ZA200307372B - Thiohydantoins and use thereof for treating diabetes. - Google Patents
Thiohydantoins and use thereof for treating diabetes. Download PDFInfo
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- ZA200307372B ZA200307372B ZA200307372A ZA200307372A ZA200307372B ZA 200307372 B ZA200307372 B ZA 200307372B ZA 200307372 A ZA200307372 A ZA 200307372A ZA 200307372 A ZA200307372 A ZA 200307372A ZA 200307372 B ZA200307372 B ZA 200307372B
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- 206010012601 diabetes mellitus Diseases 0.000 title claims description 6
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims description 97
- 238000002360 preparation method Methods 0.000 claims description 72
- -1 thiohydantoin derivative compound Chemical class 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 20
- 150000002540 isothiocyanates Chemical class 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
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- 239000011707 mineral Substances 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
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- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
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- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
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- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
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- 201000001421 hyperglycemia Diseases 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
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- 125000003277 amino group Chemical group 0.000 description 5
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- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical compound O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 235000002651 pink gum Nutrition 0.000 description 1
- 244000087877 pink gum Species 0.000 description 1
- XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0104552A FR2823209B1 (fr) | 2001-04-04 | 2001-04-04 | Nouvelles thiohydantoines et leur utilisation en therapeutique |
Publications (1)
Publication Number | Publication Date |
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ZA200307372B true ZA200307372B (en) | 2004-09-22 |
Family
ID=8861916
Family Applications (1)
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ZA200307372A ZA200307372B (en) | 2001-04-04 | 2003-09-22 | Thiohydantoins and use thereof for treating diabetes. |
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US (1) | US20040116417A1 (cs) |
EP (1) | EP1373219A1 (cs) |
JP (1) | JP2004525175A (cs) |
KR (1) | KR20030085565A (cs) |
CN (1) | CN1500081A (cs) |
BG (1) | BG108225A (cs) |
BR (1) | BR0207910A (cs) |
CA (1) | CA2444024A1 (cs) |
CZ (1) | CZ20032696A3 (cs) |
EE (1) | EE200300485A (cs) |
FR (1) | FR2823209B1 (cs) |
HU (1) | HUP0401537A3 (cs) |
IL (1) | IL158195A0 (cs) |
MX (1) | MXPA03009083A (cs) |
NO (1) | NO20034430L (cs) |
PL (1) | PL364904A1 (cs) |
RU (1) | RU2003129532A (cs) |
SK (1) | SK12332003A3 (cs) |
WO (1) | WO2002081453A1 (cs) |
YU (1) | YU75903A (cs) |
ZA (1) | ZA200307372B (cs) |
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US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
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ITMI20022748A1 (it) * | 2002-12-23 | 2004-06-24 | Eurand Int | Dispersioni solide stabilizzate di farmaco in un carrier organico e procedimento per la loro preparazione. |
US7605161B2 (en) * | 2003-07-30 | 2009-10-20 | Xenon Pharmaceuticals Inc. | Pyridyl derivatives and their use as therapeutic agents |
ES2375134T3 (es) * | 2003-07-30 | 2012-02-27 | Xenon Pharmaceuticals Inc. | Derivados de piperazina y su uso como agentes terapéuticos. |
DE602004031881D1 (de) * | 2003-12-19 | 2011-04-28 | Univ California | Verfahren und materialien zur beurteilung von prostatakrebstherapien |
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 |
DE102004024011A1 (de) * | 2004-05-14 | 2005-12-01 | Bayer Chemicals Ag | Difluorbenzo-1,3-dioxole |
EP2316457A1 (en) * | 2004-09-20 | 2011-05-04 | Xenon Pharmaceuticals Inc. | Pyridine derivatives for inhibiting human stearoyl-coa-desaturase |
EP2289510A1 (en) | 2004-09-20 | 2011-03-02 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
EP1804792A1 (en) * | 2004-09-20 | 2007-07-11 | Xenon Pharmaceuticals Inc. | Bicyclic heterocyclic derivatives and their use as inhibitors of stearoyl-coa-desaturase (scd) |
MX2007003321A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
US7951805B2 (en) * | 2004-09-20 | 2011-05-31 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
BRPI0515505A (pt) | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e sua utilização como inibidores da estearoil-coa desaturase |
JP5149009B2 (ja) * | 2004-09-20 | 2013-02-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | ヒトステアロイル−CoAデサチュラーゼを阻害するためのピリダジン誘導体 |
CA2580857A1 (en) * | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
WO2006034441A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
US7709517B2 (en) * | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
US8541457B2 (en) * | 2005-06-03 | 2013-09-24 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-CoA desaturase inhibitors |
FI2004181T6 (fi) * | 2006-03-27 | 2023-09-01 | Androgeenireseptorin modulaattori eturauhassyövän ja androgeenireseptoriin liittyvien sairauksien hoitamiseksi | |
AU2016201061B2 (en) * | 2006-03-27 | 2017-03-02 | The Regents Of The University Of California | Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases |
EP2439196A1 (en) | 2006-03-29 | 2012-04-11 | The Regents of The University of California | Diarylthiohydantoin compounds for use in a method for the treatment of a hyperproliferative disorder |
WO2008021338A2 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Tricyclic oxazolidone derivatives useful as pr modulators |
US7649007B2 (en) | 2006-08-15 | 2010-01-19 | Wyeth Llc | Oxazolidine derivatives as PR modulators |
TW200815428A (en) | 2006-08-15 | 2008-04-01 | Wyeth Corp | Oxazolidone derivatives as PR modulators |
WO2008021309A1 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Imidazolidin-2-one derivatives useful as pr modulators |
WO2008021337A1 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Oxazinan-2-one derivatives useful as pr modulators |
FR2917735B1 (fr) * | 2007-06-21 | 2009-09-04 | Sanofi Aventis Sa | Nouveaux indazoles substitutes, leur preparation et leur utilisation en therapeutique |
CA2703635C (en) | 2007-10-26 | 2017-06-27 | Michael E. Jung | Diarylhydantoin compounds as androgen receptor modulators |
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PT2430022E (pt) | 2009-05-12 | 2013-12-26 | Janssen Pharmaceuticals Inc | Derivados de 1,2,3-triazolo[4,3-a]piridina e a sua utilização para o tratamento ou prevenção de doenças neurológicas e psiquiátricas |
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DK2538785T3 (en) * | 2010-02-24 | 2018-05-22 | Medivation Prostate Therapeutics Llc | Methods for the synthesis of diarylthiohydantoin and diarylhydantoin compounds |
WO2013067142A1 (en) * | 2011-11-02 | 2013-05-10 | Medivation Technologies, Inc. | Compounds and treatment methods |
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JOP20200097A1 (ar) | 2013-01-15 | 2017-06-16 | Aragon Pharmaceuticals Inc | معدل مستقبل أندروجين واستخداماته |
ITUB20151256A1 (it) | 2015-05-28 | 2016-11-28 | Olon Spa | Processo industriale per la preparazione di enzalutamide |
TWI726969B (zh) | 2016-01-11 | 2021-05-11 | 比利時商健生藥品公司 | 用作雄性激素受體拮抗劑之經取代之硫尿囊素衍生物 |
KR20200070334A (ko) | 2017-10-16 | 2020-06-17 | 아라곤 파마슈티컬스, 인코포레이티드 | 비-전이성 거세-저항성 전립선암의 치료를 위한 항-안드로겐 |
WO2022206742A1 (zh) * | 2021-03-30 | 2022-10-06 | 苏州开拓药业股份有限公司 | 一种一步法合成乙内酰硫脲衍生物的方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2551134A (en) * | 1947-05-15 | 1951-05-01 | Du Pont | Process of color developing with 2-thiohydantoin 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 |
GB1472467A (en) * | 1974-04-19 | 1977-05-04 | Wyeth John & Brother Ltd | Thiohydantoins |
US4473393A (en) * | 1982-08-06 | 1984-09-25 | Buffalo Color Corporation | Pesticidal thiohydantoin compositions |
US4743611A (en) * | 1986-07-02 | 1988-05-10 | American Home Products Corp. | Naphthalenylsulfonylimidazolidinediones and their thioxo analogs useful as aldose reductase inhibitors |
US5821372A (en) * | 1995-11-28 | 1998-10-13 | American Home Products Corporation | 2-thioxo-imidazolidin-4-one derivatives |
US5554607A (en) * | 1995-11-28 | 1996-09-10 | American Home Products Corporation | Use of 2-thioxo-imidazolin-4-one derivatives in the treatment of atherosclerosis |
DE19741235A1 (de) * | 1997-09-18 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
-
2001
- 2001-04-04 FR FR0104552A patent/FR2823209B1/fr not_active Expired - Fee Related
-
2002
- 2002-04-04 EE EEP200300485A patent/EE200300485A/xx unknown
- 2002-04-04 CA CA002444024A patent/CA2444024A1/fr not_active Abandoned
- 2002-04-04 SK SK1233-2003A patent/SK12332003A3/sk unknown
- 2002-04-04 EP EP02730333A patent/EP1373219A1/fr not_active Withdrawn
- 2002-04-04 YU YU75903A patent/YU75903A/sh unknown
- 2002-04-04 JP JP2002579441A patent/JP2004525175A/ja not_active Withdrawn
- 2002-04-04 CN CNA028075811A patent/CN1500081A/zh active Pending
- 2002-04-04 PL PL02364904A patent/PL364904A1/xx not_active Application Discontinuation
- 2002-04-04 MX MXPA03009083A patent/MXPA03009083A/es unknown
- 2002-04-04 CZ CZ20032696A patent/CZ20032696A3/cs unknown
- 2002-04-04 RU RU2003129532/04A patent/RU2003129532A/ru not_active Application Discontinuation
- 2002-04-04 WO PCT/FR2002/001167 patent/WO2002081453A1/fr not_active Application Discontinuation
- 2002-04-04 KR KR10-2003-7012356A patent/KR20030085565A/ko not_active Withdrawn
- 2002-04-04 BR BR0207910-0A patent/BR0207910A/pt not_active Application Discontinuation
- 2002-04-04 IL IL15819502A patent/IL158195A0/xx unknown
- 2002-04-04 US US10/473,032 patent/US20040116417A1/en not_active Abandoned
- 2002-04-04 HU HU0401537A patent/HUP0401537A3/hu unknown
-
2003
- 2003-09-22 ZA ZA200307372A patent/ZA200307372B/en unknown
- 2003-10-03 NO NO20034430A patent/NO20034430L/no not_active Application Discontinuation
- 2003-10-03 BG BG108225A patent/BG108225A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
HUP0401537A2 (hu) | 2005-01-28 |
YU75903A (sh) | 2006-05-25 |
HUP0401537A3 (en) | 2005-06-28 |
EP1373219A1 (fr) | 2004-01-02 |
FR2823209B1 (fr) | 2003-12-12 |
CZ20032696A3 (cs) | 2003-12-17 |
CN1500081A (zh) | 2004-05-26 |
SK12332003A3 (sk) | 2004-04-06 |
BR0207910A (pt) | 2004-08-03 |
BG108225A (en) | 2005-04-30 |
WO2002081453A1 (fr) | 2002-10-17 |
FR2823209A1 (fr) | 2002-10-11 |
RU2003129532A (ru) | 2005-04-10 |
US20040116417A1 (en) | 2004-06-17 |
KR20030085565A (ko) | 2003-11-05 |
CA2444024A1 (fr) | 2002-10-17 |
PL364904A1 (en) | 2004-12-27 |
JP2004525175A (ja) | 2004-08-19 |
WO2002081453A8 (fr) | 2002-11-14 |
MXPA03009083A (es) | 2004-11-22 |
NO20034430D0 (no) | 2003-10-03 |
EE200300485A (et) | 2004-02-16 |
NO20034430L (no) | 2003-10-06 |
IL158195A0 (en) | 2004-03-28 |
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