DE2108185A1 - N-(3-aminoalkyl-2-oxo-2h-1-benzopyran-7-yl) ureas - as coronary vasodilators - Google Patents
N-(3-aminoalkyl-2-oxo-2h-1-benzopyran-7-yl) ureas - as coronary vasodilatorsInfo
- Publication number
- DE2108185A1 DE2108185A1 DE19712108185 DE2108185A DE2108185A1 DE 2108185 A1 DE2108185 A1 DE 2108185A1 DE 19712108185 DE19712108185 DE 19712108185 DE 2108185 A DE2108185 A DE 2108185A DE 2108185 A1 DE2108185 A1 DE 2108185A1
- Authority
- DE
- Germany
- Prior art keywords
- oxo
- benzopyran
- general formula
- compounds
- methyl
- 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.)
- Ceased
Links
- 239000003218 coronary vasodilator agent Substances 0.000 title abstract 2
- 235000013877 carbamide Nutrition 0.000 title 1
- 150000003672 ureas Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000001893 coumarin derivatives Chemical class 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- -1 R7 is H Chemical group 0.000 abstract description 70
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 40
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
- 238000000354 decomposition reaction Methods 0.000 description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- BVXGJMKPMTXSFM-UHFFFAOYSA-N n-[4-methyl-3-(2-morpholin-4-ylethyl)-2-oxochromen-7-yl]morpholine-4-carboxamide Chemical compound O=C1OC=2C=C(NC(=O)N3CCOCC3)C=CC=2C(C)=C1CCN1CCOCC1 BVXGJMKPMTXSFM-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- XTMYWKVPXFPZRJ-UHFFFAOYSA-N CC1=C2OC(=O)C(CCCl)=C(C)C2=CC=C1NC(=O)OC1=CC=CC=C1 Chemical compound CC1=C2OC(=O)C(CCCl)=C(C)C2=CC=C1NC(=O)OC1=CC=CC=C1 XTMYWKVPXFPZRJ-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- QDLQALCWBCVPPE-UHFFFAOYSA-N CC(C(O1)=C(C=C2)C(C)=C(CCN3CCOCC3)C1=O)=C2NC(N1CCOCC1)=O Chemical compound CC(C(O1)=C(C=C2)C(C)=C(CCN3CCOCC3)C1=O)=C2NC(N1CCOCC1)=O QDLQALCWBCVPPE-UHFFFAOYSA-N 0.000 description 4
- WIWCCDXIXWASME-UHFFFAOYSA-N CC1=C(CCCl)C(=O)OC2=CC(NC(=O)OC3=CC=CC=C3)=CC=C12 Chemical compound CC1=C(CCCl)C(=O)OC2=CC(NC(=O)OC3=CC=CC=C3)=CC=C12 WIWCCDXIXWASME-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000007056 transamidation reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 3
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- QFBCEVKHKOTVIC-UHFFFAOYSA-N 3-[3-[2-(diethylamino)ethyl]-4-methyl-2-oxochromen-7-yl]-1,1-diethylurea Chemical compound C(C)N(CCC=1C(OC2=C(C1C)C=CC(=C2)NC(=O)N(CC)CC)=O)CC QFBCEVKHKOTVIC-UHFFFAOYSA-N 0.000 description 2
- ISJOXUCASVJHJG-UHFFFAOYSA-N CC1CN(CCO1)C(=O)NC2=CC3=C(C=C2)C(=C(C(=O)O3)CCN4CCOCC4)C Chemical compound CC1CN(CCO1)C(=O)NC2=CC3=C(C=C2)C(=C(C(=O)O3)CCN4CCOCC4)C ISJOXUCASVJHJG-UHFFFAOYSA-N 0.000 description 2
- VHTIILDAEFBVHW-UHFFFAOYSA-N CCN(CC)C(NC(C=C1)=C(C)C(O2)=C1C(C)=C(CCN1CCOCC1)C2=O)=O Chemical compound CCN(CC)C(NC(C=C1)=C(C)C(O2)=C1C(C)=C(CCN1CCOCC1)C2=O)=O VHTIILDAEFBVHW-UHFFFAOYSA-N 0.000 description 2
- RMTPLVRAKACWFI-UHFFFAOYSA-N CCOC(NC(C=C1)=CC(O2)=C1C(C)=C(CC(CCl)O)C2=O)=O Chemical compound CCOC(NC(C=C1)=CC(O2)=C1C(C)=C(CC(CCl)O)C2=O)=O RMTPLVRAKACWFI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000003113 alkalizing effect Effects 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 210000003748 coronary sinus Anatomy 0.000 description 2
- 150000004775 coumarins Chemical class 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- WLBGIVZZFISEJL-UHFFFAOYSA-N tert-butyl 4-[1-(2-ethoxyethyl)benzimidazol-2-yl]piperidine-1-carboxylate Chemical compound N=1C2=CC=CC=C2N(CCOCC)C=1C1CCN(C(=O)OC(C)(C)C)CC1 WLBGIVZZFISEJL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- VANKGBSIIPOCOW-UHFFFAOYSA-N 1,1-diethyl-3-[3-(2-morpholin-4-ylethyl)-2-oxochromen-7-yl]urea Chemical compound O1CCN(CC1)CCC=1C(OC2=C(C1)C=CC(=C2)NC(=O)N(CC)CC)=O VANKGBSIIPOCOW-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- IUXYVKZUDNLISR-UHFFFAOYSA-N 2-(tert-butylamino)ethanol Chemical compound CC(C)(C)NCCO IUXYVKZUDNLISR-UHFFFAOYSA-N 0.000 description 1
- CLAHOZSYMRNIPY-UHFFFAOYSA-N 2-hydroxyethylurea Chemical compound NC(=O)NCCO CLAHOZSYMRNIPY-UHFFFAOYSA-N 0.000 description 1
- VHEYHMGSWDZXEN-UHFFFAOYSA-N 2-hydroxypropylurea Chemical compound CC(O)CNC(N)=O VHEYHMGSWDZXEN-UHFFFAOYSA-N 0.000 description 1
- LQMMFVPUIVBYII-UHFFFAOYSA-N 2-methylmorpholine Chemical compound CC1CNCCO1 LQMMFVPUIVBYII-UHFFFAOYSA-N 0.000 description 1
- PYJMSQYUXIZLEW-UHFFFAOYSA-N 4-methyl-7-(methylamino)-3-(2-morpholin-4-ylethyl)chromen-2-one Chemical compound CNC1=CC2=C(C(=C(C(O2)=O)CCN2CCOCC2)C)C=C1 PYJMSQYUXIZLEW-UHFFFAOYSA-N 0.000 description 1
- XTYCVTZXVJSQRU-UHFFFAOYSA-N CC(C(C=CC(NC(N1CCCC1)=O)=C1)=C1O1)=C(CCN2CCCC2)C1=O Chemical compound CC(C(C=CC(NC(N1CCCC1)=O)=C1)=C1O1)=C(CCN2CCCC2)C1=O XTYCVTZXVJSQRU-UHFFFAOYSA-N 0.000 description 1
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- LWEBWYWSRLVHBK-UHFFFAOYSA-N O1CCN(CC1)CCC=1C(OC2=C(C1C)C=CC(=C2)NC(=O)N(CCO)CCO)=O Chemical compound O1CCN(CC1)CCC=1C(OC2=C(C1C)C=CC(=C2)NC(=O)N(CCO)CCO)=O LWEBWYWSRLVHBK-UHFFFAOYSA-N 0.000 description 1
- YPUOKZKDJPFIHF-UHFFFAOYSA-N O1CCN(CC1)CCC=1C(OC2=C(C1C)C=CC(=C2)NC(=O)N)=O Chemical compound O1CCN(CC1)CCC=1C(OC2=C(C1C)C=CC(=C2)NC(=O)N)=O YPUOKZKDJPFIHF-UHFFFAOYSA-N 0.000 description 1
- XPDLLMMLTADRKZ-UHFFFAOYSA-N O1CCN(CC1)CCC=1C(OC2=C(C1C)C=CC(=C2)NC(=O)NC2=CC=CC=C2)=O Chemical compound O1CCN(CC1)CCC=1C(OC2=C(C1C)C=CC(=C2)NC(=O)NC2=CC=CC=C2)=O XPDLLMMLTADRKZ-UHFFFAOYSA-N 0.000 description 1
- WZUXYWHBLIJABT-UHFFFAOYSA-N O1CCN(CC1)CCC=1C(OC2=C(C1C)C=CC(=C2)NC(=O)NC2CCCCC2)=O Chemical compound O1CCN(CC1)CCC=1C(OC2=C(C1C)C=CC(=C2)NC(=O)NC2CCCCC2)=O WZUXYWHBLIJABT-UHFFFAOYSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- ISXIAPAMEMYUQB-UHFFFAOYSA-N n-[3-(2-hydroxy-3-morpholin-4-ylpropyl)-4-methyl-2-oxochromen-7-yl]morpholine-4-carboxamide Chemical compound O=C1OC=2C=C(NC(=O)N3CCOCC3)C=CC=2C(C)=C1CC(O)CN1CCOCC1 ISXIAPAMEMYUQB-UHFFFAOYSA-N 0.000 description 1
- GRRYSIXDUIAUGY-UHFFFAOYSA-N n-methylcarbamoyl chloride Chemical compound CNC(Cl)=O GRRYSIXDUIAUGY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone 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
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 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
- C07D311/04—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
- C07D311/18—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 otherwise than in position 3 or 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712108185 DE2108185A1 (en) | 1971-02-20 | 1971-02-20 | N-(3-aminoalkyl-2-oxo-2h-1-benzopyran-7-yl) ureas - as coronary vasodilators |
| IL37284A IL37284A (en) | 1970-07-17 | 1971-07-09 | 3-aminoalkyl-7-ureido coumarine derivatives,their preparation and pharmaceutical compositions containing them |
| AU31087/71A AU459412B2 (en) | 1970-07-17 | 1971-07-12 | New coumarine derivatives effective as coronary dilatators and process for their manufacture |
| YU1842/71A YU34693B (en) | 1970-07-17 | 1971-07-13 | Process for obtaining coumarin derivatives |
| RO67645A RO59060A (enrdf_load_stackoverflow) | 1970-07-17 | 1971-07-13 | |
| BE769959A BE769959A (fr) | 1970-07-17 | 1971-07-13 | Nouveaux derives de la coumarine doues d'une activite coronaro-dilatatrice et leur procede de preparation |
| SU1817948A SU433678A3 (enrdf_load_stackoverflow) | 1970-07-17 | 1971-07-14 | |
| SU1684054A SU402211A3 (enrdf_load_stackoverflow) | 1971-02-20 | 1971-07-14 | |
| SU1740383A SU404237A1 (ru) | 1971-07-14 | Способ получения производных кумарина | |
| SU1817946A SU461494A3 (ru) | 1971-02-20 | 1971-07-14 | Способ получени производных кумарина |
| FI2008/71A FI54117C (fi) | 1970-07-17 | 1971-07-15 | Foerfarande foer framstaellning av nya koronardilatatoriskt verkande substituerade 7-ureidocumarinderivat |
| SE7109185A SE379541B (enrdf_load_stackoverflow) | 1970-07-17 | 1971-07-15 | |
| CS5229A CS172355B2 (enrdf_load_stackoverflow) | 1970-07-17 | 1971-07-15 | |
| ES393295A ES393295A1 (es) | 1970-07-17 | 1971-07-15 | Procedimiento para la preparacion de derivados de cumarina de efecto dilatador de la coronaria. |
| OA54307A OA03762A (fr) | 1970-07-17 | 1971-07-16 | Nouveaux dérivés de la coumarine et leur procédé de préparation. |
| AT588472A AT312593B (de) | 1971-02-20 | 1971-07-16 | Verfahren zur Herstellung neuer Cumarinderivate und ihrer Salze |
| CA118,427A CA960669A (en) | 1970-07-17 | 1971-07-16 | Coumarine derivatives effective as coronary dilatators and process for their preparation |
| CH781274A CH564006A5 (enrdf_load_stackoverflow) | 1970-07-17 | 1971-07-16 | |
| PL1971179895A PL91812B1 (enrdf_load_stackoverflow) | 1970-07-17 | 1971-07-16 | |
| FR7126098A FR2100927B1 (enrdf_load_stackoverflow) | 1970-07-17 | 1971-07-16 | |
| NL7109845A NL7109845A (enrdf_load_stackoverflow) | 1970-07-17 | 1971-07-16 | |
| DK352971AA DK125919B (da) | 1970-07-17 | 1971-07-16 | Analogifremgangsmåde til fremstilling af koronardilatatorisk aktive cumarinderivater eller syreadditionssalte deraf. |
| GB3352571A GB1323179A (en) | 1970-07-17 | 1971-07-16 | Coumarin derivatives |
| CH781074A CH563385A5 (enrdf_load_stackoverflow) | 1970-07-17 | 1971-07-16 | |
| PL1971149495A PL84518B1 (enrdf_load_stackoverflow) | 1971-02-20 | 1971-07-16 | |
| CH1053971A CH563384A5 (enrdf_load_stackoverflow) | 1970-07-17 | 1971-07-16 | |
| AT623371A AT308090B (de) | 1970-07-17 | 1971-07-16 | Verfahren zur Herstellung neuer Cumarinderivate und ihrer Salze |
| CH781174A CH563386A5 (enrdf_load_stackoverflow) | 1970-07-17 | 1971-07-16 | |
| US163110*[A US3897426A (en) | 1970-07-17 | 1972-07-15 | 1-(3-(AMINO ALKYL)-2-OXO-2H-1-benzopyran-7-yl)-ureas |
| US450925A US3930003A (en) | 1970-07-17 | 1974-03-13 | Coumarine derivatives and process for the preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712108185 DE2108185A1 (en) | 1971-02-20 | 1971-02-20 | N-(3-aminoalkyl-2-oxo-2h-1-benzopyran-7-yl) ureas - as coronary vasodilators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2108185A1 true DE2108185A1 (en) | 1972-09-07 |
Family
ID=5799358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712108185 Ceased DE2108185A1 (en) | 1970-07-17 | 1971-02-20 | N-(3-aminoalkyl-2-oxo-2h-1-benzopyran-7-yl) ureas - as coronary vasodilators |
Country Status (4)
| Country | Link |
|---|---|
| AT (1) | AT312593B (enrdf_load_stackoverflow) |
| DE (1) | DE2108185A1 (enrdf_load_stackoverflow) |
| PL (1) | PL84518B1 (enrdf_load_stackoverflow) |
| SU (2) | SU461494A3 (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4452811A (en) * | 1977-11-17 | 1984-06-05 | Fidia S.P.A. | Monohalogenated derivatives of 7-hydroxy-coumarin, pharmaceutical compositions containing the same and methods of using said compositions |
| WO1994008985A1 (de) * | 1992-10-08 | 1994-04-28 | Dr. Willmar Schwabe Gmbh & Co. | Neue benzopyranone, verfahren zu ihrer herstellung und verwendung |
| WO2001021577A3 (en) * | 1999-09-20 | 2001-10-04 | Takeda Chemical Industries Ltd | Melanin concentrating hormone antagonist |
-
1971
- 1971-02-20 DE DE19712108185 patent/DE2108185A1/de not_active Ceased
- 1971-07-14 SU SU1817946A patent/SU461494A3/ru active
- 1971-07-14 SU SU1684054A patent/SU402211A3/ru active
- 1971-07-16 PL PL1971149495A patent/PL84518B1/pl unknown
- 1971-07-16 AT AT588472A patent/AT312593B/de not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4452811A (en) * | 1977-11-17 | 1984-06-05 | Fidia S.P.A. | Monohalogenated derivatives of 7-hydroxy-coumarin, pharmaceutical compositions containing the same and methods of using said compositions |
| WO1994008985A1 (de) * | 1992-10-08 | 1994-04-28 | Dr. Willmar Schwabe Gmbh & Co. | Neue benzopyranone, verfahren zu ihrer herstellung und verwendung |
| WO2001021577A3 (en) * | 1999-09-20 | 2001-10-04 | Takeda Chemical Industries Ltd | Melanin concentrating hormone antagonist |
| US7115750B1 (en) | 1999-09-20 | 2006-10-03 | Takeda Pharmaceutical Company Limited | Melanin concentrating hormone antagonist |
Also Published As
| Publication number | Publication date |
|---|---|
| AT312593B (de) | 1974-01-10 |
| SU402211A3 (enrdf_load_stackoverflow) | 1973-10-12 |
| SU461494A3 (ru) | 1975-02-25 |
| PL84518B1 (enrdf_load_stackoverflow) | 1976-04-30 |
| SU404237A3 (enrdf_load_stackoverflow) | 1973-10-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8131 | Rejection |