DE2558150A1 - Neue benzylpyrimidine - Google Patents
Neue benzylpyrimidineInfo
- Publication number
- DE2558150A1 DE2558150A1 DE19752558150 DE2558150A DE2558150A1 DE 2558150 A1 DE2558150 A1 DE 2558150A1 DE 19752558150 DE19752558150 DE 19752558150 DE 2558150 A DE2558150 A DE 2558150A DE 2558150 A1 DE2558150 A1 DE 2558150A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- diamino
- dimethylamino
- amino
- ethyl acetate
- 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.)
- Ceased
Links
- OOLOAWZLPBDRJQ-UHFFFAOYSA-N 2-benzylpyrimidine Chemical compound N=1C=CC=NC=1CC1=CC=CC=C1 OOLOAWZLPBDRJQ-UHFFFAOYSA-N 0.000 title description 2
- -1 pyrrolidino, piperidino Chemical group 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 32
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- 230000000844 anti-bacterial effect Effects 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000007983 Tris buffer Substances 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- QIWUOESCZSCFBO-UHFFFAOYSA-N 5-[[3,5-bis(dimethylamino)-4-piperidin-1-ylphenyl]methyl]pyrimidine-2,4-diamine Chemical compound C=1C(N(C)C)=C(N2CCCCC2)C(N(C)C)=CC=1CC1=CN=C(N)N=C1N QIWUOESCZSCFBO-UHFFFAOYSA-N 0.000 claims 1
- AJKCFKGHEBKPNA-UHFFFAOYSA-N 5-[[3-(dimethylamino)-4-methoxy-5-(methylamino)phenyl]methyl]pyrimidine-2,4-diamine Chemical compound CN(C)C1=C(OC)C(NC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 AJKCFKGHEBKPNA-UHFFFAOYSA-N 0.000 claims 1
- DSXVTRAXEHWUPT-UHFFFAOYSA-N 5-[[4-chloro-3-(dimethylamino)-5-(methylamino)phenyl]methyl]pyrimidine-2,4-diamine Chemical compound CN(C)C1=C(Cl)C(NC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 DSXVTRAXEHWUPT-UHFFFAOYSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 261
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 227
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 97
- 239000000243 solution Substances 0.000 description 91
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 65
- 239000000203 mixture Substances 0.000 description 62
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 239000000725 suspension Substances 0.000 description 40
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 35
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 34
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
- 238000001953 recrystallisation Methods 0.000 description 25
- 229910052938 sodium sulfate Inorganic materials 0.000 description 25
- 235000011152 sodium sulphate Nutrition 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 230000007717 exclusion Effects 0.000 description 24
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 20
- 239000003208 petroleum Substances 0.000 description 20
- 239000012312 sodium hydride Substances 0.000 description 20
- 229910000104 sodium hydride Inorganic materials 0.000 description 20
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 18
- 239000011734 sodium Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 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 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- 229910052708 sodium Inorganic materials 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000012279 sodium borohydride Substances 0.000 description 16
- 229910000033 sodium borohydride Inorganic materials 0.000 description 16
- 239000007858 starting material Substances 0.000 description 15
- FENJKTQEFUPECW-UHFFFAOYSA-N 3-anilinopropanenitrile Chemical compound N#CCCNC1=CC=CC=C1 FENJKTQEFUPECW-UHFFFAOYSA-N 0.000 description 13
- 235000019445 benzyl alcohol Nutrition 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 13
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000005457 ice water Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 7
- 229960000789 guanidine hydrochloride Drugs 0.000 description 7
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 7
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 5
- 229960004198 guanidine Drugs 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229960001413 acetanilide Drugs 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000002024 ethyl acetate extract Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 4
- 229940095102 methyl benzoate Drugs 0.000 description 4
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229960005404 sulfamethoxazole Drugs 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 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 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- IBTBJYDTJYIERA-UHFFFAOYSA-N 2-(dimethylamino)-3-phenylpropanenitrile Chemical compound CN(C)C(C#N)CC1=CC=CC=C1 IBTBJYDTJYIERA-UHFFFAOYSA-N 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000003118 aryl 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
- 239000000839 emulsion Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
- CJARNLGTJZCIMJ-UHFFFAOYSA-N methyl 3,5-bis(dimethylamino)-4-piperidin-1-ylbenzoate Chemical compound CN(C)C1=CC(C(=O)OC)=CC(N(C)C)=C1N1CCCCC1 CJARNLGTJZCIMJ-UHFFFAOYSA-N 0.000 description 3
- FAIUQQCVIWGFGU-UHFFFAOYSA-N methyl 3,5-diamino-4-methylbenzoate Chemical compound COC(=O)C1=CC(N)=C(C)C(N)=C1 FAIUQQCVIWGFGU-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UAFZGBAUKCGUBP-UHFFFAOYSA-N 1-[3,5-bis(dimethylamino)-4-piperidin-1-ylphenyl]-2-methylsulfonylethanone Chemical compound CN(C)C1=CC(C(=O)CS(C)(=O)=O)=CC(N(C)C)=C1N1CCCCC1 UAFZGBAUKCGUBP-UHFFFAOYSA-N 0.000 description 2
- BKYHVSHGVBJKPC-UHFFFAOYSA-N 1-[3,5-bis(methylamino)phenyl]-2-methylsulfonylethanone Chemical compound CNC1=CC(NC)=CC(C(=O)CS(C)(=O)=O)=C1 BKYHVSHGVBJKPC-UHFFFAOYSA-N 0.000 description 2
- FFSILGLQWWOXRT-UHFFFAOYSA-N 1-[4-methoxy-3,5-di(pyrrol-1-yl)phenyl]-2-methylsulfonylethanone Chemical compound COC1=C(N2C=CC=C2)C=C(C(=O)CS(C)(=O)=O)C=C1N1C=CC=C1 FFSILGLQWWOXRT-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- XLDSBPYWVLEDFW-UHFFFAOYSA-N 2-(dimethylamino)-N-methyl-N-phenylacetamide Chemical compound CN(C)CC(=O)N(C)C1=CC=CC=C1 XLDSBPYWVLEDFW-UHFFFAOYSA-N 0.000 description 2
- FHHUBIZJWDOPCO-UHFFFAOYSA-N 3-anilino-2-[[3,5-bis(2,5-dimethylpyrrol-1-yl)-4-methylphenyl]methyl]prop-2-enenitrile Chemical compound CC1=CC=C(C)N1C1=CC(CC(=CNC=2C=CC=CC=2)C#N)=CC(N2C(=CC=C2C)C)=C1C FHHUBIZJWDOPCO-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- ACRWYXSKEHUQDB-UHFFFAOYSA-N 3-phenylpropionitrile Chemical compound N#CCCC1=CC=CC=C1 ACRWYXSKEHUQDB-UHFFFAOYSA-N 0.000 description 2
- QCESOQYTNNRNNY-UHFFFAOYSA-N 4-bromo-3,5-difluorobenzenesulfonyl chloride Chemical compound FC1=CC(S(Cl)(=O)=O)=CC(F)=C1Br QCESOQYTNNRNNY-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QVSNGZALKWQQGT-UHFFFAOYSA-N methyl 3,4,5-tris(dimethylamino)benzoate Chemical compound COC(=O)C1=CC(N(C)C)=C(N(C)C)C(N(C)C)=C1 QVSNGZALKWQQGT-UHFFFAOYSA-N 0.000 description 2
- NAOZURCTVHQPDK-UHFFFAOYSA-N methyl 3,5-bis(dimethylamino)benzoate Chemical compound COC(=O)C1=CC(N(C)C)=CC(N(C)C)=C1 NAOZURCTVHQPDK-UHFFFAOYSA-N 0.000 description 2
- PWRWTKQJWBIYIH-UHFFFAOYSA-N methyl 3,5-diacetamido-4-chlorobenzoate Chemical compound COC(=O)C1=CC(NC(C)=O)=C(Cl)C(NC(C)=O)=C1 PWRWTKQJWBIYIH-UHFFFAOYSA-N 0.000 description 2
- YLBOVRLASJERMP-UHFFFAOYSA-N methyl 3,5-diamino-4-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC(N)=C(N(C)C)C(N)=C1 YLBOVRLASJERMP-UHFFFAOYSA-N 0.000 description 2
- QSBFYMBFQLOZNZ-UHFFFAOYSA-N methyl 3,5-diamino-4-chlorobenzoate Chemical compound COC(=O)C1=CC(N)=C(Cl)C(N)=C1 QSBFYMBFQLOZNZ-UHFFFAOYSA-N 0.000 description 2
- LQGFFNOFLTYVNL-UHFFFAOYSA-N methyl 3-amino-4-methyl-5-pyrrol-1-ylbenzoate Chemical compound COC(=O)C1=CC(N)=C(C)C(N2C=CC=C2)=C1 LQGFFNOFLTYVNL-UHFFFAOYSA-N 0.000 description 2
- PMLOUIISQNSQGU-UHFFFAOYSA-N methyl 4-[acetyl(methyl)amino]-3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=C(N(C)C(C)=O)C([N+]([O-])=O)=C1 PMLOUIISQNSQGU-UHFFFAOYSA-N 0.000 description 2
- VPPPGGOGBHVDEP-UHFFFAOYSA-N methyl 4-tert-butyl-3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=C(C(C)(C)C)C([N+]([O-])=O)=C1 VPPPGGOGBHVDEP-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000005544 phthalimido group Chemical group 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- IXLDIJPRDDUUKL-UHFFFAOYSA-N (dimethylamino)methyl benzoate Chemical compound CN(C)COC(=O)C1=CC=CC=C1 IXLDIJPRDDUUKL-UHFFFAOYSA-N 0.000 description 1
- ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RCLCKDYMKSKHHN-UHFFFAOYSA-N 1-[3,5-bis(dimethylamino)phenyl]-2-methylsulfonylethanone Chemical compound CN(C)C1=CC(N(C)C)=CC(C(=O)CS(C)(=O)=O)=C1 RCLCKDYMKSKHHN-UHFFFAOYSA-N 0.000 description 1
- MSDDDRFCERQEIC-UHFFFAOYSA-N 1-[4-chloro-3,5-bis(dimethylamino)phenyl]-2-methylsulfonylethanone Chemical compound CN(C)C1=CC(C(=O)CS(C)(=O)=O)=CC(N(C)C)=C1Cl MSDDDRFCERQEIC-UHFFFAOYSA-N 0.000 description 1
- LSGSMQRRKFZJIQ-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxysulfanyloxy)ethane Chemical group COCCOSOCCOC LSGSMQRRKFZJIQ-UHFFFAOYSA-N 0.000 description 1
- UHPDGGAYPGKHSG-UHFFFAOYSA-N 1-phenyl-5-(1-phenyltetrazol-5-yl)oxytetrazole Chemical compound N=1N=NN(C=2C=CC=CC=2)C=1OC1=NN=NN1C1=CC=CC=C1 UHPDGGAYPGKHSG-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- HRKTYSDVSRVOIP-UHFFFAOYSA-N 2,2-diethoxyoxolane Chemical compound CCOC1(OCC)CCCO1 HRKTYSDVSRVOIP-UHFFFAOYSA-N 0.000 description 1
- LNNXJVNZEMGISN-UHFFFAOYSA-N 2-(dimethylamino)-2-methylsulfonyl-1-phenylethanone Chemical compound CN(C)C(C(=O)C1=CC=CC=C1)S(=O)(=O)C LNNXJVNZEMGISN-UHFFFAOYSA-N 0.000 description 1
- BSRMGBSGMZCRCH-UHFFFAOYSA-N 2-(methylamino)-2-methylsulfonyl-1-phenylethanone Chemical compound CNC(C(=O)C1=CC=CC=C1)S(=O)(=O)C BSRMGBSGMZCRCH-UHFFFAOYSA-N 0.000 description 1
- AMFSJVJTVJYFBE-UHFFFAOYSA-N 2-amino-n-(4,5-dimethyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound CC1=C(C)ON=C1NS(=O)(=O)C1=CC=CC=C1N AMFSJVJTVJYFBE-UHFFFAOYSA-N 0.000 description 1
- AZVRQGHQVPBIHL-UHFFFAOYSA-N 2-amino-n-(4,5-dimethylpyrimidin-2-yl)benzenesulfonamide Chemical compound N1=C(C)C(C)=CN=C1NS(=O)(=O)C1=CC=CC=C1N AZVRQGHQVPBIHL-UHFFFAOYSA-N 0.000 description 1
- WIISOYLZJJYTHT-UHFFFAOYSA-N 2-methyl-1h-pyrazol-5-one Chemical compound CN1C=CC(O)=N1 WIISOYLZJJYTHT-UHFFFAOYSA-N 0.000 description 1
- CAUSPZIZBLGLKW-UHFFFAOYSA-N 2-methylsulfonyl-1-phenylethanone Chemical compound CS(=O)(=O)CC(=O)C1=CC=CC=C1 CAUSPZIZBLGLKW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BPEXTIMJLDWDTL-UHFFFAOYSA-N 2`-Methylacetanilide Chemical compound CC(=O)NC1=CC=CC=C1C BPEXTIMJLDWDTL-UHFFFAOYSA-N 0.000 description 1
- MZIMVVYXDAVEJV-UHFFFAOYSA-N 3,5-bis(dimethylamino)-4-piperidin-1-ylbenzaldehyde Chemical compound CN(C)C1=CC(C=O)=CC(N(C)C)=C1N1CCCCC1 MZIMVVYXDAVEJV-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- HVSLFUCYGNHPFB-UHFFFAOYSA-N 3-anilino-2-[[3,5-bis(dimethylamino)-4-methoxyphenyl]methyl]prop-2-enenitrile Chemical compound C1=C(N(C)C)C(OC)=C(N(C)C)C=C1CC(C#N)=CNC1=CC=CC=C1 HVSLFUCYGNHPFB-UHFFFAOYSA-N 0.000 description 1
- YAHHWOADINWBAY-UHFFFAOYSA-N 3-anilino-2-[[4-chloro-3,5-bis(dimethylamino)phenyl]methyl]prop-2-enenitrile Chemical compound CN(C)C1=C(Cl)C(N(C)C)=CC(CC(=CNC=2C=CC=CC=2)C#N)=C1 YAHHWOADINWBAY-UHFFFAOYSA-N 0.000 description 1
- AHOQULIUJXTSBJ-UHFFFAOYSA-N 3-anilino-2-[[4-chloro-3,5-bis(methylamino)phenyl]methyl]prop-2-enenitrile Chemical compound CNC1=C(Cl)C(NC)=CC(CC(=CNC=2C=CC=CC=2)C#N)=C1 AHOQULIUJXTSBJ-UHFFFAOYSA-N 0.000 description 1
- WCAUHQWNRVVGHX-UHFFFAOYSA-N 3-anilino-2-[[4-tert-butyl-3,5-bis(dimethylamino)phenyl]methyl]prop-2-enenitrile Chemical compound CN(C)C1=C(C(C)(C)C)C(N(C)C)=CC(CC(=CNC=2C=CC=CC=2)C#N)=C1 WCAUHQWNRVVGHX-UHFFFAOYSA-N 0.000 description 1
- OOWFYDWAMOKVSF-UHFFFAOYSA-N 3-methoxypropanenitrile Chemical compound COCCC#N OOWFYDWAMOKVSF-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WHTXLZQPQJAELS-UHFFFAOYSA-N 4-tert-butyl-3,5-dinitrobenzoic acid Chemical compound CC(C)(C)C1=C([N+]([O-])=O)C=C(C(O)=O)C=C1[N+]([O-])=O WHTXLZQPQJAELS-UHFFFAOYSA-N 0.000 description 1
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
- MXJXZKOMLWDBLT-UHFFFAOYSA-N 5-[[3,5-bis(methylamino)phenyl]methyl]pyrimidine-2,4-diamine Chemical compound CNC1=CC(NC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 MXJXZKOMLWDBLT-UHFFFAOYSA-N 0.000 description 1
- DHELIGKVOGTMGF-UHFFFAOYSA-N 5-chloro-1-phenyltetrazole Chemical compound ClC1=NN=NN1C1=CC=CC=C1 DHELIGKVOGTMGF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UYQKZKVNYKOXHG-UHFFFAOYSA-N Methyl n-acetylanthranilate Chemical compound COC(=O)C1=CC=CC=C1NC(C)=O UYQKZKVNYKOXHG-UHFFFAOYSA-N 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- WMPXPUYPYQKQCX-UHFFFAOYSA-N Sulfamonomethoxine Chemical compound C1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 WMPXPUYPYQKQCX-UHFFFAOYSA-N 0.000 description 1
- NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 108010022394 Threonine synthase Proteins 0.000 description 1
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
- UAJGYNKUMWOQFQ-UHFFFAOYSA-N dichloromethane;propan-1-ol Chemical compound ClCCl.CCCO UAJGYNKUMWOQFQ-UHFFFAOYSA-N 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 102000004419 dihydrofolate reductase Human genes 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- HYWFMEWWJLKYSI-UHFFFAOYSA-N methyl 2,6-diamino-4-methylbenzoate Chemical compound COC(=O)C1=C(N)C=C(C)C=C1N HYWFMEWWJLKYSI-UHFFFAOYSA-N 0.000 description 1
- FBUKJSFCGYGCCX-UHFFFAOYSA-N methyl 2-[acetyl(methyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1N(C)C(C)=O FBUKJSFCGYGCCX-UHFFFAOYSA-N 0.000 description 1
- ZCNSBHAIPOWHJE-UHFFFAOYSA-N methyl 2-dimethylaminobenzoate Chemical compound COC(=O)C1=CC=CC=C1N(C)C ZCNSBHAIPOWHJE-UHFFFAOYSA-N 0.000 description 1
- NEPXWBJCNFCVLZ-UHFFFAOYSA-N methyl 3,5-bis[acetyl(methyl)amino]-4-chlorobenzoate Chemical compound COC(=O)C1=CC(N(C)C(C)=O)=C(Cl)C(N(C)C(C)=O)=C1 NEPXWBJCNFCVLZ-UHFFFAOYSA-N 0.000 description 1
- UHMFMJFUFFYEPF-UHFFFAOYSA-N methyl 3-acetamido-4-methyl-5-pyrrol-1-ylbenzoate Chemical compound COC(=O)C1=CC(NC(C)=O)=C(C)C(N2C=CC=C2)=C1 UHMFMJFUFFYEPF-UHFFFAOYSA-N 0.000 description 1
- ZJJPSYCLPBWKBW-UHFFFAOYSA-N methyl 3-acetamido-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(NC(C)=O)=C1 ZJJPSYCLPBWKBW-UHFFFAOYSA-N 0.000 description 1
- HTTNLIJYLRDKQV-UHFFFAOYSA-N methyl 4-(methylamino)-3,5-dinitrobenzoate Chemical compound CNC1=C([N+]([O-])=O)C=C(C(=O)OC)C=C1[N+]([O-])=O HTTNLIJYLRDKQV-UHFFFAOYSA-N 0.000 description 1
- YYAYVAMYQDVCCN-UHFFFAOYSA-N methyl 4-[acetyl(methyl)amino]-3,5-bis(dimethylamino)benzoate Chemical compound COC(=O)C1=CC(N(C)C)=C(N(C)C(C)=O)C(N(C)C)=C1 YYAYVAMYQDVCCN-UHFFFAOYSA-N 0.000 description 1
- TWTBTSWOUNUQGA-UHFFFAOYSA-N methyl 4-[acetyl(methyl)amino]-3,5-diaminobenzoate Chemical compound COC(=O)C1=CC(N)=C(N(C)C(C)=O)C(N)=C1 TWTBTSWOUNUQGA-UHFFFAOYSA-N 0.000 description 1
- UYVHJAFBTJMJMY-UHFFFAOYSA-N methyl 4-chloro-3,5-bis(dimethylamino)benzoate Chemical compound COC(=O)C1=CC(N(C)C)=C(Cl)C(N(C)C)=C1 UYVHJAFBTJMJMY-UHFFFAOYSA-N 0.000 description 1
- BKPFNWOTGFBEDC-UHFFFAOYSA-N methyl 4-chloro-3-(dimethylamino)-5-(methylamino)benzoate Chemical compound CNC1=CC(C(=O)OC)=CC(N(C)C)=C1Cl BKPFNWOTGFBEDC-UHFFFAOYSA-N 0.000 description 1
- RUBZCUJJIVAPOK-UHFFFAOYSA-N methyl 4-methoxy-3,5-di(pyrrol-1-yl)benzoate Chemical compound C=1C(C(=O)OC)=CC(N2C=CC=C2)=C(OC)C=1N1C=CC=C1 RUBZCUJJIVAPOK-UHFFFAOYSA-N 0.000 description 1
- YGNQQIRSXQIZEN-UHFFFAOYSA-N methyl 4-tert-butyl-3,5-bis(dimethylamino)benzoate Chemical compound COC(=O)C1=CC(N(C)C)=C(C(C)(C)C)C(N(C)C)=C1 YGNQQIRSXQIZEN-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 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
- 238000007911 parenteral administration Methods 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical class OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005543 phthalimide group Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003195 pteridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004306 sulfadiazine Drugs 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
- 229960000654 sulfafurazole Drugs 0.000 description 1
- 229950003874 sulfamonomethoxine Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1728774A CH605828A5 (enrdf_load_stackoverflow) | 1974-12-24 | 1974-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2558150A1 true DE2558150A1 (de) | 1976-07-01 |
Family
ID=4424233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752558150 Ceased DE2558150A1 (de) | 1974-12-24 | 1975-12-23 | Neue benzylpyrimidine |
Country Status (25)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0003212A1 (de) * | 1977-11-10 | 1979-08-08 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 2.4-Diamino-5-benzylpyrimidine und diese enthaltende pharmazeutische Präparate sowie deren Herstellung |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2608670T3 (es) | 2009-08-17 | 2017-04-12 | Memorial Sloan-Kettering Cancer Center | Derivados de 2-(pirimidin-5-il)-tiopirimidina como moduladores de Hsp70 y Hsc70 para el tratamiento de trastornos proliferativos |
| US9878987B2 (en) | 2014-05-13 | 2018-01-30 | Memorial Sloan Kettering Cancer Center | HSP70 modulators and methods for making and using the same |
| CN120081720A (zh) * | 2025-02-18 | 2025-06-03 | 天津汇仁恒通科技有限公司 | 一种二乙烯基芳香化合物的制备方法 |
-
1974
- 1974-12-24 CH CH1728774A patent/CH605828A5/xx not_active IP Right Cessation
-
1975
- 1975-11-04 IL IL48416A patent/IL48416A/xx unknown
- 1975-11-05 ZA ZA00756964A patent/ZA756964B/xx unknown
- 1975-11-07 AU AU86433/75A patent/AU500102B2/en not_active Expired
- 1975-11-25 FI FI753312A patent/FI753312A7/fi not_active Application Discontinuation
- 1975-11-29 CU CU7534406A patent/CU34406A/es unknown
- 1975-12-08 NL NL7514269A patent/NL7514269A/xx not_active Application Discontinuation
- 1975-12-09 LU LU73971A patent/LU73971A1/xx unknown
- 1975-12-18 CA CA242,038A patent/CA1059127A/en not_active Expired
- 1975-12-19 HU HU75HO1864A patent/HU174324B/hu unknown
- 1975-12-22 BR BR8534/75A patent/BR7508534A/pt unknown
- 1975-12-22 SU SU752301512A patent/SU612629A3/ru active
- 1975-12-22 PH PH7517896A patent/PH12314A/en unknown
- 1975-12-22 FR FR7539341A patent/FR2295750A1/fr active Granted
- 1975-12-22 JP JP50152026A patent/JPS5191273A/ja active Pending
- 1975-12-22 AT AT975975A patent/AT344704B/de not_active IP Right Cessation
- 1975-12-23 DE DE19752558150 patent/DE2558150A1/de not_active Ceased
- 1975-12-23 GB GB52604/75A patent/GB1492140A/en not_active Expired
- 1975-12-23 BE BE163041A patent/BE836996A/xx unknown
- 1975-12-23 DD DD190511A patent/DD123603A5/xx unknown
- 1975-12-23 NO NO754372A patent/NO141408C/no unknown
- 1975-12-23 DK DK589675AA patent/DK137797B/da unknown
- 1975-12-23 PL PL1975185924A patent/PL101046B1/pl unknown
- 1975-12-23 ES ES443790A patent/ES443790A1/es not_active Expired
- 1975-12-23 SE SE7514642A patent/SE417607B/xx unknown
-
1977
- 1977-12-07 CH CH1499977A patent/CH617191A5/de not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0003212A1 (de) * | 1977-11-10 | 1979-08-08 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 2.4-Diamino-5-benzylpyrimidine und diese enthaltende pharmazeutische Präparate sowie deren Herstellung |
| EP0032395B1 (de) * | 1977-11-10 | 1983-03-23 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Benzylpyrimidine |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69129611T2 (de) | Sulfonamid-Derivate | |
| DE69831233T2 (de) | Barbitursaure derivaten mit antimetastatischer und antitumorischer wirkung | |
| DE3876813T4 (de) | 3(2H)Pyridazinon, Verfahren zu dessen Herstellung und dieses enthaltendes Mittel gegen SRS-A. | |
| DE2905877A1 (de) | Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE1185180B (de) | Verfahren zur Herstellung von Benzolsulfonylharnstoffen | |
| US4039543A (en) | Benzylpyrimidines | |
| EP0239907B1 (de) | Neue Phenoxyalkylcarbonsäure-Derivate, Verfahren zu ihrer Herstellung, sowie diese Verbindungen enthaltende Arzneimittel | |
| US4659818A (en) | Intermediates for benzylpyrimidines | |
| DE2731264A1 (de) | Neue 1-acyl-2-cyanaziridine, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische zubereitungen | |
| JPH0434545B2 (enrdf_load_stackoverflow) | ||
| DE3419009A1 (de) | Neue substituierte bis(4-aminophenyl)sulfone, ihre herstellung und ihre verwendung als arzneimittel | |
| DE3830060A1 (de) | 2-phenylbenzimidazole - verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel | |
| DE2443682C2 (de) | Neue 2,4-Diamino-5-benzylpyrimidine | |
| UA44237C2 (uk) | Арилбензоїлгуанідини, спосіб їх отримання, фармацевтична композиція | |
| DE2558150A1 (de) | Neue benzylpyrimidine | |
| DE2452889C2 (de) | Neue Benzylpyrimidine, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE3781703T2 (de) | 2-benzimidazolylalkylthio(oder sulfinyl- oder sulfonyl)-derivate, verfahren zu deren herstellung und deren anwendung als arzneimittel. | |
| EP0003212B1 (de) | 2.4-Diamino-5-benzylpyrimidine und diese enthaltende pharmazeutische Präparate sowie deren Herstellung | |
| DE69713128T2 (de) | 4-(1-piperazinyl)benzosäurederivate, verfahren zu ihrer herstellung und ihre therapeutischen verwendungen | |
| DE2526795A1 (de) | Sulfonamide | |
| DE3804346A1 (de) | Tert.-butylphenyl-pyridyl-amide - verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel | |
| DE2643384A1 (de) | Neue 5,6-dihydropyrimidin-4(3h)-onderivate, verfahren zu ihrer herstellung und ihre verwendung als wirkstoff in pharmazeutischen praeparaten | |
| DE2409313A1 (de) | Neue pyrrolyl-verbindungen und verfahren zu ihrer herstellung | |
| NO133892B (enrdf_load_stackoverflow) | ||
| DE2435934A1 (de) | Neue benzylpyrimidine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |