CH411915A - Verfahren zur Herstellung von neuen Derivaten des Pyrimido-(4,5-d)-pyrimidins - Google Patents
Verfahren zur Herstellung von neuen Derivaten des Pyrimido-(4,5-d)-pyrimidinsInfo
- Publication number
- CH411915A CH411915A CH108561A CH108561A CH411915A CH 411915 A CH411915 A CH 411915A CH 108561 A CH108561 A CH 108561A CH 108561 A CH108561 A CH 108561A CH 411915 A CH411915 A CH 411915A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrimido
- pyrimidine
- formula
- reaction
- found
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- QGDYVSSVBYMOJN-UHFFFAOYSA-N pyrimido[4,5-d]pyrimidine Chemical class C1=NC=NC2=NC=NC=C21 QGDYVSSVBYMOJN-UHFFFAOYSA-N 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- -1 alkyl mercaptan Chemical compound 0.000 description 6
- SURZBXMKNNZTLE-UHFFFAOYSA-N pyrimido[4,5-d]pyrimidine-2,4,7-triamine Chemical class NC1=NC(N)=NC2=NC(N)=NC=C21 SURZBXMKNNZTLE-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- ZYFHFUZRKIXHKK-UHFFFAOYSA-N 4-chloro-2,7-di(piperidin-1-yl)pyrimido[4,5-d]pyrimidine Chemical compound N1(CCCCC1)C=1N=C(C=2C(=NC(=NC2)N2CCCCC2)N1)Cl ZYFHFUZRKIXHKK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- PNJNLWPILYXYEZ-UHFFFAOYSA-N 4-chloro-2,7-dipyrrolidin-1-ylpyrimido[4,5-d]pyrimidine Chemical compound N1(CCCC1)C=1N=C(C=2C(=NC(=NC2)N2CCCC2)N1)Cl PNJNLWPILYXYEZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FTEJQRQLCOVNQB-UHFFFAOYSA-N N-butyl-2,7-di(piperidin-1-yl)pyrimido[4,5-d]pyrimidin-4-amine Chemical compound N1(CCCCC1)C=1N=C(C=2C(=NC(=NC=2)N2CCCCC2)N=1)NCCCC FTEJQRQLCOVNQB-UHFFFAOYSA-N 0.000 description 2
- ZOFVQUAJTXEBNW-UHFFFAOYSA-N N1(CCCCC1)C=1N=C(C=2C(=NC(=NC2)N2CCCCC2)N1)N(CC)CC Chemical compound N1(CCCCC1)C=1N=C(C=2C(=NC(=NC2)N2CCCCC2)N1)N(CC)CC ZOFVQUAJTXEBNW-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VCCZUVVCZYNRHN-UHFFFAOYSA-N (2,7-dimorpholin-4-ylpyrimido[4,5-d]pyrimidin-4-yl)hydrazine Chemical compound N=1C=C2C(NN)=NC(N3CCOCC3)=NC2=NC=1N1CCOCC1 VCCZUVVCZYNRHN-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- CENPSKZOTLCZSA-UHFFFAOYSA-N 2,4,7-tri(piperidin-1-yl)pyrimido[4,5-d]pyrimidine Chemical compound N1(CCCCC1)C=1N=C(C=2C(=NC(=NC=2)N2CCCCC2)N=1)N1CCCCC1 CENPSKZOTLCZSA-UHFFFAOYSA-N 0.000 description 1
- ZFJNUPFEMXDHLX-UHFFFAOYSA-N 2,4,7-tripyrrolidin-1-ylpyrimido[4,5-d]pyrimidine Chemical compound N1(CCCC1)C=1N=C(C=2C(=NC(=NC=2)N2CCCC2)N=1)N1CCCC1 ZFJNUPFEMXDHLX-UHFFFAOYSA-N 0.000 description 1
- HVAZEVSMJZPCPV-UHFFFAOYSA-N 2,7-di(piperidin-1-yl)-4-pyrrolidin-1-ylpyrimido[4,5-d]pyrimidine Chemical compound C1CCCN1C1=NC(N2CCCCC2)=NC2=NC(N3CCCCC3)=NC=C12 HVAZEVSMJZPCPV-UHFFFAOYSA-N 0.000 description 1
- WIRPTMAKVRGPBR-UHFFFAOYSA-N 2,7-di(piperidin-1-yl)-N-propylpyrimido[4,5-d]pyrimidin-4-amine Chemical compound N1(CCCCC1)C=1N=C(C=2C(=NC(=NC=2)N2CCCCC2)N=1)NCCC WIRPTMAKVRGPBR-UHFFFAOYSA-N 0.000 description 1
- DBESLOAOEGYXOY-UHFFFAOYSA-N 2,7-dimorpholin-4-yl-N-phenylpyrimido[4,5-d]pyrimidin-4-amine Chemical compound O1CCN(CC1)C=1N=C(C=2C(=NC(=NC=2)N2CCOCC2)N=1)NC1=CC=CC=C1 DBESLOAOEGYXOY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
- NQQLLSYBUWGVIA-UHFFFAOYSA-N 4-(2,4-dimorpholin-4-ylpyrimido[4,5-d]pyrimidin-7-yl)morpholine Chemical compound C1COCCN1C1=NC=C(C(=NC(=N2)N3CCOCC3)N3CCOCC3)C2=N1 NQQLLSYBUWGVIA-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
- GHJILKPGGJCXGL-UHFFFAOYSA-N 4-(4-chloro-2-morpholin-4-ylpyrimido[4,5-d]pyrimidin-7-yl)morpholine Chemical compound O1CCN(CC1)C=1N=C(C=2C(=NC(=NC2)N2CCOCC2)N1)Cl GHJILKPGGJCXGL-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- FRQVTRZWEMKTCP-UHFFFAOYSA-N N-butyl-2,7-dipyrrolidin-1-ylpyrimido[4,5-d]pyrimidin-4-amine Chemical compound N1(CCCC1)C=1N=C(C=2C(=NC(=NC=2)N2CCCC2)N=1)NCCCC FRQVTRZWEMKTCP-UHFFFAOYSA-N 0.000 description 1
- DFAHXRHCOBUGMS-UHFFFAOYSA-N N-propyl-2,7-dipyrrolidin-1-ylpyrimido[4,5-d]pyrimidin-4-amine Chemical compound N1(CCCC1)C=1N=C(C=2C(=NC(=NC=2)N2CCCC2)N=1)NCCC DFAHXRHCOBUGMS-UHFFFAOYSA-N 0.000 description 1
- DBGFCHQQNNLXBS-UHFFFAOYSA-N N1(CCCC1)C=1N=C(C=2C(=NC(=NC2)N2CCCC2)N1)N1CCOCC1 Chemical compound N1(CCCC1)C=1N=C(C=2C(=NC(=NC2)N2CCCC2)N1)N1CCOCC1 DBGFCHQQNNLXBS-UHFFFAOYSA-N 0.000 description 1
- YKEDEQTXEWWFFK-UHFFFAOYSA-N N1(CCCCC1)C=1N=C(C=2C(=NC(=NC=2)N2CCCCC2)N=1)NN Chemical compound N1(CCCCC1)C=1N=C(C=2C(=NC(=NC=2)N2CCCCC2)N=1)NN YKEDEQTXEWWFFK-UHFFFAOYSA-N 0.000 description 1
- CIMWYBTWOOKTBT-UHFFFAOYSA-N N1(CCCCC1)C=1N=C(C=2C(=NC(=NC=2)N2CCOCC2)N=1)N1CCCC1 Chemical compound N1(CCCCC1)C=1N=C(C=2C(=NC(=NC=2)N2CCOCC2)N=1)N1CCCC1 CIMWYBTWOOKTBT-UHFFFAOYSA-N 0.000 description 1
- LYGQCBWGOIFMJE-UHFFFAOYSA-N O1CCN(CC1)C=1N=C(C=2C(=NC(=NC2)N2CCOCC2)N1)NC(C)C Chemical compound O1CCN(CC1)C=1N=C(C=2C(=NC(=NC2)N2CCOCC2)N1)NC(C)C LYGQCBWGOIFMJE-UHFFFAOYSA-N 0.000 description 1
- ZRWVLMITGYZHCQ-UHFFFAOYSA-N O1CCN(CC1)C=1N=C(C=2C(=NC(=NC2)N2CCOCC2)N1)NCCC Chemical compound O1CCN(CC1)C=1N=C(C=2C(=NC(=NC2)N2CCOCC2)N1)NCCC ZRWVLMITGYZHCQ-UHFFFAOYSA-N 0.000 description 1
- HCNTXPCJBOUINE-UHFFFAOYSA-N O1CCN(CC1)C=1N=C(C=2C(=NC(=NC2)N2CCOCC2)N1)NCCC(C)C Chemical compound O1CCN(CC1)C=1N=C(C=2C(=NC(=NC2)N2CCOCC2)N1)NCCC(C)C HCNTXPCJBOUINE-UHFFFAOYSA-N 0.000 description 1
- ZSZREJIJRBCDOB-UHFFFAOYSA-N O1CCN(CC1)C=1N=C(C=2C(=NC(=NC=2)N2CCOCC2)N=1)N1CCCC1 Chemical compound O1CCN(CC1)C=1N=C(C=2C(=NC(=NC=2)N2CCOCC2)N=1)N1CCCC1 ZSZREJIJRBCDOB-UHFFFAOYSA-N 0.000 description 1
- YZNWIAMSJBGSDE-UHFFFAOYSA-N O1CCN(CC1)C=1N=C(C=2C(=NC(=NC=2)N2CCOCC2)N=1)N1CCCCC1 Chemical compound O1CCN(CC1)C=1N=C(C=2C(=NC(=NC=2)N2CCOCC2)N=1)N1CCCCC1 YZNWIAMSJBGSDE-UHFFFAOYSA-N 0.000 description 1
- OUNDLSDORFEREJ-UHFFFAOYSA-N O1CCN(CC1)C=1N=C(C=2C(=NC(=NC=2)N2CCOCC2)N=1)NC1CCCCC1 Chemical compound O1CCN(CC1)C=1N=C(C=2C(=NC(=NC=2)N2CCOCC2)N=1)NC1CCCCC1 OUNDLSDORFEREJ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PWXJJVFBNNRJOM-UHFFFAOYSA-N n,n-diethyl-2,7-dimorpholin-4-ylpyrimido[4,5-d]pyrimidin-4-amine Chemical compound N=1C=C2C(N(CC)CC)=NC(N3CCOCC3)=NC2=NC=1N1CCOCC1 PWXJJVFBNNRJOM-UHFFFAOYSA-N 0.000 description 1
- OTTYTMZUZXGRLY-UHFFFAOYSA-N n-benzyl-2,7-dimorpholin-4-ylpyrimido[4,5-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1CNC(C1=CN=2)=NC(N3CCOCC3)=NC1=NC=2N1CCOCC1 OTTYTMZUZXGRLY-UHFFFAOYSA-N 0.000 description 1
- NVASQZSWANCJKY-UHFFFAOYSA-N n-cyclohexyl-2,7-di(piperidin-1-yl)pyrimido[4,5-d]pyrimidin-4-amine Chemical compound C1CCCCC1NC1=NC(N2CCCCC2)=NC2=NC(N3CCCCC3)=NC=C12 NVASQZSWANCJKY-UHFFFAOYSA-N 0.000 description 1
- FKGLDUZDGGJGNS-UHFFFAOYSA-N n-tert-butyl-4-morpholin-4-yl-6-(6-propoxypyridazin-3-yl)oxy-1,3,5-triazin-2-amine Chemical compound N1=NC(OCCC)=CC=C1OC1=NC(NC(C)(C)C)=NC(N2CCOCC2)=N1 FKGLDUZDGGJGNS-UHFFFAOYSA-N 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET0017892 | 1960-02-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH411915A true CH411915A (de) | 1966-04-30 |
Family
ID=7548755
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH108561A CH411915A (de) | 1960-02-15 | 1961-01-30 | Verfahren zur Herstellung von neuen Derivaten des Pyrimido-(4,5-d)-pyrimidins |
| CH490565A CH421126A (de) | 1960-02-15 | 1961-01-30 | Verfahren zur Herstellung von neuen Derivaten des Pyrimido-(4,5-d)-pyrimidins |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH490565A CH421126A (de) | 1960-02-15 | 1961-01-30 | Verfahren zur Herstellung von neuen Derivaten des Pyrimido-(4,5-d)-pyrimidins |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE600194A (OSRAM) |
| CH (2) | CH411915A (OSRAM) |
| DE (1) | DE1445156A1 (OSRAM) |
| DK (1) | DK103779C (OSRAM) |
| FR (1) | FR1472006A (OSRAM) |
| GB (1) | GB926696A (OSRAM) |
| NL (1) | NL6406735A (OSRAM) |
| SE (3) | SE301145B (OSRAM) |
-
1960
- 1960-02-15 DE DE19601445156 patent/DE1445156A1/de active Pending
-
1961
- 1961-01-30 CH CH108561A patent/CH411915A/de unknown
- 1961-01-30 CH CH490565A patent/CH421126A/de unknown
- 1961-02-10 SE SE138761A patent/SE301145B/xx unknown
- 1961-02-14 DK DK60761A patent/DK103779C/da active
- 1961-02-14 FR FR852697A patent/FR1472006A/fr not_active Expired
- 1961-02-14 GB GB549161A patent/GB926696A/en not_active Expired
- 1961-02-14 BE BE600194A patent/BE600194A/fr unknown
-
1962
- 1962-10-03 SE SE1168862A patent/SE301481B/xx unknown
- 1962-10-31 SE SE1168962A patent/SE301147B/xx unknown
-
1964
- 1964-06-12 NL NL6406735A patent/NL6406735A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1472006A (fr) | 1967-03-10 |
| NL6406735A (OSRAM) | 1964-08-10 |
| DE1445156A1 (de) | 1972-04-06 |
| DK103779C (da) | 1966-02-21 |
| BE600194A (fr) | 1961-08-14 |
| CH421126A (de) | 1966-09-30 |
| SE301481B (sv) | 1968-06-10 |
| SE301145B (sv) | 1968-05-27 |
| GB926696A (en) | 1963-05-22 |
| SE301147B (sv) | 1968-05-27 |
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