FR2465749A2 - Nouveau procede de preparation de derives (17 r)7-alkyl 2'-oxydospiro/androst 4ene 17,5'-(1',2') oxathiolane - Google Patents

Nouveau procede de preparation de derives (17 r)7-alkyl 2'-oxydospiro/androst 4ene 17,5'-(1',2') oxathiolane Download PDF

Info

Publication number: FR2465749A2
Authority: FR; France
Prior art keywords: alkyl; sep; formula; hydroxy; product
Prior art date: 1979-09-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

FR7923546A

Other languages

English (en)

French (fr)

Other versions

FR2465749B2 (de

Inventor

Genevieve Rousseau

Vesperto Torelli

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi Aventis France

Original Assignee

Roussel Uclaf SA

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.)

1979-09-21

Filing date

1979-09-21

Publication date

1981-03-27

1979-09-21 Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA

1979-09-21 Priority to FR7923546A priority Critical patent/FR2465749A2/fr

1981-03-27 Publication of FR2465749A2 publication Critical patent/FR2465749A2/fr

1982-09-17 Application granted granted Critical

1982-09-17 Publication of FR2465749B2 publication Critical patent/FR2465749B2/fr

Status Granted legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 title claims abstract description 5
150000004791 alkyl magnesium halides Chemical class 0.000 title abstract description 4
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 title 2
VNMKEQYMVQDWOV-WQSQPHBGSA-N (8S,9S,10R,13R,14S,17R)-17-(2-butylsulfonylethyl)-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C(CCC)S(=O)(=O)CC[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O VNMKEQYMVQDWOV-WQSQPHBGSA-N 0.000 title 1
229960002317 succinimide Drugs 0.000 title 1
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims abstract description 7
125000005843 halogen group Chemical group 0.000 claims abstract description 3
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims abstract 4
125000004429 atom Chemical group 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
101150117093 alc2 gene Proteins 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
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 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
-1 magnesium alkyl halide Chemical class 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
230000000694 effects Effects 0.000 abstract description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 5
229910052700 potassium Inorganic materials 0.000 abstract description 5
239000011591 potassium Substances 0.000 abstract description 5
208000004880 Polyuria Diseases 0.000 abstract description 4
230000035619 diuresis Effects 0.000 abstract description 4
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 abstract description 3
PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 abstract description 3
206010019280 Heart failures Diseases 0.000 abstract description 3
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 abstract description 3
229960002478 aldosterone Drugs 0.000 abstract description 3
230000001548 androgenic effect Effects 0.000 abstract description 3
229910052708 sodium Inorganic materials 0.000 abstract description 3
239000011734 sodium Substances 0.000 abstract description 3
206010020772 Hypertension Diseases 0.000 abstract description 2
230000002280 anti-androgenic effect Effects 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 abstract 1
239000000047 product Substances 0.000 description 57
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical compound C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 description 9
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000003814 drug Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
102000001307 androgen receptors Human genes 0.000 description 4
108010080146 androgen receptors Proteins 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
229960003604 testosterone Drugs 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
DHYMIGDMHYMJAQ-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2C=CCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 DHYMIGDMHYMJAQ-BYZMTCBYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HCJKXXMOOMBBPY-IEJDVFFQSA-N [2-[(8s,9s,10r,11s,13r,14s,17s)-13-formyl-11-hydroxy-10-methyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 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=O)C[C@@H]2O HCJKXXMOOMBBPY-IEJDVFFQSA-N 0.000 description 2
239000002170 aldosterone antagonist Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
NINLAYUXSUKKHW-UHFFFAOYSA-N androsta-3,5(6)-dien-17-one Natural products C1=CCCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 NINLAYUXSUKKHW-UHFFFAOYSA-N 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 2
SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
229940045803 cuprous chloride Drugs 0.000 description 2
210000000172 cytosol Anatomy 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000010828 elution Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
OHFYLRRECABVSF-NWSAAYAGSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 OHFYLRRECABVSF-NWSAAYAGSA-N 0.000 description 1
BTTWKVFKBPAFDK-UHFFFAOYSA-N (9beta,10alpha)-Androst-4-ene-3,17-dione Natural products OC1CCC2(C)C3CCC(C)(C(CC4)O)C4C3CCC2=C1 BTTWKVFKBPAFDK-UHFFFAOYSA-N 0.000 description 1
YPRPSRLQZMDWFO-UHFFFAOYSA-N 2-methyl-2-methylsulfinylpropane Chemical compound CS(=O)C(C)(C)C YPRPSRLQZMDWFO-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
229920000084 Gum arabic Polymers 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
208000037849 arterial hypertension Diseases 0.000 description 1
XDLDASNSMGOEMX-UHFFFAOYSA-N benzene benzene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1 XDLDASNSMGOEMX-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 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
239000003795 chemical substances by application Substances 0.000 description 1
OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
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 1
239000008103 glucose Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
108091008039 hormone receptors Proteins 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000027939 micturition Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
HHQJWDKIRXRTLS-UHFFFAOYSA-N n'-bromobutanediamide Chemical compound NC(=O)CCC(=O)NBr HHQJWDKIRXRTLS-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
AYGFEWYXKDFVIQ-NWSAAYAGSA-N pregn-4-en-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 AYGFEWYXKDFVIQ-NWSAAYAGSA-N 0.000 description 1
238000004321 preservation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J33/005—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton spiro-condensed
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)

FR7923546A 1979-09-21 1979-09-21 Nouveau procede de preparation de derives (17 r)7-alkyl 2'-oxydospiro/androst 4ene 17,5'-(1',2') oxathiolane Granted FR2465749A2 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
FR7923546A FR2465749A2 (fr)	1979-09-21	1979-09-21	Nouveau procede de preparation de derives (17 r)7-alkyl 2'-oxydospiro/androst 4ene 17,5'-(1',2') oxathiolane

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7923546A FR2465749A2 (fr)	1979-09-21	1979-09-21	Nouveau procede de preparation de derives (17 r)7-alkyl 2'-oxydospiro/androst 4ene 17,5'-(1',2') oxathiolane

Publications (2)

Publication Number	Publication Date
FR2465749A2 true FR2465749A2 (fr)	1981-03-27
FR2465749B2 FR2465749B2 (de)	1982-09-17

Family

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Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FR7923546A Granted FR2465749A2 (fr)	1979-09-21	1979-09-21	Nouveau procede de preparation de derives (17 r)7-alkyl 2'-oxydospiro/androst 4ene 17,5'-(1',2') oxathiolane

Country Status (1)

Country	Link
FR (1)	FR2465749A2 (de)

1979
- 1979-09-21 FR FR7923546A patent/FR2465749A2/fr active Granted

Also Published As

Publication number	Publication date
FR2465749B2 (de)	1982-09-17

Publication	Publication Date	Title
EP0196707B1 (de)	1989-09-27	In Stellung 11 und 17 und gegebenenfalls in Stellung 2 substituierte 19-Nor-Steroide, ihre Herstellung, ihre Anwendung als Arzneimittel, die sie enthaltenden Zusammensetzungen und die erhaltenen Zwischenprodukte
EP0188396B1 (de)	1989-08-30	In Stellung 10 substituierte Steroide, ihre Herstellung, Zwischenprodukte in ihrer Herstellung, ihre Anwendung als Arzneimittel und pharmazeutische Zusammensetzungen,die sie enthalten
CA1303025C (fr)	1992-06-09	Derives 17beta a-oh 19-nor steroides substitues en 17alpha, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant
FR2584725A1 (fr)	1987-01-16	Androsta-1,4-diene-3,17-diones substituees, leur procede de fabrication et medicaments les contenant
JP2000256390A (ja)	2000-09-19	性ステロイド活性を抑制するために用いるエストロゲン核誘導体の医薬組成物
FR2639045A2 (fr)	1990-05-18	Nouveaux produits derives de la structure 3-ceto-delta-4,9-19-nor steroides et leur application comme medicaments
EP0414606A2 (de)	1991-02-27	Omega-Phenylaminoalkansäuren, die durch ein 19-nor-Steroidrest am Phenylrest substituiert sind, ihre Salze, ein Verfahren zu ihrer Herstellung, sowie Zwischenprodukte dieses Verfahrens, ihre Verwendung als Arzneimittel und pharmazeutische Präparate davon
EP0056000B1 (de)	1984-09-26	17-(Alkoxycarbonyl)(formamid)methylen-Steroidderivate und ihre Herstellung
EP0313960A1 (de)	1989-05-03	In Position-10 durch ein Radikal mit Doppel- bzw. Dreifachbindung substituierte Steroide und Verfahren zu ihrer Herstellung
EP0018245B1 (de)	1982-06-02	7-Alkyl-Steroidderivate, Verfahren zu ihrer Herstellung, ihre Verwendung in Arzneimitteln und pharmazeutische Zusammensetzungen, die sie enthalten
CA1096857A (fr)	1981-03-03	PROCEDE DE PREPARATION DE NOUVEAUX DERIVES 17- SPIROSULTINES ET DES.gamma.-HYDROXY ACIDES
EP0443957B1 (de)	1995-05-10	Neue 17-spiro substituierte Steroide, Verfahren zu deren Herstellung und Zwischenprodukten davon, ihre Verwendung als Arzneimittel sowie pharmazeutische Präparate davon
EP0101383B1 (de)	1986-11-12	14-Aminosteroidderivate, ihre therapeutische Anwendung und Verfahren zu ihrer Herstellung
CA1051419A (fr)	1979-03-27	Procede de preparation de nouveaux derives steroidiques
FR2465749A2 (fr)	1981-03-27	Nouveau procede de preparation de derives (17 r)7-alkyl 2'-oxydospiro/androst 4ene 17,5'-(1',2') oxathiolane
EP0055170B1 (de)	1984-10-24	In Stellung 7 substituierte 3-keto-delta-4- oder -delta-1,4-Steroidderivate, ihre Herstellung, ihre Verwendung als Arzneimittel und pharmazeutische Zusammensetzungen, die sie enthalten
EP0044575B1 (de)	1984-03-21	Zwischenprodukte in der Herstellung von 2-substituierten 19-nor-Steroiden
CA1072540A (fr)	1980-02-26	Procede de preparation de nouveaux 2,2-dimethyl steroides
CA1096372A (fr)	1981-02-24	Procede de preparation de nouveaux 2,2-dimethyl 19- nor steroides
CA1121341A (fr)	1982-04-06	PROCEDE DE PREPARATION DE NOUVEAUX DERIVES STEROIDES 17 SPIROSULTINES, LES.gamma.-HYDROXY ACIDES CORRESPONDANTS
CA1114366A (fr)	1981-12-15	PROCEDE DE PREPARATION DE DERIVES 17.alpha.-ACETYLENIQUES DE L'ANDROST 4-ENE
HUP0301592A2 (hu)	2003-09-29	16alfa-metil- vagy etil-szubsztituált ösztrogének és ezeket tartalmazó gyógyszerkészítmények
EP0375559B1 (de)	1993-07-21	Steroidderivate, die ein Alkylthioradikal in Stellung 4 enthalten, Verfahren zu deren Herstellung, ihre Anwendung als Arzneimittel und pharmazeutische Zusammensetzungen, die sie enthalten
EP0437552A1 (de)	1991-07-24	In stellung 17/21-alkylierte 19-nor-progesteronderivate
FR2625505A2 (fr)	1989-07-07	Nouveaux derives steroides substitues en 11beta leur procede de preparation et leur application comme medicaments et les compositions pharmaceutiques les renfermant