JPS58109500A - プレグナン系ステロイド１７α―エステル，２１―クロリド化合物の製造法 - Google Patents
プレグナン系ステロイド１７α―エステル，２１―クロリド化合物の製造法Info
- Publication number
- JPS58109500A JPS58109500A JP20620881A JP20620881A JPS58109500A JP S58109500 A JPS58109500 A JP S58109500A JP 20620881 A JP20620881 A JP 20620881A JP 20620881 A JP20620881 A JP 20620881A JP S58109500 A JPS58109500 A JP S58109500A
- Authority
- JP
- Japan
- Prior art keywords
- chloride
- reaction
- compound
- steroid
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- -1 pregnane steroid Chemical class 0.000 title abstract description 23
- 238000002360 preparation method Methods 0.000 title description 2
- 150000003431 steroids Chemical class 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 30
- 239000002904 solvent Substances 0.000 abstract description 16
- 229940079593 drug Drugs 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 4
- 206010061218 Inflammation Diseases 0.000 abstract description 3
- 230000004054 inflammatory process Effects 0.000 abstract description 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 2
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- 150000003511 tertiary amides Chemical class 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- JYRSCMLJPXJTLI-UHFFFAOYSA-N 9h-xanthene-9-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)C3=CC=CC=C3OC2=C1 JYRSCMLJPXJTLI-UHFFFAOYSA-N 0.000 abstract 2
- 230000009285 allergic inflammation Effects 0.000 abstract 1
- 229940088597 hormone Drugs 0.000 abstract 1
- 239000005556 hormone Substances 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 208000017520 skin disease Diseases 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 70
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 65
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000003756 stirring Methods 0.000 description 36
- VHRSUDSXCMQTMA-PJHHCJLFSA-N 6alpha-methylprednisolone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 VHRSUDSXCMQTMA-PJHHCJLFSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 28
- 238000000034 method Methods 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 150000003839 salts Chemical class 0.000 description 21
- 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 description 20
- 239000013078 crystal Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 210000003323 beak Anatomy 0.000 description 10
- 229960000890 hydrocortisone Drugs 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- OCFYTOIAJLLHDS-UHFFFAOYSA-N 1-ethoxybutane-1,1-diol Chemical compound CCCC(O)(O)OCC OCFYTOIAJLLHDS-UHFFFAOYSA-N 0.000 description 8
- 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
- 239000012043 crude product Substances 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 241001474791 Proboscis Species 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 229960005205 prednisolone Drugs 0.000 description 7
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone 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]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 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 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229960004584 methylprednisolone Drugs 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 6
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 5
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- ABUISBDTYAZRHY-RBKZJGKHSA-N (6s,8s,9r,10s,11s,13s,14s,17r)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3C[C@H](F)C2=C1 ABUISBDTYAZRHY-RBKZJGKHSA-N 0.000 description 3
- MXIPOPWDCHIWBZ-UHFFFAOYSA-N 2,6-dioxo-3h-purine-9-carbonyl chloride Chemical compound N1C(=O)NC(=O)C2=C1N(C(=O)Cl)C=N2 MXIPOPWDCHIWBZ-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 description 3
- 229940092705 beclomethasone Drugs 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229960003957 dexamethasone Drugs 0.000 description 3
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical compound CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- MVMNMTZQJONYAA-UHFFFAOYSA-N CC(C)c1cc(=O)c(O)cc2c3cc(O)c(=O)cc(C(C)C)c3oc12 Chemical compound CC(C)c1cc(=O)c(O)cc2c3cc(O)c(=O)cc(C(C)C)c3oc12 MVMNMTZQJONYAA-UHFFFAOYSA-N 0.000 description 2
- 239000005973 Carvone Substances 0.000 description 2
- 241000252203 Clupea harengus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001919 adrenal effect Effects 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 229960002537 betamethasone Drugs 0.000 description 2
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000019514 herring Nutrition 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000002905 orthoesters Chemical group 0.000 description 2
- 229960004618 prednisone Drugs 0.000 description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 229940070710 valerate Drugs 0.000 description 2
- WNYLPFCKNQAAMB-PPUNREKOSA-N (8s,9s,10r,11s,13s,14s,16r,17r)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O WNYLPFCKNQAAMB-PPUNREKOSA-N 0.000 description 1
- WCPYLHZAHDOKCA-HGUQNLGYSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-10,13-dimethyl-1,2,3,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one Chemical compound C1C(=O)C2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 WCPYLHZAHDOKCA-HGUQNLGYSA-N 0.000 description 1
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- JAFMOTJMRSZOJE-UHFFFAOYSA-N 1,1,1-trimethoxybutane Chemical compound CCCC(OC)(OC)OC JAFMOTJMRSZOJE-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- UBBBZCCMNCZZLZ-UHFFFAOYSA-N 1-ethoxypropane-1,1-diol Chemical compound CCOC(O)(O)CC UBBBZCCMNCZZLZ-UHFFFAOYSA-N 0.000 description 1
- LBKIRBXELMWQRC-UHFFFAOYSA-N 1-methoxypropane-1,1-diol Chemical compound CCC(O)(O)OC LBKIRBXELMWQRC-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- ASFAFOSQXBRFMV-LJQANCHMSA-N 3-n-(2-benzyl-1,3-dihydroxypropan-2-yl)-1-n-[(1r)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzene-1,3-dicarboxamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=1)=CC(N(C)S(C)(=O)=O)=CC=1C(=O)NC(CO)(CO)CC1=CC=CC=C1 ASFAFOSQXBRFMV-LJQANCHMSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 241001566735 Archon Species 0.000 description 1
- NDKKSISAYUMBII-UHFFFAOYSA-N CC(=O)C.ClCCCCCC Chemical compound CC(=O)C.ClCCCCCC NDKKSISAYUMBII-UHFFFAOYSA-N 0.000 description 1
- 108700018454 CDC15 Proteins 0.000 description 1
- 101100313164 Caenorhabditis elegans sea-1 gene Proteins 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 235000008753 Papaver somniferum Nutrition 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- VSBFNCXKYIEYIS-UHFFFAOYSA-N Xanthene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)C3=CC=CC=C3OC2=C1 VSBFNCXKYIEYIS-UHFFFAOYSA-N 0.000 description 1
- ITYMTTQVNYAJAA-XGQKBEPLSA-N [(8s,9r,10s,11s,13s,14s,16s,17r)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(OC(=O)CC)[C@@]1(C)C[C@@H]2O ITYMTTQVNYAJAA-XGQKBEPLSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 101150081467 cdc15 gene Proteins 0.000 description 1
- FGGUAEKPLDMWSF-HMHFYOQSSA-N chembl2376821 Chemical compound O([C@@H]1[C@@H]2[C@@H]3O[C@]3(CO)[C@@H](O)[C@@]3(O)[C@H]([C@]2([C@H](C)C[C@@]1(O1)C(C)=C)O2)C[C@@H]([C@@H]3O)C)C21C1=CC=CC=C1 FGGUAEKPLDMWSF-HMHFYOQSSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- BMCQMVFGOVHVNG-TUFAYURCSA-N cortisol 17-butyrate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CO)(OC(=O)CCC)[C@@]1(C)C[C@@H]2O BMCQMVFGOVHVNG-TUFAYURCSA-N 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- CJXGPJZUDUOZDX-UHFFFAOYSA-N fluoromethanone Chemical group F[C]=O CJXGPJZUDUOZDX-UHFFFAOYSA-N 0.000 description 1
- 229960001524 hydrocortisone butyrate Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960001810 meprednisone Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- RJKFOVLPORLFTN-UHFFFAOYSA-N progesterone acetate Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2 RJKFOVLPORLFTN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IECKAVQTURBPON-UHFFFAOYSA-N trimethoxymethylbenzene Chemical compound COC(OC)(OC)C1=CC=CC=C1 IECKAVQTURBPON-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20620881A JPS58109500A (ja) | 1981-12-22 | 1981-12-22 | プレグナン系ステロイド１７α―エステル，２１―クロリド化合物の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20620881A JPS58109500A (ja) | 1981-12-22 | 1981-12-22 | プレグナン系ステロイド１７α―エステル，２１―クロリド化合物の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58109500A true JPS58109500A (ja) | 1983-06-29 |
| JPH0122280B2 JPH0122280B2 (enrdf_load_stackoverflow) | 1989-04-25 |
Family
ID=16519561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20620881A Granted JPS58109500A (ja) | 1981-12-22 | 1981-12-22 | プレグナン系ステロイド１７α―エステル，２１―クロリド化合物の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58109500A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61261304A (ja) * | 1985-05-15 | 1986-11-19 | Toho Titanium Co Ltd | オレフイン類重合用触媒成分の製造方法 |
-
1981
- 1981-12-22 JP JP20620881A patent/JPS58109500A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61261304A (ja) * | 1985-05-15 | 1986-11-19 | Toho Titanium Co Ltd | オレフイン類重合用触媒成分の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0122280B2 (enrdf_load_stackoverflow) | 1989-04-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AT363201B (de) | Verfahren zur herstellung von neuen 9alpha,21-dihalogen-11beta,17alpha-dihydroxy-6alpha- | |
| HRP990341A2 (en) | Process for the preparation of mometasone furoate | |
| JPS58109500A (ja) | プレグナン系ステロイド１７α―エステル，２１―クロリド化合物の製造法 | |
| US3020275A (en) | 21-nitrogen substituted steroids of the pregnane series and methods of preparing the same | |
| US2681353A (en) | Chlorination of keto-steroids | |
| JPH09510735A (ja) | スピロスタニルグリコシド性結晶 | |
| US3033874A (en) | 17beta-propenoyl steroids and process for preparing same | |
| JPH01131194A (ja) | プレグナノ［１７α，１６α−ｄ］オキサゾリン誘導体の製造法 | |
| US2773075A (en) | Chemical compounds and processes of preparing the same | |
| US4325881A (en) | Debromination | |
| US3452003A (en) | Process for the preparation of 5alpha-bromo-6beta-hydroxy steroids | |
| JPS6153297A (ja) | ９ａ―フルオル―又はクロル―コルチコステロイドエステル類の製造法 | |
| JPH0830076B2 (ja) | １６−デヒドロ−２０−オキソプレグナン誘導体，及びその製造方法 | |
| US3378550A (en) | Selected derivatives of 17, 17-difluoro-4-androstene-3-one | |
| US3641005A (en) | Process for the preparation of delta**4-6 6-difluoro - 320 - diketo - 17alp ha21-dihydr-oxypregnenes | |
| DE1169928B (de) | Verfahren zur Herstellung von 21-Brom-5ª‡- oder -5ª‰-pregnan-20-onen | |
| DE1593209C3 (de) | Verfahren zur 17 alpha-Alkylierung von 20-Ketosteroiden der Pregnanreihe und 17alpha-Alkylsteroide der Pregnanreihe | |
| US3082219A (en) | Method for the preparation of delta16-20-keto steroids | |
| US3098085A (en) | Process for the manufacture of 16alpha-methyl-allopregnanes substituted in the 21-position | |
| DE1903118C (de) | Verfahren zur Herstellung von 17 alpha Monoestern von 11 beta, 17 alpha 21-Tnhydroxysteroiden | |
| JP2006524664A (ja) | ソラナムグリコシドの合成 | |
| US2929826A (en) | Process for preparation of 20-keto-16-pregnenes from 16-acyloxy-20-keto pregnanes | |
| US2862937A (en) | Hydrocortisone and cortisone 21-(2-chloro-4-nitrobenzoates) | |
| BE634550A (enrdf_load_stackoverflow) | ||
| EP0041612B1 (de) | Verfahren zur Herstellung von 20-Carbonyl-Steroiden durch Abbau von Steroid-C22-Carbonsäuren |