JPS6131116B2 - - Google Patents

Info

Publication number: JPS6131116B2
Authority: JP; Japan
Prior art keywords: dione; pregnadiene; hydroxy; fluoro; derivative according
Prior art date: 1977-03-21
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.): Expired

Application number

JP53032253A

Other languages

English (en)

Japanese (ja)

Other versions

JPS53130651A (en

Inventor

Annen Kurausu

Roorento Henrii

Hoofumaisutaa Herumuuto

Uiihieruto Ruudorufu

Uento Hansu

Furiitoritsuhi Katsupu Yoahimu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Pharma AG

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

1978-03-20

Publication date

1986-07-17

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

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

1978-03-20 Application filed by Schering AG filed Critical Schering AG

1978-11-14 Publication of JPS53130651A publication Critical patent/JPS53130651A/ja

1986-07-17 Publication of JPS6131116B2 publication Critical patent/JPS6131116B2/ja

Status Granted legal-status Critical Current

Links

125000004432 carbon atom Chemical group C* 0.000 claims description 20
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 claims description 10
150000001875 compounds Chemical class 0.000 claims description 10
-1 hydroxy-21-valeryloxy-1,4-pregnadiene-3,20-dione Chemical compound 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 7
125000004423 acyloxy group Chemical group 0.000 claims description 7
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 3
238000003776 cleavage reaction Methods 0.000 claims description 3
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 3
150000002905 orthoesters Chemical class 0.000 claims description 3
230000007017 scission Effects 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000003700 epoxy group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 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 claims 10
WAIJIHDWAKJCBX-BULBTXNYSA-N 9-Fluoroprednisolone 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]3CCC2=C1 WAIJIHDWAKJCBX-BULBTXNYSA-N 0.000 claims 8
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
229940121363 anti-inflammatory agent Drugs 0.000 claims 1
239000002260 anti-inflammatory agent Substances 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 172
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 168
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 73
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
239000000203 mixture Substances 0.000 description 56
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
239000012043 crude product Substances 0.000 description 43
239000000741 silica gel Substances 0.000 description 43
229910002027 silica gel Inorganic materials 0.000 description 43
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 27
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
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 17
238000000034 method Methods 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
239000005457 ice water Substances 0.000 description 11
235000011056 potassium acetate Nutrition 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 8
ZOCUOMKMBMEYQV-GSLJADNHSA-N 9alpha-Fluoro-11beta,17alpha,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate Chemical class C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ZOCUOMKMBMEYQV-GSLJADNHSA-N 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
238000012360 testing method Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 6
229960005205 prednisolone Drugs 0.000 description 6
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
210000003491 skin Anatomy 0.000 description 5
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 4
238000006243 chemical reaction Methods 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
238000000354 decomposition reaction Methods 0.000 description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 4
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 4
239000002674 ointment Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
230000009885 systemic effect Effects 0.000 description 4
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-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
DSQVKHUTJHFJPO-VDBJYJQWSA-N C[C@]12CC=C3[C@@H](CCC4=CC(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)CO Chemical compound C[C@]12CC=C3[C@@H](CCC4=CC(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)CO DSQVKHUTJHFJPO-VDBJYJQWSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
230000015572 biosynthetic process 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
239000012442 inert solvent Substances 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000001256 steam distillation Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
WUUGBBSQIZQMJR-ONKRVSLGSA-N (8S,10S,13S,14S,17R)-17-(2-fluoroacetyl)-17-hydroxy-10,13-dimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one Chemical compound FCC([C@]1(CC[C@H]2[C@@H]3CCC4=CC(C=C[C@]4(C)C3=CC[C@]12C)=O)O)=O WUUGBBSQIZQMJR-ONKRVSLGSA-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
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
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
DNFMJYXRIMLMBZ-UHFFFAOYSA-N Clemizole hydrochloride Chemical compound [Cl-].C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2N=C1C[NH+]1CCCC1 DNFMJYXRIMLMBZ-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
239000004593 Epoxy Substances 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
241000700159 Rattus Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
206010047139 Vasoconstriction Diseases 0.000 description 2
RJIVAPMOIRJSHF-WWMZEODYSA-N [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-oxoethyl] 2,2-dimethylpropanoate Chemical compound CC(C(=O)OCC([C@H]1CC[C@H]2[C@@H]3CCC4=CC(C=C[C@]4(C)[C@H]3CC[C@]12C)=O)=O)(C)C RJIVAPMOIRJSHF-WWMZEODYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000000605 extraction Methods 0.000 description 2
CTIKAHQFRQTTAY-UHFFFAOYSA-N fluoro(trimethyl)silane Chemical compound C[Si](C)(C)F CTIKAHQFRQTTAY-UHFFFAOYSA-N 0.000 description 2
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
230000000544 hyperemic effect Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 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
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
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 2
239000011541 reaction mixture Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000000542 sulfonic acid group Chemical group 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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
230000025033 vasoconstriction Effects 0.000 description 2
FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
JTHTUQUSBOTPBB-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-4-methyl-2-pyrrolidin-1-ylbenzimidazole Chemical group C1CCCN1C1=NC=2C(C)=CC=CC=2N1CC1=CC=C(Cl)C=C1 JTHTUQUSBOTPBB-UHFFFAOYSA-N 0.000 description 1
FOTITZRWZUAVPH-UHFFFAOYSA-N 2-phenylpropanoyl chloride Chemical compound ClC(=O)C(C)C1=CC=CC=C1 FOTITZRWZUAVPH-UHFFFAOYSA-N 0.000 description 1
MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-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
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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010068172 Anal pruritus Diseases 0.000 description 1
239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
229920000298 Cellophane Polymers 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XGIAHMUOCFHQTI-UHFFFAOYSA-N Cl.Cl.Cl.Cl.CC Chemical compound Cl.Cl.Cl.Cl.CC XGIAHMUOCFHQTI-UHFFFAOYSA-N 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
206010012442 Dermatitis contact Diseases 0.000 description 1
206010012455 Dermatitis exfoliative Diseases 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
206010020565 Hyperaemia 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
241000186359 Mycobacterium Species 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
201000009053 Neurodermatitis Diseases 0.000 description 1
206010030124 Oedema peripheral Diseases 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
241001303601 Rosacea Species 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
CZESFSQZSDTEIW-ZMBSQWCGSA-N [2-[(8S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 2,2-dimethylpropanoate Chemical compound CC(C(=O)OCC([C@H]1CC[C@H]2[C@@H]3CCC4=CC(C=C[C@]4(C)C3=CC[C@]12C)=O)=O)(C)C CZESFSQZSDTEIW-ZMBSQWCGSA-N 0.000 description 1
YZNRCFWCXOCOJG-RJBKZOIGSA-N [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-oxoethyl] 2-methylpropanoate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C(C)C)[C@@]1(C)CC2 YZNRCFWCXOCOJG-RJBKZOIGSA-N 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
239000002585 base Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003153 chemical reaction reagent 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
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
239000012141 concentrate Substances 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
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
230000006378 damage Effects 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002168 ethanoic acid 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
239000006260 foam Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
DAPZDAPTZFJZTO-UHFFFAOYSA-N heptanoyl heptanoate Chemical compound CCCCCCC(=O)OC(=O)CCCCCC DAPZDAPTZFJZTO-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 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
230000003902 lesion Effects 0.000 description 1
201000011486 lichen planus Diseases 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
206010025135 lupus erythematosus Diseases 0.000 description 1
230000014759 maintenance of location Effects 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
OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 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
239000000825 pharmaceutical preparation Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
239000011505 plaster Substances 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
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 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
239000002994 raw material Substances 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
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
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
150000008027 tertiary esters Chemical class 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
230000002992 thymic effect Effects 0.000 description 1
210000001519 tissue Anatomy 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
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
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)

JP3225378A 1977-03-21 1978-03-20 99fluoropredonizolone derivative process for preparing same and antiphologistic agent Granted JPS53130651A (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 (2)

Publication Number	Publication Date
JPS53130651A JPS53130651A (en)	1978-11-14
JPS6131116B2 true JPS6131116B2 (ro)	1986-07-17

Family

ID=25771793

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3225378A Granted JPS53130651A (en)	1977-03-21	1978-03-20	99fluoropredonizolone derivative process for preparing same and antiphologistic agent

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)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH07213320A (ja) *	1994-02-04	1995-08-15	Daiwa:Kk	長尺物用バック

Families Citing this family (2)

* 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

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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH07213320A (ja) *	1994-02-04	1995-08-15	Daiwa:Kk	長尺物用バック

Also Published As

Publication number	Publication date
GB1603281A (en)	1981-11-25
IE780545L (en)	1978-09-21
CA1104124A (en)	1981-06-30
NZ186735A (en)	1980-10-24
IL54308A0 (en)	1978-06-15
FR2384792B1 (ro)	1980-04-04
AU525614B2 (en)	1982-11-18
AT365203B (de)	1981-12-28
IL54308A (en)	1984-03-30
ES468107A1 (es)	1979-07-01
NO780984L (no)	1978-09-22
SE7803168L (sv)	1978-09-22
IT1095477B (it)	1985-08-10
AU3434678A (en)	1979-09-27
DD134955A5 (de)	1979-04-04
RO81525B (ro)	1983-04-30
SE431656B (sv)	1984-02-20
RO81525A (ro)	1983-04-29
FR2384792A1 (fr)	1978-10-20
IE46584B1 (en)	1983-07-27
DK126378A (da)	1978-09-22
GR70385B (ro)	1982-10-05
NO151043B (no)	1984-10-22
LU79271A1 (de)	1978-06-29
JPS53130651A (en)	1978-11-14
CS202591B2 (en)	1981-01-30
CH638226A5 (en)	1983-09-15
IT7821364A0 (it)	1978-03-20
NO151043C (no)	1985-01-30
ATA195978A (de)	1981-05-15

Publication	Publication Date	Title
CA2050812C (en)	2003-07-29	Pregna-1,4-diene-3,20-dione-16-17-acetal-21 esters, process for their preparation, compositions, and methods for the treatment of inflammatory conditions
RU2194053C2 (ru)	2002-12-10	Производные андростена, фармацевтическая композиция
JP5097129B2 (ja)	2012-12-12	新規１１β−ヒドロキシアンドロスタ−４−エン−３−オン
JPS6140648B2 (ro)	1986-09-10
HU191539B (en)	1987-03-30	Process for producing new 6,16-dimethyl-corticoides and pharmaceutical compositions containing them
HU190746B (en)	1986-10-28	Process for producing 6-alpha-methyl-corticoides and pharmaceutical compositions containing them
US4243664A (en)	1981-01-06	Novel corticoids
US4777165A (en)	1988-10-11	6α, 16β-dimethyl corticoids and their anti-inflammatory use
JPS6131116B2 (ro)	1986-07-17
JPS6214557B2 (ro)	1987-04-02
SE447388B (sv)	1986-11-10	Nya diklorerade derivat av 16-alfa-metylpregnanserien, framstellning derav,anvendning derav som lekemedel och kompositioner innehallande dem
JPH0419238B2 (ro)	1992-03-30
GB1594852A (en)	1981-08-05	Derivatives of 9-chloroprednisolone
EP0149222A2 (de)	1985-07-24	Neue 6alpha, 16alpha-Dimethylkortikoide
IE45305B1 (en)	1982-07-28	New corticoids
GB1589585A (en)	1981-05-13	12a-halocorticoids
CS202593B2 (cs)	1981-01-30	Způsob výroby derivátů 9-fluorprednisolonu
DE2809732C2 (de)	1986-04-24	Derivate des 9-Fluorprednisolons, Verfahren zu ihrer Herstellung, und pharmazeutische Präparate, die diese Wirkstoffe enthalten
HU181970B (en)	1983-11-28	Process for preparing new derivatives of 9alpha-fluoro-prednisolone
CS199512B2 (cs)	1980-07-31	Způsob výroby kortikoidfi
JPH046200B2 (ro)	1992-02-05
CS244663B2 (cs)	1986-08-14	Způsob výroby nových derivátů 9-chlorprednisolonu
JPH0415800B2 (ro)	1992-03-19
CS244662B2 (cs)	1986-08-14	Způsob výroby nových derivátů 9-chlorprednisolonu
CS248728B2 (cs)	1987-02-12	Způsob výroby derivátů βα-methylkortikoidu

JPS6131116B2 - - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (2)

Family

ID=25771793

Family Applications (1)

Country Status (20)

Cited By (1)

Families Citing this family (2)

Family Cites Families (3)

Cited By (1)

Also Published As

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