CS210684B2 - Manufacturing process of 2-aminopyrimidones - Google Patents
Manufacturing process of 2-aminopyrimidones Download PDFInfo
- Publication number
- CS210684B2 CS210684B2 CS792440A CS244079A CS210684B2 CS 210684 B2 CS210684 B2 CS 210684B2 CS 792440 A CS792440 A CS 792440A CS 244079 A CS244079 A CS 244079A CS 210684 B2 CS210684 B2 CS 210684B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- pyrimidone
- pyridyl
- formula
- methoxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 23
- 150000001412 amines Chemical class 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- -1 4-imidazolyl Chemical group 0.000 claims description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 14
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- MWOMLXUCWMNOPU-UHFFFAOYSA-N 2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-5-(naphthalen-1-ylmethyl)-1h-pyrimidin-6-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(CC=3C4=CC=CC=C4C=CC=3)=CN=2)=C1C MWOMLXUCWMNOPU-UHFFFAOYSA-N 0.000 claims 1
- IEXLKRXFLWBFFK-UHFFFAOYSA-N 5-(furan-2-ylmethyl)-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-1h-pyrimidin-6-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(CC=3OC=CC=3)=CN=2)=C1C IEXLKRXFLWBFFK-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical group OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- RHHFNUQDIRYPSI-UHFFFAOYSA-N n-[6-oxo-5-(pyridin-3-ylmethyl)-1h-pyrimidin-2-yl]nitramide Chemical compound N1C(N[N+](=O)[O-])=NC(=O)C(CC=2C=NC=CC=2)=C1 RHHFNUQDIRYPSI-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 3
- JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000006309 butyl amino group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- BKTHTLOKUUJKDF-UHFFFAOYSA-N (3,4-dimethoxypyridin-2-yl)methanol Chemical compound COC1=CC=NC(CO)=C1OC BKTHTLOKUUJKDF-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- IHDFTEVCMVTMSP-UHFFFAOYSA-N 3-(1h-imidazol-5-yl)propan-1-amine Chemical compound NCCCC1=CN=CN1 IHDFTEVCMVTMSP-UHFFFAOYSA-N 0.000 description 2
- XMLZZXNLTIVKDH-UHFFFAOYSA-N 4-(3-methoxypyridin-2-yl)butan-1-amine Chemical compound COC1=CC=CN=C1CCCCN XMLZZXNLTIVKDH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- ZNEYACZYGQIIBD-UHFFFAOYSA-N 2-(4-aminobutyl)pyridin-3-amine Chemical compound NCCCCC1=NC=CC=C1N ZNEYACZYGQIIBD-UHFFFAOYSA-N 0.000 description 1
- YYRIKJFWBIEEDH-UHFFFAOYSA-N 2-(chloromethyl)-3,4-dimethoxypyridine;hydrochloride Chemical compound [Cl-].COC1=CC=[NH+]C(CCl)=C1OC YYRIKJFWBIEEDH-UHFFFAOYSA-N 0.000 description 1
- NDSOSIAPHKRCJO-UHFFFAOYSA-N 2-(pyridin-3-ylmethyl)-1h-pyrimidin-6-one Chemical compound N1C(=O)C=CN=C1CC1=CC=CN=C1 NDSOSIAPHKRCJO-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- QHJYNLSDUKIRKX-UHFFFAOYSA-N 2-[(3,4-dimethoxypyridin-2-yl)methylsulfanyl]ethanamine Chemical compound COC1=CC=NC(CSCCN)=C1OC QHJYNLSDUKIRKX-UHFFFAOYSA-N 0.000 description 1
- APBNCYNMFCVXTJ-UHFFFAOYSA-N 2-[(4-methoxypyridin-2-yl)methylsulfanyl]ethanamine Chemical compound COC1=CC=NC(CSCCN)=C1 APBNCYNMFCVXTJ-UHFFFAOYSA-N 0.000 description 1
- QAOGVINQCKIBIH-UHFFFAOYSA-N 2-[(4-methylpyridin-2-yl)methylsulfanyl]ethanamine Chemical compound CC1=CC=NC(CSCCN)=C1 QAOGVINQCKIBIH-UHFFFAOYSA-N 0.000 description 1
- MVTQMQOUTRFYBV-UHFFFAOYSA-N 2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-5-[(3,4,5-trimethoxyphenyl)methyl]-1h-pyrimidin-6-one;dihydrochloride Chemical compound Cl.Cl.COC1=C(OC)C(OC)=CC(CC=2C(NC(NCCSCC3=C(NC=N3)C)=NC=2)=O)=C1 MVTQMQOUTRFYBV-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- UYHSQVMHSFXUOA-UHFFFAOYSA-N 2-methylthiouracil Chemical class CSC1=NC=CC(O)=N1 UYHSQVMHSFXUOA-UHFFFAOYSA-N 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- UMVFRRJTPKYVAY-UHFFFAOYSA-N 3,4-dimethoxy-2-methyl-1-oxidopyridin-1-ium Chemical compound COC1=CC=[N+]([O-])C(C)=C1OC UMVFRRJTPKYVAY-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- YJEYWIPRJYQEQT-UHFFFAOYSA-N 3-fluoro-2-methyl-4-nitro-1-oxidopyridin-1-ium Chemical compound CC1=C(F)C([N+]([O-])=O)=CC=[N+]1[O-] YJEYWIPRJYQEQT-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- XFZLAEXVWQCHMU-UHFFFAOYSA-N 4-(5-methyl-1h-imidazol-4-yl)butan-1-amine Chemical compound CC=1NC=NC=1CCCCN XFZLAEXVWQCHMU-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- HSPFMBDMLOMUFX-UHFFFAOYSA-N 5-(pyridin-3-ylmethyl)-2-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethylamino]-1h-pyrimidin-6-one;trihydrochloride Chemical compound Cl.Cl.Cl.N=1C=C(CC=2C=NC=CC=2)C(=O)NC=1NCCSCC1=NC=CS1 HSPFMBDMLOMUFX-UHFFFAOYSA-N 0.000 description 1
- JJGIHBJLNFAPHS-UHFFFAOYSA-N 5-[(3-methoxyphenyl)methyl]-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-1h-pyrimidin-6-one Chemical compound COC1=CC=CC(CC=2C(NC(NCCSCC3=C(NC=N3)C)=NC=2)=O)=C1 JJGIHBJLNFAPHS-UHFFFAOYSA-N 0.000 description 1
- CGKPDXUUNUWOKX-UHFFFAOYSA-N 5-[(4-methoxypyridin-2-yl)methyl]-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-1h-pyrimidin-6-one Chemical compound COC1=CC=NC(CC=2C(NC(NCCSCC3=C(NC=N3)C)=NC=2)=O)=C1 CGKPDXUUNUWOKX-UHFFFAOYSA-N 0.000 description 1
- LLJWCSIIIOZBBH-UHFFFAOYSA-N 5-[(5,6-dimethylpyridin-3-yl)methyl]-2-[4-(3-methoxypyridin-2-yl)butylamino]-1h-pyrimidin-6-one;dihydrate Chemical compound O.O.COC1=CC=CN=C1CCCCNC(NC1=O)=NC=C1CC1=CN=C(C)C(C)=C1 LLJWCSIIIOZBBH-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical compound [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- WIYSTOBNCJBCKL-UHFFFAOYSA-N n-(6-oxo-1h-pyrimidin-2-yl)nitramide Chemical compound [O-][N+](=O)NC1=NC(=O)C=CN1 WIYSTOBNCJBCKL-UHFFFAOYSA-N 0.000 description 1
- QGWDKSNKGFBHBZ-UHFFFAOYSA-N n-[5-(naphthalen-1-ylmethyl)-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound O=C1NC(N[N+](=O)[O-])=NC=C1CC1=CC=CC2=CC=CC=C12 QGWDKSNKGFBHBZ-UHFFFAOYSA-N 0.000 description 1
- RHOIVJHCCZBVSO-UHFFFAOYSA-N n-[5-[(6-methoxypyridin-3-yl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound C1=NC(OC)=CC=C1CC1=CN=C(N[N+]([O-])=O)NC1=O RHOIVJHCCZBVSO-UHFFFAOYSA-N 0.000 description 1
- KWBSLRQDOHBJPQ-UHFFFAOYSA-N n-[5-[(6-methylpyridin-3-yl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound C1=NC(C)=CC=C1CC1=CN=C(N[N+]([O-])=O)NC1=O KWBSLRQDOHBJPQ-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
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS804466A CS210685B2 (cs) | 1979-04-10 | 1980-06-24 | Způsob výroby 2-nitroaminopyrimidonů |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1404978 | 1978-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS210684B2 true CS210684B2 (en) | 1982-01-29 |
Family
ID=10034068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS792440A CS210684B2 (en) | 1978-04-11 | 1979-04-10 | Manufacturing process of 2-aminopyrimidones |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4523015A (ro) |
| EP (1) | EP0004793B1 (ro) |
| JP (1) | JPS54138580A (ro) |
| KR (1) | KR820002136B1 (ro) |
| AT (1) | AT372956B (ro) |
| AU (1) | AU527202B2 (ro) |
| CA (1) | CA1138453A (ro) |
| CS (1) | CS210684B2 (ro) |
| CY (1) | CY1194A (ro) |
| DD (1) | DD142878A5 (ro) |
| DE (1) | DE2961652D1 (ro) |
| DK (1) | DK147379A (ro) |
| ES (1) | ES479469A1 (ro) |
| FI (1) | FI791143A7 (ro) |
| GR (1) | GR66986B (ro) |
| HU (1) | HU180081B (ro) |
| IE (1) | IE48080B1 (ro) |
| IL (1) | IL57005A (ro) |
| IT (1) | IT1118476B (ro) |
| KE (1) | KE3284A (ro) |
| MX (1) | MX5898E (ro) |
| MY (1) | MY8500703A (ro) |
| NO (1) | NO791225L (ro) |
| NZ (1) | NZ190122A (ro) |
| PH (2) | PH16240A (ro) |
| PL (2) | PL118404B1 (ro) |
| PT (1) | PT69464A (ro) |
| RO (1) | RO76810A (ro) |
| SU (2) | SU944504A3 (ro) |
| YU (1) | YU84179A (ro) |
| ZA (1) | ZA791616B (ro) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN151188B (ro) * | 1978-02-13 | 1983-03-05 | Smith Kline French Lab | |
| CA1140129A (en) * | 1979-08-21 | 1983-01-25 | Ronald J. King | 4-pyrimidone derivatives |
| CA1155842A (en) * | 1980-03-29 | 1983-10-25 | Thomas H. Brown | Compounds |
| US4352933A (en) * | 1981-02-06 | 1982-10-05 | Smithkline Beckman Corporation | Chemical methods and intermediates for preparing substituted pyrimidinones |
| ZA823149B (en) * | 1981-05-27 | 1983-03-30 | Smithkline Beckman Corp | Chemical process |
| PT74865B (en) * | 1981-05-27 | 1983-12-07 | Smithkline Beckman Corp | Process of preparing a 2-(pyridylbutylamino)-pyrimidone and of its pharmaceutically acceptable salts |
| DK230482A (da) * | 1981-05-30 | 1982-12-01 | Smith Kline French Lab | Pyrimidonsalt og fremstilling heraf |
| US4772704A (en) * | 1983-09-21 | 1988-09-20 | Bristol-Myers Company | 2,5-disubstituted-4(3H)-pyrimidones having histamine H2 -receptor antagonist activity |
| IL75400A (en) * | 1984-06-16 | 1988-10-31 | Byk Gulden Lomberg Chem Fab | Dialkoxypyridine methyl(sulfinyl or sulfonyl)benzimidazoles,processes for the preparation thereof and pharmaceutical compositions containing the same |
| GB8421427D0 (en) * | 1984-08-23 | 1984-09-26 | Smith Kline French Lab | Chemical compounds |
| DE3532880A1 (de) * | 1985-09-14 | 1987-03-26 | Basf Ag | 1,4-disubstituierte pyrazolderivate |
| JP2807577B2 (ja) * | 1990-06-15 | 1998-10-08 | エーザイ株式会社 | 環状アミド誘導体 |
| CN107698501A (zh) * | 2017-10-25 | 2018-02-16 | 遵义医学院 | 5,6‑二甲基‑2‑羟基烟酸的制备工艺 |
| US20230349922A1 (en) | 2020-08-11 | 2023-11-02 | Université De Strasbourg | H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE787372A (fr) * | 1971-08-09 | 1973-02-09 | Ici Ltd | 2-nitroamino-6-hydroxy-4-methylpyrimidines substituees en position 5 |
| GB1383676A (en) * | 1972-07-14 | 1974-02-12 | Ici Ltd | Process for making diethylamino pyrimidine derivatives |
| GB1419994A (en) * | 1973-05-03 | 1976-01-07 | Smith Kline French Lab | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
| US4145546A (en) * | 1975-10-02 | 1979-03-20 | Smith Kline & French Laboratories Limited | 4-Pyrimidone compounds |
| IN146736B (ro) * | 1975-10-02 | 1979-08-25 | Smith Kline French Lab | |
| US4216318A (en) * | 1975-12-29 | 1980-08-05 | Smith Kline & French Laboratories Limited | Heterocyclic alkyl 4-pyrimidones |
| US4154834A (en) * | 1975-12-29 | 1979-05-15 | Smith Kline & French Laboratories Limited | Substituted isocytosines having histamine H2 -antagonist activity |
| MW5076A1 (en) * | 1975-12-29 | 1978-02-08 | Smith Kline French Lab | Pharmacologicalle active compounds |
| US4227000A (en) * | 1978-04-11 | 1980-10-07 | Smith Kline & French Laboratories Limited | Intermediates in the process for making histamine antagonists |
| PT69886A (en) * | 1978-07-15 | 1979-08-01 | Smith Kline French Lab | Process for preparing isoureas and isothioureas |
-
1979
- 1979-04-04 IL IL57005A patent/IL57005A/xx unknown
- 1979-04-04 AU AU45714/79A patent/AU527202B2/en not_active Ceased
- 1979-04-04 PH PH22351A patent/PH16240A/en unknown
- 1979-04-05 GR GR58804A patent/GR66986B/el unknown
- 1979-04-05 ZA ZA791616A patent/ZA791616B/xx unknown
- 1979-04-05 JP JP4187679A patent/JPS54138580A/ja active Pending
- 1979-04-06 FI FI791143A patent/FI791143A7/fi not_active Application Discontinuation
- 1979-04-06 NZ NZ190122A patent/NZ190122A/xx unknown
- 1979-04-09 DK DK147379A patent/DK147379A/da not_active IP Right Cessation
- 1979-04-09 CA CA000325179A patent/CA1138453A/en not_active Expired
- 1979-04-09 IE IE364/79A patent/IE48080B1/en unknown
- 1979-04-09 RO RO7997173A patent/RO76810A/ro unknown
- 1979-04-09 IT IT67751/79A patent/IT1118476B/it active
- 1979-04-09 HU HU79SI1685A patent/HU180081B/hu unknown
- 1979-04-10 DD DD79212128A patent/DD142878A5/de unknown
- 1979-04-10 CS CS792440A patent/CS210684B2/cs unknown
- 1979-04-10 PL PL1979214792A patent/PL118404B1/pl unknown
- 1979-04-10 SU SU792747652A patent/SU944504A3/ru active
- 1979-04-10 NO NO791225A patent/NO791225L/no unknown
- 1979-04-10 YU YU00841/79A patent/YU84179A/xx unknown
- 1979-04-10 AT AT0267079A patent/AT372956B/de not_active IP Right Cessation
- 1979-04-10 PL PL1979224350A patent/PL117998B1/pl unknown
- 1979-04-10 KR KR7901119A patent/KR820002136B1/ko not_active Expired
- 1979-04-10 PT PT69464A patent/PT69464A/pt unknown
- 1979-04-10 ES ES479469A patent/ES479469A1/es not_active Expired
- 1979-04-10 MX MX797862U patent/MX5898E/es unknown
- 1979-04-11 CY CY1194A patent/CY1194A/xx unknown
- 1979-04-11 EP EP79300598A patent/EP0004793B1/en not_active Expired
- 1979-04-11 DE DE7979300598T patent/DE2961652D1/de not_active Expired
-
1980
- 1980-05-19 US US06/151,502 patent/US4523015A/en not_active Expired - Lifetime
- 1980-06-11 SU SU802932201A patent/SU906376A3/ru active
- 1980-06-27 PH PH24208A patent/PH16841A/en unknown
-
1983
- 1983-04-30 KE KE3284A patent/KE3284A/xx unknown
-
1985
- 1985-12-30 MY MY703/85A patent/MY8500703A/xx unknown
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