KR850000719B1 - 이미다졸리딘 유도체의 제조방법 - Google Patents
이미다졸리딘 유도체의 제조방법 Download PDFInfo
- Publication number
- KR850000719B1 KR850000719B1 KR1019800001691A KR800001691A KR850000719B1 KR 850000719 B1 KR850000719 B1 KR 850000719B1 KR 1019800001691 A KR1019800001691 A KR 1019800001691A KR 800001691 A KR800001691 A KR 800001691A KR 850000719 B1 KR850000719 B1 KR 850000719B1
- Authority
- KR
- South Korea
- Prior art keywords
- solution
- phenyl
- compound
- formula
- mmol
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000002461 imidazolidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical class C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
- 239000000243 solution Substances 0.000 description 41
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- -1 3-trifluoromethyl-4-fluoro-phenyl Chemical group 0.000 description 20
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
- 235000017557 sodium bicarbonate Nutrition 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000003208 petroleum Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- JQULXIOYDDCNGR-UHFFFAOYSA-N 2-amino-2-methylpropanenitrile Chemical compound CC(C)(N)C#N JQULXIOYDDCNGR-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 229940091173 hydantoin Drugs 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- PGFQDLOMDIBAPY-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)aniline Chemical compound NC1=CC=C(F)C(C(F)(F)F)=C1 PGFQDLOMDIBAPY-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 230000002280 anti-androgenic effect Effects 0.000 description 4
- 239000000051 antiandrogen Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 4
- YGAIHENVDYKRCA-UHFFFAOYSA-N 1-[4-fluoro-3-(trifluoromethyl)phenyl]-5-imino-4,4-dimethylimidazolidin-2-one Chemical compound N=C1C(C)(C)NC(=O)N1C1=CC=C(F)C(C(F)(F)F)=C1 YGAIHENVDYKRCA-UHFFFAOYSA-N 0.000 description 3
- KXALCBULAZGRHX-UHFFFAOYSA-N 4-amino-1,5-dihydroimidazol-2-one Chemical compound NC1=NC(=O)NC1 KXALCBULAZGRHX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- BTGSGTWRNQCEQY-UHFFFAOYSA-N 3-[4-fluoro-3-(trifluoromethyl)phenyl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C(F)C(C(F)(F)F)=C1 BTGSGTWRNQCEQY-UHFFFAOYSA-N 0.000 description 2
- VPJKJQOEEGWPEC-UHFFFAOYSA-N 4-aminoimidazolidin-2-one Chemical compound NC1CNC(=O)N1 VPJKJQOEEGWPEC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 241000242678 Schistosoma Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000003394 haemopoietic effect Effects 0.000 description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 2
- UYMCNKBLWIZQGB-UHFFFAOYSA-N phenyl n-(3-chloro-4-fluorophenyl)carbamate Chemical compound C1=C(Cl)C(F)=CC=C1NC(=O)OC1=CC=CC=C1 UYMCNKBLWIZQGB-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
- VTWDOMAUSAHNFK-UHFFFAOYSA-N 1-(2-cyanopropyl)-3-[4-fluoro-3-(trifluoromethyl)phenyl]urea Chemical compound C(#N)C(CNC(=O)NC1=CC(=C(C=C1)F)C(F)(F)F)C VTWDOMAUSAHNFK-UHFFFAOYSA-N 0.000 description 1
- GGUGWVOGQXTERV-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-5-imino-4,4-dimethylimidazolidin-2-one Chemical compound N=C1C(C)(C)NC(=O)N1C1=CC=C(Cl)C(Cl)=C1 GGUGWVOGQXTERV-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- ZUFUZSVHWNKTSD-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C(Cl)C(Cl)=C1 ZUFUZSVHWNKTSD-UHFFFAOYSA-N 0.000 description 1
- KXJGSEHRBVEMQL-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C(F)C(Cl)=C1 KXJGSEHRBVEMQL-UHFFFAOYSA-N 0.000 description 1
- YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- YVBUJCRJSRRLHH-UHFFFAOYSA-N CC1(C(=O)N(C(=O)N1)C2=CC=CC(=C2F)C(F)(F)F)C Chemical compound CC1(C(=O)N(C(=O)N1)C2=CC=CC(=C2F)C(F)(F)F)C YVBUJCRJSRRLHH-UHFFFAOYSA-N 0.000 description 1
- 241000938605 Crocodylia Species 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000935974 Paralichthys dentatus Species 0.000 description 1
- 206010036940 Prostatic adenoma Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000242680 Schistosoma mansoni Species 0.000 description 1
- 206010039792 Seborrhoea Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 210000002989 hepatic vein Anatomy 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 244000045947 parasite Species 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- MVXLHYKEKXUFFZ-UHFFFAOYSA-N phenyl n-(3,4-dichlorophenyl)carbamate Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)OC1=CC=CC=C1 MVXLHYKEKXUFFZ-UHFFFAOYSA-N 0.000 description 1
- IZTYAOFWKLCNPQ-UHFFFAOYSA-N phenyl n-(3-methylphenyl)carbamate Chemical compound CC1=CC=CC(NC(=O)OC=2C=CC=CC=2)=C1 IZTYAOFWKLCNPQ-UHFFFAOYSA-N 0.000 description 1
- TVVPLXNULUGACT-UHFFFAOYSA-N phenyl n-[4-fluoro-3-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1NC(=O)OC1=CC=CC=C1 TVVPLXNULUGACT-UHFFFAOYSA-N 0.000 description 1
- XVNKRRXASPPECQ-UHFFFAOYSA-N phenyl n-phenylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1=CC=CC=C1 XVNKRRXASPPECQ-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Resins (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3837 | 1979-04-24 | ||
| CH383779 | 1979-04-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830002722A KR830002722A (ko) | 1983-05-30 |
| KR850000719B1 true KR850000719B1 (ko) | 1985-05-23 |
Family
ID=4264536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019800001691A Expired KR850000719B1 (ko) | 1979-04-24 | 1980-04-24 | 이미다졸리딘 유도체의 제조방법 |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0017976B1 (https=) |
| JP (1) | JPS55143974A (https=) |
| KR (1) | KR850000719B1 (https=) |
| AT (1) | ATE3860T1 (https=) |
| CA (1) | CA1135706A (https=) |
| DE (1) | DE3063837D1 (https=) |
| DK (1) | DK174480A (https=) |
| ES (1) | ES8104243A1 (https=) |
| FI (1) | FI801184A7 (https=) |
| GR (1) | GR67605B (https=) |
| HU (1) | HU184271B (https=) |
| NO (1) | NO801182L (https=) |
| PT (1) | PT71135B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5411981A (en) * | 1991-01-09 | 1995-05-02 | Roussel Uclaf | Phenylimidazolidines having antiandrogenic activity |
| USRE35956E (en) * | 1991-01-09 | 1998-11-10 | Roussel Uclaf | Phenylimidazolidines having antiandrogenic activity |
| FR2724169B1 (fr) * | 1994-09-06 | 1997-01-03 | Roussel Uclaf | Nouvelles phenylimidazolidines eventuellement substituees, leur procede et des intermediaires de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
| FR2715402B1 (fr) * | 1994-01-05 | 1996-10-04 | Roussel Uclaf | Nouvelles phénylimidazolines éventuellement substituées, leur procédé et des intermédiaires de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant. |
| 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 |
| AU2004305075A1 (en) | 2003-12-19 | 2005-07-07 | The Regents Of The University Of California | Methods and materials for assessing prostate cancer therapies |
| NZ550102A (en) | 2004-02-24 | 2010-10-29 | Univ California | Methods and materials for assessing prostate cancer therapies and compounds (thiohydantoine derivatives) |
| US7709517B2 (en) | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
| LT2656842T (lt) | 2006-03-27 | 2016-09-26 | The Regents Of The University Of California | Androgeno receptoriaus moduliatorius, skirtas prostatos vėžio ir su androgeno receptoriumi susijusių ligų gydymui |
| KR101456722B1 (ko) | 2006-03-29 | 2014-10-31 | 더 리전트 오브 더 유니버시티 오브 캘리포니아 | 디아릴티오히단토인 화합물 |
| TWI469971B (zh) | 2007-10-26 | 2015-01-21 | Univ California | 二芳基乙內醯脲類化合物 |
| WO2011103202A2 (en) | 2010-02-16 | 2011-08-25 | Aragon Pharmaceuticals, Inc. | Androgen receptor modulators and uses thereof |
| SG11201501870RA (en) | 2012-09-26 | 2015-04-29 | Aragon Pharmaceuticals Inc | Anti-androgens for the treatment of non-metastatic castrate-resistant prostate cancer |
| SG10201907684PA (en) | 2013-01-15 | 2019-10-30 | Aragon Pharmaceuticals Inc | Androgen receptor modulator and uses thereof |
| 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 |
| AU2018351714A1 (en) | 2017-10-16 | 2020-04-30 | Aragon Pharmaceuticals, Inc. | Anti-androgens for the treatment of non-metastatic castration-resistant prostate cancer |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB997037A (en) * | 1962-03-19 | 1965-06-30 | Ici Ltd | New hydrantoin derivatives |
| US3340070A (en) * | 1963-08-23 | 1967-09-05 | Shell Oil Co | Artificial sweetening agent |
| FR2329276A1 (fr) * | 1975-10-29 | 1977-05-27 | Roussel Uclaf | Nouvelles imidazolidines substituees, procede de preparation, application comme medicament et compositions les renfermant |
| MC1220A1 (fr) * | 1977-10-28 | 1979-07-20 | Hoffmann La Roche | Nouveaux derives d'imidazolidine |
| IL55774A (en) * | 1977-10-28 | 1982-04-30 | Sparamedica Ag | Pharmaceutical compositions containing urea derivatives,certain such novel derivatives and their manufacture |
-
1980
- 1980-04-14 FI FI801184A patent/FI801184A7/fi not_active Application Discontinuation
- 1980-04-16 AT AT80102042T patent/ATE3860T1/de not_active IP Right Cessation
- 1980-04-16 DE DE8080102042T patent/DE3063837D1/de not_active Expired
- 1980-04-16 EP EP80102042A patent/EP0017976B1/de not_active Expired
- 1980-04-18 CA CA000350162A patent/CA1135706A/en not_active Expired
- 1980-04-21 JP JP5180480A patent/JPS55143974A/ja active Pending
- 1980-04-22 GR GR61749A patent/GR67605B/el unknown
- 1980-04-23 NO NO801182A patent/NO801182L/no unknown
- 1980-04-23 HU HU80995A patent/HU184271B/hu unknown
- 1980-04-23 ES ES490799A patent/ES8104243A1/es not_active Expired
- 1980-04-23 DK DK174480A patent/DK174480A/da not_active Application Discontinuation
- 1980-04-23 PT PT71135A patent/PT71135B/pt unknown
- 1980-04-24 KR KR1019800001691A patent/KR850000719B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0017976A2 (de) | 1980-10-29 |
| PT71135A (en) | 1980-05-01 |
| DK174480A (da) | 1980-10-25 |
| GR67605B (https=) | 1981-08-31 |
| EP0017976B1 (de) | 1983-06-22 |
| CA1135706A (en) | 1982-11-16 |
| JPS55143974A (en) | 1980-11-10 |
| KR830002722A (ko) | 1983-05-30 |
| HU184271B (en) | 1984-07-30 |
| ATE3860T1 (de) | 1983-07-15 |
| ES490799A0 (es) | 1981-04-16 |
| NO801182L (no) | 1980-10-27 |
| FI801184A7 (fi) | 1981-01-01 |
| PT71135B (en) | 1981-08-07 |
| EP0017976A3 (en) | 1981-04-01 |
| DE3063837D1 (en) | 1983-07-28 |
| ES8104243A1 (es) | 1981-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR850000719B1 (ko) | 이미다졸리딘 유도체의 제조방법 | |
| SU820659A3 (ru) | Способ получени производных 4-амино- 5-АлКилСульфОНилОАНизАМидОВ, иХ СОлЕй,ОКиСЕй, лЕВО- и пРАВОВРАщАющиХизОМЕРОВ /иХ ВАРиАНТы/ | |
| FI73682C (fi) | Foerfarande foer framstaellning av antiviralt 9-(1,3-dihydroxi-2-propoximetyl)guanin samt mellanprodukt. | |
| US3679698A (en) | 2-nitroimidazoles | |
| EP0288973B1 (en) | Benzothiazolinone derivatives, their production and pharmaceutical composition | |
| CY1446A (en) | Chemical compounds derived from cyclobutene | |
| PT91580B (pt) | Processo para a preparacao de compostos de nicotinamida n-substituida antidepressivos | |
| SU1241986A3 (ru) | Способ получени производных бензамида,их гидрохлоридов или оптических изомеров | |
| FR2615512A1 (fr) | Composes de benzamides substitues pharmacologiquement actifs, compositions pharmaceutiques contenant ces composes, et leur procede de preparation | |
| EP0029663B1 (en) | N-aryl-n'-imidazol-2-ylureas, process for their preparation and pharmaceutical compositions containing them | |
| US5101072A (en) | Sulfonylhydrazines and their use as antineoplastic agents and as antitrypanosomal agents | |
| JP3210117B2 (ja) | 抗腫瘍剤および腫瘍の治療方法 | |
| US5214068A (en) | Sulfonylhydrazines and their use as antineoplastic agents and as antitrypanosomal agents | |
| US4203909A (en) | Furan compounds | |
| DE3035688C2 (https=) | ||
| RU2024507C1 (ru) | 5-хлор-2-пиридиламид-4-нитро-n-(карбоксиметил)антраниловой кислоты, проявляющий противовоспалительную активность | |
| CA1299579C (fr) | Benzamides, leur procede d'obtention et leurs applications therapeutiques | |
| US3659012A (en) | Methods of treating helminth infections with thiourea derivatives | |
| US4539316A (en) | Pyridine derivatives of 1,2-diaminocyclobutene-3,4-diones | |
| US4200760A (en) | Imidazolylalkylthioalkylamino-ethylene derivatives | |
| US4353923A (en) | Pharmaceutical composition containing a benzofurancarboxamide derivative as the active ingredient | |
| EP0000640B1 (en) | Tetrahydro-s-triazine thiones, process for their preparation and acaricidal compositions containing them. | |
| NZ201696A (en) | 2-arylazo and 2-arylhydrazino-2-thiazoline derivatives and ecto-and endo-parasiticidal compositions | |
| ES2520021T3 (es) | Derivados de 3,4-diamino-3-ciclobuteno-1,2-diona como aperturas de canal de potasio | |
| CZ695188A3 (en) | ENOL ETHER OF 1,1-DIOXIDE OF 6-CHLORO-4-HYDROXY-2-METHYL-N- (2-PYRIDYL-2H-THIENO(2,3-c)-1,2-THIAZINECARBOXYLIC ACID AMIDE, PROCESS OF ITS PREPARATION AND ITS USE |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19800424 |
|
| PG1501 | Laying open of application | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19840229 Patent event code: PE09021S01D |
|
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19841029 Patent event code: PE09021S01D |
|
| PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19850417 |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19850807 |