HU219489B - Indolszármazékok, ezeket hatóanyagként tartalmazó gyógyszerészeti készítmények és eljárás előállításukra - Google Patents
Indolszármazékok, ezeket hatóanyagként tartalmazó gyógyszerészeti készítmények és eljárás előállításukra Download PDFInfo
- Publication number
- HU219489B HU219489B HU9300593A HU9300593A HU219489B HU 219489 B HU219489 B HU 219489B HU 9300593 A HU9300593 A HU 9300593A HU 9300593 A HU9300593 A HU 9300593A HU 219489 B HU219489 B HU 219489B
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- HU
- Hungary
- Prior art keywords
- formula
- compound
- ylmethyl
- compounds
- benzyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 33
- 229940054051 antipsychotic indole derivative Drugs 0.000 title abstract description 4
- 150000002475 indoles Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 117
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
- 229910052799 carbon Chemical group 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052717 sulfur Chemical group 0.000 claims abstract description 10
- 239000011593 sulfur Chemical group 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 239000007858 starting material Substances 0.000 claims description 20
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 8
- 150000004678 hydrides Chemical class 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- OZBZDFPXNRIJSJ-LJQANCHMSA-N 3-benzyl-5-[3-[[(2r)-1-methylpyrrolidin-2-yl]methyl]-1h-indol-5-yl]-1,2,4-oxadiazole Chemical compound CN1CCC[C@@H]1CC1=CNC2=CC=C(C=3ON=C(CC=4C=CC=CC=4)N=3)C=C12 OZBZDFPXNRIJSJ-LJQANCHMSA-N 0.000 claims description 3
- DKYCKZKGIKYKKM-HXUWFJFHSA-N 3-benzyl-5-[[3-[[(2r)-1-methylpyrrolidin-2-yl]methyl]-1h-indol-5-yl]methyl]-1,2,4-oxadiazole Chemical compound CN1CCC[C@@H]1CC(C1=C2)=CNC1=CC=C2CC1=NC(CC=2C=CC=CC=2)=NO1 DKYCKZKGIKYKKM-HXUWFJFHSA-N 0.000 claims description 3
- ZJEMBFIIWRKQIH-LJQANCHMSA-N 3-benzyl-5-[[3-[[(2r)-pyrrolidin-2-yl]methyl]-1h-indol-5-yl]methyl]-1,2,4-oxadiazole Chemical compound C=1NC2=CC=C(CC=3ON=C(CC=4C=CC=CC=4)N=3)C=C2C=1C[C@H]1CCCN1 ZJEMBFIIWRKQIH-LJQANCHMSA-N 0.000 claims description 3
- PBGPLEDRCGOGOZ-OAQYLSRUSA-N 4-benzyl-2-[3-[[(2r)-1-methylpyrrolidin-2-yl]methyl]-1h-indol-5-yl]-1,3-thiazole Chemical compound CN1CCC[C@@H]1CC1=CNC2=CC=C(C=3SC=C(CC=4C=CC=CC=4)N=3)C=C12 PBGPLEDRCGOGOZ-OAQYLSRUSA-N 0.000 claims description 3
- VIRILPQYDWEEED-LJQANCHMSA-N 4-benzyl-2-[3-[[(2r)-pyrrolidin-2-yl]methyl]-1h-indol-5-yl]-1,3-thiazole Chemical compound C=1NC2=CC=C(C=3SC=C(CC=4C=CC=CC=4)N=3)C=C2C=1C[C@H]1CCCN1 VIRILPQYDWEEED-LJQANCHMSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- BGKBUFOMIBNPHX-GOSISDBHSA-N 3-benzyl-5-[3-[[(2r)-pyrrolidin-2-yl]methyl]-1h-indol-5-yl]-1,2,4-oxadiazole Chemical compound C=1NC2=CC=C(C=3ON=C(CC=4C=CC=CC=4)N=3)C=C2C=1C[C@H]1CCCN1 BGKBUFOMIBNPHX-GOSISDBHSA-N 0.000 claims 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
- 229940076279 serotonin Drugs 0.000 abstract description 4
- 239000000556 agonist Substances 0.000 abstract description 3
- 238000001671 psychotherapy Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- 239000002904 solvent Substances 0.000 description 36
- -1 (5-substituted) -1H-indoles Chemical class 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 25
- 235000019439 ethyl acetate Nutrition 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000002585 base Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 238000001819 mass spectrum Methods 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 206010027599 migraine Diseases 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 208000019695 Migraine disease Diseases 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 206010019233 Headaches Diseases 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 208000035475 disorder Diseases 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 208000019901 Anxiety disease Diseases 0.000 description 5
- 208000030814 Eating disease Diseases 0.000 description 5
- 208000019454 Feeding and Eating disease Diseases 0.000 description 5
- 208000008589 Obesity Diseases 0.000 description 5
- 208000002193 Pain Diseases 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical class CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 239000000443 aerosol Substances 0.000 description 5
- 230000036506 anxiety Effects 0.000 description 5
- KNIIUQFAZYNNPQ-UHFFFAOYSA-N benzyl 2-(1h-indol-3-ylmethyl)pyrrolidine-1-carboxylate Chemical compound C1CCC(CC=2C3=CC=CC=C3NC=2)N1C(=O)OCC1=CC=CC=C1 KNIIUQFAZYNNPQ-UHFFFAOYSA-N 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 235000014632 disordered eating Nutrition 0.000 description 5
- 206010013663 drug dependence Diseases 0.000 description 5
- 231100000869 headache Toxicity 0.000 description 5
- 235000020824 obesity Nutrition 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 208000011117 substance-related disease Diseases 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 208000019553 vascular disease Diseases 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000010531 catalytic reduction reaction Methods 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000018 receptor agonist Substances 0.000 description 3
- 229940044601 receptor agonist Drugs 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 3
- 229960003708 sumatriptan Drugs 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 3
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical class NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 2
- QDEZFSSAEVJNDS-UHFFFAOYSA-N 3-(pyrrolidin-2-ylmethyl)-1h-indole Chemical class C=1NC2=CC=CC=C2C=1CC1CCCN1 QDEZFSSAEVJNDS-UHFFFAOYSA-N 0.000 description 2
- HCTCDEAMCNSARD-UHFFFAOYSA-N 3-[(1-methylpyrrolidin-2-yl)methyl]-1h-indole Chemical class CN1CCCC1CC1=CNC2=CC=CC=C12 HCTCDEAMCNSARD-UHFFFAOYSA-N 0.000 description 2
- XTNZQPLGXULUSJ-UHFFFAOYSA-N 3-benzyl-1,2,4-oxadiazole Chemical compound C=1C=CC=CC=1CC=1N=CON=1 XTNZQPLGXULUSJ-UHFFFAOYSA-N 0.000 description 2
- FSKUPGNXVRBFFV-UHFFFAOYSA-N 4-(3-benzyl-1,2,4-oxadiazol-5-yl)-2-bromoaniline Chemical compound C1=C(Br)C(N)=CC=C1C1=NC(CC=2C=CC=CC=2)=NO1 FSKUPGNXVRBFFV-UHFFFAOYSA-N 0.000 description 2
- RPPTZAGIYIEAEF-UHFFFAOYSA-N 4-[(3-benzyl-1,2,4-oxadiazol-5-yl)methyl]-2-bromoaniline Chemical compound C1=C(Br)C(N)=CC=C1CC1=NC(CC=2C=CC=CC=2)=NO1 RPPTZAGIYIEAEF-UHFFFAOYSA-N 0.000 description 2
- YMGCICYXYBGECY-UHFFFAOYSA-N 4-amino-3-bromobenzenecarbothioamide Chemical compound NC(=S)C1=CC=C(N)C(Br)=C1 YMGCICYXYBGECY-UHFFFAOYSA-N 0.000 description 2
- POESQIHWIIWNJL-UHFFFAOYSA-N 4-amino-3-bromobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1Br POESQIHWIIWNJL-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 0 CCC*1(C)[U]C(Nc2ccc3[n]cc(CC=C4C(C)CCC4)c3c2)NC1* Chemical compound CCC*1(C)[U]C(Nc2ccc3[n]cc(CC=C4C(C)CCC4)c3c2)NC1* 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 239000012448 Lithium borohydride Substances 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
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- AOZHOGDRJCVQLD-UHFFFAOYSA-N n-[4-(4-benzyl-1,3-thiazol-2-yl)-2-bromophenyl]-2,2,2-trifluoroacetamide Chemical compound C1=C(Br)C(NC(=O)C(F)(F)F)=CC=C1C1=NC(CC=2C=CC=CC=2)=CS1 AOZHOGDRJCVQLD-UHFFFAOYSA-N 0.000 description 1
- KGURQQQNOCZMHP-UHFFFAOYSA-N n-[4-[(3-benzyl-1,2,4-oxadiazol-5-yl)methyl]-2-bromophenyl]-2,2,2-trifluoroacetamide Chemical compound C1=C(Br)C(NC(=O)C(F)(F)F)=CC=C1CC1=NC(CC=2C=CC=CC=2)=NO1 KGURQQQNOCZMHP-UHFFFAOYSA-N 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 210000003752 saphenous vein Anatomy 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 239000003521 serotonin 5-HT1 receptor agonist Substances 0.000 description 1
- 239000000952 serotonin receptor agonist Substances 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Addiction (AREA)
- Hematology (AREA)
- Child & Adolescent Psychology (AREA)
- Obesity (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84664092A | 1992-03-05 | 1992-03-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU9300593D0 HU9300593D0 (en) | 1993-05-28 |
| HUT64061A HUT64061A (en) | 1993-11-29 |
| HU219489B true HU219489B (hu) | 2001-04-28 |
Family
ID=25298499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9300593A HU219489B (hu) | 1992-03-05 | 1993-03-04 | Indolszármazékok, ezeket hatóanyagként tartalmazó gyógyszerészeti készítmények és eljárás előállításukra |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US5594014A (enExample) |
| EP (1) | EP0629199B1 (enExample) |
| JP (1) | JPH07121943B2 (enExample) |
| KR (1) | KR0179073B1 (enExample) |
| CN (4) | CN1032309C (enExample) |
| AT (1) | ATE218566T1 (enExample) |
| AU (1) | AU666716B2 (enExample) |
| BR (1) | BR9306012A (enExample) |
| CA (1) | CA2117643C (enExample) |
| CZ (1) | CZ282652B6 (enExample) |
| DE (1) | DE69331988T2 (enExample) |
| DK (1) | DK0629199T3 (enExample) |
| EG (1) | EG20416A (enExample) |
| ES (1) | ES2176199T3 (enExample) |
| FI (1) | FI930968A7 (enExample) |
| HU (1) | HU219489B (enExample) |
| IL (1) | IL104941A (enExample) |
| MX (1) | MX9301197A (enExample) |
| MY (1) | MY109298A (enExample) |
| NO (1) | NO302617B1 (enExample) |
| NZ (1) | NZ249755A (enExample) |
| PL (1) | PL172388B1 (enExample) |
| PT (1) | PT629199E (enExample) |
| RU (1) | RU2124012C1 (enExample) |
| SK (1) | SK281938B6 (enExample) |
| TW (1) | TW288010B (enExample) |
| UA (1) | UA39866C2 (enExample) |
| WO (1) | WO1993018032A1 (enExample) |
| YU (1) | YU14893A (enExample) |
| ZA (1) | ZA931539B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5559129A (en) * | 1990-10-15 | 1996-09-24 | Pfizer Inc | Indole derivatives |
| US5559246A (en) * | 1990-10-15 | 1996-09-24 | Pfizer Inc. | Indole derivatives |
| US5578612A (en) * | 1990-10-15 | 1996-11-26 | Pfizer Inc. | Indole derivatives |
| US5545644A (en) * | 1990-10-15 | 1996-08-13 | Pfizer Inc. | Indole derivatives |
| US5607951A (en) * | 1990-10-15 | 1997-03-04 | Pfizer Inc | Indole derivatives |
| US6380233B1 (en) | 1992-04-07 | 2002-04-30 | Pfizer Inc | Indole derivatives as 5-HT1 agonists |
| AU670579B2 (en) | 1992-04-07 | 1996-07-25 | Pfizer Inc. | Indole derivatives as 5-HT1 agonists |
| AU686654B2 (en) * | 1993-08-31 | 1998-02-12 | Pfizer Inc. | 5-arylindole derivatives |
| GB9417310D0 (en) | 1994-08-27 | 1994-10-19 | Pfizer Ltd | Therapeutic agents |
| GB9420503D0 (en) * | 1994-10-11 | 1994-11-23 | Pfizer Ltd | Therapeutic agents |
| GB9420529D0 (en) | 1994-10-12 | 1994-11-30 | Pfizer Ltd | Indoles |
| US6288091B1 (en) | 1995-12-29 | 2001-09-11 | Boehringer Ingelheim Ltd. | Antiherpes virus compounds and methods for their preparation and use |
| NZ331104A (en) | 1995-12-29 | 2000-03-27 | Boehringer Ingelheim Ca Ltd | Phenyl thiazole derivatives that inhibit herpes replication by inhibiting the herpes helicase primase enzyme complex |
| US5994352A (en) * | 1998-11-13 | 1999-11-30 | Pfizer Inc. | 5-arylindole derivatives |
| EA200300379A1 (ru) | 2000-11-27 | 2003-08-28 | Пфайзер Продактс Инк. | Селективные агонисты рецептора ep4 в лечении остеопороза |
| PL366639A1 (en) * | 2001-04-20 | 2005-02-07 | Wyeth | Heterocyclylalkoxy-, -alkylthio- and -alkylaminobenzazole derivatives as 5-hydroxytryptamine-6 ligands |
| ITRM20020255A1 (it) * | 2002-05-09 | 2003-11-10 | Polifarma Spa | Tautomero enolico dell'acido 3-indolilpiruvico, suoi sali e usi terapeutici. |
| ES2199086B1 (es) * | 2002-07-31 | 2005-06-01 | Cepa Schwarz Pharma Sl | Nuevos derivados de cicloalcanodionas, procedimiento para su preparacion y sus aplicaciones farmacologicas. |
| GB0317229D0 (en) * | 2003-07-23 | 2003-08-27 | Pfizer Ltd | Improved process |
| US10154988B2 (en) | 2012-11-14 | 2018-12-18 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| AU2021215709A1 (en) * | 2020-02-04 | 2022-09-01 | Mindset Pharma Inc. | 3-pyrrolidine-indole derivatives as serotonergic psychedelic agents for the treatment of CNS disorders |
| PL243119B1 (pl) * | 2020-04-16 | 2023-06-26 | Univ Jagiellonski | Rozpuszczalne w wodzie modyfikowane pochodne aminokwasowe nadające się do leczenia chorób o podłożu neurologicznym oraz zaburzeń psychiatrycznych |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA795239B (en) * | 1978-10-12 | 1980-11-26 | Glaxo Group Ltd | Heterocyclic compounds |
| ZA815541B (en) * | 1980-08-12 | 1983-03-30 | Glaxo Group Ltd | Heterocyclic compounds |
| GB8600397D0 (en) * | 1986-01-08 | 1986-02-12 | Glaxo Group Ltd | Chemical compounds |
| GB8719167D0 (en) * | 1987-08-13 | 1987-09-23 | Glaxo Group Ltd | Chemical compounds |
| GB8724912D0 (en) * | 1987-10-23 | 1987-11-25 | Wellcome Found | Indole derivatives |
| GB8819024D0 (en) * | 1988-08-10 | 1988-09-14 | Glaxo Group Ltd | Chemical compounds |
| IL96891A0 (en) * | 1990-01-17 | 1992-03-29 | Merck Sharp & Dohme | Indole-substituted five-membered heteroaromatic compounds,their preparation and pharmaceutical compositions containing them |
| CA2042295A1 (fr) * | 1990-05-15 | 1991-11-16 | Jacques Chauveau | Derives de mediateurs endogenes, leurs sels, procede de preparation, applications, et compositions les renfermant |
| CZ288351B6 (en) * | 1990-06-07 | 2001-05-16 | Astrazeneca Ab | Nitrogenous heterocyclic compound, process of its preparation and use as well as a medicament containing thereof |
| HU225055B1 (en) * | 1990-10-15 | 2006-05-29 | Pfizer | Indole derivatives, their intermediates, process for production them and pharmaceutical compositions containing the compounds |
| US5208248A (en) * | 1991-01-11 | 1993-05-04 | Merck Sharpe & Dohme, Ltd. | Indazole-substituted five-membered heteroaromatic compounds |
| CZ283018B6 (cs) * | 1991-02-01 | 1997-12-17 | Merck Sharp And Dohme Limited | Deriváty imidazolu, triazolu a tetrazolu a farmaceutické přípravky na jejich bázi |
| TW263508B (enExample) * | 1991-02-12 | 1995-11-21 | Pfizer |
-
1993
- 1993-02-09 TW TW082100871A patent/TW288010B/zh active
- 1993-03-03 AT AT93906214T patent/ATE218566T1/de not_active IP Right Cessation
- 1993-03-03 PT PT93906214T patent/PT629199E/pt unknown
- 1993-03-03 KR KR1019940703076A patent/KR0179073B1/ko not_active Expired - Fee Related
- 1993-03-03 SK SK1052-94A patent/SK281938B6/sk unknown
- 1993-03-03 UA UA94095775A patent/UA39866C2/uk unknown
- 1993-03-03 CZ CZ942125A patent/CZ282652B6/cs not_active IP Right Cessation
- 1993-03-03 EG EG12893A patent/EG20416A/xx active
- 1993-03-03 DK DK93906214T patent/DK0629199T3/da active
- 1993-03-03 RU RU94040914/04A patent/RU2124012C1/ru not_active IP Right Cessation
- 1993-03-03 MX MX9301197A patent/MX9301197A/es unknown
- 1993-03-03 JP JP5515745A patent/JPH07121943B2/ja not_active Expired - Fee Related
- 1993-03-03 WO PCT/US1993/001667 patent/WO1993018032A1/en not_active Ceased
- 1993-03-03 EP EP93906214A patent/EP0629199B1/en not_active Expired - Lifetime
- 1993-03-03 ES ES93906214T patent/ES2176199T3/es not_active Expired - Lifetime
- 1993-03-03 US US08/284,662 patent/US5594014A/en not_active Expired - Fee Related
- 1993-03-03 BR BR9306012A patent/BR9306012A/pt not_active Application Discontinuation
- 1993-03-03 DE DE69331988T patent/DE69331988T2/de not_active Expired - Fee Related
- 1993-03-03 AU AU37330/93A patent/AU666716B2/en not_active Ceased
- 1993-03-03 PL PL93305051A patent/PL172388B1/pl not_active IP Right Cessation
- 1993-03-03 CA CA002117643A patent/CA2117643C/en not_active Expired - Fee Related
- 1993-03-04 MY MYPI93000388A patent/MY109298A/en unknown
- 1993-03-04 CN CN93104036A patent/CN1032309C/zh not_active Expired - Fee Related
- 1993-03-04 IL IL104941A patent/IL104941A/en not_active IP Right Cessation
- 1993-03-04 YU YU14893A patent/YU14893A/sh unknown
- 1993-03-04 HU HU9300593A patent/HU219489B/hu not_active IP Right Cessation
- 1993-03-04 FI FI930968A patent/FI930968A7/fi not_active Application Discontinuation
- 1993-03-04 ZA ZA931539A patent/ZA931539B/xx unknown
- 1993-05-03 NZ NZ249755A patent/NZ249755A/en unknown
-
1994
- 1994-09-02 NO NO943261A patent/NO302617B1/no not_active IP Right Cessation
-
1995
- 1995-11-17 CN CN95118796A patent/CN1044910C/zh not_active Expired - Fee Related
- 1995-11-17 CN CN95118794A patent/CN1082815C/zh not_active Expired - Fee Related
- 1995-11-17 CN CN95118795A patent/CN1044909C/zh not_active Expired - Fee Related
-
1996
- 1996-12-31 US US08/777,835 patent/US5717102A/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
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| MM4A | Lapse of definitive patent protection due to non-payment of fees |