NO772893L - Dihydro-okso-nikotinsyrer og fremgangsmaate til deres fremstilling - Google Patents

Dihydro-okso-nikotinsyrer og fremgangsmaate til deres fremstilling

Info

Publication number: NO772893L
Authority: NO; Norway
Prior art keywords: dihydro; oxo; formula; residue; nicotinic acid
Prior art date: 1976-08-20

Application number

NO772893A

Other languages

English (en)

Norwegian (no)

Inventor

Rudi Weyer

Volker Hitzel

Ernold Granzer

Original Assignee

Hoechst Ag

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.)

1976-08-20

Filing date

1977-08-19

Publication date

1978-02-21

1977-08-19 Application filed by Hoechst Ag filed Critical Hoechst Ag

1978-02-21 Publication of NO772893L publication Critical patent/NO772893L/no

Links

238000000034 method Methods 0.000 title claims description 21
239000002253 acid Substances 0.000 title claims description 9
150000007513 acids Chemical class 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title description 10
-1 alkylcycloalkenyl Chemical group 0.000 claims description 44
150000001875 compounds Chemical class 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
150000002148 esters Chemical class 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
150000002690 malonic acid derivatives Chemical class 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
YSLIPUSJNFIFAB-UHFFFAOYSA-N 2-oxopyridine-1-carboxylic acid Chemical compound OC(=O)N1C=CC=CC1=O YSLIPUSJNFIFAB-UHFFFAOYSA-N 0.000 claims description 3
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 3
QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 2
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 2
238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
208000030159 metabolic disease Diseases 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 121
238000002844 melting Methods 0.000 description 61
230000008018 melting Effects 0.000 description 61
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 8
239000000155 melt Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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239000008280 blood Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
LDRFFJDBXVSKKM-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-2-oxopyridine-3-carboxylic acid Chemical compound O=C1C(C(=O)O)=CC=CN1CC1=CC=C(Cl)C=C1 LDRFFJDBXVSKKM-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000007127 saponification reaction Methods 0.000 description 4
MTENBFXQUYLERK-UHFFFAOYSA-N 1-butyl-2-oxopyridine-3-carboxylic acid Chemical compound CCCCN1C=CC=C(C(O)=O)C1=O MTENBFXQUYLERK-UHFFFAOYSA-N 0.000 description 3
PSUJOJWQYDDNCE-UHFFFAOYSA-N 1-butyl-6-methyl-2-oxopyridine-3-carboxylic acid Chemical compound CCCCN1C(C)=CC=C(C(O)=O)C1=O PSUJOJWQYDDNCE-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
UEYQJQVBUVAELZ-UHFFFAOYSA-N 2-Hydroxynicotinic acid Chemical compound OC(=O)C1=CC=CN=C1O UEYQJQVBUVAELZ-UHFFFAOYSA-N 0.000 description 2
KHIJAVHPLSAGLB-UHFFFAOYSA-N 2-oxo-1-(1-phenylethyl)pyridine-3-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C(=O)N1C(C)C1=CC=CC=C1 KHIJAVHPLSAGLB-UHFFFAOYSA-N 0.000 description 2
RHXKQTZFJULYNZ-UHFFFAOYSA-N 4,6-dimethyl-1-[(4-methylphenyl)methyl]-2-oxopyridine-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1CN1C(=O)C(C(O)=O)=C(C)C=C1C RHXKQTZFJULYNZ-UHFFFAOYSA-N 0.000 description 2
XNDIRYNTVJADKX-UHFFFAOYSA-N 4,6-dimethyl-2-oxo-1-(2-phenylethyl)pyridine-3-carboxylic acid Chemical compound O=C1C(C(O)=O)=C(C)C=C(C)N1CCC1=CC=CC=C1 XNDIRYNTVJADKX-UHFFFAOYSA-N 0.000 description 2
XRIHTJYXIHOBDQ-UHFFFAOYSA-N 6-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C(=O)N1 XRIHTJYXIHOBDQ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000203 mixture Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000001226 reprecipitation Methods 0.000 description 2
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NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
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DYTSLVNBEBOIGG-UHFFFAOYSA-N 1-(2-methoxyethyl)-2-oxopyridine-3-carboxylic acid Chemical compound COCCN1C=CC=C(C(O)=O)C1=O DYTSLVNBEBOIGG-UHFFFAOYSA-N 0.000 description 1
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AGFKLIIEOYDROP-UHFFFAOYSA-N 1-[(4-methylphenyl)methyl]-2-oxopyridine-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1CN1C(=O)C(C(O)=O)=CC=C1 AGFKLIIEOYDROP-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
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RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
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229960002896 clonidine Drugs 0.000 description 1
239000003218 coronary vasodilator agent Substances 0.000 description 1
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical class NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229960004815 meprobamate Drugs 0.000 description 1
LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 1
UKKHUKFEKBKULS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-cyanoacetamide Chemical compound ClC1=CC=C(CNC(=O)CC#N)C=C1 UKKHUKFEKBKULS-UHFFFAOYSA-N 0.000 description 1
MGZNARROBKPUST-UHFFFAOYSA-N n-butyl-2-cyanoacetamide Chemical compound CCCCNC(=O)CC#N MGZNARROBKPUST-UHFFFAOYSA-N 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
229960001989 prenylamine Drugs 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229930003231 vitamin Natural products 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
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- 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
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO772893A 1976-08-20 1977-08-19 Dihydro-okso-nikotinsyrer og fremgangsmaate til deres fremstilling NO772893L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19762637477 DE2637477A1 (de)	1976-08-20	1976-08-20	Dihydro-oxo-nicotinsaeuren und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
NO772893L true NO772893L (no)	1978-02-21

Family

ID=5985902

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO772893A NO772893L (no)	1976-08-20	1977-08-19	Dihydro-okso-nikotinsyrer og fremgangsmaate til deres fremstilling

Country Status (11)

Country	Link
JP (1)	JPS5325578A (da)
BE (1)	BE857994A (da)
DE (1)	DE2637477A1 (da)
DK (1)	DK370277A (da)
FI (1)	FI772453A7 (da)
FR (1)	FR2362127A1 (da)
NL (1)	NL7708982A (da)
NO (1)	NO772893L (da)
PT (1)	PT66934B (da)
SE (1)	SE7709333L (da)
ZA (1)	ZA775045B (da)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4220648A (en) *	1979-01-22	1980-09-02	The Upjohn Company	Antidiabetic 1,2-dihydro-2-oxo-6-neopentyl-nicotinic acids
US4288440A (en)	1980-08-29	1981-09-08	The Upjohn Company	Pyridinones
US4645766A (en) *	1981-10-19	1987-02-24	The Upjohn Company	1,2-dihydro-2-oxo-3-hydroxymethyl pyridines, compositions and use
JPS59194824A (ja) *	1983-04-19	1984-11-05	Ube Ind Ltd	樹脂成形機
AU3564889A (en) *	1988-06-03	1990-01-05	Upjohn Company, The	Cyclic lactams for cholesterol and atherosclerosis control
AU6979091A (en) *	1989-12-22	1991-07-24	Upjohn Company, The	Pyridinones useful as antiatherosclerotic agents
AU8495091A (en) *	1990-08-21	1992-03-17	Upjohn Company, The	Bisphosphonic acid derivatives as anti-arthritic agents
CZ403592A3 (en) *	1992-02-20	1993-12-15	Hoechst Ag	Arylcarbonylaminoalkyldihydrooxopyridines, process of their preparation and their use
DE4309552A1 (de) *	1993-03-24	1994-09-29	Bayer Ag	Substituierte Stickstoff-Heterocyclen
US5814645A (en) *	1993-03-24	1998-09-29	Bayer Aktiengesellschaft	Arylor hetaryl substituted nitrogen heterocycles and their use as pesticides
US7998986B2 (en)	2001-12-21	2011-08-16	Exelixis Patent Company Llc	Modulators of LXR
US7482366B2 (en)	2001-12-21	2009-01-27	X-Ceptor Therapeutics, Inc.	Modulators of LXR

1976
- 1976-08-20 DE DE19762637477 patent/DE2637477A1/de active Pending
1977
- 1977-08-15 NL NL7708982A patent/NL7708982A/xx not_active Application Discontinuation
- 1977-08-17 FI FI772453A patent/FI772453A7/fi not_active Application Discontinuation
- 1977-08-18 PT PT66934A patent/PT66934B/pt unknown
- 1977-08-18 SE SE7709333A patent/SE7709333L/xx unknown
- 1977-08-19 NO NO772893A patent/NO772893L/no unknown
- 1977-08-19 DK DK370277A patent/DK370277A/da unknown
- 1977-08-19 FR FR7725394A patent/FR2362127A1/fr not_active Withdrawn
- 1977-08-19 ZA ZA00775045A patent/ZA775045B/xx unknown
- 1977-08-20 JP JP9911677A patent/JPS5325578A/ja active Pending
- 1977-08-22 BE BE180336A patent/BE857994A/xx unknown

Also Published As

Publication number	Publication date
JPS5325578A (en)	1978-03-09
FI772453A7 (fi)	1978-02-21
PT66934B (de)	1979-04-13
PT66934A (de)	1977-09-01
FR2362127A1 (fr)	1978-03-17
SE7709333L (sv)	1978-02-21
ZA775045B (en)	1978-07-26
NL7708982A (nl)	1978-02-22
DE2637477A1 (de)	1978-02-23
DK370277A (da)	1978-02-21
BE857994A (fr)	1978-02-22

Publication	Publication Date	Title
TWI779022B (zh)	2022-10-01	Ask1抑制劑化合物及其用途
US5118686A (en)	1992-06-02	Phenylpyrimidones
US5155110A (en)	1992-10-13	Fenamic acid hydroxamate derivatives having cyclooxygenase and 5-lipoxygenase inhibition
RU2088582C1 (ru)	1997-08-27	Производные арил-(или гетероарил)- пиперазинилалкилазолов, способ их получения и фармацевтическая композиция на их основе
BG61367B2 (bg)	1997-06-30	Циклоалкилтриазоли
JPS59501409A (ja)	1984-08-09	ピリドン化合物
JP3526305B2 (ja)	2004-05-10	イミダゾ（１，２−ａ）ピリジンのアルコキシアルカリカルバメート
JPS6136282A (ja)	1986-02-20	窒素を含む複素環式化合物からなる医薬品とその製造方法
NO780558L (no)	1978-08-21	Benzoesyre og dens derivater samt fremgangsmaate til deres fremstilling
US10717727B2 (en)	2020-07-21	Pyridinium compounds
JPH05140108A (ja)	1993-06-08	ピリジニルピペラジン誘導体
JPS5980657A (ja)	1984-05-10	３−フエノキシ−１−アゼチジンカルボキサミド、その製造方法及びそれからなる鎮痙剤
DE2637477A1 (de)	1978-02-23	Dihydro-oxo-nicotinsaeuren und verfahren zu ihrer herstellung
JPS6143183A (ja)	1986-03-01	新規２ｈ‐１‐ベンゾピラン‐２‐オン誘導体、その製法およびこれを含有する抗アレルギー性疾患治療剤
CA2270359A1 (en)	1998-05-07	Benzoaxozole derivative
NO803058L (no)	1981-04-13	Kinazolinderivater.
JP3499569B2 (ja)	2004-02-23	新規複素環式化合物
US4808618A (en)	1989-02-28	Substituted 1,3-dialkylpyrido[4,3-d]pyrimidine-2,4-diones
JPH0533953B2 (da)	1993-05-20
US3420839A (en)	1969-01-07	Aminomethyl pyrazolone derivatives of nicotinamide
JP2001501628A (ja)	2001-02-06	Ｎ―置換化アザ複素環式化合物
JPH037670B2 (da)	1991-02-04
JPS6136754B2 (da)	1986-08-20
NO773047L (no)	1978-03-07	Benzosyrer og fremgangsmaate til deres fremstilling
US6346620B1 (en)	2002-02-12	Methods for preparation of 2-(4-(4-(4,5-dichloro-2-methylimidazol-1-yl)butyl)-1-piperazinyl)-5-fluoropyrimidine and salts thereof