NO780867L - Fremgangsmaate ved fremstilling av steroid-spiro-oxazolidion-derivater - Google Patents

Fremgangsmaate ved fremstilling av steroid-spiro-oxazolidion-derivater

Info

Publication number: NO780867L
Authority: NO; Norway
Prior art keywords: oxo; spiro; carbon atoms; general formula; compound
Prior art date: 1977-03-14

Application number

NO780867A

Other languages

English (en)

Norwegian (no)

Inventor

Sandor Solyom

Lajos Toldy

Katalin Szilagyi

Inge Schafer

Eleonora Szondy

Janos Borvendeg

Ilona Hermann

Original Assignee

Richter Gedeon Vegyeszet

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-03-14

Filing date

1978-03-13

Publication date

1978-09-15

1978-03-13 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1978-09-15 Publication of NO780867L publication Critical patent/NO780867L/no

Links

238000000034 method Methods 0.000 title claims description 76
238000002360 preparation method Methods 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims description 106
125000004432 carbon atom Chemical group C* 0.000 claims description 38
239000000203 mixture Substances 0.000 claims description 26
125000004043 oxo group Chemical group O=* 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000005646 oximino group Chemical group 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
230000003647 oxidation Effects 0.000 claims description 10
238000007254 oxidation reaction Methods 0.000 claims description 10
230000000694 effects Effects 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
239000002585 base Substances 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
150000002576 ketones Chemical class 0.000 claims description 5
239000007788 liquid Substances 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
239000002170 aldosterone antagonist Substances 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
150000002084 enol ethers Chemical class 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
238000007363 ring formation reaction Methods 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
125000000676 alkoxyimino group Chemical group 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
238000006356 dehydrogenation reaction Methods 0.000 claims description 2
238000006704 dehydrohalogenation reaction Methods 0.000 claims description 2
230000026030 halogenation Effects 0.000 claims description 2
238000005658 halogenation reaction Methods 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
GOPUCFKUFOFEIC-UHFFFAOYSA-N 2-methyl-1,3-oxazolidine Chemical compound CC1NCCO1 GOPUCFKUFOFEIC-UHFFFAOYSA-N 0.000 claims 3
239000004480 active ingredient Substances 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
239000007787 solid Substances 0.000 claims 2
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 1
125000005587 carbonate group Chemical group 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 130
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
239000000047 product Substances 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
238000001953 recrystallisation Methods 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000011541 reaction mixture Substances 0.000 description 27
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
239000007858 starting material Substances 0.000 description 16
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 13
239000000155 melt Substances 0.000 description 13
239000000725 suspension Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000005457 ice water Substances 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
150000003431 steroids Chemical class 0.000 description 9
-1 alkenyl isocyanate Chemical class 0.000 description 8
230000007935 neutral effect Effects 0.000 description 8
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000012043 crude product Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
150000003413 spiro compounds Chemical class 0.000 description 5
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 4
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000002178 crystalline material Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
239000000463 material Substances 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
230000002280 anti-androgenic effect Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229960004486 desoxycorticosterone acetate Drugs 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
239000012188 paraffin wax Substances 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 3
229960002256 spironolactone Drugs 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
URDXYWDQNDKHLS-UHFFFAOYSA-N 1-oxa-3-azaspiro[4.5]decane Chemical class O1CNCC11CCCCC1 URDXYWDQNDKHLS-UHFFFAOYSA-N 0.000 description 2
DRSZTATWOSZRAK-UHFFFAOYSA-N 3,4-dibromobutan-2-one Chemical compound CC(=O)C(Br)CBr DRSZTATWOSZRAK-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
238000006036 Oppenauer oxidation reaction Methods 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
239000000538 analytical sample Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000004042 decolorization Methods 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
229910052808 lithium carbonate Inorganic materials 0.000 description 2
229940008015 lithium carbonate Drugs 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
239000012071 phase Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
238000006798 ring closing metathesis reaction Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 2
238000001665 trituration Methods 0.000 description 2
AGAVSENPCRLEAB-AOIWGVFYSA-N (8s,13s,14s)-3-methoxy-13-methyl-7,8,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthren-17-one Chemical compound C1[C@]2(C)C(=O)CC[C@H]2[C@@H]2CCC3=CC(OC)=CC=C3C2=C1 AGAVSENPCRLEAB-AOIWGVFYSA-N 0.000 description 1
150000004057 1,4-benzoquinones Chemical class 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical group O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 description 1
VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
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239000003377 acid catalyst Substances 0.000 description 1
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150000001412 amines Chemical class 0.000 description 1
QZLYKIGBANMMBK-UGCZWRCOSA-N androstane group Chemical group [C@@H]12CCC[C@@]1(C)CC[C@H]1[C@H]2CC[C@H]2CCCC[C@]12C QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
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150000004657 carbamic acid derivatives Chemical class 0.000 description 1
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150000001721 carbon Chemical group 0.000 description 1
VTHIKKVKIVQWHV-UHFFFAOYSA-N chromium(6+) oxygen(2-) pyridine Chemical compound [O-2].[O-2].[O-2].[Cr+6].C1=CC=NC=C1 VTHIKKVKIVQWHV-UHFFFAOYSA-N 0.000 description 1
FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 1
GZRYBYIBLHMWCD-UHFFFAOYSA-N dimethyl(methylidene)-$l^{4}-sulfane Chemical compound CS(C)=C GZRYBYIBLHMWCD-UHFFFAOYSA-N 0.000 description 1
DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
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238000001035 drying Methods 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005048 flame photometry Methods 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
WHCGAWYIUPYPDI-UHFFFAOYSA-N hypochlorous acid O-methylhydroxylamine Chemical compound ClO.CON WHCGAWYIUPYPDI-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000002395 mineralocorticoid Substances 0.000 description 1
VDCLSGXZVUDARN-UHFFFAOYSA-N molecular bromine;pyridine;hydrobromide Chemical compound Br.BrBr.C1=CC=NC=C1 VDCLSGXZVUDARN-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
KPTCZURLWZSRKB-UHFFFAOYSA-N o-prop-2-enylhydroxylamine Chemical compound NOCC=C KPTCZURLWZSRKB-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007790 scraping Methods 0.000 description 1
150000003335 secondary amines Chemical class 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
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
KIEOKOFEPABQKJ-UHFFFAOYSA-N sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229960001712 testosterone propionate Drugs 0.000 description 1
NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/006—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton spiro-condensed
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- 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
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0088—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing unsubstituted amino radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Diabetes (AREA)
Public Health (AREA)
Hematology (AREA)
Endocrinology (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO780867A 1977-03-14 1978-03-13 Fremgangsmaate ved fremstilling av steroid-spiro-oxazolidion-derivater NO780867L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU77GO1364A HU179711B (en)	1977-03-14	1977-03-14	Process for preparing steroid-spiro-oxazolidinone derivatives

Publications (1)

Publication Number	Publication Date
NO780867L true NO780867L (no)	1978-09-15

Family

ID=10996830

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO780867A NO780867L (no)	1977-03-14	1978-03-13	Fremgangsmaate ved fremstilling av steroid-spiro-oxazolidion-derivater

Country Status (19)

Country	Link
US (1)	US4180505A (da)
JP (1)	JPS6050199B2 (da)
AT (1)	AT370113B (da)
AU (1)	AU522931B2 (da)
BE (1)	BE864689A (da)
CA (1)	CA1115691A (da)
CH (1)	CH639399A5 (da)
DE (1)	DE2811101A1 (da)
DK (1)	DK111578A (da)
ES (1)	ES467861A1 (da)
FI (1)	FI65264C (da)
FR (1)	FR2383970A1 (da)
GB (1)	GB1599464A (da)
HU (1)	HU179711B (da)
IL (1)	IL54169A (da)
NL (1)	NL7802784A (da)
NO (1)	NO780867L (da)
SE (1)	SE7802666L (da)
SU (2)	SU931109A3 (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU178397B (en) *	1978-04-01	1982-04-28	Gyogyszerkutato Intezet	Process for preparing substituted derivatives of steroid-spiro-oxazolidione derivatives
HU179980B (en) *	1979-12-28	1983-01-28	Gyogyszerkutato Intezet	Process for preparing substituted steroid-spiro-oxazolidinone derivatives
HU181066B (en) *	1980-03-12	1983-05-30	Gyogyszerkutato Intezet	Process for preparing steroid -spiro-oxathiazolidine derivatives
US4460509A (en) *	1981-08-19	1984-07-17	Beth Israel Medical Center	Chemical synthesis
US7214825B2 (en)	2003-10-17	2007-05-08	Honeywell International Inc.	O-(3-chloropropenyl) hydroxylamine free base

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3272801A (en) *	1964-11-19	1966-09-13	American Home Prod	Steroidal spiro-oxazolidinones
NL7107998A (da) *	1970-07-09	1972-01-11
HU167833B (da) *	1973-07-09	1975-12-25
US4018774A (en) *	1976-02-13	1977-04-19	E. R. Squibb & Sons, Inc.	Steroidal [16α,17-d]isoxazolidines

1977
- 1977-03-14 HU HU77GO1364A patent/HU179711B/hu unknown
1978
- 1978-03-01 IL IL54169A patent/IL54169A/xx unknown
- 1978-03-03 AU AU33834/78A patent/AU522931B2/en not_active Expired
- 1978-03-08 SE SE7802666A patent/SE7802666L/xx unknown
- 1978-03-09 BE BE1008755A patent/BE864689A/xx not_active IP Right Cessation
- 1978-03-10 FI FI780772A patent/FI65264C/fi not_active IP Right Cessation
- 1978-03-10 AT AT0175378A patent/AT370113B/de not_active IP Right Cessation
- 1978-03-13 DK DK111578A patent/DK111578A/da not_active Application Discontinuation
- 1978-03-13 CH CH269078A patent/CH639399A5/de not_active IP Right Cessation
- 1978-03-13 SU SU782590453A patent/SU931109A3/ru active
- 1978-03-13 NO NO780867A patent/NO780867L/no unknown
- 1978-03-13 GB GB9862/78A patent/GB1599464A/en not_active Expired
- 1978-03-13 CA CA298,768A patent/CA1115691A/en not_active Expired
- 1978-03-13 FR FR7807109A patent/FR2383970A1/fr active Granted
- 1978-03-14 ES ES467861A patent/ES467861A1/es not_active Expired
- 1978-03-14 NL NL7802784A patent/NL7802784A/xx not_active Application Discontinuation
- 1978-03-14 US US05/886,349 patent/US4180505A/en not_active Expired - Lifetime
- 1978-03-14 DE DE19782811101 patent/DE2811101A1/de not_active Withdrawn
- 1978-03-14 JP JP53029212A patent/JPS6050199B2/ja not_active Expired
1979
- 1979-11-26 SU SU792846547A patent/SU915806A3/ru active

Also Published As

Publication number	Publication date
US4180505A (en)	1979-12-25
NL7802784A (nl)	1978-09-18
FR2383970B1 (da)	1981-12-04
ATA175378A (de)	1982-07-15
HU179711B (en)	1982-11-29
BE864689A (fr)	1978-09-11
SU915806A3 (en)	1982-03-23
FI65264C (fi)	1984-04-10
ES467861A1 (es)	1978-10-16
FI65264B (fi)	1983-12-30
DK111578A (da)	1978-09-15
IL54169A0 (en)	1978-06-15
AU3383478A (en)	1979-09-06
AT370113B (de)	1983-03-10
SU931109A3 (ru)	1982-05-23
JPS6050199B2 (ja)	1985-11-07
AU522931B2 (en)	1982-07-01
FR2383970A1 (fr)	1978-10-13
FI780772A (fi)	1978-09-15
CH639399A5 (de)	1983-11-15
IL54169A (en)	1981-12-31
DE2811101A1 (de)	1978-10-19
JPS53116372A (en)	1978-10-11
SE7802666L (sv)	1978-09-15
CA1115691A (en)	1982-01-05
GB1599464A (en)	1981-10-07

Publication	Publication Date	Title
AU607948B2 (en)	1991-03-21	9-alpha-hydroxy steroids and process for their preparation
DK163520B (da)	1992-03-09	Substitueret androsta-1,4-dien-3,17-dioner, fremgangsmaade til fremstilling deraf, praeparater indeholdende saadanne forbindelser samt anvendelsen af disse til fremstilling af farmaceutiske praeparater
US4160027A (en)	1979-07-03	Steroid cyanoketones and intermediates
NO178768B (no)	1996-02-19	11 disse
DK167766B1 (da)	1993-12-13	17beta-(cyclopropyloxy(thio))-androst-5-en-3beta-ol- og -4-en-3-on-forbindelser og fremgangsmaade til deres fremstilling
NO780867L (no)	1978-09-15	Fremgangsmaate ved fremstilling av steroid-spiro-oxazolidion-derivater
JPS62158300A (ja)	1987-07-14	１０β−アルキニルエストレン誘導体およびそれらの製造法
US3211756A (en)	1965-10-12	3-hydroxyimino-17alpha-(lower alkyl)-5alpha-androstan-17beta-ols and the optionally substituted 3-acyloxyimino and 3-alkoxyimino derivatives corresponding
NO128608B (da)	1973-12-17
US2855413A (en)	1958-10-07	16-haloestradiol esters and ethers
IE47557B1 (en)	1984-04-18	New process for preparing 3-oxime steroid derivatives
US4331663A (en)	1982-05-25	4α,5α-Epoxy-3,20-dioxopregnane-2α,16α-dicarbonitrile and intermediates and process for preparation, method of use and compositions thereof
US2727907A (en)	1955-12-20	Derivatives of 16-alkanoyloxy-17alpha-hydroxypregnen-20-ones
HU177452B (en)	1981-10-28	Process for preparing new d-homo-steroids
US3364207A (en)	1968-01-16	Polyhydrospiro[estr/androst-4-ene-17, 2'-furan/pyran]-3-one and intermediates
JPS6044319B2 (ja)	1985-10-02	新規なステロイド誘導体の製造法
US3325481A (en)	1967-06-13	3-(optionally substituted)amino-estra-1, 3, 5(10), 8(9), 14-pentaen - 17 - ones and derivatives thereof
US3407219A (en)	1968-10-22	17alpha-alkyl-17beta-methyl-8xi, 9xi, 13xi, 14xi-gona-1,3,5(10)-trien-3-ols and conge
Lenz et al.	1978	Formation of 14. alpha.-cardenolides from 21-acetoxy-20-keto steroids
US3634419A (en)	1972-01-11	17-azasteroids
US3047568A (en)	1962-07-31	16-cyano steroids, intermediates and method of preparing same
Edge et al.	1984	Steroids. Part 21. Photorearrangement of steroidal nitronate salts and a N-butyl spiro-oxaziridine
US3255183A (en)	1966-06-07	Process for the reduction of a faworskii ester
US3171835A (en)	1965-03-02	4, 4, 6, 16-tetraalkyl-5-pregnene steroids and process of preparation
US3491089A (en)	1970-01-20	11-oxygenated steroids and process for their preparation