SU567409A3 - Способ получени производных 1,8-нафтиридина 1 - Google Patents
Способ получени производных 1,8-нафтиридина 1Info
- Publication number
- SU567409A3 SU567409A3 SU742093429A SU2093429A SU567409A3 SU 567409 A3 SU567409 A3 SU 567409A3 SU 742093429 A SU742093429 A SU 742093429A SU 2093429 A SU2093429 A SU 2093429A SU 567409 A3 SU567409 A3 SU 567409A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- oxo
- naphthyridine
- dihydro
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 35
- -1 1 - ethyl - 7 - methyl - 4-oxo - 1, 4 - dihydro - 1, 8 - naphthyridine - 3 carbonyl - ( benzylmethyl isoquinoline) - iodide Chemical compound 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 41
- 239000011541 reaction mixture Substances 0.000 claims description 38
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 36
- 229910052740 iodine Inorganic materials 0.000 claims description 36
- 239000011630 iodine Substances 0.000 claims description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 24
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- FGFJOULNUAEAAQ-UHFFFAOYSA-N 1-ethyl-7-methyl-1,8-naphthyridin-4-one Chemical compound C1=C(C)N=C2N(CC)C=CC(=O)C2=C1 FGFJOULNUAEAAQ-UHFFFAOYSA-N 0.000 claims description 5
- MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 claims description 5
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims description 4
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 125000005270 trialkylamine group Chemical group 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 8
- 239000000047 product Substances 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 239000013078 crystal Substances 0.000 claims 4
- 238000010438 heat treatment Methods 0.000 claims 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- WIZNBODWFXTVAP-UHFFFAOYSA-N 1-ethyl-7-methyl-3-(2-methylpropanoyl)-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(C(C)C)=O WIZNBODWFXTVAP-UHFFFAOYSA-N 0.000 claims 2
- IMNUYXFNLOVWEF-UHFFFAOYSA-N 3-(2-cyclohexylacetyl)-1-ethyl-7-methyl-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CC1CCCCC1)=O IMNUYXFNLOVWEF-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Chemical group 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- LHASZEBEQGPCFM-CJFMBICVSA-N 2-amino-4-[(1r)-1-[[(6r)-6-[(5-chloro-2-methoxyphenyl)methyl]-7-oxo-3-(phenoxyamino)-5,6-dihydro-2h-1,4-diazepine-1-carbonyl]amino]propyl]benzoic acid Chemical compound C([C@@H]1CNC(CN(C1=O)C(=O)N[C@H](CC)C=1C=C(N)C(C(O)=O)=CC=1)=NOC=1C=CC=CC=1)C1=CC(Cl)=CC=C1OC LHASZEBEQGPCFM-CJFMBICVSA-N 0.000 claims 1
- WONYMNWUJVKVII-UHFFFAOYSA-N 3,5-diiodothyropropionic acid Chemical compound IC1=CC(CCC(=O)O)=CC(I)=C1OC1=CC=C(O)C=C1 WONYMNWUJVKVII-UHFFFAOYSA-N 0.000 claims 1
- LSUQPHPXYPEBRM-UHFFFAOYSA-N 3-(2-bromo-2-methylpropanoyl)-1-ethyl-7-methyl-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(C(C)(C)Br)=O LSUQPHPXYPEBRM-UHFFFAOYSA-N 0.000 claims 1
- OXBLYVNAOSSJAC-UHFFFAOYSA-N 3-acetyl-7-methyl-1h-1,8-naphthyridin-4-one Chemical compound CC1=CC=C2C(=O)C(C(=O)C)=CNC2=N1 OXBLYVNAOSSJAC-UHFFFAOYSA-N 0.000 claims 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims 1
- JVJJTRYGAHJGAZ-UHFFFAOYSA-N 7-methyl-1h-1,8-naphthyridin-4-one Chemical compound N1C=CC(=O)C=2C1=NC(C)=CC=2 JVJJTRYGAHJGAZ-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- LNQCUTNLHUQZLR-VNPYQEQNSA-N Iridin Natural products O(C)c1c(O)c2C(=O)C(c3cc(OC)c(OC)c(O)c3)=COc2cc1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 LNQCUTNLHUQZLR-VNPYQEQNSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 108010047623 iridine Proteins 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical group Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 claims 1
- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- CYDFIAGFVIGXQJ-UHFFFAOYSA-N 1-ethyl-7-methyl-3-propanoyl-1,8-naphthyridin-4-one Chemical compound CC1=CC=C2C(=O)C(C(=O)CC)=CN(CC)C2=N1 CYDFIAGFVIGXQJ-UHFFFAOYSA-N 0.000 description 3
- FQDNITWZGPQXBT-UHFFFAOYSA-N 1-ethyl-7-methyl-3-pentanoyl-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCCC)=O FQDNITWZGPQXBT-UHFFFAOYSA-N 0.000 description 2
- MUDSDYNRBDKLGK-UHFFFAOYSA-N 4-methylquinoline Chemical compound C1=CC=C2C(C)=CC=NC2=C1 MUDSDYNRBDKLGK-UHFFFAOYSA-N 0.000 description 2
- HSOQBSYABQUNQV-UHFFFAOYSA-N 1,4-dihydro-1,8-naphthyridine Chemical compound C1=CC=C2CC=CNC2=N1 HSOQBSYABQUNQV-UHFFFAOYSA-N 0.000 description 1
- BDZKTYWLUIQPBK-UHFFFAOYSA-N 1-ethyl-7-methyl-3-(2-phenylacetyl)-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CC1=CC=CC=C1)=O BDZKTYWLUIQPBK-UHFFFAOYSA-N 0.000 description 1
- ZPVXFTFVNMMWJX-UHFFFAOYSA-N 1-ethyl-7-methyl-3-(3-phenylpropanoyl)-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCC1=CC=CC=C1)=O ZPVXFTFVNMMWJX-UHFFFAOYSA-N 0.000 description 1
- ICZPXVNCDPEYSR-UHFFFAOYSA-N 3-butanoyl-1-ethyl-7-methyl-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCC)=O ICZPXVNCDPEYSR-UHFFFAOYSA-N 0.000 description 1
- XZOVCSPCZQGKJD-UHFFFAOYSA-N C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCC1CCCCC1)=O Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCC1CCCCC1)=O XZOVCSPCZQGKJD-UHFFFAOYSA-N 0.000 description 1
- RRAGFJYAIIPFDY-UHFFFAOYSA-M CCN(C=C1C(C2=[N+](CCC3=CC=CC=C3)C=CC=C2)=O)C2=NC(C)=CC=C2C1=O.[I-] Chemical compound CCN(C=C1C(C2=[N+](CCC3=CC=CC=C3)C=CC=C2)=O)C2=NC(C)=CC=C2C1=O.[I-] RRAGFJYAIIPFDY-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- YDQJXVYGARVLRT-UHFFFAOYSA-N Lepidine Natural products C=1C=CC(CC=2NC=CN=2)=CC=1OC=1C(OC)=CC=CC=1CC1=NC=CN1 YDQJXVYGARVLRT-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU73CI00001430A HU171561B (hu) | 1973-12-29 | 1973-12-29 | Sposob poluchenija proizvodnykh 1,8-naftiridina |
| JP49007604A JPS50100092A (enrdf_load_stackoverflow) | 1973-12-29 | 1974-01-17 | |
| HU74CI00001521A HU171868B (hu) | 1974-01-17 | 1974-12-04 | Sposob poluchenija novykh proizvodnykh 1,8-naftiridina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU567409A3 true SU567409A3 (ru) | 1977-07-30 |
Family
ID=27270157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU742093429A SU567409A3 (ru) | 1973-12-29 | 1974-12-27 | Способ получени производных 1,8-нафтиридина 1 |
Country Status (13)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9023289D0 (en) * | 1990-10-25 | 1990-12-05 | Ici Plc | Herbicides |
-
1974
- 1974-01-01 AR AR257146A patent/AR207854A1/es active
- 1974-12-23 DK DK677474A patent/DK677474A/da not_active Application Discontinuation
- 1974-12-24 CH CH1730474A patent/CH617198A5/de not_active IP Right Cessation
- 1974-12-24 GB GB55871/74A patent/GB1493948A/en not_active Expired
- 1974-12-27 CA CA217,001A patent/CA1053234A/en not_active Expired
- 1974-12-27 NL NL7416923A patent/NL7416923A/xx not_active Application Discontinuation
- 1974-12-27 SE SE7416321A patent/SE7416321L/xx unknown
- 1974-12-27 NO NO744715A patent/NO744715L/no unknown
- 1974-12-27 SU SU742093429A patent/SU567409A3/ru active
- 1974-12-27 FI FI3757/74A patent/FI375774A7/fi unknown
- 1974-12-28 ES ES433690A patent/ES433690A1/es not_active Expired
- 1974-12-30 DD DD183435A patent/DD115905A5/xx unknown
- 1974-12-30 BG BG030116A patent/BG23898A3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE7416321L (enrdf_load_stackoverflow) | 1975-06-30 |
| CH617198A5 (en) | 1980-05-14 |
| ES433690A1 (es) | 1977-04-16 |
| GB1493948A (en) | 1977-11-30 |
| NO744715L (enrdf_load_stackoverflow) | 1975-07-28 |
| NL7416923A (nl) | 1975-07-01 |
| BG23898A3 (bg) | 1977-11-10 |
| DK677474A (enrdf_load_stackoverflow) | 1975-09-01 |
| FI375774A7 (enrdf_load_stackoverflow) | 1975-06-30 |
| CA1053234A (en) | 1979-04-24 |
| DD115905A5 (enrdf_load_stackoverflow) | 1975-10-20 |
| AR207854A1 (es) | 1976-11-08 |
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