NO841780L - Fremgangsmaate for fremstilling av nye pyrimidon-derivater - Google Patents
Fremgangsmaate for fremstilling av nye pyrimidon-derivaterInfo
- Publication number
- NO841780L NO841780L NO841780A NO841780A NO841780L NO 841780 L NO841780 L NO 841780L NO 841780 A NO841780 A NO 841780A NO 841780 A NO841780 A NO 841780A NO 841780 L NO841780 L NO 841780L
- Authority
- NO
- Norway
- Prior art keywords
- dimethoxy
- pyrimido
- isoquinolin
- formula
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 3
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title 1
- -1 methylenedioxy Chemical group 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 24
- PVKCAQKXTLCSBC-UHFFFAOYSA-N 1h-isoquinolin-4-one Chemical compound C1=CC=C2C(=O)C=NCC2=C1 PVKCAQKXTLCSBC-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000008318 pyrimidones Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- ZBYXKMWAPJNVTP-KRWDZBQOSA-N (6s)-2-(2,6-dimethylanilino)-6-ethyl-9,10-dimethoxy-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C([C@@H](N1C(=O)N=2)CC)C3=CC(OC)=C(OC)C=C3C1=CC=2NC1=C(C)C=CC=C1C ZBYXKMWAPJNVTP-KRWDZBQOSA-N 0.000 claims description 3
- NKBFMQFLIHCOGI-HNNXBMFYSA-N (6s)-2-(2,6-dimethylanilino)-9,10-dimethoxy-6-methyl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound N=1C(=O)N([C@@H](C)CC=2C=C(C(=CC=22)OC)OC)C2=CC=1NC1=C(C)C=CC=C1C NKBFMQFLIHCOGI-HNNXBMFYSA-N 0.000 claims description 3
- ZPHDEHCTDNLLOW-SFHVURJKSA-N (6s)-6-ethyl-9,10-dimethoxy-2-(2,4,6-trimethylanilino)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C([C@@H](N1C(=O)N=2)CC)C3=CC(OC)=C(OC)C=C3C1=CC=2NC1=C(C)C=C(C)C=C1C ZPHDEHCTDNLLOW-SFHVURJKSA-N 0.000 claims description 3
- ULCVGPWVTYPDDM-KRWDZBQOSA-N (7r)-9,10-dimethoxy-3,7-dimethyl-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C([C@H](C)C=1C=C(C(=CC=11)OC)OC)N(C(N2C)=O)C1=CC2=NC1=C(C)C=C(C)C=C1C ULCVGPWVTYPDDM-KRWDZBQOSA-N 0.000 claims description 3
- VRDZFQAUAFYRDQ-UHFFFAOYSA-N 9,10-dimethoxy-6-methyl-2-(2,4,6-trimethylanilino)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2CC(C)N(C(N=2)=O)C1=CC=2NC1=C(C)C=C(C)C=C1C VRDZFQAUAFYRDQ-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- ZGCRHLLZAJECST-SFHVURJKSA-N (6s)-2-(2,6-dimethylphenyl)imino-6-ethyl-9,10-dimethoxy-3-methyl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C([C@@H](N1C(=O)N2C)CC)C3=CC(OC)=C(OC)C=C3C1=CC2=NC1=C(C)C=CC=C1C ZGCRHLLZAJECST-SFHVURJKSA-N 0.000 claims description 2
- RSODZRSTCNUQGQ-KRWDZBQOSA-N (6s)-9,10-dimethoxy-3,6-dimethyl-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound CN1C(=O)N([C@@H](C)CC=2C=C(C(=CC=22)OC)OC)C2=CC1=NC1=C(C)C=C(C)C=C1C RSODZRSTCNUQGQ-KRWDZBQOSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229940125898 compound 5 Drugs 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 238000010992 reflux Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004202 carbamide 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
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- CUBGKVUFGAQIFL-INIZCTEOSA-N (6s)-2-(2,6-dimethylphenyl)imino-9,10-dimethoxy-3,6-dimethyl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound CN1C(=O)N([C@@H](C)CC=2C=C(C(=CC=22)OC)OC)C2=CC1=NC1=C(C)C=CC=C1C CUBGKVUFGAQIFL-INIZCTEOSA-N 0.000 description 2
- ZAYQQSOIFXBLKS-IBGZPJMESA-N (6s)-6-ethyl-9,10-dimethoxy-3-methyl-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C([C@@H](N1C(=O)N2C)CC)C3=CC(OC)=C(OC)C=C3C1=CC2=NC1=C(C)C=C(C)C=C1C ZAYQQSOIFXBLKS-IBGZPJMESA-N 0.000 description 2
- YHEXEOXHXZWOTH-VIFPVBQESA-N 1-[(2s)-1-(3,4-dimethoxyphenyl)propan-2-yl]-1,3-diazinane-2,4,6-trione Chemical compound C1=C(OC)C(OC)=CC=C1C[C@H](C)N1C(=O)NC(=O)CC1=O YHEXEOXHXZWOTH-VIFPVBQESA-N 0.000 description 2
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- IHUBFBNARXNUEQ-UHFFFAOYSA-N 9,10-dimethoxy-7,7-dimethyl-2-(2,4,6-trimethylanilino)-6h-pyrimido[6,1-a]isoquinolin-4-one Chemical compound N=1C(=O)N2CC(C)(C)C=3C=C(OC)C(OC)=CC=3C2=CC=1NC1=C(C)C=C(C)C=C1C IHUBFBNARXNUEQ-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910001503 inorganic bromide Inorganic materials 0.000 description 2
- 229910001504 inorganic chloride Inorganic materials 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002829 nitrogen Chemical class 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KAZPHAGSWZTKDW-MRVPVSSYSA-N (2r)-1-(3,4-dimethoxyphenyl)propan-2-amine Chemical compound COC1=CC=C(C[C@@H](C)N)C=C1OC KAZPHAGSWZTKDW-MRVPVSSYSA-N 0.000 description 1
- FLPWBPAEWBUYLL-JTQLQIEISA-N (2s)-1-(3,4-dimethoxyphenyl)butan-2-amine Chemical compound CC[C@H](N)CC1=CC=C(OC)C(OC)=C1 FLPWBPAEWBUYLL-JTQLQIEISA-N 0.000 description 1
- KAZPHAGSWZTKDW-QMMMGPOBSA-N (2s)-1-(3,4-dimethoxyphenyl)propan-2-amine Chemical compound COC1=CC=C(C[C@H](C)N)C=C1OC KAZPHAGSWZTKDW-QMMMGPOBSA-N 0.000 description 1
- SZTJRKJVRLTIDX-UHFFFAOYSA-N (3,4-dimethoxyphenyl)urea Chemical compound COC1=CC=C(NC(N)=O)C=C1OC SZTJRKJVRLTIDX-UHFFFAOYSA-N 0.000 description 1
- RSODZRSTCNUQGQ-QGZVFWFLSA-N (6r)-9,10-dimethoxy-3,6-dimethyl-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound CN1C(=O)N([C@H](C)CC=2C=C(C(=CC=22)OC)OC)C2=CC1=NC1=C(C)C=C(C)C=C1C RSODZRSTCNUQGQ-QGZVFWFLSA-N 0.000 description 1
- VRDZFQAUAFYRDQ-MRXNPFEDSA-N (6r)-9,10-dimethoxy-6-methyl-2-(2,4,6-trimethylanilino)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound N=1C(=O)N([C@H](C)CC=2C=C(C(=CC=22)OC)OC)C2=CC=1NC1=C(C)C=C(C)C=C1C VRDZFQAUAFYRDQ-MRXNPFEDSA-N 0.000 description 1
- VRDZFQAUAFYRDQ-INIZCTEOSA-N (6s)-9,10-dimethoxy-6-methyl-2-(2,4,6-trimethylanilino)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound N=1C(=O)N([C@@H](C)CC=2C=C(C(=CC=22)OC)OC)C2=CC=1NC1=C(C)C=C(C)C=C1C VRDZFQAUAFYRDQ-INIZCTEOSA-N 0.000 description 1
- ULCVGPWVTYPDDM-QGZVFWFLSA-N (7s)-9,10-dimethoxy-3,7-dimethyl-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C([C@@H](C)C=1C=C(C(=CC=11)OC)OC)N(C(N2C)=O)C1=CC2=NC1=C(C)C=C(C)C=C1C ULCVGPWVTYPDDM-QGZVFWFLSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- DHLWJXGSZDJWKK-UHFFFAOYSA-N 1-(2,3-dimethoxyphenyl)propan-2-amine Chemical compound COC1=CC=CC(CC(C)N)=C1OC DHLWJXGSZDJWKK-UHFFFAOYSA-N 0.000 description 1
- FLPWBPAEWBUYLL-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)butan-2-amine Chemical compound CCC(N)CC1=CC=C(OC)C(OC)=C1 FLPWBPAEWBUYLL-UHFFFAOYSA-N 0.000 description 1
- KAZPHAGSWZTKDW-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)propan-2-amine Chemical compound COC1=CC=C(CC(C)N)C=C1OC KAZPHAGSWZTKDW-UHFFFAOYSA-N 0.000 description 1
- YXIKCDJZGLTUEO-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)propan-2-ylurea Chemical compound COC1=CC=C(CC(C)NC(N)=O)C=C1OC YXIKCDJZGLTUEO-UHFFFAOYSA-N 0.000 description 1
- YHEXEOXHXZWOTH-SECBINFHSA-N 1-[(2r)-1-(3,4-dimethoxyphenyl)propan-2-yl]-1,3-diazinane-2,4,6-trione Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H](C)N1C(=O)NC(=O)CC1=O YHEXEOXHXZWOTH-SECBINFHSA-N 0.000 description 1
- CPQKRZNVDGKMQW-UHFFFAOYSA-N 1-[2-(3,4-dimethoxyphenyl)ethyl]-5-methyl-1,3-diazinane-2,4,6-trione Chemical compound C1=C(OC)C(OC)=CC=C1CCN1C(=O)C(C)C(=O)NC1=O CPQKRZNVDGKMQW-UHFFFAOYSA-N 0.000 description 1
- RBSGPLGNQFXTEQ-UHFFFAOYSA-N 1-[3-(3,4-dimethoxyphenyl)propyl]-1,3-diazinane-2,4,6-trione Chemical compound C1=C(OC)C(OC)=CC=C1CCCN1C(=O)NC(=O)CC1=O RBSGPLGNQFXTEQ-UHFFFAOYSA-N 0.000 description 1
- BZZKABPYTXDJQF-UHFFFAOYSA-N 1-benzazepin-4-one Chemical compound O=C1C=CN=C2C=CC=CC2=C1 BZZKABPYTXDJQF-UHFFFAOYSA-N 0.000 description 1
- ZMNFJHUGGAOPNI-UHFFFAOYSA-N 10-methoxy-3,7,7-trimethyl-2-(2,4,6-trimethylphenyl)imino-6h-pyrimido[6,1-a]isoquinolin-4-one Chemical compound C=1C(OC)=CC=C(C(CN2C(=O)N3C)(C)C)C=1C2=CC3=NC1=C(C)C=C(C)C=C1C ZMNFJHUGGAOPNI-UHFFFAOYSA-N 0.000 description 1
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
- LUICYNZUMXJHFO-UHFFFAOYSA-N 2-(2,4-dimethylanilino)-9,10-dimethoxy-7-methyl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2C(C)CN(C(N=2)=O)C1=CC=2NC1=CC=C(C)C=C1C LUICYNZUMXJHFO-UHFFFAOYSA-N 0.000 description 1
- JPCCKVQVJCYNDG-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)imino-9,10-dimethoxy-3,7-dimethyl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2C(C)CN(C(N2C)=O)C1=CC2=NC1=CC=C(C)C=C1C JPCCKVQVJCYNDG-UHFFFAOYSA-N 0.000 description 1
- MDAOEGJTBPQGCB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)ethylurea Chemical compound COC1=CC=C(CCNC(N)=O)C=C1OC MDAOEGJTBPQGCB-UHFFFAOYSA-N 0.000 description 1
- KZOWYUSBBFDUDR-UHFFFAOYSA-N 2-(3,5-dimethoxyanilino)-9,10-dimethoxy-7-methyl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound COC1=CC(OC)=CC(NC2=NC(=O)N3CC(C)C4=CC(OC)=C(OC)C=C4C3=C2)=C1 KZOWYUSBBFDUDR-UHFFFAOYSA-N 0.000 description 1
- SIZKMOMFVSYOLC-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)imino-9,10-dimethoxy-3,7-dimethyl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound COC1=CC(OC)=CC(N=C2N(C(=O)N3CC(C)C4=CC(OC)=C(OC)C=C4C3=C2)C)=C1 SIZKMOMFVSYOLC-UHFFFAOYSA-N 0.000 description 1
- TWIRNJZVYLPWCN-UHFFFAOYSA-N 2-(4,5-dimethoxy-5-methylcyclohexa-1,3-dien-1-yl)ethanamine Chemical compound CC1(CC(=CC=C1OC)CCN)OC TWIRNJZVYLPWCN-UHFFFAOYSA-N 0.000 description 1
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
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- REDIVKCRDWMSQC-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)butan-2-amine Chemical compound COC1=CC=C(C(C)C(C)N)C=C1OC REDIVKCRDWMSQC-UHFFFAOYSA-N 0.000 description 1
- WYYQSKUMIFPNFW-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)propan-1-amine Chemical compound COC1=CC=C(CCCN)C=C1OC WYYQSKUMIFPNFW-UHFFFAOYSA-N 0.000 description 1
- LTWAXDIHUBZVCW-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)propylurea Chemical compound COC1=CC=C(CCCNC(N)=O)C=C1OC LTWAXDIHUBZVCW-UHFFFAOYSA-N 0.000 description 1
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- ZVPHNQYSKIGVJU-UHFFFAOYSA-N 9,10-dimethoxy-2-(4-methoxyphenyl)imino-3,7-dimethyl-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=CC(OC)=CC=C1N=C1N(C)C(=O)N2CC(C)C3=CC(OC)=C(OC)C=C3C2=C1 ZVPHNQYSKIGVJU-UHFFFAOYSA-N 0.000 description 1
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- ULCVGPWVTYPDDM-UHFFFAOYSA-N 9,10-dimethoxy-3,7-dimethyl-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2C(C)CN(C(N2C)=O)C1=CC2=NC1=C(C)C=C(C)C=C1C ULCVGPWVTYPDDM-UHFFFAOYSA-N 0.000 description 1
- HYXKTCIWUKHUBS-UHFFFAOYSA-N 9,10-dimethoxy-3,7-dimethyl-2-(3,4,5-trimethoxyphenyl)imino-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2C(C)CN(C(N2C)=O)C1=CC2=NC1=CC(OC)=C(OC)C(OC)=C1 HYXKTCIWUKHUBS-UHFFFAOYSA-N 0.000 description 1
- SFGAWJATIORJKM-UHFFFAOYSA-N 9,10-dimethoxy-7-methyl-3-propyl-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound CCCN1C(=O)N2CC(C)C3=CC(OC)=C(OC)C=C3C2=CC1=NC1=C(C)C=C(C)C=C1C SFGAWJATIORJKM-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- PKXADSMBZJCAGK-UHFFFAOYSA-N Cl.C1=CC=C2C(=O)CN=CC2=C1 Chemical compound Cl.C1=CC=C2C(=O)CN=CC2=C1 PKXADSMBZJCAGK-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 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 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- QCULXSKMELOHKV-JTQLQIEISA-N [(2s)-1-(3,4-dimethoxyphenyl)butan-2-yl]urea Chemical compound NC(=O)N[C@@H](CC)CC1=CC=C(OC)C(OC)=C1 QCULXSKMELOHKV-JTQLQIEISA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- C07D239/62—Barbituric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH244283 | 1983-05-05 | ||
| CH139284 | 1984-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO841780L true NO841780L (no) | 1984-11-06 |
Family
ID=25687524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO841780A NO841780L (no) | 1983-05-05 | 1984-05-04 | Fremgangsmaate for fremstilling av nye pyrimidon-derivater |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4581172A (fr) |
| EP (1) | EP0124893A3 (fr) |
| AU (1) | AU2751084A (fr) |
| CA (1) | CA1237429A (fr) |
| CS (1) | CS243486B2 (fr) |
| DK (1) | DK198784A (fr) |
| ES (1) | ES8505369A1 (fr) |
| FI (1) | FI841619A (fr) |
| HU (1) | HUT34025A (fr) |
| IL (1) | IL71711A (fr) |
| MC (1) | MC1600A1 (fr) |
| NO (1) | NO841780L (fr) |
| NZ (1) | NZ207981A (fr) |
| PH (1) | PH19219A (fr) |
| PT (1) | PT78549B (fr) |
| ZW (1) | ZW6284A1 (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0134984B1 (fr) * | 1983-07-16 | 1988-07-13 | Beecham Group Plc | Dérivés de la benzazépine et de la benzoxazépine |
| GB9707251D0 (en) * | 1997-04-10 | 1997-05-28 | Smithkline Beecham Plc | Novel method and compounds |
| DE60005493T2 (de) * | 1999-03-31 | 2004-07-01 | Vernalis Ltd., Wokingham | Pyrimido[6,1-a]isochinolinonderivate |
| US7169907B2 (en) * | 2002-03-01 | 2007-01-30 | Roche Diagnostics Operations, Inc. | Derivatives, immunogens, and antibodies for detecting ecstasy-class drugs |
| JP2007525475A (ja) * | 2003-07-08 | 2007-09-06 | スミスクライン・ビーチャム・コーポレイション | 新規化学化合物 |
| GB201502260D0 (en) | 2015-02-11 | 2015-04-01 | Verona Pharma Plc | Salt of Pyrimido[6,1-A]Isoquinolin-4-one compound |
| WO2017016960A1 (fr) * | 2015-07-24 | 2017-02-02 | F. Hoffmann-La Roche Ag | Procédé de préparation d'analogues de l'acide (6s)-6-alkyl-10-alcoxy-9-(alcoxy substitué)-2-oxo-6,7-dihydrobenzo[a]quinolizine-3-carboxylique |
| GB201613054D0 (en) | 2016-07-28 | 2016-09-14 | Verona Pharma Plc | New compound and process |
| AU2019302610B2 (en) | 2018-07-13 | 2023-11-23 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Fused tri-cyclic compound as PDE3/PDE4 dual inhibitor |
| US20230060174A1 (en) * | 2020-01-15 | 2023-03-02 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Pharmaceutical composition of tricyclic pde3/pde4 dual inhibitor compound |
| JP2023512471A (ja) * | 2020-01-15 | 2023-03-27 | チア タイ ティエンチン ファーマシューティカル グループ カンパニー リミテッド | Ｐｄｅ３／ｐｄｅ４二重阻害剤の結晶及びその使用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ185900A (en) * | 1976-12-10 | 1981-04-24 | Hoechst Ag | Pyrimido (6,1-a) isoquinolin-4-ones medicaments intermediate isoquinolines |
| DE2720085A1 (de) * | 1977-05-05 | 1978-11-16 | Hoechst Ag | Pyrimido(6,1-a)isochinolin-2-on- derivate |
| FI64370C (fi) * | 1977-05-05 | 1983-11-10 | Hoechst Ag | Foerfarande foer framstaellning av terapeutiskt anvaendbara pyimido-(6,1-a)isokinolin-2-imino-4-onderivat |
| DE2847693A1 (de) * | 1978-11-03 | 1980-05-22 | Hoechst Ag | Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen |
| DE3135831A1 (de) * | 1981-09-10 | 1983-04-28 | Hoechst Ag, 6230 Frankfurt | 9,10-substituierte 2-mesitylimino-3-alkyl-3,4,6,7-tetrahydro-2h-pyrimido(6,1-a)isochinolin-4-one, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
-
1984
- 1984-04-13 ZW ZW62/84A patent/ZW6284A1/xx unknown
- 1984-04-13 CA CA000451949A patent/CA1237429A/fr not_active Expired
- 1984-04-17 DK DK198784A patent/DK198784A/da not_active Application Discontinuation
- 1984-04-25 FI FI841619A patent/FI841619A/fi not_active Application Discontinuation
- 1984-04-25 US US06/603,793 patent/US4581172A/en not_active Expired - Fee Related
- 1984-04-27 NZ NZ207981A patent/NZ207981A/en unknown
- 1984-04-30 AU AU27510/84A patent/AU2751084A/en not_active Abandoned
- 1984-05-01 IL IL71711A patent/IL71711A/xx not_active IP Right Cessation
- 1984-05-02 MC MC841703A patent/MC1600A1/fr unknown
- 1984-05-02 HU HU841693A patent/HUT34025A/hu unknown
- 1984-05-02 CS CS843255A patent/CS243486B2/cs unknown
- 1984-05-04 NO NO841780A patent/NO841780L/no unknown
- 1984-05-04 PT PT78549A patent/PT78549B/pt unknown
- 1984-05-04 EP EP84105052A patent/EP0124893A3/fr not_active Withdrawn
- 1984-05-04 ES ES532172A patent/ES8505369A1/es not_active Expired
- 1984-05-04 PH PH30644A patent/PH19219A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0124893A2 (fr) | 1984-11-14 |
| US4581172A (en) | 1986-04-08 |
| HUT34025A (en) | 1985-01-28 |
| FI841619A (fi) | 1984-11-06 |
| AU2751084A (en) | 1984-11-08 |
| NZ207981A (en) | 1987-05-29 |
| PH19219A (en) | 1986-02-12 |
| MC1600A1 (fr) | 1985-05-09 |
| DK198784A (da) | 1984-11-06 |
| EP0124893A3 (fr) | 1987-11-11 |
| CS243486B2 (en) | 1986-06-12 |
| FI841619A0 (fi) | 1984-04-25 |
| CS325584A2 (en) | 1985-08-15 |
| PT78549A (en) | 1984-06-01 |
| ZW6284A1 (en) | 1985-10-30 |
| ES532172A0 (es) | 1985-06-01 |
| CA1237429A (fr) | 1988-05-31 |
| DK198784D0 (da) | 1984-04-17 |
| PT78549B (en) | 1986-09-15 |
| IL71711A (en) | 1987-08-31 |
| ES8505369A1 (es) | 1985-06-01 |
| IL71711A0 (en) | 1984-09-30 |
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