NL8001517A - Werkwijze voor het bereiden van alfa-lager-alkyl- furocoumarines en nieuwe tussenprodukten, die daarbij worden gebruikt. - Google Patents
Werkwijze voor het bereiden van alfa-lager-alkyl- furocoumarines en nieuwe tussenprodukten, die daarbij worden gebruikt. Download PDFInfo
- Publication number
- NL8001517A NL8001517A NL8001517A NL8001517A NL8001517A NL 8001517 A NL8001517 A NL 8001517A NL 8001517 A NL8001517 A NL 8001517A NL 8001517 A NL8001517 A NL 8001517A NL 8001517 A NL8001517 A NL 8001517A
- Authority
- NL
- Netherlands
- Prior art keywords
- hydrogen
- compound
- coumarin
- alkyl
- bromo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 239000000543 intermediate Substances 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 31
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 239000007858 starting material Substances 0.000 claims description 18
- 229960000956 coumarin Drugs 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 235000001671 coumarin Nutrition 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Chemical group 0.000 claims description 11
- 239000012433 hydrogen halide Substances 0.000 claims description 11
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 11
- FMHHVULEAZTJMA-UHFFFAOYSA-N trioxsalen Chemical group CC1=CC(=O)OC2=C1C=C1C=C(C)OC1=C2C FMHHVULEAZTJMA-UHFFFAOYSA-N 0.000 claims description 11
- -1 alkyl furocoumarin derivative Chemical class 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 238000005821 Claisen rearrangement reaction Methods 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 4
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 238000001953 recrystallisation Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 229960000850 trioxysalen Drugs 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000538 analytical sample Substances 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008707 rearrangement Effects 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- YMFWYDYJHRGGPF-UHFFFAOYSA-N 2,3-dibromoprop-1-ene Chemical compound BrCC(Br)=C YMFWYDYJHRGGPF-UHFFFAOYSA-N 0.000 description 4
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- XDROKJSWHURZGO-UHFFFAOYSA-N angelicin Chemical class C1=C2OC=CC2=C2OC(=O)C=CC2=C1 XDROKJSWHURZGO-UHFFFAOYSA-N 0.000 description 4
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 4
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229940093956 potassium carbonate Drugs 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 3
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 2
- MJKVTPMWOKAVMS-UHFFFAOYSA-N 3-hydroxy-1-benzopyran-2-one Chemical compound C1=CC=C2OC(=O)C(O)=CC2=C1 MJKVTPMWOKAVMS-UHFFFAOYSA-N 0.000 description 2
- SIEZLKYPPOEGKM-UHFFFAOYSA-N 7-(2-bromoprop-2-enoxy)-4-methylchromen-2-one Chemical compound C1=C(OCC(Br)=C)C=CC2=C1OC(=O)C=C2C SIEZLKYPPOEGKM-UHFFFAOYSA-N 0.000 description 2
- DOHZWGZYKUIICQ-UHFFFAOYSA-N 7-(2-chloroprop-2-enoxy)-4,8-dimethylchromen-2-one Chemical compound CC1=C(OCC(Cl)=C)C=CC2=C1OC(=O)C=C2C DOHZWGZYKUIICQ-UHFFFAOYSA-N 0.000 description 2
- MVMMGVPSTRNMSV-UHFFFAOYSA-N 7-hydroxy-4,8-dimethylchromen-2-one Chemical compound CC1=C(O)C=CC2=C1OC(=O)C=C2C MVMMGVPSTRNMSV-UHFFFAOYSA-N 0.000 description 2
- 238000006418 Brown reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
- 229940125898 compound 5 Drugs 0.000 description 2
- 150000004775 coumarins Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- ZCCUUQDIBDJBTK-UHFFFAOYSA-N furocoumarin Natural products C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- MLMVLVJMKDPYBM-UHFFFAOYSA-N pseudoisopsoralene Natural products C1=C2C=COC2=C2OC(=O)C=CC2=C1 MLMVLVJMKDPYBM-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical class C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VOGHDWQJCXXBMH-RQOWECAXSA-N (z)-1,2-dichlorobut-2-ene Chemical compound C\C=C(/Cl)CCl VOGHDWQJCXXBMH-RQOWECAXSA-N 0.000 description 1
- MOYUOFHYXNBZCY-UHFFFAOYSA-N 1,2-dibromodec-2-ene Chemical compound CCCCCCCC=C(Br)CBr MOYUOFHYXNBZCY-UHFFFAOYSA-N 0.000 description 1
- PHYLOGHRJZCZPV-UHFFFAOYSA-N 1,2-dibromohex-2-ene Chemical compound CCCC=C(Br)CBr PHYLOGHRJZCZPV-UHFFFAOYSA-N 0.000 description 1
- NKTHMTBUKCWYAV-UHFFFAOYSA-N 1,2-dichloropent-2-ene Chemical compound CCC=C(Cl)CCl NKTHMTBUKCWYAV-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- WKRAPHQGGAHVBX-UHFFFAOYSA-N 2,3-dibromohex-1-ene Chemical compound CCCC(Br)C(Br)=C WKRAPHQGGAHVBX-UHFFFAOYSA-N 0.000 description 1
- RCSWIDXFXVYRQJ-UHFFFAOYSA-N 2,3-dichloropent-1-ene Chemical compound CCC(Cl)C(Cl)=C RCSWIDXFXVYRQJ-UHFFFAOYSA-N 0.000 description 1
- FALCMQXTWHPRIH-UHFFFAOYSA-N 2,3-dichloroprop-1-ene Chemical compound ClCC(Cl)=C FALCMQXTWHPRIH-UHFFFAOYSA-N 0.000 description 1
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
- VRTNIWBNFSHDEB-UHFFFAOYSA-N 3,3-dichloroprop-1-ene Chemical compound ClC(Cl)C=C VRTNIWBNFSHDEB-UHFFFAOYSA-N 0.000 description 1
- MBKQLBKSESXRFQ-UHFFFAOYSA-N 3,4-dibromo-6-methylhept-2-ene Chemical compound CC=C(Br)C(Br)CC(C)C MBKQLBKSESXRFQ-UHFFFAOYSA-N 0.000 description 1
- KKPKUSXDZUCAGY-UHFFFAOYSA-N 3,4-dibromonon-2-ene Chemical compound CCCCCC(Br)C(Br)=CC KKPKUSXDZUCAGY-UHFFFAOYSA-N 0.000 description 1
- VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 description 1
- OJLATCGOJCUTJG-UHFFFAOYSA-N 7-hydroxy-5-methoxy-4-methylchromen-2-one Chemical compound O1C(=O)C=C(C)C2=C1C=C(O)C=C2OC OJLATCGOJCUTJG-UHFFFAOYSA-N 0.000 description 1
- HAQWEMHXSIRYBE-UHFFFAOYSA-N 7-hydroxy-8-methoxycoumarin Chemical compound C1=CC(=O)OC2=C1C=CC(O)=C2OC HAQWEMHXSIRYBE-UHFFFAOYSA-N 0.000 description 1
- GMEKXRVOQDAYAA-UHFFFAOYSA-N 7-hydroxy-8-methylchromen-2-one Chemical compound C1=CC(=O)OC2=C1C=CC(O)=C2C GMEKXRVOQDAYAA-UHFFFAOYSA-N 0.000 description 1
- CJIJXIFQYOPWTF-UHFFFAOYSA-N 7-hydroxycoumarin Natural products O1C(=O)C=CC2=CC(O)=CC=C21 CJIJXIFQYOPWTF-UHFFFAOYSA-N 0.000 description 1
- VOZCJCUUGJFHJP-UHFFFAOYSA-N 9-methoxy-2-methylfuro[3,2-g]chromen-7-one Chemical compound C1=CC(=O)OC2=C1C=C1C=C(C)OC1=C2OC VOZCJCUUGJFHJP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000003512 Claisen condensation reaction Methods 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 206010047642 Vitiligo Diseases 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000005937 allylation reaction Methods 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007499 fusion processing Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- RQSKEMWBCJHQMX-UHFFFAOYSA-N isoscopoletin Natural products COc1cc2OC(=O)CCc2cc1O RQSKEMWBCJHQMX-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- JZBZLRKFJWQZHU-UHFFFAOYSA-N n,n,2,4,6-pentamethylaniline Chemical compound CN(C)C1=C(C)C=C(C)C=C1C JZBZLRKFJWQZHU-UHFFFAOYSA-N 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Substances [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2093579 | 1979-03-15 | ||
| US06/020,935 US4216154A (en) | 1979-03-15 | 1979-03-15 | Process for making α-loweralkylfurocoumarins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8001517A true NL8001517A (nl) | 1980-09-17 |
Family
ID=21801374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8001517A NL8001517A (nl) | 1979-03-15 | 1980-03-14 | Werkwijze voor het bereiden van alfa-lager-alkyl- furocoumarines en nieuwe tussenprodukten, die daarbij worden gebruikt. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4216154A (OSRAM) |
| AT (1) | AT371467B (OSRAM) |
| AU (1) | AU532881B2 (OSRAM) |
| BE (1) | BE882236A (OSRAM) |
| CA (1) | CA1146952A (OSRAM) |
| DE (1) | DE3009508A1 (OSRAM) |
| FR (1) | FR2451379A1 (OSRAM) |
| GB (1) | GB2047686B (OSRAM) |
| IT (1) | IT1193523B (OSRAM) |
| NL (1) | NL8001517A (OSRAM) |
| SE (3) | SE452886B (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1165797B (it) * | 1982-10-18 | 1987-04-29 | Consiglio Nazionale Ricerche | Procedimento di preparazione di alchilangelicine esenti da psoraleni ed alchilangolicine ottenute col procedimento |
| JPH05501713A (ja) * | 1989-10-26 | 1993-04-02 | アイザックス，ステファン，ティー． | 活性化化合物および核酸の失活方法 |
| US5625079A (en) * | 1993-06-28 | 1997-04-29 | Cerus Corporation | Synthesizing psoralen compounds useful as intermediates |
| US5593823A (en) * | 1993-06-28 | 1997-01-14 | Cerus Corporation | Method for inactivating pathogens in blood using photoactivation of 4'-primary amino-substituted psoralens |
| US5399719A (en) * | 1993-06-28 | 1995-03-21 | Steritech, Inc. | Compounds for the photodecontamination of pathogens in blood |
| US6004742A (en) * | 1993-06-28 | 1999-12-21 | Cerus Corporation | Method for inactivation of pathogens in platelets using 4' and 5' primary amino-substituted psoralens |
| US6420570B1 (en) | 1993-06-28 | 2002-07-16 | Cerus Corporation | Psoralen compounds |
| US6004741A (en) * | 1993-06-28 | 1999-12-21 | Cerus Corporation | Method for the photoactivation of 4' and 5' primary aminoalkyl psoralens in platelet preparations |
| US5871900A (en) * | 1993-06-28 | 1999-02-16 | Cerus Corporation | Method of inactivating pathogens in biological fluids using photoactivated 5-primaryamino psoralens |
| US20020115585A1 (en) * | 1996-06-07 | 2002-08-22 | Hei Derek J. | Method and devices for the removal of psoralens from blood products |
| EP1032265B1 (en) | 1997-11-20 | 2003-10-29 | Cerus Corporation | New psoralens for pathogen inactivation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3201421A (en) * | 1962-05-09 | 1965-08-17 | Dept Of Chemistry | Preparation of alkyl psoralens |
-
1979
- 1979-03-15 US US06/020,935 patent/US4216154A/en not_active Expired - Lifetime
-
1980
- 1980-02-29 CA CA000346784A patent/CA1146952A/en not_active Expired
- 1980-03-10 GB GB8008006A patent/GB2047686B/en not_active Expired
- 1980-03-12 IT IT20519/80A patent/IT1193523B/it active
- 1980-03-12 DE DE19803009508 patent/DE3009508A1/de not_active Withdrawn
- 1980-03-14 BE BE0/199805A patent/BE882236A/fr not_active IP Right Cessation
- 1980-03-14 AU AU56475/80A patent/AU532881B2/en not_active Ceased
- 1980-03-14 SE SE8002034A patent/SE452886B/sv not_active IP Right Cessation
- 1980-03-14 AT AT0141880A patent/AT371467B/de not_active IP Right Cessation
- 1980-03-14 FR FR8005711A patent/FR2451379A1/fr active Granted
- 1980-03-14 NL NL8001517A patent/NL8001517A/nl not_active Application Discontinuation
-
1985
- 1985-02-25 SE SE8500913A patent/SE453087B/sv not_active IP Right Cessation
-
1987
- 1987-03-10 SE SE8700999A patent/SE453393B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU532881B2 (en) | 1983-10-20 |
| SE8002034L (sv) | 1980-09-16 |
| DE3009508A1 (de) | 1980-09-25 |
| FR2451379A1 (fr) | 1980-10-10 |
| SE453087B (sv) | 1988-01-11 |
| ATA141880A (de) | 1982-11-15 |
| AU5647580A (en) | 1980-09-18 |
| IT1193523B (it) | 1988-07-08 |
| AT371467B (de) | 1983-06-27 |
| CA1146952A (en) | 1983-05-24 |
| GB2047686B (en) | 1983-09-07 |
| SE8500913D0 (sv) | 1985-02-25 |
| SE453393B (sv) | 1988-02-01 |
| FR2451379B1 (OSRAM) | 1983-07-08 |
| GB2047686A (en) | 1980-12-03 |
| SE452886B (sv) | 1987-12-21 |
| IT8020519A0 (it) | 1980-03-12 |
| SE8700999D0 (sv) | 1987-03-10 |
| US4216154A (en) | 1980-08-05 |
| SE8700999L (sv) | 1987-03-10 |
| BE882236A (fr) | 1980-07-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1174682A (en) | Active compounds | |
| Moffett | Central nervous system depressants. VII. 1 pyridyl coumarins | |
| US4235781A (en) | 6 Or 8 Haloallyl substituted 7-hydroxycoumarins | |
| US5723631A (en) | Coumarin derivatives as retroviral inhibitors | |
| FI59598B (fi) | Nytt foerfarande foer framstaellning av i 9-staellningen eventuellt metoxisubstituerade 7h-furo(3,2-g)(1)bensopyran-7-oner | |
| Desale et al. | p-Dimethylaminopyridine (DMAP): A highly efficient catalyst for one pot, solvent free synthesis of substituted 2-amino-2-chromenes under microwave irradiation | |
| Yavari et al. | Vinyltriphenylphosphonium salt mediated synthesis of functionalized coumarins | |
| Bender et al. | Synthesis and derivatization of 8-acetylpsoralens. Acetyl migrations during Claisen rearrangement | |
| Al-Maharik et al. | Synthesis of lupiwighteone via a para-Claisen–Cope rearrangement | |
| Appendino et al. | The chemistry of coumarin derivatives, part 2. Reaction of 4‐hydroxycoumarin with α, β‐unsaturated aldehydes | |
| US4216154A (en) | Process for making α-loweralkylfurocoumarins | |
| Ibrahim et al. | Synthesis and chemical reactivity of 2-methylchromones | |
| Bois et al. | A one-step synthesis of 5-hydroxyflavones | |
| Howard et al. | 2, 3-Dihydrothiazolo [2, 3-b] quinazolin-5-one | |
| Harvey et al. | A new chromone and flavone synthesis and its utilization for the synthesis of potentially antitumorigenic polycyclic chromones and flavones | |
| Ganguly et al. | Cerium (iii)-catalyzed regioselective coupling of 2-hydroxychalcones and polyphenols: an efficient domino approach towards synthesis of novel dibenzo-2, 8-dioxabicyclo [3.3. 1] nonanes | |
| Kraus et al. | Synthesis of chroman aldehydes that inhibit HIV | |
| Kallitsakis et al. | Synthesis of 4-hydroxy-3-[(E)-2-(6-substituted-9H-purin-9-yl) vinyl] coumarins as lipoxygenase inhibitors | |
| Guiotto et al. | Methylfuroquinolinones: new furocoumarin isosters as potential photoreagents toward DNA | |
| Miyake et al. | Syntheses of flavones via the iodine-mediated oxidative cyclization of 1, 3-diphenylprop-2-en-1-ones | |
| Mathur et al. | Novel approach to 3, 3-dimethyl-4-morpholino-3, 4-dihydrocoumarins via hetero-Diels–Alder reaction | |
| US4230624A (en) | Process for the synthesis of derivatives of the benzofuran, chromene and isochromene type | |
| Traven et al. | The base-catalyzed cyclization of acylmethyl ethers of 7-hydroxycoumarins | |
| KR101841834B1 (ko) | 크로멘오피리디논 화합물의 신규한 합성방법 | |
| Khatri et al. | Facile intramolecular Diels–Alder reaction of 4-(o-propargyloxy) styrylcoumarins leading to highly fluorescent coumarin-containing polycyclic compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DNT | Communications of changes of names of applicants whose applications have been laid open to public inspection |
Free format text: ELDER PHARMACEUTICALS, INC. |
|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |