NO136046B - - Google Patents
Download PDFInfo
- Publication number
- NO136046B NO136046B NO1311/72A NO131172A NO136046B NO 136046 B NO136046 B NO 136046B NO 1311/72 A NO1311/72 A NO 1311/72A NO 131172 A NO131172 A NO 131172A NO 136046 B NO136046 B NO 136046B
- Authority
- NO
- Norway
- Prior art keywords
- diamino
- group
- carbon atoms
- pyrimidine
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 24
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- XHPZVBGIPQQTQW-UHFFFAOYSA-N 5-benzylpyrimidine-2,4-diamine Chemical class NC1=NC(N)=NC=C1CC1=CC=CC=C1 XHPZVBGIPQQTQW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000007868 Raney catalyst Substances 0.000 claims description 10
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- CEFCYXFPPQNRCK-UHFFFAOYSA-N 4-[(2,4-diaminopyrimidin-5-yl)methyl]phenol Chemical compound NC1=NC(N)=NC=C1CC1=CC=C(O)C=C1 CEFCYXFPPQNRCK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 96
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 28
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 14
- 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 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 11
- -1 2,4-disubstituted pyrimidine Chemical class 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 229960001082 trimethoprim Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical class COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- LTROKMZJOJZVBF-UHFFFAOYSA-N 6-methylsulfanylpyrimidine-2,4-diamine Chemical compound CSC1=CC(N)=NC(N)=N1 LTROKMZJOJZVBF-UHFFFAOYSA-N 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- LDBTVAXGKYIFHO-UHFFFAOYSA-N diaveridine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=CN=C(N)N=C1N LDBTVAXGKYIFHO-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- SSIZLKDLDKIHEV-UHFFFAOYSA-N 2,6-dibromophenol Chemical compound OC1=C(Br)C=CC=C1Br SSIZLKDLDKIHEV-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- JGNNNRAVYCMSPQ-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-2,6-diethylphenol Chemical compound CCC1=CC(CN(C)C)=CC(CC)=C1O JGNNNRAVYCMSPQ-UHFFFAOYSA-N 0.000 description 2
- PWXGOQREGLRIRB-UHFFFAOYSA-N 5-[(3,5-ditert-butyl-4-methoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1CC1=CN=C(N)N=C1N PWXGOQREGLRIRB-UHFFFAOYSA-N 0.000 description 2
- KEEYRKYKLYARHO-UHFFFAOYSA-N 5-[(4,5-dimethoxy-2-methylphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OC)=CC(C)=C1CC1=CN=C(N)N=C1N KEEYRKYKLYARHO-UHFFFAOYSA-N 0.000 description 2
- SMLJPKAFENVMOT-UHFFFAOYSA-N 5-[[4-methoxy-3,5-di(propan-2-yl)phenyl]methyl]pyrimidine-2,4-diamine Chemical compound C1=C(C(C)C)C(OC)=C(C(C)C)C=C1CC1=CN=C(N)N=C1N SMLJPKAFENVMOT-UHFFFAOYSA-N 0.000 description 2
- GUYGQFUATGGJRN-UHFFFAOYSA-N 6-ethylsulfanylpyrimidine-2,4-diamine Chemical compound CCSC1=CC(N)=NC(N)=N1 GUYGQFUATGGJRN-UHFFFAOYSA-N 0.000 description 2
- FUJMHPXCGSEURK-UHFFFAOYSA-N Cl.NC1=NC(=C(C(=N1)N)CC1=CC(=C(C(=C1)CC)OC)CC)SC Chemical compound Cl.NC1=NC(=C(C(=N1)N)CC1=CC(=C(C(=C1)CC)OC)CC)SC FUJMHPXCGSEURK-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241000588769 Proteus <enterobacteria> Species 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004354 sulfur functional group Chemical group 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- 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
- SOUUDGAWOJKDRN-UHFFFAOYSA-N 2,6-diamino-1h-pyrimidine-4-thione Chemical compound NC1=CC(=S)N=C(N)N1 SOUUDGAWOJKDRN-UHFFFAOYSA-N 0.000 description 1
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 1
- METWAQRCMRWDAW-UHFFFAOYSA-N 2,6-diethylphenol Chemical compound CCC1=CC=CC(CC)=C1O METWAQRCMRWDAW-UHFFFAOYSA-N 0.000 description 1
- NAILKKRDWBJCNH-UHFFFAOYSA-N 2,6-dipropylphenol Chemical compound CCCC1=CC=CC(CCC)=C1O NAILKKRDWBJCNH-UHFFFAOYSA-N 0.000 description 1
- FUMUIRCRBKLQCR-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(2,4-diamino-6-methylsulfanylpyrimidin-5-yl)methyl]phenol Chemical compound NC1=NC(=C(C(=N1)N)CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)SC FUMUIRCRBKLQCR-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
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- BCVZHOXCSLFFBW-UHFFFAOYSA-N 4-(aminomethyl)-2,6-dimethoxyphenol;hydrochloride Chemical compound Cl.COC1=CC(CN)=CC(OC)=C1O BCVZHOXCSLFFBW-UHFFFAOYSA-N 0.000 description 1
- QASHDQVZICZBRI-UHFFFAOYSA-N 4-[(2,4-diamino-6-methylsulfanylpyrimidin-5-yl)methyl]-2,6-di(propan-2-yl)phenol Chemical compound CSC1=NC(N)=NC(N)=C1CC1=CC(C(C)C)=C(O)C(=C1)C(C)C QASHDQVZICZBRI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DEYFSRVIHDNQHT-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-2,6-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC(CN(C)C)=CC(C(C)C)=C1O DEYFSRVIHDNQHT-UHFFFAOYSA-N 0.000 description 1
- BUUOTZKSGGVVAY-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-2,6-dimethoxyphenol Chemical compound COC1=CC(CN(C)C)=CC(OC)=C1O BUUOTZKSGGVVAY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HIIDEAQIXRMMJU-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-2,6-dipropylphenol Chemical compound CCCC1=CC(CN(C)C)=CC(CCC)=C1O HIIDEAQIXRMMJU-UHFFFAOYSA-N 0.000 description 1
- MYDUCDPLWNAGTN-UHFFFAOYSA-N 5-[(3,4-dimethoxy-2-methylphenyl)methyl]pyrimidine-2,4-diamine Chemical compound CC1=C(OC)C(OC)=CC=C1CC1=CN=C(N)N=C1N MYDUCDPLWNAGTN-UHFFFAOYSA-N 0.000 description 1
- MBQNMZNKKOPPEI-UHFFFAOYSA-N 5-[(3,5-diethyl-4-octoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound NC1=NC=C(C(=N1)N)CC1=CC(=C(C(=C1)CC)OCCCCCCCC)CC MBQNMZNKKOPPEI-UHFFFAOYSA-N 0.000 description 1
- AIDGHKYTWCYXHH-UHFFFAOYSA-N 6-hexylsulfanylpyrimidine-2,4-diamine Chemical compound NC1=NC(=CC(=N1)N)SCCCCCC AIDGHKYTWCYXHH-UHFFFAOYSA-N 0.000 description 1
- VEVXEIZWSIBHLL-UHFFFAOYSA-N 6-methylsulfanyl-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2N)SC)=C1 VEVXEIZWSIBHLL-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 108010022394 Threonine synthase Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-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
- 230000008238 biochemical pathway Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000002192 coccidiostatic effect Effects 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 229950000246 diaveridine Drugs 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 102000004419 dihydrofolate reductase Human genes 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000008191 folinic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002500 ions 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229960003068 ormetoprim Drugs 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 description 1
- 229960000973 sulfadimethoxine Drugs 0.000 description 1
- 229960005404 sulfamethoxazole Drugs 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000002211 ultraviolet spectrum 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
- C07D239/48—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
- C07D239/48—Two nitrogen atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L2224/2612—Auxiliary members for layer connectors, e.g. spacers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO762090A NO138531C (no) | 1971-04-16 | 1976-06-16 | 2,4-diamino-5-benzyl-6-tiopyrimidiner for anvendelse som mellomprodukter til fremstilling av 2,4-diamino-5-benzyl-pyrimidiner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB964071A GB1401612A (en) | 1971-04-16 | 1971-04-16 | 2,4-diamino-5-benzylpyrimidines and preparations thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO136046B true NO136046B (de) | 1977-04-04 |
| NO136046C NO136046C (no) | 1977-07-13 |
Family
ID=9875907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1311/72A NO136046C (no) | 1971-04-16 | 1972-04-14 | Fremgangsm}te til fremstilling av 2,4-diamino-5-benzylpyrimidiner. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US3822264A (de) |
| JP (1) | JPS5324433B1 (de) |
| AR (1) | AR193078A1 (de) |
| AT (1) | AT316560B (de) |
| AU (1) | AU468410B2 (de) |
| BE (1) | BE782154R (de) |
| CA (1) | CA978954A (de) |
| CH (1) | CH565159A5 (de) |
| CS (2) | CS178140B2 (de) |
| DD (1) | DD97653A6 (de) |
| DE (2) | DE2265413C2 (de) |
| DK (1) | DK132221C (de) |
| ES (1) | ES401796A2 (de) |
| FI (1) | FI57400C (de) |
| FR (1) | FR2133753B2 (de) |
| GB (1) | GB1401612A (de) |
| HU (1) | HU165865B (de) |
| IE (1) | IE36289B1 (de) |
| IL (1) | IL39221A (de) |
| NL (1) | NL163214C (de) |
| NO (1) | NO136046C (de) |
| PL (1) | PL75399B3 (de) |
| SE (2) | SE405118B (de) |
| ZA (1) | ZA722533B (de) |
| ZM (1) | ZM7072A1 (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4515948A (en) * | 1973-09-12 | 1985-05-07 | Hoffmann-La Roche Inc. | 2,4-Diamino-5-(4-amino and 4-dimethylamino-3,5-dimethoxy benzyl)pyrimidines |
| US4039543A (en) * | 1974-12-24 | 1977-08-02 | Hoffmann-La Roche Inc. | Benzylpyrimidines |
| DE2720771C3 (de) * | 1977-05-09 | 1979-11-29 | Ludwig Heumann & Co Gmbh, 8500 Nuernberg | 2,4-Diamino-5-(33-dimethoxy-4thioalkyl-benzyD-pyrimidine, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| JPS5888368A (ja) * | 1981-11-09 | 1983-05-26 | ザ・ウエルカム・フアウンデ−シヨン・リミテツド | ベンジルピリミジン誘導体の製造法 |
| DE3250132C2 (de) * | 1981-11-09 | 1997-01-16 | Mallinckrodt Veterinary Inc | Verfahren zur Herstellung von 2,4-Diamino-5-benzyl-pyrimidinen und neue Zwischenprodukte des Verfahrens |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR94837E (fr) * | 1966-02-19 | 1969-11-28 | Wellcome Found | Procédé de préparation de dérivés de la pyrimidine. |
-
1971
- 1971-04-16 GB GB964071A patent/GB1401612A/en not_active Expired
-
1972
- 1972-04-12 US US00243400A patent/US3822264A/en not_active Expired - Lifetime
- 1972-04-14 PL PL1972154734A patent/PL75399B3/pl unknown
- 1972-04-14 DE DE2265413A patent/DE2265413C2/de not_active Expired
- 1972-04-14 IE IE490/72A patent/IE36289B1/xx unknown
- 1972-04-14 NL NL7205046.A patent/NL163214C/xx not_active IP Right Cessation
- 1972-04-14 CA CA139,775A patent/CA978954A/en not_active Expired
- 1972-04-14 DD DD162303A patent/DD97653A6/xx unknown
- 1972-04-14 AU AU41177/72A patent/AU468410B2/en not_active Expired
- 1972-04-14 HU HUWE458A patent/HU165865B/hu unknown
- 1972-04-14 FR FR7213216A patent/FR2133753B2/fr not_active Expired
- 1972-04-14 CS CS6569A patent/CS178140B2/cs unknown
- 1972-04-14 FI FI1064/72A patent/FI57400C/fi active
- 1972-04-14 BE BE782154A patent/BE782154R/xx active
- 1972-04-14 DE DE2218221A patent/DE2218221C3/de not_active Expired
- 1972-04-14 DK DK184272A patent/DK132221C/da not_active IP Right Cessation
- 1972-04-14 CH CH554472A patent/CH565159A5/xx not_active IP Right Cessation
- 1972-04-14 JP JP3763872A patent/JPS5324433B1/ja active Pending
- 1972-04-14 SE SE7204848A patent/SE405118B/xx unknown
- 1972-04-14 AR AR241467A patent/AR193078A1/es active
- 1972-04-14 NO NO1311/72A patent/NO136046C/no unknown
- 1972-04-14 IL IL39221A patent/IL39221A/xx unknown
- 1972-04-14 ZA ZA722533A patent/ZA722533B/xx unknown
- 1972-04-14 AT AT325372A patent/AT316560B/de not_active IP Right Cessation
- 1972-04-14 ZM ZM70/72*UA patent/ZM7072A1/xx unknown
- 1972-04-14 CS CS2540A patent/CS178105B2/cs unknown
- 1972-04-15 ES ES401796A patent/ES401796A2/es not_active Expired
-
1975
- 1975-04-08 SE SE7503993A patent/SE417097B/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO147903B (no) | Gassavfuktingsapparat. | |
| NO136148B (no) | Isomerisk meget rene n-substituerte beta-amino-alfa-benzylakrylonitriler samt fremgangsm}te for fremstilling av disse. | |
| US2602794A (en) | Process for preparation of x-amino-s | |
| NO136046B (de) | ||
| CN110981816B (zh) | 一种4-氨基-2.6-二甲氧基嘧啶的合成方法 | |
| Braker et al. | Substituted Sulfanilamidopyrimidines1 | |
| Rose | 663. New syntheses based on 5-aminopyrimidines | |
| Stefanović et al. | Condensation of isatin with diketones | |
| Curd et al. | 71. Synthetic antimalarials. Part IV. 2-Phenylguanidino-4-aminoalkylamino-6-methylpyrimidines | |
| US3441560A (en) | Cyclopropyl-2-sulphanilamido-pyrimidines | |
| US3507958A (en) | Compositions and methods of treating bacteria with cyclopropyl-2-sulphanilamido-pyrimidines | |
| IL24797A (en) | N-pyrimidyl anthranilic acid derivatives and a method for the production thereof | |
| NO138531B (no) | 2,4-diamino-5-benzyl-6-tiopyrimidiner for anvendelse som mellomprodukter til fremstilling av 2,4-diamino-5-benzyl-pyrimidiner | |
| US3956327A (en) | Method of preparing 2,4-diamino-5-benzyl pyrimidines | |
| US3850927A (en) | 5-benzyl pyrimidines intermediates therefore,and method | |
| IL22365A (en) | 2,4-diamino-pyrido(2,3-d)pyrimidine derivatives | |
| US4066645A (en) | Derivatives of pyrazolo [1,5-a]pyrido[3,4-e]pyrimidine | |
| NO783775L (no) | 2,4-diamino-5-benzylpyrimidiner og fremgangsmaate ved fremstilling av disse | |
| NO137093B (no) | Fremgangsm}te til fremstilling av 2,4-diamino-5-benzylpyrimidiner | |
| CN114573515B (zh) | 一种甲氧苄啶的制备方法 | |
| CN109232579B (zh) | 一种合成培美曲塞中间体培美苯甲酸的方法 | |
| US3933807A (en) | Preparation of cyanophenols | |
| Phillips | The Role of Phenol in the Reaction of 2-amino-4-chloro-6-methylpyrimidine with Piperidine | |
| Bickel | Diaryl Acetylenic Ketones | |
| US2913462A (en) | Eahl h |