NO325180B1 - Fremgangsmate for fremstilling av 3-okso-4-azasteroid og anvendelse derav - Google Patents
Fremgangsmate for fremstilling av 3-okso-4-azasteroid og anvendelse derav Download PDFInfo
- Publication number
- NO325180B1 NO325180B1 NO20031995A NO20031995A NO325180B1 NO 325180 B1 NO325180 B1 NO 325180B1 NO 20031995 A NO20031995 A NO 20031995A NO 20031995 A NO20031995 A NO 20031995A NO 325180 B1 NO325180 B1 NO 325180B1
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- alkyl
- branched
- trifluoromethyl
- linear
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 47
- 238000002360 preparation method Methods 0.000 title claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000005695 Ammonium acetate Substances 0.000 claims description 12
- 235000019257 ammonium acetate Nutrition 0.000 claims description 12
- 229940043376 ammonium acetate Drugs 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 229940123934 Reductase inhibitor Drugs 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- LTCAWJFJFVGUNT-TZUPDSNESA-N (3as,3bs,9ar,9bs,11as)-9a,11a-dimethyl-1,2,3,3a,3b,4,6,8,9,9b,10,11-dodecahydroindeno[5,4-f]quinolin-7-one Chemical group C1C=C2NC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 LTCAWJFJFVGUNT-TZUPDSNESA-N 0.000 claims description 6
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 6
- XJMWHXZUIGHOBA-UHFFFAOYSA-N azane;propanoic acid Chemical compound N.CCC(O)=O XJMWHXZUIGHOBA-UHFFFAOYSA-N 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- -1 2,5-bis(trifluoromethyl)phenyl Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- MOVIKFRNYOCODR-TZUPDSNESA-N (3aS,3bS,9aR,9bS,11aS)-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9b,10,11-dodecahydroindeno[5,4-f]quinolin-7-one Chemical compound [C@@H]12CCC[C@@]1(C)CC[C@H]1[C@H]2CCC2=NC(CC[C@]12C)=O MOVIKFRNYOCODR-TZUPDSNESA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 238000005984 hydrogenation reaction Methods 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 150000003431 steroids Chemical class 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910004373 HOAc Inorganic materials 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical group N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 230000003637 steroidlike Effects 0.000 description 2
- 229960003604 testosterone Drugs 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RZYHXKLKJRGJGP-UHFFFAOYSA-N 2,2,2-trifluoro-n,n-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)N([Si](C)(C)C)C(=O)C(F)(F)F RZYHXKLKJRGJGP-UHFFFAOYSA-N 0.000 description 1
- XWMVIJUAZAEWIE-UHFFFAOYSA-N 2,5-bis(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1C(F)(F)F XWMVIJUAZAEWIE-UHFFFAOYSA-N 0.000 description 1
- 239000002677 5-alpha reductase inhibitor Substances 0.000 description 1
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 1
- 150000000583 5α-androstanes Chemical class 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010020112 Hirsutism Diseases 0.000 description 1
- XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 206010068168 androgenetic alopecia Diseases 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229960004039 finasteride Drugs 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229940072254 proscar Drugs 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YCODFDNOIPXYRI-UHFFFAOYSA-N trimethyl-[2-(methylamino)ethyl]azanium Chemical compound CNCC[N+](C)(C)C YCODFDNOIPXYRI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Valve Device For Special Equipments (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0026876.3A GB0026876D0 (en) | 2000-11-03 | 2000-11-03 | Process |
PCT/US2001/048173 WO2002046207A2 (fr) | 2000-11-03 | 2001-11-02 | Procede |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20031995D0 NO20031995D0 (no) | 2003-05-02 |
NO20031995L NO20031995L (no) | 2003-05-02 |
NO325180B1 true NO325180B1 (no) | 2008-02-11 |
Family
ID=9902484
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20031995A NO325180B1 (no) | 2000-11-03 | 2003-05-02 | Fremgangsmate for fremstilling av 3-okso-4-azasteroid og anvendelse derav |
Country Status (24)
Country | Link |
---|---|
US (1) | US6794508B2 (fr) |
EP (1) | EP1335930B1 (fr) |
JP (1) | JP4257117B2 (fr) |
KR (1) | KR100821018B1 (fr) |
CN (1) | CN1313480C (fr) |
AT (1) | ATE279429T1 (fr) |
AU (2) | AU4162402A (fr) |
BR (1) | BR0115089A (fr) |
CA (1) | CA2427709A1 (fr) |
DE (1) | DE60106482T2 (fr) |
DK (1) | DK1335930T3 (fr) |
ES (1) | ES2230383T3 (fr) |
GB (1) | GB0026876D0 (fr) |
HK (1) | HK1058799A1 (fr) |
HU (1) | HUP0303907A3 (fr) |
IL (2) | IL155078A0 (fr) |
MX (1) | MXPA03003925A (fr) |
NO (1) | NO325180B1 (fr) |
NZ (1) | NZ525168A (fr) |
PL (1) | PL206539B1 (fr) |
PT (1) | PT1335930E (fr) |
SI (1) | SI1335930T1 (fr) |
WO (1) | WO2002046207A2 (fr) |
ZA (1) | ZA200302560B (fr) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100503193B1 (ko) * | 2002-08-19 | 2005-07-25 | 한미약품 주식회사 | 3-옥소-4-아자-5α-안드로스탄 화합물의 선택적인 제조방법 |
WO2005075497A1 (fr) * | 2004-01-07 | 2005-08-18 | Ranbaxy Laboratories Limited | PROCEDE DE PREPARATION DE DERIVES DE 17ss-SUBSTITUE-3-OXO-4-AZA-5ALPHA-ANDROSTANE |
CN100355772C (zh) * | 2005-12-28 | 2007-12-19 | 天津大学 | 具有5α-还原酶抑制活性的甾体化合物及其制备方法 |
AR070313A1 (es) * | 2008-01-03 | 2010-03-31 | Gador Sa | Un procedimiento para preparar una forma solida y cristalina de dutasteride, una forma polimorfica del compuesto (forma iii) y una composicion farmaceutica que incluye dicha forma |
HU230730B1 (hu) | 2011-06-30 | 2017-12-28 | Richter Gedeon Nyrt | Eljárás (5alfa,17béta)-N-[2,5-bisz-(trifluormetil)-fenil]-3-oxo-4-aza-5-androszt-1-én-17-karbonsavamid előállítására |
CN103059097A (zh) * | 2011-10-20 | 2013-04-24 | 连云港润众制药有限公司 | 一种度他雄胺中间体的制备方法 |
CN103254268A (zh) * | 2013-05-16 | 2013-08-21 | 寿光市富康化学工业有限公司 | 一种制备度他雄胺的工艺 |
CN104231033B (zh) * | 2014-09-17 | 2016-08-24 | 广东众生药业股份有限公司 | 一种度他雄胺的制备方法 |
CN108051513B (zh) * | 2017-11-27 | 2020-09-29 | 重庆华邦制药有限公司 | Hplc法分离测定度他雄胺起始原料sm2及其相关杂质的方法 |
CN109438549B (zh) * | 2018-12-13 | 2022-01-04 | 湖北葛店人福药业有限责任公司 | 一种制备N-叔丁基-3-氧代-4-氮杂-5α-雄甾-17β-甲酰胺的方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ211145A (en) * | 1984-02-27 | 1988-10-28 | Merck & Co Inc | 4-aza-5-alpha-androst-1-en-3-ones and pharmaceutical compositions |
GB2264494A (en) * | 1992-02-25 | 1993-09-01 | Merck & Co Inc | 17b-n-monosubstituted carbamoyl-11-oxo-4-aza-5-a-androst-1-en-3-one testosterone-5-alpha reductase inhibitors |
TW408127B (en) * | 1993-09-17 | 2000-10-11 | Glaxo Inc | Androstenones |
-
2000
- 2000-11-03 GB GBGB0026876.3A patent/GB0026876D0/en not_active Ceased
-
2001
- 2001-11-02 ES ES01988307T patent/ES2230383T3/es not_active Expired - Lifetime
- 2001-11-02 DK DK01988307T patent/DK1335930T3/da active
- 2001-11-02 BR BR0115089-8A patent/BR0115089A/pt not_active Application Discontinuation
- 2001-11-02 SI SI200130241T patent/SI1335930T1/xx unknown
- 2001-11-02 EP EP01988307A patent/EP1335930B1/fr not_active Expired - Lifetime
- 2001-11-02 IL IL15507801A patent/IL155078A0/xx unknown
- 2001-11-02 AT AT01988307T patent/ATE279429T1/de active
- 2001-11-02 KR KR1020037006176A patent/KR100821018B1/ko not_active IP Right Cessation
- 2001-11-02 JP JP2002547944A patent/JP4257117B2/ja not_active Expired - Fee Related
- 2001-11-02 WO PCT/US2001/048173 patent/WO2002046207A2/fr active IP Right Grant
- 2001-11-02 PT PT01988307T patent/PT1335930E/pt unknown
- 2001-11-02 PL PL365705A patent/PL206539B1/pl not_active IP Right Cessation
- 2001-11-02 NZ NZ525168A patent/NZ525168A/en not_active IP Right Cessation
- 2001-11-02 MX MXPA03003925A patent/MXPA03003925A/es active IP Right Grant
- 2001-11-02 HU HU0303907A patent/HUP0303907A3/hu unknown
- 2001-11-02 AU AU4162402A patent/AU4162402A/xx active Pending
- 2001-11-02 DE DE60106482T patent/DE60106482T2/de not_active Expired - Lifetime
- 2001-11-02 US US10/415,922 patent/US6794508B2/en not_active Expired - Fee Related
- 2001-11-02 AU AU2002241624A patent/AU2002241624B2/en not_active Ceased
- 2001-11-02 CA CA002427709A patent/CA2427709A1/fr not_active Abandoned
- 2001-11-02 CN CNB018184960A patent/CN1313480C/zh not_active Expired - Fee Related
-
2003
- 2003-03-25 IL IL155078A patent/IL155078A/en not_active IP Right Cessation
- 2003-04-01 ZA ZA200302560A patent/ZA200302560B/en unknown
- 2003-05-02 NO NO20031995A patent/NO325180B1/no not_active IP Right Cessation
-
2004
- 2004-01-14 HK HK04100269A patent/HK1058799A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101245727B1 (ko) | 아비라테론―3―에스테르의 메탄설포네이트 염, 및 메틸3차―부틸 에테르 중의 용액으로부터아비라테론―3―에스테르의 염의 회수 | |
AT396239B (de) | Verfahren zur herstellung von neuen in 4-stellung substituierten androstendionderivaten | |
EP3190121B1 (fr) | Procédés de réduction stéréo-sélective du derivé 4-en-3-one de cyclopamine | |
NO325180B1 (no) | Fremgangsmate for fremstilling av 3-okso-4-azasteroid og anvendelse derav | |
JP2018008985A (ja) | (5−フルオロ−2−メチル−3−キノリン−2−イルメチル−インドール−1−イル)−酢酸エステルの製造のための方法 | |
CA2171329C (fr) | Androstenones | |
AU2002241624A1 (en) | Process | |
KR101446825B1 (ko) | 아로마타제 억제제의 제조 방법 | |
EP2414378B1 (fr) | Separation d'acide 4-aza-androst-1-ène-17-oïque de l'acide 4-aza-androstan-17-oïque | |
JPH06501272A (ja) | 17β−置換−4−アザ−5α−アンドロスタン−3−オン誘導体の製法 | |
US6187925B1 (en) | Intermediates and process for the synthesis of azasteroids | |
US5583228A (en) | 17-halogeno-4-azaandrostene derivatives and process for the preparation thereof | |
EP2215104B1 (fr) | 11 -fluoro-3-acétoxyestra-3,5-diène-17-one, et son procédé de fabrication |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |