NO122590B - - Google Patents

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Info

Publication number: NO122590B
Authority: NO; Norway
Prior art keywords: methyl; dione; diol; acetate; hydrogen
Prior art date: 1961-02-22

Application number

NO143323A

Other languages

English (en)

Norwegian (no)

Inventor

K Kieslich

U Kerb

G Raspe

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.)

1961-02-22

Filing date

1962-02-21

Publication date

1971-07-19

1962-02-21 Application filed by Schering Ag filed Critical Schering Ag

1971-07-19 Publication of NO122590B publication Critical patent/NO122590B/no

Links

150000001875 compounds Chemical class 0.000 claims description 21
230000000694 effects Effects 0.000 claims description 20
230000003110 anti-inflammatory effect Effects 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 15
238000000034 method Methods 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
241000223211 Curvularia lunata Species 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
241000193422 Bacillus lentus Species 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
241000203720 Pimelobacter simplex Species 0.000 claims description 5
102000004190 Enzymes Human genes 0.000 claims description 4
108090000790 Enzymes Proteins 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 3
150000003431 steroids Chemical class 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
230000002411 adverse Effects 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
239000012024 dehydrating agents‎ Substances 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
230000001925 catabolic effect Effects 0.000 description 13
239000000284 extract Substances 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
241001465754 Metazoa Species 0.000 description 11
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 11
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 11
240000008042 Zea mays Species 0.000 description 11
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238000000855 fermentation Methods 0.000 description 11
230000004151 fermentation Effects 0.000 description 11
229940043265 methyl isobutyl ketone Drugs 0.000 description 11
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 10
239000012043 crude product Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000008103 glucose Substances 0.000 description 10
235000015097 nutrients Nutrition 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
230000002394 glycogenic effect Effects 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
238000005273 aeration Methods 0.000 description 7
150000002168 ethanoic acid esters Chemical class 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
235000005822 corn Nutrition 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
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235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
230000000875 corresponding effect Effects 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
235000009973 maize Nutrition 0.000 description 5
VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 5
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239000010935 stainless steel Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 4
239000001963 growth medium Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
229960001067 hydrocortisone acetate Drugs 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
239000002504 physiological saline solution Substances 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
238000005406 washing Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
230000001580 bacterial effect Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000000155 melt Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000011550 stock solution Substances 0.000 description 3
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
229920002527 Glycogen Polymers 0.000 description 2
206010018691 Granuloma Diseases 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
CZMRCDWAGMRECN-UHFFFAOYSA-N Rohrzucker Natural products OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
238000010171 animal model Methods 0.000 description 2
229940041514 candida albicans extract Drugs 0.000 description 2
238000011097 chromatography purification Methods 0.000 description 2
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
229960003654 desoxycortone Drugs 0.000 description 2
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
210000000416 exudates and transudate Anatomy 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
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 2
239000003862 glucocorticoid Substances 0.000 description 2
229940096919 glycogen Drugs 0.000 description 2
229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
235000012054 meals Nutrition 0.000 description 2
239000002609 medium Substances 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
235000013379 molasses Nutrition 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000012453 sprague-dawley rat model Methods 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
229960004793 sucrose Drugs 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
238000005303 weighing Methods 0.000 description 2
239000012138 yeast extract Substances 0.000 description 2
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
QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
-1 6a,9a-difluoro-1,4-pregnadiene Chemical compound 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
FIHZWZBEAXASKA-UHFFFAOYSA-N Anthron Natural products COc1cc2Cc3cc(C)cc(O)c3C(=O)c2c(O)c1C=CC(C)C FIHZWZBEAXASKA-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000499489 Castor canadensis Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 1
ITRJWOMZKQRYTA-RFZYENFJSA-N Cortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O ITRJWOMZKQRYTA-RFZYENFJSA-N 0.000 description 1
VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 1
102000002322 Egg Proteins Human genes 0.000 description 1
108010000912 Egg Proteins Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
235000011779 Menyanthes trifoliata Nutrition 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
GGISZLOBBISXOZ-UHFFFAOYSA-N acetic acid;chloroform Chemical compound CC(O)=O.ClC(Cl)Cl GGISZLOBBISXOZ-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000008272 agar Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
MZJUGRUTVANEDW-UHFFFAOYSA-N bromine fluoride Chemical compound BrF MZJUGRUTVANEDW-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229940099112 cornstarch Drugs 0.000 description 1
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
229960003290 cortisone acetate Drugs 0.000 description 1
229940117173 croton oil Drugs 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
238000001035 drying Methods 0.000 description 1
235000014103 egg white Nutrition 0.000 description 1
210000000969 egg white Anatomy 0.000 description 1
238000010828 elution Methods 0.000 description 1
SYWHXTATXSMDSB-GSLJADNHSA-N fludrocortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O SYWHXTATXSMDSB-GSLJADNHSA-N 0.000 description 1
229960003336 fluorocortisol acetate Drugs 0.000 description 1
230000003087 glucogenic effect Effects 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 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
230000033444 hydroxylation Effects 0.000 description 1
238000005805 hydroxylation reaction Methods 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000004816 paper chromatography Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003145 progesterone derivatives Chemical class 0.000 description 1
230000007425 progressive decline Effects 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
- 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
- Y10S435/832—Bacillus
- 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
- Y10S435/843—Corynebacterium
- 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
- Y10S435/911—Microorganisms using fungi

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)

NO143323A 1961-02-22 1962-02-21 NO122590B (da)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DESCH29274A DE1169444B (de)	1961-02-22	1961-02-22	Verfahren zur Herstellung von ?-16ª-Methylsteroiden

Publications (1)

Publication Number	Publication Date
NO122590B true NO122590B (da)	1971-07-19

Family

ID=7431375

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO143323A NO122590B (da)	1961-02-22	1962-02-21

Country Status (11)

Country	Link
US (1)	US3232839A (da)
BE (1)	BE614196A (da)
BR (1)	BR6236628D0 (da)
CH (1)	CH416608A (da)
DE (1)	DE1169444B (da)
DK (1)	DK105157C (da)
FI (1)	FI42958B (da)
FR (1)	FR1916M (da)
GB (1)	GB990384A (da)
NO (1)	NO122590B (da)
SE (1)	SE303283B (da)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3426128A (en) *	1961-02-22	1969-02-04	Schering Ag	Delta**1,4-16alpha-methyl steroids
GB1105013A (en) *	1964-12-01	1968-03-06	Organon Labor Ltd	17ª-alkyl steroids and a process for making them
CH513843A (fr) *	1969-04-23	1971-10-15	Lark Spa	Procédé d'oxhydrilation microbiologique en position 11B
JPS5549078B2 (da) *	1972-12-27	1980-12-10
DE2712861C2 (de) *	1977-03-21	1986-02-27	Schering AG, 1000 Berlin und 4709 Bergkamen	17-Acetoxy-6-chlor-15β-hydroxy-1α,2α-methylen-4,6-pregnadien-3,20-dion, Verfahren zu seiner Herstellung und dieses enthaltende Arzneimittel
DE2715853A1 (de) *	1977-04-06	1978-10-19	Schering Ag	Wasserloesliche kortikoide
DE2920726A1 (de) *	1979-05-18	1980-11-27	Schering Ag	Neue kortikoide, ihre herstellung und verwendung
FR2747680B1 (fr) *	1996-04-18	1998-07-03	Roussel Uclaf	Nouveaux steroides, leur application a titre de medicaments, leur procede de preparation, les intermediaires de ce procede et les compositions pharmaceutiques les renfermant
US20130211069A1 (en)	2010-07-20	2013-08-15	Taro Pharmaceutical Industries Ltd.	Process for the preparation of 17-desoxy-corticosteroids
CN107793460A (zh) *	2016-08-30	2018-03-13	天津太平洋制药有限公司	一种氟可龙的制备方法
CA3042428A1 (en)	2016-11-08	2018-05-17	Regeneron Pharmaceuticals, Inc.	Steroids and protein-conjugates thereof
KR20250008984A (ko)	2017-05-18	2025-01-16	리제너론 파마슈티칼스 인코포레이티드	사이클로덱스트린 단백질 약물 접합체
CA3247730A1 (en)	2017-11-07	2025-10-30	Regeneron Pharmaceuticals, Inc.	Hydrophilic linkers for antibody drug conjugates
MA50259A1 (fr)	2018-01-08	2021-07-29	Regeneron Pharma	Stéroïdes et leurs conjugués-anticorps
WO2019217591A1 (en)	2018-05-09	2019-11-14	Regeneron Pharmaceuticals, Inc.	Anti-msr1 antibodies and methods of use thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2876219A (en) *	1958-06-09	1959-03-03	Upjohn Co	6-fluoro-9alpha-halo-11-oxygenated-4-pregnenes and 6-fluoro-9alpha-halo-11-oxygenated-1,4-pregnadienes

1961
- 1961-02-22 DE DESCH29274A patent/DE1169444B/de active Pending
1962
- 1962-01-22 GB GB2268/62D patent/GB990384A/en not_active Expired
- 1962-02-06 FI FI0244/62A patent/FI42958B/fi active
- 1962-02-14 CH CH181562A patent/CH416608A/de unknown
- 1962-02-20 SE SE1831/62A patent/SE303283B/xx unknown
- 1962-02-21 NO NO143323A patent/NO122590B/no unknown
- 1962-02-21 BE BE614196A patent/BE614196A/fr unknown
- 1962-02-22 DK DK83062AA patent/DK105157C/da active
- 1962-02-22 BR BR136628/62A patent/BR6236628D0/pt unknown
- 1962-05-21 FR FR898210A patent/FR1916M/fr active Active
1963
- 1963-11-12 US US323062A patent/US3232839A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
BE614196A (fr)	1962-08-21
DK105157C (da)	1966-08-29
BR6236628D0 (pt)	1973-05-31
FR1916M (fr)	1963-07-15
CH416608A (de)	1966-07-15
FI42958B (da)	1970-09-02
DE1169444B (de)	1964-05-06
US3232839A (en)	1966-02-01
GB990384A (en)	1965-04-28
SE303283B (da)	1968-08-26

Publication	Publication Date	Title
US3232839A (en)	1966-02-01	delta1, 4-16alpha-methyl steroids
DE1154102B (de)	1963-09-12	Verfahren zur Herstellung therapeutisch wirksamer Steroidverbindungen
IL45738A (en)	1978-10-31	D-homo-pregnenes,process for their preparation and pharmaceutical compositions containing them
US2874172A (en)	1959-02-17	11-oxygenated 1, 4, 16-pregnatriene-21-ol-3, 20 diones and esters thereof
US2985563A (en)	1961-05-23	11alpha-hydroxylation of steroids by glomerella
DE1059906B (de)	1959-06-25	Verfahren zur Herstellung von 1, 4-Pregnadienen
NO139524B (no)	1978-12-18	Analogifremgangsmaate ved fremstilling av nye d-homosteroider
US3004994A (en)	1961-10-17	6alpha, 16alpha-dimethyl-pregnenes
US3013945A (en)	1961-12-19	11alpha-hydroxylation of steroids by beauveria
US2867632A (en)	1959-01-06	6-methyl steroid compounds
US3426128A (en)	1969-02-04	Delta**1,4-16alpha-methyl steroids
US2867638A (en)	1959-01-06	6-methyl-9alpha fluoro-11 oxygenated pregnenes
US3054725A (en)	1962-09-18	11-hydroxylation of steroids by phoma microorganisms
DD150749A5 (de)	1981-09-16	Verfahren zur herstellung von 11 beta-hydroxysteroiden der pregnanreihe
US2958631A (en)	1960-11-01	Hydroxylated steroids and methods for their manufacture using bacillus megatherium
US2867634A (en)	1959-01-06	11-oxygenated 6-methyl-pregnadienes
US2876219A (en)	1959-03-03	6-fluoro-9alpha-halo-11-oxygenated-4-pregnenes and 6-fluoro-9alpha-halo-11-oxygenated-1,4-pregnadienes
US3375261A (en)	1968-03-26	Ring a unsaturated-20-oxo-11, 17-bis-oxygenated 16-methyl-steroids of the pregnane seies
US3054811A (en)	1962-09-18	Ring a unsaturated 6, 16-dimethyl steroids of the pregnane series
GB792803A (en)	1958-04-02	Oxidation products from compounds of the steroid series and process of making same
US3431173A (en)	1969-03-04	Process for the preparation of 17alpha-acyloxy-21-hydroxy-pregnanes
DK142057B (da)	1980-08-18	Analogifremgangsmaade til fremstilling af 15alfa,16alfa-methylen-1,4-pregnadien-3,20-dionderivater
US3031476A (en)	1962-04-24	6-methyl-11, 17alpha-dioxygenated-4, 6-pregnadienes
US3009929A (en)	1961-11-21	9, 11-halogenated progestins
DE1113690B (de)	1961-09-14	Verfahren zur Herstellung von in 11-Stellung durch sauerstoffhaltige Gruppen substituierten 16-Methyl-1, 4-pregnadien-17ª‡-ol-3, 20-dion-Verbindungen