DE2014978A1 - Pyrido eckige Klammer auf 2,3 d eckige Klammer zu pynmidin 4(3H) one und Verfahren zur Herstellung derselben - Google Patents
Pyrido eckige Klammer auf 2,3 d eckige Klammer zu pynmidin 4(3H) one und Verfahren zur Herstellung derselbenInfo
- Publication number
- DE2014978A1 DE2014978A1 DE19702014978 DE2014978A DE2014978A1 DE 2014978 A1 DE2014978 A1 DE 2014978A1 DE 19702014978 DE19702014978 DE 19702014978 DE 2014978 A DE2014978 A DE 2014978A DE 2014978 A1 DE2014978 A1 DE 2014978A1
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- general formula
- pyrido
- group
- square bracket
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000002934 diuretic Substances 0.000 claims description 4
- 230000001882 diuretic effect Effects 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- XKEBMWRWBWRQAO-UHFFFAOYSA-N 1h-pyrido[2,3-d]pyrimidin-4-one Chemical class C1=CC=C2C(=O)N=CNC2=N1 XKEBMWRWBWRQAO-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 230000029142 excretion Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- DVTKOFMIBKSVCJ-UHFFFAOYSA-N 2-chloro-1h-pyrido[2,3-d]pyrimidin-4-one Chemical compound C1=CN=C2NC(Cl)=NC(=O)C2=C1 DVTKOFMIBKSVCJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000001452 natriuretic effect Effects 0.000 description 2
- 229910001414 potassium ion Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- -1 β-Hydroxy-ethoxy Chemical group 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702014978 DE2014978A1 (de) | 1970-03-28 | 1970-03-28 | Pyrido eckige Klammer auf 2,3 d eckige Klammer zu pynmidin 4(3H) one und Verfahren zur Herstellung derselben |
| US00122497A US3804835A (en) | 1970-03-28 | 1971-03-09 | Pyrido(2,3-d)pyrimidin-4-(3h)-ones |
| ES389458A ES389458A1 (es) | 1970-03-28 | 1971-03-23 | Procedimiento para la preparacion de pirido (2,3-d) pirimi-din-4-(3h)-onas. |
| FR7110521A FR2085750B1 (OSRAM) | 1970-03-28 | 1971-03-25 | |
| SE03963/71A SE362248B (OSRAM) | 1970-03-28 | 1971-03-26 | |
| AT261671A AT304559B (de) | 1970-03-28 | 1971-03-26 | Verfahren zur Herstellung von neuen Pyrido[2,3-d]pyrimidin-4(3H)-onen und ihren Salzen |
| HUBO1284A HU162214B (OSRAM) | 1970-03-28 | 1971-03-26 | |
| NL7104092A NL7104092A (OSRAM) | 1970-03-28 | 1971-03-26 | |
| ZA711967A ZA711967B (en) | 1970-03-28 | 1971-03-26 | New pyrido-(2,3-d)pyrimidin-4(3h)-ones and the preparation thereof |
| GB25366/71A GB1285170A (en) | 1970-03-28 | 1971-04-19 | PYRIDO-[2,3-d]PYRIMIDIN-4(3H)-ONES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702014978 DE2014978A1 (de) | 1970-03-28 | 1970-03-28 | Pyrido eckige Klammer auf 2,3 d eckige Klammer zu pynmidin 4(3H) one und Verfahren zur Herstellung derselben |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2014978A1 true DE2014978A1 (de) | 1971-10-14 |
Family
ID=5766547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702014978 Pending DE2014978A1 (de) | 1970-03-28 | 1970-03-28 | Pyrido eckige Klammer auf 2,3 d eckige Klammer zu pynmidin 4(3H) one und Verfahren zur Herstellung derselben |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3804835A (OSRAM) |
| AT (1) | AT304559B (OSRAM) |
| DE (1) | DE2014978A1 (OSRAM) |
| ES (1) | ES389458A1 (OSRAM) |
| FR (1) | FR2085750B1 (OSRAM) |
| GB (1) | GB1285170A (OSRAM) |
| HU (1) | HU162214B (OSRAM) |
| NL (1) | NL7104092A (OSRAM) |
| SE (1) | SE362248B (OSRAM) |
| ZA (1) | ZA711967B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1446153A (en) * | 1974-03-20 | 1976-08-18 | Lepetit Spa | Pyrrolo-3,4-d-pyrimidines and methods for their preparation |
| PL324486A1 (en) | 1995-07-05 | 1998-05-25 | Du Pont | Fungicidal pyrimidinones |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1040040B (de) * | 1956-07-20 | 1958-10-02 | Basf Ag | Verfahren zur Herstellung von 2, 4-Dioxy-8-azachinazolinen |
-
1970
- 1970-03-28 DE DE19702014978 patent/DE2014978A1/de active Pending
-
1971
- 1971-03-09 US US00122497A patent/US3804835A/en not_active Expired - Lifetime
- 1971-03-23 ES ES389458A patent/ES389458A1/es not_active Expired
- 1971-03-25 FR FR7110521A patent/FR2085750B1/fr not_active Expired
- 1971-03-26 SE SE03963/71A patent/SE362248B/xx unknown
- 1971-03-26 ZA ZA711967A patent/ZA711967B/xx unknown
- 1971-03-26 AT AT261671A patent/AT304559B/de not_active IP Right Cessation
- 1971-03-26 HU HUBO1284A patent/HU162214B/hu unknown
- 1971-03-26 NL NL7104092A patent/NL7104092A/xx unknown
- 1971-04-19 GB GB25366/71A patent/GB1285170A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3804835A (en) | 1974-04-16 |
| FR2085750B1 (OSRAM) | 1975-04-18 |
| AT304559B (de) | 1973-01-10 |
| NL7104092A (OSRAM) | 1971-09-30 |
| ES389458A1 (es) | 1973-06-01 |
| ZA711967B (en) | 1972-01-26 |
| SE362248B (OSRAM) | 1973-12-03 |
| GB1285170A (en) | 1972-08-09 |
| FR2085750A1 (OSRAM) | 1971-12-31 |
| HU162214B (OSRAM) | 1973-01-29 |
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