BE572383A - - Google Patents
Info
- Publication number
- BE572383A BE572383A BE572383DA BE572383A BE 572383 A BE572383 A BE 572383A BE 572383D A BE572383D A BE 572383DA BE 572383 A BE572383 A BE 572383A
- Authority
- BE
- Belgium
- Prior art keywords
- pregnadiene
- hydroxy
- fluoro
- dione
- trione
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 21
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- YMBXMIIPJXGJNY-PKTBXOATSA-N (8s,9s,10r,13s,14s)-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,12,14,15-octahydro-1h-cyclopenta[a]phenanthrene-3,11-dione Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)(C(=CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 YMBXMIIPJXGJNY-PKTBXOATSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 1
- 206010030113 Oedema Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229930195733 hydrocarbon Natural products 0.000 description 12
- 150000002430 hydrocarbons Chemical class 0.000 description 12
- -1 steroid compounds Chemical class 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 235000015497 potassium bicarbonate Nutrition 0.000 description 7
- 239000011736 potassium bicarbonate Substances 0.000 description 7
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 7
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QWLYGCNTTTWATC-DOWMQLCMSA-N (8S,9S,10R,13S,14S)-17-(2-hydroxyacetyl)-10,13,16-trimethyl-2,6,7,8,9,12,14,15-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione Chemical compound OCC(C1=C(C[C@H]2[C@@H]3CCC4=CC(CC[C@]4(C)[C@H]3C(C[C@]12C)=O)=O)C)=O QWLYGCNTTTWATC-DOWMQLCMSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- WLDZAHVVWWSFSL-GAMLAWPCSA-N (8S,9R,10S,13S,14S)-9-fluoro-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,12,14,15-octahydrocyclopenta[a]phenanthrene-3,11-dione Chemical compound F[C@@]12[C@]3(CCC(C=C3CC[C@H]1[C@@H]1CC=C(C(CO)=O)[C@]1(CC2=O)C)=O)C WLDZAHVVWWSFSL-GAMLAWPCSA-N 0.000 description 2
- VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- YEUXZCWXSVHCLH-NWQAGDSVSA-N F[C@@]12[C@]3(CCC(C=C3CC[C@H]1[C@@H]1CC(=C(C(CO)=O)[C@]1(CC2O)C)C)=O)C Chemical compound F[C@@]12[C@]3(CCC(C=C3CC[C@H]1[C@@H]1CC(=C(C(CO)=O)[C@]1(CC2O)C)C)=O)C YEUXZCWXSVHCLH-NWQAGDSVSA-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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229940107700 pyruvic acid Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VWCMJGGDWXPDFW-OPXVNJCFSA-N (8S,9R,10S,13S,14S)-9-fluoro-17-(2-hydroxyacetyl)-10,13,16-trimethyl-1,2,6,7,8,12,14,15-octahydrocyclopenta[a]phenanthrene-3,11-dione Chemical compound F[C@@]12[C@]3(CCC(C=C3CC[C@H]1[C@@H]1CC(=C(C(CO)=O)[C@]1(CC2=O)C)C)=O)C VWCMJGGDWXPDFW-OPXVNJCFSA-N 0.000 description 1
- OIJCKMBEIQWKPX-SPAGYVKCSA-N (8r,9s,10r,13s,14s)-10,13-dimethyl-17-propanoyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)CC)[C@@]1(C)CC2 OIJCKMBEIQWKPX-SPAGYVKCSA-N 0.000 description 1
- AATFZIOHQGNMOO-LJCDUQBNSA-N (8r,9s,10r,13s,14s)-17-acetyl-10,13,16-trimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(C)=C(C(=O)C)[C@@]1(C)CC2 AATFZIOHQGNMOO-LJCDUQBNSA-N 0.000 description 1
- GUHFLRTWNHWJBS-VLTGGNAYSA-N (8r,9s,10s,13s)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1C1=CC=C(C(=O)C)[C@@]1(C)CC2 GUHFLRTWNHWJBS-VLTGGNAYSA-N 0.000 description 1
- BZQGPHCPHVYIJP-MHLVISCWSA-N (8s,9s,10r,13s,14s)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3C(O)C[C@](C)(C(=CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 BZQGPHCPHVYIJP-MHLVISCWSA-N 0.000 description 1
- ISSDLYGYISYKTD-UQVNRYHBSA-N 2-[(8R,9S,10R,13S,14S)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanol Chemical compound C(CC1=CC[C@H]2[C@@H]3CCC4=CCCC[C@]4(C)[C@H]3CC[C@]12C)O ISSDLYGYISYKTD-UQVNRYHBSA-N 0.000 description 1
- CVRYIPLPFAKSEY-SJFWLOONSA-N 2-[(8s,9s,10r,13r,14s,17r)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanol Chemical compound C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)CCO)[C@@H]4[C@@H]3CCC2=C1 CVRYIPLPFAKSEY-SJFWLOONSA-N 0.000 description 1
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000575946 Ione Species 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ASGJEMPQQVNTGO-UHFFFAOYSA-N benzene chloroform Chemical compound C(Cl)(Cl)Cl.C1=CC=CC=C1.C1=CC=CC=C1 ASGJEMPQQVNTGO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 210000003979 eosinophil Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide group Chemical group NNC(=O)N DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE572383A true BE572383A (enrdf_load_stackoverflow) |
Family
ID=190208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE572383D BE572383A (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE572383A (enrdf_load_stackoverflow) |
-
0
- BE BE572383D patent/BE572383A/fr unknown
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