FI63393C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla isokinolin-1(2h)-oner eller 1,6-naftyridin-5(6h)oner - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla isokinolin-1(2h)-oner eller 1,6-naftyridin-5(6h)oner Download PDFInfo
- Publication number
- FI63393C FI63393C FI773717A FI773717A FI63393C FI 63393 C FI63393 C FI 63393C FI 773717 A FI773717 A FI 773717A FI 773717 A FI773717 A FI 773717A FI 63393 C FI63393 C FI 63393C
- Authority
- FI
- Finland
- Prior art keywords
- group
- phenyl
- methyl
- carbon atoms
- methoxy
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 6
- 230000000144 pharmacologic effect Effects 0.000 title description 2
- -1 tri-substituted phenyl groups Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical class CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000002738 chelating agent Substances 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 230000008018 melting Effects 0.000 description 42
- 238000002844 melting Methods 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 40
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- FATSWWWAYBSNTI-UHFFFAOYSA-N 3-[4-(3-chloropropoxy)phenyl]-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C1=CC=C(OCCCCl)C=C1 FATSWWWAYBSNTI-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 8
- JAOQTTRURQMKBC-UHFFFAOYSA-N 6-methyl-7-[4-(oxiran-2-ylmethoxy)phenyl]-1,6-naphthyridin-5-one Chemical compound C=1C2=NC=CC=C2C(=O)N(C)C=1C(C=C1)=CC=C1OCC1CO1 JAOQTTRURQMKBC-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VPUVDEVLMMAEPO-UHFFFAOYSA-N 7-methoxy-2-methyl-3-[4-(oxiran-2-ylmethoxy)phenyl]isoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C(C=C1)=CC=C1OCC1CO1 VPUVDEVLMMAEPO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 239000012043 crude product Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- HRNUZLNPJAFQML-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-ethylethanamine Chemical compound CCNCCC1=CC=C(OC)C(OC)=C1 HRNUZLNPJAFQML-UHFFFAOYSA-N 0.000 description 2
- KCRUZAOXZRXNPB-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C1=CC=C(O)C=C1 KCRUZAOXZRXNPB-UHFFFAOYSA-N 0.000 description 2
- LABFSLVZPAFZKU-UHFFFAOYSA-N 3-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methoxyphenyl]-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C1=CC=C(OCC(O)CNC(C)C)C(OC)=C1 LABFSLVZPAFZKU-UHFFFAOYSA-N 0.000 description 2
- WVGCAXVJOIABRC-UHFFFAOYSA-N 3-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]-6,7-dimethoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C=2C=C(OC)C(OC)=CC=2C=C1C1=CC=C(OCC(O)CNC(C)C)C=C1 WVGCAXVJOIABRC-UHFFFAOYSA-N 0.000 description 2
- MZELTXWHFDTAOO-UHFFFAOYSA-N 3-[4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C1=CC=C(OCC(O)CNC(C)(C)C)C=C1 MZELTXWHFDTAOO-UHFFFAOYSA-N 0.000 description 2
- LXRMTVAVEVCSJW-UHFFFAOYSA-N 7-methoxy-3-[3-methoxy-4-(oxiran-2-ylmethoxy)phenyl]-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C(C=C1OC)=CC=C1OCC1CO1 LXRMTVAVEVCSJW-UHFFFAOYSA-N 0.000 description 2
- FZHDDLSLTKOWHS-UHFFFAOYSA-N 7-methoxy-3-[4-methoxy-2-(oxiran-2-ylmethoxy)phenyl]-2-methylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C=2N(C(=O)C3=CC(OC)=CC=C3C=2)C)C=1OCC1CO1 FZHDDLSLTKOWHS-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-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
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UWTJARDNAKLKCS-ZXVVBBHZSA-N (e)-1-(4-tert-butylphenyl)-n-[4-(naphthalen-1-ylmethyl)piperazin-1-yl]methanimine Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=N\N1CCN(CC=2C3=CC=CC=C3C=CC=2)CC1 UWTJARDNAKLKCS-ZXVVBBHZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- XGEFHNQBAUWVIP-UHFFFAOYSA-N 1-amino-3-(2-methylphenyl)propan-2-ol Chemical compound CC1=CC=CC=C1CC(O)CN XGEFHNQBAUWVIP-UHFFFAOYSA-N 0.000 description 1
- DNTKUYPEHLUNDP-UHFFFAOYSA-N 1-amino-3-(4-methylphenyl)propan-2-ol Chemical compound CC1=CC=C(CC(O)CN)C=C1 DNTKUYPEHLUNDP-UHFFFAOYSA-N 0.000 description 1
- JZEHWMUIAKALDN-UHFFFAOYSA-N 1-amino-3-phenoxypropan-2-ol Chemical compound NCC(O)COC1=CC=CC=C1 JZEHWMUIAKALDN-UHFFFAOYSA-N 0.000 description 1
- WSWPCNMLEVZGSM-UHFFFAOYSA-N 2-(2-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC=C1CCN WSWPCNMLEVZGSM-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- QZEZILFEWPZTNK-UHFFFAOYSA-N 2-methyl-3-[4-(oxiran-2-ylmethoxy)phenyl]isoquinolin-1-one Chemical compound C=1C2=CC=CC=C2C(=O)N(C)C=1C(C=C1)=CC=C1OCC1CO1 QZEZILFEWPZTNK-UHFFFAOYSA-N 0.000 description 1
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 1
- NCGAPYLHHZMWPI-UHFFFAOYSA-N 3-(4-methoxyphenoxy)propan-1-amine Chemical compound COC1=CC=C(OCCCN)C=C1 NCGAPYLHHZMWPI-UHFFFAOYSA-N 0.000 description 1
- PZGGGXIDKCBISF-UHFFFAOYSA-N 3-[2-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C1=CC=CC=C1OCC(O)CNC(C)C PZGGGXIDKCBISF-UHFFFAOYSA-N 0.000 description 1
- JULLKBIGHSEPOO-UHFFFAOYSA-N 3-[2-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]-7-methoxy-2-methylisoquinolin-1-one;oxalic acid Chemical group OC(=O)C(O)=O.CN1C(=O)C2=CC(OC)=CC=C2C=C1C1=CC=CC=C1OCC(O)CNC(C)C JULLKBIGHSEPOO-UHFFFAOYSA-N 0.000 description 1
- RVCNSMFEPRJBFL-UHFFFAOYSA-N 3-[2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methoxyphenyl]ethyl]-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1CCC1=CC=C(OCC(O)CNC(C)C)C(OC)=C1 RVCNSMFEPRJBFL-UHFFFAOYSA-N 0.000 description 1
- MTRPVYXEZIIIDL-UHFFFAOYSA-N 3-[4-[3-(2-aminoethylamino)propoxy]phenyl]-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C1=CC=C(OCCCNCCN)C=C1 MTRPVYXEZIIIDL-UHFFFAOYSA-N 0.000 description 1
- ZMKMPDAWUWBCQZ-UHFFFAOYSA-N 3-[4-[3-(3-aminopropylamino)propoxy]phenyl]-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C1=CC=C(OCCCNCCCN)C=C1 ZMKMPDAWUWBCQZ-UHFFFAOYSA-N 0.000 description 1
- YJTNGBHTJAOSOU-UHFFFAOYSA-N 3-[4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-6,7-dimethoxy-2-methylisoquinolin-1-one Chemical compound CN1C(C2=CC(=C(C=C2C=C1C1=CC=C(C=C1)OCC(CNC(C)(C)C)O)OC)OC)=O YJTNGBHTJAOSOU-UHFFFAOYSA-N 0.000 description 1
- XZSKPJOLCGWXHP-UHFFFAOYSA-N 3-[4-[3-[(2-hydroxy-2-phenylethyl)amino]propoxy]phenyl]-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C(C=C1)=CC=C1OCCCNCC(O)C1=CC=CC=C1 XZSKPJOLCGWXHP-UHFFFAOYSA-N 0.000 description 1
- CNLQFHYTARVXRI-UHFFFAOYSA-N 3-[4-[3-[(2-hydroxy-3-phenoxypropyl)amino]propoxy]phenyl]-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C(C=C1)=CC=C1OCCCNCC(O)COC1=CC=CC=C1 CNLQFHYTARVXRI-UHFFFAOYSA-N 0.000 description 1
- DJFYEZGCIAMZBO-UHFFFAOYSA-N 3-[4-[3-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]propoxy]phenyl]-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C(C=C1)=CC=C1OCCCN(C)CCC1=CC=C(OC)C(OC)=C1 DJFYEZGCIAMZBO-UHFFFAOYSA-N 0.000 description 1
- UPFBNJNYUMFBRQ-UHFFFAOYSA-N 3-[4-[3-[[2-hydroxy-3-(2-methoxyphenoxy)propyl]amino]propoxy]phenyl]-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C(C=C1)=CC=C1OCCCNCC(O)COC1=CC=CC=C1OC UPFBNJNYUMFBRQ-UHFFFAOYSA-N 0.000 description 1
- VJYGZWSJEOBCJZ-UHFFFAOYSA-N 3-[4-[3-[[2-hydroxy-3-(2-methylphenyl)propyl]amino]propoxy]phenyl]-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C(C=C1)=CC=C1OCCCNCC(O)CC1=CC=CC=C1C VJYGZWSJEOBCJZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
- NBKICXRJCSWMLW-UHFFFAOYSA-N 6,7-dimethoxy-2-methyl-3-[4-(oxiran-2-ylmethoxy)phenyl]isoquinolin-1-one Chemical compound CN1C(=O)C=2C=C(OC)C(OC)=CC=2C=C1C(C=C1)=CC=C1OCC1CO1 NBKICXRJCSWMLW-UHFFFAOYSA-N 0.000 description 1
- TUFFAFAPFQNIRB-KDZWSXRISA-N 6-[(2z,4e,6e,8e)-9-(3-chloro-1h-pyrrol-2-yl)nona-2,4,6,8-tetraen-2-yl]-4-methoxy-3-methylpyran-2-one Chemical compound O1C(=O)C(C)=C(OC)C=C1C(\C)=C/C=C/C=C/C=C/C1=C(Cl)C=CN1 TUFFAFAPFQNIRB-KDZWSXRISA-N 0.000 description 1
- IZEWFZIHQNOVKO-UHFFFAOYSA-N 7-[4-(3-chloropropoxy)phenyl]-6-methyl-1,6-naphthyridin-5-one Chemical compound C=1C2=NC=CC=C2C(=O)N(C)C=1C1=CC=C(OCCCCl)C=C1 IZEWFZIHQNOVKO-UHFFFAOYSA-N 0.000 description 1
- ABYKXBDANFLERB-UHFFFAOYSA-N 7-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]-6-methyl-1,6-naphthyridin-5-one Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1C1=CC2=NC=CC=C2C(=O)N1C ABYKXBDANFLERB-UHFFFAOYSA-N 0.000 description 1
- NOQIWIQGDYFRHY-UHFFFAOYSA-N 7-[4-[3-(diethylamino)-2-hydroxypropoxy]phenyl]-6-methyl-1,6-naphthyridin-5-one Chemical compound C1=CC(OCC(O)CN(CC)CC)=CC=C1C1=CC2=NC=CC=C2C(=O)N1C NOQIWIQGDYFRHY-UHFFFAOYSA-N 0.000 description 1
- OJHDTLPOCNVJAP-UHFFFAOYSA-N 7-[4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-6-methyl-1,6-naphthyridin-5-one Chemical compound C=1C2=NC=CC=C2C(=O)N(C)C=1C1=CC=C(OCC(O)CNC(C)(C)C)C=C1 OJHDTLPOCNVJAP-UHFFFAOYSA-N 0.000 description 1
- NPZXWJWEYAWGBH-UHFFFAOYSA-N 7-[4-[3-[2-(3,4-dimethoxyphenyl)ethylamino]-2-hydroxypropoxy]phenyl]-6-methyl-1,6-naphthyridin-5-one Chemical compound C1=C(OC)C(OC)=CC=C1CCNCC(O)COC1=CC=C(C=2N(C(=O)C3=CC=CN=C3C=2)C)C=C1 NPZXWJWEYAWGBH-UHFFFAOYSA-N 0.000 description 1
- SOUIEQFUTWLKMV-UHFFFAOYSA-N 7-methoxy-2-methyl-3-[2-(oxiran-2-ylmethoxy)phenyl]isoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C1=CC=CC=C1OCC1CO1 SOUIEQFUTWLKMV-UHFFFAOYSA-N 0.000 description 1
- ITPFDFCRQANZLK-UHFFFAOYSA-N 7-methoxy-2-methyl-3-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethyl]isoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1CCC(C=C1)=CC=C1OCC1CO1 ITPFDFCRQANZLK-UHFFFAOYSA-N 0.000 description 1
- MYVHUTHTXMFYNQ-UHFFFAOYSA-N 7-methoxy-3-[2-[3-methoxy-4-(oxiran-2-ylmethoxy)phenyl]ethyl]-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1CCC(C=C1OC)=CC=C1OCC1CO1 MYVHUTHTXMFYNQ-UHFFFAOYSA-N 0.000 description 1
- ZDKRTDBOOPMWGC-UHFFFAOYSA-N 7-methoxy-3-[4-[3-[2-(2-methoxyphenyl)ethylamino]propoxy]phenyl]-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C(C=C1)=CC=C1OCCCNCCC1=CC=CC=C1OC ZDKRTDBOOPMWGC-UHFFFAOYSA-N 0.000 description 1
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ILBOXFMTSUTUGX-UHFFFAOYSA-N CN1C(C2=CC(=CC=C2C=C1C1=CC=C(C=C1)OCC(CNCCC1=CC(=C(C=C1)OC)OC)O)OC)=O Chemical compound CN1C(C2=CC(=CC=C2C=C1C1=CC=C(C=C1)OCC(CNCCC1=CC(=C(C=C1)OC)OC)O)OC)=O ILBOXFMTSUTUGX-UHFFFAOYSA-N 0.000 description 1
- REOZKRSTFLOFPW-UHFFFAOYSA-N CN1C(C2=CC(=CC=C2C=C1C1=CC=C(C=C1)OCCCNCCC(=O)OCC(C)C)OC)=O Chemical compound CN1C(C2=CC(=CC=C2C=C1C1=CC=C(C=C1)OCCCNCCC(=O)OCC(C)C)OC)=O REOZKRSTFLOFPW-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101100244562 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) oprD gene Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 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
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 230000003257 anti-anginal effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 108700023159 delta Opioid Receptors Proteins 0.000 description 1
- 102000048124 delta Opioid Receptors Human genes 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000003184 effect on constriction Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- FIOWAHQPLXAJLP-UHFFFAOYSA-N propan-2-yl 3-[3-[4-(7-methoxy-2-methyl-1-oxoisoquinolin-3-yl)phenoxy]propylamino]propanoate Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C1=CC=C(OCCCNCCC(=O)OC(C)C)C=C1 FIOWAHQPLXAJLP-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772702600 DE2702600A1 (de) | 1977-01-22 | 1977-01-22 | Neue aminoalkoxyphenyl-derivate |
| DE2702600 | 1977-01-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI773717A7 FI773717A7 (fi) | 1978-07-23 |
| FI63393B FI63393B (fi) | 1983-02-28 |
| FI63393C true FI63393C (fi) | 1983-06-10 |
Family
ID=5999300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI773717A FI63393C (fi) | 1977-01-22 | 1977-12-09 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla isokinolin-1(2h)-oner eller 1,6-naftyridin-5(6h)oner |
Country Status (36)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3027619A1 (de) * | 1979-07-25 | 1981-02-19 | Sandoz Ag | 6-alkyl-7-phenyl-1,6-naphtyradin- 5(6h)-on-derivate |
| US4329349A (en) * | 1979-07-25 | 1982-05-11 | Sandoz, Inc. | 6-C1-4 Alkyl-7-phenyl or substituted phenyl-1,6-naphthyridine-5(6H)-ones |
| JPS59116269A (ja) * | 1982-12-24 | 1984-07-05 | Nisshin Flour Milling Co Ltd | イソカルボスチリル誘導体 |
| DE3502831A1 (de) * | 1985-01-29 | 1986-07-31 | Gödecke AG, 1000 Berlin | 1,6-naphthyridinon-derivate, verfahren zu deren herstellung und deren verwendung |
| US4698341A (en) * | 1983-07-30 | 1987-10-06 | Godecke Aktiengesellschaft | Use of 1,6-naphthyridinone derivatives in treating pulmonary thrombosis |
| DE3423003A1 (de) * | 1984-06-22 | 1986-01-02 | Beiersdorf Ag, 2000 Hamburg | Benzo(c)(1,8)naphthyridine, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen |
| JPS6136266A (ja) * | 1984-07-26 | 1986-02-20 | Mitsui Toatsu Chem Inc | イソキノリン誘導体およびそれを有効成分として含有する治療用組成物 |
| DE69531691T2 (de) * | 1994-08-04 | 2004-07-08 | C & C Research Labs | Neues amin-derivat, verfahren zur herstellung und dessen verwendung als anti-arrhythmisches mittel |
| DE19943635A1 (de) * | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| CA2569081A1 (en) * | 2004-05-31 | 2005-12-08 | Takashi Mizutani | Quinazoline derivative |
| EP2303845B1 (en) * | 2008-06-24 | 2013-09-18 | Sanofi | Bi-and polycyclic substituted isoquinoline and isoquinoline derivatives as rho kinase inhibitors |
| PT2303846E (pt) * | 2008-06-24 | 2015-09-04 | Sanofi Sa | Isoquinolinas e isoquinolinonas substituídas como inibidores de rho-quinase |
| PE20110054A1 (es) * | 2008-06-24 | 2011-02-15 | Sanofi Aventis | Isoquinolinas e isoquinolinonas 6-sustituidas |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2538341A (en) * | 1949-09-20 | 1951-01-16 | Smith Kline French Lab | Method for producing 1-hydroxyisoquinolines |
| US3432027A (en) * | 1966-01-05 | 1969-03-11 | Lily Tulip Cup Corp | Dispensing container assembly |
| GB1394700A (en) * | 1972-11-25 | 1975-05-21 | Aspro Nicholas Ltd | Pharmacologically active isoquinoline derivatives |
| AT330777B (de) * | 1973-09-08 | 1976-07-26 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen isochinolinderivaten und deren salzen |
| US3993656A (en) * | 1974-11-19 | 1976-11-23 | Merck & Co., Inc. | 1,8-Naphthyridine compounds |
| SE7603371L (sv) * | 1975-03-26 | 1976-09-27 | Sandoz Ag | Organiska foreningar, deras anvendning och framstellning |
| US4081447A (en) * | 1975-04-09 | 1978-03-28 | Abbott Laboratories | 5-[2-Hydroxy-3-(3,4-dimethoxy phenethylamino)]-propoxy-3,4-dihydro carbostyril and pharmaceutically acceptable salts thereof |
-
1977
- 1977-01-22 DE DE19772702600 patent/DE2702600A1/de not_active Ceased
- 1977-12-09 FI FI773717A patent/FI63393C/fi not_active IP Right Cessation
- 1977-12-26 BG BG038210A patent/BG28573A3/xx unknown
- 1977-12-27 ES ES465455A patent/ES465455A1/es not_active Expired
-
1978
- 1978-01-06 US US05/867,308 patent/US4154837A/en not_active Expired - Lifetime
- 1978-01-09 AT AT11078A patent/AT361480B/de not_active IP Right Cessation
- 1978-01-13 RO RO7892901A patent/RO72911A/ro unknown
- 1978-01-17 SU SU782566499A patent/SU677654A3/ru active
- 1978-01-18 CH CH52378A patent/CH640227A5/de not_active IP Right Cessation
- 1978-01-19 YU YU134/78A patent/YU40504B/xx unknown
- 1978-01-19 DD DD78203307A patent/DD135283A5/xx unknown
- 1978-01-19 CS CS78380A patent/CS195653B2/cs unknown
- 1978-01-20 NZ NZ186287A patent/NZ186287A/xx unknown
- 1978-01-20 LU LU78919A patent/LU78919A1/de unknown
- 1978-01-20 CA CA295,361A patent/CA1106846A/en not_active Expired
- 1978-01-20 IT IT47729/78A patent/IT1102816B/it active
- 1978-01-20 GR GR55214A patent/GR64093B/el unknown
- 1978-01-20 FR FR7801684A patent/FR2378014A1/fr active Granted
- 1978-01-20 AU AU32581/78A patent/AU516692B2/en not_active Expired
- 1978-01-20 PH PH20691A patent/PH13911A/en unknown
- 1978-01-20 HU HU78TO1068A patent/HU176895B/hu unknown
- 1978-01-20 ZA ZA00780365A patent/ZA78365B/xx unknown
- 1978-01-20 DK DK30578A patent/DK149847C/da not_active IP Right Cessation
- 1978-01-20 IL IL53857A patent/IL53857A/xx unknown
- 1978-01-20 JP JP514978A patent/JPS5392786A/ja active Pending
- 1978-01-20 NL NL7800717A patent/NL7800717A/xx not_active Application Discontinuation
- 1978-01-20 NO NO780214A patent/NO149502C/no unknown
- 1978-01-20 IE IE139/78A patent/IE46376B1/en unknown
- 1978-01-20 SE SE7800739A patent/SE444433B/sv not_active IP Right Cessation
- 1978-01-20 PT PT67561A patent/PT67561B/pt unknown
- 1978-01-20 BE BE184522A patent/BE863160A/xx not_active IP Right Cessation
- 1978-01-21 PL PL1978204134A patent/PL112130B1/pl unknown
- 1978-01-23 GB GB2643/78A patent/GB1568021A/en not_active Expired
-
1983
- 1983-07-19 SG SG42883A patent/SG42883G/en unknown
- 1983-11-24 HK HK600/83A patent/HK60083A/xx unknown
-
1984
- 1984-12-30 MY MY275/84A patent/MY8400275A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: DR. KARL THOMAE GMBH |