DE2854115C2 - - Google Patents
Info
- Publication number
- DE2854115C2 DE2854115C2 DE2854115A DE2854115A DE2854115C2 DE 2854115 C2 DE2854115 C2 DE 2854115C2 DE 2854115 A DE2854115 A DE 2854115A DE 2854115 A DE2854115 A DE 2854115A DE 2854115 C2 DE2854115 C2 DE 2854115C2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- tetrahydro
- pyrimidine
- pyrido
- oxo
- 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
- 150000001875 compounds Chemical class 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- -1 4-ethoxyphenyl Chemical group 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- ZEKGTEVPPLLXID-UHFFFAOYSA-N 6-methyl-4-oxo-9-(phenylhydrazinylidene)-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C12=NC=C(C(O)=O)C(=O)N2C(C)CCC1=NNC1=CC=CC=C1 ZEKGTEVPPLLXID-UHFFFAOYSA-N 0.000 claims description 10
- 239000012954 diazonium Substances 0.000 claims description 9
- 150000001989 diazonium salts Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 claims description 2
- AMJPCENKPJCONE-UHFFFAOYSA-N 6-methyl-4-oxo-9-(pyridin-3-ylhydrazinylidene)-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C12=NC=C(C(O)=O)C(=O)N2C(C)CCC1=NNC1=CC=CN=C1 AMJPCENKPJCONE-UHFFFAOYSA-N 0.000 claims description 2
- RLPJAJZPUGSOBN-UHFFFAOYSA-N 9-[(4-ethoxyphenyl)hydrazinylidene]-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1NN=C1C2=NC=C(C(O)=O)C(=O)N2C(C)CC1 RLPJAJZPUGSOBN-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- UBOXAHWUKQXQEH-UHFFFAOYSA-N 2,3,4,6-tetrahydro-1h-pyrido[1,2-a]pyrimidine Chemical class C1=CCN2CCCNC2=C1 UBOXAHWUKQXQEH-UHFFFAOYSA-N 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- WUHFIBQMXMWMIL-UHFFFAOYSA-N 6-methyl-9-[(3-methylphenyl)hydrazinylidene]-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C12=NC=C(C(O)=O)C(=O)N2C(C)CCC1=NNC1=CC=CC(C)=C1 WUHFIBQMXMWMIL-UHFFFAOYSA-N 0.000 claims 1
- ILNPGJSJTXECRO-UHFFFAOYSA-N 6-methyl-9-[(3-nitrophenyl)hydrazinylidene]-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C12=NC=C(C(O)=O)C(=O)N2C(C)CCC1=NNC1=CC=CC([N+]([O-])=O)=C1 ILNPGJSJTXECRO-UHFFFAOYSA-N 0.000 claims 1
- MFGXELBBSOGAKT-UHFFFAOYSA-N 9-[(3,4-dichlorophenyl)hydrazinylidene]-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C12=NC=C(C(O)=O)C(=O)N2C(C)CCC1=NNC1=CC=C(Cl)C(Cl)=C1 MFGXELBBSOGAKT-UHFFFAOYSA-N 0.000 claims 1
- CBYYHIDLDPBPKE-UHFFFAOYSA-N 9-[(3-chlorophenyl)hydrazinylidene]-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C12=NC=C(C(O)=O)C(=O)N2C(C)CCC1=NNC1=CC=CC(Cl)=C1 CBYYHIDLDPBPKE-UHFFFAOYSA-N 0.000 claims 1
- PCHABWHZLMMXNN-UHFFFAOYSA-N 9-[(4-carboxyphenyl)hydrazinylidene]-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C12=NC=C(C(O)=O)C(=O)N2C(C)CCC1=NNC1=CC=C(C(O)=O)C=C1 PCHABWHZLMMXNN-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000000155 melt Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 230000008018 melting Effects 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000013078 crystal Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 10
- 239000001632 sodium acetate Substances 0.000 description 10
- 235000017281 sodium acetate Nutrition 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 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 5
- 208000006673 asthma Diseases 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- SJSZYLDJHZWMGY-UHFFFAOYSA-N 9-[(4-chlorophenyl)hydrazinylidene]-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C12=NC=C(C(O)=O)C(=O)N2C(C)CCC1=NNC1=CC=C(Cl)C=C1 SJSZYLDJHZWMGY-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 4
- 229940067157 phenylhydrazine Drugs 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- VFMCUTPRJLZEEW-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine Chemical class C1=CC=CN2CC=CN=C21 VFMCUTPRJLZEEW-UHFFFAOYSA-N 0.000 description 3
- KOXNRJHZWXSKMF-UHFFFAOYSA-N 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C(C)CCCC2=N1 KOXNRJHZWXSKMF-UHFFFAOYSA-N 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 208000026935 allergic disease Diseases 0.000 description 3
- 230000007815 allergy Effects 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- FAMLIVWZCSKDKB-UHFFFAOYSA-N ethyl 6-methyl-4-oxo-9-(phenylhydrazinylidene)-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C1CC(C)N2C(=O)C(C(=O)OCC)=CN=C2C1=NNC1=CC=CC=C1 FAMLIVWZCSKDKB-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- SWHJKRHVNLCDSX-UHFFFAOYSA-N 9-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C(C)CCC(Br)C2=N1 SWHJKRHVNLCDSX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- NIDCZHYTEWBSKT-UHFFFAOYSA-N ethyl 4H-pyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C1=CC=CN2CC(C(=O)OCC)=CN=C21 NIDCZHYTEWBSKT-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000008101 lactose Substances 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
- 239000000463 material Substances 0.000 description 2
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
- BZGLCXAARJPJGG-UHFFFAOYSA-N 4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1CCCN2C(=O)C(C(=O)O)=CN=C21 BZGLCXAARJPJGG-UHFFFAOYSA-N 0.000 description 1
- CLKCOOGQYKTQAV-UHFFFAOYSA-N 6-[3-(2-carboxy-4-oxochromen-6-yl)oxy-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=CC(OCC(COC=3C=C4C(=O)C=C(OC4=CC=3)C(O)=O)O)=CC=C21 CLKCOOGQYKTQAV-UHFFFAOYSA-N 0.000 description 1
- HCJOGZBBWGQKGC-UHFFFAOYSA-N 6-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC(=O)N2C(C)CCCC2=N1 HCJOGZBBWGQKGC-UHFFFAOYSA-N 0.000 description 1
- MCWSWZXZJSEYCI-UHFFFAOYSA-N 6-methyl-9-(phenylhydrazinylidene)-7,8-dihydro-6h-pyrido[1,2-a]pyrimidin-4-one Chemical compound C12=NC=CC(=O)N2C(C)CCC1=NNC1=CC=CC=C1 MCWSWZXZJSEYCI-UHFFFAOYSA-N 0.000 description 1
- HLVACOKQXMSDTJ-UHFFFAOYSA-N 9-[(2-carboxyphenyl)hydrazinylidene]-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C12=NC=C(C(O)=O)C(=O)N2C(C)CCC1=NNC1=CC=CC=C1C(O)=O HLVACOKQXMSDTJ-UHFFFAOYSA-N 0.000 description 1
- WTDCNSKHMYISGQ-UHFFFAOYSA-N 9-[(4-bromophenyl)hydrazinylidene]-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C12=NC=C(C(O)=O)C(=O)N2C(C)CCC1=NNC1=CC=C(Br)C=C1 WTDCNSKHMYISGQ-UHFFFAOYSA-N 0.000 description 1
- YPEWAVQABSGNSF-UHFFFAOYSA-N 9-hydrazinylidene-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C(C)CCC(=NN)C2=N1 YPEWAVQABSGNSF-UHFFFAOYSA-N 0.000 description 1
- IGSIRHVRTQTZML-UHFFFAOYSA-N 9-hydroxy-6-methyl-4-oxo-6,7-dihydropyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C(C)CC=C(O)C2=N1 IGSIRHVRTQTZML-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
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- OKISNMVICVPGFK-UHFFFAOYSA-N ethyl 6-methyl-9-[(3-methylphenyl)hydrazinylidene]-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C1CC(C)N2C(=O)C(C(=O)OCC)=CN=C2C1=NNC1=CC=CC(C)=C1 OKISNMVICVPGFK-UHFFFAOYSA-N 0.000 description 1
- VWNIRKGKNLYCTM-UHFFFAOYSA-N ethyl 9-[(4-bromophenyl)hydrazinylidene]-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C1CC(C)N2C(=O)C(C(=O)OCC)=CN=C2C1=NNC1=CC=C(Br)C=C1 VWNIRKGKNLYCTM-UHFFFAOYSA-N 0.000 description 1
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- POGCMSXFHZKUGD-UHFFFAOYSA-N ethyl 9-hydroxy-6-methyl-4-oxo-6,7-dihydropyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound OC1=CCC(C)N2C(=O)C(C(=O)OCC)=CN=C21 POGCMSXFHZKUGD-UHFFFAOYSA-N 0.000 description 1
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Oncology (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU77CI1794A HU178496B (en) | 1977-12-29 | 1977-12-29 | Process for preparing 6,7,8,9-tetrahydro-4h-pyrido/1,2-a/pyrimidine derivatives with antiallergic activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2854115A1 DE2854115A1 (de) | 1979-07-12 |
| DE2854115C2 true DE2854115C2 (en, 2012) | 1988-07-28 |
Family
ID=10994683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782854115 Granted DE2854115A1 (de) | 1977-12-29 | 1978-12-15 | Neue kondensierte pyrimidin-derivate und verfahren zu ihrer herstellung |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US4234586A (en, 2012) |
| JP (1) | JPS5495598A (en, 2012) |
| AR (3) | AR222985A1 (en, 2012) |
| AT (1) | AT375936B (en, 2012) |
| AU (1) | AU520428B2 (en, 2012) |
| BE (1) | BE873194A (en, 2012) |
| CA (1) | CA1130284A (en, 2012) |
| CH (1) | CH642078A5 (en, 2012) |
| CS (1) | CS244654B2 (en, 2012) |
| DD (1) | DD139854A5 (en, 2012) |
| DE (1) | DE2854115A1 (en, 2012) |
| DK (1) | DK157022C (en, 2012) |
| ES (7) | ES476442A1 (en, 2012) |
| FI (1) | FI66614C (en, 2012) |
| FR (1) | FR2413389A1 (en, 2012) |
| GB (1) | GB2011898B (en, 2012) |
| GR (1) | GR68357B (en, 2012) |
| HU (1) | HU178496B (en, 2012) |
| IL (1) | IL56078A (en, 2012) |
| IT (1) | IT1203210B (en, 2012) |
| LU (1) | LU80601A1 (en, 2012) |
| NL (1) | NL7812547A (en, 2012) |
| NO (1) | NO151287C (en, 2012) |
| PL (5) | PL119501B1 (en, 2012) |
| PT (1) | PT68935A (en, 2012) |
| SE (1) | SE438675B (en, 2012) |
| SU (2) | SU999972A3 (en, 2012) |
| YU (3) | YU42093B (en, 2012) |
| ZA (1) | ZA787385B (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU178496B (en) * | 1977-12-29 | 1982-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing 6,7,8,9-tetrahydro-4h-pyrido/1,2-a/pyrimidine derivatives with antiallergic activity |
| HU176942B (hu) * | 1979-05-11 | 1981-06-28 | Chinoin Gyogyszer Es Vegyeszet | Sposob poluchenija 2,3- i 3,4-dvuzamehhjonnykh tetragidro-pirrolo!1,2-a!-pirimidinov |
| HU178453B (en) * | 1979-05-11 | 1982-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 9-hydrazino-4-oxo-6,7,8,9-tetrahydro-4h-p-pyrido-square bracket-1,2-a-square bracket closed-pyrimidine derivatives |
| US4482557A (en) * | 1979-05-11 | 1984-11-13 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | 3-Substituted-2-oxo-tetrahydro-pyrrol[1,2-a]pyrimidines having digitalis-like activity |
| HU179443B (en) * | 1979-05-11 | 1982-10-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing substituted geminal dihalogeno-derivatives of pyrido-square bracket-1,2-a-square closed-pyrimidines,pyrrolo-square bracket-1,2-a-square bracket closed-pyrimidines and pyrimido-square bracket-1,2,-a-square bracket closed-asepines |
| HU178452B (en) * | 1979-05-11 | 1982-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing 9-substituted amino-4-oxo-6,7-dihydro-4h-pyrido/1,2-a/pyrimidine derivatives |
| HU183173B (en) * | 1980-06-24 | 1984-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 6-hydrazono-pyrido-aracket-2,1-b-bracket closed-quinazolin-11-ones |
| AT381093B (de) * | 1980-06-24 | 1986-08-25 | Chinoin Gyogyszer Es Vegyeszet | Verfahren zur herstellung neuer 6-hydrazono-pyrido(2,1-b)chinazolin-11-on-deriv te, von deren salzen sowie von deren stereomeren |
| HU183408B (en) | 1981-04-28 | 1984-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing oral ratard pharmaceutical compositions |
| US4395549A (en) * | 1981-10-02 | 1983-07-26 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | 6-Hydrazono-pyrido[2,1-b] quinazoline-11 ones |
| US5344933A (en) * | 1991-09-11 | 1994-09-06 | Fuji Photo Film Co., Ltd. | Pyrrole ring-or condensed pyrrole ring-containing azomethine dye |
| EP1790649A1 (en) * | 2005-11-21 | 2007-05-30 | Sanofi-Aventis | Substituted bicyclic pyrimidone derivatives |
| EP2138485A1 (en) | 2008-06-26 | 2009-12-30 | sanofi-aventis | Substituted N-Oxide pyrazine derivatives |
| EP2138494A1 (en) * | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted alkyl pyrimidin-4-one derivatives |
| EP2138498A1 (en) | 2008-06-26 | 2009-12-30 | sanofi-aventis | Substituted tricyclic derivatives against neurodegenerative diseases |
| EP2138495A1 (en) | 2008-06-26 | 2009-12-30 | sanofi-aventis | Substituted pyrimido[2,1-a]isoquinolin-4-one derivatives |
| EP2138488A1 (en) | 2008-06-26 | 2009-12-30 | sanofi-aventis | 4-(pyridin-4-yl)-1H-[1,3,5]triazin-2-one derivatives as GSK3-beta inhibitors for the treatment of neurodegenerative diseases |
| EP2138493A1 (en) | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted pyrimidone derivatives |
| EP2138492A1 (en) * | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted pyrimidin-4-one derivatives |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2786056A (en) * | 1954-05-03 | 1957-03-19 | Merck & Co Inc | Acylamido-hydroxy pteridines and preparation thereof |
| US2894031A (en) * | 1958-09-16 | 1959-07-07 | Grace W R & Co | Process for cyclohexanone hydrazone hydrate |
| US3140315A (en) * | 1959-02-18 | 1964-07-07 | Bayer Ag | Alkyl-substituted hydrazines and hydrazones and process for preparation thereof |
| FR1255365A (fr) * | 1959-12-22 | 1961-03-10 | Cfmc | Nouveaux colorants basiques, leur procédé de préparation et leurs applications |
| US3141043A (en) * | 1961-03-24 | 1964-07-14 | Purdue Research Foundation | Cyclopentadienylimines, process for their production and condensation products thereof |
| CH441366A (de) * | 1961-06-09 | 1967-08-15 | Hoffmann La Roche | Verfahren zur Herstellung von substituierten Hydrazinverbindungen |
| US3417082A (en) * | 1965-08-16 | 1968-12-17 | Polaroid Corp | Novel chemical compounds and syntheses |
| AT302311B (de) * | 1966-11-02 | 1972-09-15 | Chinoin Gyogyszer Es Vegyeszet | Verfahren zur herstellung von homopyrimidazol-derivaten und deren saeureadditionssalzen und quaternaeren ammoniumsalzen |
| HU168014B (en, 2012) * | 1973-03-30 | 1976-02-28 | ||
| US4024132A (en) * | 1973-09-07 | 1977-05-17 | Ciba-Geigy Corporation | Azomethine pigments |
| HU174693B (hu) * | 1976-02-12 | 1980-03-28 | Chinoin Gyogyszer Es Vegyeszet | Sposob poluchenija kondensirovannykh proizvodnykh pirimidina |
| HU178496B (en) * | 1977-12-29 | 1982-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing 6,7,8,9-tetrahydro-4h-pyrido/1,2-a/pyrimidine derivatives with antiallergic activity |
-
1977
- 1977-12-29 HU HU77CI1794A patent/HU178496B/hu unknown
-
1978
- 1978-11-29 IL IL56078A patent/IL56078A/xx unknown
- 1978-11-29 LU LU80601A patent/LU80601A1/de unknown
- 1978-12-07 AT AT0873678A patent/AT375936B/de not_active IP Right Cessation
- 1978-12-11 US US05/967,958 patent/US4234586A/en not_active Expired - Lifetime
- 1978-12-15 DE DE19782854115 patent/DE2854115A1/de active Granted
- 1978-12-15 DD DD78209808A patent/DD139854A5/de not_active IP Right Cessation
- 1978-12-18 AU AU42627/78A patent/AU520428B2/en not_active Expired
- 1978-12-18 YU YU2964/78A patent/YU42093B/xx unknown
- 1978-12-19 PT PT68935A patent/PT68935A/pt unknown
- 1978-12-21 SE SE7813226A patent/SE438675B/sv not_active IP Right Cessation
- 1978-12-22 GR GR57971A patent/GR68357B/el unknown
- 1978-12-22 IT IT69933/78A patent/IT1203210B/it active
- 1978-12-27 FR FR7836461A patent/FR2413389A1/fr active Granted
- 1978-12-27 NL NL7812547A patent/NL7812547A/xx not_active Application Discontinuation
- 1978-12-28 CS CS789091A patent/CS244654B2/cs unknown
- 1978-12-28 PL PL1978223332A patent/PL119501B1/pl unknown
- 1978-12-28 PL PL1978223329A patent/PL125321B1/pl unknown
- 1978-12-28 DK DK585578A patent/DK157022C/da not_active IP Right Cessation
- 1978-12-28 AR AR274986A patent/AR222985A1/es active
- 1978-12-28 SU SU782704252A patent/SU999972A3/ru active
- 1978-12-28 PL PL1978223330A patent/PL119520B1/pl unknown
- 1978-12-28 PL PL1978223331A patent/PL119641B1/pl unknown
- 1978-12-28 ZA ZA787385A patent/ZA787385B/xx unknown
- 1978-12-28 GB GB7850110A patent/GB2011898B/en not_active Expired
- 1978-12-28 ES ES476442A patent/ES476442A1/es not_active Expired
- 1978-12-28 NO NO784393A patent/NO151287C/no unknown
- 1978-12-28 JP JP16456378A patent/JPS5495598A/ja active Granted
- 1978-12-28 PL PL1978212212A patent/PL122965B1/pl unknown
- 1978-12-28 FI FI794013A patent/FI66614C/fi not_active IP Right Cessation
- 1978-12-28 CH CH1323778A patent/CH642078A5/de not_active IP Right Cessation
- 1978-12-29 CA CA318,811A patent/CA1130284A/en not_active Expired
- 1978-12-29 BE BE192659A patent/BE873194A/xx not_active IP Right Cessation
-
1979
- 1979-06-01 ES ES481744A patent/ES481744A1/es not_active Expired
- 1979-06-01 ES ES481746A patent/ES481746A1/es not_active Expired
- 1979-06-01 ES ES481745A patent/ES481745A1/es not_active Expired
- 1979-06-01 ES ES481748A patent/ES481748A1/es not_active Expired
- 1979-06-01 ES ES481747A patent/ES481747A1/es not_active Expired
- 1979-06-01 ES ES481749A patent/ES481749A1/es not_active Expired
- 1979-09-19 US US06/076,811 patent/US4461769A/en not_active Expired - Lifetime
-
1980
- 1980-03-03 AR AR280147A patent/AR228949A1/es active
- 1980-03-18 SU SU802894304A patent/SU978730A3/ru active
-
1982
- 1982-03-03 AR AR280146A patent/AR227882A1/es active
- 1982-12-17 YU YU2795/82A patent/YU42062B/xx unknown
- 1982-12-17 YU YU2796/82A patent/YU41538B/xx unknown
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