CH648295A5 - Acides 2-amino-3-(alkylthiobenzyl)-phenylacetiques et leurs derives. - Google Patents
Acides 2-amino-3-(alkylthiobenzyl)-phenylacetiques et leurs derives. Download PDFInfo
- Publication number
- CH648295A5 CH648295A5 CH5844/80A CH584480A CH648295A5 CH 648295 A5 CH648295 A5 CH 648295A5 CH 5844/80 A CH5844/80 A CH 5844/80A CH 584480 A CH584480 A CH 584480A CH 648295 A5 CH648295 A5 CH 648295A5
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- indoline
- methylthiobenzoyl
- fluorobenzoyl
- lower alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000001340 alkali metals Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 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 claims description 4
- 238000005054 agglomeration Methods 0.000 claims description 4
- 230000002776 aggregation Effects 0.000 claims description 4
- 210000001772 blood platelet Anatomy 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- PWIJTUWHZXAGDT-UHFFFAOYSA-N 2-[2-amino-3-(4-methylbenzenecarbothioyl)phenyl]acetic acid Chemical compound C1=CC(C)=CC=C1C(=S)C1=CC=CC(CC(O)=O)=C1N PWIJTUWHZXAGDT-UHFFFAOYSA-N 0.000 claims 1
- FDSXVFAKDSQZDK-UHFFFAOYSA-N NC1=C(C=CC=C1C(C1=CC=C(C=C1)C)=S)CC(=O)O.[Na] Chemical compound NC1=C(C=CC=C1C(C1=CC=C(C=C1)C)=S)CC(=O)O.[Na] FDSXVFAKDSQZDK-UHFFFAOYSA-N 0.000 claims 1
- 229940035676 analgesics Drugs 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical group [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims 1
- 150000001457 metallic cations Chemical class 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 150000004682 monohydrates Chemical class 0.000 claims 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 1
- -1 alkali metal salt Chemical class 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 7
- 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
- 239000002253 acid Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
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- 235000019698 starch Nutrition 0.000 description 5
- VEJGTXTYYIPXPQ-UHFFFAOYSA-N 7-(4-fluorobenzoyl)-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical class CSC1C(=O)NC2=C1C=CC=C2C(=O)C1=CC=C(F)C=C1 VEJGTXTYYIPXPQ-UHFFFAOYSA-N 0.000 description 4
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- 239000004480 active ingredient Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- XJDQUPFWVIUWNZ-UHFFFAOYSA-N o-ethyl propanethioate Chemical compound CCOC(=S)CC XJDQUPFWVIUWNZ-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- RFCZOOGIQZASOR-UHFFFAOYSA-N 7-(2-fluorobenzoyl)-1,3-dihydroindol-2-one Chemical class FC1=CC=CC=C1C(=O)C1=CC=CC2=C1NC(=O)C2 RFCZOOGIQZASOR-UHFFFAOYSA-N 0.000 description 3
- GLKCEZPDFADHPT-UHFFFAOYSA-N 7-(4-fluorobenzoyl)-1,3-dihydroindol-2-one Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC2=C1NC(=O)C2 GLKCEZPDFADHPT-UHFFFAOYSA-N 0.000 description 3
- QFASGUFYVCTZCQ-UHFFFAOYSA-N 7-(4-methylbenzenecarbothioyl)-1,3-dihydroindol-2-one Chemical compound C1=CC(C)=CC=C1C(=S)C1=CC=CC2=C1NC(=O)C2 QFASGUFYVCTZCQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
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- 239000003937 drug carrier Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 229910052751 metal Chemical class 0.000 description 3
- 239000002184 metal Chemical class 0.000 description 3
- NRAJMXHXQHCBHO-UHFFFAOYSA-N (2-aminophenyl)-(2-fluorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1F NRAJMXHXQHCBHO-UHFFFAOYSA-N 0.000 description 2
- FFFXIQFESQNINT-UHFFFAOYSA-N (2-aminophenyl)-(4-fluorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=C(F)C=C1 FFFXIQFESQNINT-UHFFFAOYSA-N 0.000 description 2
- YPDXQRCSVALWAO-UHFFFAOYSA-N 4-chloro-7-(4-fluorobenzoyl)-1,3-dihydroindol-2-one Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(Cl)C2=C1NC(=O)C2 YPDXQRCSVALWAO-UHFFFAOYSA-N 0.000 description 2
- ZLGURPBFSFKPRM-UHFFFAOYSA-N 4-chloro-7-(4-methylbenzenecarbothioyl)-1,3-dihydroindol-2-one Chemical compound C1=CC(C)=CC=C1C(=S)C1=CC=C(Cl)C2=C1NC(=O)C2 ZLGURPBFSFKPRM-UHFFFAOYSA-N 0.000 description 2
- HKOPSPIEDSBFOF-UHFFFAOYSA-N 4-methyl-7-(4-methylbenzenecarbothioyl)-1,3-dihydroindol-2-one Chemical compound C1=CC(C)=CC=C1C(=S)C1=CC=C(C)C2=C1NC(=O)C2 HKOPSPIEDSBFOF-UHFFFAOYSA-N 0.000 description 2
- IFXZTQMZXCTFCD-UHFFFAOYSA-N 5-chloro-7-(4-fluorobenzoyl)-1,3-dihydroindol-2-one Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC(Cl)=CC2=C1NC(=O)C2 IFXZTQMZXCTFCD-UHFFFAOYSA-N 0.000 description 2
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- YGOZHJJQBLXTKO-UHFFFAOYSA-N 6-chloro-7-(4-fluorobenzoyl)-1,3-dihydroindol-2-one Chemical compound C1=CC(F)=CC=C1C(=O)C1=C(NC(=O)C2)C2=CC=C1Cl YGOZHJJQBLXTKO-UHFFFAOYSA-N 0.000 description 2
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- HTJADSCELHIFCN-UHFFFAOYSA-N 6-methyl-7-(4-methylbenzenecarbothioyl)-1,3-dihydroindol-2-one Chemical compound C1=CC(C)=CC=C1C(=S)C1=C(NC(=O)C2)C2=CC=C1C HTJADSCELHIFCN-UHFFFAOYSA-N 0.000 description 2
- XQYMXFREJOWXPO-UHFFFAOYSA-N 7-(2-fluorobenzoyl)-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound CSC1C(=O)NC2=C1C=CC=C2C(=O)C1=CC=CC=C1F XQYMXFREJOWXPO-UHFFFAOYSA-N 0.000 description 2
- JPEFKTAVNOETBH-UHFFFAOYSA-N 7-(2-methylbenzenecarbothioyl)-1,3-dihydroindol-2-one Chemical compound CC1=CC=CC=C1C(=S)C1=CC=CC2=C1NC(=O)C2 JPEFKTAVNOETBH-UHFFFAOYSA-N 0.000 description 2
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- RUASQBOEEKWERA-UHFFFAOYSA-N 7-(3-fluorobenzoyl)-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound CSC1C(=O)NC2=C1C=CC=C2C(=O)C1=CC=CC(F)=C1 RUASQBOEEKWERA-UHFFFAOYSA-N 0.000 description 2
- GFSAHWOYHAHEKM-UHFFFAOYSA-N 7-(3-methylbenzenecarbothioyl)-1,3-dihydroindol-2-one Chemical compound CC1=CC=CC(C(=S)C=2C=3NC(=O)CC=3C=CC=2)=C1 GFSAHWOYHAHEKM-UHFFFAOYSA-N 0.000 description 2
- MVNDWIWZTNJYPS-UHFFFAOYSA-N 7-(4-butylbenzenecarbothioyl)-1,3-dihydroindol-2-one Chemical compound C1=CC(CCCC)=CC=C1C(=S)C1=CC=CC2=C1NC(=O)C2 MVNDWIWZTNJYPS-UHFFFAOYSA-N 0.000 description 2
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- SIWOSNUEIVZWGO-UHFFFAOYSA-N 7-(4-fluorobenzoyl)-4-methyl-1,3-dihydroindol-2-one Chemical compound C1=2NC(=O)CC=2C(C)=CC=C1C(=O)C1=CC=C(F)C=C1 SIWOSNUEIVZWGO-UHFFFAOYSA-N 0.000 description 2
- BZGWQACMAACVMN-UHFFFAOYSA-N 7-(4-fluorobenzoyl)-4-methyl-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound CSC1C(=O)NC2=C1C(C)=CC=C2C(=O)C1=CC=C(F)C=C1 BZGWQACMAACVMN-UHFFFAOYSA-N 0.000 description 2
- YSROSFWJTLRRQJ-UHFFFAOYSA-N 7-(4-fluorobenzoyl)-5-methoxy-1,3-dihydroindol-2-one Chemical compound C=1C(OC)=CC=2CC(=O)NC=2C=1C(=O)C1=CC=C(F)C=C1 YSROSFWJTLRRQJ-UHFFFAOYSA-N 0.000 description 2
- MMRUSXZQLSZEIF-UHFFFAOYSA-N 7-(4-fluorobenzoyl)-5-methoxy-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound C=1C(OC)=CC=2C(SC)C(=O)NC=2C=1C(=O)C1=CC=C(F)C=C1 MMRUSXZQLSZEIF-UHFFFAOYSA-N 0.000 description 2
- WQRSNHWRHMQPLP-UHFFFAOYSA-N 7-(4-fluorobenzoyl)-5-methyl-1,3-dihydroindol-2-one Chemical compound C=1C(C)=CC=2CC(=O)NC=2C=1C(=O)C1=CC=C(F)C=C1 WQRSNHWRHMQPLP-UHFFFAOYSA-N 0.000 description 2
- YIXGHFBBUOVHSS-UHFFFAOYSA-N 7-(4-fluorobenzoyl)-5-methyl-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound CSC1C(=O)NC2=C1C=C(C)C=C2C(=O)C1=CC=C(F)C=C1 YIXGHFBBUOVHSS-UHFFFAOYSA-N 0.000 description 2
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- JEYOJRLLXSARRZ-UHFFFAOYSA-N 7-(4-fluorobenzoyl)-6-methyl-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound CSC1C(=O)NC2=C1C=CC(C)=C2C(=O)C1=CC=C(F)C=C1 JEYOJRLLXSARRZ-UHFFFAOYSA-N 0.000 description 2
- HNCMCJJKRWDYIK-UHFFFAOYSA-N 7-(4-propan-2-ylbenzenecarbothioyl)-1,3-dihydroindol-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(=S)C1=CC=CC2=C1NC(=O)C2 HNCMCJJKRWDYIK-UHFFFAOYSA-N 0.000 description 2
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- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
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- 239000001506 calcium phosphate Substances 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
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- 238000010586 diagram Methods 0.000 description 2
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
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- 239000006185 dispersion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 2
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- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 2
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- NCJOIQZFZIESCU-UHFFFAOYSA-M sodium;2-[2-amino-3-(4-methylbenzenecarbothioyl)phenyl]acetate;hydrate Chemical compound O.[Na+].C1=CC(C)=CC=C1C(=S)C1=CC=CC(CC([O-])=O)=C1N NCJOIQZFZIESCU-UHFFFAOYSA-M 0.000 description 2
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- OYBRKOIWKRMOPW-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(4-fluorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=C(F)C=C1 OYBRKOIWKRMOPW-UHFFFAOYSA-N 0.000 description 1
- BLSOWIQSVCVIQB-UHFFFAOYSA-N (2-amino-5-methoxyphenyl)-(4-fluorophenyl)methanone Chemical compound COC1=CC=C(N)C(C(=O)C=2C=CC(F)=CC=2)=C1 BLSOWIQSVCVIQB-UHFFFAOYSA-N 0.000 description 1
- WHIAIKVQXGMCTR-UHFFFAOYSA-N (2-amino-5-methylphenyl)-(4-fluorophenyl)methanone Chemical compound CC1=CC=C(N)C(C(=O)C=2C=CC(F)=CC=2)=C1 WHIAIKVQXGMCTR-UHFFFAOYSA-N 0.000 description 1
- DQYPJBPLMOOWHU-UHFFFAOYSA-N (2-amino-6-chlorophenyl)-(4-fluorophenyl)methanone Chemical compound NC1=CC=CC(Cl)=C1C(=O)C1=CC=C(F)C=C1 DQYPJBPLMOOWHU-UHFFFAOYSA-N 0.000 description 1
- WBMMWAYGKYXSCO-UHFFFAOYSA-N (2-amino-6-methylphenyl)-(4-fluorophenyl)methanone Chemical compound CC1=CC=CC(N)=C1C(=O)C1=CC=C(F)C=C1 WBMMWAYGKYXSCO-UHFFFAOYSA-N 0.000 description 1
- GPJUYTLMEAYQSS-UHFFFAOYSA-N (2-aminophenyl)-(3-fluorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC(F)=C1 GPJUYTLMEAYQSS-UHFFFAOYSA-N 0.000 description 1
- HCLPCHCECDCBCN-UHFFFAOYSA-N 1-benzoyl-3-fluoro-3H-indol-2-one Chemical class C12=CC=CC=C2C(F)C(=O)N1C(=O)C1=CC=CC=C1 HCLPCHCECDCBCN-UHFFFAOYSA-N 0.000 description 1
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical group COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
- DSXZQWBXEGWIRA-UHFFFAOYSA-N 3-methyl-7-(4-methylbenzenecarbothioyl)-1,3-dihydroindol-2-one Chemical compound CC1C(=O)NC2=C1C=CC=C2C(=S)C1=CC=C(C)C=C1 DSXZQWBXEGWIRA-UHFFFAOYSA-N 0.000 description 1
- NROCQGCTPQVXCX-UHFFFAOYSA-N 4-chloro-7-(4-fluorobenzoyl)-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound CSC1C(=O)NC2=C1C(Cl)=CC=C2C(=O)C1=CC=C(F)C=C1 NROCQGCTPQVXCX-UHFFFAOYSA-N 0.000 description 1
- NPUYMQHVYGSERM-UHFFFAOYSA-N 5-chloro-7-(4-chlorobenzoyl)-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C(C(=O)C=2C=C(C=C3C(C(NC23)=O)SC)Cl)C=C1 NPUYMQHVYGSERM-UHFFFAOYSA-N 0.000 description 1
- JWJYYTABDFVJNZ-UHFFFAOYSA-N 5-chloro-7-(4-fluorobenzoyl)-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound CSC1C(=O)NC2=C1C=C(Cl)C=C2C(=O)C1=CC=C(F)C=C1 JWJYYTABDFVJNZ-UHFFFAOYSA-N 0.000 description 1
- BDLLHTOJMDEBLO-UHFFFAOYSA-N 6-chloro-7-(4-methylbenzenecarbothioyl)-1,3-dihydroindol-2-one Chemical compound C1=CC(C)=CC=C1C(=S)C1=C(NC(=O)C2)C2=CC=C1Cl BDLLHTOJMDEBLO-UHFFFAOYSA-N 0.000 description 1
- VGLWOUJFIIOAPK-UHFFFAOYSA-N 7-(4-fluorobenzoyl)-3-methyl-1,3-dihydroindol-2-one Chemical compound CC1C(=O)NC2=C1C=CC=C2C(=O)C1=CC=C(F)C=C1 VGLWOUJFIIOAPK-UHFFFAOYSA-N 0.000 description 1
- ZXYYGAUYLFFBJI-UHFFFAOYSA-N 7-(4-fluorobenzoyl)-3-methyl-3-methylsulfanyl-1h-indol-2-one Chemical compound CSC1(C)C(=O)NC2=C1C=CC=C2C(=O)C1=CC=C(F)C=C1 ZXYYGAUYLFFBJI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- 101800004538 Bradykinin Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
- 102100035792 Kininogen-1 Human genes 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 208000002151 Pleural effusion Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- SOYCMDCMZDHQFP-UHFFFAOYSA-N amfenac Chemical class NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=CC=C1 SOYCMDCMZDHQFP-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 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
- 239000000872 buffer Substances 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-M butane-1-thiolate Chemical compound CCCC[S-] WQAQPCDUOCURKW-UHFFFAOYSA-M 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 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 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-OUBTZVSYSA-N sodium-24 Chemical compound [24Na] KEAYESYHFKHZAL-OUBTZVSYSA-N 0.000 description 1
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6302979A | 1979-08-01 | 1979-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH648295A5 true CH648295A5 (fr) | 1985-03-15 |
Family
ID=22046443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5844/80A CH648295A5 (fr) | 1979-08-01 | 1980-07-31 | Acides 2-amino-3-(alkylthiobenzyl)-phenylacetiques et leurs derives. |
Country Status (37)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0723478U (ja) * | 1993-10-08 | 1995-05-02 | 有限会社伊藤商店 | 衿カバー |
| FR2711076B1 (fr) * | 1993-10-13 | 1995-12-08 | Robatel Slpi | Dispositif étanche et déformable élastiquement pour le débatissage de la couche résiduelle. |
| EP1370527A1 (en) | 2001-03-06 | 2003-12-17 | AstraZeneca AB | Indolone derivatives having vascular-damaging activity |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH577461A5 (enrdf_load_stackoverflow) * | 1975-08-13 | 1976-07-15 | Robins Co Inc A H |
-
1980
- 1980-06-30 IL IL60444A patent/IL60444A/xx unknown
- 1980-07-02 IN IN761/CAL/80A patent/IN151542B/en unknown
- 1980-07-11 AR AR281743A patent/AR226855A1/es active
- 1980-07-14 GB GB8022968A patent/GB2055820B/en not_active Expired
- 1980-07-14 EG EG420/80A patent/EG14771A/xx active
- 1980-07-16 DE DE19803026964 patent/DE3026964A1/de active Granted
- 1980-07-18 FI FI802282A patent/FI74457C/fi not_active IP Right Cessation
- 1980-07-19 GR GR62503A patent/GR69714B/el unknown
- 1980-07-22 BR BR8004546A patent/BR8004546A/pt unknown
- 1980-07-23 YU YU1870/80A patent/YU41725B/xx unknown
- 1980-07-23 PH PH24330A patent/PH18030A/en unknown
- 1980-07-24 CA CA000356926A patent/CA1147746A/en not_active Expired
- 1980-07-24 IE IE1537/80A patent/IE50293B1/en unknown
- 1980-07-28 SE SE8005425A patent/SE447247B/sv not_active IP Right Cessation
- 1980-07-28 AU AU60840/80A patent/AU532247B2/en not_active Ceased
- 1980-07-29 JP JP10423980A patent/JPS5629568A/ja active Granted
- 1980-07-30 LU LU82672A patent/LU82672A1/fr unknown
- 1980-07-30 BE BE0/201593A patent/BE884556A/fr not_active IP Right Cessation
- 1980-07-30 CS CS805349A patent/CS214716B2/cs unknown
- 1980-07-30 KR KR1019800003043A patent/KR840000605B1/ko not_active Expired
- 1980-07-31 NL NL8004397A patent/NL8004397A/nl not_active Application Discontinuation
- 1980-07-31 CH CH5844/80A patent/CH648295A5/fr not_active IP Right Cessation
- 1980-07-31 PL PL1980225990A patent/PL127122B1/pl unknown
- 1980-07-31 IT IT23840/80A patent/IT1132273B/it active
- 1980-07-31 DK DK330380A patent/DK330380A/da unknown
- 1980-07-31 HU HU801919A patent/HU181728B/hu not_active IP Right Cessation
- 1980-07-31 MX MX808949U patent/MX6175E/es unknown
- 1980-07-31 NZ NZ194515A patent/NZ194515A/en unknown
- 1980-07-31 FR FR8016939A patent/FR2463124A1/fr active Granted
- 1980-07-31 PT PT71632A patent/PT71632B/pt unknown
- 1980-07-31 NO NO802306A patent/NO150080C/no unknown
- 1980-07-31 ES ES493880A patent/ES8106702A1/es not_active Expired
- 1980-08-01 ZA ZA00804703A patent/ZA804703B/xx unknown
- 1980-08-04 AT AT0403580A patent/AT369648B/de not_active IP Right Cessation
-
1982
- 1982-05-21 GB GB08214848A patent/GB2105708B/en not_active Expired
-
1984
- 1984-01-18 KE KE3368A patent/KE3368A/xx unknown
- 1984-03-03 SG SG198/84A patent/SG19884G/en unknown
- 1984-03-30 KE KE3390A patent/KE3390A/xx unknown
- 1984-05-03 HK HK375/84A patent/HK37584A/xx unknown
- 1984-06-14 HK HK490/84A patent/HK49084A/xx unknown
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