NL8001568A - Pyrimidinederivaten en farmaceutische preparaten daaruit bereid. - Google Patents
Pyrimidinederivaten en farmaceutische preparaten daaruit bereid. Download PDFInfo
- Publication number
- NL8001568A NL8001568A NL8001568A NL8001568A NL8001568A NL 8001568 A NL8001568 A NL 8001568A NL 8001568 A NL8001568 A NL 8001568A NL 8001568 A NL8001568 A NL 8001568A NL 8001568 A NL8001568 A NL 8001568A
- Authority
- NL
- Netherlands
- Prior art keywords
- carbon atoms
- amino
- pyrimidinol
- compound according
- alkyl
- Prior art date
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- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims description 82
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 102000014150 Interferons Human genes 0.000 claims description 38
- 108010050904 Interferons Proteins 0.000 claims description 38
- 229940079322 interferon Drugs 0.000 claims description 37
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 36
- 239000000460 chlorine Substances 0.000 claims description 36
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 34
- 229910052794 bromium Inorganic materials 0.000 claims description 34
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 239000011737 fluorine Substances 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 30
- -1 monosubstituted phenyl Chemical group 0.000 claims description 29
- LOQWIXAMWLMCQY-UHFFFAOYSA-N 2-amino-5-bromo-6-(3-fluorophenyl)-1h-pyrimidin-4-one Chemical group N1C(N)=NC(=O)C(Br)=C1C1=CC=CC(F)=C1 LOQWIXAMWLMCQY-UHFFFAOYSA-N 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 230000015572 biosynthetic process Effects 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 18
- 239000011630 iodine Substances 0.000 claims description 18
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 230000009385 viral infection Effects 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 150000003230 pyrimidines Chemical class 0.000 claims description 8
- JBQRDRKWCBEQKP-UHFFFAOYSA-N 2-amino-5-iodo-6-phenyl-1h-pyrimidin-4-one Chemical group N1C(N)=NC(=O)C(I)=C1C1=CC=CC=C1 JBQRDRKWCBEQKP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 7
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 7
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
- 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 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- VOSRRSSOXKZTFS-UHFFFAOYSA-N 2-amino-5-chloro-6-phenyl-1h-pyrimidin-4-one Chemical group N1C(N)=NC(=O)C(Cl)=C1C1=CC=CC=C1 VOSRRSSOXKZTFS-UHFFFAOYSA-N 0.000 claims description 5
- 208000035143 Bacterial infection Diseases 0.000 claims description 5
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- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
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- 230000001939 inductive effect Effects 0.000 claims description 5
- DPRPYFUMFSDKEY-UHFFFAOYSA-N 2-amino-5-bromo-6-(3-chlorophenyl)-1h-pyrimidin-4-one Chemical group N1C(N)=NC(=O)C(Br)=C1C1=CC=CC(Cl)=C1 DPRPYFUMFSDKEY-UHFFFAOYSA-N 0.000 claims description 4
- DXBYKELYJFUZHI-UHFFFAOYSA-N 2-amino-6-(3-chlorophenyl)-5-iodo-1h-pyrimidin-4-one Chemical group N1C(N)=NC(=O)C(I)=C1C1=CC=CC(Cl)=C1 DXBYKELYJFUZHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 claims description 4
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 4
- SDNLXFAKPKNJRE-UHFFFAOYSA-N 2-amino-5-chloro-6-(2-methoxyphenyl)-1h-pyrimidin-4-one Chemical group COC1=CC=CC=C1C1=C(Cl)C(=O)N=C(N)N1 SDNLXFAKPKNJRE-UHFFFAOYSA-N 0.000 claims description 3
- SHRZUNZYCBOEBR-UHFFFAOYSA-N 2-amino-5-chloro-6-(3-chlorophenyl)-1h-pyrimidin-4-one Chemical group N1C(N)=NC(=O)C(Cl)=C1C1=CC=CC(Cl)=C1 SHRZUNZYCBOEBR-UHFFFAOYSA-N 0.000 claims description 3
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- RFNDUVABMSOPRX-UHFFFAOYSA-N 2-amino-5-chloro-6-(3-methoxyphenyl)-1h-pyrimidin-4-one Chemical group COC1=CC=CC(C2=C(C(=O)N=C(N)N2)Cl)=C1 RFNDUVABMSOPRX-UHFFFAOYSA-N 0.000 claims description 3
- SUGLSVRAIXNUJC-UHFFFAOYSA-N 2-amino-5-chloro-6-(3-propoxyphenyl)-1h-pyrimidin-4-one Chemical group CCCOC1=CC=CC(C2=C(C(=O)N=C(N)N2)Cl)=C1 SUGLSVRAIXNUJC-UHFFFAOYSA-N 0.000 claims description 3
- STOMVMLFBPMGFN-UHFFFAOYSA-N 2-amino-5-iodo-6-[3-(trifluoromethyl)phenyl]-1h-pyrimidin-4-one Chemical group N1C(N)=NC(=O)C(I)=C1C1=CC=CC(C(F)(F)F)=C1 STOMVMLFBPMGFN-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004429 atom Chemical group 0.000 claims description 3
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- YRCCTKMQIARANK-UHFFFAOYSA-N 2-amino-5-bromo-6-(3,5-dimethoxyphenyl)-1h-pyrimidin-4-one Chemical group COC1=CC(OC)=CC(C2=C(C(=O)N=C(N)N2)Br)=C1 YRCCTKMQIARANK-UHFFFAOYSA-N 0.000 claims description 2
- UOYAMPHASAGZFC-UHFFFAOYSA-N 2-amino-5-bromo-6-[3-(2-ethoxyethyl)phenyl]-1h-pyrimidin-4-one Chemical group CCOCCC1=CC=CC(C=2C(=C(O)N=C(N)N=2)Br)=C1 UOYAMPHASAGZFC-UHFFFAOYSA-N 0.000 claims description 2
- VXTXTXSPZIZKTK-UHFFFAOYSA-N 2-amino-5-iodo-6-(3-nitrophenyl)-1h-pyrimidin-4-one Chemical group N1C(N)=NC(=O)C(I)=C1C1=CC=CC([N+]([O-])=O)=C1 VXTXTXSPZIZKTK-UHFFFAOYSA-N 0.000 claims description 2
- ANNSJLJZORKOJG-UHFFFAOYSA-N 2-amino-6-(3-bromophenyl)-5-iodo-1h-pyrimidin-4-one Chemical group N1C(N)=NC(=O)C(I)=C1C1=CC=CC(Br)=C1 ANNSJLJZORKOJG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 208000025643 Congenital hypogammaglobulinaemia Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 208000029192 congenital agammaglobulinemia Diseases 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
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- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000007596 consolidation process Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 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
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 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
- 208000035475 disorder Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000012055 enteric layer Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WWFYJJHEBDWEJF-UHFFFAOYSA-N ethyl 3-(3-chlorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC(Cl)=C1 WWFYJJHEBDWEJF-UHFFFAOYSA-N 0.000 description 1
- DGCZHKABHPDNCC-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(Cl)C=C1 DGCZHKABHPDNCC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 210000003958 hematopoietic stem cell Anatomy 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 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 compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000004957 immunoregulator effect Effects 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 239000002799 interferon inducing agent Substances 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 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
- 210000002540 macrophage Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 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
- 230000037125 natural defense Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 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
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940042126 oral powder Drugs 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 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
- 230000002335 preservative effect Effects 0.000 description 1
- 238000003825 pressing Methods 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
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000010298 pulverizing process 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
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 201000005404 rubella Diseases 0.000 description 1
- 238000007789 sealing Methods 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
- 235000013874 shellac Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 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
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000007920 subcutaneous administration 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
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000010497 wheat germ oil Substances 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2220579A | 1979-03-19 | 1979-03-19 | |
| US2220579 | 1979-03-19 | ||
| US7985079A | 1979-09-28 | 1979-09-28 | |
| US7985079 | 1979-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8001568A true NL8001568A (nl) | 1980-09-23 |
Family
ID=26695670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8001568A NL8001568A (nl) | 1979-03-19 | 1980-03-17 | Pyrimidinederivaten en farmaceutische preparaten daaruit bereid. |
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) |
Families Citing this family (6)
| 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 |
| GB9012311D0 (en) * | 1990-06-01 | 1990-07-18 | Wellcome Found | Pharmacologically active cns 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 |
Family Cites Families (9)
| 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 |
| 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 |
| US2710867A (en) * | 1954-03-12 | 1955-06-14 | Searle & Co | New 2-amino-4-pyrimidol derivatives |
| US2704285A (en) * | 1954-06-17 | 1955-03-15 | Searle & Co | 2-amino-5-(lower alkyl)-6-substituted phenyl-4-pyrimidols |
| 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 |
| US3932617A (en) * | 1974-05-24 | 1976-01-13 | The Upjohn Company | Interferon induction |
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| IT8048119A0 (it) | 1980-03-10 |
| DE3008693A1 (de) | 1980-10-02 |
| FR2451918B1 (enrdf_load_html_response) | 1984-01-06 |
| JPH0517451A (ja) | 1993-01-26 |
| IT1143012B (it) | 1986-10-22 |
| JPH0627070B2 (ja) | 1994-04-13 |
| 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 |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| DNT | Communications of changes of names of applicants whose applications have been laid open to public inspection |
Free format text: PHARMACIA & UPJOHN COMPANY |
|
| BN | A decision not to publish the application has become irrevocable |