CA1146952A - Process for making alpha-loweralkylfurocoumarins and novel intermediates produced therein - Google Patents
Process for making alpha-loweralkylfurocoumarins and novel intermediates produced thereinInfo
- Publication number
- CA1146952A CA1146952A CA000346784A CA346784A CA1146952A CA 1146952 A CA1146952 A CA 1146952A CA 000346784 A CA000346784 A CA 000346784A CA 346784 A CA346784 A CA 346784A CA 1146952 A CA1146952 A CA 1146952A
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- coumarin
- hydroxy
- reaction
- bromo
- Prior art date
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 23
- 230000008569 process Effects 0.000 title claims description 22
- 239000000543 intermediate Substances 0.000 title abstract description 11
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000002904 solvent Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 235000001671 coumarin Nutrition 0.000 claims abstract description 17
- 229960000956 coumarin Drugs 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 238000005821 Claisen rearrangement reaction Methods 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 18
- FMHHVULEAZTJMA-UHFFFAOYSA-N trioxsalen Chemical group CC1=CC(=O)OC2=C1C=C1C=C(C)OC1=C2C FMHHVULEAZTJMA-UHFFFAOYSA-N 0.000 claims description 17
- 239000007858 starting material Substances 0.000 claims description 14
- 239000012433 hydrogen halide Substances 0.000 claims description 11
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 11
- 238000007363 ring formation reaction Methods 0.000 claims description 8
- 239000000460 chlorine Chemical group 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000007810 chemical reaction solvent Substances 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 18
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract description 7
- MJKVTPMWOKAVMS-UHFFFAOYSA-N 3-hydroxy-1-benzopyran-2-one Chemical compound C1=CC=C2OC(=O)C(O)=CC2=C1 MJKVTPMWOKAVMS-UHFFFAOYSA-N 0.000 abstract description 4
- 230000002159 abnormal effect Effects 0.000 abstract description 4
- 238000002955 isolation Methods 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 28
- 238000001953 recrystallisation Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 238000010586 diagram Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000538 analytical sample Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 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
- 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 4
- 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 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 230000008707 rearrangement Effects 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
- 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 3
- 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 3
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229940093956 potassium carbonate Drugs 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 3
- 229960000850 trioxysalen Drugs 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
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 2
- 238000006418 Brown reaction Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 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
- 239000000706 filtrate Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 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
- VOGHDWQJCXXBMH-RQOWECAXSA-N (z)-1,2-dichlorobut-2-ene Chemical compound C\C=C(/Cl)CCl VOGHDWQJCXXBMH-RQOWECAXSA-N 0.000 description 1
- HTEJLXYOJZOXKM-UHFFFAOYSA-N 1,1-dibromoprop-1-ene Chemical compound CC=C(Br)Br HTEJLXYOJZOXKM-UHFFFAOYSA-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
- 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
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-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
- LKINOBKAEGPXMI-UHFFFAOYSA-N 2,3-dichlorobut-1-ene Chemical compound CC(Cl)C(Cl)=C LKINOBKAEGPXMI-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
- GBGPVUAOTCNZPT-UHFFFAOYSA-N 2-Methylcumarone Chemical compound C1=CC=C2OC(C)=CC2=C1 GBGPVUAOTCNZPT-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
- KKPKUSXDZUCAGY-UHFFFAOYSA-N 3,4-dibromonon-2-ene Chemical compound CCCCCC(Br)C(Br)=CC KKPKUSXDZUCAGY-UHFFFAOYSA-N 0.000 description 1
- KIPCNAPDBRSEFP-UHFFFAOYSA-N 3,4-dibromopent-2-ene Chemical compound CC=C(Br)C(C)Br KIPCNAPDBRSEFP-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
- ASOREXUSJVMMPJ-UHFFFAOYSA-N 7-hydroxy-4-methyl-6-octadecylchromen-2-one Chemical compound CC1=CC(=O)OC2=C1C=C(CCCCCCCCCCCCCCCCCC)C(O)=C2 ASOREXUSJVMMPJ-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
- JHEDXMVWNCTPTI-UHFFFAOYSA-N 7-hydroxy-8-methoxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=C1C=CC(O)=C2OC JHEDXMVWNCTPTI-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
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-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
- 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
- 238000005937 allylation reaction Methods 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 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
- 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 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
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000007499 fusion processing Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001475 halogen functional group Chemical group 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
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- -1 me-thyl Chemical group 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 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
- 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
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 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
- 238000005406 washing 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000408196A CA1163642A (en) | 1979-03-15 | 1982-07-27 | 6-or 8-haloalkyl substituted 7-hydroxycoumarins |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20,935 | 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 |
|---|---|
| CA1146952A true CA1146952A (en) | 1983-05-24 |
Family
ID=21801374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000346784A Expired CA1146952A (en) | 1979-03-15 | 1980-02-29 | Process for making alpha-loweralkylfurocoumarins and novel intermediates produced therein |
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 |
| 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 |
| NL8001517A (nl) | 1980-09-17 |
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |