KR850001168A - 디하이드로 피리딘 유도체의 제조방법 - Google Patents
디하이드로 피리딘 유도체의 제조방법 Download PDFInfo
- Publication number
- KR850001168A KR850001168A KR1019840004373A KR840004373A KR850001168A KR 850001168 A KR850001168 A KR 850001168A KR 1019840004373 A KR1019840004373 A KR 1019840004373A KR 840004373 A KR840004373 A KR 840004373A KR 850001168 A KR850001168 A KR 850001168A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- group
- amino
- alkyl
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims 8
- 125000004925 dihydropyridyl group Chemical class N1(CC=CC=C1)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 24
- -1 2-substituted -4-pyrimidone group Chemical group 0.000 claims 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical group OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- VUUOPBGYSXFRKK-UHFFFAOYSA-N 2-aminoimidazol-4-one Chemical group NC1=NC(=O)C=N1 VUUOPBGYSXFRKK-UHFFFAOYSA-N 0.000 claims 2
- RDNKSCGYGQALIZ-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-5-amine Chemical group NC1CNC=N1 RDNKSCGYGQALIZ-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- QEASJVYPHMYPJM-UHFFFAOYSA-N 1,2-dihydrotriazol-5-one Chemical compound OC1=CNN=N1 QEASJVYPHMYPJM-UHFFFAOYSA-N 0.000 claims 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical group O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims 1
- AHQSDTAPZOQQBJ-UHFFFAOYSA-N 2,3-dimethylpyrimidin-4-one Chemical compound CC1=NC=CC(=O)N1C AHQSDTAPZOQQBJ-UHFFFAOYSA-N 0.000 claims 1
- XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical compound NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- DPLBVYHGXCMXPW-UHFFFAOYSA-N 2-methyl-2,5-dihydro-1h-imidazole Chemical group CC1NCC=N1 DPLBVYHGXCMXPW-UHFFFAOYSA-N 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- BKPALOYSZUJHHW-UHFFFAOYSA-N 3-methyl-2,4-dioxo-1H-pyrimidine-5-carbonitrile Chemical group C(#N)C=1C(N(C(NC1)=O)C)=O BKPALOYSZUJHHW-UHFFFAOYSA-N 0.000 claims 1
- VORRZXJVDONPFR-UHFFFAOYSA-N 3-o-ethyl 5-o-methyl 4-(2,3-dichlorophenyl)-2-[(1,2-dimethyl-6-oxopyrimidin-4-yl)methoxymethyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound N1C(C)=C(C(=O)OC)C(C=2C(=C(Cl)C=CC=2)Cl)C(C(=O)OCC)=C1COCC1=CC(=O)N(C)C(C)=N1 VORRZXJVDONPFR-UHFFFAOYSA-N 0.000 claims 1
- ZMLJHXQHPNGPJP-UHFFFAOYSA-N 4-aminoimidazol-2-one Chemical compound NC1=NC(=O)N=C1 ZMLJHXQHPNGPJP-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004802 cyanophenyl group Chemical group 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- OAHGTHONFSMECO-UHFFFAOYSA-N ethyl 2-(bromomethyl)pyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=CN=C1CBr OAHGTHONFSMECO-UHFFFAOYSA-N 0.000 claims 1
- XLXALEMGVGAONO-UHFFFAOYSA-N ethyl 5-oxo-1,2-dihydrotriazole-4-carboxylate Chemical group CCOC(=O)C=1N=NNC=1O XLXALEMGVGAONO-UHFFFAOYSA-N 0.000 claims 1
- ORCYLAFTPRKFRY-UHFFFAOYSA-N ethyl n-(2-cyano-3-ethoxyprop-2-enoyl)-n-methylcarbamate Chemical compound CCOC=C(C#N)C(=O)N(C)C(=O)OCC ORCYLAFTPRKFRY-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838319886A GB8319886D0 (en) | 1983-07-23 | 1983-07-23 | Therapeutic agents |
| GB8319886 | 1983-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR850001168A true KR850001168A (ko) | 1985-03-16 |
Family
ID=10546182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004373A Ceased KR850001168A (ko) | 1983-07-23 | 1984-07-23 | 디하이드로 피리딘 유도체의 제조방법 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS6042380A (enrdf_load_stackoverflow) |
| KR (1) | KR850001168A (enrdf_load_stackoverflow) |
| GB (1) | GB8319886D0 (enrdf_load_stackoverflow) |
| ZA (1) | ZA845619B (enrdf_load_stackoverflow) |
-
1983
- 1983-07-23 GB GB838319886A patent/GB8319886D0/en active Pending
-
1984
- 1984-07-20 ZA ZA845619A patent/ZA845619B/xx unknown
- 1984-07-23 JP JP59152749A patent/JPS6042380A/ja active Granted
- 1984-07-23 KR KR1019840004373A patent/KR850001168A/ko not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0321552B2 (enrdf_load_stackoverflow) | 1991-03-22 |
| GB8319886D0 (en) | 1983-08-24 |
| ZA845619B (en) | 1986-02-26 |
| JPS6042380A (ja) | 1985-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19840723 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19860430 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19840723 Comment text: Patent Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19871231 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 19880630 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 19871231 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |
|
| J2X1 | Appeal (before the patent court) |
Free format text: APPEAL AGAINST DECISION TO DECLINE REFUSAL |
|
| PJ2001 | Appeal |
Appeal kind category: Appeal against decision to decline refusal Decision date: 19890630 Appeal identifier: 1988201000812 Request date: 19880929 |
|
| J2X2 | Appeal (before the supreme court) |
Free format text: APPEAL BEFORE THE SUPREME COURT FOR APPEAL AGAINST DECISION TO DECLINE REFUSAL |
|
| PJ2002 | Appeal before the supreme court |
Request date: 19890804 Appeal identifier: 1989301001387 Appeal kind category: Appeal against decision to decline refusal Decision date: 19900112 |