JPH0826007B2 - 新規置換２、４−ジアミノ−５−ベンジルピリミジン類、その製法およびそれを含有する抗菌剤 - Google Patents
新規置換２、４−ジアミノ−５−ベンジルピリミジン類、その製法およびそれを含有する抗菌剤Info
- Publication number
- JPH0826007B2 JPH0826007B2 JP62026178A JP2617887A JPH0826007B2 JP H0826007 B2 JPH0826007 B2 JP H0826007B2 JP 62026178 A JP62026178 A JP 62026178A JP 2617887 A JP2617887 A JP 2617887A JP H0826007 B2 JPH0826007 B2 JP H0826007B2
- Authority
- JP
- Japan
- Prior art keywords
- diamino
- group
- pyrimidine
- phenyl
- alkoxy
- 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.)
- Expired - Lifetime
Links
- 239000003242 anti bacterial agent Substances 0.000 title claims description 12
- XHPZVBGIPQQTQW-UHFFFAOYSA-N 5-benzylpyrimidine-2,4-diamine Chemical class NC1=NC(N)=NC=C1CC1=CC=CC=C1 XHPZVBGIPQQTQW-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000000034 method Methods 0.000 title description 18
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 46
- -1 acetamino group Chemical group 0.000 claims description 40
- 125000004414 alkyl thio group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 6
- 125000004660 phenylalkylthio group Chemical group 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- KWMIHIITRSBHEO-UHFFFAOYSA-N 5-[(4-decoxy-3-methoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OCCCCCCCCCC)=CC=C1CC1=CN=C(N)N=C1N KWMIHIITRSBHEO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000006266 etherification reaction Methods 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- WXVKGHVDWWXBJX-UHFFFAOYSA-N 3-morpholin-4-ylpropanenitrile Chemical compound N#CCCN1CCOCC1 WXVKGHVDWWXBJX-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- CLXMTQGVORCGJC-UHFFFAOYSA-N 5-[(3,5-dimethoxy-4-nonoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OCCCCCCCCC)=C(OC)C=C1CC1=CN=C(N)N=C1N CLXMTQGVORCGJC-UHFFFAOYSA-N 0.000 claims description 2
- KRLHWDOVSFDDAE-UHFFFAOYSA-N 5-[(3-methoxy-4-pentoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OCCCCC)=CC=C1CC1=CN=C(N)N=C1N KRLHWDOVSFDDAE-UHFFFAOYSA-N 0.000 claims description 2
- GFIIVORGRISULQ-UHFFFAOYSA-N 5-[phenyl-(4-propoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=CC(OCCC)=CC=C1C(C=1C(=NC(N)=NC=1)N)C1=CC=CC=C1 GFIIVORGRISULQ-UHFFFAOYSA-N 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 4
- KORHZHYZBJNYPV-UHFFFAOYSA-N 5-[(3,5-dimethoxy-4-octoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OCCCCCCCC)=C(OC)C=C1CC1=CN=C(N)N=C1N KORHZHYZBJNYPV-UHFFFAOYSA-N 0.000 claims 1
- BWRIOYSVQBIINF-UHFFFAOYSA-N 5-[(3-methoxyphenyl)-(4-propoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=CC(OCCC)=CC=C1C(C=1C(=NC(N)=NC=1)N)C1=CC=CC(OC)=C1 BWRIOYSVQBIINF-UHFFFAOYSA-N 0.000 claims 1
- LVZRIGPMSKMTAL-UHFFFAOYSA-N 5-[(4-heptoxy-3-methoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OCCCCCCC)=CC=C1CC1=CN=C(N)N=C1N LVZRIGPMSKMTAL-UHFFFAOYSA-N 0.000 claims 1
- VAGDNGFPEWKWTL-UHFFFAOYSA-N 5-[(4-hexoxy-3-methoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OCCCCCC)=CC=C1CC1=CN=C(N)N=C1N VAGDNGFPEWKWTL-UHFFFAOYSA-N 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 abstract description 15
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- 230000002195 synergetic effect Effects 0.000 abstract description 4
- 239000003112 inhibitor Substances 0.000 abstract description 3
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 239000013078 crystal Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 29
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000001914 filtration Methods 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- 150000003457 sulfones Chemical class 0.000 description 13
- 241000894006 Bacteria Species 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 239000007868 Raney catalyst Substances 0.000 description 8
- 229910000564 Raney nickel Inorganic materials 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 208000027531 mycobacterial infectious disease Diseases 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GDSADCTVCUIMDE-UHFFFAOYSA-N 5-[(2,4-diaminopyrimidin-5-yl)methyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1CC1=CN=C(N)N=C1N GDSADCTVCUIMDE-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- HWVSGNXPPWGZJQ-UHFFFAOYSA-N 3-anilino-2-[(4-decoxy-3-methoxyphenyl)methyl]prop-2-enenitrile Chemical compound C1=C(OC)C(OCCCCCCCCCC)=CC=C1CC(C#N)=CNC1=CC=CC=C1 HWVSGNXPPWGZJQ-UHFFFAOYSA-N 0.000 description 2
- DFLRQQOMLLBRKN-UHFFFAOYSA-N 4-decoxy-3-methoxybenzaldehyde Chemical compound CCCCCCCCCCOC1=CC=C(C=O)C=C1OC DFLRQQOMLLBRKN-UHFFFAOYSA-N 0.000 description 2
- VQVQZFHUXRSRBZ-UHFFFAOYSA-N 4-methoxy-3-phenylmethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 VQVQZFHUXRSRBZ-UHFFFAOYSA-N 0.000 description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 206010062207 Mycobacterial infection Diseases 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 2
- 208000031998 Mycobacterium Infections Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 108010022394 Threonine synthase Proteins 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 102000004419 dihydrofolate reductase Human genes 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229960000789 guanidine hydrochloride Drugs 0.000 description 2
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 2
- 229960000611 pyrimethamine Drugs 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 201000008827 tuberculosis Diseases 0.000 description 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- ATWLRNODAYAMQS-UHFFFAOYSA-N 1,1-dibromopropane Chemical compound CCC(Br)Br ATWLRNODAYAMQS-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- JBCUKQQIWSWEOK-UHFFFAOYSA-N 2-(benzenesulfonyl)aniline Chemical compound NC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 JBCUKQQIWSWEOK-UHFFFAOYSA-N 0.000 description 1
- HQTNNKBTJHHTNH-UHFFFAOYSA-N 2-[(4-decoxy-3-methoxyphenyl)methyl]-3-morpholin-4-ylprop-2-enenitrile Chemical compound C1=C(OC)C(OCCCCCCCCCC)=CC=C1CC(C#N)=CN1CCOCC1 HQTNNKBTJHHTNH-UHFFFAOYSA-N 0.000 description 1
- OOLOAWZLPBDRJQ-UHFFFAOYSA-N 2-benzylpyrimidine Chemical class N=1C=CC=NC=1CC1=CC=CC=C1 OOLOAWZLPBDRJQ-UHFFFAOYSA-N 0.000 description 1
- JSHLOPGSDZTEGQ-UHFFFAOYSA-N 3-methoxy-4-phenylmethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 JSHLOPGSDZTEGQ-UHFFFAOYSA-N 0.000 description 1
- GDYFDXDATVPPDR-UHFFFAOYSA-N 4-(benzenesulfonyl)aniline Chemical class C1=CC(N)=CC=C1S(=O)(=O)C1=CC=CC=C1 GDYFDXDATVPPDR-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
- RMLFIHMTVRNTMS-UHFFFAOYSA-N 4-[(2,4-diaminopyrimidin-5-yl)methyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 RMLFIHMTVRNTMS-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 241000588724 Escherichia coli Species 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
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241001147830 Mycobacterium lufu Species 0.000 description 1
- 241001646725 Mycobacterium tuberculosis H37Rv Species 0.000 description 1
- 108700035964 Mycobacterium tuberculosis HsaD Proteins 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 241000907661 Pieris rapae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 101000796021 Theileria parva Thioredoxin domain-containing protein Proteins 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical group 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 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
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- OZRNSSUDZOLUSN-LBPRGKRZSA-N dihydrofolic acid Chemical compound N=1C=2C(=O)NC(N)=NC=2NCC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OZRNSSUDZOLUSN-LBPRGKRZSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229960004198 guanidine Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- BBDNZMUIQBRBJH-UHFFFAOYSA-N sulfurochloridic acid;toluene Chemical compound OS(Cl)(=O)=O.CC1=CC=CC=C1 BBDNZMUIQBRBJH-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WSWJIZXMAUYHOE-UHFFFAOYSA-N tetroxoprim Chemical compound C1=C(OC)C(OCCOC)=C(OC)C=C1CC1=CN=C(N)N=C1N WSWJIZXMAUYHOE-UHFFFAOYSA-N 0.000 description 1
- 229960004809 tetroxoprim Drugs 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
-
- 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
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863603577 DE3603577A1 (de) | 1986-02-06 | 1986-02-06 | Neue substituierte 2,4-diamino-5-benzylpyrimidine, deren herstellung und deren verwendung als arzneimittel mit antibakterieller wirksamkeit |
| DE3603577.7 | 1986-02-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62265272A JPS62265272A (ja) | 1987-11-18 |
| JPH0826007B2 true JPH0826007B2 (ja) | 1996-03-13 |
Family
ID=6293457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62026178A Expired - Lifetime JPH0826007B2 (ja) | 1986-02-06 | 1987-02-06 | 新規置換２、４−ジアミノ−５−ベンジルピリミジン類、その製法およびそれを含有する抗菌剤 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4912112A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0231888B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPH0826007B2 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE84029T1 (cg-RX-API-DMAC7.html) |
| DE (2) | DE3603577A1 (cg-RX-API-DMAC7.html) |
| IN (1) | IN167562B (cg-RX-API-DMAC7.html) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3831445C2 (de) * | 1988-09-13 | 1998-09-10 | Joachim K Prof Dr Seydel | Verwendung von substituierten 2,4-Diamino-5-benzylpyrimidinen gegebenenfalls in Kombination mit 4,4'-Diaminodiphenylsulfonen zur Behandlung von Malaria |
| US5622954A (en) * | 1994-05-11 | 1997-04-22 | Fmc Corporation | 5[W(substituted aryl)alkenylene and alkynylene]-2,4-diaminopyrimidines as pesticides |
| US20030157036A1 (en) * | 2002-02-20 | 2003-08-21 | Osborne David W. | Topical dapsone for the treatment of acne |
| AU761544C (en) * | 1999-05-24 | 2004-02-12 | Sankyo Company Limited | Medicinal compositions containing anti-Fas antibody |
| RU2422441C2 (ru) | 2004-03-05 | 2011-06-27 | Ф.Хоффманн-Ля Рош Аг | Диаминопиримидины в качестве антагонистов рецепторов р2х3 |
| MXPA06011080A (es) | 2004-03-26 | 2007-04-16 | Astrazeneca Ab | Compuesto de 8-oxoadenina 9-sustituido. |
| EP1924565B1 (en) * | 2005-09-01 | 2016-09-14 | F.Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p3x2/3 modulators |
| EP1924566B1 (en) * | 2005-09-01 | 2016-01-13 | F.Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p2x2/3 modulators |
| ES2612890T3 (es) * | 2005-09-01 | 2017-05-19 | F. Hoffmann-La Roche Ag | Diaminopirimidinas como moduladores de P2X3 y P2X2/3 |
| JP2009526773A (ja) * | 2006-02-13 | 2009-07-23 | ラボラトワール セローノ ソシエテ アノニム | 細菌感染症治療のためのスルホンアミド誘導体 |
| JP2009542645A (ja) * | 2006-07-05 | 2009-12-03 | アストラゼネカ・アクチエボラーグ | Ｔｌｒ７のモジュレーターとして作用する８−オキソアデニン誘導体 |
| TW200831105A (en) * | 2006-12-14 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| DK2132209T3 (da) * | 2007-03-19 | 2014-04-14 | Astrazeneca Ab | 9-substituerede 8-oxo-adeninforbindelser som modulatorer af tlr7 (toll-like receptor 7) |
| JP5329444B2 (ja) * | 2007-03-19 | 2013-10-30 | アストラゼネカ・アクチエボラーグ | Ｔｏｌｌ様受容体（ｔｌｒ７）モジュレーターとしての９−置換−８−オキソ−アデニン化合物 |
| EP2138497A4 (en) * | 2007-03-20 | 2012-01-04 | Dainippon Sumitomo Pharma Co | NEW ADENINE CONNECTION |
| PE20091236A1 (es) * | 2007-11-22 | 2009-09-16 | Astrazeneca Ab | Derivados de pirimidina como immunomoduladores de tlr7 |
| UY31531A1 (es) | 2007-12-17 | 2009-08-03 | Sales derivadas de 8-oxoadenina composiciones farmacéuticas que las contienen y su uso en terapia como moduladores de receptor tipo toll (tlr) | |
| AU2008351422A1 (en) | 2008-02-27 | 2009-09-03 | Allergan, Inc. | Dapsone to treat rosascea |
| GB0908772D0 (en) * | 2009-05-21 | 2009-07-01 | Astrazeneca Ab | New salts 756 |
| JP5913093B2 (ja) | 2009-05-21 | 2016-04-27 | アストラゼネカ アクチボラグ | 新規ピリミジン誘導体と、癌とさらなる疾患の治療におけるそれらの使用 |
| JP5978225B2 (ja) | 2010-12-16 | 2016-08-24 | 大日本住友製薬株式会社 | 治療に有用なイミダゾ［４，５−ｃ］キノリン−１−イル誘導体 |
| DK2651943T3 (en) | 2010-12-17 | 2017-06-06 | Sumitomo Dainippon Pharma Co Ltd | purine derivatives |
| CN104302628B (zh) | 2012-05-18 | 2017-06-23 | 大日本住友制药株式会社 | 羧酸化合物 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB920412A (en) * | 1958-04-18 | 1963-03-06 | Wellcome Found | Pyrimidine derivatives and the manufacture thereof |
| DE1303727B (de) * | 1959-09-03 | 1976-02-05 | Ausscheidung aus: 14 45 176 The Wellcome Foundation Ltd., London | Alpha-Arylidensubstituierte Propioni-Irile |
| DE1720031A1 (de) * | 1966-02-19 | 1972-08-03 | Wellcome Found | Biologisch wirksame 5-Benzylpyrimidin-Derivate und Verfahren zu ihrer Herstellung |
| GB1261455A (en) * | 1969-03-06 | 1972-01-26 | Burroughs Wellcome Co | Improvements in or relating to substituted acrylonitriles |
| US4143227A (en) * | 1973-02-26 | 1979-03-06 | Hoffmann-La Roche Inc. | Process for substituted 5-benzyl-2,4-diamino-pyrimidines |
| 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 |
| US4115650A (en) * | 1976-11-17 | 1978-09-19 | Hoffmann-La Roche Inc. | Process for preparing 2,4-diamino-5-(substituted benzyl)-pyrimidines |
| 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 |
| GR71725B (cg-RX-API-DMAC7.html) * | 1977-11-10 | 1983-06-22 | Hoffmann La Roche | |
| US4258045A (en) * | 1979-11-30 | 1981-03-24 | Merck & Co., Inc. | Inhibitor of dihydrofolate reductase |
| JPS57116050A (en) * | 1980-11-27 | 1982-07-19 | Wellcome Found | 2,4-diamino-5-benzylpyrimidine |
-
1986
- 1986-02-06 DE DE19863603577 patent/DE3603577A1/de not_active Ceased
-
1987
- 1987-01-29 DE DE8787101246T patent/DE3783238D1/de not_active Expired - Fee Related
- 1987-01-29 AT AT87101246T patent/ATE84029T1/de not_active IP Right Cessation
- 1987-01-29 EP EP87101246A patent/EP0231888B1/de not_active Expired - Lifetime
- 1987-02-06 US US07/011,957 patent/US4912112A/en not_active Expired - Fee Related
- 1987-02-06 JP JP62026178A patent/JPH0826007B2/ja not_active Expired - Lifetime
- 1987-07-21 IN IN560/CAL/87A patent/IN167562B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0231888A3 (en) | 1988-10-19 |
| EP0231888B1 (de) | 1992-12-30 |
| IN167562B (cg-RX-API-DMAC7.html) | 1990-11-17 |
| DE3783238D1 (de) | 1993-02-11 |
| DE3603577A1 (de) | 1987-08-13 |
| ATE84029T1 (de) | 1993-01-15 |
| JPS62265272A (ja) | 1987-11-18 |
| EP0231888A2 (de) | 1987-08-12 |
| US4912112A (en) | 1990-03-27 |
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