CA1077932A - Composes de la xanthine pour le traitement des bronchospasmes et des affections allergiques - Google Patents
Composes de la xanthine pour le traitement des bronchospasmes et des affections allergiquesInfo
- Publication number
- CA1077932A CA1077932A CA274,520A CA274520A CA1077932A CA 1077932 A CA1077932 A CA 1077932A CA 274520 A CA274520 A CA 274520A CA 1077932 A CA1077932 A CA 1077932A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- alkyl
- dimethyl
- butyl
- xanthine
- 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
- 238000000034 method Methods 0.000 title claims description 70
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title abstract description 133
- 239000004044 bronchoconstricting agent Substances 0.000 title abstract description 13
- 230000002741 bronchospastic effect Effects 0.000 title abstract description 13
- 208000026935 allergic disease Diseases 0.000 title abstract description 10
- -1 xanthine compound Chemical class 0.000 claims abstract description 96
- 229940075420 xanthine Drugs 0.000 claims abstract description 63
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 12
- 150000001875 compounds Chemical class 0.000 claims description 86
- 230000008569 process Effects 0.000 claims description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 159000000000 sodium salts Chemical class 0.000 claims description 11
- 229940035893 uracil Drugs 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- MTBUJUHRXVGLEF-UHFFFAOYSA-N 1,8-dimethyl-3-(2-methylbutyl)-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(CC(C)CC)C2=C1NC(C)=N2 MTBUJUHRXVGLEF-UHFFFAOYSA-N 0.000 claims description 7
- IVSIEJNJCOMQOI-UHFFFAOYSA-N methyl 1,8-dimethyl-3-(2-methylbutyl)-2,6-dioxopurine-7-carboxylate Chemical compound O=C1N(C)C(=O)N(CC(C)CC)C2=C1N(C(=O)OC)C(C)=N2 IVSIEJNJCOMQOI-UHFFFAOYSA-N 0.000 claims description 7
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 2
- JGULMIZILIGJNC-UHFFFAOYSA-N 1,8-dimethyl-3-(2-methylpropyl)-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(CC(C)C)C2=C1NC(C)=N2 JGULMIZILIGJNC-UHFFFAOYSA-N 0.000 claims 4
- JSHNROWKYDMIPY-UHFFFAOYSA-N ethyl 1,8-dimethyl-3-(2-methylbutyl)-2,6-dioxopurine-7-carboxylate Chemical compound CCC(C)CN1C(=O)N(C)C(=O)C2=C1N=C(C)N2C(=O)OCC JSHNROWKYDMIPY-UHFFFAOYSA-N 0.000 claims 2
- FMMLZIIOIXDGBB-UHFFFAOYSA-N ethyl 1,8-dimethyl-3-(2-methylpropyl)-2,6-dioxopurine-7-carboxylate Chemical compound CC(C)CN1C(=O)N(C)C(=O)C2=C1N=C(C)N2C(=O)OCC FMMLZIIOIXDGBB-UHFFFAOYSA-N 0.000 claims 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 2
- HVIXICZZLUIYOZ-UHFFFAOYSA-N methyl 1,8-dimethyl-3-(2-methylpropyl)-2,6-dioxopurine-7-carboxylate Chemical compound CC(C)CN1C(=O)N(C)C(=O)C2=C1N=C(C)N2C(=O)OC HVIXICZZLUIYOZ-UHFFFAOYSA-N 0.000 claims 2
- UYHDLISIVNPBSN-UHFFFAOYSA-N methyl 1-methyl-3-(2-methylbutyl)-2,6-dioxopurine-7-carboxylate Chemical compound O=C1N(C)C(=O)N(CC(C)CC)C2=C1N(C(=O)OC)C=N2 UYHDLISIVNPBSN-UHFFFAOYSA-N 0.000 claims 2
- SAEZJCXDPPMJHX-UHFFFAOYSA-N propyl 1,8-dimethyl-3-(2-methylbutyl)-2,6-dioxopurine-7-carboxylate Chemical compound CCC(C)CN1C(=O)N(C)C(=O)C2=C1N=C(C)N2C(=O)OCCC SAEZJCXDPPMJHX-UHFFFAOYSA-N 0.000 claims 2
- BISHACNKZIBDFM-UHFFFAOYSA-N 5-amino-1h-pyrimidine-2,4-dione Chemical compound NC1=CNC(=O)NC1=O BISHACNKZIBDFM-UHFFFAOYSA-N 0.000 claims 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 claims 1
- 208000006673 asthma Diseases 0.000 abstract description 17
- 229940124630 bronchodilator Drugs 0.000 abstract description 17
- 239000000243 solution Substances 0.000 abstract description 15
- 239000003826 tablet Substances 0.000 abstract description 13
- 208000030603 inherited susceptibility to asthma Diseases 0.000 abstract description 12
- 239000000168 bronchodilator agent Substances 0.000 abstract description 11
- 239000000443 aerosol Substances 0.000 abstract description 9
- 239000000725 suspension Substances 0.000 abstract description 8
- 239000002775 capsule Substances 0.000 abstract description 7
- 239000000043 antiallergic agent Substances 0.000 abstract description 5
- 239000000829 suppository Substances 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 description 43
- 239000002253 acid Substances 0.000 description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 26
- 230000000694 effects Effects 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 21
- 230000000875 corresponding effect Effects 0.000 description 21
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 20
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 18
- 239000012948 isocyanate Substances 0.000 description 18
- 229960000278 theophylline Drugs 0.000 description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 16
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 15
- 241000700159 Rattus Species 0.000 description 14
- 241000700199 Cavia porcellus Species 0.000 description 13
- 229940079593 drug Drugs 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 241000282472 Canis lupus familiaris Species 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- 229920002472 Starch Polymers 0.000 description 9
- 239000000427 antigen Substances 0.000 description 9
- 102000036639 antigens Human genes 0.000 description 9
- 108091007433 antigens Proteins 0.000 description 9
- 239000004202 carbamide Substances 0.000 description 9
- 235000019698 starch Nutrition 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- 230000007883 bronchodilation Effects 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000008107 starch Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000003266 anti-allergic effect Effects 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 206010006482 Bronchospasm Diseases 0.000 description 6
- 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 6
- 230000000172 allergic effect Effects 0.000 description 6
- 208000010668 atopic eczema Diseases 0.000 description 6
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 6
- 229960001340 histamine Drugs 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- 230000002035 prolonged effect Effects 0.000 description 6
- 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 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- GILKHXWWPFDEDK-UHFFFAOYSA-N N1C(=O)NC=2N=CNC2C1=O.N1C(=O)NC=2N=CN(C2C1=O)C(=O)O Chemical compound N1C(=O)NC=2N=CNC2C1=O.N1C(=O)NC=2N=CN(C2C1=O)C(=O)O GILKHXWWPFDEDK-UHFFFAOYSA-N 0.000 description 5
- SVXXMLPPPZIPSW-UHFFFAOYSA-N N=C=O.O=C1NC(=O)NC2=C1NC=N2 Chemical compound N=C=O.O=C1NC(=O)NC2=C1NC=N2 SVXXMLPPPZIPSW-UHFFFAOYSA-N 0.000 description 5
- 229940008126 aerosol Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 206010016256 fatigue Diseases 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 208000018299 prostration Diseases 0.000 description 5
- 230000002685 pulmonary effect Effects 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000906446 Theraps Species 0.000 description 4
- 230000001154 acute effect Effects 0.000 description 4
- 230000007885 bronchoconstriction Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 230000001665 lethal effect Effects 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 3
- 229930182837 (R)-adrenaline Natural products 0.000 description 3
- 208000024780 Urticaria Diseases 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 208000003455 anaphylaxis Diseases 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000002612 cardiopulmonary effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000007884 disintegrant Substances 0.000 description 3
- 229960005139 epinephrine Drugs 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 229940039009 isoproterenol Drugs 0.000 description 3
- 125000005394 methallyl group Chemical group 0.000 description 3
- 239000003595 mist Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- QWVKBSJJUPSIKV-UHFFFAOYSA-N 1,8-dimethyl-3-(2-methylbutyl)-2,6-dioxopurine-7-carboxylic acid Chemical compound O=C1N(C)C(=O)N(CC(C)CC)C2=C1N(C(O)=O)C(C)=N2 QWVKBSJJUPSIKV-UHFFFAOYSA-N 0.000 description 2
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- 208000014181 Bronchial disease Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 241000237858 Gastropoda Species 0.000 description 2
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- 241001126259 Nippostrongylus brasiliensis Species 0.000 description 2
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- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 2
- WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 230000002804 anti-anaphylactic effect Effects 0.000 description 2
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- 239000011230 binding agent Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 210000000621 bronchi Anatomy 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229960000265 cromoglicic acid Drugs 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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- 239000003085 diluting agent Substances 0.000 description 2
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 2
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- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- NXSXRSNDUVSCRP-UHFFFAOYSA-N 1,3-dimethyl-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2.O=C1N(C)C(=O)N(C)C2=C1NC=N2 NXSXRSNDUVSCRP-UHFFFAOYSA-N 0.000 description 1
- KKWIVMCCCHOXGV-UHFFFAOYSA-N 1-ethyl-3,7-dihydropurine-2,6-dione Chemical compound O=C1N(CC)C(=O)NC2=C1NC=N2 KKWIVMCCCHOXGV-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- XZPRZUAFLSMVCY-UHFFFAOYSA-N 2,6-dioxo-3h-purine-7-carboxylic acid Chemical class N1C(=O)NC(=O)C2=C1N=CN2C(=O)O XZPRZUAFLSMVCY-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 1
- VJROPLWGFCORRM-UHFFFAOYSA-N 2-methylbutan-1-amine Chemical compound CCC(C)CN VJROPLWGFCORRM-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 1
- ALKGIJNHICNRDQ-UHFFFAOYSA-N 5-(2-methylbutyl)-1H-pyrimidine-2,4-dione Chemical compound CC(CC=1C(NC(NC=1)=O)=O)CC ALKGIJNHICNRDQ-UHFFFAOYSA-N 0.000 description 1
- FWAXDJBMCWNBNW-UHFFFAOYSA-N 8-prop-2-ynyl-3,7-dihydropurine-2,6-dione Chemical compound O=C1NC(=O)NC2=C1NC(CC#C)=N2 FWAXDJBMCWNBNW-UHFFFAOYSA-N 0.000 description 1
- 206010027654 Allergic conditions Diseases 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 206010002199 Anaphylactic shock Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100468275 Caenorhabditis elegans rep-1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
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- 241000124008 Mammalia Species 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000000150 Sympathomimetic Substances 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 241000335654 Uracis Species 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 201000010435 allergic urticaria Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229960003556 aminophylline Drugs 0.000 description 1
- FQPFAHBPWDRTLU-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=C1NC=N2.O=C1N(C)C(=O)N(C)C2=C1NC=N2 FQPFAHBPWDRTLU-UHFFFAOYSA-N 0.000 description 1
- 239000000420 anogeissus latifolia wall. gum Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- KPNKNUHGQZCPJY-UHFFFAOYSA-N ethyl 1,3-diethyl-2,6-dioxopurine-7-carboxylate Chemical compound CCN1C(=O)N(CC)C(=O)C2=C1N=CN2C(=O)OCC KPNKNUHGQZCPJY-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001508 eye Anatomy 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000019314 gum ghatti Nutrition 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 239000003453 histamine agonist Substances 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940125386 long-acting bronchodilator Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- JDORMWPGTNFOBC-UHFFFAOYSA-N methyl 1,3-dimethyl-2,6-dioxopurine-7-carboxylate Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C(=O)OC JDORMWPGTNFOBC-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000002850 nasal mucosa Anatomy 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 210000001533 respiratory mucosa Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229940127230 sympathomimetic drug Drugs 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
-
- 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
- A61P11/08—Bronchodilators
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/672,388 US4120947A (en) | 1976-03-31 | 1976-03-31 | Xanthine compounds and method of treating bronchospastic and allergic diseases |
| US05/672,437 US4089959A (en) | 1976-03-31 | 1976-03-31 | Long-acting xanthine bronchodilators and antiallergy agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077932A true CA1077932A (fr) | 1980-05-20 |
Family
ID=27100746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA274,520A Expired CA1077932A (fr) | 1976-03-31 | 1977-03-22 | Composes de la xanthine pour le traitement des bronchospasmes et des affections allergiques |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS52122396A (fr) |
| CA (1) | CA1077932A (fr) |
| DE (1) | DE2713389A1 (fr) |
| FR (1) | FR2346353A1 (fr) |
| GB (1) | GB1561005A (fr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE416810C (sv) | 1977-10-14 | 1982-07-19 | Draco Ab | Forfarande for framstellning av xantinderivat med antiallergisk aktivitet |
| SE7810947L (sv) * | 1978-10-20 | 1980-04-21 | Draco Ab | 3-alkylxanthines |
| SE7810946L (sv) * | 1978-10-20 | 1980-04-21 | Draco Ab | Metod att behandla kronisk obstruktiv luftvegssjukdom |
| SE8002910L (sv) * | 1980-04-18 | 1981-10-19 | Draco Ab | 3,8-dialkylxantiner, forfarande for deras framstellning, beredning och metoder for behandling av kronisk obstruktiv luftvegssjukdom och kardiovaskulera sjukdomar |
| CH643260A5 (fr) * | 1980-05-02 | 1984-05-30 | Nestle Sa | 1-allyl-3-butyl-8-methylxanthine, procede de preparation et utilisation dans un medicament. |
| FR2611716A1 (fr) * | 1987-03-06 | 1988-09-09 | Uriach Cia Sa J | Derives de diisobutylxanthine substituee en position 7 utiles comme bronchodilatateurs, procede pour leur preparation et composition pharmaceutique les contenant |
| GB8826595D0 (en) * | 1988-11-14 | 1988-12-21 | Beecham Wuelfing Gmbh & Co Kg | Active compounds |
| US5321029A (en) * | 1988-11-14 | 1994-06-14 | Beecham-Wuelfing Gmbh & Co.K.G. | Xanthines |
| IT1229195B (it) * | 1989-03-10 | 1991-07-25 | Poli Ind Chimica Spa | Derivati xantinici ad attivita' broncodilatatrice e loro applicazioni terapeutiche. |
| GB9312853D0 (en) | 1993-06-22 | 1993-08-04 | Euro Celtique Sa | Chemical compounds |
| US5591776A (en) | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
| US5922751A (en) | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
| EP0814809B1 (fr) | 1994-12-13 | 2003-08-13 | Euroceltique S.A. | Aryle thioxanthines |
| CA2206804C (fr) | 1994-12-13 | 2002-03-19 | Euro-Celtique, S.A. | Thioxanthines trisubstituees |
| US6166041A (en) | 1995-10-11 | 2000-12-26 | Euro-Celtique, S.A. | 2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma |
| US6075016A (en) | 1996-04-10 | 2000-06-13 | Euro-Celtique S.A. | 6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity |
| US5864037A (en) | 1996-06-06 | 1999-01-26 | Euro-Celtique, S.A. | Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2729643A (en) * | 1956-01-03 | J-disubstmjied and i |
-
1977
- 1977-03-22 CA CA274,520A patent/CA1077932A/fr not_active Expired
- 1977-03-23 DE DE19772713389 patent/DE2713389A1/de active Granted
- 1977-03-28 GB GB12923/77A patent/GB1561005A/en not_active Expired
- 1977-03-31 JP JP3555977A patent/JPS52122396A/ja active Granted
- 1977-03-31 FR FR7709680A patent/FR2346353A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2346353A1 (fr) | 1977-10-28 |
| JPS5720313B2 (fr) | 1982-04-27 |
| DE2713389A1 (de) | 1977-10-13 |
| DE2713389C2 (fr) | 1992-03-19 |
| JPS52122396A (en) | 1977-10-14 |
| GB1561005A (en) | 1980-02-13 |
| FR2346353B1 (fr) | 1980-03-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |