic pyrrolidines with antitumor activity |
US7271188B2 (en) | 2003-06-12 | 2007-09-18 | Chugai Seikayu Kabushiki Kaisha | Imidazolidine derivatives |
NZ548209A (en) | 2003-12-19 | 2009-07-31 | Univ California | Methods and materials for assessing prostate cancer thearapies |
WO2005099693A2 (en) | 2004-02-24 | 2005-10-27 | The Regents Of The University Of California | Methods and materials for assessing prostate cancer therapies and compounds |
EP1621535A1 (en) * | 2004-07-27 | 2006-02-01 | Aventis Pharma S.A. | Substituted cyclic urea derivatives, preparation thereof and pharmaceutical use thereof as kinase inhibitors |
EP1775289B1 (en) * | 2004-08-03 | 2011-03-30 | Chugai Seiyaku Kabushiki Kaisha | Novel imidazolidine derivatives |
KR20070106969A (en) * | 2004-09-09 | 2007-11-06 | 추가이 세이야쿠 가부시키가이샤 | Novel imidazolidine derivative and use thereof |
KR20230003445A (en) * | 2005-05-13 | 2023-01-05 | 더 리전트 오브 더 유니버시티 오브 캘리포니아 | Diarylhydantoin compounds |
AU2013203255C1 (en) * | 2005-05-13 | 2017-01-19 | The Regents Of The University Of California | Diarylthiohydantoin compounds |
DK1891038T3 (en) * | 2005-05-13 | 2009-01-19 | Lilly Co Eli | Substituted n-arylpyrrolidines as selective androgen receptor modulators |
US7709517B2 (en) | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
US7709516B2 (en) * | 2005-06-17 | 2010-05-04 | Endorecherche, Inc. | Helix 12 directed non-steroidal antiandrogens |
CN101032483B (en) * | 2006-03-09 | 2011-05-04 | 陈德桂 | Hydantoin derivative for adjusting estrogen receptor activity and application thereof |
EP2368550B1 (en) | 2006-03-27 | 2013-09-04 | The Regents of the University of California | Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases |
SG170809A1 (en) * | 2006-03-29 | 2011-05-30 | Univ California | Diarylthiohydantoin compounds |
US9284345B2 (en) | 2007-04-12 | 2016-03-15 | Endorecherche, Inc. | 17alpha-substituted steroids as systemic antiandrogens and selective androgen receptor modulators |
TW201716385A (en) | 2007-10-26 | 2017-05-16 | 加州大學董事會 | Diarylhydantoin compounds |
WO2009097996A1 (en) * | 2008-02-07 | 2009-08-13 | Sanofi-Aventis | Use of substituted phenylimidazolidines for producing medicaments for treating metabolic syndrome |
WO2009097997A1 (en) * | 2008-02-07 | 2009-08-13 | Sanofi-Aventis | Substituted imidazolidine-2,4-diones, method for the production thereof, medicaments containing said compounds and use thereof |
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 |
WO2009145286A1 (en) | 2008-05-30 | 2009-12-03 | 武田薬品工業株式会社 | Heterocyclic compound |
WO2010069519A1 (en) | 2008-12-18 | 2010-06-24 | Merz Pharma Gmbh & Co. Kgaa | Topical compositions comprising at least one active ingredient poorly soluble in water and biopolymers such as hyaluronic acid with a pka-value between 5-7 |
WO2010092371A1 (en) | 2009-02-10 | 2010-08-19 | Astrazeneca Ab | Triazolo [4,3-b] pyridazine derivatives and their uses for prostate cancer |
FR2944524B1 (en) * | 2009-04-17 | 2012-11-30 | Ipsen Pharma Sas | IMIDAZOLIDINE-2,4-DIONE DERIVATIVES AND THEIR USE AS A MEDICINAL PRODUCT |
TW201111378A (en) | 2009-09-11 | 2011-04-01 | Bayer Schering Pharma Ag | Substituted (heteroarylmethyl) thiohydantoins |
FR2954317B1 (en) | 2009-12-23 | 2012-01-27 | Galderma Res & Dev | NOVEL PHENOLIC DERIVATIVES, AND THEIR PHARMACEUTICAL OR COSMETIC USE |
FR2954315B1 (en) | 2009-12-23 | 2012-02-24 | Galderma Res & Dev | NOVEL PHENOLIC DERIVATIVES, AND THEIR PHARMACEUTICAL OR COSMETIC USE |
FR2954316B1 (en) | 2009-12-23 | 2014-01-03 | Galderma Res & Dev | NOVEL PHENOLIC DERIVATIVES, AND THEIR PHARMACEUTICAL OR COSMETIC USE |
WO2011097496A1 (en) | 2010-02-04 | 2011-08-11 | Radius Health, Inc. | Selective androgen receptor modulators |
EP2536708A4 (en) | 2010-02-16 | 2013-05-29 | Aragon Pharmaceuticals Inc | Androgen receptor modulators and uses thereof |
JP5718372B2 (en) * | 2010-02-24 | 2015-05-13 | メディベイション プロステイト セラピューティクス, インコーポレイテッド | Process for the synthesis of diarylthiohydantoin compounds and diarylhydantoin compounds |
PT2568806T (en) | 2010-05-12 | 2016-08-05 | Radius Health Inc | Therapeutic regimens |
US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
EP2621901B1 (en) | 2010-09-28 | 2015-07-29 | Radius Health, Inc | Selective androgen receptor modulators |
CN104661658A (en) | 2012-09-26 | 2015-05-27 | 阿拉贡药品公司 | Anti-androgens for the treatment of non-metastatic castrate-resistant prostate cancer |
JOP20200097A1 (en) | 2013-01-15 | 2017-06-16 | Aragon Pharmaceuticals Inc | Androgen receptor modulator and uses thereof |
US9682960B2 (en) | 2013-12-19 | 2017-06-20 | Endorecherche, Inc. | Non-steroidal antiandrogens and selective androgen receptor modulators with a pyridyl moiety |
US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
US10420734B2 (en) | 2014-03-28 | 2019-09-24 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
CN103965112A (en) * | 2014-05-13 | 2014-08-06 | 上海孚一生物科技有限公司 | Compound with antiandrogen activity as well as preparation method and application of compound |
TWI726969B (en) | 2016-01-11 | 2021-05-11 | 比利時商健生藥品公司 | Substituted thiohydantoin derivatives as androgen receptor antagonists |
PL3474841T3 (en) | 2016-06-22 | 2022-07-11 | Ellipses Pharma Ltd | Ar+ breast cancer treatment methods |
JP2020514291A (en) | 2017-01-05 | 2020-05-21 | 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 | Polymorphic forms of RAD1901-2HCL |
CN111479560A (en) | 2017-10-16 | 2020-07-31 | 阿拉贡药品公司 | Antiandrogen for treating non-metastatic castration-resistant prostate cancer |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4916937B1 (en) * | 1970-01-21 | 1974-04-25 | ||
US3823240A (en) * | 1970-10-06 | 1974-07-09 | Rhone Poulenc Sa | Fungicidal hydantoin derivatives |
US3923994A (en) * | 1973-07-13 | 1975-12-02 | Smithkline Corp | Anti-arthritic compositions comprising a 3-aryl 2-thiohydantoin and methods of producing anti-arthritic acitvity |
FR2329276A1 (en) * | 1975-10-29 | 1977-05-27 | Roussel Uclaf | NEW SUBSTITUTES IMIDAZOLIDINES, METHOD OF PREPARATION, APPLICATION AS A MEDICINAL PRODUCT AND COMPOSITIONS CONTAINING THEM |
MC1220A1 (en) * | 1977-10-28 | 1979-07-20 | Hoffmann La Roche | NEW DERIVATIVES OF IMIDAZOLIDINE |
DE2933917A1 (en) * | 1979-08-22 | 1981-03-26 | Basf Ag, 67063 Ludwigshafen | 5-IMINO-IMIDAZOLIDIN-2-ONE AND HERBICIDES CONTAINING THEM. |
US4753957A (en) * | 1981-09-28 | 1988-06-28 | Rohm And Haas Company | Substituted 2,4-imidazolidinediones and fungicidal compositions |
EP0091596B1 (en) * | 1982-04-08 | 1991-09-11 | Shell Internationale Researchmaatschappij B.V. | Hydantoins, their preparation and application |
US4473393A (en) * | 1982-08-06 | 1984-09-25 | Buffalo Color Corporation | Pesticidal thiohydantoin compositions |
FR2656302B1 (en) * | 1989-12-22 | 1992-05-07 | Roussel Uclaf | NEW PROCESS FOR THE PREPARATION OF ANANDRON AND ANANDRON DERIVATIVES. |
FR2671348B1 (en) * | 1991-01-09 | 1993-03-26 | Roussel Uclaf | NOVEL PHENYLIMIDAZOLIDINES, THEIR PREPARATION PROCESS, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
-
1992
- 1992-07-08 FR FR929208431A patent/FR2693461B1/en not_active Expired - Fee Related
-
1993
- 1993-05-28 JP JP14837193A patent/JP3845455B2/en not_active Expired - Fee Related
- 1993-05-28 PT PT93401361T patent/PT580459E/en unknown
- 1993-05-28 RU RU93005350A patent/RU2116298C1/en not_active IP Right Cessation
- 1993-05-28 EP EP93401361A patent/EP0580459B1/en not_active Expired - Lifetime
- 1993-05-28 DK DK93401361T patent/DK0580459T3/en active
- 1993-05-28 HU HU9301585A patent/HUT64527A/en unknown
- 1993-05-28 DE DE69330058T patent/DE69330058T2/en not_active Expired - Fee Related
- 1993-05-28 AT AT93401361T patent/ATE200077T1/en not_active IP Right Cessation
- 1993-05-28 ZA ZA933786A patent/ZA933786B/en unknown
- 1993-05-28 CA CA002097248A patent/CA2097248A1/en not_active Abandoned
- 1993-05-28 CN CN93106567A patent/CN1044234C/en not_active Expired - Fee Related
- 1993-05-28 ES ES93401361T patent/ES2155067T3/en not_active Expired - Lifetime
- 1993-05-29 KR KR1019930009431A patent/KR100294383B1/en not_active IP Right Cessation
- 1993-05-31 AU AU39876/93A patent/AU670942B2/en not_active Ceased
- 1993-06-18 UA UA93003085A patent/UA34428C2/en unknown
-
2001
- 2001-04-20 GR GR20010400616T patent/GR3035768T3/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
EP0580459B1 (en) | 2001-03-28 |
EP0580459A1 (en) | 1994-01-26 |
UA34428C2 (en) | 2001-03-15 |
CN1044234C (en) | 1999-07-21 |
RU2116298C1 (en) | 1998-07-27 |
FR2693461B1 (en) | 1994-09-02 |
AU3987693A (en) | 1994-01-13 |
KR100294383B1 (en) | 2001-09-17 |
CA2097248A1 (en) | 1994-01-09 |
JP3845455B2 (en) | 2006-11-15 |
JPH0673017A (en) | 1994-03-15 |
AU670942B2 (en) | 1996-08-08 |
FR2693461A1 (en) | 1994-01-14 |
PT580459E (en) | 2001-07-31 |
GR3035768T3 (en) | 2001-07-31 |
HUT64527A (en) | 1994-01-28 |
ES2155067T3 (en) | 2001-05-01 |
KR940005582A (en) | 1994-03-21 |
CN1081182A (en) | 1994-01-26 |
ATE200077T1 (en) | 2001-04-15 |
HU9301585D0 (en) | 1993-09-28 |
ZA933786B (en) | 1994-05-30 |
DE69330058D1 (en) | 2001-05-03 |
DE69330058T2 (en) | 2001-09-06 |
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TH3325EX (en) | Phenylbenzoylurea | |
TH4707EX (en) | Phenylbenzoylurea | |
TH65065A (en) | Chemical compound |