HU177601B - New process for preparing 6-piperidino-2,4-diamino-pyrimidine-3-oxide - Google Patents
New process for preparing 6-piperidino-2,4-diamino-pyrimidine-3-oxide Download PDFInfo
- Publication number
- HU177601B HU177601B HU78EE2594A HUEE002594A HU177601B HU 177601 B HU177601 B HU 177601B HU 78EE2594 A HU78EE2594 A HU 78EE2594A HU EE002594 A HUEE002594 A HU EE002594A HU 177601 B HU177601 B HU 177601B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- diaminopyrimidine
- defined above
- priority
- piperidine
- Prior art date
Links
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 27
- SWELIMKTDYHAOY-UHFFFAOYSA-N 2,4-diamino-6-hydroxypyrimidine Chemical compound NC1=CC(=O)N=C(N)N1 SWELIMKTDYHAOY-UHFFFAOYSA-N 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- -1 carbonyl halide Chemical class 0.000 claims abstract description 11
- 150000003461 sulfonyl halides Chemical class 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 12
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 10
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical group CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 5
- SXIUYERFFIKRTI-UHFFFAOYSA-N C1=CC(C)=CC=C1S(=O)(=O)OC1=CC(N)=[N+]([O-])C(N)=N1 Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC(N)=[N+]([O-])C(N)=N1 SXIUYERFFIKRTI-UHFFFAOYSA-N 0.000 claims description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 5
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 5
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims description 4
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 3
- WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 claims description 3
- PJGMEHBFGKUQJH-UHFFFAOYSA-N N=C1N=C(C=C(N1OC(C1=CC(=CC=C1)Cl)=O)N)OS(=O)(=O)C1=CC=C(C=C1)C Chemical compound N=C1N=C(C=C(N1OC(C1=CC(=CC=C1)Cl)=O)N)OS(=O)(=O)C1=CC=C(C=C1)C PJGMEHBFGKUQJH-UHFFFAOYSA-N 0.000 claims description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical group ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003586 protic polar solvent Substances 0.000 claims description 3
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical group CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 238000011065 in-situ storage Methods 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001916 cyano esters Chemical class 0.000 claims 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 claims 1
- 238000005694 sulfonylation reaction Methods 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract 2
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000243 solution Substances 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- IDCARVYLHZLEMC-UHFFFAOYSA-N (2,6-diaminopyrimidin-4-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC(N)=NC(N)=N1 IDCARVYLHZLEMC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- PVJZBZSCGJAWNG-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonyl chloride Chemical compound CC1=CC(C)=C(S(Cl)(=O)=O)C(C)=C1 PVJZBZSCGJAWNG-UHFFFAOYSA-N 0.000 description 3
- QJIUMVUZDYPQRT-UHFFFAOYSA-N 6-chloro-2,4-pyrimidinediamine Chemical compound NC1=CC(Cl)=NC(N)=N1 QJIUMVUZDYPQRT-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- XVXAEWGDVYFRBE-UHFFFAOYSA-N (2,6-diaminopyrimidin-4-yl) 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)OC1=CC(N)=NC(N)=N1 XVXAEWGDVYFRBE-UHFFFAOYSA-N 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- ANLQHFYDQPMDJY-UHFFFAOYSA-N 3-oxo-3-piperidin-1-ylpropanenitrile Chemical compound N#CCC(=O)N1CCCCC1 ANLQHFYDQPMDJY-UHFFFAOYSA-N 0.000 description 2
- FZTPPEKGQYQXQJ-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)OC1=CC(=NC(=N1)N)N Chemical compound C1(=CC=CC=C1)S(=O)(=O)OC1=CC(=NC(=N1)N)N FZTPPEKGQYQXQJ-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- OOKAXVQQXHCPCB-UHFFFAOYSA-N (2,6-diaminopyrimidin-4-yl) methanesulfonate Chemical compound CS(=O)(=O)OC1=CC(=NC(=N1)N)N OOKAXVQQXHCPCB-UHFFFAOYSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- XJUVNJMVRYPJEF-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidin-6-ol Chemical compound OC1=CCNCN1 XJUVNJMVRYPJEF-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- DEFYUEFWOBCOCX-UHFFFAOYSA-N 6-phenoxypyrimidine-2,4-diamine Chemical compound NC1=NC(N)=CC(OC=2C=CC=CC=2)=N1 DEFYUEFWOBCOCX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- IGRWHBBHXVNZEO-UHFFFAOYSA-N guanidine;hypochlorous acid Chemical compound ClO.NC(N)=N IGRWHBBHXVNZEO-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU78EE2594A HU177601B (en) | 1978-10-27 | 1978-10-27 | New process for preparing 6-piperidino-2,4-diamino-pyrimidine-3-oxide |
| SE7908629A SE432596B (sv) | 1978-10-27 | 1979-10-17 | Forfarande for framstellning av 6-piperidino-2,4-diaminopyrimidin-3-oxid |
| GB7936681A GB2032434B (en) | 1978-10-27 | 1979-10-23 | Process for the preparation of 6 - piperidino - 2,4 - diamino - pyrimidine - 3-oxide |
| AT0689879A AT373246B (de) | 1978-10-27 | 1979-10-23 | Neues verfahren zur herstellung von 6-piperidino- 2,4-diaminopyrimidin-3-oxid |
| FI793307A FI793307A7 (fi) | 1978-10-27 | 1979-10-24 | Menetelmä 6-piperidino-2,4- diaminopyrimidiini-3-oksidin valmistamiseksi. |
| DE19792943161 DE2943161A1 (de) | 1978-10-27 | 1979-10-25 | Verfahren zur herstellung von 6-piperidino-2,4-diaminopyrimidin-3- oxyd |
| CH958279A CH642365A5 (de) | 1978-10-27 | 1979-10-25 | Verfahren zur herstellung von 6-piperidino-2,4-diaminopyrimidin-3-oxid. |
| CS797272A CS213398B2 (en) | 1978-10-27 | 1979-10-25 | Method of making the 6-piperidino-2,4-diaminopyrimidin-3-oxide |
| SU792830754A SU913942A3 (en) | 1978-10-27 | 1979-10-25 | Process for producing 2,4-diamino-6-pyperidinopyrimidine-3-oxy (its modifications) |
| DK454579A DK454579A (da) | 1978-10-27 | 1979-10-26 | Fremgangsmaade til fremstilling af 6-piperidino-2,4-diaminopyrimidin-3-oxid |
| YU02625/79A YU262579A (en) | 1978-10-27 | 1979-10-26 | New process for obtaining 6-piperidino-2,4-diamino-pyrimidine-3-oxide |
| ES485457A ES485457A1 (es) | 1978-10-27 | 1979-10-26 | Procedimiento de preparacion de 6-piperidino-2,4-diaminopi- rimidina-3-oxido |
| PL1979219242A PL119712B1 (en) | 1978-10-27 | 1979-10-26 | Process for preparing 6-piperidin-2,4-diaminopyrimidine 3-oxideina |
| JP13829279A JPS5559172A (en) | 1978-10-27 | 1979-10-27 | Manufacture of 66piperidinoo2*44diaminopyrimidinee33oxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU78EE2594A HU177601B (en) | 1978-10-27 | 1978-10-27 | New process for preparing 6-piperidino-2,4-diamino-pyrimidine-3-oxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU177601B true HU177601B (en) | 1981-11-28 |
Family
ID=10995794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU78EE2594A HU177601B (en) | 1978-10-27 | 1978-10-27 | New process for preparing 6-piperidino-2,4-diamino-pyrimidine-3-oxide |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5559172A (cs) |
| AT (1) | AT373246B (cs) |
| CH (1) | CH642365A5 (cs) |
| CS (1) | CS213398B2 (cs) |
| DE (1) | DE2943161A1 (cs) |
| DK (1) | DK454579A (cs) |
| ES (1) | ES485457A1 (cs) |
| FI (1) | FI793307A7 (cs) |
| GB (1) | GB2032434B (cs) |
| HU (1) | HU177601B (cs) |
| PL (1) | PL119712B1 (cs) |
| SE (1) | SE432596B (cs) |
| SU (1) | SU913942A3 (cs) |
| YU (1) | YU262579A (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1179344A (en) * | 1981-07-15 | 1984-12-11 | Jean-Claude Muller | Process for the preparation of 6-¬3,6-dihydro-1(2h)- pyridyl| pyrimidine-3-oxides |
| CH649291A5 (de) * | 1982-03-16 | 1985-05-15 | Hoffmann La Roche | Dicarbamate. |
| HU196061B (en) * | 1986-07-10 | 1988-09-28 | Richter Gedeon Vegyeszet | Process for production of pirimidine-derivatives |
| HU196067B (en) * | 1986-07-10 | 1988-09-28 | Richter Gedeon Vegyeszet | Process for production of 6-amin-1,2-dihydro-1-hydroxi-2-imino-4-piperidin-piramidin |
| FI864046A7 (fi) * | 1986-10-07 | 1988-04-08 | Farmos Oy | Menetelmä terapeuttisesti aktiivisen yhdisteen valmistamiseksi. |
| LU86958A1 (fr) * | 1987-07-31 | 1989-03-08 | Oreal | Sels d'acide thiamorpholinone carboxylique et de derives de diamino-2,4 pyrimidine,leur utilisation en cosmetique et pharmacie |
| LU86960A1 (fr) * | 1987-07-31 | 1989-03-08 | Oreal | Procede de preparation de piperidino-6 diamino-2,4 pyrimidine oxyde-3 et composes nouveaux |
| US4959475A (en) * | 1989-01-04 | 1990-09-25 | Lonza Ltd. | Process for the production of 2,4-diamino-6-piperidinyl-pyrimidine-3-N-oxide |
-
1978
- 1978-10-27 HU HU78EE2594A patent/HU177601B/hu not_active IP Right Cessation
-
1979
- 1979-10-17 SE SE7908629A patent/SE432596B/sv unknown
- 1979-10-23 AT AT0689879A patent/AT373246B/de not_active IP Right Cessation
- 1979-10-23 GB GB7936681A patent/GB2032434B/en not_active Expired
- 1979-10-24 FI FI793307A patent/FI793307A7/fi not_active Application Discontinuation
- 1979-10-25 SU SU792830754A patent/SU913942A3/ru active
- 1979-10-25 CS CS797272A patent/CS213398B2/cs unknown
- 1979-10-25 CH CH958279A patent/CH642365A5/de not_active IP Right Cessation
- 1979-10-25 DE DE19792943161 patent/DE2943161A1/de not_active Withdrawn
- 1979-10-26 YU YU02625/79A patent/YU262579A/xx unknown
- 1979-10-26 PL PL1979219242A patent/PL119712B1/pl unknown
- 1979-10-26 ES ES485457A patent/ES485457A1/es not_active Expired
- 1979-10-26 DK DK454579A patent/DK454579A/da not_active Application Discontinuation
- 1979-10-27 JP JP13829279A patent/JPS5559172A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PL219242A1 (cs) | 1980-06-16 |
| CH642365A5 (de) | 1984-04-13 |
| ES485457A1 (es) | 1980-10-01 |
| PL119712B1 (en) | 1982-01-30 |
| FI793307A7 (fi) | 1981-01-01 |
| JPS5559172A (en) | 1980-05-02 |
| SE432596B (sv) | 1984-04-09 |
| YU262579A (en) | 1983-01-21 |
| CS213398B2 (en) | 1982-04-09 |
| SU913942A3 (en) | 1982-03-15 |
| GB2032434B (en) | 1982-11-17 |
| DE2943161A1 (de) | 1980-05-08 |
| AT373246B (de) | 1983-12-27 |
| DK454579A (da) | 1980-04-28 |
| SE7908629L (sv) | 1980-04-28 |
| GB2032434A (en) | 1980-05-08 |
| ATA689879A (de) | 1983-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |