DE3008693A1 - 6-aryl-pyrimidinverbindungen - Google Patents
6-aryl-pyrimidinverbindungenInfo
- Publication number
- DE3008693A1 DE3008693A1 DE19803008693 DE3008693A DE3008693A1 DE 3008693 A1 DE3008693 A1 DE 3008693A1 DE 19803008693 DE19803008693 DE 19803008693 DE 3008693 A DE3008693 A DE 3008693A DE 3008693 A1 DE3008693 A1 DE 3008693A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- carbon atoms
- amino
- pyrimidinol
- bromine
- 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.)
- Granted
Links
- -1 perfluoropropyl radical Chemical class 0.000 claims description 95
- 239000000460 chlorine Substances 0.000 claims description 69
- 125000004432 carbon atom Chemical group C* 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 49
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 46
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 46
- 229910052794 bromium Inorganic materials 0.000 claims description 46
- 239000011737 fluorine Substances 0.000 claims description 40
- 229910052731 fluorine Inorganic materials 0.000 claims description 40
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 39
- 229910052801 chlorine Inorganic materials 0.000 claims description 36
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 34
- 229910052740 iodine Inorganic materials 0.000 claims description 27
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 26
- 239000011630 iodine Substances 0.000 claims description 26
- 230000002265 prevention Effects 0.000 claims description 26
- 102000014150 Interferons Human genes 0.000 claims description 24
- 108010050904 Interferons Proteins 0.000 claims description 24
- LOQWIXAMWLMCQY-UHFFFAOYSA-N 2-amino-5-bromo-6-(3-fluorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Br)=C1C1=CC=CC(F)=C1 LOQWIXAMWLMCQY-UHFFFAOYSA-N 0.000 claims description 23
- 229940079322 interferon Drugs 0.000 claims description 23
- 150000003254 radicals Chemical class 0.000 claims description 23
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
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- 230000001939 inductive effect Effects 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 208000035143 Bacterial infection Diseases 0.000 claims description 7
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
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- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- CIUUIPMOFZIWIZ-UHFFFAOYSA-N Bropirimine Chemical compound NC1=NC(O)=C(Br)C(C=2C=CC=CC=2)=N1 CIUUIPMOFZIWIZ-UHFFFAOYSA-N 0.000 claims description 4
- 206010010356 Congenital anomaly Diseases 0.000 claims description 4
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- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 4
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 3
- MZYSYNKAXMNKDO-UHFFFAOYSA-N 2-amino-5-bromo-6-(2-methoxyphenyl)-1h-pyrimidin-4-one Chemical compound COC1=CC=CC=C1C1=C(Br)C(=O)N=C(N)N1 MZYSYNKAXMNKDO-UHFFFAOYSA-N 0.000 claims description 3
- WCWMVUUWTZVWHC-UHFFFAOYSA-N 2-amino-5-bromo-6-pyridin-2-yl-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Br)=C1C1=CC=CC=N1 WCWMVUUWTZVWHC-UHFFFAOYSA-N 0.000 claims description 3
- OTYQGLBBGSZIKY-UHFFFAOYSA-N 2-amino-5-iodo-6-(2-methoxyphenyl)-1h-pyrimidin-4-one Chemical compound COC1=CC=CC=C1C1=C(I)C(=O)N=C(N)N1 OTYQGLBBGSZIKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
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- 201000011510 cancer Diseases 0.000 claims description 3
- UHKUZWMIMIJLAZ-UHFFFAOYSA-N 2-amino-5-bromo-6-(2-fluorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Br)=C1C1=CC=CC=C1F UHKUZWMIMIJLAZ-UHFFFAOYSA-N 0.000 claims description 2
- DPRPYFUMFSDKEY-UHFFFAOYSA-N 2-amino-5-bromo-6-(3-chlorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Br)=C1C1=CC=CC(Cl)=C1 DPRPYFUMFSDKEY-UHFFFAOYSA-N 0.000 claims description 2
- QKSGRZHBGJWOBN-UHFFFAOYSA-N 2-amino-5-bromo-6-(3-methoxyphenyl)-1h-pyrimidin-4-one Chemical compound COC1=CC=CC(C2=C(C(=O)N=C(N)N2)Br)=C1 QKSGRZHBGJWOBN-UHFFFAOYSA-N 0.000 claims description 2
- SYGWERHRFAGJCA-UHFFFAOYSA-N 2-amino-5-chloro-6-(2-fluorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Cl)=C1C1=CC=CC=C1F SYGWERHRFAGJCA-UHFFFAOYSA-N 0.000 claims description 2
- SDNLXFAKPKNJRE-UHFFFAOYSA-N 2-amino-5-chloro-6-(2-methoxyphenyl)-1h-pyrimidin-4-one Chemical compound COC1=CC=CC=C1C1=C(Cl)C(=O)N=C(N)N1 SDNLXFAKPKNJRE-UHFFFAOYSA-N 0.000 claims description 2
- YFIFDYUYUNDVSO-UHFFFAOYSA-N 2-amino-5-chloro-6-(3-fluorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Cl)=C1C1=CC=CC(F)=C1 YFIFDYUYUNDVSO-UHFFFAOYSA-N 0.000 claims description 2
- OKNMQQVSQSQFEN-UHFFFAOYSA-N 2-amino-6-(3-fluorophenyl)-5-iodo-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(I)=C1C1=CC=CC(F)=C1 OKNMQQVSQSQFEN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical compound [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000036281 parasite infection Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 8
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 4
- FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical compound [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 claims 3
- FFHKBAKFBGNHID-UHFFFAOYSA-N 2-amino-5-bromo-6-(4-fluorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Br)=C1C1=CC=C(F)C=C1 FFHKBAKFBGNHID-UHFFFAOYSA-N 0.000 claims 1
- RFNDUVABMSOPRX-UHFFFAOYSA-N 2-amino-5-chloro-6-(3-methoxyphenyl)-1h-pyrimidin-4-one Chemical compound COC1=CC=CC(C2=C(C(=O)N=C(N)N2)Cl)=C1 RFNDUVABMSOPRX-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000006371 dihalo methyl group Chemical group 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000006372 monohalo methyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
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- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- HZCXBPTUYRYPPT-UHFFFAOYSA-N ethyl 2-(furan-2-yl)acetate Chemical compound CCOC(=O)CC1=CC=CO1 HZCXBPTUYRYPPT-UHFFFAOYSA-N 0.000 description 1
- NZRZNJONGRRTNF-UHFFFAOYSA-N ethyl 2-benzoylbutanoate Chemical compound CCOC(=O)C(CC)C(=O)C1=CC=CC=C1 NZRZNJONGRRTNF-UHFFFAOYSA-N 0.000 description 1
- SIWICBKMMHBCSU-UHFFFAOYSA-N ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(Cl)C(Cl)=C1 SIWICBKMMHBCSU-UHFFFAOYSA-N 0.000 description 1
- BOZNWXQZCYZCSH-UHFFFAOYSA-N ethyl 3-oxo-4-phenylbutanoate Chemical compound CCOC(=O)CC(=O)CC1=CC=CC=C1 BOZNWXQZCYZCSH-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000003394 haemopoietic effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- VMUWIFNDNXXSQA-UHFFFAOYSA-N hypofluorite Chemical compound F[O-] VMUWIFNDNXXSQA-UHFFFAOYSA-N 0.000 description 1
- 230000008102 immune modulation Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
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- 239000002799 interferon inducing agent Substances 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 244000000056 intracellular parasite Species 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000003292 kidney cell Anatomy 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 235000013379 molasses Nutrition 0.000 description 1
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- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 210000000822 natural killer cell Anatomy 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- TYRDEZUMAVRTEO-UHFFFAOYSA-N pyrimidin-5-ylmethanol Chemical compound OCC1=CN=CN=C1 TYRDEZUMAVRTEO-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000006215 rectal suppository Substances 0.000 description 1
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- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent 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
- 238000010998 test method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000006216 vaginal suppository Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2220579A | 1979-03-19 | 1979-03-19 | |
| US7985079A | 1979-09-28 | 1979-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3008693A1 true DE3008693A1 (de) | 1980-10-02 |
Family
ID=26695670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803008693 Granted DE3008693A1 (de) | 1979-03-19 | 1980-03-06 | 6-aryl-pyrimidinverbindungen |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPH0627070B2 (enrdf_load_html_response) |
| CH (1) | CH646958A5 (enrdf_load_html_response) |
| DE (1) | DE3008693A1 (enrdf_load_html_response) |
| FR (1) | FR2451918A1 (enrdf_load_html_response) |
| GB (1) | GB2048250B (enrdf_load_html_response) |
| IT (1) | IT1143012B (enrdf_load_html_response) |
| NL (1) | NL8001568A (enrdf_load_html_response) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0459830A1 (en) * | 1990-06-01 | 1991-12-04 | The Wellcome Foundation Limited | Pharmacologically active CNS compounds |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0111440A1 (en) * | 1982-10-15 | 1984-06-20 | Ciba-Geigy Ag | 2-Aminopyrimidines, their production and use |
| US4795812A (en) * | 1985-02-05 | 1989-01-03 | The Upjohn Company | 4-substituted-6-aryl-pyrimidine compounds |
| CA2269681A1 (en) * | 1996-12-12 | 1998-06-18 | Pharmacia & Upjohn Company Llc | Use of a 6-aryl pyrimidine compound for treating multiple sclerosis |
| US6495558B1 (en) | 1999-01-22 | 2002-12-17 | Amgen Inc. | Kinase inhibitors |
| CA2359680A1 (en) * | 1999-01-22 | 2000-07-27 | David M. Armistead | Kinase inhibitors |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2704285A (en) * | 1954-06-17 | 1955-03-15 | Searle & Co | 2-amino-5-(lower alkyl)-6-substituted phenyl-4-pyrimidols |
| US2723977A (en) * | 1953-07-29 | 1955-11-15 | Searle & Co | 5, 6-disubstituted 2-amino-4-pyrimidols |
| US2723978A (en) * | 1954-01-14 | 1955-11-15 | Searle & Co | 2-amino-5-alkenyl-6-phenyl-4-pyrimidols |
| US3932617A (en) * | 1974-05-24 | 1976-01-13 | The Upjohn Company | Interferon induction |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2688019A (en) * | 1951-08-25 | 1954-08-31 | Burroughs Wellcome Co | 6-aryl-2,4-diamino pyrimidines and process of preparing same |
| US2710867A (en) * | 1954-03-12 | 1955-06-14 | Searle & Co | New 2-amino-4-pyrimidol derivatives |
| US2748121A (en) * | 1954-06-17 | 1956-05-29 | Searle & Co | 6-nitroaryl derivatives of 2-amino-4-pyrimidols |
| US3281420A (en) * | 1966-01-27 | 1966-10-25 | Searle & Co | Carboxylic acid [2-(2-amino-4-azido-6-phenyl-5-pyrimidinyl)-1-methylethylidene] hydrazides and intermediate |
| US3412094A (en) * | 1967-06-21 | 1968-11-19 | Searle & Co | 5-alkyl-2-amino-4-azido-6-phenylpyrimidines and congeners |
-
1980
- 1980-03-06 DE DE19803008693 patent/DE3008693A1/de active Granted
- 1980-03-10 IT IT48119/80A patent/IT1143012B/it active
- 1980-03-14 CH CH204380A patent/CH646958A5/de not_active IP Right Cessation
- 1980-03-17 GB GB8008979A patent/GB2048250B/en not_active Expired
- 1980-03-17 NL NL8001568A patent/NL8001568A/nl active Search and Examination
- 1980-03-18 FR FR8006015A patent/FR2451918A1/fr active Granted
-
1991
- 1991-08-12 JP JP3201754A patent/JPH0627070B2/ja not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2723977A (en) * | 1953-07-29 | 1955-11-15 | Searle & Co | 5, 6-disubstituted 2-amino-4-pyrimidols |
| US2723978A (en) * | 1954-01-14 | 1955-11-15 | Searle & Co | 2-amino-5-alkenyl-6-phenyl-4-pyrimidols |
| US2704285A (en) * | 1954-06-17 | 1955-03-15 | Searle & Co | 2-amino-5-(lower alkyl)-6-substituted phenyl-4-pyrimidols |
| US3932617A (en) * | 1974-05-24 | 1976-01-13 | The Upjohn Company | Interferon induction |
Non-Patent Citations (2)
| Title |
|---|
| J. Med. Chem. 23, 1980, S.237-239 * |
| J. Med. Chem. 28, 1985, S. 1864-9 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0459830A1 (en) * | 1990-06-01 | 1991-12-04 | The Wellcome Foundation Limited | Pharmacologically active CNS compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8048119A0 (it) | 1980-03-10 |
| FR2451918B1 (enrdf_load_html_response) | 1984-01-06 |
| JPH0517451A (ja) | 1993-01-26 |
| IT1143012B (it) | 1986-10-22 |
| JPH0627070B2 (ja) | 1994-04-13 |
| NL8001568A (nl) | 1980-09-23 |
| GB2048250B (en) | 1983-04-27 |
| FR2451918A1 (fr) | 1980-10-17 |
| GB2048250A (en) | 1980-12-10 |
| CH646958A5 (de) | 1984-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |