SE455093B - N-nikotinoylaminosyror - Google Patents
N-nikotinoylaminosyrorInfo
- Publication number
- SE455093B SE455093B SE8603135A SE8603135A SE455093B SE 455093 B SE455093 B SE 455093B SE 8603135 A SE8603135 A SE 8603135A SE 8603135 A SE8603135 A SE 8603135A SE 455093 B SE455093 B SE 455093B
- Authority
- SE
- Sweden
- Prior art keywords
- compound
- effect
- dose
- animals
- reflex
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 11
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 11
- -1 N-nicotinoylamino acids Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 description 131
- 241001465754 Metazoa Species 0.000 description 62
- 230000000694 effects Effects 0.000 description 56
- 230000011514 reflex Effects 0.000 description 51
- 241000699670 Mus sp. Species 0.000 description 36
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical group NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 36
- 238000002474 experimental method Methods 0.000 description 33
- 238000012360 testing method Methods 0.000 description 31
- 208000000044 Amnesia Diseases 0.000 description 30
- 208000031091 Amnestic disease Diseases 0.000 description 30
- 206010021143 Hypoxia Diseases 0.000 description 30
- 230000006986 amnesia Effects 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- 239000000126 substance Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 230000007954 hypoxia Effects 0.000 description 26
- 230000001143 conditioned effect Effects 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
- 241000700159 Rattus Species 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 230000000141 anti-hypoxic effect Effects 0.000 description 15
- 230000003496 anti-amnesic effect Effects 0.000 description 13
- 239000002475 cognitive enhancer Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- SIXLXDIJGIWWFU-UHFFFAOYSA-N pyritinol Chemical compound OCC1=C(O)C(C)=NC=C1CSSCC1=CN=C(C)C(O)=C1CO SIXLXDIJGIWWFU-UHFFFAOYSA-N 0.000 description 12
- 229960004986 pyritinol Drugs 0.000 description 12
- 230000015654 memory Effects 0.000 description 11
- 206010020591 Hypercapnia Diseases 0.000 description 10
- 206010010904 Convulsion Diseases 0.000 description 9
- 230000037396 body weight Effects 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000001777 nootropic effect Effects 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 235000010288 sodium nitrite Nutrition 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- XZTYGFHCIAKPGJ-UHFFFAOYSA-N Meclofenoxate Chemical compound CN(C)CCOC(=O)COC1=CC=C(Cl)C=C1 XZTYGFHCIAKPGJ-UHFFFAOYSA-N 0.000 description 7
- HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 7
- 230000000803 paradoxical effect Effects 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- MYYMQXJRABNCIG-UHFFFAOYSA-N 5-hydroxypyridine-3-carbonyl azide Chemical compound OC1=CN=CC(C(=O)N=[N+]=[N-])=C1 MYYMQXJRABNCIG-UHFFFAOYSA-N 0.000 description 6
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 6
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 6
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 150000001540 azides Chemical class 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 6
- 229960002646 scopolamine Drugs 0.000 description 6
- 238000007920 subcutaneous administration Methods 0.000 description 6
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 5
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 5
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 230000034994 death Effects 0.000 description 5
- 231100000517 death Toxicity 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 230000002262 irrigation Effects 0.000 description 5
- 238000003973 irrigation Methods 0.000 description 5
- 230000001670 myorelaxant effect Effects 0.000 description 5
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 5
- 230000035939 shock Effects 0.000 description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
- IYGYMKDQCDOMRE-QRWMCTBCSA-N Bicculine Chemical compound O([C@H]1C2C3=CC=4OCOC=4C=C3CCN2C)C(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-QRWMCTBCSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
- 230000003187 abdominal effect Effects 0.000 description 4
- 229940124277 aminobutyric acid Drugs 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
- 230000006399 behavior Effects 0.000 description 4
- AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 4
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 4
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 230000003109 amnesic effect Effects 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229960002989 glutamic acid Drugs 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 238000003780 insertion Methods 0.000 description 3
- 230000037431 insertion Effects 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XFZGYOJFPGPYCS-QMMMGPOBSA-N nooglutyl Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)C1=CN=CC(O)=C1 XFZGYOJFPGPYCS-QMMMGPOBSA-N 0.000 description 3
- 239000002664 nootropic agent Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000010254 subcutaneous injection Methods 0.000 description 3
- 239000007929 subcutaneous injection Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- FIVHOHCAXWQPGC-UHFFFAOYSA-N 2-[2-(4-chlorophenoxy)acetyl]oxyethyl-dimethylazanium;chloride Chemical compound Cl.CN(C)CCOC(=O)COC1=CC=C(Cl)C=C1 FIVHOHCAXWQPGC-UHFFFAOYSA-N 0.000 description 2
- VERXTAUONOFMLH-UHFFFAOYSA-N 5-bromopyridine-3-carbohydrazide Chemical compound NNC(=O)C1=CN=CC(Br)=C1 VERXTAUONOFMLH-UHFFFAOYSA-N 0.000 description 2
- LBVLLEAKKBHEDJ-UHFFFAOYSA-N 5-bromopyridine-3-carbonyl azide Chemical compound BrC1=CN=CC(C(=O)N=[N+]=[N-])=C1 LBVLLEAKKBHEDJ-UHFFFAOYSA-N 0.000 description 2
- OLOBXYMJLZJQQF-UHFFFAOYSA-N 5-hydroxypyridine-3-carbohydrazide Chemical compound NNC(=O)C1=CN=CC(O)=C1 OLOBXYMJLZJQQF-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010044565 Tremor Diseases 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000002539 anti-aggressive effect Effects 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 230000009194 climbing Effects 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 230000035622 drinking Effects 0.000 description 2
- 230000001146 hypoxic effect Effects 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 239000003158 myorelaxant agent Substances 0.000 description 2
- 229960005152 pentetrazol Drugs 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001256 tonic effect Effects 0.000 description 2
- XFZGYOJFPGPYCS-UHFFFAOYSA-N 2-[(5-hydroxypyridine-3-carbonyl)amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NC(=O)C1=CN=CC(O)=C1 XFZGYOJFPGPYCS-UHFFFAOYSA-N 0.000 description 1
- QEZOCPJRXMUIQS-UHFFFAOYSA-N 2-oxo-1h-pyridine-3-carbohydrazide Chemical class NNC(=O)C1=CC=CN=C1O QEZOCPJRXMUIQS-UHFFFAOYSA-N 0.000 description 1
- FQIUCPGDKPXSLL-UHFFFAOYSA-N 5-bromopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(Br)=C1 FQIUCPGDKPXSLL-UHFFFAOYSA-N 0.000 description 1
- 241000002039 Amesia Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 208000027534 Emotional disease Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101000933374 Gallus gallus Brain-specific homeobox/POU domain protein 3 Proteins 0.000 description 1
- 241000196171 Hydrodictyon reticulatum Species 0.000 description 1
- 206010020651 Hyperkinesia Diseases 0.000 description 1
- 208000000269 Hyperkinesis Diseases 0.000 description 1
- 241000756171 Hypoxis Species 0.000 description 1
- 241001579016 Nanoa Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 102100026459 POU domain, class 3, transcription factor 2 Human genes 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000007172 age related pathology Effects 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 230000001353 anxiety effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- LFDNUOROKFFJLE-UHFFFAOYSA-N ethyl 5-hydroxypyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(O)=C1 LFDNUOROKFFJLE-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 230000005021 gait Effects 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N glutamic acid Chemical class OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000001259 mesencephalon Anatomy 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 238000000554 physical therapy Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- NIFIFKQPDTWWGU-UHFFFAOYSA-N pyrite Chemical compound [Fe+2].[S-][S-] NIFIFKQPDTWWGU-UHFFFAOYSA-N 0.000 description 1
- 229910052683 pyrite Inorganic materials 0.000 description 1
- 239000011028 pyrite Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 210000004189 reticular formation Anatomy 0.000 description 1
- 230000006403 short-term memory Effects 0.000 description 1
- 230000004620 sleep latency Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 108010072897 transcription factor Brn-2 Proteins 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8603135A SE455093B (sv) | 1986-07-16 | 1986-07-16 | N-nikotinoylaminosyror |
| CH2923/86A CH667648A5 (de) | 1986-07-16 | 1986-07-22 | N-nikotinoylaminosaeuren. |
| BE0/216961A BE905154A (fr) | 1986-07-16 | 1986-07-23 | Acides n-nicotinoylamines. |
| FR8611224A FR2602232B1 (fr) | 1986-07-16 | 1986-08-01 | Acides n-nicotinoylamines |
| JP61186714A JPS6344565A (ja) | 1986-07-16 | 1986-08-08 | Ｎ−ニコチノイルアミノ酸 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8603135A SE455093B (sv) | 1986-07-16 | 1986-07-16 | N-nikotinoylaminosyror |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8603135D0 SE8603135D0 (sv) | 1986-07-16 |
| SE8603135L SE8603135L (sv) | 1988-01-17 |
| SE455093B true SE455093B (sv) | 1988-06-20 |
Family
ID=20365125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8603135A SE455093B (sv) | 1986-07-16 | 1986-07-16 | N-nikotinoylaminosyror |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS6344565A (de) |
| BE (1) | BE905154A (de) |
| CH (1) | CH667648A5 (de) |
| FR (1) | FR2602232B1 (de) |
| SE (1) | SE455093B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06113106A (ja) * | 1992-09-25 | 1994-04-22 | Ricoh Co Ltd | デ−タ読出処理装置 |
| EP1024134A4 (de) * | 1997-10-09 | 2003-05-14 | Ono Pharmaceutical Co | Derivate der aminobutansäure |
| JP6479522B2 (ja) | 2015-03-23 | 2019-03-06 | 本田技研工業株式会社 | ケーブル連結機構 |
| RU2612253C1 (ru) * | 2016-03-23 | 2017-03-03 | Общество с ограниченной ответственностью "ТАВИТА" | Способ получения N-(5-гидроксиникотиноил)-L-глутаминовой кислоты |
-
1986
- 1986-07-16 SE SE8603135A patent/SE455093B/sv not_active IP Right Cessation
- 1986-07-22 CH CH2923/86A patent/CH667648A5/de not_active IP Right Cessation
- 1986-07-23 BE BE0/216961A patent/BE905154A/fr not_active IP Right Cessation
- 1986-08-01 FR FR8611224A patent/FR2602232B1/fr not_active Expired
- 1986-08-08 JP JP61186714A patent/JPS6344565A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE905154A (fr) | 1987-01-23 |
| SE8603135D0 (sv) | 1986-07-16 |
| JPS6344565A (ja) | 1988-02-25 |
| FR2602232A1 (fr) | 1988-02-05 |
| FR2602232B1 (fr) | 1988-11-10 |
| SE8603135L (sv) | 1988-01-17 |
| CH667648A5 (de) | 1988-10-31 |
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