JPS5929595B2 - ピリミジン誘導体の製法 - Google Patents
ピリミジン誘導体の製法Info
- Publication number
- JPS5929595B2 JPS5929595B2 JP50030976A JP3097675A JPS5929595B2 JP S5929595 B2 JPS5929595 B2 JP S5929595B2 JP 50030976 A JP50030976 A JP 50030976A JP 3097675 A JP3097675 A JP 3097675A JP S5929595 B2 JPS5929595 B2 JP S5929595B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidine
- formula
- oxo
- reaction
- dihydropyrido
- 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
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- BYTRPZLYYIPRLJ-UHFFFAOYSA-N 8h-pyrido[2,3-d]pyrimidin-5-one Chemical compound C1=NC=C2C(O)=CC=NC2=N1 BYTRPZLYYIPRLJ-UHFFFAOYSA-N 0.000 claims 2
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 17
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 229960005141 piperazine Drugs 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 150000003457 sulfones Chemical class 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229960003506 piperazine hexahydrate Drugs 0.000 description 3
- AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 3
- 150000004885 piperazines Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003647 oxidation 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
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- ZFAMWXWGOVVLJU-UHFFFAOYSA-N ethyl 8-ethyl-2-methylsulfonyl-5-oxopyrido[2,3-d]pyrimidine-6-carboxylate Chemical compound CS(=O)(=O)C=1N=CC2=C(N1)N(C=C(C2=O)C(=O)OCC)CC ZFAMWXWGOVVLJU-UHFFFAOYSA-N 0.000 description 1
- GREJMFIZXZNREA-UHFFFAOYSA-N ethyl 8-ethyl-5-oxo-2-piperazin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylate Chemical compound N=1C=C2C(=O)C(C(=O)OCC)=CN(CC)C2=NC=1N1CCNCC1 GREJMFIZXZNREA-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005303 weighing 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11538/74A GB1484138A (en) | 1974-03-14 | 1974-03-14 | Pyrido pyrimidine derivatives |
| GB1153874 | 1974-03-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50129596A JPS50129596A (xx) | 1975-10-13 |
| JPS5929595B2 true JPS5929595B2 (ja) | 1984-07-21 |
Family
ID=9988077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50030976A Expired JPS5929595B2 (ja) | 1974-03-14 | 1975-03-14 | ピリミジン誘導体の製法 |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5929595B2 (xx) |
| CA (1) | CA1038870A (xx) |
| CH (1) | CH603642A5 (xx) |
| CS (1) | CS193510B2 (xx) |
| DD (2) | DD123606A5 (xx) |
| DK (1) | DK152497C (xx) |
| FR (2) | FR2299336A1 (xx) |
| GB (1) | GB1484138A (xx) |
| IN (1) | IN141366B (xx) |
| NL (1) | NL7503113A (xx) |
| RO (1) | RO65404A (xx) |
| SE (1) | SE7502845L (xx) |
| YU (1) | YU39114B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3326118A1 (de) | 1982-08-02 | 1984-02-09 | Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz | Pyridopyrimidintrione, verfahren zu ihrer herstellung, ihre verwendung und sie enthaltende arzneimittel |
| NZ210847A (en) * | 1984-01-26 | 1988-02-29 | Abbott Lab | Naphthyridine and pyridopyrimidine derivatives and pharmaceutical compositions |
| US4851535A (en) * | 1985-01-23 | 1989-07-25 | Toyama Chemical Co., Ltd. | Nicotinic acid derivatives |
| JP2000232222A (ja) * | 1999-02-10 | 2000-08-22 | Nec Corp | 半導体装置の製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2341146A1 (de) * | 1972-08-14 | 1974-02-28 | Dainippon Pharmaceutical Co | Piperazinderivate sowie verfahren zu deren herstellung und anwendung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2194420B1 (xx) * | 1972-08-02 | 1975-10-17 | Bellon Labor Sa Roger |
-
1974
- 1974-03-14 GB GB11538/74A patent/GB1484138A/en not_active Expired
-
1975
- 1975-02-27 FR FR7506182A patent/FR2299336A1/fr active Granted
- 1975-03-12 DK DK100275A patent/DK152497C/da not_active IP Right Cessation
- 1975-03-12 YU YU00600/75A patent/YU39114B/xx unknown
- 1975-03-12 IN IN482/CAL/75A patent/IN141366B/en unknown
- 1975-03-12 RO RO7581614A patent/RO65404A/ro unknown
- 1975-03-13 SE SE7502845A patent/SE7502845L/xx unknown
- 1975-03-14 CH CH330175A patent/CH603642A5/xx not_active IP Right Cessation
- 1975-03-14 CS CS751747A patent/CS193510B2/cs unknown
- 1975-03-14 NL NL7503113A patent/NL7503113A/xx active Search and Examination
- 1975-03-14 DD DD191319A patent/DD123606A5/xx unknown
- 1975-03-14 DD DD184793A patent/DD120021A5/xx unknown
- 1975-03-14 CA CA222,321A patent/CA1038870A/en not_active Expired
- 1975-03-14 JP JP50030976A patent/JPS5929595B2/ja not_active Expired
-
1976
- 1976-01-12 FR FR7600593A patent/FR2289507A1/fr active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2341146A1 (de) * | 1972-08-14 | 1974-02-28 | Dainippon Pharmaceutical Co | Piperazinderivate sowie verfahren zu deren herstellung und anwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2289507A1 (fr) | 1976-05-28 |
| YU39114B (en) | 1984-06-30 |
| DD123606A5 (xx) | 1977-01-05 |
| IN141366B (xx) | 1977-02-19 |
| FR2299336A1 (fr) | 1976-08-27 |
| DK152497C (da) | 1988-08-01 |
| CA1038870A (en) | 1978-09-19 |
| DD120021A5 (xx) | 1976-05-20 |
| DK152497B (da) | 1988-03-07 |
| JPS50129596A (xx) | 1975-10-13 |
| NL7503113A (nl) | 1975-09-16 |
| CH603642A5 (xx) | 1978-08-31 |
| SE7502845L (xx) | 1975-09-15 |
| CS193510B2 (en) | 1979-10-31 |
| DK100275A (xx) | 1975-09-15 |
| GB1484138A (en) | 1977-08-24 |
| RO65404A (ro) | 1980-06-15 |
| FR2299336B1 (xx) | 1979-03-30 |
| FR2289507B1 (xx) | 1978-11-10 |
| YU60075A (en) | 1982-02-28 |
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