CA1086751A - Procede de preparation de nouvelles imidazolidines substituees - Google Patents
Procede de preparation de nouvelles imidazolidines substitueesInfo
- Publication number
- CA1086751A CA1086751A CA264,606A CA264606A CA1086751A CA 1086751 A CA1086751 A CA 1086751A CA 264606 A CA264606 A CA 264606A CA 1086751 A CA1086751 A CA 1086751A
- Authority
- CA
- Canada
- Prior art keywords
- nitro phenyl
- trifluoromethyl
- imidazoline
- dimethyl
- imino
- 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
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 150000002462 imidazolines Chemical class 0.000 title 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- JQULXIOYDDCNGR-UHFFFAOYSA-N 2-amino-2-methylpropanenitrile Chemical compound CC(C)(N)C#N JQULXIOYDDCNGR-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- HIIVFEJATHLJHA-UHFFFAOYSA-N 5-imino-4,4-dimethyl-1-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidin-2-one Chemical compound N=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 HIIVFEJATHLJHA-UHFFFAOYSA-N 0.000 claims 4
- XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 claims 3
- YCZPVAWKLUWQBP-UHFFFAOYSA-N 4-isocyanato-1-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1C(F)(F)F YCZPVAWKLUWQBP-UHFFFAOYSA-N 0.000 claims 1
- 150000002461 imidazolidines Chemical class 0.000 abstract description 5
- 230000002280 anti-androgenic effect Effects 0.000 abstract description 4
- 210000002307 prostate Anatomy 0.000 description 11
- 241000700159 Rattus Species 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 8
- 230000009102 absorption Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000010348 incorporation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229960003604 testosterone Drugs 0.000 description 5
- KXALCBULAZGRHX-UHFFFAOYSA-N 4-amino-1,5-dihydroimidazol-2-one Chemical compound NC1=NC(=O)NC1 KXALCBULAZGRHX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- AZRRZGIBBLWSSQ-UHFFFAOYSA-N 4-ethyl-7-phenyl-3,5-diazabicyclo[2.2.2]octane-2,6-dione Chemical compound N1C(=O)C2C(=O)NC1(CC)CC2C1=CC=CC=C1 AZRRZGIBBLWSSQ-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940088597 hormone Drugs 0.000 description 3
- 239000005556 hormone Substances 0.000 description 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000051 antiandrogen Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- -1 of crames Substances 0.000 description 2
- 239000000700 radioactive tracer Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- ZZKDGABMFBCSRP-UHFFFAOYSA-N 3-ethyl-2-methylpyridine Chemical compound CCC1=CC=CN=C1C ZZKDGABMFBCSRP-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- OULQIRTYSJHFKP-UHFFFAOYSA-N 4h-imidazol-5-amine Chemical compound N=C1CNC=N1 OULQIRTYSJHFKP-UHFFFAOYSA-N 0.000 description 1
- GPVHHXRTFJHLTF-UHFFFAOYSA-N 5,5-dimethylimidazol-4-amine Chemical compound CC1(C)NC=NC1=N GPVHHXRTFJHLTF-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 208000003200 Adenoma Diseases 0.000 description 1
- BOJKULTULYSRAS-OTESTREVSA-N Andrographolide Chemical compound C([C@H]1[C@]2(C)CC[C@@H](O)[C@]([C@H]2CCC1=C)(CO)C)\C=C1/[C@H](O)COC1=O BOJKULTULYSRAS-OTESTREVSA-N 0.000 description 1
- 238000000846 Bartlett's test Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000283074 Equus asinus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 206010020112 Hirsutism Diseases 0.000 description 1
- 206010062767 Hypophysitis Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- 206010039792 Seborrhoea Diseases 0.000 description 1
- PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 210000003635 pituitary gland Anatomy 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229960001712 testosterone propionate Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 238000009736 wetting Methods 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Electromechanical Clocks (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7533084A FR2329276A1 (fr) | 1975-10-29 | 1975-10-29 | Nouvelles imidazolidines substituees, procede de preparation, application comme medicament et compositions les renfermant |
| FR75-33084 | 1975-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1086751A true CA1086751A (fr) | 1980-09-30 |
Family
ID=9161795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA264,606A Expired CA1086751A (fr) | 1975-10-29 | 1976-10-28 | Procede de preparation de nouvelles imidazolidines substituees |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4097578A (enExample) |
| JP (1) | JPS6011701B2 (enExample) |
| AU (1) | AU500542B2 (enExample) |
| BE (1) | BE847742A (enExample) |
| BG (1) | BG60533B2 (enExample) |
| CA (1) | CA1086751A (enExample) |
| CH (1) | CH599164A5 (enExample) |
| DE (1) | DE2649925C2 (enExample) |
| DK (1) | DK152125C (enExample) |
| ES (1) | ES452746A1 (enExample) |
| FR (1) | FR2329276A1 (enExample) |
| GB (1) | GB1518444A (enExample) |
| GE (1) | GEP19970948B (enExample) |
| IE (1) | IE43875B1 (enExample) |
| LU (2) | LU76085A1 (enExample) |
| NL (2) | NL187102C (enExample) |
| SE (1) | SE430502B (enExample) |
| SU (1) | SU596165A3 (enExample) |
Families Citing this family (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1138334A (en) * | 1977-10-28 | 1982-12-28 | Karl Bernauer | Pharmaceutical preparations containing certain urea derivatives |
| MC1220A1 (fr) * | 1977-10-28 | 1979-07-20 | Hoffmann La Roche | Nouveaux derives d'imidazolidine |
| FI801184A7 (fi) * | 1979-04-24 | 1981-01-01 | F Hoffmann La Roche & Co | Menetelmä imidatsolidiini-johdannaisten valmistamiseksi. |
| US4775660A (en) * | 1984-08-02 | 1988-10-04 | Fernand Labrie | Treatment of breast cancer by combination therapy |
| US4666885A (en) * | 1985-02-08 | 1987-05-19 | Fernand Labrie | Combination therapy for treatment of female breast cancer |
| US4760053A (en) * | 1984-08-02 | 1988-07-26 | Fernand Labrie | Combination therapy for selected sex steroid dependent cancers |
| ATE75947T1 (de) * | 1984-08-02 | 1992-05-15 | Labrie Fernand | Pharmazeutische zusammensetzung fuer die kombinationstherapie von hormonabhaengigem krebs. |
| IT1214735B (it) * | 1986-11-04 | 1990-01-18 | Roussel Maestretti Spa | Impiego di 1-(3'-trifluorometil 4'nitrofenil) 4,4-dimetilimidazolin2,5-dione per il trattamento di cancri ormonodipendenti diverso da quello della prostata |
| US5084472A (en) * | 1986-11-04 | 1992-01-28 | Roussel | Application of 1-(3'-trifluoromethyl-4'-nitrophenyl)-4,4'-dimethylimidazoline 2,5-dione in the treatment of hormone-dependent cancers other than that of the prostate |
| FR2619381B1 (fr) * | 1987-08-13 | 1989-12-08 | Roussel Uclaf | Nouvelles imidazolidines substituees par un radical hydroxymethyle et un radical phenyl substitue, leur procede de preparation, leur application comme medicaments, les compositions pharmaceutiques les renfermant et un intermediaire pour leur preparation |
| US4895715A (en) * | 1988-04-14 | 1990-01-23 | Schering Corporation | Method of treating gynecomastia |
| FR2656302B1 (fr) * | 1989-12-22 | 1992-05-07 | Roussel Uclaf | Nouveau procede de preparation de l'anandron et derives de l'anandron. |
| FR2671348B1 (fr) * | 1991-01-09 | 1993-03-26 | Roussel Uclaf | Nouvelles phenylimidazolidines, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant. |
| 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 |
| FR2693461B1 (fr) * | 1992-07-08 | 1994-09-02 | Roussel Uclaf | Nouvelles phénylimidazolidines substituées, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant. |
| US6002016A (en) * | 1991-12-20 | 1999-12-14 | Rhone-Poulenc Agrochimie | Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones |
| FR2706456B1 (fr) | 1993-06-18 | 1996-06-28 | Rhone Poulenc Agrochimie | Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| FR2685328B1 (fr) * | 1991-12-20 | 1995-12-01 | Rhone Poulenc Agrochimie | Derives de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| FR2694290B1 (fr) * | 1992-07-08 | 1994-09-02 | Roussel Uclaf | Nouvelles phénylimidazolidines éventuellement substituées, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant. |
| US6008370A (en) * | 1992-11-25 | 1999-12-28 | Rhone-Poulenc Agrochimie | Fungicidal-2-alkoxy/haloalkoxy-1-(mono- or disubstituted)amino-4,4-disubstituted-2-imidazolin-5-ones |
| 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 |
| FR2725206B1 (fr) * | 1994-09-29 | 1996-12-06 | Roussel Uclaf | Nouvelles imidazolidines substituees par un heterocycle, leur procede et des intermediaires de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
| US5656651A (en) * | 1995-06-16 | 1997-08-12 | Biophysica Inc. | Androgenic directed compositions |
| US6566372B1 (en) | 1999-08-27 | 2003-05-20 | Ligand Pharmaceuticals Incorporated | Bicyclic androgen and progesterone receptor modulator compounds and methods |
| US20040077605A1 (en) | 2001-06-20 | 2004-04-22 | Salvati Mark E. | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| IL152719A0 (en) * | 2000-06-28 | 2003-06-24 | Bristol Myers Squibb Co | Selective androgen receptor modulators and methods for their identification |
| US7001911B2 (en) | 2000-06-28 | 2006-02-21 | Bristol-Myers Squibb Company | Fused cyclic modulators of nuclear hormone receptor function |
| US6953679B2 (en) | 2000-09-19 | 2005-10-11 | Bristol-Myers Squibb Company | Method for the preparation of fused heterocyclic succinimide compounds and analogs thereof |
| EP1854798A3 (en) | 2000-09-19 | 2007-11-28 | Bristol-Myers Squibb Company | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| US20040087548A1 (en) | 2001-02-27 | 2004-05-06 | Salvati Mark E. | Fused cyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| WO2003005889A2 (en) * | 2001-07-10 | 2003-01-23 | Ams Research Corporation | Surgical kit for treating prostate tissue |
| ATE404544T1 (de) | 2001-12-19 | 2008-08-15 | Bristol Myers Squibb Co | Kondensierte heterocyclische verbindungen und deren analoga; modulatoren der funktion von nukleären hormonrezeptoren |
| FR2850652B1 (fr) * | 2003-01-31 | 2008-05-30 | Aventis Pharma Sa | Nouveaux derives d'uree cyclique, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de kinases |
| US7354933B2 (en) * | 2003-01-31 | 2008-04-08 | Aventis Pharma Sa | Cyclic urea derivatives, preparation thereof and pharmaceutical use thereof as kinase inhibitors |
| WO2005018573A2 (en) | 2003-08-22 | 2005-03-03 | Ligand Pharmaceuticals Incorporated | 6-cycloamino-2-quinolinone derivatives as androgen receptor modulator compounds |
| EP2428516A1 (en) | 2003-11-19 | 2012-03-14 | Metabasis Therapeutics, Inc. | Novel phosphorus-containing thyromimetics |
| ATE502298T1 (de) * | 2003-12-19 | 2011-04-15 | Univ California | Verfahren und materialien zur beurteilung von prostatakrebstherapien |
| NZ550102A (en) * | 2004-02-24 | 2010-10-29 | Univ California | Methods and materials for assessing prostate cancer therapies and compounds (thiohydantoine derivatives) |
| US8519158B2 (en) * | 2004-03-12 | 2013-08-27 | Ligand Pharmaceuticals Incorporated | Androgen receptor modulator compounds and methods |
| US7531565B2 (en) * | 2004-09-10 | 2009-05-12 | Janssen Pharmaceutica, N.V. | Imidazolidin-2-one derivatives as selective androgen receptor modulators (SARMS) |
| US7709517B2 (en) | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
| RS52274B2 (sr) | 2005-05-13 | 2018-05-31 | Univ California | Jedinjenje diarilhidantoina |
| NZ560354A (en) * | 2005-06-17 | 2010-10-29 | Ligand Pharm Inc | Androgen receptor modulator compounds and methods |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| FR2896503B1 (fr) * | 2006-01-23 | 2012-07-13 | Aventis Pharma Sa | Nouveaux derives soufres d'uree cyclique, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de kinases |
| NZ572335A (en) * | 2006-03-27 | 2011-09-30 | Univ California | Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases |
| WO2007127010A2 (en) * | 2006-03-29 | 2007-11-08 | The Regents Of The University Of California | Diarylthiohydantoin compounds |
| CN101663262B (zh) | 2006-12-01 | 2014-03-26 | 百时美施贵宝公司 | 用于治疗动脉粥样硬化和心血管疾病的作为cetp抑制剂的n-(3-苄基)-2,2-(二苯基)-丙-1胺衍生物 |
| EP4238519B1 (en) | 2007-01-02 | 2025-05-28 | AquaBeam LLC | Minimally invasive devices for the treatment of prostate diseases |
| US12290277B2 (en) | 2007-01-02 | 2025-05-06 | Aquabeam, Llc | Tissue resection with pressure sensing |
| US9232959B2 (en) | 2007-01-02 | 2016-01-12 | Aquabeam, Llc | Multi fluid tissue resection methods and devices |
| US20080245375A1 (en) * | 2007-04-05 | 2008-10-09 | Medtronic Vascular, Inc. | Benign Prostatic Hyperplasia Treatments |
| AR069039A1 (es) | 2007-10-26 | 2009-12-23 | Univ California | Compuestos de diarilhidantoina, composicion farmaceutica, proceso de obtencion del compuesto, utiles para desordenes hiperproliferativos |
| EP2259742B1 (en) | 2008-03-06 | 2020-01-01 | AquaBeam LLC | Tissue ablation and cautery with optical energy carried in fluid stream |
| US20120046364A1 (en) | 2009-02-10 | 2012-02-23 | Metabasis Therapeutics, Inc. | Novel Sulfonic Acid-Containing Thyromimetics, and Methods for Their Use |
| US9848904B2 (en) | 2009-03-06 | 2017-12-26 | Procept Biorobotics Corporation | Tissue resection and treatment with shedding pulses |
| FR2944524B1 (fr) * | 2009-04-17 | 2012-11-30 | Ipsen Pharma Sas | Derives d'imidazolidine-2,4-dione et leur utilisation comme medicament |
| CA2787083C (en) | 2010-02-16 | 2018-05-22 | Aragon Pharmaceuticals, Inc. | Androgen receptor modulators and uses thereof |
| EP2907504B1 (en) | 2011-02-08 | 2017-06-28 | Halozyme, Inc. | Composition and lipid formulation of a hyaluronan-degrading enzyme and the use thereof for treatment of benign prostatic hyperplasia |
| CN108606773B (zh) | 2012-02-29 | 2020-08-11 | 普罗赛普特生物机器人公司 | 自动化图像引导的组织切除和处理 |
| EP2900224A1 (en) | 2012-09-26 | 2015-08-05 | Aragon Pharmaceuticals, Inc. | Anti-androgens for the treatment of non-metastatic castrate-resistant prostate cancer |
| JOP20200097A1 (ar) | 2013-01-15 | 2017-06-16 | Aragon Pharmaceuticals Inc | معدل مستقبل أندروجين واستخداماته |
| EP2956070A4 (en) | 2013-02-14 | 2016-12-07 | Procept Biorobotics Corp | METHOD AND DEVICE FOR AQUABLATION AQUABEAM EYE SURGERY |
| WO2014130932A2 (en) | 2013-02-25 | 2014-08-28 | Novartis Ag | Novel androgen receptor mutation |
| JP6461971B2 (ja) | 2013-09-06 | 2019-01-30 | プロセプト バイオロボティクス コーポレイション | 飛散パルスを用いた組織切除および処置 |
| JP6651471B2 (ja) | 2014-06-30 | 2020-02-19 | プロセプト バイオロボティクス コーポレイション | 流体ジェット組織アブレーションおよび冷凝固（ａｑｕａｂｌａｔｉｏｎ）方法および装置 |
| JP2017532095A (ja) | 2014-09-05 | 2017-11-02 | プロセプト バイオロボティクス コーポレイション | 標的器官画像の処理マッピングと一体化された医師制御組織切除 |
| 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 |
| EP3500310A1 (en) | 2016-08-20 | 2019-06-26 | FTF Pharma Private Limited | Pharmaceutical composition comprising an androgen receptor inhibitor |
| CN107216290B (zh) * | 2017-06-12 | 2021-03-16 | 陕西科技大学 | 一种3-丁基-5,5-二甲基海因咪唑季铵盐及其制备方法 |
| CA3079135A1 (en) | 2017-10-16 | 2019-04-25 | Arturo Molina | Anti-androgens for the treatment of non-metastatic castration-resistant prostate cancer |
| WO2020214834A1 (en) | 2019-04-19 | 2020-10-22 | Ligand Pharmaceuticals Inc. | Crystalline forms and methods of producing crystalline forms of a compound |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB997037A (en) * | 1962-03-19 | 1965-06-30 | Ici Ltd | New hydrantoin derivatives |
| JPS4920973B1 (enExample) * | 1970-05-28 | 1974-05-29 | ||
| JPS5136332B1 (enExample) * | 1970-12-09 | 1976-10-07 | ||
| IL45459A (en) * | 1973-09-03 | 1978-01-31 | Ciba Geigy Ag | 1-(dichlorofluoromethylthio)-3-phenyl-imidazolidine-2,4-dione derivatives their preparation and their use as bactericides and fungicides |
-
1975
- 1975-10-29 FR FR7533084A patent/FR2329276A1/fr active Granted
-
1976
- 1976-09-30 SE SE7610859A patent/SE430502B/xx not_active IP Right Cessation
- 1976-10-20 NL NLAANVRAGE7611576,A patent/NL187102C/xx not_active IP Right Cessation
- 1976-10-21 US US05/734,557 patent/US4097578A/en not_active Expired - Lifetime
- 1976-10-21 SU SU762414002A patent/SU596165A3/ru active
- 1976-10-27 ES ES452746A patent/ES452746A1/es not_active Expired
- 1976-10-28 AU AU19095/76A patent/AU500542B2/en not_active Expired
- 1976-10-28 LU LU76085A patent/LU76085A1/xx unknown
- 1976-10-28 DK DK487476A patent/DK152125C/da not_active IP Right Cessation
- 1976-10-28 CA CA264,606A patent/CA1086751A/fr not_active Expired
- 1976-10-28 BE BE171876A patent/BE847742A/xx not_active IP Right Cessation
- 1976-10-29 IE IE2419/76A patent/IE43875B1/en not_active IP Right Cessation
- 1976-10-29 JP JP51129586A patent/JPS6011701B2/ja not_active Expired
- 1976-10-29 DE DE2649925A patent/DE2649925C2/de not_active Expired
- 1976-10-29 CH CH1369176A patent/CH599164A5/de active Protection Beyond IP Right Term
- 1976-10-29 GB GB45034/76A patent/GB1518444A/en not_active Expired
-
1993
- 1993-06-03 LU LU88282C patent/LU88282I2/fr unknown
- 1993-06-17 NL NL930079C patent/NL930079I2/nl unknown
- 1993-09-09 GE GEAP19931536A patent/GEP19970948B/en unknown
-
1994
- 1994-02-22 BG BG098507A patent/BG60533B2/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL930079I1 (nl) | 1993-09-16 |
| GB1518444A (en) | 1978-07-19 |
| LU88282I2 (fr) | 1994-05-04 |
| US4097578A (en) | 1978-06-27 |
| DK152125B (da) | 1988-02-01 |
| FR2329276B1 (enExample) | 1979-09-14 |
| NL187102C (nl) | 1991-06-03 |
| AU1909576A (en) | 1978-05-04 |
| DK152125C (da) | 1988-06-20 |
| NL930079I2 (nl) | 1993-10-01 |
| JPS6011701B2 (ja) | 1985-03-27 |
| FR2329276A1 (fr) | 1977-05-27 |
| CH599164A5 (enExample) | 1978-05-12 |
| DK487476A (da) | 1977-04-30 |
| BE847742A (fr) | 1977-04-28 |
| DE2649925C2 (de) | 1986-08-28 |
| ES452746A1 (es) | 1977-10-01 |
| AU500542B2 (en) | 1979-05-24 |
| LU76085A1 (enExample) | 1977-05-31 |
| SU596165A3 (ru) | 1978-02-28 |
| SE7610859L (sv) | 1977-04-30 |
| SE430502B (sv) | 1983-11-21 |
| IE43875B1 (en) | 1981-06-17 |
| NL7611576A (nl) | 1977-05-03 |
| BG60533B2 (bg) | 1995-07-28 |
| IE43875L (en) | 1977-04-29 |
| NL187102B (nl) | 1991-01-02 |
| JPS5257176A (en) | 1977-05-11 |
| GEP19970948B (en) | 1997-04-18 |
| DE2649925A1 (de) | 1977-05-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1086751A (fr) | Procede de preparation de nouvelles imidazolidines substituees | |
| CA1304093C (fr) | Imidazolidines substituees par un radical hydroxymethyle et un radical phenyle substitue, leur procede de preparation, leur application comme medicaments, lescompositions pharmaceutiques les renfermant et un intermediaire pour leur preparation | |
| EP0107569B1 (fr) | Nouveaux dérivés de la 6-amino 7-hydroxy 4,5,6,7-tétrahydroimidazo/4,5,1-j-k/ /1/ benzazépin-2(1H)-one, leurs sels, leur préparation, leur application à titre de médicaments, les compositions les renfermant | |
| CA2097247A1 (fr) | Phenylimidazolidines eventuellement substituees, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant | |
| CA1190226A (fr) | Procede de preparation de nouvelles pyrimido quinoxalines et de leurs sels | |
| EP0081324A2 (en) | Substituted pharmacologically acitve imidazole derivatives and their preparation and use | |
| EP0411735B1 (de) | Cycloakylenazole, Verfahren zu deren Herstellung, pharmazeutische Präparate, die diese enthalten sowie ihre Verwendung zur Herstellung von Arzneimitteln | |
| CA1095520A (fr) | Procede de preparation de nouveaux derives de 20,21- dinoreburnamenine | |
| EP0117771A1 (fr) | Imino-2 pyrrolidines, leur procédé de préparation et leurs applications en thérapeutique | |
| EP0324691A1 (fr) | Procédé de préparation d'hydroxyalkyl-1 nitro-5 imidazoles | |
| CA1133904A (fr) | Procedes de preparation de nouveaux derives de la piperidylbenzimidazolinone | |
| EP0443957B1 (fr) | Nouveaux produits stéroides comportant un radical spiro en position 17, leur procédé de préparation et les intermédiaires de ce procédé, leur application à titre de médicaments et les compositions pharmaceutiques les renfermant | |
| FR2600653A1 (fr) | Composes de synthese associative d'acides amines soufres ou non soufres avec des derives du d-4 pregnene 3,20-dione ou avec des derives du d-1,4 pregnadiene 3,20-dione aux proprietes glucocorticoides et anti-inflammatoires, procedes d'obtention, compositions pharmaceutiques les contenant. proprietes pharmacologiques et applications | |
| US4108993A (en) | 3-oxo-5,6-dihydro-1,2,4-oxadiazines useful as antiandrogenic agents | |
| EP0304353A1 (fr) | Dérivés de benzimidazole et leur préparation | |
| BE1001235A4 (fr) | Nouveaux derives azoliques, leur preparation et leur utilisation comme medicaments. | |
| EP0168309B1 (fr) | Nouveaux dérivés de l'isoxazoloquinoléinone, procédé et intermédiaires de préparation, application à titre de médicaments, et compositions les renfermant | |
| EP1257568B1 (fr) | Derives de l'echinocandine, leur procede de preparation et leur application comme fongicides | |
| LU85212A1 (fr) | Nouveaux derives de l'acide lysergique,leur preparation et leur utilisation comme medicaments | |
| WO1994000442A1 (fr) | Aryl-1 (o-alcoxyphenyl-4 piperazinyl-1)-2, -3 ou -4 alcanols, leur procede de preparation et leur utilisation pour la preparation de medicaments | |
| EP0384812A1 (fr) | Trifluorométhoxy-5 benzimidazolamine-2, procédé pour sa préparation et médicaments la contenant | |
| FR2500440A1 (fr) | Nouveaux medicaments derives de la 3-hydroxy dodecahydro benz (e) inden-7-one disubstituee en position 6, produits derives de la 3-hydroxy dodecahydro benz (e) inden-7-one disubstituee en position 6, et leur procede de preparation ainsi que des produits intermediaires | |
| FR2494698A1 (fr) | Nouveaux derives steroides 3-amino substitues, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant | |
| BE838902A (fr) | Nouveaux derives du benzo-cyclophepta-thiophene, leur preparation et leur application comme medicaments | |
| FR2595357A1 (fr) | (piperidino-3 propoxy)-5 p.cymene, les derives acetyl, acetoxy et hydroxy dudit produit, les sels de ces produits, un procede de preparation desdits produits et les medicaments contenant au moins un de ces produits comme principe actif |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |