BG60317B2 - Инденоиндолови съединения - Google Patents

Инденоиндолови съединения Download PDF

Info

Publication number: BG60317B2
Authority: BG; Bulgaria
Prior art keywords: indole; cis; tetrahydro; group; formula
Prior art date: 1989-06-22

Application number

BG095667A

Other languages

Bulgarian (bg)

English (en)

Inventor

Malcolm Sainsbury

Howard Shertzer

Original Assignee

University Of Bath

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-06-22

Filing date

1991-12-20

Publication date

1994-07-25

1991-12-20 Application filed by University Of Bath filed Critical University Of Bath

1994-07-25 Publication of BG60317B2 publication Critical patent/BG60317B2/bg

Links

RXXXUIOZOITBII-UHFFFAOYSA-N indeno[1,2-g]indole Chemical class C1=C2C=CC=CC2=C2C1=C1N=CC=C1C=C2 RXXXUIOZOITBII-UHFFFAOYSA-N 0.000 title description 14
150000001875 compounds Chemical class 0.000 claims abstract description 110
125000000217 alkyl group Chemical group 0.000 claims abstract description 44
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 34
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
238000000034 method Methods 0.000 claims abstract description 21
125000003545 alkoxy group Chemical group 0.000 claims abstract description 20
125000001424 substituent group Chemical group 0.000 claims abstract description 20
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 14
239000001257 hydrogen Substances 0.000 claims abstract description 13
125000003277 amino group Chemical group 0.000 claims abstract description 11
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 12
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 77
239000000203 mixture Substances 0.000 claims description 66
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 39
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 39
-1 tetrahydro-8-methoxyindeno [1,2-b] indole Chemical compound 0.000 claims description 38
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 26
230000009467 reduction Effects 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical class C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 8
239000000543 intermediate Substances 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
238000007126 N-alkylation reaction Methods 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
150000004031 phenylhydrazines Chemical class 0.000 claims description 7
230000006378 damage Effects 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
208000018737 Parkinson disease Diseases 0.000 claims description 5
230000029936 alkylation Effects 0.000 claims description 5
238000005804 alkylation reaction Methods 0.000 claims description 5
239000003638 chemical reducing agent Substances 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
230000000302 ischemic effect Effects 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
201000001320 Atherosclerosis Diseases 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
206010063837 Reperfusion injury Diseases 0.000 claims description 4
239000002246 antineoplastic agent Substances 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
230000004054 inflammatory process Effects 0.000 claims description 4
208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 4
208000037906 ischaemic injury Diseases 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
150000002828 nitro derivatives Chemical class 0.000 claims description 4
206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
206010027654 Allergic conditions Diseases 0.000 claims description 3
208000024827 Alzheimer disease Diseases 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
230000032683 aging Effects 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
229960003444 immunosuppressant agent Drugs 0.000 claims description 3
239000003018 immunosuppressive agent Substances 0.000 claims description 3
150000002475 indoles Chemical class 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
230000002265 prevention Effects 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
208000005189 Embolism Diseases 0.000 claims description 2
206010014523 Embolism and thrombosis Diseases 0.000 claims description 2
208000007536 Thrombosis Diseases 0.000 claims description 2
238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
230000000118 anti-neoplastic effect Effects 0.000 claims description 2
229940034982 antineoplastic agent Drugs 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical class C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 claims description 2
230000004968 inflammatory condition Effects 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
LEGKEDBIGQWIIW-UHFFFAOYSA-N 1,2-dimethylindeno[1,2-b]indole Chemical compound CC=1C(=C2C=C3C(=NC=4C=CC=CC34)C2=CC1)C LEGKEDBIGQWIIW-UHFFFAOYSA-N 0.000 claims 2
125000002950 monocyclic group Chemical group 0.000 claims 2
YPAABVKPVMRLCF-UHFFFAOYSA-N 2,4-dimethoxy-1,3-dimethylindeno[1,2-b]indole Chemical compound COC=1C(=C(C(=C2C=C3C(=NC=4C=CC=CC34)C12)C)OC)C YPAABVKPVMRLCF-UHFFFAOYSA-N 0.000 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
125000002252 acyl group Chemical group 0.000 claims 1
150000002170 ethers Chemical class 0.000 claims 1
150000002476 indolines Chemical class 0.000 claims 1
239000003701 inert diluent Substances 0.000 claims 1
238000006864 oxidative decomposition reaction Methods 0.000 claims 1
238000010525 oxidative degradation reaction Methods 0.000 claims 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 1
229940067157 phenylhydrazine Drugs 0.000 claims 1
230000000087 stabilizing effect Effects 0.000 claims 1
239000003963 antioxidant agent Substances 0.000 abstract description 12
229910052736 halogen Inorganic materials 0.000 abstract description 3
150000002367 halogens Chemical class 0.000 abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 167
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 144
239000000243 solution Substances 0.000 description 141
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 65
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 59
239000007787 solid Substances 0.000 description 58
238000005481 NMR spectroscopy Methods 0.000 description 52
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 50
239000002904 solvent Substances 0.000 description 47
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
239000011541 reaction mixture Substances 0.000 description 43
239000000047 product Substances 0.000 description 37
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
229910052938 sodium sulfate Inorganic materials 0.000 description 30
235000011152 sodium sulphate Nutrition 0.000 description 30
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
239000000284 extract Substances 0.000 description 22
229960000583 acetic acid Drugs 0.000 description 21
239000003921 oil Substances 0.000 description 20
235000019198 oils Nutrition 0.000 description 20
238000003756 stirring Methods 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
239000000377 silicon dioxide Substances 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
239000012074 organic phase Substances 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
238000001914 filtration Methods 0.000 description 15
239000012362 glacial acetic acid Substances 0.000 description 15
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
238000004440 column chromatography Methods 0.000 description 13
150000002632 lipids Chemical class 0.000 description 13
230000003647 oxidation Effects 0.000 description 13
238000007254 oxidation reaction Methods 0.000 description 13
239000003208 petroleum Substances 0.000 description 13
150000003254 radicals Chemical class 0.000 description 13
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 12
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
239000012267 brine Substances 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
239000000725 suspension Substances 0.000 description 12
235000006708 antioxidants Nutrition 0.000 description 11
238000003818 flash chromatography Methods 0.000 description 11
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
239000008346 aqueous phase Substances 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000013543 active substance Substances 0.000 description 9
239000012043 crude product Substances 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
125000004356 hydroxy functional group Chemical group O* 0.000 description 9
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 9
229910000029 sodium carbonate Inorganic materials 0.000 description 9
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
239000013078 crystal Substances 0.000 description 8
239000010410 layer Substances 0.000 description 8
238000000746 purification Methods 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
239000002253 acid Substances 0.000 description 7
239000011668 ascorbic acid Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
235000010323 ascorbic acid Nutrition 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000001569 carbon dioxide Substances 0.000 description 6
229910002092 carbon dioxide Inorganic materials 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
239000012230 colorless oil Substances 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
201000010099 disease Diseases 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000003480 eluent Substances 0.000 description 6
238000005755 formation reaction Methods 0.000 description 6
239000007789 gas Substances 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
239000012528 membrane Substances 0.000 description 6
150000002978 peroxides Chemical class 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000011347 resin Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
BEKNOGMQVKBMQN-UHFFFAOYSA-N 2-methyl-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(=O)C(C)CC2=C1 BEKNOGMQVKBMQN-UHFFFAOYSA-N 0.000 description 5
VZUNGTLZRAYYDE-UHFFFAOYSA-N N-methyl-N'-nitro-N-nitrosoguanidine Chemical compound O=NN(C)C(=N)N[N+]([O-])=O VZUNGTLZRAYYDE-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
229940087168 alpha tocopherol Drugs 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
229910052786 argon Inorganic materials 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000000605 extraction Methods 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 5
239000012047 saturated solution Substances 0.000 description 5
229960000984 tocofersolan Drugs 0.000 description 5
238000005406 washing Methods 0.000 description 5
239000002076 α-tocopherol Substances 0.000 description 5
235000004835 α-tocopherol Nutrition 0.000 description 5
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
VMMUGOUUBVDDPV-UHFFFAOYSA-N 1,2,3,3a-tetrahydroindeno[1,2-g]indole Chemical class C1=CC2=C3C=CC=CC3=CC2=C2C1CCN2 VMMUGOUUBVDDPV-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
244000166102 Eucalyptus leucoxylon Species 0.000 description 4
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
230000003078 antioxidant effect Effects 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
229940072107 ascorbate Drugs 0.000 description 4
239000002585 base Substances 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
238000004821 distillation Methods 0.000 description 4
210000003743 erythrocyte Anatomy 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
210000003494 hepatocyte Anatomy 0.000 description 4
QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
125000000864 peroxy group Chemical group O(O*)* 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
230000006641 stabilisation Effects 0.000 description 4
238000011105 stabilization Methods 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 4
CLTUZVAQYOUQDJ-UHFFFAOYSA-N (4-methoxy-2-methylphenyl)hydrazine Chemical compound COC1=CC=C(NN)C(C)=C1 CLTUZVAQYOUQDJ-UHFFFAOYSA-N 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229960005070 ascorbic acid Drugs 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229910052796 boron Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
230000001472 cytotoxic effect Effects 0.000 description 3
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239000003085 diluting agent Substances 0.000 description 1
239000001177 diphosphate Substances 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229940124642 endogenous agent Drugs 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000005454 flavour additive Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
235000013373 food additive Nutrition 0.000 description 1
239000002778 food additive Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009920 food preservation Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
231100000234 hepatic damage Toxicity 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000007574 infarction Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
210000005240 left ventricle Anatomy 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
230000003859 lipid peroxidation Effects 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000008818 liver damage Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
CDGNLUSBENXDGG-UHFFFAOYSA-N meta-Cresidine Chemical compound COC1=CC=C(N)C(C)=C1 CDGNLUSBENXDGG-UHFFFAOYSA-N 0.000 description 1
230000008811 mitochondrial respiratory chain Effects 0.000 description 1
UOMBONFALRJTIP-UHFFFAOYSA-N morpholin-4-ylborane Chemical compound BN1CCOCC1 UOMBONFALRJTIP-UHFFFAOYSA-N 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
210000000440 neutrophil Anatomy 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
210000003024 peritoneal macrophage Anatomy 0.000 description 1
238000005502 peroxidation Methods 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
230000027756 respiratory electron transport chain Effects 0.000 description 1
239000002342 ribonucleoside Substances 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 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
235000012222 talc Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pulmonology (AREA)
Immunology (AREA)
Rheumatology (AREA)
Vascular Medicine (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Toxicology (AREA)
Biochemistry (AREA)
Hospice & Palliative Care (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Psychiatry (AREA)
Psychology (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

BG095667A 1989-06-22 1991-12-20 Инденоиндолови съединения BG60317B2 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE8902274A SE8902274D0 (sv)	1989-06-22	1989-06-22	Indenoidole compounds ii
PCT/GB1990/000949 WO1990015799A1 (en)	1989-06-22	1990-06-20	Indenoindole compounds ii

Publications (1)

Publication Number	Publication Date
BG60317B2 true BG60317B2 (bg)	1994-07-25

Family

ID=20376370

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG095667A BG60317B2 (bg)	1989-06-22	1991-12-20	Инденоиндолови съединения

Country Status (34)

Country	Link
EP (1)	EP0409410B1 (no)
JP (1)	JP3064411B2 (no)
KR (1)	KR920702679A (no)
CN (1)	CN1033029C (no)
AT (1)	ATE135688T1 (no)
BG (1)	BG60317B2 (no)
CA (1)	CA2060897A1 (no)
DD (1)	DD297960A5 (no)
DE (1)	DE69025998T2 (no)
DK (1)	DK0409410T3 (no)
DZ (1)	DZ1428A1 (no)
ES (1)	ES2084660T3 (no)
FI (1)	FI100800B (no)
GR (1)	GR3019779T3 (no)
HR (1)	HRP920903B1 (no)
HU (1)	HUT59097A (no)
IE (1)	IE74682B1 (no)
IL (1)	IL94830A (no)
IS (1)	IS3590A7 (no)
LT (1)	LT3675B (no)
LV (1)	LV10253B (no)
MX (1)	MX21244A (no)
MY (1)	MY107311A (no)
NO (1)	NO177932C (no)
NZ (1)	NZ234175A (no)
PL (1)	PL167761B1 (no)
PT (1)	PT94468B (no)
RO (1)	RO111573B1 (no)
RU (1)	RU2104270C1 (no)
SE (1)	SE8902274D0 (no)
SI (1)	SI9011223B (no)
WO (1)	WO1990015799A1 (no)
YU (1)	YU122390A (no)
ZA (1)	ZA904827B (no)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JO1676B1 (en) *	1990-10-16	1992-08-09	جامعة باث	Extra compounds indinol II
JPH0656669A (ja) *	1992-06-11	1994-03-01	Asahi Breweries Ltd	活性酸素消去作用を持つプテリン誘導体製剤
SE9302431D0 (sv) *	1993-07-16	1993-07-16	Ab Astra	Use of indenoindole compounds
CA2128283A1 (fr) *	1993-07-20	1995-01-21	Paul Caubere	(thia)cycloalkyl¬b\|indoles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
US6288099B1 (en)	1998-12-04	2001-09-11	American Home Products Corporation	Substituted benzofuranoindoles and indenoindoles as novel potassium channel openers
CN1333774A (zh) *	1998-12-04	2002-01-30	美国家庭用品有限公司	以取代苯并呋喃并吲哚和茚并[1,2－b]吲哚作为新的钾通道开放剂
FR2826009B1 (fr) *	2001-06-13	2003-08-15	Servier Lab	Nouveaux derives d'indenoindolones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
RU2008105071A (ru)	2005-07-14	2009-08-20	Айрм Ллк (Bm)	Соединения и композиции в качестве миметиков tro
DE102006047231B4 (de) *	2006-10-04	2009-02-12	Hemmerling, Hans-Jörg, Dr.	Substituierte Indeno[1,2-b]indolderivate als neue Hemmstoffe der Protein Kinase CK2 und ihre Verwendung als Tumor Therapeutika, Cytostatika und Diagnostika
EA026149B1 (ru) *	2011-06-16	2017-03-31	Корея Рисерч Инститьют Оф Кемикал Текнолоджи	Производное инданона, его фармацевтически приемлемая соль или оптический изомер, способ его получения и содержащая его фармацевтическая композиция для профилактики или лечения вирусного заболевания
JP6293168B2 (ja)	2012-12-14	2018-03-14	コーリアリサーチインスティテュートオブケミカルテクノロジー	新規の化合物、その薬学的に許容可能な塩又は光学異性体、それを作製する方法、及びそれを有効成分として含有するウイルス疾患の予防又は治療用の医薬組成物
JP2023520819A (ja)	2020-04-20	2023-05-19	ノバルティスアーゲー	抗ウイルス１，３－ジ－オキソ－インデン化合物

1989
- 1989-06-22 SE SE8902274A patent/SE8902274D0/xx unknown
1990
- 1990-06-13 IS IS3590A patent/IS3590A7/is unknown
- 1990-06-20 HU HU904825A patent/HUT59097A/hu unknown
- 1990-06-20 DZ DZ900114A patent/DZ1428A1/fr active
- 1990-06-20 CA CA002060897A patent/CA2060897A1/en not_active Abandoned
- 1990-06-20 IE IE224790A patent/IE74682B1/en not_active IP Right Cessation
- 1990-06-20 RO RO149127A patent/RO111573B1/ro unknown
- 1990-06-20 DE DE69025998T patent/DE69025998T2/de not_active Expired - Fee Related
- 1990-06-20 AT AT90306718T patent/ATE135688T1/de active
- 1990-06-20 WO PCT/GB1990/000949 patent/WO1990015799A1/en active IP Right Grant
- 1990-06-20 PL PL90285752A patent/PL167761B1/pl unknown
- 1990-06-20 RU SU5010937A patent/RU2104270C1/ru active
- 1990-06-20 EP EP90306718A patent/EP0409410B1/en not_active Expired - Lifetime
- 1990-06-20 ES ES90306718T patent/ES2084660T3/es not_active Expired - Lifetime
- 1990-06-20 JP JP2508940A patent/JP3064411B2/ja not_active Expired - Fee Related
- 1990-06-20 MX MX21244A patent/MX21244A/es unknown
- 1990-06-20 DK DK90306718.9T patent/DK0409410T3/da active
- 1990-06-21 DD DD90341939A patent/DD297960A5/de not_active IP Right Cessation
- 1990-06-21 NZ NZ234175A patent/NZ234175A/xx unknown
- 1990-06-21 ZA ZA904827A patent/ZA904827B/xx unknown
- 1990-06-21 IL IL9483090A patent/IL94830A/en not_active IP Right Cessation
- 1990-06-21 MY MYPI90001050A patent/MY107311A/en unknown
- 1990-06-22 SI SI9011223A patent/SI9011223B/sl unknown
- 1990-06-22 YU YU122390A patent/YU122390A/sh unknown
- 1990-06-22 PT PT94468A patent/PT94468B/pt not_active IP Right Cessation
- 1990-06-22 CN CN90104933A patent/CN1033029C/zh not_active Expired - Fee Related
1991
- 1991-12-19 FI FI915999A patent/FI100800B/fi active
- 1991-12-20 BG BG095667A patent/BG60317B2/bg unknown
- 1991-12-20 NO NO915049A patent/NO177932C/no unknown
- 1991-12-23 KR KR1019910701951A patent/KR920702679A/ko not_active Application Discontinuation
1992
- 1992-10-02 HR HRP-1223/90A patent/HRP920903B1/xx not_active IP Right Cessation
1993
- 1993-06-14 LV LVP-93-568A patent/LV10253B/xx unknown
- 1993-08-30 LT LTIP912A patent/LT3675B/lt not_active IP Right Cessation
1996
- 1996-04-29 GR GR960401159T patent/GR3019779T3/el unknown

Also Published As

Publication number	Publication date
IE902247A1 (en)	1991-01-16
NZ234175A (en)	1992-12-23
LV10253A (lv)	1994-10-20
DE69025998T2 (de)	1996-08-08
PL285752A1 (en)	1991-03-11
KR920702679A (ko)	1992-10-06
HRP920903B1 (en)	1998-06-30
DE69025998D1 (de)	1996-04-25
EP0409410A1 (en)	1991-01-23
SI9011223A (en)	1997-10-31
ES2084660T3 (es)	1996-05-16
CN1033029C (zh)	1996-10-16
IE902247L (en)	1990-12-22
FI915999A0 (fi)	1991-12-19
WO1990015799A1 (en)	1990-12-27
RU2104270C1 (ru)	1998-02-10
IL94830A0 (en)	1991-04-15
NO915049D0 (no)	1991-12-20
AU644084B2 (en)	1993-12-02
YU122390A (sh)	1992-09-07
CA2060897A1 (en)	1990-12-23
DZ1428A1 (fr)	2004-09-13
IL94830A (en)	1996-07-23
JPH04505923A (ja)	1992-10-15
PL167761B1 (pl)	1995-10-31
HUT59097A (en)	1992-04-28
NO177932B (no)	1995-09-11
MX21244A (es)	1994-03-31
RO111573B1 (ro)	1996-11-29
EP0409410B1 (en)	1996-03-20
IS3590A7 (is)	1990-12-23
HU904825D0 (en)	1992-03-30
ATE135688T1 (de)	1996-04-15
JP3064411B2 (ja)	2000-07-12
HRP920903A2 (hr)	1994-04-30
LT3675B (en)	1996-01-25
AU5836990A (en)	1991-01-08
NO177932C (no)	1995-12-20
FI100800B (fi)	1998-02-27
LTIP912A (en)	1995-03-27
DK0409410T3 (da)	1996-04-29
PT94468B (pt)	1997-12-31
SI9011223B (sl)	1998-08-31
NO915049L (no)	1992-02-21
PT94468A (pt)	1991-02-08
SE8902274D0 (sv)	1989-06-22
CN1051554A (zh)	1991-05-22
GR3019779T3 (en)	1996-07-31
IE74682B1 (en)	1997-07-30
ZA904827B (en)	1991-04-24
MY107311A (en)	1995-11-30
DD297960A5 (de)	1992-01-30
LV10253B (en)	1995-04-20

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EP0527081B1 (fr)	1996-01-03	Nouvelles pipérazinylalcoyl-3 dihydro-2,3 4H-benzoxazine-1,3 ones-4 substituées, leur préparation et leur application en thérapeutique
US5185360A (en)	1993-02-09	Dihydroindenoindole compounds and methods for using the same
US5516788A (en)	1996-05-14	Tetrahydroindenoindole compounds useful in the treatment of conditions associated with free radical formation
AP339A (en)	1994-05-02	Indenoindoles compounds.
EP0433167B1 (fr)	1994-03-02	Nouveaux dérivés de la pipéridine, leur procédé de préparation et les compositions pharmaceutiques les renfermant
AU644084C (en)	1995-01-05	Indenoindole compounds II
EP1129097B1 (en)	2003-01-29	Novel type condensed pyridazinone compounds
EP0449728A1 (fr)	1991-10-02	Nouveaux dérivés de la 4H-pyrrolo (1,2-a)thieno(2,3-f) diazépine(1,4), leur procédé de préparation et les compositions pharmaceutiques les renfermant