SU479294A3 - Способ получени производных 1,8-нафтиридина - Google Patents
Способ получени производных 1,8-нафтиридинаInfo
- Publication number
- SU479294A3 SU479294A3 SU1951080A SU1951080A SU479294A3 SU 479294 A3 SU479294 A3 SU 479294A3 SU 1951080 A SU1951080 A SU 1951080A SU 1951080 A SU1951080 A SU 1951080A SU 479294 A3 SU479294 A3 SU 479294A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- oil
- preparing
- oxo
- naphthyridine derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 6
- 150000005058 1,8-naphthyridines Chemical class 0.000 title 1
- 239000003921 oil Substances 0.000 description 9
- -1 nirrolidinyl) Chemical group 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- UPQKNTNJVQSGIH-UHFFFAOYSA-N 2,6-dimethylpyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CC=CC2=NC(C)=CC(=O)N21 UPQKNTNJVQSGIH-UHFFFAOYSA-N 0.000 description 1
- KSLLTJJSGWXUMZ-UHFFFAOYSA-N 2,7-dimethyl-1h-1,8-naphthyridin-4-one Chemical compound N1C(C)=CC(=O)C=2C1=NC(C)=CC=2 KSLLTJJSGWXUMZ-UHFFFAOYSA-N 0.000 description 1
- PCISLWUXJKQROS-UHFFFAOYSA-N 3,7-dimethyl-1h-1,8-naphthyridin-4-one Chemical compound N1C=C(C)C(=O)C=2C1=NC(C)=CC=2 PCISLWUXJKQROS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 101100240886 Rattus norvegicus Nptx2 gene Proteins 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- ZLYHSYOPYSDSHB-UHFFFAOYSA-N ethyl 6-methyl-4-oxopyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C1=CC=C(C)N2C(=O)C(C(=O)OCC)=CN=C21 ZLYHSYOPYSDSHB-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
Classifications
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUME001512 HU165405B (enExample) | 1972-06-29 | 1972-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU479294A3 true SU479294A3 (ru) | 1975-07-30 |
Family
ID=10999288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1951080A SU479294A3 (ru) | 1972-06-29 | 1973-06-27 | Способ получени производных 1,8-нафтиридина |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS527000B2 (enExample) |
| BE (1) | BE801669A (enExample) |
| CS (1) | CS184873B1 (enExample) |
| ES (1) | ES416973A1 (enExample) |
| FR (1) | FR2190820B1 (enExample) |
| GB (1) | GB1432967A (enExample) |
| HU (1) | HU165405B (enExample) |
| SU (1) | SU479294A3 (enExample) |
| YU (1) | YU175973A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3644825A1 (de) * | 1986-12-31 | 1988-07-14 | Basf Ag | Substituierte 1,8-naphthyridin-derivate und diese enthaltende fungizide |
| ES2188194T3 (es) * | 1998-08-11 | 2003-06-16 | Pfizer Prod Inc | 1,8-naftiridin-4(1h)-onas sustituidas como inhibidores de la fosfodiesterasa 4. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH66A (de) * | 1889-01-08 | J Kobler | Feueranzünder |
-
1972
- 1972-06-29 HU HUME001512 patent/HU165405B/hu not_active IP Right Cessation
-
1973
- 1973-06-27 SU SU1951080A patent/SU479294A3/ru active
- 1973-06-28 GB GB3089973A patent/GB1432967A/en not_active Expired
- 1973-06-28 JP JP48073235A patent/JPS527000B2/ja not_active Expired
- 1973-06-29 FR FR7323957A patent/FR2190820B1/fr not_active Expired
- 1973-06-29 CS CS474873A patent/CS184873B1/cs unknown
- 1973-06-29 BE BE132909A patent/BE801669A/xx not_active IP Right Cessation
- 1973-06-30 ES ES416973A patent/ES416973A1/es not_active Expired
- 1973-07-28 YU YU175973A patent/YU175973A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE801669A (fr) | 1973-10-15 |
| FR2190820A1 (enExample) | 1974-02-01 |
| ES416973A1 (es) | 1976-03-16 |
| FR2190820B1 (enExample) | 1976-06-18 |
| CS184873B1 (en) | 1978-09-15 |
| HU165405B (enExample) | 1974-08-28 |
| JPS527000B2 (enExample) | 1977-02-26 |
| JPS4962498A (enExample) | 1974-06-17 |
| YU175973A (en) | 1982-05-31 |
| GB1432967A (enExample) | 1976-04-22 |
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