CH511239A - Verfahren zur Herstellung von 5-Benzylpyrimidinen - Google Patents
Verfahren zur Herstellung von 5-BenzylpyrimidinenInfo
- Publication number
- CH511239A CH511239A CH237967A CH237967A CH511239A CH 511239 A CH511239 A CH 511239A CH 237967 A CH237967 A CH 237967A CH 237967 A CH237967 A CH 237967A CH 511239 A CH511239 A CH 511239A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compound
- group
- compounds
- reaction
- Prior art date
Links
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 6
- OOLOAWZLPBDRJQ-UHFFFAOYSA-N 2-benzylpyrimidine Chemical class N=1C=CC=NC=1CC1=CC=CC=C1 OOLOAWZLPBDRJQ-UHFFFAOYSA-N 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 45
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 6
- NPYPQKXJJZZSAX-UHFFFAOYSA-N 5-benzylpyrimidine Chemical class C=1N=CN=CC=1CC1=CC=CC=C1 NPYPQKXJJZZSAX-UHFFFAOYSA-N 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 21
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 10
- BUUOTZKSGGVVAY-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-2,6-dimethoxyphenol Chemical compound COC1=CC(CN(C)C)=CC(OC)=C1O BUUOTZKSGGVVAY-UHFFFAOYSA-N 0.000 abstract description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract description 2
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HPOCGNHBIFZCAN-UHFFFAOYSA-N 4-[(2,4-diaminopyrimidin-5-yl)methyl]-2,6-dimethoxyphenol Chemical compound COC1=C(O)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 HPOCGNHBIFZCAN-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000155 melt Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- -1 solutes Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- HWLAHKWVFFIJLY-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-2,6-dimethoxyphenol;hydrochloride Chemical compound Cl.COC1=CC(CN(C)C)=CC(OC)=C1O HWLAHKWVFFIJLY-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
- JTTIOYHBNXDJOD-UHFFFAOYSA-N 2,4,6-triaminopyrimidine Chemical compound NC1=CC(N)=NC(N)=N1 JTTIOYHBNXDJOD-UHFFFAOYSA-N 0.000 description 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- GCGONLKCVURQKO-UHFFFAOYSA-N 2-amino-5-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-1H-pyrimidin-6-one Chemical compound NC1=NC=C(C(=N1)O)CC1=CC(=C(C(=C1)OC)O)OC GCGONLKCVURQKO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- UENCAEKPVSVELE-UHFFFAOYSA-N 2,6-diamino-5-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-1h-pyrimidin-4-one Chemical compound COC1=C(O)C(OC)=CC(CC=2C(=NC(N)=NC=2N)O)=C1 UENCAEKPVSVELE-UHFFFAOYSA-N 0.000 description 1
- VMZVBRIIHDRYGK-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VMZVBRIIHDRYGK-UHFFFAOYSA-N 0.000 description 1
- XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical compound NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- OWESLNUTAHNAGR-UHFFFAOYSA-N 4-[(2,4-diamino-6-methylpyrimidin-5-yl)methyl]-2,6-dimethoxyphenol Chemical compound COC1=C(O)C(OC)=CC(CC=2C(=NC(N)=NC=2C)N)=C1 OWESLNUTAHNAGR-UHFFFAOYSA-N 0.000 description 1
- XXRUQNNAKXZSOS-UHFFFAOYSA-N 5-(chloromethyl)-1,2,3-trimethoxybenzene Chemical compound COC1=CC(CCl)=CC(OC)=C1OC XXRUQNNAKXZSOS-UHFFFAOYSA-N 0.000 description 1
- LMMYRVSIBONOSJ-UHFFFAOYSA-N 5-[(4-butoxy-3,5-dimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OCCCC)=C(OC)C=C1CC1=CN=C(N)N=C1N LMMYRVSIBONOSJ-UHFFFAOYSA-N 0.000 description 1
- GJSFSLHCFDZEEE-UHFFFAOYSA-N 5-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-1H-pyrimidine-2,4-dione Chemical compound COC=1C=C(CC=2C(NC(NC2)=O)=O)C=C(C1O)OC GJSFSLHCFDZEEE-UHFFFAOYSA-N 0.000 description 1
- GBSVHIRGEFPSIA-UHFFFAOYSA-N 5-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-6-methyl-1h-pyrimidine-2,4-dione Chemical compound COC1=C(O)C(OC)=CC(CC=2C(NC(=O)NC=2C)=O)=C1 GBSVHIRGEFPSIA-UHFFFAOYSA-N 0.000 description 1
- HETTWAYXYADCHJ-UHFFFAOYSA-N 5-[[3,5-dimethoxy-4-[(3,4,5-trimethoxyphenyl)methoxy]phenyl]methyl]pyrimidine-2,4-diamine Chemical compound COC1=C(OC)C(OC)=CC(COC=2C(=CC(CC=3C(=NC(N)=NC=3)N)=CC=2OC)OC)=C1 HETTWAYXYADCHJ-UHFFFAOYSA-N 0.000 description 1
- ROAWFYCFJHYCMG-UHFFFAOYSA-N 5-[[4-(3-chloropropoxy)-3,5-dimethoxyphenyl]methyl]pyrimidine-2,4-diamine Chemical compound COC1=C(OCCCCl)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 ROAWFYCFJHYCMG-UHFFFAOYSA-N 0.000 description 1
- KUPCMNHSRONILW-UHFFFAOYSA-N 6-methyl-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2C)N)=C1 KUPCMNHSRONILW-UHFFFAOYSA-N 0.000 description 1
- HERHQNVDSHUKAK-UHFFFAOYSA-N 6-methylpyrimidine-2,4-diamine Chemical compound CC1=CC(N)=NC(N)=N1 HERHQNVDSHUKAK-UHFFFAOYSA-N 0.000 description 1
- IPFIEHIRBSTAKA-UHFFFAOYSA-N 6-piperidin-1-ylpyrimidine-2,4-diamine Chemical compound NC1=NC(N)=CC(N2CCCCC2)=N1 IPFIEHIRBSTAKA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZXRCAYWYTOIRQS-UHFFFAOYSA-N hydron;phenol;chloride Chemical compound Cl.OC1=CC=CC=C1 ZXRCAYWYTOIRQS-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- FPCVVKSVMZABES-UHFFFAOYSA-N pyrimidine;hydrate;hydrochloride Chemical compound O.Cl.C1=CN=CN=C1 FPCVVKSVMZABES-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Lubricants (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Liquid Crystal Substances (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB737666A GB1128234A (en) | 1966-02-19 | 1966-02-19 | 5-benzylpyrimidine derivatives and process for the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH511239A true CH511239A (de) | 1971-08-15 |
Family
ID=9831956
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH191468A CH513179A (de) | 1966-02-19 | 1967-02-17 | Verfahren zur Herstellung von 5-Benzylpyrimidinen |
| CH237967A CH511239A (de) | 1966-02-19 | 1967-02-17 | Verfahren zur Herstellung von 5-Benzylpyrimidinen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH191468A CH513179A (de) | 1966-02-19 | 1967-02-17 | Verfahren zur Herstellung von 5-Benzylpyrimidinen |
Country Status (16)
| Country | Link |
|---|---|
| AT (2) | AT275534B (fr) |
| BE (1) | BE694244A (fr) |
| CA (1) | CA977754A (fr) |
| CH (2) | CH513179A (fr) |
| DE (2) | DE1795635C3 (fr) |
| DK (2) | DK120344B (fr) |
| ES (1) | ES336945A1 (fr) |
| FI (1) | FI49714C (fr) |
| FR (1) | FR6595M (fr) |
| GB (1) | GB1128234A (fr) |
| GR (1) | GR33641B (fr) |
| IL (1) | IL27424A (fr) |
| MY (1) | MY7100226A (fr) |
| NL (1) | NL146811B (fr) |
| NO (1) | NO124601B (fr) |
| SE (2) | SE338998B (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE789904A (fr) * | 1971-10-12 | 1973-04-10 | Wellcome Found | Procedes de synthese organique |
| NO791699L (no) * | 1978-05-24 | 1979-11-27 | Wellcome Found | Benzylpyrimidinforbindelser og fremgangsmaate til deres fremstilling |
| DE2944145A1 (de) | 1979-11-02 | 1981-05-14 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur herstellung von 2,4-diaminopyrimidin |
-
1966
- 1966-02-19 GB GB737666A patent/GB1128234A/en not_active Expired
-
1967
- 1967-02-13 IL IL2742467A patent/IL27424A/xx unknown
- 1967-02-13 GR GR670133641A patent/GR33641B/el unknown
- 1967-02-15 CA CA983,015A patent/CA977754A/en not_active Expired
- 1967-02-16 NO NO16687667A patent/NO124601B/no unknown
- 1967-02-16 AT AT409368A patent/AT275534B/de active
- 1967-02-16 AT AT153867A patent/AT270653B/de active
- 1967-02-17 BE BE694244D patent/BE694244A/xx not_active IP Right Cessation
- 1967-02-17 FI FI48067A patent/FI49714C/fi active
- 1967-02-17 CH CH191468A patent/CH513179A/de not_active IP Right Cessation
- 1967-02-17 DE DE19671795635 patent/DE1795635C3/de not_active Expired
- 1967-02-17 CH CH237967A patent/CH511239A/de not_active IP Right Cessation
- 1967-02-17 ES ES336945A patent/ES336945A1/es not_active Expired
- 1967-02-17 DE DE1967W0043385 patent/DE1720012B2/de active Granted
- 1967-02-17 NL NL6702397A patent/NL146811B/xx not_active IP Right Cessation
- 1967-02-20 DK DK91167A patent/DK120344B/da not_active IP Right Cessation
- 1967-02-20 SE SE227867A patent/SE338998B/xx unknown
- 1967-02-20 SE SE796270A patent/SE390412B/xx unknown
- 1967-05-16 FR FR106573A patent/FR6595M/fr not_active Expired
-
1971
- 1971-02-10 DK DK59371A patent/DK128247B/da not_active IP Right Cessation
- 1971-12-31 MY MY7100226A patent/MY7100226A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE338998B (fr) | 1971-09-27 |
| DE1720012A1 (de) | 1972-04-06 |
| NL6702397A (fr) | 1967-08-21 |
| DE1795635C3 (de) | 1978-05-11 |
| FI49714B (fr) | 1975-06-02 |
| GB1128234A (en) | 1968-09-25 |
| MY7100226A (en) | 1971-12-31 |
| CA977754A (en) | 1975-11-11 |
| NO124601B (fr) | 1972-05-08 |
| FR6595M (fr) | 1969-01-06 |
| DK128247B (da) | 1974-03-25 |
| IL27424A (en) | 1971-02-25 |
| GR33641B (el) | 1968-01-03 |
| DK120344B (da) | 1971-05-17 |
| DE1795635A1 (de) | 1972-10-19 |
| CH513179A (de) | 1971-09-30 |
| DE1720012B2 (de) | 1977-06-08 |
| AT275534B (de) | 1969-10-27 |
| NL146811B (nl) | 1975-08-15 |
| SE390412B (sv) | 1976-12-20 |
| BE694244A (fr) | 1967-08-17 |
| FI49714C (fi) | 1975-09-10 |
| AT270653B (de) | 1969-05-12 |
| ES336945A1 (es) | 1968-01-16 |
| DE1795635B2 (de) | 1977-09-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |