CA1067076A - Pyrimidone derivatives - Google Patents
Pyrimidone derivativesInfo
- Publication number
- CA1067076A CA1067076A CA262,162A CA262162A CA1067076A CA 1067076 A CA1067076 A CA 1067076A CA 262162 A CA262162 A CA 262162A CA 1067076 A CA1067076 A CA 1067076A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- pyrimidone
- imidazolylmethylthio
- ethylamino
- methylthio
- 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
- 150000008318 pyrimidones Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 239000000460 chlorine Substances 0.000 claims abstract description 42
- -1 4-imidazolyl ring Chemical group 0.000 claims abstract description 35
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 32
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000005864 Sulphur Substances 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000001301 oxygen Substances 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims abstract description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims abstract description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims abstract description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims abstract description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 4
- 125000005059 halophenyl group Chemical group 0.000 claims abstract description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 80
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 60
- JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 8
- HOYGMPDDEVYMNG-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-methylsulfanyl-1h-pyrimidin-6-one Chemical compound O=C1NC(SC)=NC=C1CC1=CC=C(Cl)C=C1 HOYGMPDDEVYMNG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- VBVNMLHEJMCIGQ-UHFFFAOYSA-N 2-methylsulfanyl-5-[(3-phenylmethoxyphenyl)methyl]-1h-pyrimidin-6-one Chemical compound O=C1NC(SC)=NC=C1CC1=CC=CC(OCC=2C=CC=CC=2)=C1 VBVNMLHEJMCIGQ-UHFFFAOYSA-N 0.000 claims description 3
- RXBPYORYAKTOPL-UHFFFAOYSA-N 2-methylsulfanyl-5-phenylmethoxy-1h-pyrimidin-6-one Chemical compound O=C1NC(SC)=NC=C1OCC1=CC=CC=C1 RXBPYORYAKTOPL-UHFFFAOYSA-N 0.000 claims description 3
- DQHPVDXKVZOSJI-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-6-methyl-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-1h-pyrimidin-4-one Chemical compound N1C=NC(CSCCNC=2NC(C)=C(CC=3C=CC(Cl)=CC=3)C(=O)N=2)=C1C DQHPVDXKVZOSJI-UHFFFAOYSA-N 0.000 claims description 3
- ABFXFVHLYUMNFD-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-6-methyl-2-methylsulfanyl-1h-pyrimidin-4-one Chemical compound N1C(SC)=NC(=O)C(CC=2C=CC(Cl)=CC=2)=C1C ABFXFVHLYUMNFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- WAIHMWWSWLOHNH-UHFFFAOYSA-N 2-(1,3-thiazol-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=NC=CS1 WAIHMWWSWLOHNH-UHFFFAOYSA-N 0.000 claims description 2
- UMCHIQCDVOOJLO-UHFFFAOYSA-N 2-[(3-bromopyridin-2-yl)methylsulfanyl]ethanamine Chemical compound NCCSCC1=NC=CC=C1Br UMCHIQCDVOOJLO-UHFFFAOYSA-N 0.000 claims description 2
- ZGKIBBHQPBJPNS-UHFFFAOYSA-N 2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-5-(2-phenylethyl)-1h-pyrimidin-6-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(CCC=3C=CC=CC=3)=CN=2)=C1C ZGKIBBHQPBJPNS-UHFFFAOYSA-N 0.000 claims description 2
- VKVZRJQBZJLLFO-UHFFFAOYSA-N 2-methylsulfanyl-5-(2-phenylethyl)-1h-pyrimidin-6-one Chemical compound O=C1NC(SC)=NC=C1CCC1=CC=CC=C1 VKVZRJQBZJLLFO-UHFFFAOYSA-N 0.000 claims description 2
- FMOROLBETGGWHJ-UHFFFAOYSA-N 2-methylsulfanyl-5-(4-phenylbutyl)-1h-pyrimidin-6-one Chemical compound O=C1NC(SC)=NC=C1CCCCC1=CC=CC=C1 FMOROLBETGGWHJ-UHFFFAOYSA-N 0.000 claims description 2
- DXJKTGCPNFLRRR-UHFFFAOYSA-N 2-methylsulfanyl-5-(naphthalen-1-ylmethyl)-1h-pyrimidin-6-one Chemical compound O=C1NC(SC)=NC=C1CC1=CC=CC2=CC=CC=C12 DXJKTGCPNFLRRR-UHFFFAOYSA-N 0.000 claims description 2
- KTXBMRWMKZZVKR-UHFFFAOYSA-N 5-[(3-chlorophenyl)methyl]-2-methylsulfanyl-1h-pyrimidin-6-one Chemical compound O=C1NC(SC)=NC=C1CC1=CC=CC(Cl)=C1 KTXBMRWMKZZVKR-UHFFFAOYSA-N 0.000 claims description 2
- GTNLXXHQMVTSHZ-UHFFFAOYSA-N 5-[(3-ethoxyphenyl)methyl]-2-methylsulfanyl-1h-pyrimidin-6-one Chemical compound CCOC1=CC=CC(CC=2C(NC(SC)=NC=2)=O)=C1 GTNLXXHQMVTSHZ-UHFFFAOYSA-N 0.000 claims description 2
- IHSROGNPBGFSLC-UHFFFAOYSA-N 5-[(3-methoxyphenyl)methyl]-2-methylsulfanyl-1h-pyrimidin-6-one Chemical compound COC1=CC=CC(CC=2C(NC(SC)=NC=2)=O)=C1 IHSROGNPBGFSLC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 19
- MDDICDJQBIAKRX-UHFFFAOYSA-N 2-[2-[(3-bromopyridin-2-yl)methylsulfanyl]ethylamino]-5-[(4-chlorophenyl)methyl]-1h-pyrimidin-6-one Chemical compound C1=CC(Cl)=CC=C1CC(C(N1)=O)=CN=C1NCCSCC1=NC=CC=C1Br MDDICDJQBIAKRX-UHFFFAOYSA-N 0.000 claims 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 2
- PHZPSDULXRSXFI-UHFFFAOYSA-N 2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-5-[(3-phenylmethoxyphenyl)methyl]-1h-pyrimidin-6-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(CC=3C=C(OCC=4C=CC=CC=4)C=CC=3)=CN=2)=C1C PHZPSDULXRSXFI-UHFFFAOYSA-N 0.000 claims 2
- KZRDYATZZKOOQF-UHFFFAOYSA-N 2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-5-[(4-methylphenyl)methyl]-1h-pyrimidin-6-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(CC=3C=CC(C)=CC=3)=CN=2)=C1C KZRDYATZZKOOQF-UHFFFAOYSA-N 0.000 claims 2
- AXMLFKJUGQGZOK-UHFFFAOYSA-N 2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-5-phenylmethoxy-1h-pyrimidin-6-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(OCC=3C=CC=CC=3)=CN=2)=C1C AXMLFKJUGQGZOK-UHFFFAOYSA-N 0.000 claims 2
- SIVWLUFYWRVRQE-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-1h-pyrimidin-6-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(CC=3C(=CC=CC=3)Cl)=CN=2)=C1C SIVWLUFYWRVRQE-UHFFFAOYSA-N 0.000 claims 2
- YBPTXEPCYHJQMC-UHFFFAOYSA-N 5-[(3,4-dichlorophenyl)methyl]-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-1h-pyrimidin-6-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(CC=3C=C(Cl)C(Cl)=CC=3)=CN=2)=C1C YBPTXEPCYHJQMC-UHFFFAOYSA-N 0.000 claims 2
- LHFGZPDWQWNSKZ-UHFFFAOYSA-N 5-[(3-ethoxyphenyl)methyl]-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-1h-pyrimidin-6-one Chemical compound CCOC1=CC=CC(CC=2C(NC(NCCSCC3=C(NC=N3)C)=NC=2)=O)=C1 LHFGZPDWQWNSKZ-UHFFFAOYSA-N 0.000 claims 2
- UZTPZQXBCNKILU-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-1h-pyrimidin-6-one Chemical compound C1=CC(OC)=CC=C1CC(C(N1)=O)=CN=C1NCCSCC1=C(C)NC=N1 UZTPZQXBCNKILU-UHFFFAOYSA-N 0.000 claims 2
- ISOHEFMRNLGBQV-UHFFFAOYSA-N 6-methyl-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-5-(2-phenylethyl)-1h-pyrimidin-4-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(CCC=3C=CC=CC=3)=C(C)N=2)=C1C ISOHEFMRNLGBQV-UHFFFAOYSA-N 0.000 claims 2
- WWFVVDBZWDZCCL-UHFFFAOYSA-N 2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-5-(4-phenylbutyl)-1h-pyrimidin-6-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(CCCCC=3C=CC=CC=3)=CN=2)=C1C WWFVVDBZWDZCCL-UHFFFAOYSA-N 0.000 claims 1
- UGYXPZQILZRKJJ-UHFFFAOYSA-N 4-methylhistamine Chemical compound CC=1NC=NC=1CCN UGYXPZQILZRKJJ-UHFFFAOYSA-N 0.000 claims 1
- CUDPTJIZUFTCSL-UHFFFAOYSA-N 5-[(3,4-dichlorophenyl)methyl]-2-methylsulfanyl-1h-pyrimidin-6-one Chemical compound O=C1NC(SC)=NC=C1CC1=CC=C(Cl)C(Cl)=C1 CUDPTJIZUFTCSL-UHFFFAOYSA-N 0.000 claims 1
- OFXHMXUEFVAZRT-UHFFFAOYSA-N 5-[(3-chlorophenyl)methyl]-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-1h-pyrimidin-6-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(CC=3C=C(Cl)C=CC=3)=CN=2)=C1C OFXHMXUEFVAZRT-UHFFFAOYSA-N 0.000 claims 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 claims 1
- CIISJDOKGZADRN-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethylamino]-1h-pyrimidin-6-one Chemical compound C1=CC(Cl)=CC=C1CC(C(N1)=O)=CN=C1NCCSCC1=NC=CS1 CIISJDOKGZADRN-UHFFFAOYSA-N 0.000 claims 1
- CKTMYAZYNITXCM-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-1h-pyrimidin-6-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(CC=3C=CC(Cl)=CC=3)=CN=2)=C1C CKTMYAZYNITXCM-UHFFFAOYSA-N 0.000 claims 1
- LYTMGJCSPRGACH-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]-2-methylsulfanyl-1h-pyrimidin-6-one Chemical compound C1=CC(OC)=CC=C1CC1=CN=C(SC)NC1=O LYTMGJCSPRGACH-UHFFFAOYSA-N 0.000 claims 1
- PBIQRBBUIDCZBF-UHFFFAOYSA-N 5-[(4-methylphenyl)methyl]-2-methylsulfanyl-1h-pyrimidin-6-one Chemical compound O=C1NC(SC)=NC=C1CC1=CC=C(C)C=C1 PBIQRBBUIDCZBF-UHFFFAOYSA-N 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
- 239000000938 histamine H1 antagonist Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 229960001340 histamine Drugs 0.000 description 19
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 16
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 16
- JUOJPKSDUODKRD-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]-2-[2-(1,2-thiazol-3-ylmethylsulfanyl)ethylamino]-1h-pyrimidin-6-one Chemical compound C1=CC(OC)=CC=C1CC(C(N1)=O)=CN=C1NCCSCC1=NSC=C1 JUOJPKSDUODKRD-UHFFFAOYSA-N 0.000 description 13
- 238000006467 substitution reaction Methods 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- REWSTMMSWDVLAL-UHFFFAOYSA-N 2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-5-[(4-phenylphenyl)methyl]-1h-pyrimidin-6-one Chemical compound N1C=NC(CSCCNC=2NC(=O)C(CC=3C=CC(=CC=3)C=3C=CC=CC=3)=CN=2)=C1C REWSTMMSWDVLAL-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- KQQZLHYCICBIIE-UHFFFAOYSA-N ethyl 3-(3-chlorophenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=CC(Cl)=C1 KQQZLHYCICBIIE-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- NINZPEJMYUKXQZ-UHFFFAOYSA-N 2-[2-[(3-hydroxypyridin-2-yl)methylsulfanyl]ethylamino]-5-[(4-methoxyphenyl)methyl]-1h-pyrimidin-6-one Chemical compound C1=CC(OC)=CC=C1CC(C(N1)=O)=CN=C1NCCSCC1=NC=CC=C1O NINZPEJMYUKXQZ-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- QEGNHHZXRNZTSA-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]-2-[2-(1,2,5-thiadiazol-3-ylmethylsulfanyl)ethylamino]-1h-pyrimidin-6-one Chemical compound C1=CC(OC)=CC=C1CC(C(N1)=O)=CN=C1NCCSCC1=NSN=C1 QEGNHHZXRNZTSA-UHFFFAOYSA-N 0.000 description 4
- ARFWOOGDGPGDIA-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]-2-[2-[(3-methoxypyridin-2-yl)methylsulfanyl]ethylamino]-1h-pyrimidin-6-one Chemical compound C1=CC(OC)=CC=C1CC(C(N1)=O)=CN=C1NCCSCC1=NC=CC=C1OC ARFWOOGDGPGDIA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- UYHSQVMHSFXUOA-UHFFFAOYSA-N 2-methylthiouracil Chemical compound CSC1=NC=CC(O)=N1 UYHSQVMHSFXUOA-UHFFFAOYSA-N 0.000 description 3
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 3
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 3
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 3
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- KPQBDHIUPYNYRT-UHFFFAOYSA-N ethyl 3-(4-phenoxyphenyl)propanoate Chemical compound C1=CC(CCC(=O)OCC)=CC=C1OC1=CC=CC=C1 KPQBDHIUPYNYRT-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 1
- RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 1
- 229960003291 chlorphenamine Drugs 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- TWJIIGRWKGEQHW-UHFFFAOYSA-N ethyl 2-(3-phenylpropoxy)acetate Chemical compound CCOC(=O)COCCCC1=CC=CC=C1 TWJIIGRWKGEQHW-UHFFFAOYSA-N 0.000 description 1
- AYBWQZGGKFGQLB-UHFFFAOYSA-N ethyl 3-(3,4,5-trimethoxyphenyl)propanoate Chemical class CCOC(=O)CCC1=CC(OC)=C(OC)C(OC)=C1 AYBWQZGGKFGQLB-UHFFFAOYSA-N 0.000 description 1
- SIKDERRNURRWRR-UHFFFAOYSA-N ethyl 3-(3,4-dichlorophenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=C(Cl)C(Cl)=C1 SIKDERRNURRWRR-UHFFFAOYSA-N 0.000 description 1
- XIWUTAAOMFFHTR-UHFFFAOYSA-N ethyl 3-(3-bromophenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=CC(Br)=C1 XIWUTAAOMFFHTR-UHFFFAOYSA-N 0.000 description 1
- ZECGNJSXCCKHDX-UHFFFAOYSA-N ethyl 3-(3-hydroxyphenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=CC(O)=C1 ZECGNJSXCCKHDX-UHFFFAOYSA-N 0.000 description 1
- CDOMXVVPMVTUNT-UHFFFAOYSA-N ethyl 3-(4-phenylphenyl)propanoate Chemical compound C1=CC(CCC(=O)OCC)=CC=C1C1=CC=CC=C1 CDOMXVVPMVTUNT-UHFFFAOYSA-N 0.000 description 1
- ROZIBPRZZDKLBP-UHFFFAOYSA-N ethyl 3-[4-(4-methoxyphenyl)phenyl]propanoate Chemical compound C1=CC(CCC(=O)OCC)=CC=C1C1=CC=C(OC)C=C1 ROZIBPRZZDKLBP-UHFFFAOYSA-N 0.000 description 1
- BXSIHFSJIKHCNZ-UHFFFAOYSA-N ethyl 3-naphthalen-2-ylpropanoate Chemical compound C1=CC=CC2=CC(CCC(=O)OCC)=CC=C21 BXSIHFSJIKHCNZ-UHFFFAOYSA-N 0.000 description 1
- KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 1
- AYPJVXQBVHCUCJ-UHFFFAOYSA-N ethyl 4-hydroxybutanoate Chemical compound CCOC(=O)CCCO AYPJVXQBVHCUCJ-UHFFFAOYSA-N 0.000 description 1
- RSHBWABGLCPUJJ-UHFFFAOYSA-N ethyl 4-phenylmethoxybutanoate Chemical compound CCOC(=O)CCCOCC1=CC=CC=C1 RSHBWABGLCPUJJ-UHFFFAOYSA-N 0.000 description 1
- SKCHNHKFQWMLLJ-UHFFFAOYSA-N ethyl 6-phenylhexanoate Chemical compound CCOC(=O)CCCCCC1=CC=CC=C1 SKCHNHKFQWMLLJ-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940041476 lactose 100 mg Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KBWFHQOKZPEFIU-UHFFFAOYSA-N n-butyl-2-(dimethylamino)-n-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)propanamide Chemical compound O=C1C(N(C(=O)C(C)N(C)C)CCCC)=C(C)N(C)N1C1=CC=CC=C1 KBWFHQOKZPEFIU-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
- 229960000444 pentagastrin Drugs 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102200105730 rs16846624 Human genes 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- YALHCTUQSQRCSX-UHFFFAOYSA-N sulfane sulfuric acid Chemical group S.OS(O)(=O)=O YALHCTUQSQRCSX-UHFFFAOYSA-N 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- WZMPOCLULGAHJR-UHFFFAOYSA-N thiophen-2-ol Chemical compound OC1=CC=CS1 WZMPOCLULGAHJR-UHFFFAOYSA-N 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical class O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D239/56—One oxygen atom and one sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4034175 | 1975-10-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1067076A true CA1067076A (en) | 1979-11-27 |
Family
ID=10414412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA262,162A Expired CA1067076A (en) | 1975-10-02 | 1976-09-28 | Pyrimidone derivatives |
Country Status (36)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MW5076A1 (en) * | 1975-12-29 | 1978-02-08 | Smith Kline French Lab | Pharmacologicalle active compounds |
| NZ186511A (en) | 1977-03-19 | 1980-11-14 | Smith Kline French Lab | 3-substituted alkylamino-6-substituted alkyl-1,2,4-triazin-5-ones and pharmaceutical compositions 3-substituted thio-1,2,4-triazin-5-ones |
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| GR62452B (en) | 1977-04-20 | 1979-04-12 | Ici Ltd | Preparation process of guanidine derivatives |
| JPS54104816A (en) * | 1978-01-27 | 1979-08-17 | Memorex Corp | Magnetic recorder tape reel |
| IN151188B (enrdf_load_stackoverflow) * | 1978-02-13 | 1983-03-05 | Smith Kline French Lab | |
| IL57005A (en) * | 1978-04-11 | 1983-11-30 | Smith Kline French Lab | Process for the preparation of 2-amino pyrimid-4-one derivatives and novel 2-nitroaminopyrimid-4-ones as intermediates therefor |
| ZA792608B (en) * | 1978-05-30 | 1980-06-25 | Smith Kline French Lab | Nitro compounds |
| ZA793443B (en) * | 1978-07-26 | 1980-12-31 | Glaxo Group Ltd | Heterocyclic derivatives |
| US4374836A (en) | 1978-10-16 | 1983-02-22 | Imperial Chemical Industries Ltd. | Antisecretory heterocyclic derivatives, process for their manufacture and pharmaceutical compositions containing them |
| US4496567A (en) * | 1978-11-13 | 1985-01-29 | Smith Kline & French Laboratories Limited | Phenyl alkylaminopyrimidones |
| EP0014057B1 (en) | 1979-01-18 | 1985-01-02 | Imperial Chemical Industries Plc | Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| US4521418A (en) * | 1979-02-21 | 1985-06-04 | Smith Kline & French Laboratories Limited | Guanidinothiazolyl derivatives |
| JPS55145683A (en) * | 1979-04-26 | 1980-11-13 | Smith Kline French Lab | Pyrimidone derivative |
| CA1155842A (en) * | 1980-03-29 | 1983-10-25 | Thomas H. Brown | Compounds |
| ZW21281A1 (en) * | 1980-10-01 | 1981-11-18 | Smith Kline French Lab | Amine derivatives |
| IE53068B1 (en) * | 1981-06-15 | 1988-05-25 | Merck & Co Inc | Diamino isothiazole-1-oxides and -1,1-dioxides as gastic secretion inhibitors |
| PT75074B (en) * | 1981-06-27 | 1986-02-26 | Smith Kline French Lab | Process for preparing certain pyrimidone derivatives and compositions containing them |
| CA1206151A (en) * | 1981-12-28 | 1986-06-17 | Richard P. Pioch | Pyrimidone anti-ulcer agents |
| JPS5993074A (ja) * | 1982-10-01 | 1984-05-29 | スミス・クライン・アンド・フレンチ・ラボラトリ−ス・リミテツド | ピリミドン誘導体 |
| DE8309239U1 (de) * | 1983-03-29 | 1983-09-29 | Basf Ag, 6700 Ludwigshafen | Bandspule, insbesondere fuer magnetbaender |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1397436A (en) * | 1972-09-05 | 1975-06-11 | Smith Kline French Lab | Heterocyclic n-cyanoguinidines |
| GB1419994A (en) * | 1973-05-03 | 1976-01-07 | Smith Kline French Lab | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
-
1976
- 1976-09-06 IN IN1633/CAL/76A patent/IN146736B/en unknown
- 1976-09-07 NL NL7609917A patent/NL7609917A/xx unknown
- 1976-09-07 NZ NZ181959A patent/NZ181959A/xx unknown
- 1976-09-10 MW MW34/76A patent/MW3476A1/xx unknown
- 1976-09-14 ZA ZA765498A patent/ZA765498B/xx unknown
- 1976-09-14 PT PT65590A patent/PT65590B/pt unknown
- 1976-09-14 IT IT27192/76A patent/IT1070839B/it active
- 1976-09-16 IL IL50503A patent/IL50503A/xx unknown
- 1976-09-20 SE SE7610409A patent/SE431872B/xx not_active IP Right Cessation
- 1976-09-22 BE BE170830A patent/BE846452A/xx not_active IP Right Cessation
- 1976-09-24 AT AT711976A patent/AT358045B/de not_active IP Right Cessation
- 1976-09-24 PH PH18943A patent/PH13921A/en unknown
- 1976-09-24 FR FR7628824A patent/FR2326192A1/fr active Granted
- 1976-09-27 CS CS766222A patent/CS203003B2/cs unknown
- 1976-09-28 DE DE2643670A patent/DE2643670C2/de not_active Expired
- 1976-09-28 CA CA262,162A patent/CA1067076A/en not_active Expired
- 1976-09-28 YU YU02372/76A patent/YU237276A/xx unknown
- 1976-09-28 GR GR51794A patent/GR61307B/el unknown
- 1976-09-29 IE IE2154/76A patent/IE44845B1/en unknown
- 1976-09-29 OA OA55946A patent/OA05445A/xx unknown
- 1976-09-30 AU AU18295/76A patent/AU504897B2/en not_active Expired
- 1976-09-30 DD DD195067A patent/DD126563A5/xx unknown
- 1976-09-30 AR AR264926A patent/AR221682A1/es active
- 1976-10-01 MX MX764951U patent/MX4614E/es unknown
- 1976-10-01 ZM ZM121/76A patent/ZM12176A1/xx unknown
- 1976-10-01 HU HU76SI1543A patent/HU175537B/hu unknown
- 1976-10-01 FI FI762803A patent/FI61701C/fi not_active IP Right Cessation
- 1976-10-01 DK DK442476A patent/DK442476A/da not_active Application Discontinuation
- 1976-10-01 LU LU75922A patent/LU75922A1/xx unknown
- 1976-10-01 JP JP51118904A patent/JPS5246087A/ja active Granted
- 1976-10-01 NO NO763371A patent/NO145792C/no unknown
- 1976-10-01 PL PL1976192809A patent/PL105828B1/pl unknown
- 1976-10-01 ES ES452060A patent/ES452060A1/es not_active Expired
- 1976-10-01 CH CH1248276A patent/CH625801A5/de not_active IP Right Cessation
- 1976-10-01 BG BG034338A patent/BG25224A3/xx unknown
- 1976-10-02 RO RO7687887A patent/RO73511A/ro unknown
-
1978
- 1978-12-11 IT IT7830708A patent/IT7830708A0/it unknown
-
1980
- 1980-12-09 JP JP55174447A patent/JPS609755B2/ja not_active Expired
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