KR850000969B1 - 안드로스탄 카보티오에이트의 제조방법 - Google Patents

안드로스탄 카보티오에이트의 제조방법 Download PDF

Info

Publication number: KR850000969B1
Authority: KR; South Korea
Prior art keywords: hydroxy; diene; solution; methyl; ethyl acetate
Prior art date: 1980-02-15

Application number

KR1019810000442A

Other languages

English (en)

Korean (ko)

Other versions

KR830005262A (ko

Inventor

헨리 필립스 고든

맥도날드 베인 브리안

윌리암슨 크리스토퍼

필립 스티플스 이안

브루스 레잉 스투워트

Original Assignee

글락소 그룹 리미티드

배리 안소니뉴샘

Priority date (The priority date 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 date listed.)

1980-02-15

Filing date

1981-02-13

Publication date

1985-07-02

1981-02-13 Application filed by 글락소 그룹 리미티드, 배리 안소니뉴샘 filed Critical 글락소 그룹 리미티드

1983-08-03 Publication of KR830005262A publication Critical patent/KR830005262A/ko

1985-07-02 Application granted granted Critical

1985-07-02 Publication of KR850000969B1 publication Critical patent/KR850000969B1/ko

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HPRZMZVRGNSDEC-WPVJXYFRSA-N (5S,8S,9S,10R,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-4-carbothioic S-acid Chemical class [C@@H]12CCC[C@@]1(C)CC[C@H]1[C@H]2CC[C@H]2C(CCC[C@]12C)C(O)=S HPRZMZVRGNSDEC-WPVJXYFRSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 58
-1 fluoro- Chemical class 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 8
239000003153 chemical reaction reagent Substances 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 276
239000000243 solution Substances 0.000 description 117
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 94
235000019439 ethyl acetate Nutrition 0.000 description 92
229940093499 ethyl acetate Drugs 0.000 description 92
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 85
238000002844 melting Methods 0.000 description 81
230000008018 melting Effects 0.000 description 81
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 75
239000002253 acid Substances 0.000 description 56
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
239000002904 solvent Substances 0.000 description 36
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 33
239000000203 mixture Substances 0.000 description 30
229910052757 nitrogen Inorganic materials 0.000 description 30
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
238000000034 method Methods 0.000 description 26
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
238000002360 preparation method Methods 0.000 description 24
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 24
239000007787 solid Substances 0.000 description 24
239000000284 extract Substances 0.000 description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 22
239000006260 foam Substances 0.000 description 22
239000000047 product Substances 0.000 description 21
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
238000002425 crystallisation Methods 0.000 description 16
230000008025 crystallization Effects 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
235000017557 sodium bicarbonate Nutrition 0.000 description 16
229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
238000003756 stirring Methods 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 13
229910000029 sodium carbonate Inorganic materials 0.000 description 13
239000000725 suspension Substances 0.000 description 13
OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
150000008064 anhydrides Chemical class 0.000 description 10
230000003110 anti-inflammatory effect Effects 0.000 description 10
238000000354 decomposition reaction Methods 0.000 description 10
238000009835 boiling Methods 0.000 description 9
239000000377 silicon dioxide Substances 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
235000009518 sodium iodide Nutrition 0.000 description 8
239000007858 starting material Substances 0.000 description 8
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
229910000037 hydrogen sulfide Inorganic materials 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000011734 sodium Substances 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
230000000699 topical effect Effects 0.000 description 7
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 6
239000012267 brine Substances 0.000 description 6
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
238000001035 drying Methods 0.000 description 6
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
229940096017 silver fluoride Drugs 0.000 description 6
REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 6
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
239000005909 Kieselgur Substances 0.000 description 5
239000012043 crude product Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
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 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
239000000523 sample Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
150000001441 androstanes Chemical class 0.000 description 3
239000006286 aqueous extract Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
125000005997 bromomethyl group Chemical group 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
239000011575 calcium Substances 0.000 description 3
JUIFJMUPAOYEHW-UHFFFAOYSA-N chloromethanethiol Chemical compound SCCl JUIFJMUPAOYEHW-UHFFFAOYSA-N 0.000 description 3
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
GPNHMOZDMYNCPO-PDUMRIMRSA-N clascoterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CO)(OC(=O)CC)[C@@]1(C)CC2 GPNHMOZDMYNCPO-PDUMRIMRSA-N 0.000 description 3
239000006071 cream Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
150000002367 halogens Chemical group 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 3
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000012265 solid product Substances 0.000 description 3
PBXJGQQGODZSQR-CWQDBKDDSA-N (8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-17-carboxylic acid Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(O)=O)[C@@H]4[C@@H]3CCC21 PBXJGQQGODZSQR-CWQDBKDDSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
0 CCCCC(C=C(C1)[C@@]2(*)*C11C(*)CC3(C)C(*)(*)C(*)CC3C1C2)O Chemical compound CCCCC(C=C(C1)[C@@]2(*)*C11C(*)CC3(C)C(*)(*)C(*)CC3C1C2)O 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
201000004624 Dermatitis Diseases 0.000 description 2
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
239000004593 Epoxy Substances 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
229910052805 deuterium Inorganic materials 0.000 description 2
238000010828 elution Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
238000009472 formulation Methods 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
238000011084 recovery Methods 0.000 description 2
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
235000019345 sodium thiosulphate Nutrition 0.000 description 2
150000003431 steroids Chemical class 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
238000011200 topical administration Methods 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HXXNSZGESRDYFE-JIUSCHCVSA-N 1-[(8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC21 HXXNSZGESRDYFE-JIUSCHCVSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
LWYSMSHCTRLEHY-UHFFFAOYSA-M 2-chloro-3-methyl-1,3-benzothiazol-3-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=C2[N+](C)=C(Cl)SC2=C1 LWYSMSHCTRLEHY-UHFFFAOYSA-M 0.000 description 1
HQWDKLAIDBOLFE-UHFFFAOYSA-M 2-fluoro-1-methylpyridin-1-ium;4-methylbenzenesulfonate Chemical compound C[N+]1=CC=CC=C1F.CC1=CC=C(S([O-])(=O)=O)C=C1 HQWDKLAIDBOLFE-UHFFFAOYSA-M 0.000 description 1
SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 description 1
MYYIMZRZXIQBGI-HVIRSNARSA-N 6alpha-Fluoroprednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3C[C@H](F)C2=C1 MYYIMZRZXIQBGI-HVIRSNARSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QHPRZCKDHZNGRS-UDCWSGSHSA-N C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(O)=S)[C@@H]4[C@@H]3CCC2=C1 Chemical compound C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(O)=S)[C@@H]4[C@@H]3CCC2=C1 QHPRZCKDHZNGRS-UDCWSGSHSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
241000425361 Chlorodium Species 0.000 description 1
241000400611 Eucalyptus deanei Species 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
239000003810 Jones reagent Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000003251 Pruritus Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000003470 adrenal cortex hormone Substances 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001516 alkali metal iodide Inorganic materials 0.000 description 1
229910001619 alkaline earth metal iodide Inorganic materials 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229940107816 ammonium iodide Drugs 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
239000002585 base Substances 0.000 description 1
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
238000007664 blowing Methods 0.000 description 1
FNXLCIKXHOPCKH-UHFFFAOYSA-N bromamine Chemical compound BrN FNXLCIKXHOPCKH-UHFFFAOYSA-N 0.000 description 1
150000003842 bromide salts Chemical class 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000005998 bromoethyl group Chemical group 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
ZYZWOSIRFVIBRH-UHFFFAOYSA-N chloroform;cyclohexane Chemical compound ClC(Cl)Cl.C1CCCCC1 ZYZWOSIRFVIBRH-UHFFFAOYSA-N 0.000 description 1
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical group CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
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 1
239000013058 crude material Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
ZXSBDSGRQIWJPM-UHFFFAOYSA-N dimethylcarbamothioic s-acid Chemical compound CN(C)C(S)=O ZXSBDSGRQIWJPM-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
QAELBUPWYLAZOK-UHFFFAOYSA-N fluoromethanethiol Chemical compound FCS QAELBUPWYLAZOK-UHFFFAOYSA-N 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 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
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
UVVXUXXBNILMOS-UHFFFAOYSA-N o-(dimethylcarbamothioyl) n,n-dimethylcarbamothioate Chemical compound CN(C)C(=S)OC(=S)N(C)C UVVXUXXBNILMOS-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 1
JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 1
238000004237 preparative chromatography Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
PNYYBUOBTVHFDN-UHFFFAOYSA-N sodium bismuthate Chemical compound [Na+].[O-][Bi](=O)=O PNYYBUOBTVHFDN-UHFFFAOYSA-N 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- 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
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
- 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
- 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
- C07J41/0038—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide group
- 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
- 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
- C07J71/0015—Oxiranes at position 9(11)
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

KR1019810000442A 1980-02-15 1981-02-13 안드로스탄 카보티오에이트의 제조방법 KR850000969B1 (ko)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB8005174		1980-02-15
GB8005174		1980-02-15
GB8013339		1980-04-23
GB8013339		1980-04-23

Publications (2)

Publication Number	Publication Date
KR830005262A KR830005262A (ko)	1983-08-03
KR850000969B1 true KR850000969B1 (ko)	1985-07-02

Family

ID=26274505

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
KR1019810000442A KR850000969B1 (ko)	1980-02-15	1981-02-13	안드로스탄 카보티오에이트의 제조방법

Country Status (23)

Country	Link
KR (1)	KR850000969B1 (pt)
AT (1)	AT395427B (pt)
AU (1)	AU544517B2 (pt)
BG (1)	BG60700B2 (pt)
CH (2)	CH651307A5 (pt)
CZ (1)	CZ281275B6 (pt)
DE (2)	DE3153379C2 (pt)
DK (1)	DK147022C (pt)
ES (5)	ES499394A0 (pt)
FI (1)	FI70904C (pt)
FR (2)	FR2477156A1 (pt)
HK (1)	HK58385A (pt)
IE (1)	IE51394B1 (pt)
IT (1)	IT1170717B (pt)
KE (1)	KE3526A (pt)
MX (1)	MX9202717A (pt)
MY (1)	MY8500757A (pt)
NL (2)	NL191792C (pt)
NZ (1)	NZ196260A (pt)
PT (1)	PT72502B (pt)
SE (1)	SE452468B (pt)
SG (1)	SG36885G (pt)
SK (1)	SK403491A3 (pt)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA817929B (en) *	1980-12-22	1982-10-27	Upjohn Co	5alpha-and 5beta-androstane-17beta-carboxylates

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1436549A (en) *	1972-06-15	1976-05-19	Glaxo Lab Ltd	17beta-mercaptocarbonyl-3alpha-hydroxy-steroids and their esters
GB1438940A (en) *	1972-07-19	1976-06-09	Glaxo Lab Ltd	17beta-haloalkoxycarbonyl-17alpha-oxysteroids
GB1514476A (en) *	1974-08-30	1978-06-14	Glaxo Lab Ltd	Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates
US4188385A (en) *	1978-04-05	1980-02-12	Syntex (U.S.A.) Inc.	Thioetianic acid derivatives
GB1580517A (en) *	1978-04-06	1980-12-03	Fowler I	Crutches

1981
- 1981-02-13 CH CH3890/84A patent/CH651307A5/de not_active IP Right Cessation
- 1981-02-13 DE DE3153379A patent/DE3153379C2/de not_active Expired - Lifetime
- 1981-02-13 FR FR8102818A patent/FR2477156A1/fr active Granted
- 1981-02-13 CH CH98281A patent/CH644615A5/de not_active IP Right Cessation
- 1981-02-13 AT AT0067481A patent/AT395427B/de not_active IP Right Cessation
- 1981-02-13 NZ NZ196260A patent/NZ196260A/xx unknown
- 1981-02-13 NL NL8100707A patent/NL191792C/xx not_active IP Right Cessation
- 1981-02-13 DK DK62381A patent/DK147022C/da not_active IP Right Cessation
- 1981-02-13 IE IE282/81A patent/IE51394B1/en active Protection Beyond IP Right Term
- 1981-02-13 FI FI810444A patent/FI70904C/fi not_active IP Right Cessation
- 1981-02-13 DE DE19813105307 patent/DE3105307A1/de active Granted
- 1981-02-13 ES ES499394A patent/ES499394A0/es active Granted
- 1981-02-13 KR KR1019810000442A patent/KR850000969B1/ko active
- 1981-02-13 PT PT72502A patent/PT72502B/pt unknown
- 1981-02-13 IT IT47792/81A patent/IT1170717B/it active Protection Beyond IP Right Term
- 1981-02-13 AU AU67298/81A patent/AU544517B2/en not_active Expired
- 1981-02-13 SE SE8101010A patent/SE452468B/sv not_active IP Right Cessation
- 1981-08-17 FR FR8115812A patent/FR2485542A1/fr active Granted
1982
- 1982-02-12 ES ES509539A patent/ES8305379A1/es not_active Expired
- 1982-12-14 ES ES518161A patent/ES518161A0/es active Granted
1983
- 1983-08-16 ES ES524985A patent/ES524985A0/es active Granted
1984
- 1984-04-30 ES ES532055A patent/ES532055A0/es active Granted
1985
- 1985-05-13 KE KE3526A patent/KE3526A/xx unknown
- 1985-05-16 SG SG368/85A patent/SG36885G/en unknown
- 1985-08-08 HK HK583/85A patent/HK58385A/xx not_active IP Right Cessation
- 1985-12-30 MY MY757/85A patent/MY8500757A/xx unknown
1991
- 1991-12-23 CZ CS914034A patent/CZ281275B6/cs unknown
- 1991-12-23 SK SK4034-91A patent/SK403491A3/sk unknown
1992
- 1992-06-05 MX MX9202717A patent/MX9202717A/es unknown
1993
- 1993-08-20 BG BG098060A patent/BG60700B2/bg unknown
1996
- 1996-10-29 NL NL960029C patent/NL960029I2/nl unknown

Also Published As

Publication number	Publication date
ES509539A0 (es)	1983-04-01
FI70904B (fi)	1986-07-18
DE3105307C2 (pt)	1988-09-29
ES8600936A1 (es)	1985-10-16
BG60700B2 (bg)	1995-12-29
PT72502A (en)	1981-03-01
IT1170717B (it)	1987-06-03
AU6729881A (en)	1981-08-20
CH644615A5 (de)	1984-08-15
HK58385A (en)	1985-08-16
MY8500757A (en)	1985-12-31
SE452468B (sv)	1987-11-30
KE3526A (en)	1985-06-07
SG36885G (en)	1985-11-15
IE51394B1 (en)	1986-12-24
DE3153379C2 (pt)	1992-11-19
ES8207194A1 (es)	1982-09-01
ES8402317A1 (es)	1984-01-16
CH651307A5 (de)	1985-09-13
DK62381A (da)	1981-08-16
NL960029I2 (nl)	1997-04-01
AU544517B2 (en)	1985-06-06
ATA67481A (de)	1992-05-15
FR2485542A1 (fr)	1981-12-31
FR2477156A1 (fr)	1981-09-04
NL8100707A (nl)	1981-09-16
ES8502447A1 (es)	1985-01-01
NL191792B (nl)	1996-04-01
FR2477156B1 (pt)	1984-11-16
NZ196260A (en)	1983-11-30
ES524985A0 (es)	1985-01-01
FI810444L (fi)	1981-08-16
KR830005262A (ko)	1983-08-03
NL960029I1 (nl)	1997-02-03
ES518161A0 (es)	1984-01-16
NL191792C (nl)	1996-08-02
FI70904C (fi)	1986-10-27
CZ403491A3 (en)	1994-03-16
PT72502B (en)	1982-02-05
CZ281275B6 (cs)	1996-08-14
SK278140B6 (en)	1996-02-07
IE810282L (en)	1981-08-15
FR2485542B1 (pt)	1983-06-10
SE8101010L (sv)	1981-08-16
MX9202717A (es)	1992-06-30
ES532055A0 (es)	1985-10-16
ES8305379A1 (es)	1983-04-01
DE3105307A1 (de)	1981-12-10
IT8147792A0 (it)	1981-02-13
AT395427B (de)	1992-12-28
ES499394A0 (es)	1982-09-01
SK403491A3 (en)	1996-02-07
DK147022C (da)	1984-08-27
DK147022B (da)	1984-03-19

Publication	Publication Date	Title
US4335121A (en)	1982-06-15	Androstane carbothioates
US4377575A (en)	1983-03-22	Corticoid-17-(alkyl carbonates) and process for their manufacture
GB2088877A (en)	1982-06-16	Androstane 17 beta carbothioates
FI78111B (fi)	1989-02-28	Foerfarande foer framstaellning av terapeutiskt aktiva 3,20-dioxo-1,4-pregnadien-17 -ol 17-aromatisk- heterocykliska karboxylater.
US4187301A (en)	1980-02-05	17 Beta-thiocarboxylic acid esters of 6 alpha, 6 beta-difluoro-3-oxoandrost-4-enes
DK147735B (da)	1984-11-26	Analogifremgangsmaade til fremstilling af 3-oxo-androst-4-en-17beta-thiocarboxylsyreestere
KR100290225B1 (ko)	2001-05-15	△ 9,11 스테로이드의 레지오 선택적 제조방법
NO791141L (no)	1979-10-08	17beta-tiokarboksylsyreestere av 4-halogen-3-oksyandrost-4-enes, og fremgangsmaate til deres fremstilling
US4650610A (en)	1987-03-17	Androstane carbothioic acids
JP3346873B2 (ja)	2002-11-18	６α，９α−二弗素化ステロイドの新製造法及び新規な中間体
KR850000969B1 (ko)	1985-07-02	안드로스탄 카보티오에이트의 제조방법
EP0097328B1 (en)	1987-08-26	Process for preparation of steroids
NO153431B (no)	1985-12-09	Fremgangsmaate ved fremstilling av 6alfa-halogen-3-keto-delta1,4-pregnadiener.
JP3037508B2 (ja)	2000-04-24	プレグナ−１，４−ジエン−３，２０−ジオンの新規な置換された１６−メチルステロイド誘導体、それらの製造法、それらの１６−メチレンステロイドの製造への用途及び新規な中間体
DK146017B (da)	1983-05-24	Analogifremgangsmaade til fremstilling af 17alfa-acyloxy-9alfa,21-dihalogen-11beta-hydroxy-6alfa-fluor-16beta-methyl-pregna-1,4-dien-3,20-dion-forbindelser
JP2005530679A (ja)	2005-10-13	６α−フルオロコルチコステロイドの調製方法
GB2137206A (en)	1984-10-03	Androstane 17-carbothioc acid derivatives
JPS632280B2 (pt)	1988-01-18
US4427592A (en)	1984-01-24	Androstene-17-dithioketals
GB2079754A (en)	1982-01-27	Production of 16-methyl-17 -acyloxy corticoids by selective solvolysis of 11-trihaloacetoxy and 21-acyloxy groups
CA1205464A (en)	1986-06-03	Androstane carbothioates
IE51395B1 (en)	1986-12-24	Steroids of the androstane series
KR830000084B1 (ko)	1983-02-08	코르티코이드-17-(알킬 카보네이트)의 제조방법
US3980680A (en)	1976-09-14	Process for the preparation of 21-desoxy-17-acyloxy-4-pregnenes and of 21-iodo-21-desoxy-17-acyl oxy-4-pregnene intermediates useful therein
US3814751A (en)	1974-06-04	Process for preparing 6,6-difluoro-17alpha,21-dihydroxy 16alpha-methyl-4-pregnene-3,20-dione

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