DD229702A5 - Verfahren zur herstellung von neuen corticoidderivaten - Google Patents

Verfahren zur herstellung von neuen corticoidderivaten Download PDF

Info

Publication number: DD229702A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; pregnadiene; fluoro; triol; iiβ
Prior art date: 1983-09-07

Application number

DD84275355A

Other languages

German (de)

English (en)

Inventor

Issei Nitta

Kenichiro Nakao

Motoyoshi Miyake

Akira Maruyama

Junko Takashima

Hiroaki Ueno

Original Assignee

Mitsubishi Chem Ind

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.)

1983-09-07

Filing date

1984-09-06

Publication date

1985-11-13

1983-09-07 Priority claimed from JP58164772A external-priority patent/JPS6056997A/ja

1984-06-12 Priority claimed from JP59120439A external-priority patent/JPS611698A/ja

1984-09-06 Application filed by Mitsubishi Chem Ind filed Critical Mitsubishi Chem Ind

1985-11-13 Publication of DD229702A5 publication Critical patent/DD229702A5/de

Links

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 title claims abstract description 11
238000000034 method Methods 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 10
125000004043 oxo group Chemical group O=* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims 4
230000003110 anti-inflammatory effect Effects 0.000 abstract description 11
230000000699 topical effect Effects 0.000 abstract description 10
230000009885 systemic effect Effects 0.000 abstract description 4
201000004624 Dermatitis Diseases 0.000 abstract description 3
206010012438 Dermatitis atopic Diseases 0.000 abstract description 2
206010012442 Dermatitis contact Diseases 0.000 abstract description 2
201000004681 Psoriasis Diseases 0.000 abstract description 2
230000001154 acute effect Effects 0.000 abstract description 2
208000006673 asthma Diseases 0.000 abstract description 2
201000008937 atopic dermatitis Diseases 0.000 abstract description 2
208000010247 contact dermatitis Diseases 0.000 abstract description 2
208000014617 hemorrhoid Diseases 0.000 abstract description 2
208000003265 stomatitis Diseases 0.000 abstract description 2
208000001319 vasomotor rhinitis Diseases 0.000 abstract description 2
206010067484 Adverse reaction Diseases 0.000 abstract 1
208000032041 Hearing impaired Diseases 0.000 abstract 1
208000022873 Ocular disease Diseases 0.000 abstract 1
206010039085 Rhinitis allergic Diseases 0.000 abstract 1
230000006838 adverse reaction Effects 0.000 abstract 1
201000010105 allergic rhinitis Diseases 0.000 abstract 1
208000010668 atopic eczema Diseases 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
239000000203 mixture Substances 0.000 description 55
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 38
JDRMYOQETPMYQX-UHFFFAOYSA-N monomethyl succinate Chemical compound COC(=O)CCC(O)=O JDRMYOQETPMYQX-UHFFFAOYSA-N 0.000 description 37
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
239000011541 reaction mixture Substances 0.000 description 35
239000002904 solvent Substances 0.000 description 28
238000004821 distillation Methods 0.000 description 27
239000000243 solution Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 18
230000008018 melting Effects 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
239000000741 silica gel Substances 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
150000001875 compounds Chemical class 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 12
238000001035 drying Methods 0.000 description 12
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
239000007787 solid Substances 0.000 description 10
238000005406 washing Methods 0.000 description 10
238000004440 column chromatography Methods 0.000 description 9
238000002329 infrared spectrum Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
239000005457 ice water Substances 0.000 description 8
239000000463 material Substances 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 7
230000000694 effects Effects 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
241000700159 Rattus Species 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
238000002356 laser light scattering Methods 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
LOLKAJARZKDJTD-UHFFFAOYSA-N 4-Ethoxy-4-oxobutanoic acid Chemical compound CCOC(=O)CCC(O)=O LOLKAJARZKDJTD-UHFFFAOYSA-N 0.000 description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
230000003096 thymolvtic effect Effects 0.000 description 5
-1 0.25 mm Chemical compound 0.000 description 4
CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate 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)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 description 4
229960004703 clobetasol propionate Drugs 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000007788 liquid Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
239000012359 Methanesulfonyl chloride Substances 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
206010030113 Oedema Diseases 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000012266 salt solution Substances 0.000 description 3
210000001541 thymus gland Anatomy 0.000 description 3
206010002091 Anaesthesia Diseases 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
230000037005 anaesthesia Effects 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229940117173 croton oil Drugs 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000002609 medium Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 description 1
VNDPUMWYEFWECV-UHFFFAOYSA-N 2-ethoxycarbonylbutanoic acid Chemical compound CCOC(=O)C(CC)C(O)=O VNDPUMWYEFWECV-UHFFFAOYSA-N 0.000 description 1
FIFFSYNZMURJCH-UHFFFAOYSA-N 2-methoxycarbonylbutanoic acid Chemical compound CCC(C(O)=O)C(=O)OC FIFFSYNZMURJCH-UHFFFAOYSA-N 0.000 description 1
BFGWFADODZRUMH-UHFFFAOYSA-N 2-methyl-3-oxoprop-2-enoic acid Chemical compound O=C=C(C)C(O)=O BFGWFADODZRUMH-UHFFFAOYSA-N 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
206010003694 Atrophy Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920001651 Cyanoacrylate Polymers 0.000 description 1
241000792859 Enema Species 0.000 description 1
208000016621 Hearing disease Diseases 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
241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
206010036775 Rectal inflammations Diseases 0.000 description 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
206010047513 Vision blurred Diseases 0.000 description 1
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940124599 anti-inflammatory drug Drugs 0.000 description 1
208000002399 aphthous stomatitis Diseases 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000037444 atrophy Effects 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
CIWBQSYVNNPZIQ-XYWKZLDCSA-N betamethasone dipropionate 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)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CIWBQSYVNNPZIQ-XYWKZLDCSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
206010009887 colitis Diseases 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
239000003221 ear drop Substances 0.000 description 1
229940047652 ear drops Drugs 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
235000013305 food Nutrition 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
DVDMHNNCRXYJLU-UHFFFAOYSA-N methoxymethanetriol Chemical compound COC(O)(O)O DVDMHNNCRXYJLU-UHFFFAOYSA-N 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
ZLMGJSDPCYCCQB-UHFFFAOYSA-N propoxymethanetriol Chemical compound CCCOC(O)(O)O ZLMGJSDPCYCCQB-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
208000008742 seborrheic dermatitis Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 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
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- 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
- 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
- C07J5/0061—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 substituted in position 16
- C07J5/0069—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 substituted in position 16 by a saturated or unsaturated hydrocarbon group
- C07J5/0076—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 substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
- 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

DD84275355A 1983-09-07 1984-09-06 Verfahren zur herstellung von neuen corticoidderivaten DD229702A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP58164772A JPS6056997A (ja)	1983-09-07	1983-09-07	新規な６−酸素化コルチコイド／７α−カ−ボネ−ト誘導体およびその製法
JP59120439A JPS611698A (ja)	1984-06-12	1984-06-12	新規なコルチコイド誘導体およびその製法

Publications (1)

Publication Number	Publication Date
DD229702A5 true DD229702A5 (de)	1985-11-13

Family

ID=26458022

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
DD84275355A DD229702A5 (de)	1983-09-07	1984-09-06	Verfahren zur herstellung von neuen corticoidderivaten
DD84267066A DD232497A5 (de)	1983-09-07	1984-09-06	Verfahren zur herstellung von neuen corticoidderivaten
DD84274493A DD229135A5 (de)	1983-09-07	1984-09-06	Verfahren und herstellung von cyclischen 17, 21-orthoester-corticoidderivaten

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
DD84267066A DD232497A5 (de)	1983-09-07	1984-09-06	Verfahren zur herstellung von neuen corticoidderivaten
DD84274493A DD229135A5 (de)	1983-09-07	1984-09-06	Verfahren und herstellung von cyclischen 17, 21-orthoester-corticoidderivaten

Country Status (9)

Country	Link
EP (1)	EP0136586B1 (da)
AT (1)	ATE41013T1 (da)
AU (1)	AU558725B2 (da)
DD (3)	DD229702A5 (da)
DE (1)	DE3476885D1 (da)
DK (1)	DK168631B1 (da)
HU (2)	HU201092B (da)
NO (1)	NO843548L (da)
SU (2)	SU1561827A3 (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4025342A1 (de) *	1990-08-10	1992-02-13	Hoechst Ag	In 17-stellung substituierte corticoid-17-alkylcarbonate, verfahren zu deren herstellung und diese enthaltende arzneimittel
AU710139B2 (en)	1996-05-01	1999-09-16	Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The	21-substituted progesterone derivatives as new antiprogestational agents
US6900193B1 (en)	1996-05-01	2005-05-31	The United States Of America As Represented By The Department Of Health And Human Services	Structural modification of 19-norprogesterone I: 17-α-substituted-11-β-substituted-4-aryl and 21-substituted 19-norpregnadienedione as new antiprogestational agents

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1518179B1 (de) *	1964-10-07	1970-01-02	Warner Lambert Pharmaceutical	Verfahren zur Herstellung von 17alpha-Acyloxy-20-keto-21-desoxy-steroiden
US3558675A (en) *	1969-06-30	1971-01-26	Merck & Co Inc	Steroid carbonates and process
GB1440063A (en) *	1972-08-11	1976-06-23	Glaxo Lab Ltd	17alpha-esters of 17alpha,21-dihydroxy-20-oxo-steroids
DE2735110A1 (de) *	1977-08-04	1979-02-15	Hoechst Ag	Corticoid-17-alkylcarbonate und verfahren zu ihrer herstellung
DE2817988A1 (de) *	1978-04-25	1979-11-08	Hoechst Ag	Corticoid 17-alkylcarbonate und verfahren zu deren herstellung
DE3133082A1 (de) *	1981-08-18	1983-03-10	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue hydrocortison-derivate, ihre herstellung und verwendung

1984
- 1984-08-23 AU AU32311/84A patent/AU558725B2/en not_active Ceased
- 1984-08-24 DK DK407384A patent/DK168631B1/da not_active IP Right Cessation
- 1984-09-04 HU HU843321A patent/HU201092B/hu not_active IP Right Cessation
- 1984-09-04 HU HU852282A patent/HUT44040A/hu unknown
- 1984-09-05 AT AT84110572T patent/ATE41013T1/de not_active IP Right Cessation
- 1984-09-05 EP EP84110572A patent/EP0136586B1/en not_active Expired
- 1984-09-05 DE DE8484110572T patent/DE3476885D1/de not_active Expired
- 1984-09-06 NO NO843548A patent/NO843548L/no unknown
- 1984-09-06 SU SU843792254A patent/SU1561827A3/ru active
- 1984-09-06 DD DD84275355A patent/DD229702A5/de not_active IP Right Cessation
- 1984-09-06 DD DD84267066A patent/DD232497A5/de not_active IP Right Cessation
- 1984-09-06 DD DD84274493A patent/DD229135A5/de not_active IP Right Cessation
1987
- 1987-11-17 SU SU874203674A patent/SU1551250A3/ru active

Also Published As

Publication number	Publication date
EP0136586A3 (en)	1986-01-29
EP0136586A2 (en)	1985-04-10
EP0136586B1 (en)	1989-03-01
DD232497A5 (de)	1986-01-29
HU201092B (en)	1990-09-28
SU1561827A3 (ru)	1990-04-30
DK407384A (da)	1985-03-08
AU3231184A (en)	1985-03-14
NO843548L (no)	1985-03-08
SU1551250A3 (ru)	1990-03-15
HUT37944A (en)	1986-03-28
DE3476885D1 (en)	1989-04-06
AU558725B2 (en)	1987-02-05
ATE41013T1 (de)	1989-03-15
DK407384D0 (da)	1984-08-24
DD229135A5 (de)	1985-10-30
DK168631B1 (da)	1994-05-09
HUT44040A (en)	1988-01-28

Legal Events

Date	Code	Title	Description
1994-11-24	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0135476B1 (de)	1988-09-14	Steroid Carbonsäureester
EP0000742B1 (de)	1982-05-12	Corticoid-17-Alkylcarbonate und Verfahren zu deren Herstellung und diese enthaltende Mittel
DE1443957B1 (de)	1970-01-02	9 alpha-Chlor- bzw. 9 alpha-Fluor-16 beta-methyl-prednisolon-17,21-diester und ein Verfahren zu deren Herstellung
DE2655570A1 (de)	1977-06-16	Neue polyhalogensteroide und verfahren zu ihrer herstellung
CH505802A (de)	1971-04-15	Verfahren zur Herstellung von Estern von 17a-Hydroxysteroiden der Pregnanreihe
DE2743069C2 (de)	1987-03-05	21-Chlor-6&alpha;-fluor-9&alpha;-halogen-11&beta;-hydroxy-16&beta;-methyl-17&alpha;-propionyloxy-pregna-1,4-dien-3,20-dion-Verbindungen, Verfahren zu ihrer Herstellung und pharmazeutische Präparate, welche diese Verbindungen enthalten
DE2538595A1 (de)	1976-03-11	Steroidverbindungen
CH537917A (de)	1973-06-15	Verfahren zur Herstellung von 20-Hydroperoxysteroiden
DD229702A5 (de)	1985-11-13	Verfahren zur herstellung von neuen corticoidderivaten
DE2826257C3 (de)	1980-12-04	Hydrocortison-17,21-diester und Verfahren zu deren Herstellung, diese enthaltende Arzneimittel sowie Hydrocortison -17-propionat als Zwischenprodukt
EP0039311B1 (de)	1984-07-11	Halogenierte Steroide
DE2365992C3 (de)	1982-05-19	6&alpha;-Fluor-17,21-dihydroxy-16&beta;-methylpregna-4,9(11)-dien-3,20-dion-17,21-diacetat und Verfahren zu dessen Herstellung
EP0003341B1 (de)	1984-06-27	11,17-substituierte Pregnane, ihre Herstellung und Verwendung zur Herstellung von pharmazeutischen Präparaten
EP0077541B1 (de)	1985-06-05	Delta-1,3,5-3-Chlor-11-Beta,16-Alpha,17-Alpha,21-tetra-(hydroxy)-pregnan-20-on-16,17-acetonidderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2852055C2 (da)	1988-06-09
EP0023006B1 (de)	1983-03-02	Verfahren zur Herstellung von ungesättigten Steroiden
DE1443957C (de)		9 alpha-Chlor- bzw. 9 alpha-Fluor-. 16 beta-methyl-prednisolon-17,21-diester und ein Verfahren zu deren Herstellung
DE2508136C3 (de)	1979-06-21	Neue Steroide, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Mittel
EP0011121A1 (de)	1980-05-28	Hydrocortisonester, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung
AT229497B (de)	1963-09-25	Verfahren zur Herstellung von 9-Halogen-1, 4-pregnadien-11-olen
AT395428B (de)	1992-12-28	Verfahren zur herstellung von neuen androstancarbothioaten
EP0032103A1 (de)	1981-07-15	Neue Kortikoid-17-thioacetale, ihre Herstellung und Verwendung
DE1568971A1 (de)	1970-06-18	Steroidoxazoline und Verfahren zu ihrer Herstellung
EP0078235A2 (de)	1983-05-04	Dihalogenierte Steroide
DE1768673B1 (de)	1971-10-14	6alpha,9alpha-Difluorprednisolon-17,21-diester