NL7906214A - Acetyleenderivaten van androst-4-een en werkwijze voor de bereiding en toepassing ervan, alsmede farmaceuti- sche preparaten die deze derivaten bevatten. - Google Patents

Acetyleenderivaten van androst-4-een en werkwijze voor de bereiding en toepassing ervan, alsmede farmaceuti- sche preparaten die deze derivaten bevatten. Download PDF

Info

Publication number: NL7906214A
Authority: NL; Netherlands
Prior art keywords: formula; compounds; radical; carbon atoms; hydrogen atom
Prior art date: 1978-08-16

Application number

NL7906214A

Other languages

English (en)

Dutch (nl)

Original Assignee

Roussel Uclaf

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.)

1978-08-16

Filing date

1979-08-15

Publication date

1980-02-19

1979-08-15 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1980-02-19 Publication of NL7906214A publication Critical patent/NL7906214A/nl

Links

238000002360 preparation method Methods 0.000 title claims description 27
238000000034 method Methods 0.000 title claims description 22
239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
150000000475 acetylene derivatives Chemical class 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 57
-1 alkyl radical Chemical class 0.000 claims description 42
125000004432 carbon atom Chemical group C* 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
229920006395 saturated elastomer Polymers 0.000 claims description 12
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
239000012374 esterification agent Substances 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
125000000468 ketone group Chemical group 0.000 claims description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
150000003254 radicals Chemical class 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 3
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
150000002894 organic compounds Chemical class 0.000 claims 2
125000002252 acyl group Chemical group 0.000 claims 1
239000000047 product Substances 0.000 description 61
239000000243 solution Substances 0.000 description 49
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
238000003756 stirring Methods 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
239000000377 silicon dioxide Substances 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000002253 acid Substances 0.000 description 7
239000003480 eluent Substances 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
235000019270 ammonium chloride Nutrition 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
235000019345 sodium thiosulphate Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
206010061218 Inflammation Diseases 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
206010030113 Oedema Diseases 0.000 description 3
238000005903 acid hydrolysis reaction Methods 0.000 description 3
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 3
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
230000004054 inflammatory process Effects 0.000 description 3
150000002576 ketones Chemical group 0.000 description 3
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 3
239000002674 ointment Substances 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
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 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
150000004057 1,4-benzoquinones Chemical class 0.000 description 2
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 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
XLKNMWIXNFVJRR-UHFFFAOYSA-N boron potassium Chemical compound [B].[K] XLKNMWIXNFVJRR-UHFFFAOYSA-N 0.000 description 2
229940117173 croton oil Drugs 0.000 description 2
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
210000005069 ears Anatomy 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
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 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
SIOSKXVCLBLPGK-FDJRCERISA-N (8s,9s,10r,11r,13s,14s)-3-ethoxy-11-hydroxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-one Chemical compound C1[C@@H](O)[C@@H]2[C@](CCC(OCC)=C3)(C)C3=CC[C@H]2[C@@H]2CCC(=O)[C@]21C SIOSKXVCLBLPGK-FDJRCERISA-N 0.000 description 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
PRDFNJUWGIQQBW-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-yne Chemical group FC(F)(F)C#C PRDFNJUWGIQQBW-UHFFFAOYSA-N 0.000 description 1
ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
241000186063 Arthrobacter Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241001448862 Croton Species 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
239000004593 Epoxy Substances 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
RMOUBSOVHSONPZ-UHFFFAOYSA-N Isopropyl formate Chemical compound CC(C)OC=O RMOUBSOVHSONPZ-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
239000004166 Lanolin Substances 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 0.000 description 1
208000003251 Pruritus Diseases 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
239000004133 Sodium thiosulphate Substances 0.000 description 1
206010041303 Solar dermatitis Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000008365 aqueous carrier Substances 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical group [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
WPDGFKWDLXLZQM-UHFFFAOYSA-N chloroethane formic acid Chemical compound C(=O)O.C(C)Cl WPDGFKWDLXLZQM-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentane carboxylic acid Natural products OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 1
YVHAIVPPUIZFBA-UHFFFAOYSA-N cyclopentaneacetic acid Natural products OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 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
239000012153 distilled water Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000000499 gel Substances 0.000 description 1
229960004275 glycolic acid Drugs 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
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 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
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
- C07J71/0015—Oxiranes at position 9(11)
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0048—Alkynyl derivatives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Pain & Pain Management (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Rheumatology (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL7906214A 1978-08-16 1979-08-15 Acetyleenderivaten van androst-4-een en werkwijze voor de bereiding en toepassing ervan, alsmede farmaceuti- sche preparaten die deze derivaten bevatten. NL7906214A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7823851A FR2433536A1 (fr)	1978-08-16	1978-08-16	Nouveaux derives de l'androst 4-ene, leur procede de preparation et leur application comme medicament
FR7823851		1978-08-16

Publications (1)

Publication Number	Publication Date
NL7906214A true NL7906214A (nl)	1980-02-19

Family

ID=9211827

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7906214A NL7906214A (nl)	1978-08-16	1979-08-15	Acetyleenderivaten van androst-4-een en werkwijze voor de bereiding en toepassing ervan, alsmede farmaceuti- sche preparaten die deze derivaten bevatten.

Country Status (16)

Country	Link
US (1)	US4232015A (it)
JP (1)	JPS5528982A (it)
AT (1)	AT368520B (it)
AU (1)	AU524232B2 (it)
BE (1)	BE878256A (it)
CH (1)	CH641814A5 (it)
DE (1)	DE2933258A1 (it)
FR (1)	FR2433536A1 (it)
GB (1)	GB2029833B (it)
HU (1)	HU180520B (it)
IE (1)	IE48931B1 (it)
IT (1)	IT1164040B (it)
NL (1)	NL7906214A (it)
PT (1)	PT70060A (it)
SE (1)	SE435186B (it)
ZA (1)	ZA793967B (it)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4424218A (en)	1979-08-17	1984-01-03	Roussel Uclaf	Novel 3 α-amino steroids
FR2468617A1 (fr) *	1979-10-26	1981-05-08	Roussel Uclaf	Nouveaux derives acetyleniques chlores de l'androst-4-ene leur procede de preparation, et leur application a titre de medicament et les compositions pharmaceutiques les renfermant
US4383947A (en) *	1981-07-24	1983-05-17	The Upjohn Company	Introduction of a fluorine atom
US4488995A (en) *	1984-02-06	1984-12-18	E. R. Squibb & Sons, Inc.	Androstene-17β-alkylthiomethyl ethers
US6740646B2 (en) *	2002-01-16	2004-05-25	Biotest Laboratories, Llc	Bioavailable prodrugs of androgenic steroids and related method
JP4636847B2 (ja) *	2004-10-13	2011-02-23	株式会社ロッテ	全粒粉からなる小麦粉の加工方法及びその加工方法により得られた加工小麦粉並びにその加工小麦粉を使用した食品

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2740798A (en) *	1953-05-25	1956-04-03	Searle & Co	11 beta-hydroxy-17-ethynyl testosterone and esters thereof
US3010957A (en) *	1958-11-26	1961-11-28	Schering Corp	Ethinyl androstadienes
FR1349113A (fr) *	1959-01-28	1964-01-17	Upjohn Co	Procédé de fabrication de 6-fluoro-11 oxygéné-17-bêta-hydroxy-17 alpha-alkynyl inférieur-4-androstène-3-ones et leurs dérivés acylés
GB1081494A (en) *	1965-09-14	1967-08-31	British Drug Houses Ltd	17ª-(alka-1',3'-diynyl)-steroids
US3793308A (en) *	1972-11-08	1974-02-19	Upjohn Co	4-spiro(cyclopropyl)androstenes and process for their production
SE7801152L (sv) *	1977-02-22	1978-08-23	Roussel Uclaf	Sett att framstella 17alfa-acetylen-derivat av androst-4-en

1978
- 1978-08-16 FR FR7823851A patent/FR2433536A1/fr active Granted
1979
- 1979-07-04 SE SE7905865A patent/SE435186B/sv not_active IP Right Cessation
- 1979-07-24 HU HU79RO1032A patent/HU180520B/hu not_active IP Right Cessation
- 1979-08-02 ZA ZA00793967A patent/ZA793967B/xx unknown
- 1979-08-06 US US06/063,939 patent/US4232015A/en not_active Expired - Lifetime
- 1979-08-13 PT PT70060A patent/PT70060A/pt unknown
- 1979-08-14 IT IT50049/79A patent/IT1164040B/it active
- 1979-08-14 AT AT0553479A patent/AT368520B/de not_active IP Right Cessation
- 1979-08-14 BE BE0/196747A patent/BE878256A/fr not_active IP Right Cessation
- 1979-08-15 AU AU49958/79A patent/AU524232B2/en not_active Ceased
- 1979-08-15 CH CH749079A patent/CH641814A5/fr not_active IP Right Cessation
- 1979-08-15 NL NL7906214A patent/NL7906214A/nl not_active Application Discontinuation
- 1979-08-16 JP JP10363879A patent/JPS5528982A/ja active Granted
- 1979-08-16 GB GB7928508A patent/GB2029833B/en not_active Expired
- 1979-08-16 IE IE1578/79A patent/IE48931B1/en not_active IP Right Cessation
- 1979-08-16 DE DE19792933258 patent/DE2933258A1/de active Granted

Also Published As

Publication number	Publication date
AU4995879A (en)	1980-03-06
PT70060A (fr)	1979-09-01
BE878256A (fr)	1980-02-14
SE435186B (sv)	1984-09-10
IT7950049A0 (it)	1979-08-14
JPS5528982A (en)	1980-02-29
JPS636559B2 (it)	1988-02-10
IE791578L (en)	1980-02-16
FR2433536A1 (fr)	1980-03-14
GB2029833B (en)	1983-04-27
ATA553479A (de)	1982-02-15
GB2029833A (en)	1980-03-26
SE7905865L (sv)	1980-02-17
AU524232B2 (en)	1982-09-09
HU180520B (en)	1983-03-28
FR2433536B1 (it)	1981-07-24
CH641814A5 (fr)	1984-03-15
IE48931B1 (en)	1985-06-26
IT1164040B (it)	1987-04-08
AT368520B (de)	1982-10-25
DE2933258A1 (de)	1980-02-28
DE2933258C2 (it)	1990-10-25
US4232015A (en)	1980-11-04
ZA793967B (en)	1980-07-30

Publication	Publication Date	Title
DE1618830C3 (de)	1975-02-20	In 3-und 17-Stellung sauerstoffhaltige 11 beta-OB-13beta-C-gona-1,3,5(10)-triene und Verfahren zu ihrer Herstellung
CA2406847C (en)	2009-11-17	Regioselective and stereoselective oxidation of fused ring systems useful for the preparation of aminosterols
NL7906214A (nl)	1980-02-19	Acetyleenderivaten van androst-4-een en werkwijze voor de bereiding en toepassing ervan, alsmede farmaceuti- sche preparaten die deze derivaten bevatten.
US4634694A (en)	1987-01-06	Novel Δ4 - and Δ5 -androstene derivatives and pharmaceutical compositions containing these derivatives
US3423433A (en)	1969-01-21	Method of producing 3-keto-4,6-bisdehydro-6-halogeno-9beta,10alpha-steroids
Foster et al.	1976	Synthesis of steroidal cyclophosphamides
WO1991018918A1 (de)	1991-12-12	VERFAHREN ZUR HERSTELLUNG VON 10β-H-STEROIDEN
US3032552A (en)	1962-05-01	1-methyl steroids of the androstane series
US3579509A (en)	1971-05-18	Process and 6-beta-substituted ethyl intermediates for preparing 6,6-ethylene-3-keto-delta**4 steroids
LU81497A1 (fr)	1980-02-14	Nouveaux derives acetyleniques de l'androst-4-ene,leur procede de preparation,leur application comme medicament et les compositions pharmaceutiques les renfermant
PT87117B (pt)	1992-07-31	Processo para a preparacao de 17 a-etinil-17 b-hidroxi-18-metil-4,15-estradieno-3-ona e novos produtos intermediarios para este processo
US3207767A (en)	1965-09-21	19-alkyl androstanes
US3682895A (en)	1972-08-08	Synthesis of 3-hydroxy-5-bufa-20,22-dienolide
US4066666A (en)	1978-01-03	15-oxasteroids
US4044022A (en)	1977-08-23	15-Oxasteroids
EP0866798B1 (en)	2003-05-14	Preparation of ester derivatives of steroids
Wicha et al.	1967	Transformations of steroidal neopentyl systems. II. Migration of acetate from the 3β-to the 19-hydroxyl in Δ5 and A/B-trans steroids
DE1643010A1 (de)	1971-04-15	Verfahren zur Herstellung von 17alpha-Alkinyl-17ss-alkanoyloxy-Steroiden der Andostran- und Oestranreihe
US3417111A (en)	1968-12-17	10-formyl fluoride and -acetyl steroids and processes for their preparation
US4053487A (en)	1977-10-11	15-oxaandrostanes and 15-oxopregnanes
DE1493163C3 (de)	1974-04-11	nalpha-Äthinyl-ie-methyl-Delta hoch 4-östren-3 beta-17 betadiole, Verfahren zu deren Herstellung sowie diese enthaltende Mittel
US3444188A (en)	1969-05-13	7-fluoro-b-homo steroids and their preparation
US4096142A (en)	1978-06-20	14,19-Dioxygenated steroid compounds and their 14-dehydro analogs and process for the preparation thereof
KR100249554B1 (ko)	2000-03-15	6-치환된 스테로이드, 그것의 제조방법 및 그것을 포함하는 제약학적 조성물
US3952018A (en)	1976-04-20	15-Oxasteroids

Legal Events

Date	Code	Title
1985-01-01	A85	Still pending on 85-01-01
1986-07-01	BA	A request for search or an international-type search has been filed
1986-07-01	BB	A search report has been drawn up
1986-11-03	BC	A request for examination has been filed
1996-05-01	BV	The patent application has lapsed