DE1695975A1 - Derivate des Pyrimidins - Google Patents
Derivate des PyrimidinsInfo
- Publication number
- DE1695975A1 DE1695975A1 DE19681695975 DE1695975A DE1695975A1 DE 1695975 A1 DE1695975 A1 DE 1695975A1 DE 19681695975 DE19681695975 DE 19681695975 DE 1695975 A DE1695975 A DE 1695975A DE 1695975 A1 DE1695975 A1 DE 1695975A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrimidine
- hydroxyethyl
- methyl
- propyl
- chloro
- 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
- 150000003230 pyrimidines Chemical class 0.000 title claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 41
- -1 pyrimidine - 2-ethyl-4-methyl-6-morpholino-pyrimidine - 2-propyl-4-methyl-6- (2-hydroxyethyl) aminopyrimidine Chemical compound 0.000 claims description 24
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- MMUVMJBBYCJHQT-UHFFFAOYSA-N 4-(6-methyl-2-propan-2-ylpyrimidin-4-yl)morpholine Chemical compound CC(C)C1=NC(C)=CC(N2CCOCC2)=N1 MMUVMJBBYCJHQT-UHFFFAOYSA-N 0.000 claims 1
- NGCMQAQWALQLTR-UHFFFAOYSA-N 4-(6-methylpyrimidin-4-yl)morpholine Chemical compound C1=NC(C)=CC(N2CCOCC2)=N1 NGCMQAQWALQLTR-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001477 organic nitrogen group Chemical group 0.000 claims 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 53
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 229960000278 theophylline Drugs 0.000 description 16
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- HTXWKZDRDRFVHN-UHFFFAOYSA-N 2-methyloxiran-2-ol Chemical compound CC1(O)CO1 HTXWKZDRDRFVHN-UHFFFAOYSA-N 0.000 description 6
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 230000002048 spasmolytic effect Effects 0.000 description 4
- 241000700198 Cavia Species 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- LOZKMMHGSINGLY-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)ethanol Chemical compound NC1=NC=CC(CCO)=N1 LOZKMMHGSINGLY-UHFFFAOYSA-N 0.000 description 2
- GEFFLIRHJHAXFX-UHFFFAOYSA-N 4-(6-chloro-2-propylpyrimidin-4-yl)morpholine Chemical compound CCCC1=NC(Cl)=CC(N2CCOCC2)=N1 GEFFLIRHJHAXFX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 239000002269 analeptic agent Substances 0.000 description 2
- 230000003555 analeptic effect Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 230000000916 dilatatory effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000010412 perfusion Effects 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 210000003437 trachea Anatomy 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 1
- FMEJLURMWWHSFX-UHFFFAOYSA-N 2-(5-amino-6-methyl-2-propylpyrimidin-4-yl)ethanol Chemical compound C(CC)C1=NC(=C(C(=N1)C)N)CCO FMEJLURMWWHSFX-UHFFFAOYSA-N 0.000 description 1
- MGYAGUUKOYNYAT-UHFFFAOYSA-N 2-(oxan-2-yl)oxane Chemical compound O1CCCCC1C1OCCCC1 MGYAGUUKOYNYAT-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- AYIVVSYNNZZADH-UHFFFAOYSA-N 4,6-dichloro-2-propylpyrimidine Chemical compound CCCC1=NC(Cl)=CC(Cl)=N1 AYIVVSYNNZZADH-UHFFFAOYSA-N 0.000 description 1
- UJYDECVJWFOLNT-UHFFFAOYSA-N 4-(2-methylpyrimidin-4-yl)morpholine Chemical compound CC1=NC=CC(N2CCOCC2)=N1 UJYDECVJWFOLNT-UHFFFAOYSA-N 0.000 description 1
- KYMZHELNOCGCTH-UHFFFAOYSA-N 4-(2-propylpyrimidin-4-yl)morpholine Chemical compound CCCC1=NC=CC(N2CCOCC2)=N1 KYMZHELNOCGCTH-UHFFFAOYSA-N 0.000 description 1
- UPGDYMACJFZROW-UHFFFAOYSA-N 4-(6-chloro-2-methylpyrimidin-4-yl)morpholine Chemical compound CC1=NC(Cl)=CC(N2CCOCC2)=N1 UPGDYMACJFZROW-UHFFFAOYSA-N 0.000 description 1
- CFOBQJWOZVMWBR-UHFFFAOYSA-N 4-(6-chloropyrimidin-4-yl)morpholine Chemical compound C1=NC(Cl)=CC(N2CCOCC2)=N1 CFOBQJWOZVMWBR-UHFFFAOYSA-N 0.000 description 1
- AIPSHVWZBOQGON-UHFFFAOYSA-N 4-chloro-6-methyl-2-propylpyrimidine Chemical compound CCCC1=NC(C)=CC(Cl)=N1 AIPSHVWZBOQGON-UHFFFAOYSA-N 0.000 description 1
- DBPKMSBWOKAKLA-UHFFFAOYSA-N 4-chloropyrimidine Chemical compound ClC1=CC=NC=N1 DBPKMSBWOKAKLA-UHFFFAOYSA-N 0.000 description 1
- DUIMWXDLDBNUFD-UHFFFAOYSA-N 4-pyrimidin-2-ylmorpholine Chemical compound C1COCCN1C1=NC=CC=N1 DUIMWXDLDBNUFD-UHFFFAOYSA-N 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 230000003836 peripheral circulation Effects 0.000 description 1
- 230000036581 peripheral resistance Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003033 spasmogenic effect Effects 0.000 description 1
- 230000001148 spastic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
-
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3774/67A GB1143167A (en) | 1967-01-25 | 1967-01-25 | Derivatives of pyrimidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1695975A1 true DE1695975A1 (de) | 1971-05-19 |
Family
ID=9764663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681695975 Pending DE1695975A1 (de) | 1967-01-25 | 1968-01-23 | Derivate des Pyrimidins |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3624084A (enrdf_load_stackoverflow) |
| BE (1) | BE709787A (enrdf_load_stackoverflow) |
| DE (1) | DE1695975A1 (enrdf_load_stackoverflow) |
| FR (2) | FR1555900A (enrdf_load_stackoverflow) |
| GB (1) | GB1143167A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384370A1 (de) * | 1989-02-22 | 1990-08-29 | Hoechst Aktiengesellschaft | Substituierte Pyrimidin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Tool |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1523274A (en) * | 1974-08-05 | 1978-08-31 | Ici Ltd | Herbicidal compositions containing substituted pyrimidine |
| FR2306697A1 (fr) * | 1975-04-10 | 1976-11-05 | Sogeras | Nouvelles pyrimidines utilisables comme medicaments antidiabetiques et hypocholesterolemiants |
| PH20344A (en) * | 1981-01-29 | 1986-12-04 | Sankyo Co | Aminopyrimidine derivatives, processes for their preparation, and fungicidal, insecticidal and acaricidal compositions containing them |
| US5254555A (en) * | 1989-10-30 | 1993-10-19 | Beecham Group P.L.C. | Amino pyrimidin-7-yl substituted benzopyrans for treatment of hypertension |
| FR2662607B1 (fr) * | 1990-05-30 | 1992-08-28 | Oreal | Composition destinee a etre utilisee pour freiner la chute des cheveux et pour induire et stimuler leur croissance, contenant des derives d'alkyl-2 amino-4 (ou dialkyl-2-4) pyrimidine oxyde-3 . |
| JPH09301958A (ja) * | 1996-05-09 | 1997-11-25 | Nippon Shoji Kk | 新規ピリミジン化合物及び抗ロタウイルス剤 |
| DE60314730T2 (de) * | 2002-03-15 | 2008-06-05 | Ciba Specialty Chemicals Holding Inc. | Verwendung von 4-aminopyrimidinen zur antimikrobiellen behandlung von oberflächen |
| WO2003087064A1 (en) * | 2002-04-18 | 2003-10-23 | Ucb, S.A. | Chemical compounds with dual activity, processes for their preparation and pharmaceutical compositions |
| EP1646615B1 (en) * | 2003-06-06 | 2009-08-26 | Vertex Pharmaceuticals Incorporated | Pyrimidine derivatives as modulators of atp-binding cassette transporters |
| HN2005000795A (es) * | 2004-10-15 | 2010-08-19 | Aventis Pharma Inc | Pirimidinas como antagonistas del receptor de prostaglandina d2 |
| WO2009105220A1 (en) * | 2008-02-19 | 2009-08-27 | Janssen Pharmaceutica N.V. | Aryl-hydroxyethylamino-pyrimidines and triazines as modulators of fatty acid amide hydrolase |
| WO2011105572A1 (ja) * | 2010-02-26 | 2011-09-01 | 持田製薬株式会社 | 新規ヘテロアリール誘導体 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2994637A (en) * | 1957-11-13 | 1961-08-01 | Diamond Alkali Co | Aminopyrimidines as fungicides |
| GB1031265A (en) * | 1963-11-12 | 1966-06-02 | Geigy Co Ltd | Tri-tertiary aminopyrimidines and their production |
| NL127996C (enrdf_load_stackoverflow) * | 1963-11-19 |
-
1967
- 1967-01-25 GB GB3774/67A patent/GB1143167A/en not_active Expired
-
1968
- 1968-01-08 FR FR1555900D patent/FR1555900A/fr not_active Expired
- 1968-01-22 US US699294A patent/US3624084A/en not_active Expired - Lifetime
- 1968-01-23 DE DE19681695975 patent/DE1695975A1/de active Pending
- 1968-01-24 BE BE709787D patent/BE709787A/xx unknown
- 1968-03-25 FR FR145321A patent/FR7383M/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384370A1 (de) * | 1989-02-22 | 1990-08-29 | Hoechst Aktiengesellschaft | Substituierte Pyrimidin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Tool |
| US5138058A (en) * | 1989-02-22 | 1992-08-11 | Hoechst Aktiengesellschaft | Piperazine substituted pyrimidine derivatives and physiologically tolerated salts thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR7383M (enrdf_load_stackoverflow) | 1969-10-27 |
| GB1143167A (en) | 1969-02-19 |
| US3624084A (en) | 1971-11-30 |
| BE709787A (enrdf_load_stackoverflow) | 1968-07-24 |
| FR1555900A (enrdf_load_stackoverflow) | 1969-01-31 |
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