CA1206471A - Procede de preparation de nouveaux derives 3-ceto .delta.4,9 19-nor steroides - Google Patents
Procede de preparation de nouveaux derives 3-ceto .delta.4,9 19-nor steroidesInfo
- Publication number
- CA1206471A CA1206471A CA000422503A CA422503A CA1206471A CA 1206471 A CA1206471 A CA 1206471A CA 000422503 A CA000422503 A CA 000422503A CA 422503 A CA422503 A CA 422503A CA 1206471 A CA1206471 A CA 1206471A
- Authority
- CA
- Canada
- Prior art keywords
- beta
- radical
- alpha
- prop
- ynyl
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 61
- -1 hydroxyimino Chemical group 0.000 claims abstract description 206
- 239000004593 Epoxy Substances 0.000 claims abstract description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 6
- 125000004665 trialkylsilyl group Chemical group 0.000 claims abstract description 5
- 125000000676 alkoxyimino group Chemical group 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 4
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 59
- 239000005977 Ethylene Substances 0.000 claims description 45
- DBLOJPKZEOYNBN-SQNIBIBYSA-N (8s,13s,14s)-13-methyl-2,6,7,8,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CCC2=C2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 DBLOJPKZEOYNBN-SQNIBIBYSA-N 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 29
- 150000003254 radicals Chemical class 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- DPYMYZUVYDCURI-LLHIWASSSA-N (8S,13S,14S)-13-methyl-1,2,3,4,5,6,7,8,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene Chemical compound C1CC2CCCCC2=C2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 DPYMYZUVYDCURI-LLHIWASSSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000012024 dehydrating agents Substances 0.000 claims description 15
- JFEPJTGMGDGPHJ-PNKHAZJDSA-N (8r,9s,10r,13s,14s)-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 JFEPJTGMGDGPHJ-PNKHAZJDSA-N 0.000 claims description 12
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 8
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical group C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical class 0.000 claims description 7
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000007800 oxidant agent Substances 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- LAOZHKKMOJSCKC-SQNIBIBYSA-N (8s,13s,14s)-13-methyl-1,2,3,6,7,8,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene Chemical compound C1CC2=CCCCC2=C2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 LAOZHKKMOJSCKC-SQNIBIBYSA-N 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000005336 allyloxy group Chemical group 0.000 claims description 5
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 5
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- 150000003457 sulfones Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 208000005156 Dehydration Diseases 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical group ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 claims description 2
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004965 peroxy acids Chemical group 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 19
- 208000037656 Respiratory Sounds Diseases 0.000 claims 3
- 206010037833 rales Diseases 0.000 claims 3
- ISBSSBGEYIBVTO-TYKWNDPBSA-N (20R,22R)-20,22-dihydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC2 ISBSSBGEYIBVTO-TYKWNDPBSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 230000000962 progestomimetic effect Effects 0.000 abstract description 3
- 230000001548 androgenic effect Effects 0.000 abstract description 2
- 230000002280 anti-androgenic effect Effects 0.000 abstract description 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 abstract description 2
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000004001 thioalkyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 144
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 50
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 43
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- 238000003756 stirring Methods 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- 239000000377 silicon dioxide Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000003480 eluent Substances 0.000 description 19
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- 229940088597 hormone Drugs 0.000 description 10
- 239000005556 hormone Substances 0.000 description 10
- 101150064205 ESR1 gene Proteins 0.000 description 9
- 235000019270 ammonium chloride Nutrition 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 8
- 239000003862 glucocorticoid Substances 0.000 description 8
- 238000011534 incubation Methods 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 229960003957 dexamethasone Drugs 0.000 description 7
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 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 6
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 6
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 6
- RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 6
- 229920002307 Dextran Polymers 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
- 229930006000 Sucrose Natural products 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229960005309 estradiol Drugs 0.000 description 4
- 229930182833 estradiol Natural products 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 210000004291 uterus Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 3
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 229960002478 aldosterone Drugs 0.000 description 3
- 239000008366 buffered solution Substances 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- OPHUWKNKFYBPDR-UHFFFAOYSA-N copper lithium Chemical compound [Li].[Cu] OPHUWKNKFYBPDR-UHFFFAOYSA-N 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 3
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 3
- 210000002307 prostate Anatomy 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 238000012453 sprague-dawley rat model Methods 0.000 description 3
- 229940037128 systemic glucocorticoids Drugs 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229960003604 testosterone Drugs 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 102100032187 Androgen receptor Human genes 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 2
- 241000790917 Dioxys <bee> Species 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 108090000079 Glucocorticoid Receptors Proteins 0.000 description 2
- 102100033417 Glucocorticoid receptor Human genes 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003470 adrenal cortex hormone Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 2
- 239000003098 androgen Substances 0.000 description 2
- 108010080146 androgen receptors Proteins 0.000 description 2
- 229940030486 androgens Drugs 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- XEHVFKKSDRMODV-UHFFFAOYSA-N ethynyl Chemical compound C#[C] XEHVFKKSDRMODV-UHFFFAOYSA-N 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 108091008039 hormone receptors Proteins 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 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
- HTJPDOPKPWUNBX-UHFFFAOYSA-M magnesium;2h-thiophen-2-ide;bromide Chemical compound [Mg+2].[Br-].C=1C=[C-]SC=1 HTJPDOPKPWUNBX-UHFFFAOYSA-M 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 2
- 210000001541 thymus gland Anatomy 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 2
- 229940045145 uridine Drugs 0.000 description 2
- NTPOQYZRDMWOFJ-VEXUQBRISA-N (8S,10S,13S,14S)-13-methyl-1,2,3,4,5,6,7,8,10,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene Chemical compound C[C@@]12CCC[C@H]1[C@@H]1CCC3CCCC[C@@H]3C1=CC2 NTPOQYZRDMWOFJ-VEXUQBRISA-N 0.000 description 1
- ANYFQCILKQBMST-XJESQWQHSA-N (8s,13s,14s)-13-methyl-2,4,5,6,7,8,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2CC(=O)CCC2=C2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 ANYFQCILKQBMST-XJESQWQHSA-N 0.000 description 1
- WRPPGJHBKCZHKH-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-one;hydrogen peroxide Chemical compound OO.FC(F)(F)C(=O)C(F)(F)F WRPPGJHBKCZHKH-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- FECPRIJPVRVFMN-UHFFFAOYSA-N 1-bromo-3-methoxybenzene;magnesium Chemical compound [Mg].COC1=CC=CC(Br)=C1 FECPRIJPVRVFMN-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- BGOVMHWFMVXAIR-UHFFFAOYSA-N 2-chloropropane;magnesium Chemical compound [Mg].CC(C)Cl BGOVMHWFMVXAIR-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- AUITUKWCKGNHMQ-UHFFFAOYSA-N 3-chlorobut-3-en-2-one Chemical compound CC(=O)C(Cl)=C AUITUKWCKGNHMQ-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-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
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- QGZKDVFQNNGYKY-AKLPVKDBSA-N Ammonia-N17 Chemical compound [17NH3] QGZKDVFQNNGYKY-AKLPVKDBSA-N 0.000 description 1
- 101100515513 Arabidopsis thaliana XI-E gene Proteins 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 102100038595 Estrogen receptor Human genes 0.000 description 1
- 206010020112 Hirsutism Diseases 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-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
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 108090000375 Mineralocorticoid Receptors Proteins 0.000 description 1
- 102100021316 Mineralocorticoid receptor Human genes 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 101100296027 Streptomyces rimosus oxyL gene Proteins 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- AJKNYEHIJAMGHX-UHFFFAOYSA-M [Br-].COC1=CC=CC([Mg+])=C1 Chemical compound [Br-].COC1=CC=CC([Mg+])=C1 AJKNYEHIJAMGHX-UHFFFAOYSA-M 0.000 description 1
- XJIGFXNECPBTLX-UHFFFAOYSA-N [Li]C=C(C)C Chemical compound [Li]C=C(C)C XJIGFXNECPBTLX-UHFFFAOYSA-N 0.000 description 1
- DXMAARCZJITWJZ-UHFFFAOYSA-L [Mg+2].[Br-].[Br-].CC#C Chemical compound [Mg+2].[Br-].[Br-].CC#C DXMAARCZJITWJZ-UHFFFAOYSA-L 0.000 description 1
- ADSXDBCZNVXTRD-UHFFFAOYSA-N [Mg]C1=CC=CC=C1 Chemical compound [Mg]C1=CC=CC=C1 ADSXDBCZNVXTRD-UHFFFAOYSA-N 0.000 description 1
- COTCLZIUSPWWJJ-UHFFFAOYSA-M [Na+].[O-]S(=O)=S Chemical compound [Na+].[O-]S(=O)=S COTCLZIUSPWWJJ-UHFFFAOYSA-M 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229940124558 contraceptive agent Drugs 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 1
- AVGAIPMGSIOHFZ-UHFFFAOYSA-N dichloromethane;2-propan-2-yloxypropane Chemical compound ClCCl.CC(C)OC(C)C AVGAIPMGSIOHFZ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 108010038795 estrogen receptors Proteins 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 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
- 230000003054 hormonal effect Effects 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 201000010066 hyperandrogenism Diseases 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 239000013067 intermediate product Substances 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
- 150000002576 ketones Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- WMWSRIHFAVOHSW-UHFFFAOYSA-N lithium;ethane-1,2-diamine;ethyne Chemical compound [Li+].[C-]#C.NCCN WMWSRIHFAVOHSW-UHFFFAOYSA-N 0.000 description 1
- 230000000938 luteal effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 1
- BRKADVNLTRCLOW-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=[C-]C=C1 BRKADVNLTRCLOW-UHFFFAOYSA-M 0.000 description 1
- FKUUDDGRDRPAQQ-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=C[C-]=C1 FKUUDDGRDRPAQQ-UHFFFAOYSA-M 0.000 description 1
- UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- LDYUIVOAQFHBIO-UHFFFAOYSA-N n,n-dimethylprop-1-yn-1-amine Chemical compound CC#CN(C)C LDYUIVOAQFHBIO-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UYYCVBASZNFFRX-UHFFFAOYSA-N n-propan-2-ylcyclohexanamine Chemical compound CC(C)NC1CCCCC1 UYYCVBASZNFFRX-UHFFFAOYSA-N 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000021178 picnic Nutrition 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000000757 progestagenic effect Effects 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 229940095055 progestogen systemic hormonal contraceptives Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000000717 retained effect Effects 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J61/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by contraction of only one ring by one or two atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J33/002—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C07J41/0016—Oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/0025—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa substituted in position 16
- C07J7/003—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
- C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/0065—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified
- C07J7/0075—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified substituted in position 17 alfa
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Toxicology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000486788A CA1215353A (fr) | 1982-03-01 | 1985-07-15 | PROCEDE POUR LA PREPARATION DE DERIVES DE 3-CETO 5.alpha.- HYDROXY .DELTA.9 19-NORSTEROIDES ET LES DERIVES AINSI OBTENUS |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR82-03338 | 1982-03-01 | ||
| FR8203338A FR2522328B1 (fr) | 1982-03-01 | 1982-03-01 | Nouveaux produits derives de la structure 3-ceto 4,9 19-nor steroides, leur procede de preparation et leur application comme medicaments |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000486788A Division CA1215353A (fr) | 1982-03-01 | 1985-07-15 | PROCEDE POUR LA PREPARATION DE DERIVES DE 3-CETO 5.alpha.- HYDROXY .DELTA.9 19-NORSTEROIDES ET LES DERIVES AINSI OBTENUS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1206471A true CA1206471A (fr) | 1986-06-24 |
Family
ID=9271439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000422503A Expired CA1206471A (fr) | 1982-03-01 | 1983-02-28 | Procede de preparation de nouveaux derives 3-ceto .delta.4,9 19-nor steroides |
Country Status (32)
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2528434B1 (fr) * | 1982-06-11 | 1985-07-19 | Roussel Uclaf | Nouveaux 19-nor steroides substitues en 11b et eventuellement en 2, leur procede de preparation et leur application comme medicament |
| US5182381A (en) * | 1982-03-01 | 1993-01-26 | Roussel Ulcaf | Intermediates for 3-keto-19-nor-Δ4,9 -steroids |
| FR2639045B2 (fr) * | 1982-03-01 | 1994-07-29 | Roussel Uclaf | Nouveaux produits derives de la structure 3-ceto-delta-4,9-19-nor steroides et leur application comme medicaments |
| DE3231827A1 (de) * | 1982-08-24 | 1984-03-01 | Schering AG, 1000 Berlin und 4709 Bergkamen | 11ss-aryl-17(alpha)-alkinyl-17ss-hydroxy-4,9(10)- estradien-3-on-derivate, deren herstellung und diese enthaltende pharmazeutische praeparate |
| EP0116974B1 (de) * | 1983-02-18 | 1986-10-29 | Schering Aktiengesellschaft | 11-Beta-Aryl-Estradiene, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate |
| IT1212835B (it) * | 1983-08-18 | 1989-11-30 | Lehner Ag | Derivati di acidi biliari, procedimento per la loro preparazione e relative composizioni farmaceutiche. |
| DE3347126A1 (de) * | 1983-12-22 | 1985-07-11 | Schering AG, 1000 Berlin und 4709 Bergkamen | 11ss-aryl-estradiene, deren herstellung und diese enthaltende pharmazeutische praeparate |
| US4666898A (en) * | 1983-12-28 | 1987-05-19 | Jackson Lab. | Treatment of obesity, diabetes and other symptoms of hypercorticoidism using etiocholanolones |
| DE3410880A1 (de) * | 1984-03-21 | 1985-10-03 | Schering AG, Berlin und Bergkamen, 1000 Berlin | 17-substituierte estradiene und estratriene |
| DE3438500C1 (de) * | 1984-10-18 | 1986-05-28 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur Herstellung 11ß-substituierter Δ↑9↑-19-Norsteroide |
| FR2573657B1 (fr) * | 1984-11-29 | 1989-05-12 | Roussel Uclaf | Produit comprenant une substance antiprogestomimetique et une substance uterotonique |
| FR2576025B1 (fr) * | 1985-01-14 | 1987-01-23 | Roussel Uclaf | Nouveaux steroides substitues en position 10, leur procede et les intermediaires de preparation, leur application comme medicaments, les compositions pharmaceutiques les contenant |
| AU580843B2 (en) * | 1985-02-07 | 1989-02-02 | Schering Aktiengesellschaft | 11``-phenyl-gonanes, their manufacture and pharmaceutical preparations containing them |
| CA1241947A (en) * | 1985-05-31 | 1988-09-13 | Pierre R. Proulx | Conjugated polyene sterol derivatives as membrane probes |
| GB8513723D0 (en) * | 1985-05-31 | 1985-07-03 | Erba Farmitalia | 11-beta substituted steroids |
| US4686214A (en) * | 1985-10-30 | 1987-08-11 | Alcon Laboratories, Inc. | Anti-inflammatory compounds for ophthalmic use |
| FR2598421B1 (fr) * | 1986-05-06 | 1988-08-19 | Roussel Uclaf | Nouveaux produits 19-nor ou 19-nor d-homo steroides substitues en position 11b par un radical phenyle portant un radical alkynyle, leur procede de preparation, leur application comme medicaments et les compositions les renfermant |
| DE3625315A1 (de) * | 1986-07-25 | 1988-01-28 | Schering Ag | 11ss-(4-isopropenylphenyl)-estra-4,9-diene, deren herstellung und diese enthaltende pharmazeutische praeparate |
| US4774236A (en) * | 1986-09-17 | 1988-09-27 | Research Triangle Institute | 17α-(substituted-methyl)-17β-hydroxy/esterified hydroxy steroids and pharmaceutical compositions containing them |
| US5272140A (en) * | 1987-01-23 | 1993-12-21 | Akzo N.V. | 11-aryl steroid derivatives |
| FR2610933B1 (fr) * | 1987-02-18 | 1989-06-09 | Roussel Uclaf | Nouveaux 19-nor steroides substitues en position 7, leur preparation, leur application comme medicaments, les compositions pharmaceutiques les renfermant |
| US5446178A (en) * | 1987-03-18 | 1995-08-29 | Schering Aktiengesellschaft | Process for preparing 19,11β-bridged steroids |
| DE3708942A1 (de) * | 1987-03-18 | 1988-09-29 | Schering Ag | 19,11ss-ueberbrueckte steroide, deren herstellung und diese enthaltende pharmazeutische praeparate |
| US5075464A (en) * | 1987-04-22 | 1991-12-24 | Merrell Dow Pharmaceuticals Inc. | 17β-(cyclopropylamino)androstene derivatives |
| DE3723788A1 (de) * | 1987-07-16 | 1989-01-26 | Schering Ag | 11(beta)-phenyl-4,9,15-estratriene, deren herstellung und diese enthaltende pharmazeutische praeparate |
| FR2618783B1 (fr) * | 1987-07-30 | 1991-02-01 | Roussel Uclaf | Nouveaux 17-aryle steroides, leurs procedes et des intermediaires de preparation comme medicaments et les compositions pharmaceutiques les renfermant |
| FR2620707B1 (fr) * | 1987-09-18 | 1989-12-08 | Roussel Uclaf | Nouveaux steroides comportant un cycle spirannique a 3, 4 ou 6 chainons en position 17, leur procede et des intermediaires de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
| US4954490A (en) * | 1988-06-23 | 1990-09-04 | Research Triangle Institute | 11 β-substituted progesterone analogs |
| DE3822770A1 (de) * | 1988-07-01 | 1990-01-04 | Schering Ag | 13-alkyl-11ss-phenylgonane |
| EP0369881A1 (fr) * | 1988-11-16 | 1990-05-23 | Roussel-Uclaf | Nouveaux produits dérivés de la structure 3-céto delta-4,9 19-nor stéroides et leur application comme médicaments |
| US6790971B1 (en) * | 1989-02-24 | 2004-09-14 | Aventis Pharma S.A. | 19-Nor-steroids |
| FR2665901B2 (fr) * | 1989-02-24 | 1994-07-29 | Roussel Uclaf | Nouveaux 19-nor sterouides ayant en position 11beta une chaine carbonee comportant une fonction amide, leur preparation, leur application comme medicaments. |
| FR2643638B1 (fr) * | 1989-02-24 | 1991-06-14 | Roussel Uclaf | Nouveaux 19-nor steroides ayant en position 11beta une chaine carbonee comportant une fonction amide ou carbamate, leur procede de preparation et les intermediaires de ce procede, leur application comme medicaments et les compositions pharmaceutiques les contenant |
| WO1991001958A2 (de) * | 1989-08-04 | 1991-02-21 | Schering Aktiengesellschaft Berlin Und Bergkamen | 11β-ARYL-GONA-4,9-DIEN-3-ONE |
| US5276023A (en) * | 1989-08-08 | 1994-01-04 | Roussel Uclaf | 19-nor-steroid esters |
| FR2651435A1 (fr) * | 1989-09-07 | 1991-03-08 | Roussel Uclaf | Nouvelle utilisation de composes anti-progestomimetiques. |
| FR2659233B1 (fr) * | 1990-03-06 | 1994-01-21 | Roussel Uclaf | Nouvelle utilisation de composes anti-progestomimetiques chez les animaux d'elevage. |
| DE4008584A1 (de) * | 1990-03-15 | 1991-09-26 | Schering Ag | Verfahren zur herstellung von zwischenprodukten fuer die antigestagensynthese (onapristonsynthese) |
| DE4042004A1 (de) * | 1990-12-22 | 1992-06-25 | Schering Ag | 14(beta)-h-, 14- u. 15-en-11(beta)-aryl-4-estrene |
| US5407928A (en) * | 1990-08-15 | 1995-04-18 | Schering Aktiengesellschaft | 11β-aryl-gona-4,9-dien-3-ones |
| JP3029907B2 (ja) * | 1991-12-20 | 2000-04-10 | 理化学研究所 | 抗肥満剤 |
| JP3862295B2 (ja) * | 1993-09-30 | 2006-12-27 | 独立行政法人理化学研究所 | 抗肥満剤 |
| US5420120A (en) * | 1993-12-17 | 1995-05-30 | Alcon Laboratories, Inc. | Anti-inflammatory glucocorticoid compounds for topical ophthalmic use |
| US5780220A (en) * | 1994-05-19 | 1998-07-14 | Trustees Of The University Of Pennsylvania | Methods and compositions for inhibiting HIV replication |
| EP0683172B1 (en) * | 1994-05-19 | 1997-08-13 | Akzo Nobel N.V. | 11,21-Bisphenyl-19-norpregnane derivatives |
| US5639598A (en) * | 1994-05-19 | 1997-06-17 | The Trustees Of The University Of Pennsylvania | Method and kit for identification of antiviral agents capable of abrogating HIV Vpr-Rip-1 binding interactions |
| DE4434488A1 (de) * | 1994-09-14 | 1996-03-21 | Schering Ag | Steroidester und -amide, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung |
| US5929262A (en) * | 1995-03-30 | 1999-07-27 | The United States Of America As Represented By The Department Of Health And Human Services | Method for preparing 17α-acetoxy-11β-(4-N, N-dimethylaminophyl)-19-Norpregna-4,9-diene-3, 20-dione, intermediates useful in the method, and methods for the preparation of such intermediates |
| IL118974A (en) * | 1995-08-17 | 2001-09-13 | Akzo Nobel Nv | History 11 - (Transformed Phenyl) - Astra - 4, 9 - Diane, their preparation and pharmaceutical preparations containing them |
| US6900193B1 (en) * | 1996-05-01 | 2005-05-31 | The United States Of America As Represented By The Department Of Health And Human Services | Structural modification of 19-norprogesterone I: 17-α-substituted-11-β-substituted-4-aryl and 21-substituted 19-norpregnadienedione as new antiprogestational agents |
| JP4260886B2 (ja) * | 1996-05-01 | 2009-04-30 | アメリカ合衆国 | 新規の抗プロゲステロンとしての２１―置換プロゲステロン誘導体 |
| IL122740A (en) * | 1997-01-15 | 2003-09-17 | Akzo Nobel Nv | 16-hydroxy-11-(substituted phenyl)-estra-9,4-diene derivatives, their preparation and pharmaceutical compositions containing them |
| DE19745085A1 (de) * | 1997-10-11 | 1999-04-15 | Jenapharm Gmbh | 11ß-Benzaldoxim-9alpha,10alpha-epoxy-estr-4-en-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate |
| US6531462B2 (en) | 1997-11-06 | 2003-03-11 | Riken | Medicament for treating obesity and improving lipid metabolism |
| JP3873097B2 (ja) * | 1997-11-06 | 2007-01-24 | 独立行政法人理化学研究所 | 抗肥満剤及び脂質代謝改善剤 |
| US6020328A (en) | 1998-03-06 | 2000-02-01 | Research Triangle Institute | 20-keto-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties |
| US6262042B1 (en) | 1998-05-29 | 2001-07-17 | Research Triangle Institute | 17β-amino and hydroxylamino-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties |
| EP2348031B9 (en) * | 2000-03-17 | 2016-08-10 | The Government of the United States of America as represented by the Secretary of the Department of Health and Human Services | 17-Alpha-substituted-11-beta-substituted-4-aryl and 21-substituted 19-norpregnadienediones as antiprogestational agents |
| US7250408B2 (en) * | 2002-12-16 | 2007-07-31 | Bayer Schering Pharma Ag | Glucocorticoid receptor antagonists for prophylaxis and therapy of glucocorticoid-mediated hypogonadism, of sexual dysfunction and/or infertility |
| JP2006519255A (ja) * | 2003-02-28 | 2006-08-24 | アメリカ合衆国 | １７α−アセトキシ−１１β−（４−Ｎ，Ｎ−ジメチルアミノフェニル）−１９−ノルプレグナ−４，９−ジエン−３，２０−ジオンの製造方法、その中間体及びそのような中間体の製造方法 |
| WO2004112720A2 (en) * | 2003-06-20 | 2004-12-29 | Viral Genomix, Inc. | Antiviral compositions and methods of using the same |
| TWI477276B (zh) | 2008-04-28 | 2015-03-21 | Repros Therapeutics Inc | 抗黃體素給藥方案 |
| DE102009034525A1 (de) * | 2009-07-21 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-aryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| SG183924A1 (en) * | 2010-03-22 | 2012-10-30 | Repros Therapeutics Inc | Compositions and methods for non-toxic delivery of antiprogestins |
| PL2576582T3 (pl) | 2010-05-26 | 2020-06-29 | Corcept Therapeutics, Inc. | Leczenie dystrofii mięśniowej |
| KR102127348B1 (ko) | 2012-05-31 | 2020-06-29 | 앨러간 파마슈티컬스 인터내셔널 리미티드 | 항-프로게스틴의 경질 전달을 위한 제제 및 방법 |
| HK1211852A1 (en) | 2012-11-02 | 2016-06-03 | Repros Therapeutics Inc. | Methods and compositions for treating progesterone-dependent conditions |
| WO2015089338A2 (en) | 2013-12-11 | 2015-06-18 | Sloan-Kettering Institute For Cancer Research | Glucocorticoid inhibitors for treatment of prostate cancer |
| JP6821582B2 (ja) | 2015-03-02 | 2021-01-27 | コーセプト セラピューティクス， インコーポレイテッド | Ａｃｔｈ分泌腫瘍を処置するための糖質コルチコイドレセプターアンタゴニストおよびソマトスタチンアナログの使用 |
| EP3277281B1 (en) | 2015-03-30 | 2022-01-05 | Corcept Therapeutics, Inc. | Use of glucocorticoid receptor antagonists in combination with glucocorticoids to treat adrenal insufficiency |
| AU2016305092B2 (en) | 2015-08-13 | 2022-01-27 | Corcept Therapeutics, Inc. | Method for differentially diagnosing ACTH-dependent Cushing's syndrome |
| CN108699102A (zh) | 2015-12-23 | 2018-10-23 | 欧瑞克制药公司 | 糖皮质激素受体抑制剂 |
| CA3009525A1 (en) | 2015-12-23 | 2017-06-29 | Oric Pharmaceuticals, Inc. | Inhibitors of glucocorticoid receptor |
| US11110103B2 (en) | 2015-12-23 | 2021-09-07 | Oric Pharmaceuticals, Inc. | Inhibitors of glucocorticoid receptor |
| AU2017210156B2 (en) | 2016-01-19 | 2021-10-28 | Corcept Therapeutics, Inc. | Differential diagnosis of Ectopic Cushing's Syndrome |
| EP3851444A1 (en) | 2016-10-07 | 2021-07-21 | Oric Pharmaceuticals, Inc. | Inhibitors of glucocorticoid receptor |
| UA127409C2 (uk) | 2017-03-31 | 2023-08-16 | Корцепт Терап'Ютікс, Інк. | Модулятори глюкокортикоїдного рецептора для лікування раку шийки матки |
| JP7670462B2 (ja) | 2017-06-20 | 2025-04-30 | コーセプト セラピューティクス， インコーポレイテッド | 選択的グルココルチコイドレセプターモジュレーターを使用して神経上皮腫瘍を処置する方法 |
| CA3205462A1 (en) | 2020-12-18 | 2022-06-23 | Instil Bio (Uk) Limited | Processing of tumor infiltrating lymphocytes |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH571537A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1970-04-24 | 1976-01-15 | Sandoz Ag | |
| CH558346A (de) * | 1971-06-17 | 1975-01-31 | Sandoz Ag | Verfahren zur herstellung neuer 3-oximino-17(alpha)-propadienyl-substituierter steroide. |
| BE787898A (fr) * | 1971-08-26 | 1973-02-23 | Roussel Uclaf | Nouveaux composes steroides trieniques et procede de preparation |
| DE2636405C2 (de) * | 1976-08-12 | 1982-07-08 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Δ↑1↑↑5↑-17α-Chloräthinyl- und -Propinylsteroide der Östranreihe, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Präparate |
| FR2377418A1 (fr) * | 1977-01-13 | 1978-08-11 | Roussel Uclaf | Nouveaux derives steroides 4,9-dieniques 11b-substitues, leur procede de preparation et leur application comme medicaments |
| FR2377417A1 (fr) * | 1977-01-13 | 1978-08-11 | Roussel Uclaf | Nouveaux derives steroides substitues en 11b, ainsi que leur procede de preparation |
| FR2377419A1 (fr) * | 1977-01-13 | 1978-08-11 | Roussel Uclaf | Nouveaux derives steroides 11b-substitues 1,3,5 (10) trieniques, leur procede de preparation et leur application comme medicament |
| FR2495621A1 (fr) * | 1980-12-05 | 1982-06-11 | Roussel Uclaf | Nouveaux derives de l'estra 4,9-diene, leur procede de preparation et leur application comme medicaments |
| ZA8231B (en) * | 1981-01-09 | 1982-11-24 | Roussel Uclaf | New 11 -substituted steroid derivatives, their preparation, their use as medicaments, the compositions containing them and the new intermediates thus obtained |
-
1982
- 1982-03-01 FR FR8203338A patent/FR2522328B1/fr not_active Expired
-
1983
- 1983-01-21 SE SE8300308A patent/SE8300308L/ unknown
- 1983-02-11 MA MA19934A patent/MA19716A1/fr unknown
- 1983-02-14 ZA ZA83982A patent/ZA83982B/xx unknown
- 1983-02-15 IL IL67920A patent/IL67920A0/xx not_active IP Right Cessation
- 1983-02-23 US US06/469,042 patent/US4477445A/en not_active Expired - Fee Related
- 1983-02-23 PH PH28558A patent/PH21308A/en unknown
- 1983-02-25 DK DK89783A patent/DK89783A/da not_active Application Discontinuation
- 1983-02-25 WO PCT/FR1983/000034 patent/WO1983003099A1/en unknown
- 1983-02-25 GR GR70610A patent/GR78465B/el unknown
- 1983-02-27 EG EG133/83A patent/EG15881A/xx active
- 1983-02-28 SU SU833561503A patent/SU1340593A3/ru active
- 1983-02-28 FI FI830652A patent/FI80049C/fi not_active IP Right Cessation
- 1983-02-28 BE BE0/210223A patent/BE896042A/fr not_active IP Right Cessation
- 1983-02-28 YU YU00478/83A patent/YU47883A/xx unknown
- 1983-02-28 CH CH1099/83A patent/CH657368A5/fr not_active IP Right Cessation
- 1983-02-28 IT IT47820/83A patent/IT1197592B/it active
- 1983-02-28 MX MX8310507U patent/MX7199E/es unknown
- 1983-02-28 AU AU11913/83A patent/AU562739B2/en not_active Ceased
- 1983-02-28 CA CA000422503A patent/CA1206471A/fr not_active Expired
- 1983-02-28 LU LU84667A patent/LU84667A1/fr unknown
- 1983-02-28 KR KR1019830000853A patent/KR880001870B1/ko not_active Expired
- 1983-02-28 PT PT76307A patent/PT76307B/pt not_active IP Right Cessation
- 1983-02-28 NL NL8300738A patent/NL8300738A/nl not_active Application Discontinuation
- 1983-03-01 AR AR83292260A patent/AR241187A1/es active
- 1983-03-01 IE IE429/83A patent/IE54748B1/en not_active IP Right Cessation
- 1983-03-01 JP JP58031909A patent/JPS58201800A/ja active Granted
- 1983-03-01 HU HU83690A patent/HU193269B/hu not_active IP Right Cessation
- 1983-03-01 GB GB08305558A patent/GB2118186B/en not_active Expired
- 1983-03-01 ES ES520195A patent/ES520195A0/es active Granted
- 1983-03-01 AT AT0071183A patent/AT396109B/de not_active IP Right Cessation
- 1983-03-01 DE DE19833307143 patent/DE3307143A1/de not_active Withdrawn
-
1984
- 1984-06-08 US US06/618,590 patent/US4540686A/en not_active Expired - Fee Related
-
1990
- 1990-02-28 JP JP2046023A patent/JPH02275895A/ja active Granted
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1206471A (fr) | Procede de preparation de nouveaux derives 3-ceto .delta.4,9 19-nor steroides | |
| EP0196707B1 (fr) | Nouveaux 19-nor stéroides substitués en 11, en 17 et éventuellement en 2, leur préparation, leur application comme médicaments, les compositions les renfermant et les nouveaux intermédiaires obtenus | |
| EP0057115B1 (fr) | Nouveaux dérivés stéroides substitués en 11beta, procédé de préparation, leur application comme médicament et les compositions les renfermant | |
| CA1340342C (fr) | 17-aryle steroides, leur procede et intermediaires de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant | |
| EP0262188B1 (fr) | Steroides comportant un cycle spirannique en position 17, leur procede de preparation et leur utilisation | |
| EP0308345B1 (fr) | Nouveaux stéroides comportant un cycle spirannique à 3, 4 ou 6 chaînons en position 17, leur procédé et des intermédiaires de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant | |
| EP0245170B1 (fr) | Nouveaux produits 19-nor ou 19-nor D-homo stéroides substitués en position 11 beta par un radical phényle portant un radical alkynile, leur procédé de préparation, leur application comme médicaments et les compositions les renfermant | |
| EP0188396B1 (fr) | Nouveaux stéroides substitués en position 10, leur procédé et les intermédiaires de préparation, leur application comme médicaments, les compositions pharmaceutiques les contenant | |
| CA2090584C (fr) | Steroides comportant en position 17 un radical methylene lactone, leur procede et des intermediaires de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant | |
| CA2010826A1 (fr) | 19-nor steroides ayant en position 11beta une chaine carbonee comportant une fonction amide ou carbamate, leur procede de preparation et les intermediaires de ce procede, leur application comme medicaments et les compositions pharmaceutiques les contenant | |
| EP0176399B1 (fr) | Nouveaux stéroides substitués en position 10 par un radical comportant une double ou triple liaison, leur procédé de préparation, leur application comme médicaments, les compositions pharmaceutiques les renfermant | |
| EP0056000B1 (fr) | Dérivés 17/(alkoxycarbonyle) (formamido) méthylène/stéroides et leur préparation | |
| EP0515264B1 (fr) | Nouveaux dérivés stéroides du pregna-4,9(11),17(20)-triène-3-one, leur préparation, leur préparation, leur application à la préparation de composés stéroides de type pregna-4,9(11),16-trièn-3,20-dione et nouveaux intermédiaires | |
| FR2586021A1 (fr) | Nouveaux produits derives de la structure 5a-oh d 9(10) 19-nor steroides | |
| EP0087359B1 (fr) | Nouveau réactif de nitrométhylation, son application à la préparation de composés nitrométhylénés et de certains de leurs dérivés et les composés nouveaux obtenus | |
| EP0110434B1 (fr) | Nouveaux produits intermédiaires stéroides substitués en 11-beta et procédé de préparation de ces produits | |
| CA1146531A (fr) | Procede de preparation de nouveaux derives 2,2- dimethyl 19-nor steroides | |
| WO1985001504A1 (fr) | NOUVEAU PROCEDE DE PREPARATION DE DERIVES DE LA SERIE DE LA 17alpha-HYDROXY 19-NOR-PROGESTERONE | |
| CA1199907A (fr) | PROCEDE POUR LA PREPARATION DE DERIVES DE STEROIDES HYDROXYLES EN 5.alpha., ET LES DERIVES AINSI OBTENUS | |
| CH629826A5 (en) | Steroids, process for preparing them and their use in the synthesis of tritium-labelled steroids | |
| CA1215353A (fr) | PROCEDE POUR LA PREPARATION DE DERIVES DE 3-CETO 5.alpha.- HYDROXY .DELTA.9 19-NORSTEROIDES ET LES DERIVES AINSI OBTENUS |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |