NO780431L - Fremgangsmaate ved fremstilling av 1,3-disubstituerte ureaer og 2-thioureaer - Google Patents
Fremgangsmaate ved fremstilling av 1,3-disubstituerte ureaer og 2-thioureaerInfo
- Publication number
- NO780431L NO780431L NO780431A NO780431A NO780431L NO 780431 L NO780431 L NO 780431L NO 780431 A NO780431 A NO 780431A NO 780431 A NO780431 A NO 780431A NO 780431 L NO780431 L NO 780431L
- Authority
- NO
- Norway
- Prior art keywords
- urea
- oxo
- formula
- methyl
- bis
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 150000003672 ureas Chemical class 0.000 title claims abstract description 7
- 230000008569 process Effects 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 94
- -1 alkyl radical Chemical class 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- 150000003951 lactams Chemical class 0.000 claims description 18
- 239000004202 carbamide Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052717 sulfur Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 150000005840 aryl radicals Chemical class 0.000 claims description 6
- WMKONRFEZGAHTE-UHFFFAOYSA-N imuracetam Chemical group C1CCC(=O)N1CNC(=O)NCN1CCCC1=O WMKONRFEZGAHTE-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- IBVZQJPVEOFKHO-UHFFFAOYSA-N 1,3-bis[(3-butyl-2-oxopyrrolidin-1-yl)methyl]thiourea Chemical group O=C1C(CCCC)CCN1CNC(=S)NCN1C(=O)C(CCCC)CC1 IBVZQJPVEOFKHO-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- SWRKIJMEQDJRSP-UHFFFAOYSA-N 1,3-bis[(2-methyl-5-oxopyrrolidin-1-yl)methyl]urea Chemical group CC1CCC(=O)N1CNC(=O)NCN1C(=O)CCC1C SWRKIJMEQDJRSP-UHFFFAOYSA-N 0.000 claims description 2
- OUHLLHUYCDWKKI-UHFFFAOYSA-N 1,3-bis[1-(2-oxopyrrolidin-1-yl)ethyl]urea Chemical group C1CCC(=O)N1C(C)NC(=O)NC(C)N1CCCC1=O OUHLLHUYCDWKKI-UHFFFAOYSA-N 0.000 claims description 2
- LPHJXXWMYVCPLR-UHFFFAOYSA-N 1,3-bis[2-(2-oxopyrrolidin-1-yl)butyl]urea Chemical group C1CCC(=O)N1C(CC)CNC(=O)NCC(CC)N1CCCC1=O LPHJXXWMYVCPLR-UHFFFAOYSA-N 0.000 claims description 2
- WIQYMFJZMVQEQA-UHFFFAOYSA-N 1,3-bis[2-(2-oxopyrrolidin-1-yl)ethyl]urea Chemical group C1CCC(=O)N1CCNC(=O)NCCN1CCCC1=O WIQYMFJZMVQEQA-UHFFFAOYSA-N 0.000 claims description 2
- QHTRKNSEUBMHBM-UHFFFAOYSA-N 1,3-bis[[4-(4-chlorophenyl)-3-methyl-2-oxopyrrolidin-1-yl]methyl]urea Chemical group 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 claims description 2
- 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
- 238000006114 decarboxylation reaction Methods 0.000 claims description 2
- 239000003937 drug carrier Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- XUVZJGZIDMBJTP-UHFFFAOYSA-N 1-[(2-oxoazepan-1-yl)methyl]-3-[(2-oxopyrrolidin-1-yl)methyl]thiourea Chemical group O=C1CCCN1CNC(=S)NCN1C(=O)CCCCC1 XUVZJGZIDMBJTP-UHFFFAOYSA-N 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 241000786363 Rhampholeon spectrum Species 0.000 description 56
- 229910052757 nitrogen Inorganic materials 0.000 description 56
- 239000000243 solution Substances 0.000 description 40
- 238000004458 analytical method Methods 0.000 description 30
- 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- WQKVZVGKZZWLPJ-UHFFFAOYSA-N 1-(aminomethyl)pyrrolidin-2-one Chemical compound NCN1CCCC1=O WQKVZVGKZZWLPJ-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 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
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000012360 testing method Methods 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
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 206010021143 Hypoxia Diseases 0.000 description 5
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 5
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 229960004526 piracetam Drugs 0.000 description 5
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- GXFZCDMWGMFGFL-KKXMJGKMSA-N (+)-Tubocurarine chloride hydrochloride Chemical compound [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 4
- 241001111317 Chondrodendron tomentosum Species 0.000 description 4
- 239000008709 Curare Substances 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003826 tablet Substances 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
- 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
- 206010001488 Aggression Diseases 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 230000016571 aggressive behavior Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000001146 hypoxic effect Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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
- 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 2
- HJORCZCMNWLHMB-UHFFFAOYSA-N 1-(3-aminopropyl)pyrrolidin-2-one Chemical compound NCCCN1CCCC1=O HJORCZCMNWLHMB-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
- UHNAFVMMAIULEC-UHFFFAOYSA-N 1-[(2-oxoazonan-1-yl)methyl]-3-[(2-oxopyrrolidin-1-yl)methyl]urea Chemical compound C1CCCCCCC(=O)N1CNC(=O)NCN1CCCC1=O UHNAFVMMAIULEC-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
- LLKFNPUXQZHIAE-UHFFFAOYSA-N 5-(3-aminopropyl)-8-bromo-3-methyl-2h-pyrazolo[4,3-c]quinolin-4-one Chemical compound O=C1N(CCCN)C2=CC=C(Br)C=C2C2=C1C(C)=NN2 LLKFNPUXQZHIAE-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 241000699670 Mus sp. Species 0.000 description 2
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- 241000906446 Theraps Species 0.000 description 2
- 206010048010 Withdrawal syndrome Diseases 0.000 description 2
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- 230000010354 integration Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 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
- 125000004433 nitrogen atom Chemical group N* 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
- 239000000829 suppository Substances 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 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
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- 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
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- 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
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- 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
- HHEKNWQXFVOUNJ-UHFFFAOYSA-N 1-(2-aminoethyl)pyrrolidin-2-one Chemical compound NCCN1CCCC1=O HHEKNWQXFVOUNJ-UHFFFAOYSA-N 0.000 description 1
- PNPOQLOYUIXLCD-UHFFFAOYSA-N 1-(aminomethyl)-3-butylpyrrolidin-2-one Chemical compound CCCCC1CCN(CN)C1=O PNPOQLOYUIXLCD-UHFFFAOYSA-N 0.000 description 1
- OYAMUKQONGKODH-UHFFFAOYSA-N 1-(aminomethyl)-3-ethyl-3-phenylpyrrolidin-2-one Chemical compound C=1C=CC=CC=1C1(CC)CCN(CN)C1=O OYAMUKQONGKODH-UHFFFAOYSA-N 0.000 description 1
- XOGGVHDBWSYQPN-UHFFFAOYSA-N 1-(aminomethyl)-4,5-dimethylpyrrolidin-2-one Chemical compound CC1CC(=O)N(CN)C1C XOGGVHDBWSYQPN-UHFFFAOYSA-N 0.000 description 1
- VCSDIODMQUQBSB-UHFFFAOYSA-N 1-(aminomethyl)-4-(4-chlorophenyl)-3-methylpyrrolidin-2-one Chemical compound C1N(CN)C(=O)C(C)C1C1=CC=C(Cl)C=C1 VCSDIODMQUQBSB-UHFFFAOYSA-N 0.000 description 1
- BLNLQBBJVODTES-UHFFFAOYSA-N 1-(aminomethyl)-4-phenylpyrrolidin-2-one Chemical compound C1C(=O)N(CN)CC1C1=CC=CC=C1 BLNLQBBJVODTES-UHFFFAOYSA-N 0.000 description 1
- PYVUFSKJSKQCCU-UHFFFAOYSA-N 1-(aminomethyl)-5-methylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1CN PYVUFSKJSKQCCU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MBZUCKXSDGDNPR-UHFFFAOYSA-N 1-(aminomethyl)azepan-2-one Chemical compound NCN1CCCCCC1=O MBZUCKXSDGDNPR-UHFFFAOYSA-N 0.000 description 1
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- YPWDQXFNLNQVQB-UHFFFAOYSA-N 1-(chloromethyl)-4-phenylpyrrolidin-2-one Chemical compound C1C(=O)N(CCl)CC1C1=CC=CC=C1 YPWDQXFNLNQVQB-UHFFFAOYSA-N 0.000 description 1
- AYEOFPZPAQRMNT-UHFFFAOYSA-N 1-(chloromethyl)azepan-2-one Chemical compound ClCN1CCCCCC1=O AYEOFPZPAQRMNT-UHFFFAOYSA-N 0.000 description 1
- MYEOEVZPIFPPJZ-UHFFFAOYSA-N 1-(chloromethyl)azocan-2-one Chemical compound ClCN1CCCCCCC1=O MYEOEVZPIFPPJZ-UHFFFAOYSA-N 0.000 description 1
- KPYLMLKHOIKFNY-UHFFFAOYSA-N 1-(chloromethyl)azonan-2-one Chemical compound ClCN1CCCCCCCC1=O KPYLMLKHOIKFNY-UHFFFAOYSA-N 0.000 description 1
- KEBMRNXDMRFGNV-UHFFFAOYSA-N 1-(chloromethyl)pyrrolidin-2-one Chemical compound ClCN1CCCC1=O KEBMRNXDMRFGNV-UHFFFAOYSA-N 0.000 description 1
- HNHCCFKOLTWZIF-UHFFFAOYSA-N 1-(hydroxymethyl)-3,5-dimethylpyrrolidin-2-one Chemical compound CC1CC(C)C(=O)N1CO HNHCCFKOLTWZIF-UHFFFAOYSA-N 0.000 description 1
- JTRYDZATHWXZAA-UHFFFAOYSA-N 1-(hydroxymethyl)-4,5-dimethylpyrrolidin-2-one Chemical compound CC1CC(=O)N(CO)C1C JTRYDZATHWXZAA-UHFFFAOYSA-N 0.000 description 1
- GQQDOHYQZSIZJS-UHFFFAOYSA-N 1-(hydroxymethyl)-4-phenylpyrrolidin-2-one Chemical compound C1C(=O)N(CO)CC1C1=CC=CC=C1 GQQDOHYQZSIZJS-UHFFFAOYSA-N 0.000 description 1
- WKHLELQVUJDECS-UHFFFAOYSA-N 1-(hydroxymethyl)-5-methylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1CO WKHLELQVUJDECS-UHFFFAOYSA-N 0.000 description 1
- QBUDWHWPQWURCC-UHFFFAOYSA-N 1-(hydroxymethyl)azepan-2-one Chemical compound OCN1CCCCCC1=O QBUDWHWPQWURCC-UHFFFAOYSA-N 0.000 description 1
- GKRNNIBVCLXJFQ-UHFFFAOYSA-N 1-(hydroxymethyl)azocan-2-one Chemical compound OCN1CCCCCCC1=O GKRNNIBVCLXJFQ-UHFFFAOYSA-N 0.000 description 1
- ULMSMOFNQANNEH-UHFFFAOYSA-N 1-(isocyanatomethyl)pyrrolidin-2-one Chemical compound O=C=NCN1CCCC1=O ULMSMOFNQANNEH-UHFFFAOYSA-N 0.000 description 1
- JCZOPUAOTJUSOZ-UHFFFAOYSA-N 1-[(2-oxoazepan-1-yl)methyl]-3-[(2-oxopyrrolidin-1-yl)methyl]urea Chemical compound C1CCCCC(=O)N1CNC(=O)NCN1CCCC1=O JCZOPUAOTJUSOZ-UHFFFAOYSA-N 0.000 description 1
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- UBRKGRIYZLVBHC-UHFFFAOYSA-N 2-(2-oxo-5-phenylpyrrolidin-1-yl)acetamide Chemical compound C1CC(=O)N(CC(=O)N)C1C1=CC=CC=C1 UBRKGRIYZLVBHC-UHFFFAOYSA-N 0.000 description 1
- MXTNWENLEHXXBZ-UHFFFAOYSA-N 2-(chloromethyl)-3-methyl-2-azaspiro[4.5]decan-1-one Chemical compound O=C1N(CCl)C(C)CC11CCCCC1 MXTNWENLEHXXBZ-UHFFFAOYSA-N 0.000 description 1
- HTOUNUIOVXQHCF-UHFFFAOYSA-N 2-(hydroxymethyl)-3-methyl-2-azaspiro[4.5]decan-1-one Chemical compound O=C1N(CO)C(C)CC11CCCCC1 HTOUNUIOVXQHCF-UHFFFAOYSA-N 0.000 description 1
- JJXUKXQTFKDOSH-UHFFFAOYSA-N 3,5,5-trimethylpyrrolidin-2-one Chemical compound CC1CC(C)(C)NC1=O JJXUKXQTFKDOSH-UHFFFAOYSA-N 0.000 description 1
- HYUUHOWKQHHTDK-UHFFFAOYSA-N 3-butyl-1-(chloromethyl)pyrrolidin-2-one Chemical compound CCCCC1CCN(CCl)C1=O HYUUHOWKQHHTDK-UHFFFAOYSA-N 0.000 description 1
- DIPDJKGIUKCYAB-UHFFFAOYSA-N 3-butyl-1-(hydroxymethyl)pyrrolidin-2-one Chemical compound CCCCC1CCN(CO)C1=O DIPDJKGIUKCYAB-UHFFFAOYSA-N 0.000 description 1
- SBVIIPZWOHKZKO-UHFFFAOYSA-N 3-ethyl-1-(hydroxymethyl)-3-phenylpyrrolidin-2-one Chemical compound C=1C=CC=CC=1C1(CC)CCN(CO)C1=O SBVIIPZWOHKZKO-UHFFFAOYSA-N 0.000 description 1
- ONTKBOZAIAIFDI-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-(hydroxymethyl)-3-methylpyrrolidin-2-one Chemical compound C1N(CO)C(=O)C(C)C1C1=CC=C(Cl)C=C1 ONTKBOZAIAIFDI-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 206010034962 Photopsia Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
- 206010038678 Respiratory depression Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
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- 239000003054 catalyst Substances 0.000 description 1
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- WLDBKDYSWDAYMZ-UHFFFAOYSA-N decan-1-one Chemical compound CCCCCCCCC[C]=O WLDBKDYSWDAYMZ-UHFFFAOYSA-N 0.000 description 1
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- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 239000000839 emulsion Substances 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
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- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000036649 mental concentration Effects 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229950009119 oxydipentonium chloride Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000065 phosphene Inorganic materials 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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Classifications
-
- 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
Landscapes
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5494/77A GB1582351A (en) | 1977-02-10 | 1977-02-10 | Disubstituted ureas and thioureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO780431L true NO780431L (no) | 1978-08-11 |
Family
ID=9797264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO780431A NO780431L (no) | 1977-02-10 | 1978-02-08 | Fremgangsmaate ved fremstilling av 1,3-disubstituerte ureaer og 2-thioureaer |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US4216221A (el) |
| JP (1) | JPS53101366A (el) |
| AT (1) | AT359080B (el) |
| AU (1) | AU516765B2 (el) |
| BE (1) | BE863792A (el) |
| BG (2) | BG29646A2 (el) |
| CA (1) | CA1078858A (el) |
| CH (1) | CH632999A5 (el) |
| CS (1) | CS207603B2 (el) |
| DD (1) | DD134097A5 (el) |
| DE (1) | DE2805769A1 (el) |
| DK (1) | DK57778A (el) |
| ES (1) | ES466815A1 (el) |
| FI (1) | FI66601C (el) |
| FR (1) | FR2380262A1 (el) |
| GB (1) | GB1582351A (el) |
| GR (1) | GR66187B (el) |
| HU (1) | HU176033B (el) |
| IL (1) | IL54011A (el) |
| IN (1) | IN148262B (el) |
| IT (1) | IT1102355B (el) |
| LU (1) | LU79047A1 (el) |
| NL (1) | NL7801572A (el) |
| NO (1) | NO780431L (el) |
| NZ (1) | NZ186425A (el) |
| OA (1) | OA05883A (el) |
| PH (1) | PH14362A (el) |
| PL (2) | PL112570B1 (el) |
| PT (1) | PT67637B (el) |
| SE (1) | SE426593B (el) |
| SU (2) | SU936810A3 (el) |
| YU (1) | YU29778A (el) |
| ZA (1) | ZA78793B (el) |
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 |
| BRPI0417157A (pt) * | 2003-12-02 | 2007-03-06 | Ucb Sa | composto, composição farmacêutica, e, uso de um composto ou de uma composição farmacêutica |
| 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 DD DD78203636A patent/DD134097A5/xx unknown
- 1978-02-09 OA OA56404A patent/OA05883A/xx unknown
- 1978-02-09 AT AT92578A patent/AT359080B/de not_active IP Right Cessation
- 1978-02-09 ES ES466815A patent/ES466815A1/es not_active Expired
- 1978-02-09 YU YU00297/78A patent/YU29778A/xx unknown
- 1978-02-09 IN IN107/DEL/78A patent/IN148262B/en unknown
- 1978-02-09 PH PH20766A patent/PH14362A/en unknown
- 1978-02-09 CA CA296,746A patent/CA1078858A/en not_active Expired
- 1978-02-09 US US05/876,922 patent/US4216221A/en not_active Expired - Lifetime
- 1978-02-09 BE BE1008706A patent/BE863792A/xx not_active IP Right Cessation
- 1978-02-09 JP JP1402478A patent/JPS53101366A/ja active Granted
- 1978-02-09 IL IL54011A patent/IL54011A/xx unknown
- 1978-02-09 GR GR55398A patent/GR66187B/el unknown
- 1978-02-09 PT PT67637A patent/PT67637B/pt unknown
- 1978-02-09 CH CH144378A patent/CH632999A5/fr not_active IP Right Cessation
- 1978-02-09 BG BG040068A patent/BG29646A2/xx unknown
- 1978-02-09 PL PL1978213691A patent/PL112570B1/pl unknown
- 1978-02-09 NZ NZ186425A patent/NZ186425A/xx unknown
- 1978-02-09 ZA ZA00780793A patent/ZA78793B/xx unknown
- 1978-02-09 BG BG038632A patent/BG29571A3/xx not_active Expired
- 1978-02-09 PL PL20453278A patent/PL204532A1/xx unknown
- 1978-02-09 AU AU33155/78A patent/AU516765B2/en not_active Expired
- 1978-02-10 IT IT48004/78A patent/IT1102355B/it active
- 1978-02-10 HU HU78UE88A patent/HU176033B/hu unknown
- 1978-02-10 SU SU782578051A patent/SU936810A3/ru active
- 1978-02-10 LU LU79047A patent/LU79047A1/xx unknown
- 1978-02-10 DE DE19782805769 patent/DE2805769A1/de active Granted
- 1978-02-10 NL NL7801572A patent/NL7801572A/xx not_active Application Discontinuation
- 1978-02-10 FR FR7804062A patent/FR2380262A1/fr active Granted
- 1978-02-10 CS CS78888A patent/CS207603B2/cs unknown
- 1978-07-17 SU SU782637643A patent/SU1097622A1/ru active
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