CA1100943A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1100943A
Authority: CA; Canada
Prior art keywords: alpha; dione; chloro; pregnadiene; delta
Prior art date: 1976-10-04
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

CA288,063A

Other languages

English (en)

Inventor

Klaus Annen

Henry Laurent

Helmut Hofmeister

Rudolf Wiechert

Hans Wendt

Joachim F. Kapp

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.)

1976-10-04

Filing date

1977-10-04

Publication date

1981-05-12

1977-10-04 Application filed by Schering AG filed Critical Schering AG

1981-05-12 Application granted granted Critical

1981-05-12 Publication of CA1100943A publication Critical patent/CA1100943A/fr

Status Expired legal-status Critical Current

Links

125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 14
125000004423 acyloxy group Chemical group 0.000 claims abstract description 11
229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims abstract description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
125000002252 acyl group Chemical group 0.000 claims abstract description 8
229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 87
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 66
239000000126 substance Substances 0.000 claims description 48
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 33
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 19
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 11
239000007864 aqueous solution Substances 0.000 claims description 11
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 8
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 8
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 claims description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 5
235000019253 formic acid Nutrition 0.000 claims 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 claims description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
CTIKAHQFRQTTAY-UHFFFAOYSA-N fluoro(trimethyl)silane Chemical compound C[Si](C)(C)F CTIKAHQFRQTTAY-UHFFFAOYSA-N 0.000 claims description 4
DAPZDAPTZFJZTO-UHFFFAOYSA-N heptanoyl heptanoate Chemical compound CCCCCCC(=O)OC(=O)CCCCCC DAPZDAPTZFJZTO-UHFFFAOYSA-N 0.000 claims description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
239000001632 sodium acetate Substances 0.000 claims description 4
235000017281 sodium acetate Nutrition 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
239000011737 fluorine Chemical group 0.000 claims description 3
ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 claims description 2
SOOHMJJPRAGGSQ-UHFFFAOYSA-N [fluoro(diphenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(F)C1=CC=CC=C1 SOOHMJJPRAGGSQ-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 claims description 2
150000002905 orthoesters Chemical class 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 64
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims 9
238000010992 reflux Methods 0.000 claims 3
239000000376 reactant Substances 0.000 claims 2
125000003700 epoxy group Chemical group 0.000 claims 1
230000000699 topical effect Effects 0.000 abstract description 5
230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
239000012043 crude product Substances 0.000 description 27
238000002844 melting Methods 0.000 description 27
230000008018 melting Effects 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 17
238000000354 decomposition reaction Methods 0.000 description 16
GUHFLRTWNHWJBS-VLTGGNAYSA-N (8r,9s,10s,13s)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1C1=CC=C(C(=O)C)[C@@]1(C)CC2 GUHFLRTWNHWJBS-VLTGGNAYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000013543 active substance Substances 0.000 description 7
239000005457 ice water Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
-1 valeric acld Chemical compound 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
241000700159 Rattus Species 0.000 description 5
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 5
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 4
241001465754 Metazoa Species 0.000 description 4
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
206010061218 Inflammation Diseases 0.000 description 3
206010030113 Oedema Diseases 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 3
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
230000004054 inflammatory process Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002674 ointment Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical group CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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 2
235000011054 acetic acid Nutrition 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
229960002903 benzyl benzoate Drugs 0.000 description 2
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 2
WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
210000005069 ears Anatomy 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
230000002401 inhibitory 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
239000006210 lotion Substances 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000001256 steam distillation Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
210000001541 thymus gland Anatomy 0.000 description 2
238000005303 weighing Methods 0.000 description 2
CPUKWYXYHPOQJH-RDQPJNLGSA-N (8r,9s,10s,13s,14s)-17-ethenyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(=CC4)C=C)[C@@H]4[C@@H]3CCC21 CPUKWYXYHPOQJH-RDQPJNLGSA-N 0.000 description 1
FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
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QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
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 1
201000004624 Dermatitis Diseases 0.000 description 1
206010012442 Dermatitis contact Diseases 0.000 description 1
206010012455 Dermatitis exfoliative Diseases 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
244000228957 Ferula foetida Species 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
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206010064000 Lichenoid keratosis Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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239000007795 chemical reaction product Substances 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
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238000001816 cooling Methods 0.000 description 1
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239000006071 cream Substances 0.000 description 1
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235000014113 dietary fatty acids Nutrition 0.000 description 1
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239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
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239000000194 fatty acid Substances 0.000 description 1
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MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000002085 irritant Substances 0.000 description 1
231100000021 irritant Toxicity 0.000 description 1
239000008101 lactose Substances 0.000 description 1
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229910052744 lithium Inorganic materials 0.000 description 1
IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical group [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
PXUQTDZNOHRWLI-OXUVVOBNSA-O malvidin 3-O-beta-D-glucoside Chemical compound COC1=C(O)C(OC)=CC(C=2C(=CC=3C(O)=CC(O)=CC=3[O+]=2)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C1 PXUQTDZNOHRWLI-OXUVVOBNSA-O 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229960002446 octanoic acid Drugs 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
201000004700 rosacea Diseases 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
150000008027 tertiary esters Chemical class 0.000 description 1
239000012085 test solution Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000003096 thymolvtic effect Effects 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1
210000002268 wool Anatomy 0.000 description 1

Classifications

- 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
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA288,063A 1976-10-04 1977-10-04 Traduction non-disponible Expired CA1100943A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2645105.8		1976-10-04
DE2645105A DE2645105C2 (de)	1976-10-04	1976-10-04	Derivate des 9-Chlorprednisolons, Verfahren zu ihrer Herstellung und diese enthaltendes pharmazeutisches Präparat

Publications (1)

Publication Number	Publication Date
CA1100943A true CA1100943A (fr)	1981-05-12

Family

ID=5989829

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA288,063A Expired CA1100943A (fr)	1976-10-04	1977-10-04	Traduction non-disponible

Country Status (9)

Country	Link
AU (1)	AU518954B2 (fr)
BE (1)	BE859345A (fr)
CA (1)	CA1100943A (fr)
DD (1)	DD132348A5 (fr)
DE (1)	DE2645105C2 (fr)
ES (3)	ES471733A1 (fr)
PL (1)	PL112152B1 (fr)
SU (1)	SU902668A3 (fr)
ZA (1)	ZA775914B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2932165A1 (de) *	1979-08-06	1981-02-26	Schering Ag	Neue derivate des 9-chlorprednisolons, ihre herstellung und verwendung
DE3227312A1 (de) *	1982-07-19	1984-01-19	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue 6,16-dimethylkortikoide, ihre herstellung und verwendung

1976
- 1976-10-04 DE DE2645105A patent/DE2645105C2/de not_active Expired
1977
- 1977-09-30 PL PL1977214009A patent/PL112152B1/pl unknown
- 1977-10-04 BE BE181431A patent/BE859345A/fr not_active IP Right Cessation
- 1977-10-04 DD DD7700201347A patent/DD132348A5/xx unknown
- 1977-10-04 CA CA288,063A patent/CA1100943A/fr not_active Expired
- 1977-10-04 AU AU29310/77A patent/AU518954B2/en not_active Expired
- 1977-10-04 ZA ZA00775914A patent/ZA775914B/xx unknown
1978
- 1978-07-14 ES ES471733A patent/ES471733A1/es not_active Expired
- 1978-07-14 ES ES471732A patent/ES471732A1/es not_active Expired
- 1978-07-14 ES ES471734A patent/ES471734A1/es not_active Expired
1979
- 1979-05-04 SU SU792764204A patent/SU902668A3/ru active

Also Published As

Publication number	Publication date
DD132348A5 (de)	1978-09-20
DE2645105C2 (de)	1986-03-13
DE2645105A1 (de)	1978-04-06
ZA775914B (en)	1978-05-30
AU518954B2 (en)	1981-10-29
BE859345A (fr)	1978-04-04
PL112152B1 (en)	1980-09-30
ES471733A1 (es)	1979-02-01
ES471732A1 (es)	1979-02-01
ES471734A1 (es)	1979-02-01
SU902668A3 (ru)	1982-01-30
AU2931077A (en)	1979-04-12

Legal Events

Date	Code	Title	Description
1998-05-12	MKEX	Expiry

Publication	Publication Date	Title
KR890000761B1 (ko)	1989-04-05	스테로이드의 방향성 헤테로사이클릭 에스테르 및 이의 제조방법
US4267173A (en)	1981-05-12	Use of 6β-fluoro-7α-halogenocorticoids as topical anti-inflammatories and pharmaceutical formulations useful therefor
US4910192A (en)	1990-03-20	Topically active steroidal anti-inflammatory agents
EP0029924B1 (fr)	1984-08-15	6-alpha-fluoro-16-méthyl-prednisolone-17,21-diesters et compositions pharmaceutiques les contenant
HU191539B (en)	1987-03-30	Process for producing new 6,16-dimethyl-corticoides and pharmaceutical compositions containing them
CA1100943A (fr)	1981-05-12	Traduction non-disponible
CA1251784A (fr)	1989-03-28	Steroides esterifies en position 17 et thioesterifies en position 21, methode de preparation et usage comme medicaments
CH644614A5 (de)	1984-08-15	17-alpha-acyloxy-5-beta- und 17-alpha-acyloxy-5-alpha-corticoide.
HU190746B (en)	1986-10-28	Process for producing 6-alpha-methyl-corticoides and pharmaceutical compositions containing them
CA1099255A (fr)	1981-04-14	Traduction non-disponible
IE45877B1 (en)	1982-12-15	New derivatives of 9-chloroprednisolone
CA1055483A (fr)	1979-05-29	DERIVES STEROIDIQUES DE TYPE 9,11.beta.-DIHALO (16A, 17B) 1,4-DIOXANE
JPS6252758B2 (fr)	1987-11-06
EP0149222A2 (fr)	1985-07-24	6-Alpha, 16 alpha-diméthylcorticoides
US4232013A (en)	1980-11-04	16,17-Pyrazolino- and 16,17-isopyrazolino-1,4-pregnadiene derivatives
CA1104124A (fr)	1981-06-30	Derives de 9-fluoroprednisolone
IE47729B1 (en)	1984-05-30	New steroids of the pregnane series substituted in the 17-position,and their manufacture and use
KR840000154B1 (ko)	1984-02-22	신규 6α-플루오로-프레드니솔론 17, 21-디에스테르의 제조방법
IE43979B1 (en)	1981-07-15	21-acetals and mixed acetals of steroidal 21-aldehydes,intermediates and methods of preparation
EP0000609B1 (fr)	1981-09-23	19-Nor pregnahexaènes, procédé pour leur préparation et compositions pharmaceutiques les contenant
CS244662B2 (cs)	1986-08-14	Způsob výroby nových derivátů 9-chlorprednisolonu
JPS6361000B2 (fr)	1988-11-28
CS244663B2 (cs)	1986-08-14	Způsob výroby nových derivátů 9-chlorprednisolonu
DE2809732A1 (de)	1979-09-13	Neue derivate des 9-fluorprednisolons
PL114012B1 (en)	1981-01-31	Process for preparing novel derivatives of 9-fluoroprednisolone