DD263986A5 - Verfahren zur herstellung von pyrimidinderivaten - Google Patents
Verfahren zur herstellung von pyrimidinderivaten Download PDFInfo
- Publication number
- DD263986A5 DD263986A5 DD87304848A DD30484887A DD263986A5 DD 263986 A5 DD263986 A5 DD 263986A5 DD 87304848 A DD87304848 A DD 87304848A DD 30484887 A DD30484887 A DD 30484887A DD 263986 A5 DD263986 A5 DD 263986A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- pyrimidine
- compounds
- imino
- dihydro
- Prior art date
Links
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims abstract description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052794 bromium Chemical group 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000003230 pyrimidines Chemical class 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 49
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims description 6
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 9
- 229960003632 minoxidil Drugs 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- QJIUMVUZDYPQRT-UHFFFAOYSA-N 6-chloro-2,4-pyrimidinediamine Chemical compound NC1=CC(Cl)=NC(N)=N1 QJIUMVUZDYPQRT-UHFFFAOYSA-N 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000002211 ultraviolet spectrum Methods 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- YDJAPSOKLLXXBT-UHFFFAOYSA-N (6-amino-4-chloro-2-iminopyrimidin-1-yl) acetate Chemical compound CC(=O)ON1C(N)=CC(Cl)=NC1=N YDJAPSOKLLXXBT-UHFFFAOYSA-N 0.000 description 4
- ZIMGGGWCDYVHOY-UHFFFAOYSA-N 3-hydroxy-2-imino-6-(1-piperidinyl)-4-pyrimidinamine Chemical compound N=C1N(O)C(N)=CC(N2CCCCC2)=N1 ZIMGGGWCDYVHOY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- -1 phenylsulfonyloxy group Chemical group 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- JXYVSHBMGAYHAO-UHFFFAOYSA-N CC(=O)NC1=CC(Cl)=NC(=N)N1OC(C)=O Chemical compound CC(=O)NC1=CC(Cl)=NC(=N)N1OC(C)=O JXYVSHBMGAYHAO-UHFFFAOYSA-N 0.000 description 2
- CBGDHGIQSHVIPJ-UHFFFAOYSA-N CC(=O)NC1=NC(Cl)=CC(N)=[N+]1[O-] Chemical compound CC(=O)NC1=NC(Cl)=CC(N)=[N+]1[O-] CBGDHGIQSHVIPJ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 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 1
- 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 1
- XSAXGKVXGVREPY-UHFFFAOYSA-N (6-amino-4-chloro-2-iminopyrimidin-1-yl) propanoate Chemical compound CCC(=O)ON1C(N)=CC(Cl)=NC1=N XSAXGKVXGVREPY-UHFFFAOYSA-N 0.000 description 1
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 1
- DOYINGSIUJRVKA-UHFFFAOYSA-N 6-chloro-3-hydroxy-2-iminopyrimidin-4-amine Chemical compound NC1=CC(Cl)=NC(=N)N1O DOYINGSIUJRVKA-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
- XQDWCUCTRFHSST-UHFFFAOYSA-N [6-amino-2-imino-4-(4-methylphenyl)sulfonyloxypyrimidin-1-yl] acetate Chemical compound N=C1N(OC(=O)C)C(N)=CC(OS(=O)(=O)C=2C=CC(C)=CC=2)=N1 XQDWCUCTRFHSST-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003779 hair growth Effects 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011022 opal Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU862856A HU196061B (en) | 1986-07-10 | 1986-07-10 | Process for production of pirimidine-derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD263986A5 true DD263986A5 (de) | 1989-01-18 |
Family
ID=10961393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD87304848A DD263986A5 (de) | 1986-07-10 | 1987-07-10 | Verfahren zur herstellung von pyrimidinderivaten |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4780537A (cs) |
| EP (1) | EP0254158B1 (cs) |
| JP (1) | JPS6323871A (cs) |
| KR (1) | KR920002825B1 (cs) |
| CN (1) | CN1022410C (cs) |
| AT (1) | ATE72239T1 (cs) |
| CA (1) | CA1305146C (cs) |
| CS (1) | CS274615B2 (cs) |
| DD (1) | DD263986A5 (cs) |
| DE (1) | DE3776443D1 (cs) |
| DK (1) | DK361187A (cs) |
| ES (1) | ES2033263T3 (cs) |
| FI (1) | FI93543C (cs) |
| GR (1) | GR3004261T3 (cs) |
| HU (1) | HU196061B (cs) |
| IL (1) | IL83154A (cs) |
| PL (1) | PL152106B1 (cs) |
| SU (1) | SU1556538A3 (cs) |
| ZA (1) | ZA875051B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5051429A (en) * | 1984-10-12 | 1991-09-24 | Warner-Lambert Co. | "Pyrimidine derivatives" |
| FR2632954B1 (fr) * | 1988-06-15 | 1990-11-16 | Norchim Sarl | Procede de preparation de pyrimidine-n-oxydes |
| JPH02225474A (ja) | 1989-01-04 | 1990-09-07 | Lonza Ag | ２，４―ジアミノ―６―ピペリジニル―ピリミジン―３―ｎ―オキシドの製造方法 |
| FR2781481B1 (fr) | 1998-07-24 | 2000-09-15 | Oreal | Nouveaux 2-amino, 4-alkylamino pyrimidine 3-oxydes et composition les comprenant |
| KR101418342B1 (ko) * | 2013-04-17 | 2014-07-10 | 서울대학교산학협력단 | 현생 조간대 불교란 퇴적층의 퇴적구조 복원 장치 |
| CN114315738B (zh) * | 2022-01-15 | 2023-08-18 | 重庆东寰科技开发有限公司 | 一种2,4-二氨基嘧啶-3-氧化物的制备方法 |
| CN114213340B (zh) | 2022-02-22 | 2022-06-07 | 北京蓝晶微生物科技有限公司 | 2,4-二氨基嘧啶氧化物的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1181657A (en) * | 1966-03-31 | 1970-02-18 | Ici Ltd | Pyrimidine Derivatives and Compositions Containing them |
| CH638216A5 (de) * | 1977-02-04 | 1983-09-15 | Hoffmann La Roche | Oxadiazolopyrimidin-deriate. |
| HU177601B (en) * | 1978-10-27 | 1981-11-28 | Egyt Gyogyszervegyeszeti Gyar | New process for preparing 6-piperidino-2,4-diamino-pyrimidine-3-oxide |
| 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 |
| 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 |
-
1986
- 1986-07-10 HU HU862856A patent/HU196061B/hu not_active IP Right Cessation
-
1987
- 1987-07-09 CN CN87104693A patent/CN1022410C/zh not_active Expired - Fee Related
- 1987-07-10 KR KR1019870007453A patent/KR920002825B1/ko not_active Expired
- 1987-07-10 DK DK361187A patent/DK361187A/da not_active Application Discontinuation
- 1987-07-10 EP EP87109987A patent/EP0254158B1/de not_active Expired - Lifetime
- 1987-07-10 FI FI873051A patent/FI93543C/fi not_active IP Right Cessation
- 1987-07-10 DE DE8787109987T patent/DE3776443D1/de not_active Expired - Lifetime
- 1987-07-10 DD DD87304848A patent/DD263986A5/de not_active IP Right Cessation
- 1987-07-10 US US07/072,010 patent/US4780537A/en not_active Expired - Fee Related
- 1987-07-10 ES ES198787109987T patent/ES2033263T3/es not_active Expired - Lifetime
- 1987-07-10 AT AT87109987T patent/ATE72239T1/de not_active IP Right Cessation
- 1987-07-10 SU SU874202934A patent/SU1556538A3/ru active
- 1987-07-10 ZA ZA875051A patent/ZA875051B/xx unknown
- 1987-07-10 PL PL1987266757A patent/PL152106B1/pl unknown
- 1987-07-10 CA CA000541770A patent/CA1305146C/en not_active Expired - Lifetime
- 1987-07-10 JP JP62171320A patent/JPS6323871A/ja active Pending
- 1987-07-10 CS CS527487A patent/CS274615B2/cs unknown
- 1987-07-10 IL IL83154A patent/IL83154A/xx not_active IP Right Cessation
-
1992
- 1992-04-02 GR GR920400616T patent/GR3004261T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN87104693A (zh) | 1988-01-20 |
| KR880001610A (ko) | 1988-04-25 |
| JPS6323871A (ja) | 1988-02-01 |
| EP0254158A2 (de) | 1988-01-27 |
| CS274615B2 (en) | 1991-09-15 |
| KR920002825B1 (ko) | 1992-04-04 |
| DE3776443D1 (de) | 1992-03-12 |
| CN1022410C (zh) | 1993-10-13 |
| DK361187D0 (da) | 1987-07-10 |
| FI873051A0 (fi) | 1987-07-10 |
| US4780537A (en) | 1988-10-25 |
| PL266757A1 (en) | 1988-07-07 |
| ATE72239T1 (de) | 1992-02-15 |
| EP0254158A3 (en) | 1988-03-30 |
| CS527487A2 (en) | 1991-01-15 |
| IL83154A (en) | 1991-07-18 |
| CA1305146C (en) | 1992-07-14 |
| FI93543C (fi) | 1995-04-25 |
| DK361187A (da) | 1988-01-11 |
| HUT44520A (en) | 1988-03-28 |
| EP0254158B1 (de) | 1992-01-29 |
| SU1556538A3 (ru) | 1990-04-07 |
| GR3004261T3 (cs) | 1993-03-31 |
| FI873051A7 (fi) | 1988-01-11 |
| IL83154A0 (en) | 1987-12-31 |
| HU196061B (en) | 1988-09-28 |
| ES2033263T3 (es) | 1993-03-16 |
| PL152106B1 (en) | 1990-11-30 |
| FI93543B (fi) | 1995-01-13 |
| ZA875051B (en) | 1988-01-15 |
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