NO743447L - - Google Patents

Info

Publication number: NO743447L
Authority: NO; Norway
Prior art keywords: homo; dione; methyl; pregnadiene; fluoro
Prior art date: 1973-09-26

Application number

NO743447A

Other languages

English (en)

Norwegian (no)

Inventor

U Kerb

K Eslich

R Wiechert

K Petzold

L Alig

A Fuerst

M Mueller

P Keller

Original Assignee

Schering Ag

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.)

1973-09-26

Filing date

1974-09-25

Publication date

1975-04-28

1974-09-25 Application filed by Schering Ag filed Critical Schering Ag

1975-04-28 Publication of NO743447L publication Critical patent/NO743447L/no

Links

238000000034 method Methods 0.000 claims description 66
150000001875 compounds Chemical class 0.000 claims description 41
-1 sub-bromic acid Substances 0.000 claims description 33
238000004519 manufacturing process Methods 0.000 claims description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
150000000795 D-homosteroids Chemical class 0.000 claims description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 18
125000004423 acyloxy group Chemical group 0.000 claims description 17
229910052801 chlorine Inorganic materials 0.000 claims description 17
229910052731 fluorine Inorganic materials 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 10
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 8
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 8
244000005700 microbiome Species 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
238000007127 saponification reaction Methods 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 4
150000001728 carbonyl compounds Chemical class 0.000 claims description 4
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
229910019142 PO4 Inorganic materials 0.000 claims description 3
150000001263 acyl chlorides Chemical class 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
150000004965 peroxy acids Chemical class 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
239000010452 phosphate Substances 0.000 claims description 3
239000004593 Epoxy Substances 0.000 claims description 2
238000010306 acid treatment Methods 0.000 claims description 2
150000001262 acyl bromides Chemical class 0.000 claims description 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 180
239000000243 solution Substances 0.000 description 76
239000000203 mixture Substances 0.000 description 67
238000002844 melting Methods 0.000 description 64
230000008018 melting Effects 0.000 description 64
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
239000000047 product Substances 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
239000011541 reaction mixture Substances 0.000 description 29
239000005457 ice water Substances 0.000 description 22
239000012071 phase Substances 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
238000000855 fermentation Methods 0.000 description 19
230000004151 fermentation Effects 0.000 description 19
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 18
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
229960000583 acetic acid Drugs 0.000 description 16
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
240000008042 Zea mays Species 0.000 description 10
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 10
235000002017 Zea mays subsp mays Nutrition 0.000 description 10
239000003513 alkali Substances 0.000 description 10
235000005822 corn Nutrition 0.000 description 10
239000000284 extract Substances 0.000 description 10
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
235000019441 ethanol Nutrition 0.000 description 9
239000012362 glacial acetic acid Substances 0.000 description 9
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 9
239000002609 medium Substances 0.000 description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
238000003756 stirring Methods 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
238000009835 boiling Methods 0.000 description 8
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
235000011056 potassium acetate Nutrition 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
238000010992 reflux Methods 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
235000011054 acetic acid Nutrition 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
241000223211 Curvularia lunata Species 0.000 description 6
235000010469 Glycine max Nutrition 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
239000007788 liquid Substances 0.000 description 6
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
235000015097 nutrients Nutrition 0.000 description 6
241000193422 Bacillus lentus Species 0.000 description 5
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
229920002472 Starch Polymers 0.000 description 5
238000005273 aeration Methods 0.000 description 5
239000002585 base Substances 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
238000003776 cleavage reaction Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
239000002674 ointment Substances 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
239000000843 powder Substances 0.000 description 5
230000007017 scission Effects 0.000 description 5
229910052710 silicon Inorganic materials 0.000 description 5
239000010703 silicon Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000008107 starch Substances 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000002518 antifoaming agent Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
230000018044 dehydration Effects 0.000 description 4
238000006297 dehydration reaction Methods 0.000 description 4
230000002906 microbiologic effect Effects 0.000 description 4
239000012285 osmium tetroxide Substances 0.000 description 4
229910000489 osmium tetroxide Inorganic materials 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
235000011118 potassium hydroxide Nutrition 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
235000017281 sodium acetate Nutrition 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000003549 soybean oil Substances 0.000 description 4
235000012424 soybean oil Nutrition 0.000 description 4
239000000126 substance Substances 0.000 description 4
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
241000235389 Absidia Species 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000134727 Agromyces mediolanus Species 0.000 description 3
229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
241000235555 Cunninghamella Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
241000589565 Flavobacterium Species 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
239000004133 Sodium thiosulphate Substances 0.000 description 3
PNZVFASWDSMJER-UHFFFAOYSA-N acetic acid;lead Chemical compound [Pb].CC(O)=O PNZVFASWDSMJER-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
229940041514 candida albicans extract Drugs 0.000 description 3
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
150000002924 oxiranes Chemical class 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
229920002545 silicone oil Polymers 0.000 description 3
235000009518 sodium iodide Nutrition 0.000 description 3
159000000000 sodium salts Chemical class 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
150000003431 steroids Chemical class 0.000 description 3
239000012138 yeast extract Substances 0.000 description 3
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 2
JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000223218 Fusarium Species 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
241000192041 Micrococcus Species 0.000 description 2
201000009053 Neurodermatitis Diseases 0.000 description 2
238000006036 Oppenauer oxidation reaction Methods 0.000 description 2
239000001888 Peptone Substances 0.000 description 2
108010080698 Peptones Proteins 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
241000813090 Rhizoctonia solani Species 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
241000082085 Verticillium <Phyllachorales> Species 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
230000003698 anagen phase Effects 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
DKSMCEUSSQTGBK-UHFFFAOYSA-N bromous acid Chemical compound OBr=O DKSMCEUSSQTGBK-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000005266 casting Methods 0.000 description 2
WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 2
229960005091 chloramphenicol Drugs 0.000 description 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
239000008298 dragée Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 2
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LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
NFHRNKANAAGQOH-UHFFFAOYSA-N triphenylstannane Chemical compound C1=CC=CC=C1[SnH](C=1C=CC=CC=1)C1=CC=CC=C1 NFHRNKANAAGQOH-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/85—Flavobacterium

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)

NO743447A 1973-09-26 1974-09-25 NO743447L (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19732349022 DE2349022A1 (de)	1973-09-26	1973-09-26	Neue d-homo-steroide

Publications (1)

Publication Number	Publication Date
NO743447L true NO743447L (de)	1975-04-28

Family

ID=5894078

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO743447A NO743447L (de)	1973-09-26	1974-09-25

Country Status (22)

Country	Link
US (1)	US4026921A (de)
JP (1)	JPS5076063A (de)
AT (1)	AT351180B (de)
AU (1)	AU7373674A (de)
BE (1)	BE820385A (de)
CA (1)	CA1033713A (de)
CS (3)	CS183798B2 (de)
DD (1)	DD114600A5 (de)
DE (1)	DE2349022A1 (de)
DK (1)	DK136534C (de)
ES (1)	ES430428A1 (de)
FI (1)	FI280374A (de)
FR (1)	FR2244471B1 (de)
GB (1)	GB1488031A (de)
HU (1)	HU182049B (de)
IE (1)	IE39917B1 (de)
IL (1)	IL45738A (de)
LU (1)	LU70986A1 (de)
NL (1)	NL7412745A (de)
NO (1)	NO743447L (de)
SE (1)	SE406327B (de)
ZA (1)	ZA746133B (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7611162A (nl) *	1975-10-22	1977-04-26	Hoffmann La Roche	Nieuwe d-homosteroiden.
AT356301B (de) *	1976-09-03	1980-04-25	Hoffmann La Roche	Verfahren zur herstellung von neuen d-homo- steroiden
DK0973791T3 (da)	1995-12-11	2007-09-17	Searle Llc	Fremgangsmåde til fremstilling af en epoxyforbindelse
KR100523409B1 (ko)	1996-12-11	2005-10-24	지.디. 썰 엘엘씨	9,11-에폭시 스테로이드의 제조방법 및 이 제조방법에유용한 중간체
US6887991B1 (en)	1996-12-11	2005-05-03	G. D. Searle & Company	Processes for preparation of 9, 11-epoxy steroids and intermediates useful therein
US7235655B2 (en)	2002-03-22	2007-06-26	Pharmacia & Upjohn Company	Processes to prepare eplerenone
EP1679317A3 (de) *	2002-08-16	2006-09-13	Pharmacia & Upjohn Company LLC	5-Androsten-3-Ol Steroid Zwischenprodukte und Verfahren zu ihrer Herstellung
BR0313523A (pt) *	2002-08-16	2005-06-28	Upjohn Co	Intermediários do esteróide 5-androsten-3(beta)-ol e processos para a sua preparação
US20060100185A1 (en) *	2004-06-01	2006-05-11	White Michael J	5-Androsten-3beta-ol steroid intermediates and processes for their preparation
DE602006013448D1 (de) *	2005-05-18	2010-05-20	Merck Sharp & Dohme	D-homoandrosta-17-yl-carbamat-derivate als selektive glucocorticoid-rezeptor-liganden
JP5826750B2 (ja) *	2009-09-11	2015-12-02	バイオネイチャーイー．エイ．リミテッド．	炎症性疾患および自己免疫疾患へのステロイド化合物の使用
WO2016084790A1 (ja) *	2014-11-25	2016-06-02	第一三共株式会社	ヒドロナフトキノリン誘導体

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2860158A (en) *	1954-10-18	1958-11-11	Sterling Drug Inc	Compounds of the perhydrochrysene series and preparation thereof
US2822381A (en) *	1954-11-24	1958-02-04	Searle & Co	3-oxygenated 16-hydroxy-d-homopregnen-20-ones and their esters
US3076023A (en) *	1960-05-31	1963-01-29	Schering Ag	Process for preparing d-homo steroids
DE1493183C3 (de) *	1965-12-11	1975-04-10	Schering Ag, 1000 Berlin Und 4619 Bergkamen	D-Homosteroide, Verfahren zu ihrer Herstellung und diese enthaltende Mittel
DK142289B (da) *	1973-03-28	1980-10-06	Hoffmann La Roche	Analogifremgangsmåde til fremstilling af D-homopregn-4-en-3,20-dioner.

1973
- 1973-09-26 DE DE19732349022 patent/DE2349022A1/de active Pending
1974
- 1974-09-20 US US05/507,883 patent/US4026921A/en not_active Expired - Lifetime
- 1974-09-23 GB GB41323/74A patent/GB1488031A/en not_active Expired
- 1974-09-24 LU LU70986A patent/LU70986A1/xx unknown
- 1974-09-24 AT AT768274A patent/AT351180B/de not_active IP Right Cessation
- 1974-09-25 CS CS7600003417A patent/CS183798B2/cs unknown
- 1974-09-25 CS CS7600003418A patent/CS183799B2/cs unknown
- 1974-09-25 HU HU74SCHE497A patent/HU182049B/hu unknown
- 1974-09-25 CS CS7400006591A patent/CS183763B2/cs unknown
- 1974-09-25 IL IL45738A patent/IL45738A/en unknown
- 1974-09-25 SE SE7412060A patent/SE406327B/xx unknown
- 1974-09-25 NO NO743447A patent/NO743447L/no unknown
- 1974-09-26 DK DK508174A patent/DK136534C/da active
- 1974-09-26 BE BE148937A patent/BE820385A/xx unknown
- 1974-09-26 FI FI2803/74A patent/FI280374A/fi unknown
- 1974-09-26 IE IE2001/74A patent/IE39917B1/xx unknown
- 1974-09-26 ES ES430428A patent/ES430428A1/es not_active Expired
- 1974-09-26 AU AU73736/74A patent/AU7373674A/en not_active Expired
- 1974-09-26 CA CA210,140A patent/CA1033713A/en not_active Expired
- 1974-09-26 FR FR7432427A patent/FR2244471B1/fr not_active Expired
- 1974-09-26 NL NL7412745A patent/NL7412745A/xx not_active Application Discontinuation
- 1974-09-26 ZA ZA00746133A patent/ZA746133B/xx unknown
- 1974-09-26 DD DD181345A patent/DD114600A5/xx unknown
- 1974-09-26 JP JP49110931A patent/JPS5076063A/ja active Pending

Also Published As

Publication number	Publication date
SE7412060L (de)	1975-03-27
CS183799B2 (en)	1978-07-31
AU7373674A (en)	1976-04-01
ES430428A1 (es)	1976-10-01
IE39917B1 (en)	1979-01-31
NL7412745A (nl)	1975-04-01
CA1033713A (en)	1978-06-27
DK136534C (da)	1978-03-28
LU70986A1 (de)	1975-03-06
IL45738A (en)	1978-10-31
DE2349022A1 (de)	1975-04-10
HU182049B (en)	1983-12-28
ATA768274A (de)	1978-12-15
FR2244471B1 (de)	1978-02-03
DD114600A5 (de)	1975-08-12
ZA746133B (en)	1975-11-26
IE39917L (en)	1975-03-26
AT351180B (de)	1979-07-10
GB1488031A (en)	1977-10-05
CS183798B2 (en)	1978-07-31
SE406327B (sv)	1979-02-05
DK508174A (de)	1975-06-09
CS183763B2 (en)	1978-07-31
IL45738A0 (en)	1974-11-29
FI280374A (de)	1975-03-27
JPS5076063A (de)	1975-06-21
DK136534B (da)	1977-10-24
FR2244471A1 (de)	1975-04-18
BE820385A (fr)	1975-03-26
US4026921A (en)	1977-05-31

Publication	Publication Date	Title
US3939193A (en)	1976-02-17	D-Homosteroids
NO743447L (de)	1975-04-28
IE831658L (en)	1984-01-19	6,16-dimethyl corticoids
NO139524B (no)	1978-12-18	Analogifremgangsmaate ved fremstilling av nye d-homosteroider
NO743448L (de)	1975-04-28
EP0039311B1 (de)	1984-07-11	Halogenierte Steroide
US4207316A (en)	1980-06-10	Novel 17-substituted 11 β-hydroxy steroids of the pregnane series, their manufacture, preparation and use
US4196203A (en)	1980-04-01	Novel corticoids
US4012510A (en)	1977-03-15	Novel methylene steroids
JPH0257559B2 (de)	1990-12-05
US4029692A (en)	1977-06-14	Steroid carboxylic acids and derivatives
US4202841A (en)	1980-05-13	D-Homopregnanes
CA1144538A (en)	1983-04-12	Steroids of the pregnane series substituted in the 17-position, and their manufacture and use
US4272630A (en)	1981-06-09	D-Homosteroids
NO132236B (de)	1975-06-30
US4026923A (en)	1977-05-31	D-Homosteroids
US3828083A (en)	1974-08-06	Novel 6alpha,16alpha-dimethyl steroids
US3261851A (en)	1966-07-19	16alpha-fluoromethyl compounds of the pregnane series and processes for the production thereof
US3519619A (en)	1970-07-07	16-alkylidene pregnanes and process for their manufacture
CA1172590A (en)	1984-08-14	Steroids of the pregnane series substituted in the 17- position, and their manufacture and use
US4137269A (en)	1979-01-30	D-homosteroids
US2999103A (en)	1961-09-05	16-nitro-alkyl steroids
NO135528B (de)	1977-01-10
NO145621B (no)	1982-01-18	Analogifremgangsmaate ved fremstilling av terapeutisk virksomme d-homosteroider
DE2753839A1 (de)	1979-05-31	Neue kortikoide