FI66601C - Foerfarande foer framstaellning av terapeutiskt aktiva 1,3-disubstituerade urinaemnen eller 2-tiourinaemnen - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiva 1,3-disubstituerade urinaemnen eller 2-tiourinaemnen Download PDFInfo
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- FI66601C FI66601C FI780384A FI780384A FI66601C FI 66601 C FI66601 C FI 66601C FI 780384 A FI780384 A FI 780384A FI 780384 A FI780384 A FI 780384A FI 66601 C FI66601 C FI 66601C
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- Finland
- Prior art keywords
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- theory
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- urea
- compound
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- 230000001225 therapeutic effect Effects 0.000 title 2
- 230000004913 activation Effects 0.000 title 1
- 238000000034 method Methods 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- -1 1,3-disubstituted urea Chemical class 0.000 claims description 27
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- 150000003951 lactams Chemical class 0.000 claims description 17
- 239000004202 carbamide Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052717 sulfur Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 210000002700 urine Anatomy 0.000 claims description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 115
- 238000002329 infrared spectrum Methods 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 41
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- 238000004458 analytical method Methods 0.000 description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 235000013877 carbamide Nutrition 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- WQKVZVGKZZWLPJ-UHFFFAOYSA-N 1-(aminomethyl)pyrrolidin-2-one Chemical compound NCN1CCCC1=O WQKVZVGKZZWLPJ-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 8
- 229960004526 piracetam Drugs 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 206010021143 Hypoxia Diseases 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 238000001356 surgical procedure Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- GXFZCDMWGMFGFL-KKXMJGKMSA-N (+)-Tubocurarine chloride hydrochloride Chemical class [Cl-].[Cl-].C([C@H]1[N+](C)(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CC[NH+]3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 GXFZCDMWGMFGFL-KKXMJGKMSA-N 0.000 description 3
- XARZOTHWWZADRR-UHFFFAOYSA-N 1,3-bis[(2-oxopyrrolidin-1-yl)methyl]thiourea Chemical compound O=C1CCCN1CNC(=S)NCN1C(=O)CCC1 XARZOTHWWZADRR-UHFFFAOYSA-N 0.000 description 3
- HJORCZCMNWLHMB-UHFFFAOYSA-N 1-(3-aminopropyl)pyrrolidin-2-one Chemical compound NCCCN1CCCC1=O HJORCZCMNWLHMB-UHFFFAOYSA-N 0.000 description 3
- 241001111317 Chondrodendron tomentosum Species 0.000 description 3
- 239000008709 Curare Substances 0.000 description 3
- 241000906446 Theraps Species 0.000 description 3
- 230000016571 aggressive behavior Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000005915 ammonolysis reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- WMKONRFEZGAHTE-UHFFFAOYSA-N imuracetam Chemical compound C1CCC(=O)N1CNC(=O)NCN1CCCC1=O WMKONRFEZGAHTE-UHFFFAOYSA-N 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- QJALZHVODOFBOP-UHFFFAOYSA-N 1,3-bis(1-hydroxyethyl)urea Chemical compound CC(O)NC(=O)NC(C)O QJALZHVODOFBOP-UHFFFAOYSA-N 0.000 description 2
- ORGWCTHQVYSUNL-UHFFFAOYSA-N 1,3-bis(hydroxymethyl)thiourea Chemical compound OCNC(=S)NCO ORGWCTHQVYSUNL-UHFFFAOYSA-N 0.000 description 2
- OUHLLHUYCDWKKI-UHFFFAOYSA-N 1,3-bis[1-(2-oxopyrrolidin-1-yl)ethyl]urea Chemical compound C1CCC(=O)N1C(C)NC(=O)NC(C)N1CCCC1=O OUHLLHUYCDWKKI-UHFFFAOYSA-N 0.000 description 2
- HHEKNWQXFVOUNJ-UHFFFAOYSA-N 1-(2-aminoethyl)pyrrolidin-2-one Chemical compound NCCN1CCCC1=O HHEKNWQXFVOUNJ-UHFFFAOYSA-N 0.000 description 2
- KBEXMYGNYVFNAS-UHFFFAOYSA-N 1-(aminomethyl)-5-(4-chlorophenyl)piperidin-2-one Chemical compound C1CC(=O)N(CN)CC1C1=CC=C(Cl)C=C1 KBEXMYGNYVFNAS-UHFFFAOYSA-N 0.000 description 2
- XPKLUGCOPFSHFT-UHFFFAOYSA-N 1-(aminomethyl)-5-phenylpyrrolidin-2-one Chemical compound C1CC(=O)N(CN)C1C1=CC=CC=C1 XPKLUGCOPFSHFT-UHFFFAOYSA-N 0.000 description 2
- HFYLXSOTOINXLE-UHFFFAOYSA-N 1-(aminomethyl)azonan-2-one Chemical compound NCN1CCCCCCCC1=O HFYLXSOTOINXLE-UHFFFAOYSA-N 0.000 description 2
- WAFMOUFRJOGUMW-UHFFFAOYSA-N 1-(chloromethyl)piperidin-2-one Chemical compound ClCN1CCCCC1=O WAFMOUFRJOGUMW-UHFFFAOYSA-N 0.000 description 2
- LEYRRKPTVVUCIC-UHFFFAOYSA-N 1-(hydroxymethyl)piperidin-2-one Chemical compound OCN1CCCCC1=O LEYRRKPTVVUCIC-UHFFFAOYSA-N 0.000 description 2
- PJEXUIKBGBSHBS-UHFFFAOYSA-N 1-(hydroxymethyl)pyrrolidin-2-one Chemical compound OCN1CCCC1=O PJEXUIKBGBSHBS-UHFFFAOYSA-N 0.000 description 2
- NLCGXPCFESDVLA-UHFFFAOYSA-N 1-[(2-oxopyrrolidin-1-yl)methyl]-3-[3-(2-oxopyrrolidin-1-yl)propyl]urea Chemical compound C1CCC(=O)N1CNC(=O)NCCCN1CCCC1=O NLCGXPCFESDVLA-UHFFFAOYSA-N 0.000 description 2
- 206010001488 Aggression Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 208000026139 Memory disease Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- WLDBKDYSWDAYMZ-UHFFFAOYSA-N decan-1-one Chemical compound CCCCCCCCC[C]=O WLDBKDYSWDAYMZ-UHFFFAOYSA-N 0.000 description 2
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 231100000053 low toxicity Toxicity 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
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- VCBSMHZNRBWEIJ-UHFFFAOYSA-L trimethyl-[5-[5-(trimethylazaniumyl)pentoxy]pentyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C[N+](C)(C)CCCCCOCCCCC[N+](C)(C)C VCBSMHZNRBWEIJ-UHFFFAOYSA-L 0.000 description 2
- XQMSLBOUBMUBKU-UHFFFAOYSA-N 1,3-bis[(2,2,4-trimethyl-5-oxopyrrolidin-1-yl)methyl]urea Chemical compound O=C1C(C)CC(C)(C)N1CNC(=O)NCN1C(C)(C)CC(C)C1=O XQMSLBOUBMUBKU-UHFFFAOYSA-N 0.000 description 1
- QLPXGRFXPJVBHS-UHFFFAOYSA-N 1,3-bis[(2,3-dimethyl-5-oxopyrrolidin-1-yl)methyl]urea Chemical compound CC1C(C)CC(=O)N1CNC(=O)NCN1C(=O)CC(C)C1C QLPXGRFXPJVBHS-UHFFFAOYSA-N 0.000 description 1
- DPGSBVPDQHLJHD-UHFFFAOYSA-N 1,3-bis[(2-oxo-4-phenylpyrrolidin-1-yl)methyl]urea Chemical compound C1C(C=2C=CC=CC=2)CC(=O)N1CNC(=O)NCN(C(C1)=O)CC1C1=CC=CC=C1 DPGSBVPDQHLJHD-UHFFFAOYSA-N 0.000 description 1
- ZUFZXICJBMVRKD-UHFFFAOYSA-N 1,3-bis[(2-oxo-5-phenylpyrrolidin-1-yl)methyl]urea Chemical compound C=1C=CC=CC=1C1CCC(=O)N1CNC(=O)NCN(C(CC1)=O)C1C1=CC=CC=C1 ZUFZXICJBMVRKD-UHFFFAOYSA-N 0.000 description 1
- WRYUGNZZENMDJG-UHFFFAOYSA-N 1,3-bis[(2-oxoazepan-1-yl)methyl]thiourea Chemical compound O=C1CCCCCN1CNC(=S)NCN1C(=O)CCCCC1 WRYUGNZZENMDJG-UHFFFAOYSA-N 0.000 description 1
- ICRVMICNMBTAEK-UHFFFAOYSA-N 1,3-bis[(2-oxoazepan-1-yl)methyl]urea Chemical compound C1CCCCC(=O)N1CNC(=O)NCN1CCCCCC1=O ICRVMICNMBTAEK-UHFFFAOYSA-N 0.000 description 1
- DSUSATXHHXYORL-UHFFFAOYSA-N 1,3-bis[(2-oxoazonan-1-yl)methyl]urea Chemical compound C1CCCCCCC(=O)N1CNC(=O)NCN1CCCCCCCC1=O DSUSATXHHXYORL-UHFFFAOYSA-N 0.000 description 1
- PXHSROUTNMWQNJ-UHFFFAOYSA-N 1,3-bis[(2-oxopyrrolidin-1-yl)-phenylmethyl]urea Chemical compound C1CCC(=O)N1C(C=1C=CC=CC=1)NC(=O)NC(C=1C=CC=CC=1)N1CCCC1=O PXHSROUTNMWQNJ-UHFFFAOYSA-N 0.000 description 1
- IBVZQJPVEOFKHO-UHFFFAOYSA-N 1,3-bis[(3-butyl-2-oxopyrrolidin-1-yl)methyl]thiourea Chemical compound O=C1C(CCCC)CCN1CNC(=S)NCN1C(=O)C(CCCC)CC1 IBVZQJPVEOFKHO-UHFFFAOYSA-N 0.000 description 1
- SOAQIGVIHVAGKF-UHFFFAOYSA-N 1,3-bis[(3-butyl-2-oxopyrrolidin-1-yl)methyl]urea Chemical compound O=C1C(CCCC)CCN1CNC(=O)NCN1C(=O)C(CCCC)CC1 SOAQIGVIHVAGKF-UHFFFAOYSA-N 0.000 description 1
- KXTXINWTOPWGGW-UHFFFAOYSA-N 1,3-bis[(3-methyl-1-oxo-2-azaspiro[4.5]decan-2-yl)methyl]urea Chemical compound O=C1N(CNC(=O)NCN2C(C3(CCCCC3)CC2C)=O)C(C)CC21CCCCC2 KXTXINWTOPWGGW-UHFFFAOYSA-N 0.000 description 1
- YLXSWIVCIFVKDS-UHFFFAOYSA-N 1,3-bis[1-(2-oxopyrrolidin-1-yl)propyl]urea Chemical compound C1CCC(=O)N1C(CC)NC(=O)NC(CC)N1CCCC1=O YLXSWIVCIFVKDS-UHFFFAOYSA-N 0.000 description 1
- LPHJXXWMYVCPLR-UHFFFAOYSA-N 1,3-bis[2-(2-oxopyrrolidin-1-yl)butyl]urea Chemical compound C1CCC(=O)N1C(CC)CNC(=O)NCC(CC)N1CCCC1=O LPHJXXWMYVCPLR-UHFFFAOYSA-N 0.000 description 1
- WIQYMFJZMVQEQA-UHFFFAOYSA-N 1,3-bis[2-(2-oxopyrrolidin-1-yl)ethyl]urea Chemical compound C1CCC(=O)N1CCNC(=O)NCCN1CCCC1=O WIQYMFJZMVQEQA-UHFFFAOYSA-N 0.000 description 1
- OHFOUMYXQHGLLF-UHFFFAOYSA-N 1,3-bis[2-(2-oxopyrrolidin-1-yl)propyl]urea Chemical compound C1CCC(=O)N1C(C)CNC(=O)NCC(C)N1CCCC1=O OHFOUMYXQHGLLF-UHFFFAOYSA-N 0.000 description 1
- MZMAQHAMJMKKHQ-UHFFFAOYSA-N 1,3-bis[3-(2-oxopyrrolidin-1-yl)propyl]urea Chemical compound C1CCC(=O)N1CCCNC(=O)NCCCN1CCCC1=O MZMAQHAMJMKKHQ-UHFFFAOYSA-N 0.000 description 1
- QHTRKNSEUBMHBM-UHFFFAOYSA-N 1,3-bis[[4-(4-chlorophenyl)-3-methyl-2-oxopyrrolidin-1-yl]methyl]urea Chemical compound O=C1C(C)C(C=2C=CC(Cl)=CC=2)CN1CNC(=O)NCN(C(C1C)=O)CC1C1=CC=C(Cl)C=C1 QHTRKNSEUBMHBM-UHFFFAOYSA-N 0.000 description 1
- LEKDKCNKJWATJG-UHFFFAOYSA-N 1,3-bis[[5-(4-chlorophenyl)-2-oxopiperidin-1-yl]methyl]thiourea Chemical compound C1=CC(Cl)=CC=C1C1CN(CNC(=S)NCN2C(CCC(C2)C=2C=CC(Cl)=CC=2)=O)C(=O)CC1 LEKDKCNKJWATJG-UHFFFAOYSA-N 0.000 description 1
- WGTTWTKOIIZJFX-UHFFFAOYSA-N 1,3-bis[[5-(4-chlorophenyl)-2-oxopiperidin-1-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1C1CN(CNC(=O)NCN2C(CCC(C2)C=2C=CC(Cl)=CC=2)=O)C(=O)CC1 WGTTWTKOIIZJFX-UHFFFAOYSA-N 0.000 description 1
- RBKSMIFUYASCHJ-UHFFFAOYSA-N 1-(1-aminobutan-2-yl)pyrrolidin-2-one Chemical compound CCC(CN)N1CCCC1=O RBKSMIFUYASCHJ-UHFFFAOYSA-N 0.000 description 1
- CKMHSQLCQDLXPD-UHFFFAOYSA-N 1-(1-aminoethyl)pyrrolidin-2-one Chemical compound CC(N)N1CCCC1=O CKMHSQLCQDLXPD-UHFFFAOYSA-N 0.000 description 1
- WIPVFDPATAQHCV-UHFFFAOYSA-N 1-(1-aminopropan-2-yl)pyrrolidin-2-one Chemical compound NCC(C)N1CCCC1=O WIPVFDPATAQHCV-UHFFFAOYSA-N 0.000 description 1
- QVEGALUUEJJLEE-UHFFFAOYSA-N 1-(1-aminopropyl)pyrrolidin-2-one Chemical compound CCC(N)N1CCCC1=O QVEGALUUEJJLEE-UHFFFAOYSA-N 0.000 description 1
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- PNPOQLOYUIXLCD-UHFFFAOYSA-N 1-(aminomethyl)-3-butylpyrrolidin-2-one Chemical compound CCCCC1CCN(CN)C1=O PNPOQLOYUIXLCD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/02—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D227/00—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00
- C07D227/02—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D227/06—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D227/08—Oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5494/77A GB1582351A (en) | 1977-02-10 | 1977-02-10 | Disubstituted ureas and thioureas |
| GB549477 | 1977-02-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI780384A7 FI780384A7 (fi) | 1978-08-11 |
| FI66601B FI66601B (fi) | 1984-07-31 |
| FI66601C true FI66601C (fi) | 1984-11-12 |
Family
ID=9797264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI780384A FI66601C (fi) | 1977-02-10 | 1978-02-07 | Foerfarande foer framstaellning av terapeutiskt aktiva 1,3-disubstituerade urinaemnen eller 2-tiourinaemnen |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US4216221A (en, 2012) |
| JP (1) | JPS53101366A (en, 2012) |
| AT (1) | AT359080B (en, 2012) |
| AU (1) | AU516765B2 (en, 2012) |
| BE (1) | BE863792A (en, 2012) |
| BG (2) | BG29646A2 (en, 2012) |
| CA (1) | CA1078858A (en, 2012) |
| CH (1) | CH632999A5 (en, 2012) |
| CS (1) | CS207603B2 (en, 2012) |
| DD (1) | DD134097A5 (en, 2012) |
| DE (1) | DE2805769A1 (en, 2012) |
| DK (1) | DK57778A (en, 2012) |
| ES (1) | ES466815A1 (en, 2012) |
| FI (1) | FI66601C (en, 2012) |
| FR (1) | FR2380262A1 (en, 2012) |
| GB (1) | GB1582351A (en, 2012) |
| GR (1) | GR66187B (en, 2012) |
| HU (1) | HU176033B (en, 2012) |
| IL (1) | IL54011A (en, 2012) |
| IN (1) | IN148262B (en, 2012) |
| IT (1) | IT1102355B (en, 2012) |
| LU (1) | LU79047A1 (en, 2012) |
| NL (1) | NL7801572A (en, 2012) |
| NO (1) | NO780431L (en, 2012) |
| NZ (1) | NZ186425A (en, 2012) |
| OA (1) | OA05883A (en, 2012) |
| PH (1) | PH14362A (en, 2012) |
| PL (2) | PL112570B1 (en, 2012) |
| PT (1) | PT67637B (en, 2012) |
| SE (1) | SE426593B (en, 2012) |
| SU (2) | SU936810A3 (en, 2012) |
| YU (1) | YU29778A (en, 2012) |
| ZA (1) | ZA78793B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792604A (en) * | 1987-03-20 | 1988-12-20 | Gaf Corporation | Manufacture of haloalkyl lactams |
| US5334720A (en) * | 1991-03-07 | 1994-08-02 | Fisons Corporation | Diphenyl-1-(aminoalkyl)-2-piperidinone and -2-pyrrolidinone derivatives having anticonvulsant properties |
| DE4127404A1 (de) * | 1991-08-19 | 1993-02-25 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE19519498A1 (de) * | 1995-05-27 | 1996-05-09 | Hermann Trey | Integriertes Diebstahl- und Transportsicherungssystem mit Alarmeinrichtung für mobile Gegenstände oder mobile Behältnisse |
| JP2007513105A (ja) * | 2003-12-02 | 2007-05-24 | ユ セ ベ ソシエテ アノニム | イミダゾール誘導体、その製法及び使用 |
| FR2937973B1 (fr) * | 2008-11-04 | 2010-11-05 | Galderma Res & Dev | Modulateurs des recepteurs de la melanocortine, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique |
| WO2015103756A1 (en) * | 2014-01-09 | 2015-07-16 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2850529A (en) * | 1955-03-28 | 1958-09-02 | Pfizer & Co C | Bis quaternary ammonia alkyl ureas |
| GB1039113A (en) * | 1964-08-06 | 1966-08-17 | Ucb Sa | New n-substituted lactams |
| GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
-
1977
- 1977-02-10 GB GB5494/77A patent/GB1582351A/en not_active Expired
-
1978
- 1978-02-07 FI FI780384A patent/FI66601C/fi not_active IP Right Cessation
- 1978-02-07 SE SE7801403A patent/SE426593B/sv unknown
- 1978-02-08 DK DK57778A patent/DK57778A/da not_active Application Discontinuation
- 1978-02-08 NO NO780431A patent/NO780431L/no unknown
- 1978-02-09 CH CH144378A patent/CH632999A5/fr not_active IP Right Cessation
- 1978-02-09 PL PL1978213691A patent/PL112570B1/pl unknown
- 1978-02-09 AT AT92578A patent/AT359080B/de not_active IP Right Cessation
- 1978-02-09 AU AU33155/78A patent/AU516765B2/en not_active Expired
- 1978-02-09 IL IL54011A patent/IL54011A/xx unknown
- 1978-02-09 CA CA296,746A patent/CA1078858A/en not_active Expired
- 1978-02-09 GR GR55398A patent/GR66187B/el unknown
- 1978-02-09 OA OA56404A patent/OA05883A/xx unknown
- 1978-02-09 ES ES466815A patent/ES466815A1/es not_active Expired
- 1978-02-09 NZ NZ186425A patent/NZ186425A/xx unknown
- 1978-02-09 PL PL20453278A patent/PL204532A1/xx unknown
- 1978-02-09 PH PH20766A patent/PH14362A/en unknown
- 1978-02-09 DD DD78203636A patent/DD134097A5/xx unknown
- 1978-02-09 JP JP1402478A patent/JPS53101366A/ja active Granted
- 1978-02-09 BG BG040068A patent/BG29646A2/xx unknown
- 1978-02-09 PT PT67637A patent/PT67637B/pt unknown
- 1978-02-09 ZA ZA00780793A patent/ZA78793B/xx unknown
- 1978-02-09 US US05/876,922 patent/US4216221A/en not_active Expired - Lifetime
- 1978-02-09 IN IN107/DEL/78A patent/IN148262B/en unknown
- 1978-02-09 BE BE1008706A patent/BE863792A/xx not_active IP Right Cessation
- 1978-02-09 YU YU00297/78A patent/YU29778A/xx unknown
- 1978-02-09 BG BG038632A patent/BG29571A3/xx unknown
- 1978-02-10 HU HU78UE88A patent/HU176033B/hu unknown
- 1978-02-10 CS CS78888A patent/CS207603B2/cs unknown
- 1978-02-10 SU SU782578051A patent/SU936810A3/ru active
- 1978-02-10 NL NL7801572A patent/NL7801572A/xx not_active Application Discontinuation
- 1978-02-10 LU LU79047A patent/LU79047A1/xx unknown
- 1978-02-10 FR FR7804062A patent/FR2380262A1/fr active Granted
- 1978-02-10 IT IT48004/78A patent/IT1102355B/it active
- 1978-02-10 DE DE19782805769 patent/DE2805769A1/de active Granted
- 1978-07-17 SU SU782637643A patent/SU1097622A1/ru active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: UCB S.A. |