NO782340L - Fremgangsmaate for fremstilling av farmakologisk aktive benzylpyrimidiner - Google Patents
Fremgangsmaate for fremstilling av farmakologisk aktive benzylpyrimidinerInfo
- Publication number
- NO782340L NO782340L NO782340A NO782340A NO782340L NO 782340 L NO782340 L NO 782340L NO 782340 A NO782340 A NO 782340A NO 782340 A NO782340 A NO 782340A NO 782340 L NO782340 L NO 782340L
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- compound
- pyrimidine
- trimethoxybenzyl
- atoms
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- -1 cyclic amine Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- OOLOAWZLPBDRJQ-UHFFFAOYSA-N 2-benzylpyrimidine Chemical class N=1C=CC=NC=1CC1=CC=CC=C1 OOLOAWZLPBDRJQ-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 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 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229960001082 trimethoprim Drugs 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000003456 sulfonamides Chemical class 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229940124530 sulfonamide Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IFLXPFPDRCASRC-UHFFFAOYSA-N 2-n-(cyclohexyloxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CC=2C(=NC(NCOC3CCCCC3)=NC=2)N)=C1 IFLXPFPDRCASRC-UHFFFAOYSA-N 0.000 description 2
- IMPUXVGXZZPILE-UHFFFAOYSA-N 2-n-(methoxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.NC1=NC(NCOC)=NC=C1CC1=CC(OC)=C(OC)C(OC)=C1 IMPUXVGXZZPILE-UHFFFAOYSA-N 0.000 description 2
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000193985 Streptococcus agalactiae Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- GYCLGFVWNVHUPA-UHFFFAOYSA-N chloromethoxycyclohexane Chemical compound ClCOC1CCCCC1 GYCLGFVWNVHUPA-UHFFFAOYSA-N 0.000 description 2
- LADPCMZCENPFGV-UHFFFAOYSA-N chloromethoxymethylbenzene Chemical compound ClCOCC1=CC=CC=C1 LADPCMZCENPFGV-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NEFNOUUWYACOKP-UHFFFAOYSA-N 1-(chloromethoxy)butane Chemical compound CCCCOCCl NEFNOUUWYACOKP-UHFFFAOYSA-N 0.000 description 1
- AGDIDCDJVCRQCJ-UHFFFAOYSA-N 1-(chloromethoxy)hexane Chemical compound CCCCCCOCCl AGDIDCDJVCRQCJ-UHFFFAOYSA-N 0.000 description 1
- VHUQXPJHMISKGS-UHFFFAOYSA-N 1-(chloromethoxy)propane Chemical compound CCCOCCl VHUQXPJHMISKGS-UHFFFAOYSA-N 0.000 description 1
- QTCKZDZOQXBHHH-UHFFFAOYSA-N 1-chloro-2-(chloromethoxy)propane Chemical compound ClCC(C)OCCl QTCKZDZOQXBHHH-UHFFFAOYSA-N 0.000 description 1
- JXXQSFUWEIFWJY-UHFFFAOYSA-N 2-(2-hydroxyethyl)guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NCCO JXXQSFUWEIFWJY-UHFFFAOYSA-N 0.000 description 1
- DITIPOXEWUGULB-UHFFFAOYSA-N 2-(2-phenylethyl)guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NCCC1=CC=CC=C1 DITIPOXEWUGULB-UHFFFAOYSA-N 0.000 description 1
- FQYRFGGSTJTBEJ-UHFFFAOYSA-N 2-(2-pyrrolidin-1-ylethyl)guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NCCN1CCCC1 FQYRFGGSTJTBEJ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- GBPWFXAWLHBOCQ-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NCC1=CC=C(Cl)C=C1 GBPWFXAWLHBOCQ-UHFFFAOYSA-N 0.000 description 1
- KBBNFTOXDUKKGX-UHFFFAOYSA-N 2-amino-n-(4,5-dimethyl-1,3-oxazol-2-yl)benzenesulfonamide Chemical compound O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=CC=C1N KBBNFTOXDUKKGX-UHFFFAOYSA-N 0.000 description 1
- SQYPEJLKAOZVHW-UHFFFAOYSA-N 2-benzylguanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NCC1=CC=CC=C1.NC(N)=NCC1=CC=CC=C1 SQYPEJLKAOZVHW-UHFFFAOYSA-N 0.000 description 1
- WZBYDPPOLTUYSM-UHFFFAOYSA-N 2-n-(1-chloropropan-2-yloxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CC=2C(=NC(NCOC(C)CCl)=NC=2)N)=C1 WZBYDPPOLTUYSM-UHFFFAOYSA-N 0.000 description 1
- XNJYJCJFZWEAFJ-UHFFFAOYSA-N 2-n-(butoxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.NC1=NC(NCOCCCC)=NC=C1CC1=CC(OC)=C(OC)C(OC)=C1 XNJYJCJFZWEAFJ-UHFFFAOYSA-N 0.000 description 1
- LLJUOMZFSBAYIW-UHFFFAOYSA-N 2-n-(cyclohexyloxymethyl)-5-[(4-methoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(C(=N1)N)=CN=C1NCOC1CCCCC1 LLJUOMZFSBAYIW-UHFFFAOYSA-N 0.000 description 1
- XQMFKIMZKRKCSF-UHFFFAOYSA-N 2-n-(hexoxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.NC1=NC(NCOCCCCCC)=NC=C1CC1=CC(OC)=C(OC)C(OC)=C1 XQMFKIMZKRKCSF-UHFFFAOYSA-N 0.000 description 1
- PJYHEIWNIDKXOQ-UHFFFAOYSA-N 2-n-(phenylmethoxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CC=2C(=NC(NCOCC=3C=CC=CC=3)=NC=2)N)=C1 PJYHEIWNIDKXOQ-UHFFFAOYSA-N 0.000 description 1
- FKKKHYTUOJMSRF-UHFFFAOYSA-N 2-n-(propoxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.NC1=NC(NCOCCC)=NC=C1CC1=CC(OC)=C(OC)C(OC)=C1 FKKKHYTUOJMSRF-UHFFFAOYSA-N 0.000 description 1
- ATOMBSOAMRAQHY-UHFFFAOYSA-N 2-n-[(4-chlorophenyl)methyl]-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(NCC=3C=CC(Cl)=CC=3)=NC=2)N)=C1 ATOMBSOAMRAQHY-UHFFFAOYSA-N 0.000 description 1
- QGINLKLHYGYAFA-UHFFFAOYSA-N 2-n-benzyl-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(NCC=3C=CC=CC=3)=NC=2)N)=C1 QGINLKLHYGYAFA-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- WUEZQZHHXYEAQM-UHFFFAOYSA-N 2-prop-2-enylguanidine Chemical compound NC(N)=NCC=C WUEZQZHHXYEAQM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- LINYIIJIYSUIET-UHFFFAOYSA-N 3-tert-butyl-5-(chloromethyl)-1,2-oxazole Chemical compound CC(C)(C)C=1C=C(CCl)ON=1 LINYIIJIYSUIET-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- XIKYUFRCSIWOSF-UHFFFAOYSA-N 5-(chloromethyl)-3-ethyl-1,2-oxazole Chemical compound CCC=1C=C(CCl)ON=1 XIKYUFRCSIWOSF-UHFFFAOYSA-N 0.000 description 1
- ZWBJJNWJUXXFNP-UHFFFAOYSA-N 5-(chloromethyl)-3-methyl-1,2-oxazole Chemical compound CC=1C=C(CCl)ON=1 ZWBJJNWJUXXFNP-UHFFFAOYSA-N 0.000 description 1
- DXCHZEISFLMPFZ-UHFFFAOYSA-N 5-(chloromethyl)-3-propan-2-yl-1,2-oxazole Chemical compound CC(C)C=1C=C(CCl)ON=1 DXCHZEISFLMPFZ-UHFFFAOYSA-N 0.000 description 1
- SAIIUKTXZZMVHR-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CC1=CC=CC=C1Cl SAIIUKTXZZMVHR-UHFFFAOYSA-N 0.000 description 1
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- KNMBSJCWXZMBIJ-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CC1=CC=C(Cl)C=C1 KNMBSJCWXZMBIJ-UHFFFAOYSA-N 0.000 description 1
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- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
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- 125000003118 aryl group Chemical group 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
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 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
- KXRZBTAEDBELFD-UHFFFAOYSA-N sulfamethopyrazine Chemical compound COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 KXRZBTAEDBELFD-UHFFFAOYSA-N 0.000 description 1
- GPTONYMQFTZPKC-UHFFFAOYSA-N sulfamethoxydiazine Chemical compound N1=CC(OC)=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 GPTONYMQFTZPKC-UHFFFAOYSA-N 0.000 description 1
- VLYWMPOKSSWJAL-UHFFFAOYSA-N sulfamethoxypyridazine Chemical compound N1=NC(OC)=CC=C1NS(=O)(=O)C1=CC=C(N)C=C1 VLYWMPOKSSWJAL-UHFFFAOYSA-N 0.000 description 1
- YZMCKZRAOLZXAZ-UHFFFAOYSA-N sulfisomidine Chemical compound CC1=NC(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 YZMCKZRAOLZXAZ-UHFFFAOYSA-N 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
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000001635 urinary tract Anatomy 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772730467 DE2730467A1 (de) | 1977-07-06 | 1977-07-06 | Benzylpyrimidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO782340L true NO782340L (no) | 1979-01-09 |
Family
ID=6013252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO782340A NO782340L (no) | 1977-07-06 | 1978-07-05 | Fremgangsmaate for fremstilling av farmakologisk aktive benzylpyrimidiner |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4279899A (it) |
| EP (1) | EP0000334B1 (it) |
| JP (1) | JPS5416482A (it) |
| AR (1) | AR223465A1 (it) |
| AT (1) | AT361931B (it) |
| AU (1) | AU515661B2 (it) |
| CA (1) | CA1102324A (it) |
| DE (2) | DE2730467A1 (it) |
| DK (1) | DK142578C (it) |
| FI (1) | FI782173A (it) |
| HU (1) | HU179407B (it) |
| IE (1) | IE781308L (it) |
| IL (1) | IL55018A (it) |
| IN (1) | IN149577B (it) |
| IT (1) | IT7825220A0 (it) |
| NO (1) | NO782340L (it) |
| ZA (1) | ZA783873B (it) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4438267A (en) * | 1980-11-11 | 1984-03-20 | Daluge Susan M | Monoheteroring compounds and their use |
| DE3045720A1 (de) * | 1980-12-04 | 1982-07-08 | Basf Ag, 6700 Ludwigshafen | N-pyrimidinyl-carbaminsaeureester, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| HU186413B (en) * | 1981-06-26 | 1985-07-29 | Egyt Gyogyszervegyeszeti Gyar | Process for producing 2,4-diamino-5-bracket-3-comma above,4-comma above,5-comma above-trimethoxy-benzyl-bracket closed-pyrimidine |
| HU187370B (en) * | 1981-06-26 | 1985-12-28 | Egyt Gyogyszervegyeszeti Gyar | Improved process for producing 2,4-diamino-5-bracket-3-comma above, 4-comma above,5-comma above-trimethoxy-benzyl-bracket closed-pyrimidine |
| CA2463989C (en) * | 2001-10-17 | 2012-01-31 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pyrimidine derivatives, pharmaceutical compositions containing these compounds, the use thereof and process for the preparation thereof |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| WO2011133920A1 (en) | 2010-04-23 | 2011-10-27 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3049544A (en) * | 1962-08-14 | Method for the preparation of | ||
| US2723975A (en) * | 1952-04-03 | 1955-11-15 | Nepera Chemical Co Inc | 2, 4-di-piperidino-5-benzylpyrimidine |
| US2649449A (en) * | 1952-04-04 | 1953-08-18 | Nepera Chemical Co Inc | 2-cyclohexylamino-4-amino-5-benzylpyrimidine |
| CH376115A (de) * | 1957-12-06 | 1964-03-31 | Ciba Geigy | Verfahren zur Herstellung neuer substituierter Pyrimidine |
| US3515783A (en) | 1967-10-20 | 1970-06-02 | Hoffmann La Roche | Antibacterial composition containing 5-methyl - 3 - sulfanilamidoisoxazole and trimethoxybenzyl pyrimidine |
| US4115650A (en) * | 1976-11-17 | 1978-09-19 | Hoffmann-La Roche Inc. | Process for preparing 2,4-diamino-5-(substituted benzyl)-pyrimidines |
-
1977
- 1977-07-06 DE DE19772730467 patent/DE2730467A1/de not_active Withdrawn
-
1978
- 1978-06-16 EP EP78100180A patent/EP0000334B1/de not_active Expired
- 1978-06-16 DE DE7878100180T patent/DE2860928D1/de not_active Expired
- 1978-06-27 US US05/919,505 patent/US4279899A/en not_active Expired - Lifetime
- 1978-06-27 IL IL55018A patent/IL55018A/xx unknown
- 1978-06-29 IE IE781308A patent/IE781308L/xx unknown
- 1978-06-30 IT IT7825220A patent/IT7825220A0/it unknown
- 1978-06-30 AU AU37644/78A patent/AU515661B2/en not_active Expired
- 1978-07-04 HU HU78BA3672A patent/HU179407B/hu unknown
- 1978-07-04 AR AR272831A patent/AR223465A1/es active
- 1978-07-04 CA CA306,732A patent/CA1102324A/en not_active Expired
- 1978-07-05 NO NO782340A patent/NO782340L/no unknown
- 1978-07-05 AT AT487478A patent/AT361931B/de not_active IP Right Cessation
- 1978-07-05 DK DK303178A patent/DK142578C/da active
- 1978-07-05 ZA ZA00783873A patent/ZA783873B/xx unknown
- 1978-07-05 FI FI782173A patent/FI782173A/fi not_active Application Discontinuation
- 1978-07-06 IN IN747/CAL/78A patent/IN149577B/en unknown
- 1978-07-06 JP JP8153078A patent/JPS5416482A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2860928D1 (en) | 1981-11-12 |
| AU515661B2 (en) | 1981-04-16 |
| IN149577B (it) | 1982-01-30 |
| ATA487478A (de) | 1980-09-15 |
| EP0000334B1 (de) | 1981-08-12 |
| DE2730467A1 (de) | 1979-01-18 |
| EP0000334A1 (de) | 1979-01-24 |
| IL55018A0 (en) | 1978-08-31 |
| AU3764478A (en) | 1980-01-03 |
| DK142578C (da) | 1981-07-20 |
| FI782173A (fi) | 1979-01-07 |
| HU179407B (en) | 1982-10-28 |
| AR223465A1 (es) | 1981-08-31 |
| IT7825220A0 (it) | 1978-06-30 |
| JPS5416482A (en) | 1979-02-07 |
| DK142578B (da) | 1980-11-24 |
| ZA783873B (en) | 1979-08-29 |
| IL55018A (en) | 1983-03-31 |
| IE781308L (en) | 1979-01-06 |
| AT361931B (de) | 1981-04-10 |
| DK303178A (da) | 1979-01-07 |
| CA1102324A (en) | 1981-06-02 |
| US4279899A (en) | 1981-07-21 |
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