CA1059127A - Benzylpyrimidines - Google Patents
BenzylpyrimidinesInfo
- Publication number
- CA1059127A CA1059127A CA242,038A CA242038A CA1059127A CA 1059127 A CA1059127 A CA 1059127A CA 242038 A CA242038 A CA 242038A CA 1059127 A CA1059127 A CA 1059127A
- Authority
- CA
- Canada
- Prior art keywords
- group
- methyl
- bis
- ethyl acetate
- water
- 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
Links
- OOLOAWZLPBDRJQ-UHFFFAOYSA-N 2-benzylpyrimidine Chemical class N=1C=CC=NC=1CC1=CC=CC=C1 OOLOAWZLPBDRJQ-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 239000000460 chlorine Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002252 acyl group Chemical group 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
- 229960000789 guanidine hydrochloride Drugs 0.000 claims description 12
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 claims description 12
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
- 229960004198 guanidine Drugs 0.000 claims description 4
- GWFAIVOZRPTQMC-UHFFFAOYSA-N 5-[[4-chloro-3,5-bis(methylamino)phenyl]methyl]pyrimidine-2,4-diamine Chemical compound CNC1=C(Cl)C(NC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 GWFAIVOZRPTQMC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 4
- JGFZJURXNGLGFW-UHFFFAOYSA-N 5-[[4-chloro-3,5-bis(dimethylamino)phenyl]methyl]pyrimidine-2,4-diamine Chemical compound CN(C)C1=C(Cl)C(N(C)C)=CC(CC=2C(=NC(N)=NC=2)N)=C1 JGFZJURXNGLGFW-UHFFFAOYSA-N 0.000 claims 2
- 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
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 327
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 225
- 229940093499 ethyl acetate Drugs 0.000 description 109
- 235000019439 ethyl acetate Nutrition 0.000 description 109
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 101
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 100
- 239000000243 solution Substances 0.000 description 71
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 54
- 238000002844 melting Methods 0.000 description 52
- 230000008018 melting Effects 0.000 description 52
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 47
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 46
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 40
- 238000010992 reflux Methods 0.000 description 31
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 30
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 30
- 239000000725 suspension Substances 0.000 description 30
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 description 27
- 238000001953 recrystallisation Methods 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 239000003208 petroleum Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 229910052938 sodium sulfate Inorganic materials 0.000 description 20
- 235000011152 sodium sulphate Nutrition 0.000 description 20
- 229940076134 benzene Drugs 0.000 description 19
- 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 18
- 230000007717 exclusion Effects 0.000 description 18
- 239000011734 sodium Substances 0.000 description 18
- 229910052708 sodium Inorganic materials 0.000 description 18
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 17
- 235000019445 benzyl alcohol Nutrition 0.000 description 17
- 239000012312 sodium hydride Substances 0.000 description 17
- 229910000104 sodium hydride Inorganic materials 0.000 description 17
- ACRWYXSKEHUQDB-UHFFFAOYSA-N 3-phenylpropionitrile Chemical compound N#CCCC1=CC=CC=C1 ACRWYXSKEHUQDB-UHFFFAOYSA-N 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- 229960005363 aluminium oxide Drugs 0.000 description 10
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 229910021653 sulphate ion Inorganic materials 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- 230000002378 acidificating effect Effects 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
- 150000002431 hydrogen Chemical class 0.000 description 4
- 229960005404 sulfamethoxazole Drugs 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
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 229960001413 acetanilide Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- HLCNDOKDSIHQLX-UHFFFAOYSA-N 1-[3,5-bis(2,5-dimethylpyrrol-1-yl)-4-methylphenyl]-2-methylsulfonylethanone Chemical compound CC1=CC=C(C)N1C1=CC(C(=O)CS(C)(=O)=O)=CC(N2C(=CC=C2C)C)=C1C HLCNDOKDSIHQLX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 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
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
- HRKTYSDVSRVOIP-UHFFFAOYSA-N 2,2-diethoxyoxolane Chemical compound CCOC1(OCC)CCCO1 HRKTYSDVSRVOIP-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
- DZQNQDOHNLNOLM-UHFFFAOYSA-N 2-methylsulfonyl-1-[3,4,5-tris(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC(C(=O)CS(C)(=O)=O)=CC(N(C)C)=C1N(C)C DZQNQDOHNLNOLM-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000036366 Sensation of pressure Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000013078 crystal 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
- 239000011724 folic acid Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 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
- XTVNEXIFWBPKKY-UHFFFAOYSA-N methyl 2,6-diacetamido-4-methylbenzoate Chemical compound COC(=O)C1=C(NC(C)=O)C=C(C)C=C1NC(C)=O XTVNEXIFWBPKKY-UHFFFAOYSA-N 0.000 description 2
- VOFMMMRUFFLRQG-UHFFFAOYSA-N methyl 3,5-bis(2,5-dimethylpyrrol-1-yl)-4-methylbenzoate Chemical compound C=1C(C(=O)OC)=CC(N2C(=CC=C2C)C)=C(C)C=1N1C(C)=CC=C1C VOFMMMRUFFLRQG-UHFFFAOYSA-N 0.000 description 2
- 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 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
- NDHPGBKVMMEWRT-UHFFFAOYSA-N methyl 3,5-bis[acetyl(methyl)amino]benzoate Chemical compound COC(=O)C1=CC(N(C)C(C)=O)=CC(N(C)C(C)=O)=C1 NDHPGBKVMMEWRT-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
- PKEGOQLYQQVVSA-UHFFFAOYSA-N methyl 3,5-diacetamidobenzoate Chemical compound COC(=O)C1=CC(NC(C)=O)=CC(NC(C)=O)=C1 PKEGOQLYQQVVSA-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
- KXDARIRHTNMXDW-UHFFFAOYSA-N methyl 3,5-diamino-4-piperidin-1-ylbenzoate Chemical compound NC1=CC(C(=O)OC)=CC(N)=C1N1CCCCC1 KXDARIRHTNMXDW-UHFFFAOYSA-N 0.000 description 2
- DVZKXJOTHIYOQD-UHFFFAOYSA-N methyl 3,5-diamino-4-tert-butylbenzoate Chemical compound COC(=O)C1=CC(N)=C(C(C)(C)C)C(N)=C1 DVZKXJOTHIYOQD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- VFVNEZXDJRGJPB-UHFFFAOYSA-N 1-[3,5-bis(dimethylamino)-4-methoxyphenyl]-2-methylsulfonylethanone Chemical compound COC1=C(N(C)C)C=C(C(=O)CS(C)(=O)=O)C=C1N(C)C VFVNEZXDJRGJPB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- YSHZDKPNJXTSDJ-UHFFFAOYSA-N 1-[4-chloro-3,5-bis(methylamino)phenyl]-2-methylsulfonylethanone Chemical compound CNC1=CC(C(=O)CS(C)(=O)=O)=CC(NC)=C1Cl YSHZDKPNJXTSDJ-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 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 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
- 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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001676573 Minium Species 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 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
- 235000010210 aluminium Nutrition 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 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
- LDMPZJOBKLVTKW-UHFFFAOYSA-N butyl 3,5-dinitrobenzoate Chemical compound CCCCOC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 LDMPZJOBKLVTKW-UHFFFAOYSA-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
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 229940014144 folate Drugs 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 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
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- FQUDXIQIZOHIRY-UHFFFAOYSA-N methyl 2,6-bis[acetyl(methyl)amino]-4-methylbenzoate Chemical compound COC(=O)C1=C(N(C)C(C)=O)C=C(C)C=C1N(C)C(C)=O FQUDXIQIZOHIRY-UHFFFAOYSA-N 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
- GNFDZMCESFTRBJ-UHFFFAOYSA-N methyl 3,5-bis(dimethylamino)-4-methylbenzoate Chemical compound COC(=O)C1=CC(N(C)C)=C(C)C(N(C)C)=C1 GNFDZMCESFTRBJ-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
- 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 1
- 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 1
- BLOZAQDHRPWQOI-UHFFFAOYSA-N methyl 3,5-dinitro-4-piperidin-1-ylbenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC([N+]([O-])=O)=C1N1CCCCC1 BLOZAQDHRPWQOI-UHFFFAOYSA-N 0.000 description 1
- UZOFVZXCDSBEJW-UHFFFAOYSA-N methyl 3-(dimethylamino)-4-methoxy-5-(methylamino)benzoate Chemical compound CNC1=CC(C(=O)OC)=CC(N(C)C)=C1OC UZOFVZXCDSBEJW-UHFFFAOYSA-N 0.000 description 1
- ILVCNACMKNUGSR-UHFFFAOYSA-N methyl 3-[acetyl(methyl)amino]-5-(dimethylamino)-4-methoxybenzoate Chemical compound COC(=O)C1=CC(N(C)C)=C(OC)C(N(C)C(C)=O)=C1 ILVCNACMKNUGSR-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
- 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 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
- 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
- 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 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
- 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
- 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 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 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
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- ZXGWXACEYUVTOL-UHFFFAOYSA-N n-(2-methoxyphenyl)-n-methylacetamide Chemical compound COC1=CC=CC=C1N(C)C(C)=O ZXGWXACEYUVTOL-UHFFFAOYSA-N 0.000 description 1
- VWGDNOXVVQWSTI-UHFFFAOYSA-N n-[2,6-bis(dimethylamino)-4-(2-methylsulfonylacetyl)phenyl]-n-methylacetamide Chemical compound CN(C)C1=CC(C(=O)CS(C)(=O)=O)=CC(N(C)C)=C1N(C)C(C)=O VWGDNOXVVQWSTI-UHFFFAOYSA-N 0.000 description 1
- JIWHZXVBRGVPTE-UHFFFAOYSA-N n-[5-(1-hydroxy-2-methylsulfonylethyl)-2-methyl-3-(methylamino)phenyl]-n-methylacetamide Chemical compound CNC1=CC(C(O)CS(C)(=O)=O)=CC(N(C)C(C)=O)=C1C JIWHZXVBRGVPTE-UHFFFAOYSA-N 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003456 sulfonamides Chemical class 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
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 (en:Method) | 1974-12-24 | 1974-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1059127A true CA1059127A (en) | 1979-07-24 |
Family
ID=4424233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA242,038A Expired CA1059127A (en) | 1974-12-24 | 1975-12-18 | Benzylpyrimidines |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5191273A (en:Method) |
| AT (1) | AT344704B (en:Method) |
| AU (1) | AU500102B2 (en:Method) |
| BE (1) | BE836996A (en:Method) |
| BR (1) | BR7508534A (en:Method) |
| CA (1) | CA1059127A (en:Method) |
| CH (2) | CH605828A5 (en:Method) |
| CU (1) | CU34406A (en:Method) |
| DD (1) | DD123603A5 (en:Method) |
| DE (1) | DE2558150A1 (en:Method) |
| DK (1) | DK137797B (en:Method) |
| ES (1) | ES443790A1 (en:Method) |
| FI (1) | FI753312A7 (en:Method) |
| FR (1) | FR2295750A1 (en:Method) |
| GB (1) | GB1492140A (en:Method) |
| HU (1) | HU174324B (en:Method) |
| IL (1) | IL48416A (en:Method) |
| LU (1) | LU73971A1 (en:Method) |
| NL (1) | NL7514269A (en:Method) |
| NO (1) | NO141408C (en:Method) |
| PH (1) | PH12314A (en:Method) |
| PL (1) | PL101046B1 (en:Method) |
| SE (1) | SE417607B (en:Method) |
| SU (1) | SU612629A3 (en:Method) |
| ZA (1) | ZA756964B (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR71725B (en:Method) * | 1977-11-10 | 1983-06-22 | Hoffmann La Roche | |
| NZ598262A (en) * | 2009-08-17 | 2014-05-30 | Sloan Kettering Inst Cancer | Heat shock protein binding compounds, compositions, and methods for making and using same |
| MX375924B (es) | 2014-05-13 | 2025-03-07 | Memorial Sloan Kettering Cancer Center | Moduladores de proteinas del choque termico 70 (hsp70) y metodos para fabricar y usar el mismo. |
| 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 JP JP50152026A patent/JPS5191273A/ja active Pending
- 1975-12-22 BR BR8534/75A patent/BR7508534A/pt unknown
- 1975-12-22 PH PH7517896A patent/PH12314A/en unknown
- 1975-12-22 SU SU752301512A patent/SU612629A3/ru active
- 1975-12-22 AT AT975975A patent/AT344704B/de not_active IP Right Cessation
- 1975-12-22 FR FR7539341A patent/FR2295750A1/fr active Granted
- 1975-12-23 PL PL1975185924A patent/PL101046B1/pl unknown
- 1975-12-23 BE BE163041A patent/BE836996A/xx unknown
- 1975-12-23 NO NO754372A patent/NO141408C/no unknown
- 1975-12-23 SE SE7514642A patent/SE417607B/xx unknown
- 1975-12-23 DE DE19752558150 patent/DE2558150A1/de not_active Ceased
- 1975-12-23 DD DD190511A patent/DD123603A5/xx unknown
- 1975-12-23 GB GB52604/75A patent/GB1492140A/en not_active Expired
- 1975-12-23 DK DK589675AA patent/DK137797B/da unknown
- 1975-12-23 ES ES443790A patent/ES443790A1/es not_active Expired
-
1977
- 1977-12-07 CH CH1499977A patent/CH617191A5/de not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4808715A (en) | 4-quinazolinylamino and 4-cinnolinylamino benzenesulphonic acids and amides | |
| US3283003A (en) | 2-(n-lower alkyl-n-cycloheptyl- and cyclooctylamino) ethyl guanidines | |
| CA1116611A (en) | Imidazole derivatives exhibiting anticonvulsant activity | |
| US5302720A (en) | Biphenyl-substituted guanidine derivatives useful as hypoglycaemic agents | |
| DK154022B (da) | Fremgangsmaade til fremstilling af benzothiazepinderivater | |
| US3697512A (en) | 5-benzyl pyrimidines intermediates | |
| US4251454A (en) | Benzylpyrimidines | |
| US4515948A (en) | 2,4-Diamino-5-(4-amino and 4-dimethylamino-3,5-dimethoxy benzyl)pyrimidines | |
| CA1059127A (en) | Benzylpyrimidines | |
| US4618622A (en) | Sulfonates of hydroxycoumarins | |
| CA1140546A (en) | Pyrazinobenzodiazepines | |
| US3853875A (en) | Esters of 2-alkyl thiazole 5-carboxylic acid | |
| CA1202629A (en) | Process for the preparation of 2-acyl-1,3,4,6,7,11b- hexahydro-2h-pyrazino-¬2,1-a|-4-isoquinoleinones and intermediates | |
| US3855265A (en) | 5-benzyl pyrimidines intermediates therefore, and method | |
| EP0543891A1 (en) | Diphenylurea derivatives | |
| FR2522000A1 (fr) | Nouvelles thiopyrannopyrimidines, utiles notamment comme agents hypoglycemiants, et leur fabrication | |
| US4499105A (en) | Carboxyimidamide derivatives | |
| US2944053A (en) | Uiiilcu | |
| KR900007315B1 (ko) | 1-[2-(페닐메틸)페닐]피페라진 및 그의 산부가염 | |
| IE47210B1 (en) | Improvements in the production of heterocyclic benzamide compounds | |
| US5436244A (en) | Indane derivatives and analgesic and diuretic compositions thereof | |
| US4200759A (en) | Preparation of imidazo[2,1-a]isoindole compounds | |
| US3991050A (en) | Preparation of β-Amino-α-benzylacrylonitriles | |
| EP0029306A1 (en) | Aminoalkyl compounds, their production and pharmaceutical compositions containing them | |
| US3956327A (en) | Method of preparing 2,4-diamino-5-benzyl pyrimidines |