IL31370A - History of coumarin with basic transformation and process for their production - Google Patents
History of coumarin with basic transformation and process for their productionInfo
- Publication number
- IL31370A IL31370A IL31370A IL3137069A IL31370A IL 31370 A IL31370 A IL 31370A IL 31370 A IL31370 A IL 31370A IL 3137069 A IL3137069 A IL 3137069A IL 31370 A IL31370 A IL 31370A
- Authority
- IL
- Israel
- Prior art keywords
- coumarin
- methyl
- dimethoxy
- propyl
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001893 coumarin derivatives Chemical class 0.000 title 1
- 150000004775 coumarins Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 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
- 239000012059 conventional drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- -1 oyano Chemical group 0.000 description 43
- 239000000243 solution Substances 0.000 description 39
- 238000002844 melting Methods 0.000 description 33
- 230000008018 melting Effects 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000007858 starting material Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000001816 cooling Methods 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 229960000956 coumarin Drugs 0.000 description 13
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 235000001671 coumarin Nutrition 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000008280 blood Substances 0.000 description 11
- 210000004369 blood Anatomy 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 9
- 229940086542 triethylamine Drugs 0.000 description 9
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- CHBBSMUTOCUVDW-UHFFFAOYSA-N daphnetin dimethyl ether Natural products C1=CC(=O)OC2=C(OC)C(OC)=CC=C21 CHBBSMUTOCUVDW-UHFFFAOYSA-N 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- KVRKWGMQOATVAE-UHFFFAOYSA-N 7,8-dimethoxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=C(OC)C(OC)=CC=C21 KVRKWGMQOATVAE-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- 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 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- GBYDSYPGGDKWGZ-UHFFFAOYSA-N 6,7-dimethoxy-4-methylchromen-2-one Chemical compound O1C(=O)C=C(C)C2=C1C=C(OC)C(OC)=C2 GBYDSYPGGDKWGZ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- AESFGSJWSUZRGW-UHFFFAOYSA-N (3,4-diacetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=C(OC(C)=O)C(OC(C)=O)=C1 AESFGSJWSUZRGW-UHFFFAOYSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KAZPHAGSWZTKDW-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)propan-2-amine Chemical compound COC1=CC=C(CC(C)N)C=C1OC KAZPHAGSWZTKDW-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- ONIFCGFFEZDWSC-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]piperazine Chemical compound C1=C(OC)C(OC)=CC=C1CN1CCNCC1 ONIFCGFFEZDWSC-UHFFFAOYSA-N 0.000 description 1
- XYXOUBBEZYLFKO-UHFFFAOYSA-N 2,3,4-trimethoxy-n-methyl-n-propan-2-ylaniline Chemical compound COC1=CC=C(N(C)C(C)C)C(OC)=C1OC XYXOUBBEZYLFKO-UHFFFAOYSA-N 0.000 description 1
- VBQGETSLMXRMTB-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)-2-piperazin-1-ylacetamide Chemical compound CC1=CC=CC(C)=C1C(C(N)=O)N1CCNCC1 VBQGETSLMXRMTB-UHFFFAOYSA-N 0.000 description 1
- HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- XFZCLBMMZFSKJT-UHFFFAOYSA-N 2-piperazin-1-yl-n-(3,4,5-trimethoxyphenyl)acetamide Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)CN2CCNCC2)=C1 XFZCLBMMZFSKJT-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XBSMHLZMLQNTLY-UHFFFAOYSA-N 3,4,5-trimethoxy-n-methylaniline Chemical compound CNC1=CC(OC)=C(OC)C(OC)=C1 XBSMHLZMLQNTLY-UHFFFAOYSA-N 0.000 description 1
- WVZUKTGZCDSEAC-UHFFFAOYSA-N 3,4-dimethoxy-n-methyl-n-propan-2-ylaniline Chemical compound COC1=CC=C(N(C)C(C)C)C=C1OC WVZUKTGZCDSEAC-UHFFFAOYSA-N 0.000 description 1
- PGBJWAKHAFOCEL-UHFFFAOYSA-N 3,4-dimethoxy-n-methylaniline Chemical compound CNC1=CC=C(OC)C(OC)=C1 PGBJWAKHAFOCEL-UHFFFAOYSA-N 0.000 description 1
- JXGNMYHBTAZENZ-UHFFFAOYSA-N 3,4-dimethoxychromen-2-one Chemical compound C1=CC=CC2=C1OC(=O)C(OC)=C2OC JXGNMYHBTAZENZ-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
- XCEYKKJMLOFDSS-UHFFFAOYSA-N 4-chloro-n-methylaniline Chemical compound CNC1=CC=C(Cl)C=C1 XCEYKKJMLOFDSS-UHFFFAOYSA-N 0.000 description 1
- JFXDIXYFXDOZIT-UHFFFAOYSA-N 4-methoxy-n-methylaniline Chemical compound CNC1=CC=C(OC)C=C1 JFXDIXYFXDOZIT-UHFFFAOYSA-N 0.000 description 1
- WFSKVHPOKPQJSU-UHFFFAOYSA-N 5,7-dimethoxy-4-methyl-1-benzopyran-2-one Chemical compound CC1=CC(=O)OC2=CC(OC)=CC(OC)=C21 WFSKVHPOKPQJSU-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- VCLGIEGDPDKRDU-UHFFFAOYSA-N 7,8-dimethoxy-3-methylchromen-2-one Chemical compound CC=1C(OC2=C(C(=CC=C2C1)OC)OC)=O VCLGIEGDPDKRDU-UHFFFAOYSA-N 0.000 description 1
- CKSRQDSVNLXONV-UHFFFAOYSA-N 7,8-dimethoxy-4-phenylchromen-2-one Chemical compound C=1C(=O)OC2=C(OC)C(OC)=CC=C2C=1C1=CC=CC=C1 CKSRQDSVNLXONV-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- UHWVSEOVJBQKBE-UHFFFAOYSA-N Trimetazidine Chemical compound COC1=C(OC)C(OC)=CC=C1CN1CCNCC1 UHWVSEOVJBQKBE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001727 carbonic acid monoesters Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- NXJCRELRQHZBQA-UHFFFAOYSA-N citropten Natural products C1=CC(=O)OC2=CC(OC)=CC(OC)=C21 NXJCRELRQHZBQA-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- HQCYVSPJIOJEGA-UHFFFAOYSA-N methoxycoumarin Natural products C1=CC=C2OC(=O)C(OC)=CC2=C1 HQCYVSPJIOJEGA-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical class CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- AAFDMAAXSJVSCP-UHFFFAOYSA-N n-methyl-2-(2,3,4-trimethoxyphenyl)ethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1OC AAFDMAAXSJVSCP-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- GUAFOGOEJLSQBT-UHFFFAOYSA-N scoparone Chemical class C1=CC(=O)OC2=C1C=C(OC)C(OC)=C2 GUAFOGOEJLSQBT-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 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
- C07D311/04—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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681668877 DE1668877C3 (de) | 1968-01-19 | 1968-01-19 | Basisch substituierte Cumarinderivate und deren pharmakologisch verträgliche Salze und Verfahren zu deren Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31370A0 IL31370A0 (en) | 1969-03-27 |
| IL31370A true IL31370A (en) | 1973-05-31 |
Family
ID=5686145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31370A IL31370A (en) | 1968-01-19 | 1969-01-06 | History of coumarin with basic transformation and process for their production |
Country Status (9)
| Country | Link |
|---|---|
| AT (2) | AT279604B (cs) |
| BR (1) | BR6905654D0 (cs) |
| CH (1) | CH507932A (cs) |
| CS (2) | CS154607B2 (cs) |
| DK (2) | DK122608B (cs) |
| ES (2) | ES362656A1 (cs) |
| IL (1) | IL31370A (cs) |
| NO (1) | NO126227B (cs) |
| RO (1) | RO56654A (cs) |
-
1969
- 1969-01-06 IL IL31370A patent/IL31370A/en unknown
- 1969-01-14 CS CS21169*#A patent/CS154607B2/cs unknown
- 1969-01-14 CS CS21269*#A patent/CS154608B2/cs unknown
- 1969-01-17 BR BR205654/69A patent/BR6905654D0/pt unknown
- 1969-01-17 CH CH66669A patent/CH507932A/de not_active IP Right Cessation
- 1969-01-17 DK DK28569AA patent/DK122608B/da unknown
- 1969-01-17 DK DK28069AA patent/DK121659B/da unknown
- 1969-01-17 AT AT49469A patent/AT279604B/de not_active IP Right Cessation
- 1969-01-17 AT AT49369A patent/AT279603B/de not_active IP Right Cessation
- 1969-01-18 RO RO58794A patent/RO56654A/ro unknown
- 1969-01-18 ES ES362656A patent/ES362656A1/es not_active Expired
- 1969-01-18 ES ES362657A patent/ES362657A1/es not_active Expired
- 1969-01-18 NO NO00203/69A patent/NO126227B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS154608B2 (cs) | 1974-04-30 |
| ES362657A1 (es) | 1970-11-16 |
| DK122608B (da) | 1972-03-20 |
| AT279604B (de) | 1970-03-10 |
| IL31370A0 (en) | 1969-03-27 |
| NO126227B (cs) | 1973-01-08 |
| RO56654A (cs) | 1975-01-15 |
| ES362656A1 (es) | 1970-09-01 |
| AT279603B (de) | 1970-03-10 |
| CH507932A (de) | 1971-05-31 |
| DK121659B (da) | 1971-11-15 |
| CS154607B2 (cs) | 1974-04-30 |
| BR6905654D0 (pt) | 1973-02-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1060445A (en) | Process for preparing quinazoline derivatives | |
| US20020132821A1 (en) | Novel heteroaryl derivatives and their use as medicaments | |
| US4868303A (en) | Bis-dioxopiperazine derivatives | |
| US3652557A (en) | 3-(gamma-tertiary amino-beta-alkoxy benzoyloxy-propyl) - 4 -hydrocarbon - 5 8 - alkoxy coumarins | |
| US3541097A (en) | Process for the production of coumarin derivatives | |
| US3959281A (en) | Piperazino substituted coumarin derivatives | |
| EP0361577B1 (en) | Tetrahydronaphthalene and indane derivatives | |
| IL31370A (en) | History of coumarin with basic transformation and process for their production | |
| US4268511A (en) | 3-Amino(1H,3H)quinazoline-2,4-dione derivatives and their therapeutic applications | |
| US3943172A (en) | Derivatives of 2-amino-(1,2,3,4-tetrahydronaphthalene), the preparation and use thereof | |
| US3562276A (en) | Diarylcyclopropane piperazides possessing enhanced antihistaminic,antiserotoninic and antiexudative activity | |
| US3509141A (en) | 2-amino-quinazolines | |
| US4118494A (en) | Substituted 3,4-dihydro-2H-isoquinolin-1-thiones | |
| US3647802A (en) | 2-amino-4-aryl-3 4-dihydroquinolines | |
| US3732251A (en) | Basically substituted coumarin compounds | |
| US3946018A (en) | 1,4-Dihydro-3 (2H)-isoquinolinone derivatives | |
| US3981872A (en) | Derivatives of 2-amino-(1,2,3,4-tetrahydronaphthalene) | |
| US4387102A (en) | 4-(N-(3',4'-Methylenedioxybenzylidene)-aminomethyl)cyclohexane-1-carboxylic acid and derivatives thereof and pharmaceutical composition thereof | |
| US2951849A (en) | Hydrazine derivatives | |
| US3726902A (en) | Furfuryl amino-coumarins | |
| US3738985A (en) | Certain 3-(3-amino-2-benzoyloxypropyl)-4(3h)-quinazolinones | |
| EP0165592A2 (en) | Antitumor agents | |
| EP0602458A1 (en) | 1,4-Benzoxazine derivatives | |
| SU566521A3 (ru) | Способ получени лактамов | |
| Vargha et al. | Synthesis and pharmacological investigation of new alkoxybenzamides—I: 3: 4: 5-Trimethoxybenzamides |