FI78111C - Foerfarande foer framstaellning av terapeutiskt aktiva 3,20-dioxo-1,4-pregnadien-17 -ol 17-aromatisk- heterocykliska karboxylater. - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiva 3,20-dioxo-1,4-pregnadien-17 -ol 17-aromatisk- heterocykliska karboxylater. Download PDFInfo
- Publication number
- FI78111C FI78111C FI820280A FI820280A FI78111C FI 78111 C FI78111 C FI 78111C FI 820280 A FI820280 A FI 820280A FI 820280 A FI820280 A FI 820280A FI 78111 C FI78111 C FI 78111C
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- formula
- dione
- furoate
- pregnadiene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 32
- 230000008569 process Effects 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 90
- 239000000460 chlorine Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
- 239000011737 fluorine Substances 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 16
- 239000007858 starting material Substances 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 238000005886 esterification reaction Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 230000032050 esterification Effects 0.000 claims description 8
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 abstract description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 222
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 147
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 84
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 68
- 239000000047 product Substances 0.000 description 51
- 239000000243 solution Substances 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 238000001819 mass spectrum Methods 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- 238000012746 preparative thin layer chromatography Methods 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- -1 2,3-dimethyl-butyl Chemical group 0.000 description 25
- 239000012043 crude product Substances 0.000 description 25
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- 238000003756 stirring Methods 0.000 description 21
- 229950005792 tenoate Drugs 0.000 description 21
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 14
- 239000012153 distilled water Substances 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- 150000002500 ions Chemical class 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000012264 purified product Substances 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 230000003110 anti-inflammatory effect Effects 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000284 extract Substances 0.000 description 7
- 238000007429 general method Methods 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 229950010765 pivalate Drugs 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000005658 halogenation reaction Methods 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 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 3
- 150000003431 steroids Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000002260 anti-inflammatory agent 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
- SNHRLVCMMWUAJD-SUYDQAKGSA-N betamethasone valerate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O SNHRLVCMMWUAJD-SUYDQAKGSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- KCENQZYGMHVBJH-UHFFFAOYSA-N furan-2-carbonyl furan-2-carboxylate Chemical compound C=1C=COC=1C(=O)OC(=O)C1=CC=CO1 KCENQZYGMHVBJH-UHFFFAOYSA-N 0.000 description 2
- BTUIFMCWPFMNRG-UHFFFAOYSA-N furan-3-carbonyl chloride Chemical compound ClC(=O)C=1C=COC=1 BTUIFMCWPFMNRG-UHFFFAOYSA-N 0.000 description 2
- 230000008570 general process Effects 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- 229940091173 hydantoin Drugs 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000004237 preparative chromatography Methods 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000012265 solid product Substances 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- NRQHBNNTBIDSRK-YRNVUSSQSA-N (4e)-4-[(4-methoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one Chemical compound C1=CC(OC)=CC=C1\C=C\1C(=O)OC(C)=N/1 NRQHBNNTBIDSRK-YRNVUSSQSA-N 0.000 description 1
- OKUWFSWDZQMETE-LEKSSAKUSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-10,13-dimethyl-8,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Chemical class C1=CC2=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 OKUWFSWDZQMETE-LEKSSAKUSA-N 0.000 description 1
- NBLHTECOWAHOPA-LVUPHWHUSA-N (9r,10s,13s)-17-acetyl-10,13-dimethyl-1,2,4,5,6,9,11,12-octahydrocyclopenta[a]phenanthren-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@@H](CC[C@@]3(C(C(=O)C)=CC=C33)C)C3=CCC21 NBLHTECOWAHOPA-LVUPHWHUSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- ILAOVOOZLVGAJF-UHFFFAOYSA-N 1-methylpyrrole-2-carboxylic acid Chemical compound CN1C=CC=C1C(O)=O ILAOVOOZLVGAJF-UHFFFAOYSA-N 0.000 description 1
- MWCJSNMDXGOJFD-UHFFFAOYSA-N 2,3-dihydrofuran-2-carboxylic acid Chemical compound OC(=O)C1CC=CO1 MWCJSNMDXGOJFD-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
- YVTQHZDUDUCGRD-UHFFFAOYSA-N 5-bromofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)O1 YVTQHZDUDUCGRD-UHFFFAOYSA-N 0.000 description 1
- DJCGIWVUKCNCAT-UHFFFAOYSA-N 5-methylthiophene-2-carbonyl chloride Chemical compound CC1=CC=C(C(Cl)=O)S1 DJCGIWVUKCNCAT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FPVRUILUEYSIMD-RPRRAYFGSA-N [(8s,9r,10s,11s,13s,14s,16r,17r)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(OC(C)=O)[C@@]1(C)C[C@@H]2O FPVRUILUEYSIMD-RPRRAYFGSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines 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
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960002537 betamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
- SOQJPQZCPBDOMF-YCUXZELOSA-N betamethasone benzoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(F)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@@H]1C)C(=O)CO)C(=O)C1=CC=CC=C1 SOQJPQZCPBDOMF-YCUXZELOSA-N 0.000 description 1
- 229960000870 betamethasone benzoate Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- 238000011097 chromatography purification 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
- 239000000470 constituent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229940117173 croton oil Drugs 0.000 description 1
- 229960003657 dexamethasone acetate Drugs 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- CNTIXUGILVWVHR-UHFFFAOYSA-N diphosphoryl chloride Chemical compound ClP(Cl)(=O)OP(Cl)(Cl)=O CNTIXUGILVWVHR-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000002092 orthoester group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- GLBUZFYJIIWCFB-UHFFFAOYSA-N propanethioyl chloride Chemical compound CCC(Cl)=S GLBUZFYJIIWCFB-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 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
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229940005605 valeric acid Drugs 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J33/002—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23076381A | 1981-02-02 | 1981-02-02 | |
| US23076381 | 1981-02-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI820280L FI820280L (fi) | 1982-08-03 |
| FI78111B FI78111B (fi) | 1989-02-28 |
| FI78111C true FI78111C (fi) | 1989-06-12 |
Family
ID=22866476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI820280A FI78111C (fi) | 1981-02-02 | 1982-01-28 | Foerfarande foer framstaellning av terapeutiskt aktiva 3,20-dioxo-1,4-pregnadien-17 -ol 17-aromatisk- heterocykliska karboxylater. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4472393A (OSRAM) |
| EP (1) | EP0057401B1 (OSRAM) |
| JP (1) | JPS57146800A (OSRAM) |
| KR (1) | KR890000761B1 (OSRAM) |
| AT (1) | ATE8790T1 (OSRAM) |
| AU (1) | AU549102B2 (OSRAM) |
| BG (1) | BG60799B2 (OSRAM) |
| CA (1) | CA1177822A (OSRAM) |
| CY (1) | CY1359A (OSRAM) |
| DE (1) | DE3260474D1 (OSRAM) |
| DK (1) | DK162770C (OSRAM) |
| FI (1) | FI78111C (OSRAM) |
| HK (1) | HK68487A (OSRAM) |
| HU (1) | HU188769B (OSRAM) |
| IE (1) | IE52576B1 (OSRAM) |
| IL (1) | IL64885A (OSRAM) |
| KE (1) | KE3694A (OSRAM) |
| MX (1) | MX9203403A (OSRAM) |
| NL (1) | NL930095I2 (OSRAM) |
| NO (2) | NO157020C (OSRAM) |
| NZ (1) | NZ199600A (OSRAM) |
| OA (1) | OA07116A (OSRAM) |
| PH (1) | PH19733A (OSRAM) |
| PT (1) | PT74357B (OSRAM) |
| ZA (1) | ZA82566B (OSRAM) |
Families Citing this family (120)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5446177A (en) * | 1984-12-28 | 1995-08-29 | Alcon Laboratories, Inc. | Anti-inflammatory compounds for ophthalmic use |
| US4686214A (en) * | 1985-10-30 | 1987-08-11 | Alcon Laboratories, Inc. | Anti-inflammatory compounds for ophthalmic use |
| US4914090A (en) * | 1985-11-01 | 1990-04-03 | Schering Corporation | Ophthalmic compositions |
| IL79661A (en) * | 1986-08-08 | 1991-01-31 | Yeda Res & Dev | Antiviral composition containing hypericin or pseudohypericin |
| US4808610A (en) * | 1986-10-02 | 1989-02-28 | Schering Corporation | Mometasone furoate anti-inflammatory cream composition using hexylene glycol |
| US4775529A (en) * | 1987-05-21 | 1988-10-04 | Schering Corporation | Steroid lotion |
| US6536427B2 (en) | 1990-03-02 | 2003-03-25 | Glaxo Group Limited | Inhalation device |
| HU213221B (en) | 1990-03-02 | 1997-03-28 | Glaxo Group Ltd | Inhalation device and medicine packet for device |
| UA26230A (uk) * | 1990-03-02 | 1999-07-19 | Глексо Груп Лімітед | Іhгалятор для спільhого використаhhя з лікувальhим блоком і лікувальhий блок |
| CA2091360C (en) | 1990-09-10 | 1997-04-08 | Pui-Ho Yuen | Mometasone furoate monohydrate, process for making same and pharmaceutical compositions |
| ATE226067T1 (de) | 1991-06-10 | 2002-11-15 | Schering Corp | Fluorchlorkohlenwasserstofffreie aerosolformulierungen |
| JP3323199B2 (ja) † | 1991-06-10 | 2002-09-09 | シェリング・コーポレーション | クロロフルオロカーボン不含エアゾール製剤 |
| US6127353A (en) * | 1991-09-06 | 2000-10-03 | Schering Corporation | Mometasone furoate monohydrate, process for making same and pharmaceutical compositions |
| US5420120A (en) * | 1993-12-17 | 1995-05-30 | Alcon Laboratories, Inc. | Anti-inflammatory glucocorticoid compounds for topical ophthalmic use |
| KR100361240B1 (ko) * | 1993-12-21 | 2003-01-29 | 쉐링 코포레이션 | 건선치료용약제학적조성물 |
| US5837699A (en) | 1994-01-27 | 1998-11-17 | Schering Corporation | Use of mometasone furoate for treating upper airway passage diseases |
| PE44995A1 (es) | 1994-01-27 | 1995-12-18 | Schering Corp | Furoato de mometasona para el tratamiento de las enfermedades pulmonares y de las vias respiratorias |
| US5502076A (en) * | 1994-03-08 | 1996-03-26 | Hoffmann-La Roche Inc. | Dispersing agents for use with hydrofluoroalkane propellants |
| DE4433374A1 (de) * | 1994-09-20 | 1996-03-21 | Hoechst Ag | 17-Desoxi-corticosteroid-21-/O/-Carbonsäure- ester, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| US5696105A (en) * | 1996-03-14 | 1997-12-09 | Hackler; Walter A. | Antifungal nail composition |
| CN1158296C (zh) * | 1996-06-28 | 2004-07-21 | 先灵公司 | 9α,21-二卤代-孕甾烷-11β,17α-二醇-20-酮的17-酯的制备方法 |
| US5886200A (en) * | 1996-07-01 | 1999-03-23 | Schering Corporation | Process for the preparation of 17-esters of 9 α, 21-dihalo-pregnane-11 β, 17 α-diol-20-ones |
| US6495167B2 (en) | 1997-03-20 | 2002-12-17 | Schering Corporation | Preparation of powder agglomerates |
| US6503537B2 (en) | 1997-03-20 | 2003-01-07 | Schering Corporation | Preparation of powder agglomerates |
| US6297227B1 (en) | 1998-09-10 | 2001-10-02 | Schering Corporation | Methods and compositions for treating sinusitis, otitis media and other related disorders using antihistamines |
| US8722668B2 (en) * | 1998-12-23 | 2014-05-13 | Daryl W. Hochman | Methods and compositions for the treatment of neuropathic pain and neuropsychiatric disorders |
| PT102343B (pt) * | 1999-08-02 | 2003-11-28 | Hovione Farmaciencia Sa | Processo para a preparacao de furoato mometasona |
| PT102405A (pt) * | 2000-01-20 | 2001-07-31 | Hovione Farmaciencia Sa | Processo para a preparacao de mometasona |
| GB0009612D0 (en) * | 2000-04-18 | 2000-06-07 | Glaxo Group Ltd | Therapeutic formulations |
| GB0009605D0 (en) * | 2000-04-18 | 2000-06-07 | Glaxo Group Ltd | Medicaments |
| GB0009609D0 (en) * | 2000-04-18 | 2000-06-07 | Glaxo Group Ltd | Therapeutic compositions |
| GB0015876D0 (en) * | 2000-06-28 | 2000-08-23 | Novartis Ag | Organic compounds |
| CA2417973A1 (en) * | 2000-08-04 | 2002-02-14 | Longwood Pharmaceutical Research, Inc. | Formulations of mometasone and a bronchodilator for pulmonary administration |
| US6787532B2 (en) | 2000-08-05 | 2004-09-07 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivatives |
| GB0019172D0 (en) | 2000-08-05 | 2000-09-27 | Glaxo Group Ltd | Novel compounds |
| US6858593B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| AU7576001A (en) † | 2000-08-05 | 2002-02-18 | Glaxo Group Ltd | 6.alpha., 9.alpha.-difluoro-17.alpha.-`(2-furanylcarboxyl) oxy]-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androst-1,4,-diene-17-carbothioic acid s-fluoromethyl ester as an anti-inflammatory agent |
| US6759398B2 (en) | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| US6777399B2 (en) * | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6750210B2 (en) | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
| US6858596B2 (en) * | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| US6777400B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| UA77656C2 (en) | 2001-04-07 | 2007-01-15 | Glaxo Group Ltd | S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent |
| DK1383786T3 (da) | 2001-04-30 | 2009-01-12 | Glaxo Group Ltd | Antiinflammatoriske 17-beta-carbothioatesterderivater af androstan med en cyklisk estergruppe i 17alfa-stilling |
| ES2307751T3 (es) * | 2001-06-12 | 2008-12-01 | Glaxo Group Limited | Nuevos esteres heterociclicos centi-inflamatorios 17 alfa de derivados 17 beta de carbotioato de androstano. |
| GB0125259D0 (en) | 2001-10-20 | 2001-12-12 | Glaxo Group Ltd | Novel compounds |
| GB0127160D0 (en) * | 2001-11-12 | 2002-01-02 | Glaxo Group Ltd | Novel compounds |
| WO2003042229A1 (en) * | 2001-11-12 | 2003-05-22 | Glaxo Group Limited | Non-aromatic heterocyclic esters of furan-2-one-esters of 17.beta.-carboxyl or 17.beta.-carbothio glucocorticoids |
| ITMI20020148A1 (it) * | 2002-01-29 | 2003-07-29 | Nicox Sa | Nuovi corticosteroidi |
| US20050175545A1 (en) * | 2002-02-04 | 2005-08-11 | Keith Biggadike | Formulation for inhalation comprising a glucocorticoid and a beta 2-adrenoreceptor agonist |
| GB0202635D0 (en) * | 2002-02-05 | 2002-03-20 | Glaxo Wellcome Mfg Pte Ltd | Formulation containing novel anti-inflammatory androstane derivative |
| GB0207906D0 (en) | 2002-04-05 | 2002-05-15 | 3M Innovative Properties Co | Formoterol and mometasone aerosol formulations |
| GB2389530B (en) | 2002-06-14 | 2007-01-10 | Cipla Ltd | Pharmaceutical compositions |
| CA2522666A1 (en) * | 2003-04-18 | 2004-10-28 | Pharmacia & Upjohn Company Llc | Combination therapies for chronic obstructive pulmonary disease (copd) |
| EP1663999A2 (en) * | 2003-08-29 | 2006-06-07 | Ranbaxy Laboratories, Ltd. | Inhibitors of phosphodiesterase type-iv |
| US20070259874A1 (en) * | 2003-11-26 | 2007-11-08 | Palle Venkata P | Phosphodiesterase Inhibitors |
| JP4976139B2 (ja) * | 2004-01-21 | 2012-07-18 | シェーリング コーポレイション | 処置方法 |
| US20080009535A1 (en) * | 2004-08-30 | 2008-01-10 | Sarala Balachandran | Inhibitors of phosphodiesterase type-IV |
| US20060211667A1 (en) * | 2005-03-21 | 2006-09-21 | Eric Marchewitz | Use of pregnane steroid derivatives for enhancing physical performance |
| GB0507165D0 (en) * | 2005-04-08 | 2005-05-18 | Glaxo Group Ltd | Novel crystalline pharmaceutical product |
| ES2265276B1 (es) | 2005-05-20 | 2008-02-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
| GB0523653D0 (en) * | 2005-11-21 | 2005-12-28 | Novartis Ag | Organic compounds |
| US20070099883A1 (en) * | 2005-10-07 | 2007-05-03 | Cheryl Lynn Calis | Anhydrous mometasone furoate formulation |
| RU2008119322A (ru) * | 2005-10-19 | 2009-11-27 | Рэнбакси Лабораториз Лимитед (In) | Композиции ингибиторов фосфодиэстеразы iv типа |
| US20090221664A1 (en) | 2005-10-19 | 2009-09-03 | Abhijit Ray | Pharmaceutical compositions of muscarinic receptor antagonists |
| CN100389121C (zh) * | 2005-12-09 | 2008-05-21 | 天津药业集团有限公司 | 糠酸莫美他松中间体21-羟的制备方法 |
| CN100436473C (zh) * | 2005-12-09 | 2008-11-26 | 天津药业集团有限公司 | 糠酸莫美他松中间体21-酯及制法 |
| AR059216A1 (es) * | 2006-01-27 | 2008-03-19 | Sun Pharmaceutical Ind Ltd | 11b-hidroxiandrosta-4-eno-3-onas |
| GB0615108D0 (en) * | 2006-07-28 | 2006-09-06 | Glaxo Group Ltd | Novel formulations |
| EP2086948A2 (en) * | 2006-09-22 | 2009-08-12 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type-iv |
| EP2066661A2 (en) * | 2006-09-22 | 2009-06-10 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
| EP2083798A1 (en) * | 2006-10-19 | 2009-08-05 | Cipla Limited | Pharmaceutical compositions and nasal spray incorporating anhydrous mometasone furoate |
| EP1958947A1 (en) | 2007-02-15 | 2008-08-20 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type 4 |
| EP2124943A1 (en) * | 2007-03-14 | 2009-12-02 | Ranbaxy Laboratories Limited | Pyrazolo [3, 4-b]pyridine derivatives as phosphodiesterase inhibitors |
| CA2680625C (en) * | 2007-03-14 | 2016-02-23 | Ranbaxy Laboratories Limited | Pyrazolo (3, 4-b) pyridine derivatives as phosphodiesterase inhibitors |
| EP2120868A4 (en) * | 2007-04-11 | 2010-08-25 | Perrigo Israel Phamaceuticals | LOW-DOSED MOMETASON FORMULATIONS |
| WO2009063493A2 (en) * | 2007-09-10 | 2009-05-22 | Glenmark Pharmaceuticals Limited | Topical pharmaceutical composition for the combination of fusidic acid and a corticosteroid |
| US20090082318A1 (en) * | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched mometasone |
| WO2009045539A2 (en) * | 2007-10-05 | 2009-04-09 | Nektar Therapeutics Al, Corporation | Oligomer-corticosteroid conjugates |
| EP2111861A1 (en) | 2008-04-21 | 2009-10-28 | Ranbaxy Laboratories Limited | Compositions of phosphodiesterase type IV inhibitors |
| PT2805720T (pt) | 2008-05-28 | 2019-09-23 | Reveragen Biopharma Inc | Moduladores esteroides não hormonais de nf-kb para tratamento de uma doença |
| UY32297A (es) | 2008-12-22 | 2010-05-31 | Almirall Sa | Sal mesilato de 5-(2-{[6-(2,2-difluoro-2-fenilitoxi) hexil]amino}-1-hidroxietil)-8-hidroxiquinolin-2( 1h)-ona como agonista del receptor b(beta)2 acrenérgico |
| EP2228368A1 (en) | 2009-03-12 | 2010-09-15 | Almirall, S.A. | Process for manufacturing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one |
| AR076807A1 (es) * | 2009-05-29 | 2011-07-06 | Pearl Therapeutics Inc | Composiciones metodos y sistemas para el suministro de dos o mas agentes activos mediante las vias respiratorias. metodo de preparacion composicion |
| US8815258B2 (en) | 2009-05-29 | 2014-08-26 | Pearl Therapeutics, Inc. | Compositions, methods and systems for respiratory delivery of two or more active agents |
| PL2482822T3 (pl) | 2009-10-01 | 2018-10-31 | Adare Pharmaceuticals, Inc. | Podawane doustnie kompozycje kortykosteroidowe |
| WO2011093810A2 (en) | 2010-01-28 | 2011-08-04 | Bilgic Mahmut | Dry powder pharmaceutical composition comprising tiotropium and mometasone |
| EP2533765A2 (en) | 2010-01-29 | 2012-12-19 | Mahmut Bilgic | Pharmaceutical compositions comprising formoterol and mometasone |
| EP2556083A4 (en) | 2010-04-05 | 2013-12-04 | Validus Biopharma Inc | NONHORMONAL STEROID MODULATORS OF NF-KAPPA-B FOR DISEASE TREATMENT |
| WO2011136754A1 (en) | 2010-04-26 | 2011-11-03 | Mahmut Bilgic | A medicament developed for the treatment of respiratory diseases |
| JOP20120023B1 (ar) | 2011-02-04 | 2022-03-14 | Novartis Ag | صياغات مساحيق جافة من جسيمات تحتوي على واحد أو اثنين من المواد الفعالة لعلاج امراض ممرات الهواء الانسدادية او الالتهابية |
| EP2578570A1 (en) | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
| WO2013109207A1 (en) | 2012-01-16 | 2013-07-25 | Mahmut Bilgic | Dry powder formulations comprising mometasone |
| EP2641900A1 (en) | 2012-03-20 | 2013-09-25 | Almirall, S.A. | Novel polymorphic Crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one, heminapadisylate as agonist of the ß2 adrenergic receptor. |
| US20150224197A1 (en) | 2012-07-05 | 2015-08-13 | Arven Ilac Sanayi Ve Ticaret A.S. | Inhalation compositions |
| WO2014007771A2 (en) | 2012-07-05 | 2014-01-09 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Inhalation compositions comprising muscarinic receptor antagonist |
| WO2014007772A2 (en) | 2012-07-05 | 2014-01-09 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Inhalation compositions comprising glucose anhydrous |
| US20150165037A1 (en) | 2012-07-05 | 2015-06-18 | Arven llac Sanayi Ve Ticaret A.S. | Inhalation compositions comprising corticosteroid and sorbitol |
| US9452139B2 (en) | 2013-03-14 | 2016-09-27 | Novartis Ag | Respirable agglomerates of porous carrier particles and micronized drug |
| WO2014141069A1 (en) | 2013-03-14 | 2014-09-18 | Novartis Ag | Deamorphization of spray-dried formulations via spray-blending |
| CA2905542C (en) | 2013-03-15 | 2022-05-03 | Pearl Therapeutics, Inc. | Methods and systems for conditioning of particulate crystalline materials |
| RU2015154720A (ru) | 2013-05-22 | 2017-06-27 | Перл Терапьютикс, Инк. | Композиции, способы и системы для респираторной доставки трех или более активных средств |
| WO2015034678A2 (en) | 2013-09-06 | 2015-03-12 | Aptalis Pharmatech, Inc. | Corticosteroid containing orally disintegrating tablet compositions for eosinophilic esophagitis |
| JP2017508776A (ja) | 2014-03-27 | 2017-03-30 | ノバルティス アーゲー | 医薬品有効成分吸入用の噴霧乾燥した水中油中固体分散体 |
| EP3006453A1 (en) | 2014-10-08 | 2016-04-13 | Cosmo Technologies Ltd. | 17alpha-monoesters and 17alpha,21-diesters of cortexolone for use in the treatment of tumors |
| WO2017004205A1 (en) | 2015-06-29 | 2017-01-05 | Reveragen Biopharma, Inc. | NON-HORMONAL STEROID MODULATORS OF NF-κB FOR TREATMENT OF DISEASE |
| CN105481933B (zh) * | 2015-12-25 | 2017-09-19 | 山东京卫制药有限公司 | 一种合成糠酸莫米松的方法 |
| CN107266519B (zh) * | 2016-04-08 | 2021-06-29 | 天津金耀集团有限公司 | 一种9β，11β-环氧-17α-羟基-16α-甲基-21-氯代-1，4孕甾二烯-3，20-二酮新晶型及其制备方法 |
| CN107266518B (zh) * | 2016-04-08 | 2021-03-30 | 天津金耀集团有限公司 | 一种糠酸莫米松晶型及其制备方法 |
| TWI777515B (zh) | 2016-08-18 | 2022-09-11 | 美商愛戴爾製藥股份有限公司 | 治療嗜伊紅性食道炎之方法 |
| CN107793462A (zh) * | 2016-08-30 | 2018-03-13 | 天津太平洋制药有限公司 | 一种丙酸氯倍他索的制备方法 |
| CN107778341A (zh) * | 2016-08-30 | 2018-03-09 | 天津太平洋制药有限公司 | 一种哈西奈德的制备方法 |
| CN109206468B (zh) * | 2017-06-30 | 2023-06-27 | 天津药业研究院股份有限公司 | 一种糠酸莫米松的制备方法 |
| CN109206466B (zh) * | 2017-06-30 | 2022-08-09 | 天津药业研究院股份有限公司 | 一种甾体21位羟基氯代或溴代方法 |
| CN107573398B (zh) * | 2017-09-07 | 2021-02-26 | 山东泰华生物科技股份有限公司 | 一种哈西奈德及其衍生物的制备方法 |
| CN108395465B (zh) * | 2018-05-10 | 2019-07-30 | 浙江仙居仙乐药业有限公司 | 一种地塞米松环氧水解物的合成方法 |
| US11382922B2 (en) | 2019-03-07 | 2022-07-12 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
| KR20240042437A (ko) | 2021-07-09 | 2024-04-02 | 아스트라제네카 파마수티컬스 엘피 | 에어로졸 약물 전달을 위한 조성물, 방법 및 시스템 |
| JP2024545816A (ja) | 2021-12-20 | 2024-12-12 | アストラゼネカ・アクチエボラーグ | エアロゾル薬物送達のための組成物、方法及びシステム |
| EP4566595A1 (en) | 2023-12-07 | 2025-06-11 | Bernhard Roth | Combination preparation for the treatment of acute and chronic rhinosinusitis |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1059906B (de) * | 1954-10-05 | 1959-06-25 | Scherico Ltd | Verfahren zur Herstellung von 1, 4-Pregnadienen |
| US3557158A (en) * | 1962-01-22 | 1971-01-19 | Upjohn Co | 6alpha-fluoro-16-methyl - 4 - pregnene 3,20-diones and intermediates produced in the synthesis thereof |
| US3422193A (en) * | 1966-08-11 | 1969-01-14 | Schering Corp | 17-mono esters of corticoids |
| IT1061787B (it) * | 1967-03-01 | 1983-04-30 | Vismara Francesco Spa | Miglioramenti relativi alla preparazione di 17 benzoato di betametazone |
| US3784692A (en) * | 1967-06-16 | 1974-01-08 | Warner Lambert Co | 17-propionate,21-ester derivatives of 6alpha,9alpha-difluoroprednisolone,compositions and use |
| GB1253831A (en) * | 1968-01-19 | 1971-11-17 | Glaxo Lab Ltd | 9alpha,21-DIHALOPREGNANE COMPOUNDS |
| US3980778A (en) * | 1973-10-25 | 1976-09-14 | The Upjohn Company | Anti-inflammatory steroid |
| NL7502252A (nl) * | 1974-02-27 | 1975-08-29 | Pierrel Spa | Werkwijze voor het bereiden van een geneesmid- del met anti-inflammatoire werking, gevormd ge- neesmiddel verkregen volgens deze werkwijze alsmede werkwijze voor het bereiden van in het geneesmiddel gebruikte nieuwe steroiden. |
| GB1505701A (en) * | 1975-06-14 | 1978-03-30 | Pierrel Spa | 2-chloro-6beta-fluoropregnanes |
| US4221787A (en) * | 1978-03-28 | 1980-09-09 | Interx Research Corporation | Esteramide prodrugs of anti-inflammatory corticosteroids |
-
1982
- 1982-01-25 AT AT82100490T patent/ATE8790T1/de active
- 1982-01-25 DE DE8282100490T patent/DE3260474D1/de not_active Expired
- 1982-01-25 CY CY135982A patent/CY1359A/xx unknown
- 1982-01-25 EP EP82100490A patent/EP0057401B1/en not_active Expired
- 1982-01-28 NO NO820263A patent/NO157020C/no not_active IP Right Cessation
- 1982-01-28 ZA ZA82566A patent/ZA82566B/xx unknown
- 1982-01-28 IL IL64885A patent/IL64885A/xx unknown
- 1982-01-28 NZ NZ199600A patent/NZ199600A/en unknown
- 1982-01-28 AU AU79918/82A patent/AU549102B2/en not_active Expired
- 1982-01-28 DK DK039082A patent/DK162770C/da not_active IP Right Cessation
- 1982-01-28 FI FI820280A patent/FI78111C/fi not_active IP Right Cessation
- 1982-01-29 JP JP57013191A patent/JPS57146800A/ja active Granted
- 1982-01-29 PH PH26804A patent/PH19733A/en unknown
- 1982-01-29 IE IE207/82A patent/IE52576B1/en not_active IP Right Cessation
- 1982-01-29 KR KR8200374A patent/KR890000761B1/ko not_active Expired
- 1982-01-29 PT PT74357A patent/PT74357B/pt unknown
- 1982-01-29 CA CA000395237A patent/CA1177822A/en not_active Expired
- 1982-02-01 HU HU82295A patent/HU188769B/hu unknown
- 1982-06-03 OA OA57705A patent/OA07116A/xx unknown
- 1982-07-29 US US06/403,276 patent/US4472393A/en not_active Expired - Lifetime
-
1987
- 1987-02-19 KE KE3694A patent/KE3694A/xx unknown
- 1987-09-24 HK HK684/87A patent/HK68487A/en not_active IP Right Cessation
-
1992
- 1992-06-25 MX MX9203403A patent/MX9203403A/es active IP Right Grant
-
1993
- 1993-06-24 NL NL930095C patent/NL930095I2/nl unknown
-
1994
- 1994-02-24 BG BG098562A patent/BG60799B2/bg unknown
- 1994-10-07 NO NO1994018C patent/NO1994018I1/no unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI78111C (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva 3,20-dioxo-1,4-pregnadien-17 -ol 17-aromatisk- heterocykliska karboxylater. | |
| US4242334A (en) | Corticoid 17-(alkyl carbonates) and processes for their preparation | |
| US4124707A (en) | 7α-Halogeno-3,20-dioxo-1,4-pregnadienes, methods for their manufacture, their use as anti-inflammatory agents, and pharmaceutical formulations useful therefor | |
| US4377575A (en) | Corticoid-17-(alkyl carbonates) and process for their manufacture | |
| FI80888C (fi) | Foerfarande foer framstaellning av terapeutiskt verkande steroida karboxylsyraestrar. | |
| EP0902789B1 (en) | Androstene derivatives | |
| US4267173A (en) | Use of 6β-fluoro-7α-halogenocorticoids as topical anti-inflammatories and pharmaceutical formulations useful therefor | |
| US4076708A (en) | Process for the preparation of 7α-halogeno-3-oxo-4-dehydro steroids and novel 7α-halogeno derivatives produced thereby | |
| IE53753B1 (en) | Novel 6a-methylprednisolone derivatives and their manufacture and use | |
| US4336200A (en) | 17α-Acyloxy-5β-corticoids | |
| EP0061416B1 (en) | Process for the preparation of delta 9(11)- and delta 16-21-chloro-20-keto steroids of the pregnane and d-homopregnane series and their use as intermediates for the synthesis of highly effective corticoids | |
| CA1155108A (en) | 17.alpha.-ACYLOXY-5.beta. AND 5.alpha. CORTICOIDS | |
| DK142201B (da) | Analogifremgangsmåde til fremstilling af retinoater af 4-pregnen-3,20-dioner eller af 1,4-pregnadien-3,20-dioner. | |
| US4929395A (en) | 16α-methylation process | |
| IE56281B1 (en) | Novel 6alpha-methylcorticoins and their manufacture and use | |
| EP0072546B1 (de) | Neue Hydrocortison-Derivate, ihre Herstellung und Verwendung | |
| EP0001864A1 (en) | Novel 6-oxygenated-3,20-dioxo-pregnane derivatives, process for the preparation thereof, and pharmaceutical compositions containing them | |
| US4990612A (en) | 16α-methylation process | |
| US4704455A (en) | 16α-methylatedΔ17(20)-corticoids | |
| NO773361L (no) | Fremgangsmaate ved fremstilling av corticoider | |
| US4427591A (en) | Reduced A ring-Δ9(11) -corticoids | |
| EP0136586B1 (en) | Novel corticoid derivatives and process for production thereof | |
| EP0165526B1 (en) | 17-(substituted thio) 17-(substituted dithio) androstenes | |
| US4602009A (en) | Corticoid derivatives and process for production thereof | |
| SK403491A3 (en) | Androstane carbothionates and pharmaceutical agents containing thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ND | Supplementary protection certificate (spc) granted | ||
| SPCG | Supplementary protection certificate granted |
Spc suppl protection certif: L19 Extension date: 20050622 |
|
| MA | Patent expired |
Owner name: SCHERING CORPORATION |