DD146296A5 - Verfahren zur herstellung von kortikoid-21-sulfopropionaten - Google Patents

Verfahren zur herstellung von kortikoid-21-sulfopropionaten Download PDF

Info

Publication number: DD146296A5
Authority: DD; German Democratic Republic
Prior art keywords: corticoid; hydrogen atom; salts; general formula; dione
Prior art date: 1978-10-04

Application number

DD79215930A

Other languages

German (de)

English (en)

Inventor

Henry Laurent

Peter Esperling

Joachim-Friedrich Kapp

Rudolf Wiechert

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.)

1978-10-04

Filing date

1979-10-01

Publication date

1981-02-04

1978-10-04 Priority claimed from DE19782843690 external-priority patent/DE2843690A1/de

1979-08-06 Priority claimed from DE19792932166 external-priority patent/DE2932166A1/de

1979-10-01 Application filed by Schering Ag filed Critical Schering Ag

1981-02-04 Publication of DD146296A5 publication Critical patent/DD146296A5/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 17
238000000034 method Methods 0.000 title claims abstract description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
150000003839 salts Chemical class 0.000 claims abstract description 21
RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 claims abstract description 19
239000003470 adrenal cortex hormone Substances 0.000 claims abstract description 16
239000003246 corticosteroid Substances 0.000 claims abstract description 15
229910052731 fluorine Inorganic materials 0.000 claims abstract description 15
229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
230000003110 anti-inflammatory effect Effects 0.000 claims abstract 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 13
125000001153 fluoro group Chemical group F* 0.000 claims description 13
229910052708 sodium Inorganic materials 0.000 claims description 13
239000011734 sodium Substances 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 5
150000003863 ammonium salts Chemical class 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
WBGKAOURNYRYBT-UHFFFAOYSA-N 2-sulfopropanoic acid Chemical compound OC(=O)C(C)S(O)(=O)=O WBGKAOURNYRYBT-UHFFFAOYSA-N 0.000 claims description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
229910052791 calcium Inorganic materials 0.000 claims description 2
239000011575 calcium Substances 0.000 claims description 2
125000002345 steroid group Chemical group 0.000 claims 1
125000004043 oxo group Chemical group O=* 0.000 abstract description 2
150000003431 steroids Chemical class 0.000 abstract description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
239000000460 chlorine Chemical group 0.000 abstract 2
239000011737 fluorine Chemical group 0.000 abstract 2
239000001257 hydrogen Substances 0.000 abstract 2
229910052739 hydrogen Inorganic materials 0.000 abstract 2
230000000694 effects Effects 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
-1 for example Chemical class 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 28
230000008018 melting Effects 0.000 description 27
238000002844 melting Methods 0.000 description 27
159000000000 sodium salts Chemical class 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical class [Na+].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)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 4
230000001154 acute effect Effects 0.000 description 4
OGPWIDANBSLJPC-RFPWEZLHSA-N diflucortolone Chemical class C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O OGPWIDANBSLJPC-RFPWEZLHSA-N 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
230000035939 shock Effects 0.000 description 4
GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical class O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 4
RVLHNHNPUBWSEE-UHFFFAOYSA-N 2,2-dioxooxathiolan-5-one Chemical compound O=C1CCS(=O)(=O)O1 RVLHNHNPUBWSEE-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
206010020751 Hypersensitivity Diseases 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
206010040070 Septic Shock Diseases 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229960004091 diflucortolone Drugs 0.000 description 3
229960004584 methylprednisolone Drugs 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
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 3
235000012424 soybean oil Nutrition 0.000 description 3
239000003549 soybean oil Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
229960005294 triamcinolone Drugs 0.000 description 3
239000008215 water for injection Substances 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
OURSFPZPOXNNKX-UHFFFAOYSA-N 3-sulfopropanoic acid Chemical compound OC(=O)CCS(O)(=O)=O OURSFPZPOXNNKX-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
208000026935 allergic disease Diseases 0.000 description 2
230000000172 allergic effect Effects 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
239000000292 calcium oxide Substances 0.000 description 2
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
229960001334 corticosteroids Drugs 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical class 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 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000003889 eye drop Substances 0.000 description 2
229940012356 eye drops Drugs 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
229910003002 lithium salt Inorganic materials 0.000 description 2
159000000002 lithium salts Chemical class 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
229940100662 nasal drops Drugs 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
229960005205 prednisolone Drugs 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000003826 tablet Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
LDDMACCNBZAMSG-BDVNFPICSA-N (2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal Chemical compound CN[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO LDDMACCNBZAMSG-BDVNFPICSA-N 0.000 description 1
JDPURKGEQMLZNC-HPMPOATDSA-N (8S,9S,10R,13R,14S,17S)-10,13-dimethyl-17-propyl-6,7,8,9,11,12,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CCC)[C@@]1(C)CC2 JDPURKGEQMLZNC-HPMPOATDSA-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
CPUKWYXYHPOQJH-RDQPJNLGSA-N (8r,9s,10s,13s,14s)-17-ethenyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(=CC4)C=C)[C@@H]4[C@@H]3CCC21 CPUKWYXYHPOQJH-RDQPJNLGSA-N 0.000 description 1
MBJJLHWSFGHIAA-UDCWSGSHSA-N (8s,9s,10r,13s,14s,17s)-10,13-dimethyl-17-(2,2,2-trihydroxyacetyl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)C(O)(O)O)[C@@H]4[C@@H]3CCC2=C1 MBJJLHWSFGHIAA-UDCWSGSHSA-N 0.000 description 1
SYVFBJQHOGXAMY-XUCMERPOSA-N (8s,9s,10r,13s,14s,17s)-10,13-dimethyl-17-propanoyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)CC)[C@@]1(C)CC2 SYVFBJQHOGXAMY-XUCMERPOSA-N 0.000 description 1
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
229930182837 (R)-adrenaline Natural products 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
MWUISCCBFHLWLY-UHFFFAOYSA-N 1,2-dimethylpiperidine Chemical compound CC1CCCCN1C MWUISCCBFHLWLY-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NQPKHKUCLNQHER-UHFFFAOYSA-N 1-fluorohexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCC(O)F NQPKHKUCLNQHER-UHFFFAOYSA-N 0.000 description 1
YQOPNAOQGQSUHF-UHFFFAOYSA-N 1-propan-2-ylpyrrolidine Chemical compound CC(C)N1CCCC1 YQOPNAOQGQSUHF-UHFFFAOYSA-N 0.000 description 1
LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 1
IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical compound CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 description 1
229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
GVSVBXZWEWXKJB-ZEQQQVMLSA-N 3-[2-[(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-3-oxopropane-1-sulfonic acid Chemical compound S(=O)(=O)(O)CCC(=O)OCC([C@H]1CC[C@H]2[C@@H]3C=CC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O)=O GVSVBXZWEWXKJB-ZEQQQVMLSA-N 0.000 description 1
ZPDAFFXGSNEJMX-ZEQQQVMLSA-N 3-[2-[(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-3-oxopropane-1-sulfonic acid Chemical compound S(=O)(=O)(O)CCC(=O)OCC([C@H]1CC[C@H]2[C@@H]3CCC4=CC(C=C[C@]4(C)[C@H]3CC[C@]12C)=O)=O ZPDAFFXGSNEJMX-ZEQQQVMLSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
206010002199 Anaphylactic shock Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
206010048962 Brain oedema Diseases 0.000 description 1
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
206010008190 Cerebrovascular accident Diseases 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
241000223211 Curvularia lunata Species 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
241000792859 Enema Species 0.000 description 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
206010020850 Hyperthyroidism Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
206010022941 Iridocyclitis Diseases 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
206010034277 Pemphigoid Diseases 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
239000004146 Propane-1,2-diol Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
206010037423 Pulmonary oedema Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010039085 Rhinitis allergic Diseases 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
229920002472 Starch Polymers 0.000 description 1
208000006011 Stroke Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
206010053615 Thermal burn Diseases 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
208000027076 Uveal disease Diseases 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
208000010981 acute adrenal insufficiency Diseases 0.000 description 1
231100001133 acute intoxication condition Toxicity 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000011360 adjunctive therapy Methods 0.000 description 1
238000005273 aeration Methods 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
201000010105 allergic rhinitis Diseases 0.000 description 1
CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
201000004612 anterior uveitis Diseases 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
208000010217 blepharitis Diseases 0.000 description 1
230000037396 body weight Effects 0.000 description 1
208000006752 brain edema Diseases 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
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 1
229960005091 chloramphenicol Drugs 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
201000009151 chronic rhinitis Diseases 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
208000018631 connective tissue disease Diseases 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
229960003957 dexamethasone Drugs 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003221 ear drop Substances 0.000 description 1
229940047652 ear drops Drugs 0.000 description 1
239000002158 endotoxin Substances 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
229960005139 epinephrine Drugs 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical group C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000006698 induction Effects 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
201000004614 iritis Diseases 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
208000030159 metabolic disease Diseases 0.000 description 1
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
210000002200 mouth mucosa Anatomy 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
ZFTHBNICAKESRH-UHFFFAOYSA-N n-methoxy-n-propan-2-ylaniline Chemical compound CON(C(C)C)C1=CC=CC=C1 ZFTHBNICAKESRH-UHFFFAOYSA-N 0.000 description 1
239000007923 nasal drop Substances 0.000 description 1
231100000957 no side effect Toxicity 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
229940124624 oral corticosteroid Drugs 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
101150114893 oxyR gene Proteins 0.000 description 1
FDJABJJEKWDNQO-UHFFFAOYSA-N pentane;propan-2-one Chemical compound CC(C)=O.CCCCC FDJABJJEKWDNQO-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
229960001802 phenylephrine Drugs 0.000 description 1
ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
239000000047 product Substances 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
235000019260 propionic acid Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
208000005333 pulmonary edema Diseases 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
230000001359 rheumatologic effect Effects 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
KQHKITXZJDOIOD-UHFFFAOYSA-M sodium;3-sulfobenzoate Chemical compound [Na+].OS(=O)(=O)C1=CC=CC(C([O-])=O)=C1 KQHKITXZJDOIOD-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
208000001319 vasomotor rhinitis Diseases 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
- C12P33/06—Hydroxylating
- C12P33/08—Hydroxylating at 11 position
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
- C07J53/005—3 membered carbocyclic rings in position 12
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
General Chemical & Material Sciences (AREA)
Microbiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
Genetics & Genomics (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

DD79215930A 1978-10-04 1979-10-01 Verfahren zur herstellung von kortikoid-21-sulfopropionaten DD146296A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19782843690 DE2843690A1 (de)	1978-10-04	1978-10-04	Kortikoid-2l-sulfopropionate und deren salze, verfahren zu ihrer herstellung und pharmazeutische praeparate, die diese verbindungen enthalten
DE19792932166 DE2932166A1 (de)	1979-08-06	1979-08-06	Kortikoid-21-sulfopropionate und deren salze, verfahren zu ihrer herstellung und pharmazeutische praeparate, die diese verbindungen enthalten

Publications (1)

Publication Number	Publication Date
DD146296A5 true DD146296A5 (de)	1981-02-04

Family

ID=25775997

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79215930A DD146296A5 (de)	1978-10-04	1979-10-01	Verfahren zur herstellung von kortikoid-21-sulfopropionaten

Country Status (13)

Country	Link
US (1)	US4296109A (da)
EP (1)	EP0010056B1 (da)
CA (1)	CA1127630A (da)
CS (1)	CS215030B2 (da)
DD (1)	DD146296A5 (da)
DE (1)	DE2966092D1 (da)
DK (1)	DK404879A (da)
ES (1)	ES484706A1 (da)
GB (1)	GB2034715A (da)
GR (1)	GR74136B (da)
HU (1)	HU183000B (da)
IE (1)	IE48954B1 (da)
SU (1)	SU818489A3 (da)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4472392A (en) *	1983-01-21	1984-09-18	The Upjohn Company	Sulfonate containing ester prodrugs of corticosteroids
US4469689A (en) *	1983-03-30	1984-09-04	The Upjohn Company	Sulfonate containing ester prodrugs of corticosteroids
CA1310009C (en) *	1984-03-28	1992-11-10	John Mark Braughler	Ester prodrugs of steroids
US4948533A (en) *	1984-03-28	1990-08-14	The Upjohn Company	11a-hydroxy steroid diester
US4588718A (en) *	1984-03-28	1986-05-13	The Upjohn Company	Carboxy containing ester prodrugs of corticosteroids
ZA876171B (en) *	1986-08-21	1988-10-26	Broadbent James Meredyth	Active principle isolated from shark tissue
AU597723B2 (en) *	1986-08-21	1990-06-07	J.W. Broadbent Nominees Pty. Ltd.	Sodium scymnol sulphate isolated form shark tissues
EP0374166B1 (en) *	1987-07-16	1993-01-07	The Upjohn Company	Amine salts of alkane-1,n-dicarboxylic acid mono-(2-sulfato-ethyl)amides
US5250711A (en) *	1987-07-16	1993-10-05	The Upjohn Company	Amine salts of alkane-1,n-dicarboxylic acid mono-(2-sulfato-ethyl) amides
DE4334823C2 (de) *	1993-10-09	1998-09-17	Schering Ag	Verfahren zur Herstellung von Schwefelsäurehalbestern von Estrogenen
US7074570B2 (en) *	2001-05-23	2006-07-11	Ge Healthcare Bio-Sciences Ab	Peptide fragmentation
CA2448534A1 (en) *	2001-05-23	2002-11-28	Harold L. Vaughn	Peptide analysis using a solid support
US20040171070A1 (en) *	2002-05-20	2004-09-02	Ramagauri Bhikhabhai	Peptide analysis using a solid support

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3089881A (en) *	1957-10-29	1963-05-14	Schering Corp	Sulfocarboxylic acid esters of hydroxylated steroids
DE1090207B (de) *	1958-04-21	1960-10-06	Chimiotherapie Lab Franc	Verfahren zur Herstellung wasserloeslicher Corticosteroidderivate
FR1392048A (fr) *	1964-02-21	1965-03-12	Ile D Etudes Et De Brevets Nov	Procédé de fabrication de composés stéroïdes de la série de l'androstane et de l'oestrane
DE2703543C2 (de) *	1977-01-26	1985-06-05	Schering AG, 1000 Berlin und 4709 Bergkamen	2l-(3-Benzoylpropionyloxy)-11β,17α-dihydroxy-1,4-pregnadien-3,20-dion, Verfahren zu seiner Herstellung und diese Verbindung enthaltende pharmazeutische Präparate

1979
- 1979-09-27 DK DK404879A patent/DK404879A/da not_active Application Discontinuation
- 1979-09-27 SU SU792822051A patent/SU818489A3/ru active
- 1979-10-01 DD DD79215930A patent/DD146296A5/de unknown
- 1979-10-02 GR GR60162A patent/GR74136B/el unknown
- 1979-10-03 ES ES484706A patent/ES484706A1/es not_active Expired
- 1979-10-03 HU HU79SCHE694A patent/HU183000B/hu unknown
- 1979-10-03 DE DE7979710095T patent/DE2966092D1/de not_active Expired
- 1979-10-03 EP EP79710095A patent/EP0010056B1/de not_active Expired
- 1979-10-03 CA CA336,867A patent/CA1127630A/en not_active Expired
- 1979-10-03 IE IE1879/79A patent/IE48954B1/en not_active IP Right Cessation
- 1979-10-03 GB GB7934299A patent/GB2034715A/en not_active Withdrawn
- 1979-10-04 CS CS796767A patent/CS215030B2/cs unknown
- 1979-10-09 US US06/081,947 patent/US4296109A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ES484706A1 (es)	1980-06-16
HU183000B (en)	1984-03-28
US4296109A (en)	1981-10-20
GR74136B (da)	1984-06-06
DE2966092D1 (en)	1983-09-29
CA1127630A (en)	1982-07-13
DK404879A (da)	1980-04-05
IE791879L (en)	1980-04-04
IE48954B1 (en)	1985-06-26
EP0010056A1 (de)	1980-04-16
GB2034715A (en)	1980-06-11
CS215030B2 (en)	1982-06-25
SU818489A3 (ru)	1981-03-30
EP0010056B1 (de)	1983-08-24

Publication	Publication Date	Title
DE2323215C3 (de)	1978-03-30	Pregna-l,4-dien-ll-ol-3,20-dione, Verfahren zu deren Herstellung und sie enthaltende Arzneimittel
DE2912331A1 (de)	1979-10-18	Neue 17 beta -thiocarboxylate von 3-oxo-androst-4-en- bzw. -androsta-1,4-dienderivaten, ihre herstellung und diese enthaltende arzneimittel
DE69720996T2 (de)	2004-02-05	Neue pharmazeutische zusammensetzungen von steroid-nitratester zur verwendung als enzündungshemmer
DD146296A5 (de)	1981-02-04	Verfahren zur herstellung von kortikoid-21-sulfopropionaten
DE69004797T2 (de)	1994-03-31	Verwendung von steroiden als antipilzmittel.
US3206359A (en)	1965-09-14	Galacturonides of the anti-inflammatory pregnane series
DE69518258T2 (de)	2001-02-01	Kortikoidderivate und pharmazeutische und kosmetische Zusammensetzungen
US4081538A (en)	1978-03-28	Aldosterone antagonists
DE69609870T2 (de)	2001-01-25	17beta-(2-oxo-tetrahydrofuran-4-yl)-thio-androstane derivate (17beta-(gamma-buttersäure-lacton)-thio derivate) zur behandlung von entzündungen, pharmazeutische präparate davon und ein verfahren zu ihrer herstellung
DE2232827A1 (de)	1973-01-18	Neue steroide und verfahren zu ihrer herstellung
EP0005758B1 (de)	1983-05-18	Verfahren zum Aufbau der Hydroxyacetyl-Seitenkette von Steroiden des Pregnan-Typs, neue 21-Hydroxy-20-oxo-17alpha-pregnan-Verbindungen und pharmazeutische Präparate enthaltend dieselben
DE2162592A1 (de)	1972-07-06	Steroide der 5 alpha-Pregnan-Reihen
DE2932166A1 (de)	1981-02-26	Kortikoid-21-sulfopropionate und deren salze, verfahren zu ihrer herstellung und pharmazeutische praeparate, die diese verbindungen enthalten
DD141523A5 (de)	1980-05-07	Verfahren zur herstellung von kortikoiden
DE2843690A1 (de)	1980-04-24	Kortikoid-2l-sulfopropionate und deren salze, verfahren zu ihrer herstellung und pharmazeutische praeparate, die diese verbindungen enthalten
US3153644A (en)	1964-10-20	16alpha, 17alpha-(2-halo-1-di-lower-alkylamino-2-haloalkylidenedioxy)-steroids and process for the preparation thereof
US3651049A (en)	1972-03-21	17alpha 21 alkenylidene dioxy derivatives of pregnane and process for preparation thereof
US3153645A (en)	1964-10-20	17alpha, 21-(2-halo-1-di-lower-alkylamino-2-haloalkylidenedioxy)-steroids and process for the preparation thereof
DE2048812A1 (de)	1971-05-06	Ein neues 6alpha Methyl 19 nor pro gesteron und ein Verfahren zu dessen Her stellung
US3641070A (en)	1972-02-08	Halogen-pregnadienes
CH531493A (de)	1972-12-15	Verfahren zur Herstellung neuer Steroide der Pregnanreihe
US3163664A (en)	1964-12-29	21-hemi-alpha, beta-dialkylsuccinates of corticoids
DE1443176A1 (de)	1968-12-19	6 alpha-Fluor-16-beta-methyl-4-pregnene und -1,4-pregnadiene und Verfahren zu ihrer Herstellung
DE1618493A1 (de)	1970-10-29	Verfahren zur Herstellung von halogenierten Steroiden
DE1211194B (de)	1966-02-24	Verfahren zur Herstellung von 6alpha, 9alpha-Difluor-16alpha-methyl-delta 1,4-pregnadien-11beta, 21-diol-3, 20-dionen