CH667648A5 - N-nikotinoylaminosaeuren. - Google Patents

N-nikotinoylaminosaeuren. Download PDF

Info

Publication number: CH667648A5
Authority: CH; Switzerland
Prior art keywords: compound; dose; control; effect; reflex
Prior art date: 1986-07-16

Application number

CH2923/86A

Other languages

German (de)

English (en)

Inventor

Leonid Dmitrievich Smirnov

Tatyana Alexandrovna Voronina

Larisa Grigorievna Stolyarova

Taisia Leonovna Garibova

Ramiz Atallaevich Akhundov

Elena Alexandrovna Kuznetsova

Kirill Mikhailovich Djumaev

Artur Viktorovich Valdman

Georgy Mikhailovich Rudenko

Original Assignee

Ni Institutfarmakologii Akadem

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.)

1986-07-16

Filing date

1986-07-22

Publication date

1988-10-31

1986-07-22 Application filed by Ni Institutfarmakologii Akadem filed Critical Ni Institutfarmakologii Akadem

1988-10-31 Publication of CH667648A5 publication Critical patent/CH667648A5/de

Links

150000001875 compounds Chemical class 0.000 description 108
230000011514 reflex Effects 0.000 description 48
241001465754 Metazoa Species 0.000 description 43
GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical group NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 42
230000000694 effects Effects 0.000 description 42
208000000044 Amnesia Diseases 0.000 description 36
208000031091 Amnestic disease Diseases 0.000 description 36
230000006986 amnesia Effects 0.000 description 36
239000000126 substance Substances 0.000 description 34
241000699670 Mus sp. Species 0.000 description 33
238000012360 testing method Methods 0.000 description 30
239000000243 solution Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
206010021143 Hypoxia Diseases 0.000 description 27
230000007954 hypoxia Effects 0.000 description 25
238000002360 preparation method Methods 0.000 description 24
230000001960 triggered effect Effects 0.000 description 20
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 18
229960004986 pyritinol Drugs 0.000 description 18
230000001777 nootropic effect Effects 0.000 description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
230000003496 anti-amnesic effect Effects 0.000 description 16
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
241000700159 Rattus Species 0.000 description 14
238000002474 experimental method Methods 0.000 description 14
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
230000015654 memory Effects 0.000 description 10
239000002253 acid Substances 0.000 description 9
238000000034 method Methods 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
-1 N-nicotinoylamino acids Chemical class 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
230000000803 paradoxical effect Effects 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
206010010904 Convulsion Diseases 0.000 description 6
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
206010020591 Hypercapnia Diseases 0.000 description 6
241000699666 Mus <mouse, genus> Species 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 6
230000001143 conditioned effect Effects 0.000 description 6
210000003608 fece Anatomy 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
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 6
229960005152 pentetrazol Drugs 0.000 description 6
235000010288 sodium nitrite Nutrition 0.000 description 6
WHUUTDBJXJRKMK-VKHMYHEASA-N L-Glutamic acid Natural products OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 5
206010044565 Tremor Diseases 0.000 description 5
229940125904 compound 1 Drugs 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
238000007912 intraperitoneal administration Methods 0.000 description 5
239000002664 nootropic agent Substances 0.000 description 5
230000035939 shock Effects 0.000 description 5
235000011121 sodium hydroxide Nutrition 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
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 4
238000013459 approach Methods 0.000 description 4
230000006399 behavior Effects 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
210000004556 brain Anatomy 0.000 description 4
230000035622 drinking Effects 0.000 description 4
238000001362 electron spin resonance spectrum Methods 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
229960002989 glutamic acid Drugs 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
230000002035 prolonged effect Effects 0.000 description 4
230000004083 survival effect Effects 0.000 description 4
238000002211 ultraviolet spectrum Methods 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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
208000007101 Muscle Cramp Diseases 0.000 description 3
LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
230000001154 acute effect Effects 0.000 description 3
HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 3
150000001540 azides Chemical class 0.000 description 3
230000008033 biological extinction Effects 0.000 description 3
230000036461 convulsion Effects 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
WHUUTDBJXJRKMK-UHFFFAOYSA-N glutamic acid Chemical class OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
238000011835 investigation Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
230000000978 myorelaxation Effects 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
ATTDCVLRGFEHEO-UHFFFAOYSA-N 5-Hydroxynicotinic acid Chemical compound OC(=O)C1=CN=CC(O)=C1 ATTDCVLRGFEHEO-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
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
208000026139 Memory disease Diseases 0.000 description 2
230000009471 action Effects 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
230000001773 anti-convulsant effect Effects 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000008859 change Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
PCPIANOJERKFJI-UHFFFAOYSA-N ethyl 5-bromopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(Br)=C1 PCPIANOJERKFJI-UHFFFAOYSA-N 0.000 description 2
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
230000008569 process Effects 0.000 description 2
238000011160 research Methods 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 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
SLNRADBTOAQAHM-UHFFFAOYSA-N 4-[(5-hydroxypyridine-3-carbonyl)amino]butanoic acid Chemical compound OC(=O)CCCNC(=O)C1=CN=CC(O)=C1 SLNRADBTOAQAHM-UHFFFAOYSA-N 0.000 description 1
VFEKMAOUJHONFD-UHFFFAOYSA-N 5-[[[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methyldisulfanyl]methyl]-4-(hydroxymethyl)-2-methylpyridin-3-ol;hydrate;dihydrochloride Chemical compound O.Cl.Cl.OCC1=C(O)C(C)=NC=C1CSSCC1=CN=C(C)C(O)=C1CO VFEKMAOUJHONFD-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
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 1
OLOBXYMJLZJQQF-UHFFFAOYSA-N 5-hydroxypyridine-3-carbohydrazide Chemical compound NNC(=O)C1=CN=CC(O)=C1 OLOBXYMJLZJQQF-UHFFFAOYSA-N 0.000 description 1
229940000681 5-hydroxytryptophan Drugs 0.000 description 1
206010020651 Hyperkinesia Diseases 0.000 description 1
208000000269 Hyperkinesis Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
XZTYGFHCIAKPGJ-UHFFFAOYSA-N Meclofenoxate Chemical compound CN(C)CCOC(=O)COC1=CC=C(Cl)C=C1 XZTYGFHCIAKPGJ-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
208000030886 Traumatic Brain injury Diseases 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000002539 anti-aggressive effect Effects 0.000 description 1
230000002082 anti-convulsion Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000036770 blood supply Effects 0.000 description 1
230000003788 cerebral perfusion Effects 0.000 description 1
210000004720 cerebrum Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000009194 climbing Effects 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
230000002920 convulsive effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
230000007123 defense Effects 0.000 description 1
230000006735 deficit Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
235000019441 ethanol Nutrition 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
230000005284 excitation Effects 0.000 description 1
244000144993 groups of animals Species 0.000 description 1
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
230000006993 memory improvement Effects 0.000 description 1
230000036997 mental performance Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
230000008450 motivation Effects 0.000 description 1
231100000957 no side effect Toxicity 0.000 description 1
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 1
239000003960 organic solvent Substances 0.000 description 1
LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
229960004526 piracetam Drugs 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
239000000047 product Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
206010040560 shock Diseases 0.000 description 1
230000006403 short-term memory Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000009423 ventilation 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)

CH2923/86A 1986-07-16 1986-07-22 N-nikotinoylaminosaeuren. CH667648A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE8603135A SE455093B (sv)	1986-07-16	1986-07-16	N-nikotinoylaminosyror

Publications (1)

Publication Number	Publication Date
CH667648A5 true CH667648A5 (de)	1988-10-31

Family

ID=20365125

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH2923/86A CH667648A5 (de)	1986-07-16	1986-07-22	N-nikotinoylaminosaeuren.

Country Status (5)

Country	Link
JP (1)	JPS6344565A (fr)
BE (1)	BE905154A (fr)
CH (1)	CH667648A5 (fr)
FR (1)	FR2602232B1 (fr)
SE (1)	SE455093B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
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 (fr) *	1997-10-09	2003-05-14	Ono Pharmaceutical Co	Derives d'acide aminobutanoique
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
SE455093B (sv)	1988-06-20
SE8603135L (sv)	1988-01-17

Legal Events

Date	Code	Title	Description
1994-03-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2460891C2 (de)	1982-09-23	1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DE3587122T2 (de)	1993-07-15	Pharmakologisch aktive derivate von tryptophan und diese enthaltende pharmazeutische zusammensetzungen.
DE60131032T2 (de)	2008-08-14	Verwendung von antikonvulsiven Aminosäure zur Behandlung von Migräne
DE2332878C2 (de)	1983-07-28	Salze von Cephalosporinen mit Arginin und Lysin, ihre Herstellung und injizierbare pharmazeutische Zubereitungen
DE69430695T2 (de)	2002-09-12	Verfahren zur verbesserung der wahrnehmung mit partiellen agonisten des glycin/nmda-rezeptorkomplexes
DE3522506C2 (fr)	1988-03-10
DE2236987A1 (de)	1973-03-01	Pyrazolo eckige klammer auf 1,5a eckige klammer zu -pyrimidine und verfahren zu ihrer herstellung
DE1645971A1 (de)	1970-07-16	Verfahren zur Herstellung von therapeutisch wertvollen (Indazol-3-yl)-oxyalkansaeuren
DE3872127T2 (de)	1992-12-03	4-aminopyridin-derivate und ihre saueradditionssalze.
CH670952A5 (fr)	1989-07-31
DE69122812T2 (de)	1997-03-20	Glutathionderivat
DE69808475T2 (de)	2003-01-30	Aminosäurederivate zur behandlung von schlaganfall
DE2112349A1 (de)	1971-10-14	Di- und tri-substituierte Imidazole
CH630378A5 (de)	1982-06-15	Verfahren zur herstellung neuer kondensierter pyrimidin-derivate.
DE69011013T2 (de)	1994-12-22	1-(Pyridinylamino)-2-pyrrolidinone, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel.
DE69104996T2 (de)	1995-04-20	Amidoderivate von glutamin-, asparagin- und 2-aminoadipinsäuren mit antigastrin-wirkung.
CH667648A5 (de)	1988-10-31	N-nikotinoylaminosaeuren.
DE10048715A1 (de)	2004-05-19	Verwendung von Aminosäure zur Behandlung von Schmerz
DE2801478C2 (fr)	1991-01-31
DE2322561A1 (de)	1973-11-15	Trisubstituierte imidazole
DE2328896A1 (de)	1973-12-20	Quaternaere phenylcycloalkylammoniumverbindungen und daraus hergestellte arzneipraeparate
DE69004267T2 (de)	1994-02-24	Glycyl-p-amino-pyridin zur behandlung von seniler demenz.
DE60117770T2 (de)	2006-12-14	Cholinderivate zur behandlung der alzheimerkrankheit
DE4101324A1 (de)	1992-07-23	Isoxazol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3231571C2 (fr)	1988-11-10