DD297960A5 - Indenoindolverbindungen ii - Google Patents

Indenoindolverbindungen ii Download PDF

Info

Publication number: DD297960A5
Authority: DD; German Democratic Republic
Prior art keywords: tetrahydro; indole; cis; formula; thii
Prior art date: 1989-06-22

Application number

DD90341939A

Other languages

German (de)

English (en)

Inventor

Malcolm Sainsbury

Howard G Shartzer

Original Assignee

��@��@��k��

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

1990-06-21

Publication date

1992-01-30

1990-06-21 Application filed by ��@��@��k��, ��@��@��k�� filed Critical ��@��@��k��

1992-01-30 Publication of DD297960A5 publication Critical patent/DD297960A5/de

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 1
150000001875 compounds Chemical class 0.000 claims abstract description 97
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
125000000217 alkyl group Chemical group 0.000 claims abstract description 41
239000001257 hydrogen Substances 0.000 claims abstract description 38
238000000034 method Methods 0.000 claims abstract description 29
150000002431 hydrogen Chemical class 0.000 claims abstract description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
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 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 455
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 232
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 223
239000000203 mixture Substances 0.000 claims description 47
238000006243 chemical reaction Methods 0.000 claims description 42
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 27
-1 2-substituted-1-indanone Chemical class 0.000 claims description 26
230000009467 reduction Effects 0.000 claims description 20
230000008569 process Effects 0.000 claims description 15
238000007126 N-alkylation reaction Methods 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
150000002475 indoles Chemical class 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical class C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 claims description 5
230000003647 oxidation Effects 0.000 claims description 5
238000007254 oxidation reaction Methods 0.000 claims description 5
LKNKQSIPELBEKH-UHFFFAOYSA-N 5,6-dihydro-1h-indene Chemical compound C1CC=C2CC=CC2=C1 LKNKQSIPELBEKH-UHFFFAOYSA-N 0.000 claims description 4
238000005804 alkylation reaction Methods 0.000 claims description 4
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
230000029936 alkylation Effects 0.000 claims description 3
238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
230000000087 stabilizing effect Effects 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims 6
238000006641 Fischer synthesis reaction Methods 0.000 claims 2
UFERIGCCDYCZLN-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-1h-indene Chemical compound C1C=CCC2CC=CC21 UFERIGCCDYCZLN-UHFFFAOYSA-N 0.000 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
239000000470 constituent Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
238000001465 metallisation 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
239000003963 antioxidant agent Substances 0.000 abstract description 12
125000003282 alkyl amino group Chemical group 0.000 abstract description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 130
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
239000000243 solution Substances 0.000 description 105
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
239000007787 solid Substances 0.000 description 56
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
235000019439 ethyl acetate Nutrition 0.000 description 45
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
239000002904 solvent Substances 0.000 description 44
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 30
238000002844 melting Methods 0.000 description 27
230000008018 melting Effects 0.000 description 27
239000011734 sodium Substances 0.000 description 23
239000000284 extract Substances 0.000 description 22
239000000047 product Substances 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 20
229960000583 acetic acid Drugs 0.000 description 19
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
239000000377 silicon dioxide Substances 0.000 description 18
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
239000003921 oil Substances 0.000 description 15
235000019198 oils Nutrition 0.000 description 15
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 15
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-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
239000012362 glacial acetic acid Substances 0.000 description 14
150000003254 radicals Chemical class 0.000 description 14
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
238000003818 flash chromatography Methods 0.000 description 13
238000003756 stirring Methods 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
239000012267 brine Substances 0.000 description 12
238000004440 column chromatography Methods 0.000 description 12
239000003208 petroleum Substances 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
235000006708 antioxidants Nutrition 0.000 description 11
230000003859 lipid peroxidation Effects 0.000 description 11
239000000725 suspension Substances 0.000 description 11
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 10
239000008346 aqueous phase Substances 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
150000004031 phenylhydrazines Chemical class 0.000 description 9
239000000126 substance Substances 0.000 description 9
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
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 8
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 8
239000013543 active substance Substances 0.000 description 8
238000001914 filtration Methods 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
235000010323 ascorbic acid Nutrition 0.000 description 7
239000011668 ascorbic acid Substances 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
239000007789 gas Substances 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
239000011368 organic material Substances 0.000 description 7
230000002829 reductive effect Effects 0.000 description 7
239000007858 starting material Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 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
239000005457 ice water Substances 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
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 6
241000700159 Rattus Species 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
238000002835 absorbance Methods 0.000 description 5
YJROYUJAFGZMJA-UHFFFAOYSA-N boron;morpholine Chemical compound [B].C1COCCN1 YJROYUJAFGZMJA-UHFFFAOYSA-N 0.000 description 5
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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
244000166102 Eucalyptus leucoxylon Species 0.000 description 4
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235000019270 ammonium chloride Nutrition 0.000 description 4
229940072107 ascorbate Drugs 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
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229910002092 carbon dioxide Inorganic materials 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000013058 crude material Substances 0.000 description 4
230000006378 damage Effects 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000000605 extraction Methods 0.000 description 4
239000007903 gelatin capsule 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
239000012528 membrane Substances 0.000 description 4
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000012047 saturated solution Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
238000012360 testing method Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
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230000003078 antioxidant effect Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
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239000002585 base Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
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238000009835 boiling Methods 0.000 description 3
229910052796 boron Inorganic materials 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
231100000135 cytotoxicity Toxicity 0.000 description 3
230000003013 cytotoxicity Effects 0.000 description 3
238000010790 dilution Methods 0.000 description 3
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238000004821 distillation Methods 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
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235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
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230000000302 ischemic effect Effects 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
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239000000825 pharmaceutical preparation Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
239000011343 solid material Substances 0.000 description 3
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ZCAMWXOBYJAHLU-UHFFFAOYSA-N 1h-indene;1h-indole Chemical group C1=CC=C2CC=CC2=C1.C1=CC=C2NC=CC2=C1 ZCAMWXOBYJAHLU-UHFFFAOYSA-N 0.000 description 2
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GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
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FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
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ZAKOWWREFLAJOT-UHFFFAOYSA-N DL-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 2
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239000002841 Lewis acid Substances 0.000 description 2
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MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 2
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CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
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- 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
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- 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

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pulmonology (AREA)
Immunology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Hematology (AREA)
Toxicology (AREA)
Biochemistry (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Diabetes (AREA)
Psychology (AREA)
Pain & Pain Management (AREA)
Rheumatology (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)

DD90341939A 1989-06-22 1990-06-21 Indenoindolverbindungen ii DD297960A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE8902274A SE8902274D0 (sv)	1989-06-22	1989-06-22	Indenoidole compounds ii

Publications (1)

Publication Number	Publication Date
DD297960A5 true DD297960A5 (de)	1992-01-30

Family

ID=20376370

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90341939A DD297960A5 (de)	1989-06-22	1990-06-21	Indenoindolverbindungen ii

Country Status (34)

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

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT99232A (pt) *	1990-10-16	1992-09-30	Univ Bath	Processo de preparacao de compostos de indeno-indolo de composicoes farmaceuticas, e de estabilizacao de compostos susceptiveis de deterioracao oxidadtiva
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
AU675141B2 (en) *	1993-07-20	1997-01-23	Adir Et Compagnie	(Thia)cycloalkyl(b)indoles, process for preparing them and pharmaceutical compositions containing them
US6288099B1 (en)	1998-12-04	2001-09-11	American Home Products Corporation	Substituted benzofuranoindoles and indenoindoles as novel potassium channel openers
EP1135393A2 (en) *	1998-12-04	2001-09-26	American Home Products Corporation	Substituted benzofuranoindoles and indenoindoles as novel potassium channel openers
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
ATE478863T1 (de)	2005-07-14	2010-09-15	Irm Llc	Heterotetracyclische verbindungen als tpo- mimetica
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
CN103764140B (zh) *	2011-06-16	2017-05-17	韩国化学研究院	茚酮衍生物、其药学可接受的盐或光学异构体,其制备方法以及包含其作为活性成分用于预防或治疗病毒性疾病的药物组合物
WO2014092514A1 (ko)	2012-12-14	2014-06-19	한국화학연구원	신규한 화합물, 이의 약학적으로 허용가능한 염 또는 이의 광학 이성질체, 이의 제조방법 및 이를 유효성분으로 함유하는 바이러스성 질환의 예방 또는 치료용 약학적 조성물
KR20260004471A (ko)	2020-04-20	2026-01-08	노파르티스 아게	항바이러스 1,3-다이-옥소-인덴 화합물
TWI909320B (zh)	2020-04-20	2025-12-21	瑞士商諾華公司	抗病毒性1,3-二氧代茚化合物

1989
- 1989-06-22 SE SE8902274A patent/SE8902274D0/xx unknown
1990
- 1990-06-13 IS IS3590A patent/IS3590A7/is unknown
- 1990-06-20 JP JP2508940A patent/JP3064411B2/ja not_active Expired - Fee Related
- 1990-06-20 DK DK90306718.9T patent/DK0409410T3/da active
- 1990-06-20 RO RO149127A patent/RO111573B1/ro unknown
- 1990-06-20 ES ES90306718T patent/ES2084660T3/es not_active Expired - Lifetime
- 1990-06-20 RU SU5010937A patent/RU2104270C1/ru active
- 1990-06-20 WO PCT/GB1990/000949 patent/WO1990015799A1/en not_active Ceased
- 1990-06-20 MX MX21244A patent/MX21244A/es unknown
- 1990-06-20 DZ DZ900114A patent/DZ1428A1/fr active
- 1990-06-20 HU HU904825A patent/HUT59097A/hu unknown
- 1990-06-20 DE DE69025998T patent/DE69025998T2/de not_active Expired - Fee Related
- 1990-06-20 IE IE224790A patent/IE74682B1/en not_active IP Right Cessation
- 1990-06-20 CA CA002060897A patent/CA2060897A1/en not_active Abandoned
- 1990-06-20 PL PL90285752A patent/PL167761B1/pl unknown
- 1990-06-20 EP EP90306718A patent/EP0409410B1/en not_active Expired - Lifetime
- 1990-06-20 AT AT90306718T patent/ATE135688T1/de active
- 1990-06-21 DD DD90341939A patent/DD297960A5/de not_active IP Right Cessation
- 1990-06-21 MY MYPI90001050A patent/MY107311A/en 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 NZ NZ234175A patent/NZ234175A/xx 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 SI SI9011223A patent/SI9011223B/sl unknown
- 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 Ceased
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
DE69025998D1 (de)	1996-04-25
BG60317B2 (bg)	1994-07-25
DK0409410T3 (da)	1996-04-29
DZ1428A1 (fr)	2004-09-13
MX21244A (es)	1994-03-31
JPH04505923A (ja)	1992-10-15
PT94468A (pt)	1991-02-08
HRP920903A2 (hr)	1994-04-30
WO1990015799A1 (en)	1990-12-27
IE902247L (en)	1990-12-22
DE69025998T2 (de)	1996-08-08
YU122390A (sh)	1992-09-07
PL285752A1 (en)	1991-03-11
ES2084660T3 (es)	1996-05-16
ZA904827B (en)	1991-04-24
SE8902274D0 (sv)	1989-06-22
FI100800B (fi)	1998-02-27
AU5836990A (en)	1991-01-08
HUT59097A (en)	1992-04-28
LV10253B (en)	1995-04-20
LT3675B (en)	1996-01-25
CN1033029C (zh)	1996-10-16
FI915999A0 (fi)	1991-12-19
PT94468B (pt)	1997-12-31
IE902247A1 (en)	1991-01-16
KR920702679A (ko)	1992-10-06
CA2060897A1 (en)	1990-12-23
EP0409410A1 (en)	1991-01-23
EP0409410B1 (en)	1996-03-20
JP3064411B2 (ja)	2000-07-12
PL167761B1 (pl)	1995-10-31
SI9011223B (sl)	1998-08-31
GR3019779T3 (en)	1996-07-31
IS3590A7 (is)	1990-12-23
NO915049L (no)	1992-02-21
HU904825D0 (en)	1992-03-30
LTIP912A (en)	1995-03-27
HRP920903B1 (en)	1998-06-30
IL94830A0 (en)	1991-04-15
MY107311A (en)	1995-11-30
LV10253A (lv)	1994-10-20
AU644084B2 (en)	1993-12-02
RU2104270C1 (ru)	1998-02-10
NO915049D0 (no)	1991-12-20
ATE135688T1 (de)	1996-04-15
IE74682B1 (en)	1997-07-30
NO177932C (no)	1995-12-20
RO111573B1 (ro)	1996-11-29
NO177932B (no)	1995-09-11
SI9011223A (en)	1997-10-31
IL94830A (en)	1996-07-23
CN1051554A (zh)	1991-05-22
NZ234175A (en)	1992-12-23

Legal Events

Date	Code	Title	Description
1999-12-23	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69322033T2 (de)	1999-06-17	Kondensierte Pyridin Derivate als Hemmer von Effekten freier Radikaler
DD297960A5 (de)	1992-01-30	Indenoindolverbindungen ii
DE2718669C2 (el)	1987-06-11
DE69533194T2 (de)	2005-08-11	PYRAZOLO(3,4-g)CHINOXALINE ALS PDGF-REZEPTOR PROTEIN TYROSIN-KINASE INHIBITOREN
DE69200394T2 (de)	1995-04-27	3-Sulfonylamino-2-(1H)-Chinolinone und deren 7-Azaderivate als anregende Aminosäuren Antagonisten.
KR100234445B1 (ko)	1999-12-15	(((아릴알킬피페리딘-4-일)메틸)-2a,3,4,5-테트라하이드로-1(2h)-아세나프틸렌-1-온 및 관련 화합물,이의 제조방법 및 이를 포함하는 약제학적 조성물
IE75716B1 (en)	1997-09-24	Aminocarbonylcarbamates related to physostigmine a process for their preparation and their use as medicaments
DE69629341T2 (de)	2004-06-09	Pyrrolocarbazolderivate
DD298388A5 (de)	1992-02-20	Indenoindolverbindungen
DE60002043T2 (de)	2004-02-19	4-oxo-3,5-dihydro-4h-pyridazino[4,5-b]indol-1-carboxamid-derivate, ihre herstellung und therapeutische verwendung
DE10053813A1 (de)	2002-05-08	Neue Verwendung von Sulfonamiden
DE69521887T2 (de)	2001-11-22	Verbessertes verfahren zur herstellung von 6,9[(zaminoethyl)amino]benzo[g]isochinoline-5,10 dione und sein dimaleinsaeure salz
FR2467848A1 (fr)	1981-04-30	Sels d'acides 6,7-dihalo-3,4-dihydro-3-oxo-2-quinoxalinecarboxyliques et d'amines steriquement encombrees, leur preparation et leur utilisation therapeutique
US5516788A (en)	1996-05-14	Tetrahydroindenoindole compounds useful in the treatment of conditions associated with free radical formation
CZ65393A3 (en)	1994-02-16	Indenoindole derivative, process of its preparation and pharmaceutical preparation in which said derivative is comprised
WO1998020013A9 (de)	1998-07-02	Neue knoevenagel-kondensationsprodukte, verfahren zu deren herstellung und verwendung
DE10226592B4 (de)	2004-07-29	Tumorhemmende Platin(II)-oxalato-Komplexe
DE68921470T2 (de)	1995-08-03	Diazabicycloalkan-derivate.
AU644084C (en)	1995-01-05	Indenoindole compounds II
EP0937089A1 (de)	1999-08-25	Neue knoevenagel-kondensationsprodukte, verfahren zu deren herstellung und verwendung
DE602005004278T2 (de)	2008-12-24	Arylpyrrol mit antitubulinwirkung, arylfulran- und arylthiopenderivate, verfahren zur herstellung und verwendung als antimitotikum
US2803627A (en)	1957-08-20	Therapeutic quinoline compounds
DE10253720A1 (de)	2004-07-29	10-Phenylimino-9(10H)-anthracenone als neue Inhibitoren der Tubulin-Polymerisation
DE10253746A1 (de)	2004-06-03	10-Benzyliden-1,8-dichlor-9(10H)-anthracenone als neue Inhibitoren der Tubulin-Polymerisation
CS202088B2 (en)	1980-12-31	Method of producing tetrameric complex of malonylurea derivatives