SE426593B - Sett att framstella 1,3-disubstituerade karbamider och 2-tiokarbamider - Google Patents

Sett att framstella 1,3-disubstituerade karbamider och 2-tiokarbamider

Info

Publication number: SE426593B
Authority: SE; Sweden
Prior art keywords: yield; formula; theory; mol; compound
Prior art date: 1977-02-10

Application number

SE7801403A

Other languages

English (en)

Swedish (sv)

Other versions

SE7801403L (sv

Inventor

Lannoy J De

Original Assignee

Ucb Sa

Priority date (The priority date 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 date listed.)

1977-02-10

Filing date

1978-02-07

Publication date

1983-01-31

1978-02-07 Application filed by Ucb Sa filed Critical Ucb Sa

1978-08-11 Publication of SE7801403L publication Critical patent/SE7801403L/xx

1978-11-29 Priority to GB7846487A priority Critical patent/GB2021729B/en

1983-01-31 Publication of SE426593B publication Critical patent/SE426593B/sv

Links

238000000034 method Methods 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 27
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 24
-1 1,3-disubstituted urea Chemical class 0.000 claims description 22
239000004202 carbamide Substances 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 16
150000003951 lactams Chemical class 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 11
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
125000004103 aminoalkyl group Chemical group 0.000 claims description 9
230000008569 process Effects 0.000 claims description 9
235000013877 carbamide Nutrition 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
125000002883 imidazolyl group Chemical group 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
239000012948 isocyanate Substances 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
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 108
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
238000002329 infrared spectrum Methods 0.000 description 40
239000000243 solution Substances 0.000 description 40
238000004458 analytical method Methods 0.000 description 30
229910052757 nitrogen Inorganic materials 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
230000000694 effects Effects 0.000 description 17
239000000203 mixture Substances 0.000 description 17
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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 14
241001465754 Metazoa Species 0.000 description 13
GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
229960004526 piracetam Drugs 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
238000001228 spectrum Methods 0.000 description 11
WQKVZVGKZZWLPJ-UHFFFAOYSA-N 1-(aminomethyl)pyrrolidin-2-one Chemical compound NCN1CCCC1=O WQKVZVGKZZWLPJ-UHFFFAOYSA-N 0.000 description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
241000700159 Rattus Species 0.000 description 9
241000786363 Rhampholeon spectrum 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
239000000460 chlorine Substances 0.000 description 8
239000000047 product Substances 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
239000000126 substance Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 6
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
206010021143 Hypoxia Diseases 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
230000009467 reduction 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
231100000419 toxicity Toxicity 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
RHVFEIMRWWISEG-UHFFFAOYSA-N CN(C(N)=O)N(CCC1)C1=O Chemical compound CN(C(N)=O)N(CCC1)C1=O RHVFEIMRWWISEG-UHFFFAOYSA-N 0.000 description 3
230000016571 aggressive behavior Effects 0.000 description 3
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
238000005915 ammonolysis reaction Methods 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 3
230000001146 hypoxic effect Effects 0.000 description 3
238000007912 intraperitoneal administration Methods 0.000 description 3
238000002955 isolation Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 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
239000002904 solvent Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 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
WIPVFDPATAQHCV-UHFFFAOYSA-N 1-(1-aminopropan-2-yl)pyrrolidin-2-one Chemical compound NCC(C)N1CCCC1=O WIPVFDPATAQHCV-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
HJORCZCMNWLHMB-UHFFFAOYSA-N 1-(3-aminopropyl)pyrrolidin-2-one Chemical compound NCCCN1CCCC1=O HJORCZCMNWLHMB-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
MBZUCKXSDGDNPR-UHFFFAOYSA-N 1-(aminomethyl)azepan-2-one Chemical compound NCN1CCCCCC1=O MBZUCKXSDGDNPR-UHFFFAOYSA-N 0.000 description 2
MYEOEVZPIFPPJZ-UHFFFAOYSA-N 1-(chloromethyl)azocan-2-one Chemical compound ClCN1CCCCCCC1=O MYEOEVZPIFPPJZ-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
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
238000006105 Hofmann reaction Methods 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
229920002472 Starch Polymers 0.000 description 2
241000906446 Theraps Species 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
235000019359 magnesium stearate Nutrition 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
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
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
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 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
CKMHSQLCQDLXPD-UHFFFAOYSA-N 1-(1-aminoethyl)pyrrolidin-2-one Chemical compound CC(N)N1CCCC1=O CKMHSQLCQDLXPD-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
RVKQEMDYWNDSQP-UHFFFAOYSA-N 1-(aminomethyl)-3,5,5-trimethylpyrrolidin-2-one Chemical compound CC1CC(C)(C)N(CN)C1=O RVKQEMDYWNDSQP-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
BHDQHRSBICVIIZ-UHFFFAOYSA-N 1-(aminomethyl)azocan-2-one Chemical compound NCN1CCCCCCC1=O BHDQHRSBICVIIZ-UHFFFAOYSA-N 0.000 description 1
RGIWZVANCCCZMJ-UHFFFAOYSA-N 1-(aminomethyl)piperidin-2-one Chemical compound NCN1CCCCC1=O RGIWZVANCCCZMJ-UHFFFAOYSA-N 0.000 description 1
BGLCJWJBRNPSLR-UHFFFAOYSA-N 1-(chloromethyl)-3,5,5-trimethylpyrrolidin-2-one Chemical compound CC1CC(C)(C)N(CCl)C1=O BGLCJWJBRNPSLR-UHFFFAOYSA-N 0.000 description 1
RPIAMTGITMPGDG-UHFFFAOYSA-N 1-(chloromethyl)-3,5-dimethylpyrrolidin-2-one Chemical compound CC1CC(C)C(=O)N1CCl RPIAMTGITMPGDG-UHFFFAOYSA-N 0.000 description 1
AQJGBGLHQOZYKK-UHFFFAOYSA-N 1-(chloromethyl)-3-ethyl-3-phenylpyrrolidin-2-one Chemical compound C=1C=CC=CC=1C1(CC)CCN(CCl)C1=O AQJGBGLHQOZYKK-UHFFFAOYSA-N 0.000 description 1
GRWCFGMNXJIIBZ-UHFFFAOYSA-N 1-(chloromethyl)-4,5-dimethylpyrrolidin-2-one Chemical compound CC1CC(=O)N(CCl)C1C GRWCFGMNXJIIBZ-UHFFFAOYSA-N 0.000 description 1
IMHBCYBTYBRXER-UHFFFAOYSA-N 1-(chloromethyl)-4-(4-chlorophenyl)-3-methylpyrrolidin-2-one Chemical compound C1N(CCl)C(=O)C(C)C1C1=CC=C(Cl)C=C1 IMHBCYBTYBRXER-UHFFFAOYSA-N 0.000 description 1
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
WTVZEZRCEVJIDN-UHFFFAOYSA-N 1-(chloromethyl)-5-(4-chlorophenyl)piperidin-2-one Chemical compound C1CC(=O)N(CCl)CC1C1=CC=C(Cl)C=C1 WTVZEZRCEVJIDN-UHFFFAOYSA-N 0.000 description 1
YXSPRXDRLVSOEZ-UHFFFAOYSA-N 1-(chloromethyl)-5-methylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1CCl YXSPRXDRLVSOEZ-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
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
CDYZMHBHPMPGKU-UHFFFAOYSA-N 1-(hydroxymethyl)-3,5,5-trimethylpyrrolidin-2-one Chemical compound CC1CC(C)(C)N(CO)C1=O CDYZMHBHPMPGKU-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
FGMPJBUNFYKHFV-UHFFFAOYSA-N 1-[(1-aminocyclohexa-2,4-dien-1-yl)methyl]pyrrolidin-2-one Chemical compound NC1(CN2C(CCC2)=O)CC=CC=C1 FGMPJBUNFYKHFV-UHFFFAOYSA-N 0.000 description 1
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 1
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
FDFMICBCWSSWJO-UHFFFAOYSA-N 2-(2-oxopyrrolidin-1-yl)acetyl chloride Chemical compound ClC(=O)CN1CCCC1=O FDFMICBCWSSWJO-UHFFFAOYSA-N 0.000 description 1
NBXODYKSBBYGBJ-UHFFFAOYSA-N 2-(2-oxopyrrolidin-1-yl)propanenitrile Chemical compound N#CC(C)N1CCCC1=O NBXODYKSBBYGBJ-UHFFFAOYSA-N 0.000 description 1
XEQLLPRJTLYVKP-UHFFFAOYSA-N 2-(aminomethyl)-3-methyl-2-azaspiro[4.5]decan-1-one Chemical compound O=C1N(CN)C(C)CC11CCCCC1 XEQLLPRJTLYVKP-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
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
VWWSUIJLKDAFFW-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-(hydroxymethyl)piperidin-2-one Chemical compound C1CC(=O)N(CO)CC1C1=CC=C(Cl)C=C1 VWWSUIJLKDAFFW-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
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
208000021479 Cardiovascular injury Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
206010010071 Coma Diseases 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
206010020591 Hypercapnia Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
241000699666 Mus <mouse, genus> Species 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
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
229930006000 Sucrose Natural products 0.000 description 1
244000269722 Thea sinensis Species 0.000 description 1
208000001435 Thromboembolism Diseases 0.000 description 1
206010048010 Withdrawal syndrome Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002744 anti-aggregatory effect Effects 0.000 description 1
229940127218 antiplatelet drug Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001540 azides Chemical class 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
150000001728 carbonyl compounds Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
210000001638 cerebellum Anatomy 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940126208 compound 22 Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000000911 decarboxylating effect Effects 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
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
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000008570 general process Effects 0.000 description 1
239000003292 glue Substances 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
230000003301 hydrolyzing effect Effects 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
208000014674 injury Diseases 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
238000004519 manufacturing process Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 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
239000011707 mineral Substances 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 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
239000000106 platelet aggregation inhibitor Substances 0.000 description 1
229920000642 polymer Polymers 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
230000008092 positive effect Effects 0.000 description 1
230000001144 postural effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000003825 pressing Methods 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
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000011514 reflex Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
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 1
230000003966 vascular damage Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

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)

SE7801403A 1977-02-10 1978-02-07 Sett att framstella 1,3-disubstituerade karbamider och 2-tiokarbamider SE426593B (sv)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
GB7846487A GB2021729B (en)	1978-02-07	1978-11-29	Lifting chains

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 (2)

Publication Number	Publication Date
SE7801403L SE7801403L (sv)	1978-08-11
SE426593B true SE426593B (sv)	1983-01-31

Family

ID=9797264

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7801403A SE426593B (sv)	1977-02-10	1978-02-07	Sett att framstella 1,3-disubstituerade karbamider och 2-tiokarbamider

Country Status (33)

Country	Link
US (1)	US4216221A (sr)
JP (1)	JPS53101366A (sr)
AT (1)	AT359080B (sr)
AU (1)	AU516765B2 (sr)
BE (1)	BE863792A (sr)
BG (2)	BG29571A3 (sr)
CA (1)	CA1078858A (sr)
CH (1)	CH632999A5 (sr)
CS (1)	CS207603B2 (sr)
DD (1)	DD134097A5 (sr)
DE (1)	DE2805769A1 (sr)
DK (1)	DK57778A (sr)
ES (1)	ES466815A1 (sr)
FI (1)	FI66601C (sr)
FR (1)	FR2380262A1 (sr)
GB (1)	GB1582351A (sr)
GR (1)	GR66187B (sr)
HU (1)	HU176033B (sr)
IL (1)	IL54011A (sr)
IN (1)	IN148262B (sr)
IT (1)	IT1102355B (sr)
LU (1)	LU79047A1 (sr)
NL (1)	NL7801572A (sr)
NO (1)	NO780431L (sr)
NZ (1)	NZ186425A (sr)
OA (1)	OA05883A (sr)
PH (1)	PH14362A (sr)
PL (2)	PL204532A1 (sr)
PT (1)	PT67637B (sr)
SE (1)	SE426593B (sr)
SU (2)	SU936810A3 (sr)
YU (1)	YU29778A (sr)
ZA (1)	ZA78793B (sr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
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
WO2005054188A1 (en) *	2003-12-02	2005-06-16	Ucb, S.A.	Imidazole derivatives, processes for preparing them and their uses
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)

* Cited by examiner, † Cited by third party
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 NO NO780431A patent/NO780431L/no unknown
- 1978-02-08 DK DK57778A patent/DK57778A/da not_active Application Discontinuation
- 1978-02-09 PL PL20453278A patent/PL204532A1/xx unknown
- 1978-02-09 BG BG038632A patent/BG29571A3/xx unknown
- 1978-02-09 IN IN107/DEL/78A patent/IN148262B/en unknown
- 1978-02-09 ES ES466815A patent/ES466815A1/es not_active Expired
- 1978-02-09 OA OA56404A patent/OA05883A/xx unknown
- 1978-02-09 NZ NZ186425A patent/NZ186425A/xx unknown
- 1978-02-09 US US05/876,922 patent/US4216221A/en not_active Expired - Lifetime
- 1978-02-09 ZA ZA00780793A patent/ZA78793B/xx unknown
- 1978-02-09 PL PL1978213691A patent/PL112570B1/pl unknown
- 1978-02-09 CH CH144378A patent/CH632999A5/fr not_active IP Right Cessation
- 1978-02-09 BE BE1008706A patent/BE863792A/xx not_active IP Right Cessation
- 1978-02-09 AT AT92578A patent/AT359080B/de not_active IP Right Cessation
- 1978-02-09 IL IL54011A patent/IL54011A/xx unknown
- 1978-02-09 CA CA296,746A patent/CA1078858A/en not_active Expired
- 1978-02-09 BG BG040068A patent/BG29646A2/xx unknown
- 1978-02-09 YU YU00297/78A patent/YU29778A/xx unknown
- 1978-02-09 PH PH20766A patent/PH14362A/en unknown
- 1978-02-09 PT PT67637A patent/PT67637B/pt unknown
- 1978-02-09 JP JP1402478A patent/JPS53101366A/ja active Granted
- 1978-02-09 DD DD78203636A patent/DD134097A5/xx unknown
- 1978-02-09 GR GR55398A patent/GR66187B/el unknown
- 1978-02-09 AU AU33155/78A patent/AU516765B2/en not_active Expired
- 1978-02-10 HU HU78UE88A patent/HU176033B/hu unknown
- 1978-02-10 FR FR7804062A patent/FR2380262A1/fr active Granted
- 1978-02-10 LU LU79047A patent/LU79047A1/xx unknown
- 1978-02-10 NL NL7801572A patent/NL7801572A/xx not_active Application Discontinuation
- 1978-02-10 SU SU782578051A patent/SU936810A3/ru active
- 1978-02-10 IT IT48004/78A patent/IT1102355B/it active
- 1978-02-10 CS CS78888A patent/CS207603B2/cs unknown
- 1978-02-10 DE DE19782805769 patent/DE2805769A1/de active Granted
- 1978-07-17 SU SU782637643A patent/SU1097622A1/ru active

Also Published As

Publication number	Publication date
DE2805769C2 (sr)	1989-10-26
ZA78793B (en)	1979-01-31
PT67637B (pt)	1979-09-20
FI780384A7 (fi)	1978-08-11
JPH0140027B2 (sr)	1989-08-24
FR2380262B1 (sr)	1982-04-23
JPS53101366A (en)	1978-09-04
LU79047A1 (fr)	1978-09-28
FI66601C (fi)	1984-11-12
AU3315578A (en)	1979-08-16
AT359080B (de)	1980-10-27
AU516765B2 (en)	1981-06-18
IN148262B (sr)	1980-12-27
IL54011A0 (en)	1978-04-30
DD134097A5 (de)	1979-02-07
FR2380262A1 (fr)	1978-09-08
DE2805769A1 (de)	1978-08-17
GR66187B (sr)	1981-01-21
CH632999A5 (fr)	1982-11-15
US4216221A (en)	1980-08-05
YU29778A (en)	1983-01-21
IT1102355B (it)	1985-10-07
OA05883A (fr)	1981-05-31
NO780431L (no)	1978-08-11
SU1097622A1 (ru)	1984-06-15
PH14362A (en)	1981-06-03
PT67637A (pt)	1978-03-01
GB1582351A (en)	1981-01-07
CS207603B2 (en)	1981-08-31
SE7801403L (sv)	1978-08-11
NZ186425A (en)	1980-04-28
IT7848004A0 (it)	1978-02-10
HU176033B (en)	1980-11-28
IL54011A (en)	1981-05-20
CA1078858A (en)	1980-06-03
PL204532A1 (pl)	1978-12-04
DK57778A (da)	1978-08-11
BG29571A3 (en)	1980-12-12
ES466815A1 (es)	1978-10-01
ATA92578A (de)	1980-03-15
NL7801572A (nl)	1978-08-14
FI66601B (fi)	1984-07-31
SU936810A3 (ru)	1982-06-15
BG29646A2 (bg)	1981-01-15
BE863792A (fr)	1978-08-09
PL112570B1 (en)	1980-10-31

Publication	Publication Date	Title
US3978045A (en)	1976-08-31	N2 -dansyl-L-arginine derivatives, and the pharmaceutically acceptable acid addition salts thereof
Coyne et al.	1968	Anticonvulsant semicarbazides
US5258397A (en)	1993-11-02	3-Isoxazoyl derivatives endowed with anticonvulsant activity, procedure for their preparation and their pharmaceutical compositions
JPH0226629B2 (sr)	1990-06-12
US3769274A (en)	1973-10-30	Aminophenyl-cycloamidines
US4216221A (en)	1980-08-05	1,3-Disubstituted (2-thio)ureas
CA1340904C (en)	2000-02-22	Amino acid derivative anticonvulsant
EP0475214B1 (en)	1995-06-07	Caffeic acid derivatives and pharmaceutical compositions containing the same
US4189495A (en)	1980-02-19	2-Methoxy-benzamide derivatives
EP0384843B1 (fr)	1994-08-31	Dérivés de la 1-arylsulfonyl 2-pipéridinone, leur procédé et les intermédiaires de préparation, leur application comme médicaments et les compositions les renfermant
SU1222191A3 (ru)	1986-03-30	Способ получени соединений гуанидина или их фармакологически совместимых солей
US4158060A (en)	1979-06-12	2-Methoxy-benzamide derivatives
US4142051A (en)	1979-02-27	Arylaminoimidazoline derivatives
US4083979A (en)	1978-04-11	Thiazolidine derivatives and their use as salidiuretics
US4252811A (en)	1981-02-24	Hexahydro-trans-pyridoindole neuroleptic agents
US3637746A (en)	1972-01-25	Process for preparing n-aryl-alpha-oxocyclopolymethylene amines an related compounds
US3865823A (en)	1975-02-11	(2-Nitro-1-imidazolyl)-carbamates
US3574194A (en)	1971-04-06	1-alpha-ethyl - alpha - methyl-succinimido) -4-sulphonamidobenzene and related compounds
US3708473A (en)	1973-01-02	3,3-dichloro-2-oxopolymethylenimines
US3576819A (en)	1971-04-27	Esters of alpha-(1-substituted-3-pyrrolidinyl)-alpha-phenyl acetic acid
FI61698C (fi)	1982-09-10	Foerfarande foer framstaellning av nya saosom hjaertmediciner anvaendbara piperazinderivat samt deras salter
US3299089A (en)	1967-01-17	Derivatives of 5-methyloxazoline and 5-chloromethyloxazoline
US4352807A (en)	1982-10-05	Hexahydro-trans-pyridoindole neuroleptic agents
FI56831C (fi)	1980-04-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara pyrrolidyliden- piperidyliden- och hexahydroazepinyliden-urinaemnen
US3868384A (en)	1975-02-25	Perfluoroalkyl derivatives