BG60937B2 - Тетрахидронафталени и съдържащи ги лекарствени средства - Google Patents
Тетрахидронафталени и съдържащи ги лекарствени средства Download PDFInfo
- Publication number
- BG60937B2 BG60937B2 BG098469A BG9846994A BG60937B2 BG 60937 B2 BG60937 B2 BG 60937B2 BG 098469 A BG098469 A BG 098469A BG 9846994 A BG9846994 A BG 9846994A BG 60937 B2 BG60937 B2 BG 60937B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- isopropyl
- methylamino
- tetrahydro
- ethyl
- benzimidazolyl
- Prior art date
Links
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 9
- 206010019280 Heart failures Diseases 0.000 claims abstract description 9
- 206010020772 Hypertension Diseases 0.000 claims abstract description 9
- 206010003119 arrhythmia Diseases 0.000 claims abstract description 9
- 230000006793 arrhythmia Effects 0.000 claims abstract description 9
- 208000028867 ischemia Diseases 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 8
- 230000002265 prevention Effects 0.000 claims abstract description 5
- -1 1-methyl-2-benzimidazolyl Chemical group 0.000 claims description 141
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 58
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 52
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- LKFQQNHKZPKYLK-URLMMPGGSA-N C1=CC=C2NC(CCCN(C)CC[C@]3(CCC4=CC(F)=CC=C4[C@@H]3C(C)C)COCC(O)=O)=NC2=C1 Chemical compound C1=CC=C2NC(CCCN(C)CC[C@]3(CCC4=CC(F)=CC=C4[C@@H]3C(C)C)COCC(O)=O)=NC2=C1 LKFQQNHKZPKYLK-URLMMPGGSA-N 0.000 claims 5
- QPCZBCNNFBHYPU-IOWSJCHKSA-N CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCCCCC3=NC4=CC=CC=C4S3)COCC(=O)O)C=C(C=C2)F Chemical compound CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCCCCC3=NC4=CC=CC=C4S3)COCC(=O)O)C=C(C=C2)F QPCZBCNNFBHYPU-IOWSJCHKSA-N 0.000 claims 1
- 125000005001 aminoaryl group Chemical group 0.000 claims 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- 238000005917 acylation reaction Methods 0.000 abstract description 2
- 230000002213 calciumantagonistic effect Effects 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000012948 isocyanate Substances 0.000 abstract description 2
- 150000002513 isocyanates Chemical class 0.000 abstract description 2
- 238000005576 amination reaction Methods 0.000 abstract 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 261
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 237
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 104
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 99
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 70
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- 239000003921 oil Substances 0.000 description 61
- 235000019198 oils Nutrition 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 239000000203 mixture Substances 0.000 description 56
- 239000011541 reaction mixture Substances 0.000 description 51
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 41
- 239000000741 silica gel Substances 0.000 description 41
- 229910002027 silica gel Inorganic materials 0.000 description 41
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
- 239000000284 extract Substances 0.000 description 24
- 239000007858 starting material Substances 0.000 description 23
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
- 235000019341 magnesium sulphate Nutrition 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 229920006395 saturated elastomer Polymers 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- 239000005457 ice water Substances 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 18
- 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 18
- 239000000843 powder Substances 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
- 239000012043 crude product Substances 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- PEHFQQWAINXOQG-UHFFFAOYSA-N (2-methoxyacetyl) 2-methoxyacetate Chemical compound COCC(=O)OC(=O)COC PEHFQQWAINXOQG-UHFFFAOYSA-N 0.000 description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
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- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000000454 talc Substances 0.000 description 8
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- 229920002261 Corn starch Polymers 0.000 description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
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- 229940099112 cornstarch Drugs 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
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- 235000010446 mineral oil Nutrition 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 150000001204 N-oxides Chemical class 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
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- 229910052763 palladium Inorganic materials 0.000 description 5
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- RAWYKGLVQSJJPW-UHFFFAOYSA-N 3-[4-(methylamino)butyl]-1h-benzimidazol-2-one Chemical compound C1=CC=C2NC(=O)N(CCCCNC)C2=C1 RAWYKGLVQSJJPW-UHFFFAOYSA-N 0.000 description 4
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
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- 229920002472 Starch Polymers 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
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- 238000002474 experimental method Methods 0.000 description 4
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- GOTZAECHGVBWEX-ZDUSSCGKSA-N (6s)-6-[methyl(phenylmethoxycarbonyl)amino]heptanoic acid Chemical compound OC(=O)CCCC[C@H](C)N(C)C(=O)OCC1=CC=CC=C1 GOTZAECHGVBWEX-ZDUSSCGKSA-N 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
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- LXYOUUGAHXHMDC-UHFFFAOYSA-N 1-[4-(1h-benzimidazol-2-ylmethyl)phenyl]-n-methylmethanamine Chemical compound C1=CC(CNC)=CC=C1CC1=NC2=CC=CC=C2N1 LXYOUUGAHXHMDC-UHFFFAOYSA-N 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
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- DLHYYRZDJVRJQW-UHFFFAOYSA-N 3-(4,5-diphenyl-1h-imidazol-2-yl)-n-methylpropan-1-amine Chemical compound N1C(CCCNC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 DLHYYRZDJVRJQW-UHFFFAOYSA-N 0.000 description 3
- FOFJJODTCFUELY-UHFFFAOYSA-N 3-[6-(methylamino)hexyl]-1h-benzimidazol-2-one Chemical compound C1=CC=C2NC(=O)N(CCCCCCNC)C2=C1 FOFJJODTCFUELY-UHFFFAOYSA-N 0.000 description 3
- VCDKZPMRQQQCAZ-UHFFFAOYSA-N 4-[methyl(phenylmethoxycarbonyl)amino]butanoic acid Chemical compound OC(=O)CCCN(C)C(=O)OCC1=CC=CC=C1 VCDKZPMRQQQCAZ-UHFFFAOYSA-N 0.000 description 3
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- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
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- 239000008187 granular material Substances 0.000 description 3
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- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 3
- XUAURPJQDNPORU-UHFFFAOYSA-N n-methyl-1-[4-[(1-methylbenzimidazol-2-yl)methyl]phenyl]methanamine Chemical compound C1=CC(CNC)=CC=C1CC1=NC2=CC=CC=C2N1C XUAURPJQDNPORU-UHFFFAOYSA-N 0.000 description 3
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Electrical Discharge Machining, Electrochemical Machining, And Combined Machining (AREA)
- Organic Insulating Materials (AREA)
- Luminescent Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH456586 | 1986-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG60937B2 true BG60937B2 (bg) | 1996-06-28 |
Family
ID=4278454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG098469A BG60937B2 (bg) | 1986-11-14 | 1994-02-14 | Тетрахидронафталени и съдържащи ги лекарствени средства |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4808605A (lv) |
| EP (1) | EP0268148B1 (lv) |
| JP (1) | JP2504490B2 (lv) |
| KR (1) | KR960004863B1 (lv) |
| CN (1) | CN1028991C (lv) |
| AT (1) | ATE70267T1 (lv) |
| AU (1) | AU600769B2 (lv) |
| BG (1) | BG60937B2 (lv) |
| CA (1) | CA1319144C (lv) |
| CS (2) | CS264350B2 (lv) |
| DE (2) | DE3775177D1 (lv) |
| DK (1) | DK171349B1 (lv) |
| DZ (1) | DZ1142A1 (lv) |
| ES (1) | ES2040234T3 (lv) |
| FI (1) | FI94414C (lv) |
| GR (1) | GR3004029T3 (lv) |
| HK (1) | HK110494A (lv) |
| HU (1) | HU215915B (lv) |
| IE (1) | IE60695B1 (lv) |
| IL (1) | IL84407A (lv) |
| LV (1) | LV5745B4 (lv) |
| MC (1) | MC1883A1 (lv) |
| MX (1) | MX173614B (lv) |
| NL (1) | NL970019I2 (lv) |
| NO (2) | NO172237C (lv) |
| NZ (1) | NZ222474A (lv) |
| PH (1) | PH23919A (lv) |
| PT (1) | PT86130B (lv) |
| SG (1) | SG114194G (lv) |
| ZA (1) | ZA878362B (lv) |
| ZW (1) | ZW20087A1 (lv) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2003283A1 (en) * | 1988-12-05 | 1990-06-05 | C. Anne Higley | Imidazoles for the treatment of atherosclerosis |
| CA2011461A1 (en) * | 1989-03-20 | 1990-09-20 | Urs Hengartner | Tetrahydronaphthalene derivatives |
| NL9001522A (nl) * | 1990-07-04 | 1992-02-03 | Schreiner Luchtvaart | Werkwijze voor het vervaardigen van een voorwerp bestaande uit een schuimkern en eventueel een of meer afdeklagen. |
| TW216770B (lv) * | 1991-07-23 | 1993-12-01 | Hoffmann La Roche | |
| US5250679A (en) * | 1991-10-18 | 1993-10-05 | Genentech, Inc. | Nonpeptidyl platelet aggregation inhibitors having specificity for the GPIIb III.sub. receptor |
| US5674863A (en) * | 1991-10-18 | 1997-10-07 | Genentech, Inc. | Nonpeptidyl integrin inhibitors having specificity for the GPIIb IIIa receptor |
| CN1088062C (zh) * | 1994-11-23 | 2002-07-24 | 纽罗根公司 | 某些4－氨基甲基－2－取代的咪唑衍生物2－氨基甲基－4－取代的咪唑衍生物新的一族多巴胺受体亚型特异性配体 |
| EP0750006B1 (en) | 1995-06-23 | 2002-03-27 | Technische Universiteit Delft | Method of making a foamable film |
| TR199700018A2 (tr) * | 1996-01-31 | 1997-08-21 | Hoffmann La Roche | Alfa,beta-doymamis organik karboksilik asitlerin imaline yönelik proses. |
| US5811556A (en) * | 1997-04-30 | 1998-09-22 | Roche Colorado Corporation | Preparation of mibefradil via a naphthalenylacetic acid |
| US5811557A (en) * | 1997-04-30 | 1998-09-22 | Roche Colorado Corporation | Preparation of mibefradil via an acetonitrile anion |
| US5808088A (en) * | 1997-04-30 | 1998-09-15 | Roche Colorado Corporation | Preparation of mibefradil via an acetamide anion |
| US6897305B2 (en) * | 1998-06-08 | 2005-05-24 | Theravance, Inc. | Calcium channel drugs and uses |
| US7101909B2 (en) * | 1998-10-12 | 2006-09-05 | Theravance, Inc. | Calcium channel drugs and uses |
| US6380224B1 (en) * | 1999-07-28 | 2002-04-30 | Ortho-Mcneil Pharmaceutical, Inc. | Amine and amide derivatives as ligands for the neuropeptide Y Y5 receptor useful in the treatment of obesity and other disorders |
| WO2001062740A1 (en) * | 2000-02-25 | 2001-08-30 | South Alabama Medical Science Foundation | Mibefradil analogues and their use |
| WO2001062741A1 (en) * | 2000-02-25 | 2001-08-30 | South Alabama Medical Science Foundation | Tetrahydronaphtalene derivatives and their use |
| DE60124616T2 (de) * | 2000-05-08 | 2007-09-13 | Pfizer Products Inc., Groton | Enzymatische Spaltung von selektiven Modulatoren des Östrogenrezeptors |
| FR2827862A1 (fr) * | 2001-07-27 | 2003-01-31 | Lipha | Derives imidazolylalkylarylalcanoiques et leurs applications en therapeutique |
| WO2003031415A1 (en) * | 2001-10-10 | 2003-04-17 | Aryx Therapeutics | Mibefradil-based compounds as calcium channel blockers useful in the treatment of hypertension and angina |
| KR20030037081A (ko) | 2001-11-02 | 2003-05-12 | 한국과학기술연구원 | Ｔ 타입 칼슘채널을 조절하여 복통을 억제하는 방법 |
| GEP20074134B (en) | 2002-08-19 | 2007-06-25 | Pfizer Prod Inc | Combination therapy for hyperproliferative diseases |
| US20050037063A1 (en) * | 2003-07-21 | 2005-02-17 | Bolton Anthony E. | Combined therapies |
| RU2373204C2 (ru) * | 2003-07-28 | 2009-11-20 | Янссен Фармацевтика Н.В. | Бензимидазольные, бензтиазольные и бензоксазольные производные и их применение в качестве модуляторов lta4h |
| RU2007106714A (ru) * | 2004-07-26 | 2008-09-10 | Байер Шеринг Фарма Аг (De) | Лечение легочной гипертензии путем ингаляции илопростата с препаратом микрочастиц |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| EP2351569B1 (en) | 2005-10-26 | 2012-08-22 | Asahi Kasei Pharma Corporation | Fasudil in combination therapies for the treatment of pulmonary arterial hypertension |
| EP2111863B1 (en) | 2005-10-26 | 2012-03-28 | Asahi Kasei Pharma Corporation | Fasudil in combination with bosentan for the treament of pulmonary arterial hypertension |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| US7919506B2 (en) | 2006-03-10 | 2011-04-05 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| ATE547394T1 (de) | 2006-12-01 | 2012-03-15 | Bristol Myers Squibb Co | N-((3-benzyl)-2,2-(bis-phenyl)-propan-1- aminderivate als cetp-hemmer für die behandlung von atherosklerose und herz-kreislauf- erkrankungen |
| CL2008000468A1 (es) * | 2007-02-14 | 2008-08-22 | Janssen Pharmaceutica Nv | Uso de compuestos derivados de heterociclos, inhibidores de leucotrina a4 hidrolasa (lta4h), utiles para tratar o prevenir la dermatitis, acne, infarto al miocardio, dolor, picazon, gingivitis, cancer, artritis, entre otras. |
| SI2152670T1 (sl) * | 2007-04-27 | 2014-04-30 | Actelion Pharmaceuticals Ltd. | Premoščene šestčlenske obročne spojine |
| PT2336125E (pt) * | 2008-04-11 | 2013-03-18 | Janssen Pharmaceutica Nv | Tiazolopiridina-2-iloxi-fenil e tiazolopirazin-2-iloxifenil aminas como moduladores de leucotrieno a4 hidrolase |
| AU2009239620A1 (en) | 2008-04-25 | 2009-10-29 | Actelion Pharmaceuticals Ltd | Benzimidazole derivatives as calcium channel blockers |
| CN102186829A (zh) * | 2008-10-22 | 2011-09-14 | 埃科特莱茵药品有限公司 | 桥连四氢萘衍生物 |
| WO2010046729A2 (en) * | 2008-10-23 | 2010-04-29 | Actelion Pharmaceuticals Ltd | Tetrahydronaphthalene compounds |
| CA3027255C (en) | 2009-07-10 | 2022-06-21 | The General Hospital Corporation | Permanently charged sodium and calcium channel blockers as anti-inflammatory agents |
| US8513434B2 (en) | 2010-03-02 | 2013-08-20 | Concert Pharmaceuticals Inc. | Tetrahydronaphthalene derivatives |
| US8575361B2 (en) | 2010-03-02 | 2013-11-05 | Concert Pharmaceuticals Inc. | Tetrahydronaphthalene derivatives |
| WO2012037665A1 (en) | 2010-09-24 | 2012-03-29 | Oral Delivery Technology Ltd. | Nitric oxide releasing amino acid ester for treatment of pulmonary hypertension and other respiratory conditions |
| SG11201507496UA (en) | 2013-04-17 | 2015-11-27 | Pfizer | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| AU2016341429B2 (en) | 2015-10-22 | 2023-09-21 | Cavion, Inc. | Methods for treating Angelman Syndrome and related disorders |
| AU2018221722B2 (en) * | 2017-02-15 | 2022-02-03 | Cavion, Inc. | Calcium channel inhibitors |
| JP7321097B2 (ja) | 2017-04-26 | 2023-08-04 | カビオン・インコーポレイテッド | 記憶および認知を改善する、ならびに記憶および認知障害を処置するための方法 |
| CA3115235A1 (en) | 2018-10-03 | 2020-04-09 | Cavion, Inc. | Treating essential tremor using (r)-2-(4-isopropylphenyl)-n-(1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethyl)acetamide |
| SG11202107614PA (en) | 2019-01-18 | 2021-08-30 | Astrazeneca Ab | Pcsk9 inhibitors and methods of use thereof |
| CN115850119A (zh) * | 2022-11-26 | 2023-03-28 | 南昌大学 | 一种2-氯芳香胺类化合物的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3914216A (en) * | 1962-12-18 | 1975-10-21 | Boehringer Sohn Ingelheim | 1-Phenyl-3H-1,4-benzodiazepine-2,5-(1H,4H)-diones |
| BE793460A (fr) * | 1971-12-29 | 1973-06-28 | Boehringer Sohn Ingelheim | Nouvelles 1-aryl-3h,1,4-benzodiazepine-2,5-(1h |
| NZ213651A (en) * | 1984-10-11 | 1989-07-27 | Hoffmann La Roche | Tetrahydronapthalene derivatives and medicaments |
-
1987
- 1987-10-26 DK DK559987A patent/DK171349B1/da not_active IP Right Cessation
- 1987-10-26 CA CA000550190A patent/CA1319144C/en not_active Expired - Fee Related
- 1987-11-03 CS CS877874A patent/CS264350B2/cs not_active IP Right Cessation
- 1987-11-03 ZW ZW200/87A patent/ZW20087A1/xx unknown
- 1987-11-04 EP EP87116251A patent/EP0268148B1/de not_active Expired - Lifetime
- 1987-11-04 DE DE8787116251T patent/DE3775177D1/de not_active Expired - Fee Related
- 1987-11-04 ES ES198787116251T patent/ES2040234T3/es not_active Expired - Lifetime
- 1987-11-04 DE DE1997175076 patent/DE19775076I2/de active Active
- 1987-11-04 AT AT87116251T patent/ATE70267T1/de active
- 1987-11-06 ZA ZA878362A patent/ZA878362B/xx unknown
- 1987-11-06 NZ NZ222474A patent/NZ222474A/xx unknown
- 1987-11-09 IL IL84407A patent/IL84407A/xx unknown
- 1987-11-09 AU AU80909/87A patent/AU600769B2/en not_active Ceased
- 1987-11-10 US US07/119,114 patent/US4808605A/en not_active Expired - Lifetime
- 1987-11-10 JP JP62282287A patent/JP2504490B2/ja not_active Expired - Lifetime
- 1987-11-11 PH PH36056A patent/PH23919A/en unknown
- 1987-11-11 HU HU875011A patent/HU215915B/hu not_active IP Right Cessation
- 1987-11-11 DZ DZ870191A patent/DZ1142A1/fr active
- 1987-11-12 MX MX009271A patent/MX173614B/es unknown
- 1987-11-12 MC MC871928A patent/MC1883A1/xx unknown
- 1987-11-13 PT PT86130A patent/PT86130B/pt not_active IP Right Cessation
- 1987-11-13 NO NO874757A patent/NO172237C/no not_active IP Right Cessation
- 1987-11-13 FI FI875024A patent/FI94414C/fi not_active IP Right Cessation
- 1987-11-13 IE IE307087A patent/IE60695B1/en not_active IP Right Cessation
- 1987-11-13 CN CN87107875A patent/CN1028991C/zh not_active Expired - Fee Related
- 1987-11-13 KR KR87012777A patent/KR960004863B1/ko not_active IP Right Cessation
-
1991
- 1991-12-20 CS CS913948A patent/CS394891A3/cs unknown
-
1992
- 1992-03-11 GR GR920400420T patent/GR3004029T3/el unknown
-
1994
- 1994-02-14 BG BG098469A patent/BG60937B2/bg unknown
- 1994-08-13 SG SG114194A patent/SG114194G/en unknown
- 1994-10-12 HK HK110494A patent/HK110494A/xx not_active IP Right Cessation
-
1996
- 1996-05-24 LV LV960155A patent/LV5745B4/lv unknown
-
1997
- 1997-05-27 NL NL970019C patent/NL970019I2/nl unknown
-
1998
- 1998-01-09 NO NO1998001C patent/NO1998001I1/no unknown
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