SE204632C1

SE204632C1 -

Info

Publication number: SE204632C1
Authority: SE; Sweden
Prior art keywords: pregnadiene; dione; ester; acid; group
Prior art date: 1965-01-01

Application number

Other languages

English (en)

Swedish (sv)

Publication date

1965-01-01

1965-01-01 Publication of SE204632C1 publication Critical patent/SE204632C1/sv

Links

150000002148 esters Chemical class 0.000 claims description 37
244000005700 microbiome Species 0.000 claims description 37
238000000034 method Methods 0.000 claims description 33
150000001875 compounds Chemical class 0.000 claims description 28
239000007858 starting material Substances 0.000 claims description 19
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
239000000126 substance Substances 0.000 claims description 15
-1 pregnene compound Chemical class 0.000 claims description 14
241000203720 Pimelobacter simplex Species 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 11
229960000890 hydrocortisone Drugs 0.000 claims description 9
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims description 8
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 8
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 8
229960004544 cortisone Drugs 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
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241000186216 Corynebacterium Species 0.000 claims description 6
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241000235546 Rhizopus stolonifer Species 0.000 claims description 5
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241000010216 Cunninghamella blakesleeana Species 0.000 claims description 4
241000235527 Rhizopus Species 0.000 claims description 4
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235000013752 Rhizopus oryzae Nutrition 0.000 claims description 4
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OEARCSLBIZEZSH-XNKUGNQISA-N [C].[C@@H]12CC[C@H](CC)[C@@]1(C)CC[C@H]1[C@H]2CCC2CCCC[C@]12C Chemical group [C].[C@@H]12CC[C@H](CC)[C@@]1(C)CC[C@H]1[C@H]2CCC2CCCC[C@]12C OEARCSLBIZEZSH-XNKUGNQISA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
241000894007 species Species 0.000 claims description 3
WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 2
241000235400 Phycomyces Species 0.000 claims description 2
AAXVEMMRQDVLJB-BULBTXNYSA-N fludrocortisone Chemical compound O=C1CC[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 AAXVEMMRQDVLJB-BULBTXNYSA-N 0.000 claims description 2
238000013048 microbiological method Methods 0.000 claims description 2
DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
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238000006243 chemical reaction Methods 0.000 description 28
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OIGNJSKKLXVSLS-UHFFFAOYSA-N 11,17,21-Trihydroxypregna-1,4-diene-3,20-dione Chemical compound O=C1C=CC2(C)C3C(O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 OIGNJSKKLXVSLS-UHFFFAOYSA-N 0.000 description 20
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WHBHBVVOGNECLV-OBQKJFGGSA-N 11-deoxycortisol Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 WHBHBVVOGNECLV-OBQKJFGGSA-N 0.000 description 5
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