DE2609208A1 - Pyrimidinyl-harnstoffe - Google Patents
Pyrimidinyl-harnstoffeInfo
- Publication number
- DE2609208A1 DE2609208A1 DE19762609208 DE2609208A DE2609208A1 DE 2609208 A1 DE2609208 A1 DE 2609208A1 DE 19762609208 DE19762609208 DE 19762609208 DE 2609208 A DE2609208 A DE 2609208A DE 2609208 A1 DE2609208 A1 DE 2609208A1
- Authority
- DE
- Germany
- Prior art keywords
- pyridinyl
- pyrimidinyl
- formula
- urea
- hydrogen
- 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.)
- Pending
Links
- DNENQQPLJPZMGZ-UHFFFAOYSA-N pyrimidin-2-ylurea Chemical compound NC(=O)NC1=NC=CC=N1 DNENQQPLJPZMGZ-UHFFFAOYSA-N 0.000 title 1
- -1 2-pyridinyl Chemical group 0.000 claims description 128
- 150000001875 compounds Chemical class 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 19
- 239000004202 carbamide Substances 0.000 claims description 18
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 239000012458 free base Substances 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- CNKRRFAEIGKEGM-UHFFFAOYSA-N (2-pyridin-4-ylpyrimidin-4-yl)urea Chemical compound NC(=O)NC1=CC=NC(C=2C=CN=CC=2)=N1 CNKRRFAEIGKEGM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- SJJOXQXXTAJQNH-UHFFFAOYSA-N 1-propan-2-yl-3-(2-pyridin-4-ylpyrimidin-4-yl)urea Chemical compound CC(C)NC(=O)NC1=CC=NC(C=2C=CN=CC=2)=N1 SJJOXQXXTAJQNH-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 210000002700 urine Anatomy 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
- 239000000203 mixture Substances 0.000 description 55
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 39
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 235000019441 ethanol Nutrition 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- AFNZWLWIUXHAIW-UHFFFAOYSA-N 2-pyridin-4-ylpyrimidin-4-amine Chemical compound NC1=CC=NC(C=2C=CN=CC=2)=N1 AFNZWLWIUXHAIW-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 24
- 239000007787 solid Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 229910000104 sodium hydride Inorganic materials 0.000 description 20
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000012312 sodium hydride Substances 0.000 description 19
- 239000004533 oil dispersion Substances 0.000 description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 12
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 235000013877 carbamide Nutrition 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 239000000908 ammonium hydroxide Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- KNXKVYCVGXFLES-UHFFFAOYSA-N pyridine-2-carboximidamide Chemical compound NC(=N)C1=CC=CC=N1 KNXKVYCVGXFLES-UHFFFAOYSA-N 0.000 description 7
- OBXXCFFJBAUAAE-UHFFFAOYSA-N 1-tert-butyl-3-(2-pyridin-4-ylpyrimidin-4-yl)urea Chemical compound CC(C)(C)NC(=O)NC1=CC=NC(C=2C=CN=CC=2)=N1 OBXXCFFJBAUAAE-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 5
- USBDVWRRXXQEOL-UHFFFAOYSA-N 2-pyridin-3-ylpyrimidin-4-amine Chemical compound NC1=CC=NC(C=2C=NC=CC=2)=N1 USBDVWRRXXQEOL-UHFFFAOYSA-N 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- GGQNTXJGAGWGFD-UHFFFAOYSA-N n-(2-pyridin-4-ylpyrimidin-4-yl)imidazole-1-carboxamide Chemical compound C1=CN=CN1C(=O)NC(N=1)=CC=NC=1C1=CC=NC=C1 GGQNTXJGAGWGFD-UHFFFAOYSA-N 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- CRLLPKLYUMUJHY-UHFFFAOYSA-N 2-pyridin-2-ylpyrimidin-4-amine Chemical class NC1=CC=NC(C=2N=CC=CC=2)=N1 CRLLPKLYUMUJHY-UHFFFAOYSA-N 0.000 description 4
- IONKMFGAXKCLMI-UHFFFAOYSA-N [amino(pyridin-4-yl)methylidene]azanium;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=NC=C1 IONKMFGAXKCLMI-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- VIHXWWJJHFGFIX-UHFFFAOYSA-N (6-methyl-2-pyridin-4-ylpyrimidin-4-yl)hydrazine Chemical compound CC1=CC(NN)=NC(C=2C=CN=CC=2)=N1 VIHXWWJJHFGFIX-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- UFMQZZRBKSOEKS-UHFFFAOYSA-N 6-methyl-2-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound N1C(C)=CC(=O)N=C1C1=CC=NC=C1 UFMQZZRBKSOEKS-UHFFFAOYSA-N 0.000 description 3
- MPYZHDZCEHZQSB-UHFFFAOYSA-N 6-propyl-2-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound CCCC1=CC(O)=NC(C=2C=CN=CC=2)=N1 MPYZHDZCEHZQSB-UHFFFAOYSA-N 0.000 description 3
- FDBQKMBNSZRZOG-UHFFFAOYSA-N 6-propyl-2-pyridin-4-ylpyrimidin-4-amine Chemical compound CCCC1=CC(N)=NC(C=2C=CN=CC=2)=N1 FDBQKMBNSZRZOG-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000003266 anti-allergic effect Effects 0.000 description 3
- 239000000043 antiallergic agent Substances 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003610 charcoal Substances 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
- 238000001816 cooling Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- XRCXVDGCHVDNNM-UHFFFAOYSA-N n-methyl-2-pyridin-4-ylpyrimidin-4-amine Chemical compound CNC1=CC=NC(C=2C=CN=CC=2)=N1 XRCXVDGCHVDNNM-UHFFFAOYSA-N 0.000 description 3
- GVDHZFJYZKAQNS-UHFFFAOYSA-N n-tert-butyl-2-pyridin-4-ylpyrimidin-4-amine Chemical compound CC(C)(C)NC1=CC=NC(C=2C=CN=CC=2)=N1 GVDHZFJYZKAQNS-UHFFFAOYSA-N 0.000 description 3
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 2
- HUPVIAINOSTNBJ-HWKANZROSA-N (e)-3-ethoxyprop-2-enenitrile Chemical compound CCO\C=C\C#N HUPVIAINOSTNBJ-HWKANZROSA-N 0.000 description 2
- AADBRLIAYJLVMH-UHFFFAOYSA-N 2-(2-ethylpyridin-4-yl)pyrimidin-4-amine Chemical compound C1=NC(CC)=CC(C=2N=C(N)C=CN=2)=C1 AADBRLIAYJLVMH-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- DHNOAUDHLPLXQG-UHFFFAOYSA-N 4-amino-2-pyridin-4-ylpyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(N)=NC(C=2C=CN=CC=2)=N1 DHNOAUDHLPLXQG-UHFFFAOYSA-N 0.000 description 2
- BBRWYVYBIRGEQK-UHFFFAOYSA-N 4-chloro-2-pyridin-4-ylpyrimidine Chemical compound ClC1=CC=NC(C=2C=CN=CC=2)=N1 BBRWYVYBIRGEQK-UHFFFAOYSA-N 0.000 description 2
- ZSRSIZQAKUIMTE-UHFFFAOYSA-N 4-chloro-6-methyl-2-pyridin-4-ylpyrimidine Chemical compound CC1=CC(Cl)=NC(C=2C=CN=CC=2)=N1 ZSRSIZQAKUIMTE-UHFFFAOYSA-N 0.000 description 2
- JMDXPMYETBVHIN-UHFFFAOYSA-N 6-amino-2-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound N1C(N)=CC(=O)N=C1C1=CC=NC=C1 JMDXPMYETBVHIN-UHFFFAOYSA-N 0.000 description 2
- KNKKGGMVDGAMLG-UHFFFAOYSA-N 6-methyl-2-pyridin-4-ylpyrimidin-4-amine Chemical compound CC1=CC(N)=NC(C=2C=CN=CC=2)=N1 KNKKGGMVDGAMLG-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000147 hypnotic effect Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
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- 239000013067 intermediate product Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000037230 mobility Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- HGXADWSUAXJGSP-UHFFFAOYSA-N n,6-dimethyl-2-pyridin-4-ylpyrimidin-4-amine Chemical compound CNC1=CC(C)=NC(C=2C=CN=CC=2)=N1 HGXADWSUAXJGSP-UHFFFAOYSA-N 0.000 description 1
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 1
- ZZLJJAGIUYYIRN-UHFFFAOYSA-N n-(2-pyridin-4-ylpyrimidin-4-yl)acetamide Chemical compound CC(=O)NC1=CC=NC(C=2C=CN=CC=2)=N1 ZZLJJAGIUYYIRN-UHFFFAOYSA-N 0.000 description 1
- YDFTXRCSHWSELZ-UHFFFAOYSA-N n-ethyl-n-(2-pyridin-4-ylpyrimidin-4-yl)imidazole-1-carboxamide Chemical compound C=1C=NC(C=2C=CN=CC=2)=NC=1N(CC)C(=O)N1C=CN=C1 YDFTXRCSHWSELZ-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- DNEXFQYHSNWHMY-UHFFFAOYSA-N n-methyl-n-(2-pyridin-4-ylpyrimidin-4-yl)imidazole-1-carboxamide Chemical compound C=1C=NC(C=2C=CN=CC=2)=NC=1N(C)C(=O)N1C=CN=C1 DNEXFQYHSNWHMY-UHFFFAOYSA-N 0.000 description 1
- UJKKNNPWQLWKRY-UHFFFAOYSA-N n-propan-2-yl-n-(2-pyridin-4-ylpyrimidin-4-yl)imidazole-1-carboxamide Chemical compound C=1C=NC(C=2C=CN=CC=2)=NC=1N(C(C)C)C(=O)N1C=CN=C1 UJKKNNPWQLWKRY-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- VQCNPHBZGNFQBI-UHFFFAOYSA-N pyridine-3-carboximidamide;dihydrochloride Chemical compound Cl.Cl.NC(=N)C1=CC=CN=C1 VQCNPHBZGNFQBI-UHFFFAOYSA-N 0.000 description 1
- BIJRUEBMNUUNIJ-UHFFFAOYSA-N pyridine-4-carboximidamide Chemical compound NC(=N)C1=CC=NC=C1 BIJRUEBMNUUNIJ-UHFFFAOYSA-N 0.000 description 1
- ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/556,213 US4008235A (en) | 1975-03-07 | 1975-03-07 | N-[2-(pyridinyl)-4-pyrimidinyl]ureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2609208A1 true DE2609208A1 (de) | 1976-09-16 |
Family
ID=24220364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762609208 Pending DE2609208A1 (de) | 1975-03-07 | 1976-03-05 | Pyrimidinyl-harnstoffe |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4008235A (enExample) |
| JP (1) | JPS51113884A (enExample) |
| AU (1) | AU1169176A (enExample) |
| BE (1) | BE839163A (enExample) |
| CA (1) | CA1051432A (enExample) |
| DE (1) | DE2609208A1 (enExample) |
| DK (1) | DK97476A (enExample) |
| FI (1) | FI760555A7 (enExample) |
| FR (1) | FR2302744A1 (enExample) |
| GB (1) | GB1530412A (enExample) |
| NL (1) | NL7602379A (enExample) |
| NO (1) | NO760779L (enExample) |
| PH (1) | PH11387A (enExample) |
| SE (1) | SE7603051L (enExample) |
| ZA (1) | ZA761300B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0122580A1 (de) * | 1983-04-14 | 1984-10-24 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyrimidinderivate, deren Herstellung und pharmazeutische Präparate |
| US4752608A (en) * | 1985-12-03 | 1988-06-21 | Sumitomo Chemical Company, Limited | Fungicidal pyridinylpyrimidine derivatives |
| US4783466A (en) * | 1986-09-05 | 1988-11-08 | Sumitomo Chemical Company, Limited | Novel pyridinylpyrimidine derivatives, method for production thereof and a plant disease protectant containing them as the active ingredient |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4144338A (en) * | 1977-02-17 | 1979-03-13 | Merck & Co., Inc. | N-pyrimidinyl-N-dialkylaminoalkyl ureas |
| US4415575A (en) * | 1979-03-13 | 1983-11-15 | Merck & Co., Inc. | Suppression of gastric acid secretion using pyrimidylcarbamates |
| US4226871A (en) * | 1979-03-13 | 1980-10-07 | Merck & Co., Inc. | Heterocyclic carbamates |
| US4504482A (en) * | 1983-07-28 | 1985-03-12 | Sterling Drug Inc. | [5(or 4)-(Pyridinyl)-2-pyrimidinyl]ureas and cardiotonic use thereof |
| NZ219486A (en) * | 1987-03-04 | 1990-05-28 | Kenneth Wilfred Feisst | Foldable and rollable building |
| ATE139117T1 (de) * | 1990-07-03 | 1996-06-15 | Mitsui Petrochemical Ind | Pyrimidin-verbindung und ihr pharmazeutisch annehmbares salz |
| EP2368883A1 (en) * | 2010-03-24 | 2011-09-28 | Lonza Ltd. | Process for the preparation of 2-substituted 4-amino-5-cyanopyrimidines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3673184A (en) * | 1970-09-02 | 1972-06-27 | Dainippon Pharmaceutical Co | Certain 2-substituted-5,8-dihydro-5-oxopyrido{8 2,3-d{9 pyrimidine-6-carboxylic acid derivatives |
-
1975
- 1975-03-07 US US05/556,213 patent/US4008235A/en not_active Expired - Lifetime
-
1976
- 1976-02-23 GB GB7110/76A patent/GB1530412A/en not_active Expired
- 1976-03-04 ZA ZA761300A patent/ZA761300B/xx unknown
- 1976-03-04 AU AU11691/76A patent/AU1169176A/en not_active Expired
- 1976-03-04 FI FI760555A patent/FI760555A7/fi not_active Application Discontinuation
- 1976-03-04 CA CA247,151A patent/CA1051432A/en not_active Expired
- 1976-03-04 BE BE1007228A patent/BE839163A/xx unknown
- 1976-03-05 JP JP51024067A patent/JPS51113884A/ja active Pending
- 1976-03-05 SE SE7603051A patent/SE7603051L/xx unknown
- 1976-03-05 NL NL7602379A patent/NL7602379A/xx not_active Application Discontinuation
- 1976-03-05 PH PH18176A patent/PH11387A/en unknown
- 1976-03-05 NO NO760779A patent/NO760779L/no unknown
- 1976-03-05 FR FR7606352A patent/FR2302744A1/fr active Granted
- 1976-03-05 DE DE19762609208 patent/DE2609208A1/de active Pending
- 1976-03-05 DK DK97476*#A patent/DK97476A/da unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0122580A1 (de) * | 1983-04-14 | 1984-10-24 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyrimidinderivate, deren Herstellung und pharmazeutische Präparate |
| US4590270A (en) * | 1983-04-14 | 1986-05-20 | Hoffmann-La Roche Inc. | 2,4-diamino-[4-piperidinyl]pyrimidines useful as antibacterial agents, antimalarial agents, antitumors agents |
| US4774249A (en) * | 1983-04-14 | 1988-09-27 | Hoffmann-La Roche Inc. | Pyrimidine derivatives for treating malaria |
| US4752608A (en) * | 1985-12-03 | 1988-06-21 | Sumitomo Chemical Company, Limited | Fungicidal pyridinylpyrimidine derivatives |
| US4783466A (en) * | 1986-09-05 | 1988-11-08 | Sumitomo Chemical Company, Limited | Novel pyridinylpyrimidine derivatives, method for production thereof and a plant disease protectant containing them as the active ingredient |
Also Published As
| Publication number | Publication date |
|---|---|
| SE7603051L (sv) | 1976-09-08 |
| NL7602379A (nl) | 1976-09-09 |
| ZA761300B (en) | 1977-02-23 |
| NO760779L (enExample) | 1976-09-08 |
| FR2302744B1 (enExample) | 1979-09-21 |
| BE839163A (fr) | 1976-09-06 |
| DK97476A (da) | 1976-09-08 |
| JPS51113884A (en) | 1976-10-07 |
| FI760555A7 (enExample) | 1976-09-08 |
| PH11387A (en) | 1977-11-22 |
| US4008235A (en) | 1977-02-15 |
| GB1530412A (en) | 1978-11-01 |
| CA1051432A (en) | 1979-03-27 |
| AU1169176A (en) | 1977-09-08 |
| FR2302744A1 (fr) | 1976-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |