FI82061C - 17-(isocyano-sulfonylmetylen)- steroider och foerfarande foer deras framstaellning samt 17-(formamido- ylen)taellning. - Google Patents
17-(isocyano-sulfonylmetylen)- steroider och foerfarande foer deras framstaellning samt 17-(formamido- ylen)taellning. Download PDFInfo
- Publication number
- FI82061C FI82061C FI841679A FI841679A FI82061C FI 82061 C FI82061 C FI 82061C FI 841679 A FI841679 A FI 841679A FI 841679 A FI841679 A FI 841679A FI 82061 C FI82061 C FI 82061C
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- FI
- Finland
- Prior art keywords
- groups
- steroid
- group
- atom
- alkyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 53
- 150000003431 steroids Chemical class 0.000 title claims description 53
- -1 isocyano-sulfonylmethylene Chemical group 0.000 title claims description 51
- 238000000034 method Methods 0.000 title claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000004429 atom Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 230000018044 dehydration Effects 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- AMECRMCTYSTXNV-UHFFFAOYSA-N isocyano(sulfonyl)methane Chemical compound O=S(=O)=C[N+]#[C-] AMECRMCTYSTXNV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims 4
- 239000003086 colorant Substances 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000000203 mixture Substances 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 19
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical class CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 15
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 11
- 150000002527 isonitriles Chemical class 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003246 corticosteroid Substances 0.000 description 9
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 229960001334 corticosteroids Drugs 0.000 description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 150000003948 formamides Chemical class 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- JPXLBSACCQTJJU-HVTWWXFQSA-N (8s,9s,10r,13s,14s)-3-methoxy-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C[C@@H]2[C@](CCC(OC)=C3)(C)C3=CC[C@H]2[C@@H]2CCC[C@]21C JPXLBSACCQTJJU-HVTWWXFQSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WSIQEGIPGPEMTC-TXTPUJOMSA-N (8r,9s,10r,13s,14s)-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-one Chemical compound C1C[C@@H]2[C@](CCC(OC)=C3)(C)C3=CC[C@H]2[C@@H]2CCC(=O)[C@]21C WSIQEGIPGPEMTC-TXTPUJOMSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- OHUDHPKMAJDBPI-UHFFFAOYSA-N isocyanomethylsulfonylbenzene Chemical class [C-]#[N+]CS(=O)(=O)C1=CC=CC=C1 OHUDHPKMAJDBPI-UHFFFAOYSA-N 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- DALRJIFFHRECIA-NKILSJRUSA-N (8r,9s,10r,13s,14s)-17-[isocyano-(4-methylphenyl)sulfonylmethylidene]-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C([N+]#[C-])=C1[C@@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4CC[C@H]3[C@@H]2CC1 DALRJIFFHRECIA-NKILSJRUSA-N 0.000 description 2
- UOQFZGVGGMHGEE-UHFFFAOYSA-N 1,1-dihydroxypropan-2-one Chemical group CC(=O)C(O)O UOQFZGVGGMHGEE-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 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 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 description 1
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 1
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 1
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
- USGKSIJYOHEDEV-TXTPUJOMSA-N (8'r,9's,10'r,13's,14's)-10',13'-dimethylspiro[1,3-dioxolane-2,3'-2,4,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthrene]-17'-one Chemical compound C([C@@H]1[C@@H]([C@]2(CC3)C)CC[C@]4([C@H]1CCC4=O)C)C=C2CC13OCCO1 USGKSIJYOHEDEV-TXTPUJOMSA-N 0.000 description 1
- QACYPHYJOCKOAX-ROFHDDJXSA-N (8'r,9's,10'r,13's,14's)-17'-[isocyano-(4-methylphenyl)sulfonylmethylidene]-10',13'-dimethylspiro[1,3-dioxolane-2,3'-2,4,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthrene] Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C([N+]#[C-])=C1[C@@]2(C)CC[C@@H]3[C@@]4(C)CCC5(OCCO5)CC4=CC[C@H]3[C@@H]2CC1 QACYPHYJOCKOAX-ROFHDDJXSA-N 0.000 description 1
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- IPZUAABRLHIHNM-ROFHDDJXSA-N (8r,9s,10r,13s,14s)-17-[isocyano-(4-methoxyphenyl)sulfonylmethylidene]-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene Chemical compound C([C@H]1[C@@H]2CC=C3C=C(CC[C@]3(C)[C@H]2CC[C@@]11C)OC)CC1=C([N+]#[C-])S(=O)(=O)C1=CC=C(OC)C=C1 IPZUAABRLHIHNM-ROFHDDJXSA-N 0.000 description 1
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Classifications
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- 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
- C07J41/0038—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- 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
-
- 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
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- 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
- C07J53/005—3 membered carbocyclic rings in position 12
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP83200616A EP0123734A1 (en) | 1983-04-29 | 1983-04-29 | 17-(Isocyano-sulfonylmethylene)-steroids, 17-(formamido-sulfonylmethylene)-steroids and their preparation |
| EP83200616 | 1983-04-29 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI841679A0 FI841679A0 (fi) | 1984-04-27 |
| FI841679A7 FI841679A7 (fi) | 1984-10-30 |
| FI82061B FI82061B (fi) | 1990-09-28 |
| FI82061C true FI82061C (fi) | 1991-01-10 |
Family
ID=8190949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI841679A FI82061C (fi) | 1983-04-29 | 1984-04-27 | 17-(isocyano-sulfonylmetylen)- steroider och foerfarande foer deras framstaellning samt 17-(formamido- ylen)taellning. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4647410A (enExample) |
| EP (2) | EP0123734A1 (enExample) |
| JP (2) | JPS59206399A (enExample) |
| KR (1) | KR860001469B1 (enExample) |
| AU (1) | AU568643B2 (enExample) |
| CA (1) | CA1257249A (enExample) |
| DE (1) | DE3461381D1 (enExample) |
| DK (2) | DK166545B1 (enExample) |
| ES (2) | ES8608537A1 (enExample) |
| FI (1) | FI82061C (enExample) |
| GR (1) | GR81997B (enExample) |
| HU (2) | HU193207B (enExample) |
| IE (1) | IE57328B1 (enExample) |
| IL (1) | IL71658A (enExample) |
| NO (1) | NO167093C (enExample) |
| NZ (1) | NZ207985A (enExample) |
| PT (1) | PT78503B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0123735A1 (en) * | 1983-04-29 | 1984-11-07 | Gist-Brocades N.V. | New process for the preparation of 20-keto-delta-16-steroids and new intermediate compounds formed in this process |
| HU208437B (en) * | 1988-04-08 | 1993-10-28 | Roussel Uclaf | Process for producing 9-alpha-hydroxy- -17-methylene-steroides for synthetizing corticosteroides |
| HU226413B1 (en) * | 1991-06-25 | 2008-11-28 | Aventis Pharma Sa | Novel 16-(nitro-substituted methyl)pregna-1,4-dien-3,20-dion derivatives and process for producing them |
| FR2681069B1 (fr) * | 1991-09-06 | 1995-04-28 | Roussel Uclaf | Nouveau procede de preparation de l'hydrocortisone et nouveaux intermediaires. |
| FR2683530B1 (fr) * | 1991-11-08 | 1994-01-21 | Roussel Uclaf | Nouveau procede de preparation de derives 20-oxo 17 alpha, 21-dihydroxyles du pregnane et nouveaux intermediaires. |
| WO1997021720A2 (en) | 1995-12-11 | 1997-06-19 | G.D. Searle And Co. | Processes for preparation of 7 alpha-carboxyl 9,11-epoxy steroids and intermediates useful therein and a general process for the epoxidation of olifinic double bonds |
| US6887991B1 (en) | 1996-12-11 | 2005-05-03 | G. D. Searle & Company | Processes for preparation of 9, 11-epoxy steroids and intermediates useful therein |
| NZ336004A (en) | 1996-12-11 | 2001-04-27 | G | Process for preparation of 3-keto-7-alpha-alkoxycarbonyl substituted delta-4,5-steroid by reacting 4,5-dihydro-5,7-lactone steroid substrate in the presence of a base |
| US6372712B1 (en) | 1998-05-22 | 2002-04-16 | The Board Of Trustees Of The Leland Stanford Jr. University | Synthetic bifunctional molecules containing a drug moiety and presenter protein ligand |
| EP2287721A3 (en) | 1999-11-02 | 2011-04-06 | Canon Kabushiki Kaisha | Print control method and apparatus |
| US7235655B2 (en) | 2002-03-22 | 2007-06-26 | Pharmacia & Upjohn Company | Processes to prepare eplerenone |
| EP2671508B1 (en) | 2005-04-28 | 2020-09-16 | Proteus Digital Health, Inc. | Pharma-informatics system |
| US9062126B2 (en) | 2005-09-16 | 2015-06-23 | Raptor Pharmaceuticals Inc. | Compositions comprising receptor-associated protein (RAP) variants specific for CR-containing proteins and uses thereof |
| ES2919563T3 (es) | 2009-02-20 | 2022-07-27 | Enhanx Biopharm Inc | Sistema de administración de medicamentos a base de glutatión |
| KR20180114970A (ko) | 2009-05-06 | 2018-10-19 | 라보라토리 스킨 케어, 인크. | 활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법 |
| CN105481924B (zh) * | 2015-11-24 | 2017-08-15 | 浙江省诸暨合力化学对外贸易有限公司 | 一种黄体酮的制备方法 |
| US20240368212A1 (en) * | 2021-08-26 | 2024-11-07 | Brandeis University | Selective isonitrile inhibitors of cytochrome p450 subtypes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7807631A (nl) * | 1978-07-17 | 1980-01-21 | Gist Brocades Nv | Isocyanoderivaten en hun bereiding. |
| FR2462445A1 (fr) * | 1979-07-31 | 1981-02-13 | Roussel Uclaf | Nouveaux derives 17-/(hydroxymethyl) (formamido) methylene/steroides, leur procede de preparation et leur application a l'introduction de la chaine laterale hydroxyacetyle |
| FR2486947A1 (fr) * | 1980-07-15 | 1982-01-22 | Roussel Uclaf | Nouveaux derives steroides 20-isonitriles 17(20) insatures, leur procede de preparation et leur application a la preparation des steroides 17a-hydroxy 20-ceto |
-
1983
- 1983-04-29 EP EP83200616A patent/EP0123734A1/en not_active Withdrawn
-
1984
- 1984-04-19 AU AU27133/84A patent/AU568643B2/en not_active Ceased
- 1984-04-26 IL IL71658A patent/IL71658A/xx not_active IP Right Cessation
- 1984-04-27 FI FI841679A patent/FI82061C/fi not_active IP Right Cessation
- 1984-04-27 HU HU841661A patent/HU193207B/hu not_active IP Right Cessation
- 1984-04-27 GR GR74531A patent/GR81997B/el unknown
- 1984-04-27 NZ NZ207985A patent/NZ207985A/en unknown
- 1984-04-27 IE IE1038/84A patent/IE57328B1/en not_active IP Right Cessation
- 1984-04-27 JP JP59086019A patent/JPS59206399A/ja active Granted
- 1984-04-27 DE DE8484200595T patent/DE3461381D1/de not_active Expired
- 1984-04-27 CA CA000453026A patent/CA1257249A/en not_active Expired
- 1984-04-27 DK DK212184A patent/DK166545B1/da not_active IP Right Cessation
- 1984-04-27 HU HU842402A patent/HU194277B/hu not_active IP Right Cessation
- 1984-04-27 KR KR1019840002247A patent/KR860001469B1/ko not_active Expired
- 1984-04-27 PT PT78503A patent/PT78503B/pt not_active IP Right Cessation
- 1984-04-27 US US06/604,868 patent/US4647410A/en not_active Expired - Lifetime
- 1984-04-27 EP EP84200595A patent/EP0124934B1/en not_active Expired
- 1984-04-27 NO NO841700A patent/NO167093C/no unknown
- 1984-04-28 ES ES532029A patent/ES8608537A1/es not_active Expired
-
1986
- 1986-04-01 ES ES553609A patent/ES8800263A1/es not_active Expired
-
1992
- 1992-01-08 JP JP4001726A patent/JPH0717673B2/ja not_active Expired - Lifetime
- 1992-02-21 DK DK022192A patent/DK166831B1/da not_active IP Right Cessation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Transfer of assignment of patent |
Owner name: ROUSSEL-UCLAF |
|
| MM | Patent lapsed |
Owner name: ROUSSEL UCLAF SOCIETE ANONYME |