DE1670522C3 - Neue Benzylaminopyridine - Google Patents
Neue BenzylaminopyridineInfo
- Publication number
- DE1670522C3 DE1670522C3 DE1670522A DED0050092A DE1670522C3 DE 1670522 C3 DE1670522 C3 DE 1670522C3 DE 1670522 A DE1670522 A DE 1670522A DE D0050092 A DED0050092 A DE D0050092A DE 1670522 C3 DE1670522 C3 DE 1670522C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- amino
- compounds
- pyridine
- radical
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- WYHXNQXDQQMTQI-UHFFFAOYSA-N n-benzylpyridin-2-amine Chemical class C=1C=CC=CC=1CNC1=CC=CC=N1 WYHXNQXDQQMTQI-UHFFFAOYSA-N 0.000 title claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 13
- 238000005984 hydrogenation reaction Methods 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- -1 unsaturated aliphatic mono- Chemical class 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 5
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000007868 Raney catalyst Substances 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000001760 anti-analgesic effect Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 239000002274 desiccant Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 1
- 235000019341 magnesium sulphate Nutrition 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 235000011150 stannous chloride Nutrition 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 9
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 8
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 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 description 2
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- PHMOFWOJSMWUGB-UHFFFAOYSA-N 6-n-[(2-chlorophenyl)methyl]-3-nitropyridine-2,6-diamine Chemical compound C1=C([N+]([O-])=O)C(N)=NC(NCC=2C(=CC=CC=2)Cl)=C1 PHMOFWOJSMWUGB-UHFFFAOYSA-N 0.000 description 1
- QFSFMLULADNGGX-UHFFFAOYSA-N 6-n-[(4-chlorophenyl)methyl]-3-nitropyridine-2,6-diamine Chemical compound C1=C([N+]([O-])=O)C(N)=NC(NCC=2C=CC(Cl)=CC=2)=C1 QFSFMLULADNGGX-UHFFFAOYSA-N 0.000 description 1
- HGKJZWUGYTUZPG-UHFFFAOYSA-N 6-n-[(4-methoxyphenyl)methyl]-3-nitropyridine-2,6-diamine Chemical compound C1=CC(OC)=CC=C1CNC1=CC=C([N+]([O-])=O)C(N)=N1 HGKJZWUGYTUZPG-UHFFFAOYSA-N 0.000 description 1
- PFLADTNUVCOSHZ-UHFFFAOYSA-N 6-n-[(4-methylphenyl)methyl]-3-nitropyridine-2,6-diamine Chemical compound C1=CC(C)=CC=C1CNC1=CC=C([N+]([O-])=O)C(N)=N1 PFLADTNUVCOSHZ-UHFFFAOYSA-N 0.000 description 1
- RAGAMBSCSBOXBU-UHFFFAOYSA-N 6-n-benzyl-3-nitropyridine-2,6-diamine Chemical compound C1=C([N+]([O-])=O)C(N)=NC(NCC=2C=CC=CC=2)=C1 RAGAMBSCSBOXBU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SWZATAOGLHBHPO-UHFFFAOYSA-N ethyl N-[2-amino-6-[(4-methoxyphenyl)methylamino]pyridin-3-yl]carbamate Chemical compound NC1=NC(=CC=C1NC(=O)OCC)NCC1=CC=C(C=C1)OC SWZATAOGLHBHPO-UHFFFAOYSA-N 0.000 description 1
- WIIRVBMXQPXRDJ-UHFFFAOYSA-N ethyl N-[2-amino-6-[(4-methylphenyl)methylamino]pyridin-3-yl]carbamate Chemical compound CCOC(=O)Nc1ccc(NCc2ccc(C)cc2)nc1N WIIRVBMXQPXRDJ-UHFFFAOYSA-N 0.000 description 1
- TTXXOPWBRNPYER-UHFFFAOYSA-N ethyl n-[2-amino-6-(benzylamino)pyridin-3-yl]carbamate Chemical compound N1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=CC=C1 TTXXOPWBRNPYER-UHFFFAOYSA-N 0.000 description 1
- FXSAHGOZUTYHOI-UHFFFAOYSA-N ethyl n-[2-amino-6-[(2,4-dimethylphenyl)methylamino]pyridin-3-yl]carbamate Chemical compound N1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C)C=C1C FXSAHGOZUTYHOI-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19661670523 DE1670523A1 (de) | 1966-05-12 | 1966-05-12 | Verfahren zur Herstellung neuer substituierter Aminopyridine |
| DE1670522A DE1670522C3 (de) | 1966-05-12 | 1966-05-12 | Neue Benzylaminopyridine |
| SE05990/67A SE360866B (ref) | 1966-05-12 | 1967-04-27 | |
| NL676705973A NL139972B (nl) | 1966-05-12 | 1967-04-27 | Werkwijze ter bereiding van een geneesmiddel met antiflogistische en analgetische werking. |
| ES340336A ES340336A2 (es) | 1966-05-12 | 1967-05-10 | Un procedimiento para la preparacion de compuestos de valorterapeutico. |
| US637322A US3481943A (en) | 1966-05-12 | 1967-05-10 | Benzyl and pyridylmethyl substituted amido amino pyridines |
| CH666367A CH555828A (de) | 1966-05-12 | 1967-05-11 | Verfahren zur herstellung neuer substituierter aminopyridine. |
| BE698384D BE698384A (ref) | 1966-05-12 | 1967-05-11 | |
| DK248867AA DK119978B (da) | 1966-05-12 | 1967-05-11 | Analogifremgangsmåde til fremstilling af substituerede aminopyridiner eller salte deraf. |
| CH666467A CH502339A (de) | 1966-05-12 | 1967-05-11 | Verfahren zur Herstellung neuer substituierter Aminopyridine |
| FI671370A FI49301C (fi) | 1966-05-12 | 1967-05-12 | Menetelmä uusien substituoitujen aminopyridiinien valmistamiseksi, joi lla on tulehduksenvastainen ja kipua lieventävä vaikutus. |
| GB22222/67A GB1191302A (en) | 1966-05-12 | 1967-05-12 | New Substituted Aminopyridines and processes for preparing them |
| FR105743A FR6877M (ref) | 1966-05-12 | 1967-07-11 | |
| FR168040A FR306F (ref) | 1966-05-12 | 1968-09-27 | |
| US845058A US3513171A (en) | 1966-05-12 | 1969-07-25 | Certain substituted benzyl pyridyl-methyl derivatives of 2-,3- or 4-pyridyl carbamates |
| BE764362A BE764362R (en) | 1966-05-12 | 1971-03-16 | Subst amino pyridienes production |
| IN1986/CAL/75A IN143114B (ref) | 1966-05-12 | 1975-10-10 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1670522A DE1670522C3 (de) | 1966-05-12 | 1966-05-12 | Neue Benzylaminopyridine |
| DED0050093 | 1966-05-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1670522A1 DE1670522A1 (de) | 1970-11-12 |
| DE1670522B2 DE1670522B2 (de) | 1977-12-15 |
| DE1670522C3 true DE1670522C3 (de) | 1978-08-31 |
Family
ID=25972357
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1670522A Expired DE1670522C3 (de) | 1966-05-12 | 1966-05-12 | Neue Benzylaminopyridine |
| DE19661670523 Pending DE1670523A1 (de) | 1966-05-12 | 1966-05-12 | Verfahren zur Herstellung neuer substituierter Aminopyridine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661670523 Pending DE1670523A1 (de) | 1966-05-12 | 1966-05-12 | Verfahren zur Herstellung neuer substituierter Aminopyridine |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US3481943A (ref) |
| BE (1) | BE698384A (ref) |
| CH (2) | CH555828A (ref) |
| DE (2) | DE1670522C3 (ref) |
| DK (1) | DK119978B (ref) |
| ES (1) | ES340336A2 (ref) |
| FI (1) | FI49301C (ref) |
| FR (1) | FR6877M (ref) |
| GB (1) | GB1191302A (ref) |
| NL (1) | NL139972B (ref) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000816A1 (en) * | 1977-08-06 | 1979-02-21 | Beecham Group Plc | Substituted amino-pyridine derivatives, processes for their preparation and pharmaceutical compositions containing them |
| DE3369315D1 (en) * | 1982-10-27 | 1987-02-26 | Degussa | Derivatives of 2-amino-3-acylamino-6-benzylamino pyridine with an anti-epileptic activity |
| IL74375A (en) * | 1984-02-21 | 1988-02-29 | Lilly Co Eli | Process for preparing diaminopyridines via hydrogenation of nitrobenzylamino-pyridines |
| NO860825L (no) * | 1985-03-23 | 1986-09-24 | Degussa | Fremgangsmaate til fremstilling av 2-amino-3-nitro-6-(4-fluor-benzylamino)-pyridin samt 2-amino-3-karbetoksyamino-6-(4-fluor-benzylamino)-pyridin. |
| MC2029A1 (fr) * | 1988-05-16 | 1990-04-25 | Asta Pharma Ag | (n-heterocyclyl)-3 diamino-2,6 pyridines substituees et leurs n-oxydes,preparation de ces composes et leur application comme medicaments |
| US6022884A (en) | 1997-11-07 | 2000-02-08 | Amgen Inc. | Substituted pyridine compounds and methods of use |
| EP1688141A1 (en) * | 2005-01-31 | 2006-08-09 | elbion AG | The use of flupirtine for the treatment of overactive bladder and associated diseases, and for the treatment of irritable bowel syndrome |
| US20080279930A1 (en) * | 2007-05-07 | 2008-11-13 | Bernd Terhaag | Controlled-Release Flupirtine Compositions, Compacts, Kits and Methods of Making and Use Thereof |
| CN102241626B (zh) * | 2011-05-03 | 2013-07-03 | 北京华睿鼎信科技有限公司 | 一种马来酸氟吡汀的合成工艺 |
| CN102850265B (zh) * | 2011-06-29 | 2015-11-25 | 陈小花 | 一种氟吡汀偶联物及其制备方法和用途 |
| CN102351786A (zh) * | 2011-11-01 | 2012-02-15 | 东南大学 | 一种氟吡汀丙二酸盐及其制备方法 |
| WO2013080215A1 (en) | 2011-11-30 | 2013-06-06 | Arch Pharmalabs Limited | An improved process for the preparation of flupirtine and pharmaceutically acceptable salts thereof |
| CN103910674B (zh) * | 2013-12-19 | 2015-12-02 | 天津红日药业股份有限公司 | 用于马来酸氟吡汀分析中的参比化合物 |
| WO2019014547A1 (en) * | 2017-07-14 | 2019-01-17 | Texas Tech University System | FUNCTIONALIZED PYRIDINE CARBAMATES HAVING ENHANCED NEUROPROTECTOR ACTIVITY |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL132603C (ref) * | 1964-08-29 | |||
| FR1462263A (fr) * | 1964-08-29 | 1966-04-15 | Degussa | Procédé de préparation de nouvelles diaminopyridines substituées |
-
1966
- 1966-05-12 DE DE1670522A patent/DE1670522C3/de not_active Expired
- 1966-05-12 DE DE19661670523 patent/DE1670523A1/de active Pending
-
1967
- 1967-04-27 NL NL676705973A patent/NL139972B/xx not_active IP Right Cessation
- 1967-05-10 ES ES340336A patent/ES340336A2/es not_active Expired
- 1967-05-10 US US637322A patent/US3481943A/en not_active Expired - Lifetime
- 1967-05-11 CH CH666367A patent/CH555828A/xx not_active IP Right Cessation
- 1967-05-11 BE BE698384D patent/BE698384A/xx unknown
- 1967-05-11 CH CH666467A patent/CH502339A/de not_active IP Right Cessation
- 1967-05-11 DK DK248867AA patent/DK119978B/da unknown
- 1967-05-12 GB GB22222/67A patent/GB1191302A/en not_active Expired
- 1967-05-12 FI FI671370A patent/FI49301C/fi active
- 1967-07-11 FR FR105743A patent/FR6877M/fr not_active Expired
-
1969
- 1969-07-25 US US845058A patent/US3513171A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BE698384A (ref) | 1967-10-16 |
| FI49301B (ref) | 1975-01-31 |
| CH555828A (de) | 1974-11-15 |
| DE1670522B2 (de) | 1977-12-15 |
| GB1191302A (en) | 1970-05-13 |
| FI49301C (fi) | 1975-05-12 |
| NL139972B (nl) | 1973-10-15 |
| DE1670522A1 (de) | 1970-11-12 |
| NL6705973A (ref) | 1967-11-13 |
| CH502339A (de) | 1971-01-31 |
| US3513171A (en) | 1970-05-19 |
| US3481943A (en) | 1969-12-02 |
| ES340336A2 (es) | 1968-06-01 |
| FR6877M (ref) | 1969-04-14 |
| DK119978B (da) | 1971-03-22 |
| DE1670523A1 (de) | 1970-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |