IL32307A - 14alpha,17alpha-methylenedioxypregnane derivatives,their preparation and pharmaceutical compositions containing them - Google Patents

14alpha,17alpha-methylenedioxypregnane derivatives,their preparation and pharmaceutical compositions containing them

Info

Publication number: IL32307A
Authority: IL; Israel
Prior art keywords: group; general formula; derivatives; compound; derivative
Prior art date: 1968-06-07

Application number

IL32307A

Other languages

English (en)

Other versions

IL32307A0 (en

Original Assignee

Koninklijke Gist Spiritus

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.)

1968-06-07

Filing date

1969-05-28

Publication date

1972-11-28

1969-05-28 Application filed by Koninklijke Gist Spiritus filed Critical Koninklijke Gist Spiritus

1969-07-30 Publication of IL32307A0 publication Critical patent/IL32307A0/xx

1972-11-28 Publication of IL32307A publication Critical patent/IL32307A/en

Links

238000002360 preparation method Methods 0.000 title claims description 16
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
BTOAYZVUZVTWMC-JTPZPXLFSA-N C1CC2CCCC[C@]2(C)[C@@H](CC[C@]23C)[C@@H]1[C@]31CC[C@@]2(CC)OCO1 Chemical class C1CC2CCCC[C@]2(C)[C@@H](CC[C@]23C)[C@@H]1[C@]31CC[C@@]2(CC)OCO1 BTOAYZVUZVTWMC-JTPZPXLFSA-N 0.000 title 1
238000000034 method Methods 0.000 claims description 72
150000001875 compounds Chemical class 0.000 claims description 35
229910052799 carbon Inorganic materials 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 27
125000004429 atom Chemical group 0.000 claims description 13
150000003126 pregnane derivatives Chemical class 0.000 claims description 13
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
150000007942 carboxylates Chemical class 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
150000001721 carbon Chemical class 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 10
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 8
125000004043 oxo group Chemical group O=* 0.000 claims 3
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 claims 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 2
241000282320 Panthera leo Species 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 claims 1
230000001590 oxidative effect Effects 0.000 claims 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[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 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 35
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 25
229960000890 hydrocortisone Drugs 0.000 description 19
239000000203 mixture Substances 0.000 description 18
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 8
-1 halogenated methyl ethyl tetrahydrofuran benzene Chemical class 0.000 description 7
239000007788 liquid Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
241000790917 Dioxys <bee> Species 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000003480 eluent Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000013543 active substance Substances 0.000 description 4
239000004411 aluminium Substances 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
238000009835 boiling Methods 0.000 description 4
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000010410 layer Substances 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
150000003431 steroids Chemical class 0.000 description 4
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000006071 cream Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000000855 fermentation Methods 0.000 description 3
230000004151 fermentation Effects 0.000 description 3
230000002906 microbiologic effect Effects 0.000 description 3
235000015097 nutrients Nutrition 0.000 description 3
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
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 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000006356 dehydrogenation reaction Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
125000002887 hydroxy group Chemical class [H]O* 0.000 description 2
239000006210 lotion Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
229940043265 methyl isobutyl ketone Drugs 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000001509 sodium citrate Substances 0.000 description 2
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
239000004289 sodium hydrogen sulphite Substances 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
229960002317 succinimide Drugs 0.000 description 2
229940099259 vaseline Drugs 0.000 description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
IQXJCCZJOIKIAD-UHFFFAOYSA-N 1-(2-methoxyethoxy)hexadecane Chemical compound CCCCCCCCCCCCCCCCOCCOC IQXJCCZJOIKIAD-UHFFFAOYSA-N 0.000 description 1
YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
DNXUGBMARDFRGG-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Chemical compound O=C1C=CC(=O)C(C#N)=C1C#N DNXUGBMARDFRGG-UHFFFAOYSA-N 0.000 description 1
JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000282412 Homo 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
240000007817 Olea europaea Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
241000282887 Suidae Species 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
239000008366 buffered solution Substances 0.000 description 1
150000004651 carbonic acid esters Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
229950009789 cetomacrogol 1000 Drugs 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
239000000460 chlorine Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 description 1
VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 1
MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
230000000640 hydroxylating effect Effects 0.000 description 1
CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000004313 iron ammonium citrate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000001050 lubricating effect Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
BAAGAEDAYHYUAD-UHFFFAOYSA-N methane;pyridine;sulfuryl dichloride Chemical compound C.ClS(Cl)(=O)=O.C1=CC=NC=C1 BAAGAEDAYHYUAD-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
150000002829 nitrogen Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
229960003868 paraldehyde Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 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
150000003014 phosphoric acid esters Chemical class 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000001608 potassium adipate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
150000003130 pregnenes Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
- Y10S435/913—Aspergillus

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

IL32307A 1968-06-07 1969-05-28 14alpha,17alpha-methylenedioxypregnane derivatives,their preparation and pharmaceutical compositions containing them IL32307A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL6808047A NL6808047A (it)	1968-06-07	1968-06-07

Publications (2)

Publication Number	Publication Date
IL32307A0 IL32307A0 (en)	1969-07-30
IL32307A true IL32307A (en)	1972-11-28

Family

ID=19803848

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL32307A IL32307A (en)	1968-06-07	1969-05-28	14alpha,17alpha-methylenedioxypregnane derivatives,their preparation and pharmaceutical compositions containing them

Country Status (17)

Country	Link
US (1)	US3629243A (it)
AT (1)	AT306933B (it)
BE (1)	BE734180A (it)
BR (1)	BR6909374D0 (it)
CA (1)	CA944758A (it)
CH (1)	CH548991A (it)
DE (1)	DE1928429C3 (it)
DK (1)	DK121436B (it)
ES (1)	ES368120A1 (it)
FR (1)	FR2010397A1 (it)
GB (1)	GB1269160A (it)
IE (1)	IE33147B1 (it)
IL (1)	IL32307A (it)
IT (1)	IT1044716B (it)
NL (1)	NL6808047A (it)
NO (1)	NO132236C (it)
SE (1)	SE364266B (it)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3905962A (en) *	1970-03-06	1975-09-16	Arthur Friedrich Marx	Oestratrienes
DE2451971A1 (de) *	1974-10-31	1976-05-13	Schering Ag	Neue pregnan-21-saeure-derivate
CA1107301A (en) *	1977-12-22	1981-08-18	Union Carbide Corporation	Hydrolysis of alkylene carbonates to alkylene glycols
GB2152783A (en) *	1984-01-07	1985-08-07	Ivan Manners Pick	Telephone handset aid

1968
- 1968-06-07 NL NL6808047A patent/NL6808047A/xx unknown
1969
- 1969-05-28 IL IL32307A patent/IL32307A/en unknown
- 1969-05-30 BR BR209374/69A patent/BR6909374D0/pt unknown
- 1969-06-04 DE DE1928429A patent/DE1928429C3/de not_active Expired
- 1969-06-05 SE SE07972/69A patent/SE364266B/xx unknown
- 1969-06-05 US US831824A patent/US3629243A/en not_active Expired - Lifetime
- 1969-06-06 AT AT537169A patent/AT306933B/de not_active IP Right Cessation
- 1969-06-06 BE BE734180D patent/BE734180A/xx not_active IP Right Cessation
- 1969-06-06 IE IE776/69A patent/IE33147B1/xx unknown
- 1969-06-06 FR FR6918808A patent/FR2010397A1/fr active Pending
- 1969-06-06 GB GB28884/69A patent/GB1269160A/en not_active Expired
- 1969-06-06 NO NO2345/69A patent/NO132236C/no unknown
- 1969-06-06 DK DK308469AA patent/DK121436B/da not_active IP Right Cessation
- 1969-06-06 CA CA053,640A patent/CA944758A/en not_active Expired
- 1969-06-06 IT IT52139/69A patent/IT1044716B/it active
- 1969-06-07 ES ES368120A patent/ES368120A1/es not_active Expired
- 1969-06-09 CH CH869669A patent/CH548991A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
IE33147B1 (en)	1974-04-03
SE364266B (it)	1974-02-18
DK121436B (da)	1971-10-18
BR6909374D0 (pt)	1973-03-13
NO132236B (it)	1975-06-30
DE1928429A1 (de)	1970-02-12
CH548991A (de)	1974-05-15
CA944758A (en)	1974-04-02
DE1928429C3 (de)	1975-06-12
BE734180A (it)	1969-12-08
IT1044716B (it)	1980-04-21
IE33147L (en)	1969-12-07
GB1269160A (en)	1972-04-06
DE1928429B2 (de)	1974-10-24
IL32307A0 (en)	1969-07-30
US3629243A (en)	1971-12-21
NO132236C (it)	1975-10-08
ES368120A1 (es)	1971-05-01
AT306933B (de)	1973-04-25
FR2010397A1 (it)	1970-02-13
NL6808047A (it)	1969-12-09

Publication	Publication Date	Title
CH629824A5 (de)	1982-05-14	Verfahren zur herstellung neuer androstadien-17beta-carbonsaeuren und ihrer ester und salze.
US3483191A (en)	1969-12-09	Steroids
KR920002298B1 (ko)	1992-03-21	샤르트류신 유도체 또는 그염의 제조방법
IL32307A (en)	1972-11-28	14alpha,17alpha-methylenedioxypregnane derivatives,their preparation and pharmaceutical compositions containing them
Peterson et al.	1955	Microbiological Transformation of Steroids. XIII. Oxygenation of 16α, 17α-Oxidoprogesterone to 11α-Hydroxy-16α, 17α-oxidoprogesterone by Rhizopus Nigricans Ehrb.(ATCC 6227b)
US3209000A (en)	1965-09-28	Derivatives of 3beta-hydroxy steroids and the 6- and 16-substituted analogs thereof
US3634460A (en)	1972-01-11	Ring b-secosteroid transformation products and process
US2937975A (en)	1960-05-24	Steroid halohydrins and process therefor
DE1804983A1 (de)	1969-05-14	Verfahren zur Herstellung von Cephalosporansaeurederivaten
Bernstein et al.	1955	Steroidal Cyclic Ketals. XIII. 1 The Conversion of 11-epi-Corticosterone into Corticosterone
US5708164A (en)	1998-01-13	Cephalostatin analogues
EP0000471A1 (de)	1979-02-07	Neue Kortikoide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
US3741990A (en)	1973-06-26	Organic compounds and processes
US3547911A (en)	1970-12-15	Synthesis of antheridiol and its derivatives
IL29631A (en)	1972-01-27	14alpha,17alpha-methylenedioxypregnane derivatives
US3031375A (en)	1962-04-24	17 beta-(halo-hydroxy-propanoyl)-pregnene derivatives
DE2149187C3 (de)	1974-07-11	Neue, enteral wirksame Periplorhamnosid-Derivate und Verfahren zu ihrer Herstellung
CH606071A5 (en)	1978-10-13	Fibrinolytic anhydro-furanose ether derivs.
US3422134A (en)	1969-01-14	Steroids
DE1793046A1 (de)	1972-02-03	16alpha,17alpha-Methylensteroide der Pregnanreihe mit substituierter Methylengruppe
EP0324390A2 (de)	1989-07-19	Nigericinderivate, Verfahren zu deren Herstellung, diese enthaltende Mittel und Verwendung derselben sowie die Verwendung von Nigericin als antiviral wirksame Substanz
US3068243A (en)	1962-12-11	2-keto-delta3, (5) a-norcortisones
US3585192A (en)	1971-06-15	New estrane derivatives
US2989551A (en)	1961-06-20	New cyclo-pregnanes and process for their manufacture
EP0000368B1 (de)	1981-04-29	D-Homosteroide und solche enthaltende Präparate sowie Verfahren zur Herstellung solcher D-Homosteroide