NO125820B - - Google Patents
Download PDFInfo
- Publication number
- NO125820B NO125820B NO70255A NO25570A NO125820B NO 125820 B NO125820 B NO 125820B NO 70255 A NO70255 A NO 70255A NO 25570 A NO25570 A NO 25570A NO 125820 B NO125820 B NO 125820B
- Authority
- NO
- Norway
- Prior art keywords
- pyrimido
- pyrimidine
- bis
- reaction
- groups
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 32
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 claims description 13
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 12
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- CBFFOLYONILLBG-UHFFFAOYSA-N (4,8-dichloro-6-chlorooxysulfanylpyrimido[5,4-d]pyrimidin-2-yl)sulfanyl hypochlorite Chemical compound ClC=1C2=C(N=C(N1)SOCl)C(=NC(=N2)SOCl)Cl CBFFOLYONILLBG-UHFFFAOYSA-N 0.000 claims 1
- HNTHPSUIOUUVCO-UHFFFAOYSA-N 2,6-bis(sulfanylidene)-1,5-dihydropyrimido[5,4-d]pyrimidine-4,8-dione Chemical compound N1C(=S)NC(=O)C2=C1C(=O)NC(=S)N2 HNTHPSUIOUUVCO-UHFFFAOYSA-N 0.000 claims 1
- LNLNOSAYOUJYGD-UHFFFAOYSA-N 4,8-di(piperidin-1-yl)-2,6-bis(piperidin-1-yloxysulfanyl)pyrimido[5,4-d]pyrimidine Chemical compound N1(CCCCC1)C=1C2=C(N=C(N1)SON1CCCCC1)C(=NC(=N2)SON2CCCCC2)N2CCCCC2 LNLNOSAYOUJYGD-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- 229960002768 dipyridamole Drugs 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002887 hydroxy group Chemical class [H]O* 0.000 description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- -1 chlorosulfeno groups Chemical group 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
- C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP546169 | 1969-01-25 | ||
| JP545969 | 1969-01-25 | ||
| JP546069 | 1969-01-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO125820B true NO125820B (ru) | 1972-11-06 |
| NO125820C NO125820C (no) | 1980-02-26 |
Family
ID=27276756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO70255A NO125820C (no) | 1969-01-25 | 1970-01-23 | Fremgangsmaate ved fremstilling av 2,6-bis-(diethanol-amino)-4,8-dipiperidino-pyrimido-(5,4-d)-pyrimidin |
Country Status (3)
| Country | Link |
|---|---|
| DK (1) | DK130979B (ru) |
| NO (1) | NO125820C (ru) |
| SE (1) | SE349302B (ru) |
-
1970
- 1970-01-23 DK DK31070AA patent/DK130979B/da unknown
- 1970-01-23 SE SE00818/70A patent/SE349302B/xx unknown
- 1970-01-23 NO NO70255A patent/NO125820C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK130979B (da) | 1975-05-12 |
| DK130979C (ru) | 1975-10-06 |
| NO125820C (no) | 1980-02-26 |
| SE349302B (ru) | 1972-09-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Broom et al. | Pyrido [2, 3-d] pyrimidines. IV. Synthetic studies leading to various oxopyrido [2, 3-d] pyrimidines | |
| DK141249B (da) | Analogifremgangsmåde til fremstilling af 8-azapurin-6-on-derivater eller salte deraf. | |
| CA1257271A (en) | 6-vinyl-furo-(3,4-c)-pyridine derivatives | |
| Okafor | Heterocyclic series. I. A novel diazaphenothiazine system | |
| SE442867B (sv) | Forfarande for framstellning av karbamidderivat | |
| Itoh et al. | Studies on the chemical synthesis of potential antimetabolites. 30. Regioselective introduction of a chlorine atom into the imidazo [4, 5‐b] pyridine nucleus | |
| NO125820B (ru) | ||
| Itoh et al. | Studies on the Chemical Synthesis of Potential Antimetabolites. 31.1 A Novel Synthesis of 1-Deazaadenosine and Its Conversion to 5′-Deoxy-5′-Isobutylthio-1-Deazaadenosine (1-Deaza-Siba) and S-(1-Deazaadenosyl)-Homocysteine (1-DEAZA-SAH) | |
| Becher et al. | Derivatives and reactions of glutacondialdehyde IV 1-substituted-3-formyl-2 (1H)-pyridinethiones | |
| Taylor et al. | A Facile Pyrimidine Ring Cleavage1, 2 | |
| SU906379A3 (ru) | Способ получени производных пиридо/1,2-а/пиримидинов или их солей,или их оптически активных изомеров | |
| Glennon et al. | Alkylation studies on 6‐ethyl‐2, 3‐dihydrothiazolo‐[3, 2‐A] pyrimidine‐5, 7‐diones | |
| JPS62249991A (ja) | オキサジノベンゾチアジン６，６−ジオキシド誘導体の製造方法 | |
| SU1151210A3 (ru) | Способ получени геминальных дигалоидных производных конденсированных пиримидин-4-онов,рацематов или оптически активных антиподов | |
| JPH0641135A (ja) | イミダゾプテリジン誘導体及びその製造方法 | |
| Monge et al. | Synthesis of pyrido [2, 3‐d] pyrimidin‐4‐one derivatives | |
| US4017490A (en) | Pyrido (3,4-d)pyridazines | |
| CZ288443B6 (en) | Cyclohexane derivatives and use thereof | |
| FI73680B (fi) | Foerfarande foer framstaellning av terapeutiskt verksam 5,11-dihydro-11-/(4-metyl-1-piperazinyl)- acetyl/-6h-pyrido/2,3-b//1,4/benzodiazepin-6-on. | |
| Ikemoto et al. | Large-scale synthesis of new cyclazines, 5-thia-1, 8b-diazaacenaphthylene-3-carboxylic acid derivatives having the peripheral 12π-electron ring system | |
| NO762489L (ru) | ||
| JPS595595B2 (ja) | １５−ヒドロキシイミノ−ｅ−ホモエブルナン誘導体の製造方法 | |
| Hynes et al. | Synthesis of 2‐aminoquinazolines from ortho‐fluoroketones | |
| Woodford et al. | Synthesis of the. alpha. and. beta. anomers of 1-(2-deoxy-D-ribofuranosyl)-4-pyridone | |
| Beccalli et al. | Synthesis and reactivity of 2-dimethylamino-4-alkenyl-1, 3-oxazin-6-ones |