CH638226A5 - Derivatives of 9-fluoroprednisolone - Google Patents

Derivatives of 9-fluoroprednisolone Download PDF

Info

Publication number: CH638226A5
Authority: CH; Switzerland
Prior art keywords: dione; hydroxy; pregnadiene; fluoro; compound according
Prior art date: 1977-03-21

Application number

CH296278A

Other languages

German (de)

English (en)

Inventor

Klaus Annen

Henry Laurent

Helmut Hofmeister

Rudolf Wiechert

Joachim-Friedrich Kapp

Hans Wendt

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.)

1977-03-21

Filing date

1978-03-17

Publication date

1983-09-15

1977-03-21 Priority claimed from DE2712862A external-priority patent/DE2712862C2/de

1978-03-03 Priority claimed from DE19782809732 external-priority patent/DE2809732C2/de

1978-03-17 Application filed by Schering Ag filed Critical Schering Ag

1983-09-15 Publication of CH638226A5 publication Critical patent/CH638226A5/de

Links

WAIJIHDWAKJCBX-BULBTXNYSA-N 9-Fluoroprednisolone Chemical class 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]3CCC2=C1 WAIJIHDWAKJCBX-BULBTXNYSA-N 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims description 53
125000004432 carbon atom Chemical group C* 0.000 claims description 14
238000000034 method Methods 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000004423 acyloxy group Chemical group 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 3
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 3
239000004593 Epoxy Substances 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 129
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 71
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
239000012043 crude product Substances 0.000 description 44
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 44
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
239000000741 silica gel Substances 0.000 description 43
229910002027 silica gel Inorganic materials 0.000 description 43
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 31
239000000243 solution Substances 0.000 description 26
230000008018 melting Effects 0.000 description 25
238000002844 melting Methods 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 22
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 18
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
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 11
239000005457 ice water Substances 0.000 description 11
235000011056 potassium acetate Nutrition 0.000 description 11
-1 for example Chemical class 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 8
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
210000003491 skin Anatomy 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
210000002683 foot Anatomy 0.000 description 5
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 5
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
206010030113 Oedema Diseases 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 4
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
239000002674 ointment Substances 0.000 description 4
229960005205 prednisolone Drugs 0.000 description 4
239000000126 substance Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 3
PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 description 3
239000003470 adrenal cortex hormone Substances 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical class 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 description 3
WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 description 3
WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
230000009885 systemic effect Effects 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
XCESQNFRBAHSGO-WRJHFWDFSA-N (8s,10s,13s,14s,17s)-17-acetyl-10,13-dimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)C3=CC[C@]4(C)[C@@H](C(=O)C)CC[C@H]4[C@@H]3CCC2=C1 XCESQNFRBAHSGO-WRJHFWDFSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 2
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
QIEPWCSVQYUPIY-LEKSSAKUSA-N Delta(1)-progesterone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 QIEPWCSVQYUPIY-LEKSSAKUSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
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206010020565 Hyperaemia Diseases 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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239000002253 acid Substances 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
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238000004140 cleaning Methods 0.000 description 2
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FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
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238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
239000006210 lotion Substances 0.000 description 2
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150000002905 orthoesters Chemical class 0.000 description 2
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239000002904 solvent Substances 0.000 description 2
238000001256 steam distillation Methods 0.000 description 2
125000000542 sulfonic acid group Chemical group 0.000 description 2
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
229940005605 valeric acid Drugs 0.000 description 2
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VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
QDYGIMAMLUKRLQ-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;hydrochloride Chemical compound Cl.CC1=CC=C(S(O)(=O)=O)C=C1 QDYGIMAMLUKRLQ-UHFFFAOYSA-N 0.000 description 1
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239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
208000010247 contact dermatitis Diseases 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000035876 healing Effects 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
DAPZDAPTZFJZTO-UHFFFAOYSA-N heptanoyl heptanoate Chemical compound CCCCCCC(=O)OC(=O)CCCCCC DAPZDAPTZFJZTO-UHFFFAOYSA-N 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000000544 hyperemic effect Effects 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
DISPOJHKKXSCLS-UHFFFAOYSA-N n-diaminophosphorylmethanamine Chemical compound CNP(N)(N)=O DISPOJHKKXSCLS-UHFFFAOYSA-N 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229960002446 octanoic acid Drugs 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
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 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 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
210000002345 respiratory system Anatomy 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
201000004700 rosacea Diseases 0.000 description 1
230000007017 scission Effects 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000000434 stratum corneum Anatomy 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
BQFPCTXLBRVFJL-UHFFFAOYSA-N triethoxymethylbenzene Chemical compound CCOC(OCC)(OCC)C1=CC=CC=C1 BQFPCTXLBRVFJL-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
210000002268 wool Anatomy 0.000 description 1

Classifications

- 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
- C07J5/0046—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 substituted in position 17 alfa
- C07J5/0053—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 substituted in position 17 alfa not substituted in position 16
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
- C07J7/0085—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by an halogen atom
- 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
- C07J71/001—Oxiranes
- C07J71/0015—Oxiranes at position 9(11)

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Bioinformatics & Cheminformatics (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH296278A 1977-03-21 1978-03-17 Derivatives of 9-fluoroprednisolone CH638226A5 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2712862A DE2712862C2 (de)	1977-03-21	1977-03-21	Derivate des 9-Fluorprednisolons, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE19782809732 DE2809732C2 (de)	1978-03-03	1978-03-03	Derivate des 9-Fluorprednisolons, Verfahren zu ihrer Herstellung, und pharmazeutische Präparate, die diese Wirkstoffe enthalten

Publications (1)

Publication Number	Publication Date
CH638226A5 true CH638226A5 (en)	1983-09-15

Family

ID=25771793

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH296278A CH638226A5 (en)	1977-03-21	1978-03-17	Derivatives of 9-fluoroprednisolone

Country Status (20)

Country	Link
JP (1)	JPS53130651A (ro)
AT (1)	AT365203B (ro)
AU (1)	AU525614B2 (ro)
CA (1)	CA1104124A (ro)
CH (1)	CH638226A5 (ro)
CS (1)	CS202591B2 (ro)
DD (1)	DD134955A5 (ro)
DK (1)	DK126378A (ro)
ES (1)	ES468107A1 (ro)
FR (1)	FR2384792A1 (ro)
GB (1)	GB1603281A (ro)
GR (1)	GR70385B (ro)
IE (1)	IE46584B1 (ro)
IL (1)	IL54308A (ro)
IT (1)	IT1095477B (ro)
LU (1)	LU79271A1 (ro)
NO (1)	NO151043C (ro)
NZ (1)	NZ186735A (ro)
RO (1)	RO81525B (ro)
SE (1)	SE431656B (ro)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2853785A1 (de) *	1978-12-11	1980-06-19	Schering Ag	Neue prednison-derivate, verfahren zu ihrer herstellung, diese verbindungen enthaltende pharmazeutische praeparate und deren verwendung
JPH07116215B2 (ja) *	1989-04-19	1995-12-13	エスエス製薬株式会社	新規なステロイド化合物
JPH07213320A (ja) *	1994-02-04	1995-08-15	Daiwa:Kk	長尺物用バック

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2055221A1 (en) *	1970-11-10	1972-05-18	Laboratorio Chimico Farmaceutico Dr. P. Blasina S.R.L., Mailand (Italien)	17-acyloxy-3-keto-pregn-4-enes prepn - by acylating 17-hydroxy steroids in presence ofstannic chloride
CH529739A (fr) *	1972-02-28	1972-10-31	Sdc Steroidi Dev Co	Procédé pour la préparation d'un stéroïde de la série des prégnadiènes
US3832366A (en) *	1973-07-30	1974-08-27	Squibb & Sons Inc	Process for preparing 21-chloro-17-acyloxy-20-ketosteroids

1978
- 1978-03-17 CH CH296278A patent/CH638226A5/de not_active IP Right Cessation
- 1978-03-17 DD DD78204259A patent/DD134955A5/xx unknown
- 1978-03-18 RO RO93558A patent/RO81525B/ro unknown
- 1978-03-20 NO NO780984A patent/NO151043C/no unknown
- 1978-03-20 JP JP3225378A patent/JPS53130651A/ja active Granted
- 1978-03-20 SE SE7803168A patent/SE431656B/sv not_active IP Right Cessation
- 1978-03-20 AT AT0195978A patent/AT365203B/de not_active IP Right Cessation
- 1978-03-20 NZ NZ186735A patent/NZ186735A/xx unknown
- 1978-03-20 LU LU79271A patent/LU79271A1/de unknown
- 1978-03-20 GR GR55756A patent/GR70385B/el unknown
- 1978-03-20 GB GB10925/78A patent/GB1603281A/en not_active Expired
- 1978-03-20 IT IT21364/78A patent/IT1095477B/it active
- 1978-03-20 CA CA299,299A patent/CA1104124A/en not_active Expired
- 1978-03-20 IE IE545/78A patent/IE46584B1/en unknown
- 1978-03-20 IL IL54308A patent/IL54308A/xx unknown
- 1978-03-21 CS CS781785A patent/CS202591B2/cs unknown
- 1978-03-21 ES ES468107A patent/ES468107A1/es not_active Expired
- 1978-03-21 AU AU34346/78A patent/AU525614B2/en not_active Expired
- 1978-03-21 FR FR7808099A patent/FR2384792A1/fr active Granted
- 1978-03-21 DK DK126378A patent/DK126378A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
AT365203B (de)	1981-12-28
LU79271A1 (de)	1978-06-29
IE780545L (en)	1978-09-21
IT1095477B (it)	1985-08-10
CS202591B2 (en)	1981-01-30
DD134955A5 (de)	1979-04-04
FR2384792A1 (fr)	1978-10-20
IE46584B1 (en)	1983-07-27
AU525614B2 (en)	1982-11-18
IL54308A0 (en)	1978-06-15
RO81525A (ro)	1983-04-29
JPS6131116B2 (ro)	1986-07-17
GR70385B (ro)	1982-10-05
NO151043C (no)	1985-01-30
SE7803168L (sv)	1978-09-22
AU3434678A (en)	1979-09-27
RO81525B (ro)	1983-04-30
GB1603281A (en)	1981-11-25
NZ186735A (en)	1980-10-24
DK126378A (da)	1978-09-22
NO780984L (no)	1978-09-22
ES468107A1 (es)	1979-07-01
FR2384792B1 (ro)	1980-04-04
IL54308A (en)	1984-03-30
SE431656B (sv)	1984-02-20
JPS53130651A (en)	1978-11-14
NO151043B (no)	1984-10-22
ATA195978A (de)	1981-05-15
IT7821364A0 (it)	1978-03-20
CA1104124A (en)	1981-06-30

Legal Events

Date	Code	Title	Description
1990-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0072547B1 (de)	1986-03-26	Neue 6-alpha-Methylprednisolon-Derivate ihre Herstellung und Verwendung
EP0100874A2 (de)	1984-02-22	Neue 6,16-Dimethylkortikoide, ihre Herstellung und Verwendung
EP0110041B1 (de)	1987-07-29	Neue 6alpha-Methylkortikoide, ihre Herstellung und Verwendung
EP0072546B1 (de)	1985-10-09	Neue Hydrocortison-Derivate, ihre Herstellung und Verwendung
CH644614A5 (de)	1984-08-15	17-alpha-acyloxy-5-beta- und 17-alpha-acyloxy-5-alpha-corticoide.
DE2645104C2 (de)	1986-04-24	11&beta;-Hydroxy-1,4,8-pregnatrien-3,20-dion-Derivate und Verfahren zu ihrer Herstellung
CH638226A5 (en)	1983-09-15	Derivatives of 9-fluoroprednisolone
DE2617655C2 (de)	1984-11-08	Kortikoide, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
EP0149464A2 (de)	1985-07-24	6-Alpha,16-beta-Dimethylkortikoide
EP0003341B1 (de)	1984-06-27	11,17-substituierte Pregnane, ihre Herstellung und Verwendung zur Herstellung von pharmazeutischen Präparaten
EP0149222A2 (de)	1985-07-24	Neue 6alpha, 16alpha-Dimethylkortikoide
DE2852055C2 (ro)	1988-06-09
CH631997A5 (en)	1982-09-15	Process for the preparation of novel derivatives of 9-chloro-prednisolone
AT372966B (de)	1983-12-12	Verfahren zur herstellung von neuen 9-fluorprednisolon-derivaten
DE2712862C2 (de)	1985-10-03	Derivate des 9-Fluorprednisolons, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2645105C2 (de)	1986-03-13	Derivate des 9-Chlorprednisolons, Verfahren zu ihrer Herstellung und diese enthaltendes pharmazeutisches Präparat
DE2809732C2 (de)	1986-04-24	Derivate des 9-Fluorprednisolons, Verfahren zu ihrer Herstellung, und pharmazeutische Präparate, die diese Wirkstoffe enthalten
DE2632678C2 (de)	1986-02-27	6&alpha;-Fluor-12&alpha;-Halogen-Kortikoide und Verfahren zu ihrer Herstellung
AT370112B (de)	1983-03-10	Verfahren zur herstellung neuer kortikoide
DE2150268A1 (de)	1973-04-12	Neue pregnansaeure-derivate
EP0164298A2 (de)	1985-12-11	Neue 6alpha-Methyl-D-homo-kortikoide
EP0012271B1 (de)	1984-05-02	Neue Prednison-Derivate, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende pharmazeutische Präparate und deren Verwendung
AT373604B (de)	1984-02-10	Verfahren zur herstellung von neuen derivaten des 9-chlorprednisolons
DE2742982C2 (de)	1985-12-12	9-Chlorprednisolon-Derivate, Verfahren zu deren Herstellung und diese enthaltendes pharmazeutisches Präparat
EP0049783B1 (de)	1986-10-22	D-Homo-kortikoide, ihre Herstellung und Verwendung