DE2707746A1 - 5,6-substituierte, kondensierte 4-(2h)-aminoalkoxy-2,3-pyranone, verfahren zu deren herstellung und sie enthaltende arzneimittel - Google Patents
5,6-substituierte, kondensierte 4-(2h)-aminoalkoxy-2,3-pyranone, verfahren zu deren herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE2707746A1 DE2707746A1 DE19772707746 DE2707746A DE2707746A1 DE 2707746 A1 DE2707746 A1 DE 2707746A1 DE 19772707746 DE19772707746 DE 19772707746 DE 2707746 A DE2707746 A DE 2707746A DE 2707746 A1 DE2707746 A1 DE 2707746A1
- Authority
- DE
- Germany
- Prior art keywords
- mol
- radical
- multiplet
- spectrum
- yield
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 229940126601 medicinal product Drugs 0.000 title 1
- -1 alkyl radical Chemical class 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical group O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical group C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 claims description 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
- 238000004458 analytical method Methods 0.000 description 71
- 239000007787 solid Substances 0.000 description 57
- 238000002329 infrared spectrum Methods 0.000 description 46
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 41
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- 235000019441 ethanol Nutrition 0.000 description 29
- ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 20
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- CBHMYFPBBDCWSY-UHFFFAOYSA-N 4-hydroxy-3-phenylchromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C1=CC=CC=C1 CBHMYFPBBDCWSY-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 10
- 229960000956 coumarin Drugs 0.000 description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- SAXYZBSZFHZMKM-UHFFFAOYSA-N 4-hydroxy-3-phenyl-5,6,7,8-tetrahydrochromen-2-one Chemical compound OC=1C=2CCCCC=2OC(=O)C=1C1=CC=CC=C1 SAXYZBSZFHZMKM-UHFFFAOYSA-N 0.000 description 8
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- HJIMOIOCTZRUKS-UHFFFAOYSA-N 4-(3-chloro-2-methylpropyl)morpholine Chemical compound ClCC(C)CN1CCOCC1 HJIMOIOCTZRUKS-UHFFFAOYSA-N 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 5
- 230000002152 alkylating effect Effects 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229960001789 papaverine Drugs 0.000 description 5
- APFWLFUGBMRXCS-UHFFFAOYSA-N 4,7-dihydroxy-3-phenylchromen-2-one Chemical compound O=C1OC2=CC(O)=CC=C2C(O)=C1C1=CC=CC=C1 APFWLFUGBMRXCS-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 235000001671 coumarin Nutrition 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- VEXKIOOWPFOHQI-UHFFFAOYSA-N 1-(3-chloro-2-methylpropyl)piperidine Chemical compound ClCC(C)CN1CCCCC1 VEXKIOOWPFOHQI-UHFFFAOYSA-N 0.000 description 3
- IHHWIRIIIZBIDV-UHFFFAOYSA-N 4,5-dihydroxy-3-phenylchromen-2-one Chemical compound OC=1C=2C(O)=CC=CC=2OC(=O)C=1C1=CC=CC=C1 IHHWIRIIIZBIDV-UHFFFAOYSA-N 0.000 description 3
- JFSGNLVZNFXDKN-UHFFFAOYSA-N 4-(2-hydroxy-3-morpholin-4-ylpropoxy)-3-phenylchromen-2-one Chemical compound C1COCCN1CC(O)COC(C=1C=CC=CC=1OC1=O)=C1C1=CC=CC=C1 JFSGNLVZNFXDKN-UHFFFAOYSA-N 0.000 description 3
- PIAZYBLGBSMNLX-UHFFFAOYSA-N 4-(3-chloropropyl)morpholine Chemical compound ClCCCN1CCOCC1 PIAZYBLGBSMNLX-UHFFFAOYSA-N 0.000 description 3
- UIJJGCUHRDYWKR-UHFFFAOYSA-N 4-hydroxy-7-methoxy-3-phenylchromen-2-one Chemical compound O=C1OC2=CC(OC)=CC=C2C(O)=C1C1=CC=CC=C1 UIJJGCUHRDYWKR-UHFFFAOYSA-N 0.000 description 3
- BOLUBUXQYPIEFJ-UHFFFAOYSA-N 4-hydroxy-8-methoxy-3-phenylchromen-2-one Chemical compound O=C1OC=2C(OC)=CC=CC=2C(O)=C1C1=CC=CC=C1 BOLUBUXQYPIEFJ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 3
- 229960002768 dipyridamole Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229940124549 vasodilator Drugs 0.000 description 3
- 239000003071 vasodilator agent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 2
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 2
- NVOGDDBXRPTHRN-UHFFFAOYSA-N 4,8-dihydroxy-3-phenylchromen-2-one Chemical compound O=C1OC=2C(O)=CC=CC=2C(O)=C1C1=CC=CC=C1 NVOGDDBXRPTHRN-UHFFFAOYSA-N 0.000 description 2
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical compound C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 229960004126 codeine Drugs 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 230000001335 demethylating effect Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- FGYDHYCFHBSNPE-UHFFFAOYSA-N diethyl phenylmalonate Chemical compound CCOC(=O)C(C(=O)OCC)C1=CC=CC=C1 FGYDHYCFHBSNPE-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 210000001105 femoral artery Anatomy 0.000 description 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- VHPJXYDOOWUMBR-UHFFFAOYSA-N 1,2-dichlorocyclohexa-1,3,5-triene Chemical group ClC1=C[C]=CC=C1Cl VHPJXYDOOWUMBR-UHFFFAOYSA-N 0.000 description 1
- VFLQQZCRHPIGJU-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine;hydron;chloride Chemical compound Cl.ClCCN1CCCCC1 VFLQQZCRHPIGJU-UHFFFAOYSA-N 0.000 description 1
- RMGFLMXDCGQKPS-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine Chemical compound ClCCN1CCCC1 RMGFLMXDCGQKPS-UHFFFAOYSA-N 0.000 description 1
- DKGQENSYEBYPNT-UHFFFAOYSA-N 1-(3-chloro-2-methylpropyl)-4-methylpiperazine Chemical compound ClCC(C)CN1CCN(C)CC1 DKGQENSYEBYPNT-UHFFFAOYSA-N 0.000 description 1
- UMYMWCKSANKFPI-UHFFFAOYSA-N 2-(2-chloroethyl)-1-methylpiperidine Chemical compound CN1CCCCC1CCCl UMYMWCKSANKFPI-UHFFFAOYSA-N 0.000 description 1
- 229940061334 2-phenylphenol Drugs 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
- RIXOZERNLGIRHT-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-4-hydroxychromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C1=CC=C(Cl)C(Cl)=C1 RIXOZERNLGIRHT-UHFFFAOYSA-N 0.000 description 1
- RLJRQAYQPRQBJO-UHFFFAOYSA-N 3-(3-chlorophenyl)-4-hydroxychromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C1=CC=CC(Cl)=C1 RLJRQAYQPRQBJO-UHFFFAOYSA-N 0.000 description 1
- RQHGTTKDFLSVHA-UHFFFAOYSA-N 3-(4-bromophenyl)-4-hydroxychromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C1=CC=C(Br)C=C1 RQHGTTKDFLSVHA-UHFFFAOYSA-N 0.000 description 1
- SZIMSZJNBQFDAQ-UHFFFAOYSA-N 3-(4-fluorophenyl)-4-hydroxychromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C1=CC=C(F)C=C1 SZIMSZJNBQFDAQ-UHFFFAOYSA-N 0.000 description 1
- LIPRKYKMVQPYPG-UHFFFAOYSA-N 3-Hydroxy-2H-pyran-2-one Chemical compound OC1=CC=COC1=O LIPRKYKMVQPYPG-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- AEIVRFFWQSJCAR-UHFFFAOYSA-N 3-benzyl-4-hydroxychromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1CC1=CC=CC=C1 AEIVRFFWQSJCAR-UHFFFAOYSA-N 0.000 description 1
- HNNLFNCNYGQNQW-UHFFFAOYSA-N 3-methyloxiran-2-amine Chemical compound CC1OC1N HNNLFNCNYGQNQW-UHFFFAOYSA-N 0.000 description 1
- YMVOMXCFTDPSOK-UHFFFAOYSA-N 4-(3-chloro-2,2-dimethylpropyl)morpholine Chemical compound ClCC(C)(C)CN1CCOCC1 YMVOMXCFTDPSOK-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
- BOUMJRPCZKXCCV-UHFFFAOYSA-N 4-(4-chlorobutan-2-yl)morpholine Chemical compound ClCCC(C)N1CCOCC1 BOUMJRPCZKXCCV-UHFFFAOYSA-N 0.000 description 1
- KKWQCCPQBCHJBZ-UHFFFAOYSA-N 4-(oxiran-2-ylmethyl)morpholine Chemical compound C1COCCN1CC1CO1 KKWQCCPQBCHJBZ-UHFFFAOYSA-N 0.000 description 1
- KHZAWTVDPWVVBY-UHFFFAOYSA-N 4-hydroxy-3,8-diphenylchromen-2-one Chemical compound O=C1OC=2C(C=3C=CC=CC=3)=CC=CC=2C(O)=C1C1=CC=CC=C1 KHZAWTVDPWVVBY-UHFFFAOYSA-N 0.000 description 1
- CERHCYIDWGTRQA-UHFFFAOYSA-N 4-hydroxy-3-(4-methoxyphenyl)chromen-2-one Chemical compound C1=CC(OC)=CC=C1C1=C(O)C2=CC=CC=C2OC1=O CERHCYIDWGTRQA-UHFFFAOYSA-N 0.000 description 1
- RBZSTMCKGZFSOH-UHFFFAOYSA-N 4-hydroxy-3-methylchromen-2-one Chemical compound C1=CC=C2OC(=O)C(C)=C(O)C2=C1 RBZSTMCKGZFSOH-UHFFFAOYSA-N 0.000 description 1
- FNQCMDNURWRTQE-UHFFFAOYSA-N 4-hydroxy-6-methoxy-3-phenylchromen-2-one Chemical compound OC=1C2=CC(OC)=CC=C2OC(=O)C=1C1=CC=CC=C1 FNQCMDNURWRTQE-UHFFFAOYSA-N 0.000 description 1
- WKRQHVLYIUSJGB-UHFFFAOYSA-N 4-hydroxy-6-methyl-3-phenylchromen-2-one Chemical compound OC=1C2=CC(C)=CC=C2OC(=O)C=1C1=CC=CC=C1 WKRQHVLYIUSJGB-UHFFFAOYSA-N 0.000 description 1
- ZYYUASYTHIXNBR-UHFFFAOYSA-N 4-hydroxy-8-methyl-3-phenylchromen-2-one Chemical compound O=C1OC=2C(C)=CC=CC=2C(O)=C1C1=CC=CC=C1 ZYYUASYTHIXNBR-UHFFFAOYSA-N 0.000 description 1
- SAZHWFFOFMSQPA-UHFFFAOYSA-N 4-phenylcoumarin Chemical compound C12=CC=CC=C2OC(=O)C=C1C1=CC=CC=C1 SAZHWFFOFMSQPA-UHFFFAOYSA-N 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 101100533387 Homo sapiens SCGB1D1 gene Proteins 0.000 description 1
- 206010021143 Hypoxia Diseases 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 102100028659 Secretoglobin family 1D member 1 Human genes 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
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 1
- 206010047141 Vasodilatation Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002431 aminoalkoxy group Chemical group 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940095074 cyclic amp Drugs 0.000 description 1
- UKPBEPCQTDRZSE-UHFFFAOYSA-N cyclizine hydrochloride Chemical compound Cl.C1CN(C)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 UKPBEPCQTDRZSE-UHFFFAOYSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- PTTVRIGSUJQBPB-UHFFFAOYSA-N fluorocyclohexatriene Chemical group FC1=CC=C=C[CH]1 PTTVRIGSUJQBPB-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000007914 intraventricular administration Methods 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ANLMKUQEPXRMGV-UHFFFAOYSA-N n-butyl-n-(3-chloropropyl)butan-1-amine Chemical compound CCCCN(CCCC)CCCCl ANLMKUQEPXRMGV-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 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
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/56—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 without hydrogen atoms in position 3
-
- 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
- C07D311/94—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 condensed with rings other than six-membered or with ring systems containing such rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7605234A FR2368952A1 (fr) | 1976-02-25 | 1976-02-25 | Nouveaux aminoalcoxy-4 (2 h) pyranone-2,3 substitues-5,6 condenses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2707746A1 true DE2707746A1 (de) | 1977-09-01 |
Family
ID=9169581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772707746 Withdrawn DE2707746A1 (de) | 1976-02-25 | 1977-02-23 | 5,6-substituierte, kondensierte 4-(2h)-aminoalkoxy-2,3-pyranone, verfahren zu deren herstellung und sie enthaltende arzneimittel |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4230850A (en:Method) |
| JP (1) | JPS52122371A (en:Method) |
| AR (1) | AR218444A1 (en:Method) |
| AT (1) | AT352720B (en:Method) |
| AU (1) | AU510619B2 (en:Method) |
| BE (1) | BE850522A (en:Method) |
| CA (1) | CA1092112A (en:Method) |
| CH (1) | CH620918A5 (en:Method) |
| CS (1) | CS195325B2 (en:Method) |
| DE (1) | DE2707746A1 (en:Method) |
| DK (1) | DK80777A (en:Method) |
| ES (1) | ES456243A1 (en:Method) |
| FR (1) | FR2368952A1 (en:Method) |
| GB (1) | GB1566491A (en:Method) |
| HU (1) | HU178275B (en:Method) |
| IE (1) | IE44489B1 (en:Method) |
| IL (1) | IL51428A (en:Method) |
| MX (1) | MX4161E (en:Method) |
| NL (1) | NL7702090A (en:Method) |
| NO (1) | NO145841C (en:Method) |
| SE (1) | SE7702041L (en:Method) |
| SU (1) | SU638259A3 (en:Method) |
| YU (1) | YU44977A (en:Method) |
| ZA (1) | ZA77741B (en:Method) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4230850A (en) | 1976-02-25 | 1980-10-28 | Lipha, Lyonnaise Industrielle Pharmaceutique | 3-Substituted-4-aminoalkoxy-5,6-condensed ring-2-pyranones |
| WO2001098288A1 (de) * | 2000-06-19 | 2001-12-27 | Bayer Cropscience Ag | Phenylsubstituierte 5,6-dihydro-pyron-derivate als pestizide und herbizide |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4259327A (en) | 1979-04-02 | 1981-03-31 | Merck & Co., Inc. | Substituted aminoalkoxypyridines, compositions and use thereof |
| DE3209271A1 (de) * | 1982-03-13 | 1983-09-15 | Boehringer Mannheim Gmbh, 6800 Mannheim | Bicyclische phenolether, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
| IL123701A (en) * | 1995-10-13 | 2002-03-10 | Agrevo Uk Ltd | Heterocyclic fungicides and a number of new compounds |
| US7538233B2 (en) | 2003-09-05 | 2009-05-26 | Aventis Pharmaceuticals Inc. | Coumarins as iNOS inhibitors |
| EP3133065A1 (en) | 2015-08-21 | 2017-02-22 | Merck Patent GmbH | Compounds for optically active devices |
| EP3133066A1 (en) * | 2015-08-21 | 2017-02-22 | Merck Patent GmbH | Hydrophilic compounds for optically active devices |
| EP3363793A1 (en) | 2017-02-15 | 2018-08-22 | Merck Patent GmbH | Hydrophobic compounds for optically active devices |
| EP3363786A1 (en) | 2017-02-15 | 2018-08-22 | Merck Patent GmbH | Compounds for optically active devices |
| CN111620848A (zh) * | 2020-04-29 | 2020-09-04 | 华东师范大学 | 含吡喃和中环骨架的三环稠合芳香体系化合物及其合成和应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2368952A1 (fr) | 1976-02-25 | 1978-05-26 | Lipha | Nouveaux aminoalcoxy-4 (2 h) pyranone-2,3 substitues-5,6 condenses |
-
1976
- 1976-02-25 FR FR7605234A patent/FR2368952A1/fr active Granted
-
1977
- 1977-01-19 BE BE174194A patent/BE850522A/xx not_active IP Right Cessation
- 1977-01-24 CH CH84077A patent/CH620918A5/fr not_active IP Right Cessation
- 1977-02-09 CS CS77854A patent/CS195325B2/cs unknown
- 1977-02-09 ZA ZA770741A patent/ZA77741B/xx unknown
- 1977-02-11 IL IL51428A patent/IL51428A/xx unknown
- 1977-02-14 IE IE319/77A patent/IE44489B1/en unknown
- 1977-02-15 CA CA272,042A patent/CA1092112A/en not_active Expired
- 1977-02-18 YU YU00449/77A patent/YU44977A/xx unknown
- 1977-02-18 GB GB7056/77A patent/GB1566491A/en not_active Expired
- 1977-02-21 SU SU772455454A patent/SU638259A3/ru active
- 1977-02-23 DE DE19772707746 patent/DE2707746A1/de not_active Withdrawn
- 1977-02-23 AU AU22556/77A patent/AU510619B2/en not_active Expired
- 1977-02-24 HU HU77LI308A patent/HU178275B/hu unknown
- 1977-02-24 AT AT126277A patent/AT352720B/de not_active IP Right Cessation
- 1977-02-24 MX MX775464U patent/MX4161E/es unknown
- 1977-02-24 DK DK80777A patent/DK80777A/da not_active Application Discontinuation
- 1977-02-24 ES ES456243A patent/ES456243A1/es not_active Expired
- 1977-02-24 NO NO770619A patent/NO145841C/no unknown
- 1977-02-24 SE SE7702041A patent/SE7702041L/xx not_active Application Discontinuation
- 1977-02-25 JP JP1937077A patent/JPS52122371A/ja active Pending
- 1977-02-25 NL NL7702090A patent/NL7702090A/xx not_active Application Discontinuation
- 1977-02-25 AR AR266683A patent/AR218444A1/es active
-
1979
- 1979-03-09 US US06/018,875 patent/US4230850A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4230850A (en) | 1976-02-25 | 1980-10-28 | Lipha, Lyonnaise Industrielle Pharmaceutique | 3-Substituted-4-aminoalkoxy-5,6-condensed ring-2-pyranones |
| WO2001098288A1 (de) * | 2000-06-19 | 2001-12-27 | Bayer Cropscience Ag | Phenylsubstituierte 5,6-dihydro-pyron-derivate als pestizide und herbizide |
Also Published As
| Publication number | Publication date |
|---|---|
| YU44977A (en) | 1982-06-30 |
| FR2368952A1 (fr) | 1978-05-26 |
| BE850522A (fr) | 1977-07-19 |
| HU178275B (en) | 1982-04-28 |
| ATA126277A (de) | 1979-03-15 |
| SE7702041L (sv) | 1977-08-26 |
| AU2255677A (en) | 1978-08-31 |
| GB1566491A (en) | 1980-04-30 |
| NO145841C (no) | 1982-06-09 |
| IL51428A0 (en) | 1977-04-29 |
| IE44489L (en) | 1977-08-25 |
| ES456243A1 (es) | 1978-01-16 |
| NO145841B (no) | 1982-03-01 |
| JPS52122371A (en) | 1977-10-14 |
| AT352720B (de) | 1979-10-10 |
| AU510619B2 (en) | 1980-07-03 |
| IE44489B1 (en) | 1981-12-16 |
| US4230850A (en) | 1980-10-28 |
| IL51428A (en) | 1981-06-29 |
| CA1092112A (en) | 1980-12-23 |
| CS195325B2 (en) | 1980-01-31 |
| CH620918A5 (en:Method) | 1980-12-31 |
| DK80777A (da) | 1977-08-26 |
| MX4161E (es) | 1982-01-14 |
| AR218444A1 (es) | 1980-06-13 |
| ZA77741B (en) | 1977-12-28 |
| FR2368952B1 (en:Method) | 1980-04-30 |
| NL7702090A (nl) | 1977-08-29 |
| SU638259A3 (ru) | 1978-12-15 |
| NO770619L (no) | 1977-08-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0253327B1 (de) | Neue Diphenylpropylamin-Derivate, ihre Herstellung sowie ihre pharmazeutische Verwendung | |
| DE2707746A1 (de) | 5,6-substituierte, kondensierte 4-(2h)-aminoalkoxy-2,3-pyranone, verfahren zu deren herstellung und sie enthaltende arzneimittel | |
| CH506536A (de) | Verfahren zur Herstellung von aromatischen Äthern | |
| EP0075207B1 (de) | Aminopropanolderivate von 2-Hydroxy-beta-phenyl-propiophenonen, Verfahren zu ihrer Herstellung und diese enthaltende therapeutische Mittel | |
| DE2651083C2 (en:Method) | ||
| CH645371A5 (de) | Isochromane, isothiochromane, 2-benzoxepine und 2-benzothiepine. | |
| CH645887A5 (de) | Piperazin-derivate. | |
| DE2123924C3 (en:Method) | ||
| DE2037852A1 (de) | Neue Piperazindenvate und Ver fahren zu ihrer Herstellung | |
| DD145104B3 (de) | Verfahren zur herstellung von polyalkoxyphenylpyrrolidone | |
| DE2351281C3 (de) | Aminophenyl-äthanolamin-Derivate, deren Herstellung und Verwendung | |
| CH510688A (de) | Verfahren zur Herstellung neuer Derivate des 6,11-Dihydro-dibenz(b,e)oxepins | |
| DE2616484C3 (de) | Basische Benzoyläther, deren Salze und quartäre Ammoniumverbindungen sowie Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| EP0000377B1 (de) | Verfahren zur Herstellung von Chromon-Derivaten, neue Chromon-Derivate sowie die Verwendung der neuen Derivate als Pflanzenschutzmittel | |
| EP0027928B1 (de) | Piperidinderivate von 4,5-Dialkyl-3-hydroxy-pyrrol-2-carbonsäureestern, ihre Herstellung und diese enthaltende pharmazeutische Zubereitungen | |
| DE60108354T2 (de) | 2H-1-Benzopyranderivate, Verfahren zu ihrer Herstellung und deren pharmazeutische Zusammensetzungen | |
| DE3223877C2 (en:Method) | ||
| DE2318273A1 (de) | 2,2-disubstituierte benzodioxole | |
| DE3104785A1 (de) | Basische ether der 4-hydroxy-benzophenone, die als (beta)-blocker wirksam sind, und verfahren zu ihrer herstellung | |
| EP0149115A2 (de) | Neue 2-(1-Imidazolyl)-ethanol-Derivate | |
| DE2062129A1 (de) | Neue Chalcon Derivate und Ver fahren zu ihrer Herstellung | |
| DE3328376A1 (de) | Aminopropanolderivate von 2-hydroxy-ss-phenyl-propiophenonen, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE2116213A1 (de) | Piperazinderivate | |
| DE2366224C2 (de) | 1- [3-(l-Äthinyl)- cyclohexyloxy-2-hydroxy] -propyl-4-phenylpiperazin-derivate, deren Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2950064A1 (de) | Piperidinderivate von 3-hydroxythiophen-2-carbonsaeure und -estern, ihre herstellung und diese enthaltende pharmazeutische zubereitungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |