DD258229A5 - Verfahren zur herstellung von neuen heterocyclisch substituierten indolderivaten - Google Patents
Verfahren zur herstellung von neuen heterocyclisch substituierten indolderivaten Download PDFInfo
- Publication number
- DD258229A5 DD258229A5 DD86294092A DD29409286A DD258229A5 DD 258229 A5 DD258229 A5 DD 258229A5 DD 86294092 A DD86294092 A DD 86294092A DD 29409286 A DD29409286 A DD 29409286A DD 258229 A5 DD258229 A5 DD 258229A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- oxo
- group
- methyl
- tetrahydro
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title abstract description 13
- -1 cyano, carboxy Chemical group 0.000 claims abstract description 181
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 9
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims abstract description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 235000005985 organic acids Nutrition 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 5
- 230000000144 pharmacologic effect Effects 0.000 claims description 5
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 5
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 4
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 238000006783 Fischer indole synthesis reaction Methods 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 150000003536 tetrazoles Chemical class 0.000 claims description 3
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 6
- 150000002475 indoles Chemical class 0.000 abstract description 5
- 229940054051 antipsychotic indole derivative Drugs 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 107
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 100
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 229920000137 polyphosphoric acid Polymers 0.000 description 29
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 28
- 229960000583 acetic acid Drugs 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 239000012362 glacial acetic acid Substances 0.000 description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000012043 crude product Substances 0.000 description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 150000007857 hydrazones Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 11
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- WMQUKDQWMMOHSA-UHFFFAOYSA-N 1-pyridin-4-ylethanone Chemical compound CC(=O)C1=CC=NC=C1 WMQUKDQWMMOHSA-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- PIPWEJVMMDGPMM-UHFFFAOYSA-N 3-(4-hydrazinylphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(NN)=CC=C1C1=NNC(=O)CC1 PIPWEJVMMDGPMM-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 230000003213 activating effect Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 229940093915 gynecological organic acid Drugs 0.000 description 5
- 235000011118 potassium hydroxide Nutrition 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000006193 diazotization reaction Methods 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- 150000002429 hydrazines Chemical class 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- XMTUHSIIBGFSTQ-UHFFFAOYSA-N 3-(4-aminophenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(N)=CC=C1C1=NNC(=O)CC1 XMTUHSIIBGFSTQ-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 125000005336 allyloxy group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000001772 blood platelet Anatomy 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
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- 238000001816 cooling Methods 0.000 description 3
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
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- 239000003814 drug Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- ABXGMGUHGLQMAW-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C(F)(F)F)=C1 ABXGMGUHGLQMAW-UHFFFAOYSA-N 0.000 description 2
- AFHFHXVRHACYSR-UHFFFAOYSA-N 1-pyridin-4-ylpropan-1-one Chemical compound CCC(=O)C1=CC=NC=C1 AFHFHXVRHACYSR-UHFFFAOYSA-N 0.000 description 2
- DBZAKQWXICEWNW-UHFFFAOYSA-N 2-acetylpyrazine Chemical compound CC(=O)C1=CN=CC=N1 DBZAKQWXICEWNW-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000006147 Japp-Klingemann synthesis reaction Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- FNENWZWNOPCZGK-UHFFFAOYSA-N ethyl 2-methyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)C(C)=O FNENWZWNOPCZGK-UHFFFAOYSA-N 0.000 description 1
- NGRXSVFCLHVGKU-UHFFFAOYSA-N ethyl 3-(4-nitrophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C([N+]([O-])=O)C=C1 NGRXSVFCLHVGKU-UHFFFAOYSA-N 0.000 description 1
- AEYWGOMYRGQQDY-UHFFFAOYSA-N ethyl 5-(4-methyl-5-oxo-1h-1,2,4-triazol-3-yl)-1h-indole-2-carboxylate Chemical compound C=1C=C2NC(C(=O)OCC)=CC2=CC=1C1=NNC(=O)N1C AEYWGOMYRGQQDY-UHFFFAOYSA-N 0.000 description 1
- JHXFWTLRHWJSJZ-UHFFFAOYSA-N ethyl 5-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)-1h-indole-2-carboxylate Chemical compound C=1C=C2NC(C(=O)OCC)=CC2=CC=1C1=NNC(=O)CC1 JHXFWTLRHWJSJZ-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001205 polyphosphate Chemical class 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 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
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853531658 DE3531658A1 (de) | 1985-09-05 | 1985-09-05 | Heterocyclisch substituierte indole, zwischenprodukte, verfahren zu ihrer herstellung und arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD258229A5 true DD258229A5 (de) | 1988-07-13 |
Family
ID=6280166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86294092A DD258229A5 (de) | 1985-09-05 | 1986-09-02 | Verfahren zur herstellung von neuen heterocyclisch substituierten indolderivaten |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4851406A (el) |
| EP (1) | EP0223937B1 (el) |
| JP (1) | JPS6256486A (el) |
| KR (1) | KR870003099A (el) |
| AT (1) | ATE73797T1 (el) |
| AU (1) | AU572405B2 (el) |
| DD (1) | DD258229A5 (el) |
| DE (2) | DE3531658A1 (el) |
| DK (1) | DK419086A (el) |
| ES (1) | ES2001936A6 (el) |
| FI (1) | FI863564A7 (el) |
| GR (1) | GR862248B (el) |
| HU (1) | HU197000B (el) |
| IL (1) | IL79911A (el) |
| NZ (1) | NZ217419A (el) |
| PT (1) | PT83310B (el) |
| ZA (1) | ZA866705B (el) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2594438B1 (fr) * | 1986-02-14 | 1990-01-26 | Labaz Sanofi Nv | Derives d'indolizine, leur procede de preparation ainsi que les compositions en contenant |
| DE3631085A1 (de) * | 1986-09-12 | 1988-03-24 | Boehringer Mannheim Gmbh | Heterocyclisch substituierte indolinone, verfahren zu ihrer herstellung, arzneimittel sowie zwischenprodukte |
| DE3706427A1 (de) * | 1987-02-27 | 1988-09-08 | Boehringer Mannheim Gmbh | Neue substituierte 3h-indole, zwischenprodukte, verfahren zu ihrer herstellung sowie arzneimittel |
| US5225431A (en) * | 1987-10-23 | 1993-07-06 | Burroughs Wellcome Co. | Therapeutic substituted indole compounds and compositions thereof |
| JP2597893B2 (ja) * | 1988-07-21 | 1997-04-09 | 自動車機器株式会社 | 流体給排用接続筒を備えたシリンダとその製造方法および製造装置 |
| DE3826855A1 (de) * | 1988-08-06 | 1990-02-15 | Cassella Ag | 4,5-dihydro-3(2h)-pyridazinone, verfahren zu ihrer herstellung und ihre verwendung |
| US5238938A (en) * | 1989-02-10 | 1993-08-24 | Otsuka Pharmaceutical Co., Ltd. | Indole derivatives |
| GB8903130D0 (en) | 1989-02-11 | 1989-03-30 | Orion Yhtymae Oy | Substituted pyridazinones |
| US5185332A (en) * | 1989-02-11 | 1993-02-09 | Orion-Yhtyma Oy | Thiadiazines and pharmaceutical compositions thereof as well as method of use |
| PT95899A (pt) * | 1989-11-17 | 1991-09-13 | Glaxo Group Ltd | Processo para a preparacao de derivados indole |
| PT97888B (pt) * | 1990-06-07 | 1998-12-31 | Zeneca Ltd | Processo para a preparacao de compostos heterociclicos derivados de indol e de composicoes farmaceuticas que os contem |
| US5189054A (en) * | 1990-11-02 | 1993-02-23 | Merrell Dow Pharmaceuticals Inc. | 3-amidoindolyl derivatives and pharmaceutical compositions thereof |
| US5317103A (en) * | 1991-01-15 | 1994-05-31 | Merck Sharp & Dohme Limited | Indole-substituted five-membered heteroaromatic compounds as 5-HT1 agonists |
| CZ283018B6 (cs) * | 1991-02-01 | 1997-12-17 | Merck Sharp And Dohme Limited | Deriváty imidazolu, triazolu a tetrazolu a farmaceutické přípravky na jejich bázi |
| US5183825A (en) * | 1992-04-07 | 1993-02-02 | American Home Products Corporation | 4-arylmethyl-5-alkyl-3H-pyrazol-3-ones and hypoglycemic use |
| US5194435A (en) * | 1992-04-07 | 1993-03-16 | American Home Products Corporation | 4-arylmethyl-5-alkyl-3h-pyrazol-3-ones |
| IL106445A (en) * | 1992-07-30 | 1998-01-04 | Merck Sharp & Dohme | History of 1,2,4-Trans-Triazole 4-Transform, Preparation and Pharmaceutical Preparations Containing Them |
| CA2195107A1 (en) * | 1994-08-02 | 1996-02-15 | Richard Alexander Jelley | Azetidine, pyrrolidine and piperidine derivatives |
| US5523312A (en) * | 1994-09-27 | 1996-06-04 | Sterling Winthrop Inc. | Antipicornaviral agents |
| EP1060166A1 (de) * | 1998-02-03 | 2000-12-20 | Boehringer Ingelheim Pharma KG | 5-gliedrige benzokondensierte heterocyclen als antithrombotika |
| US6114532A (en) * | 1998-02-03 | 2000-09-05 | Boehringer Ingelheim Pharma Kg | Bicyclic heterocycles, the preparation thereof, and their use as pharmaceuticals |
| GB9926250D0 (en) * | 1999-11-06 | 2000-01-12 | Knoll Ag | Chemical process |
| FI20000577A0 (fi) * | 2000-03-13 | 2000-03-13 | Orion Yhtymae Oy | Pyridatsinyylifenyylihydratsoneja |
| TWI224101B (en) * | 2001-06-20 | 2004-11-21 | Wyeth Corp | Substituted naphthyl indole derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1) |
| US7074817B2 (en) * | 2001-06-20 | 2006-07-11 | Wyeth | Substituted indole acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1) |
| DE60324183D1 (en) * | 2002-12-10 | 2008-11-27 | Wyeth Corp | Aryl-, aryloxy- und alkyloxysubstituierte 1h-indol-3-yl-glyoxylsäurederivateals inhibitoren des plasminogenaktivatorinhibitors-1 (pai-1) |
| CA2509170A1 (en) * | 2002-12-10 | 2004-06-24 | Wyeth | Substituted 3-alkyl and 3-arylalkyl 1h-indol-1-yl acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| UA80453C2 (en) * | 2002-12-10 | 2007-09-25 | Derivatives of substituted dyhydropyranoindol-3,4-dion as inhibitors of plasminogen activator inhibitor-1 (pai-1) | |
| EP1569900B1 (en) * | 2002-12-10 | 2006-06-28 | Wyeth | Substituted 3-carbonyl-1-yl acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| CA2509222A1 (en) * | 2002-12-10 | 2004-06-24 | Wyeth | Substituted indole oxo-acetyl amino acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| US7351726B2 (en) * | 2003-09-25 | 2008-04-01 | Wyeth | Substituted oxadiazolidinediones |
| US7342039B2 (en) * | 2003-09-25 | 2008-03-11 | Wyeth | Substituted indole oximes |
| US7268159B2 (en) * | 2003-09-25 | 2007-09-11 | Wyeth | Substituted indoles |
| US7534894B2 (en) * | 2003-09-25 | 2009-05-19 | Wyeth | Biphenyloxy-acids |
| US7163954B2 (en) * | 2003-09-25 | 2007-01-16 | Wyeth | Substituted naphthyl benzothiophene acids |
| US7420083B2 (en) * | 2003-09-25 | 2008-09-02 | Wyeth | Substituted aryloximes |
| US7411083B2 (en) * | 2003-09-25 | 2008-08-12 | Wyeth | Substituted acetic acid derivatives |
| US7582773B2 (en) * | 2003-09-25 | 2009-09-01 | Wyeth | Substituted phenyl indoles |
| US7442805B2 (en) * | 2003-09-25 | 2008-10-28 | Wyeth | Substituted sulfonamide-indoles |
| US20050215626A1 (en) * | 2003-09-25 | 2005-09-29 | Wyeth | Substituted benzofuran oximes |
| US7332521B2 (en) * | 2003-09-25 | 2008-02-19 | Wyeth | Substituted indoles |
| US7141592B2 (en) * | 2003-09-25 | 2006-11-28 | Wyeth | Substituted oxadiazolidinediones |
| US7446201B2 (en) * | 2003-09-25 | 2008-11-04 | Wyeth | Substituted heteroaryl benzofuran acids |
| US7265148B2 (en) * | 2003-09-25 | 2007-09-04 | Wyeth | Substituted pyrrole-indoles |
| CN101044127A (zh) | 2004-08-23 | 2007-09-26 | 惠氏公司 | 用作纤溶酶原激活剂抑制剂－1的噻唑基－萘基酸 |
| AU2005277137A1 (en) * | 2004-08-23 | 2006-03-02 | Wyeth | Pyrrolo-naphthyl acids as PAI-1 inhibitors |
| WO2006023865A1 (en) * | 2004-08-23 | 2006-03-02 | Wyeth | Oxazolo-naphthyl acids as plaminogen activator inhibtor type-1 (pai-1) modulators useful in the treatment of thrombosis and cardiovascular diseases |
| BRPI0614340A2 (pt) * | 2005-08-17 | 2011-04-12 | Wyeth Corp | indóis substituìdos e métodos de seu uso |
| WO2014164704A2 (en) | 2013-03-11 | 2014-10-09 | The Broad Institute, Inc. | Compounds and compositions for the treatment of cancer |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322786A (en) * | 1965-10-07 | 1967-05-30 | Merck & Co Inc | 3-indolyl aliphatic acids |
| US3928380A (en) * | 1973-03-29 | 1975-12-23 | Sterling Drug Inc | 1,1{40 -Spirobis(cyclopenta-{8 4,5-c{9 pyrroles) |
| DE2557341A1 (de) * | 1975-12-19 | 1977-06-30 | Hoechst Ag | Basisch substituierte indolderivate und verfahren zu ihrer herstellung |
| US4144338A (en) * | 1977-02-17 | 1979-03-13 | Merck & Co., Inc. | N-pyrimidinyl-N-dialkylaminoalkyl ureas |
| US4181665A (en) * | 1977-10-31 | 1980-01-01 | The Upjohn Company | Isochroman |
| US4258185A (en) * | 1978-10-17 | 1981-03-24 | Yoshitomi Pharmaceutical Industries, Ltd. | Pyridazinone compounds |
| DE2845220A1 (de) * | 1978-10-17 | 1980-04-30 | Yoshitomi Pharmaceutical | Pyridazinon-derivate, ihre salze mit saeuren, verfahren zu ihrer herstellung und ihre verwendung bei der behandlung von thrombosen und hypertonie |
| EP0052442B1 (en) * | 1980-11-14 | 1985-09-11 | Imperial Chemical Industries Plc | Heterocyclic compounds |
| JPS5785055A (en) * | 1980-11-18 | 1982-05-27 | Konishiroku Photo Ind Co Ltd | Silver halide photographic recording material |
| DE3131146A1 (de) * | 1981-08-06 | 1983-02-24 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue heteroaryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| CA1199027A (en) * | 1981-11-12 | 1986-01-07 | Stuart D. Mills | Heterocyclic derivatives of pyridazinone, thiadiazinone, oxadiazinone and triazinone |
| FR2530246B1 (fr) * | 1982-07-16 | 1985-06-14 | Delalande Sa | Nouveaux derives pyrido indoliniques et pirido indoliques et leurs sels, ainsi que le procede de preparation et l'application en therapeutique de ces derives et sels |
| US4581356A (en) * | 1983-03-22 | 1986-04-08 | Fujisawa Pharmaceutical Co., Ltd. | Triazine derivatives, and pharmaceutical compositions comprising the same |
| US4666902A (en) * | 1983-06-20 | 1987-05-19 | Cassella Aktiengesellschaft | Tetrahydropyridazinone derivatives, processes for their preparation and their use |
| DE3421641A1 (de) * | 1984-06-09 | 1985-12-12 | Merck Patent Gmbh, 6100 Darmstadt | Indolderivate |
| DK623586A (da) * | 1985-12-27 | 1987-06-28 | Eisai Co Ltd | Piperidinderivater eller salte deraf og farmaceutiske kompositioner indeholdende forbindelserne |
-
1985
- 1985-09-05 DE DE19853531658 patent/DE3531658A1/de not_active Withdrawn
-
1986
- 1986-09-01 EP EP86112068A patent/EP0223937B1/de not_active Expired - Lifetime
- 1986-09-01 NZ NZ217419A patent/NZ217419A/xx unknown
- 1986-09-01 AT AT86112068T patent/ATE73797T1/de not_active IP Right Cessation
- 1986-09-01 DE DE8686112068T patent/DE3684415D1/de not_active Expired - Lifetime
- 1986-09-01 IL IL79911A patent/IL79911A/xx unknown
- 1986-09-02 DD DD86294092A patent/DD258229A5/de not_active IP Right Cessation
- 1986-09-02 AU AU62166/86A patent/AU572405B2/en not_active Ceased
- 1986-09-02 DK DK419086A patent/DK419086A/da not_active Application Discontinuation
- 1986-09-02 GR GR862248A patent/GR862248B/el unknown
- 1986-09-04 HU HU863828A patent/HU197000B/hu not_active IP Right Cessation
- 1986-09-04 FI FI863564A patent/FI863564A7/fi not_active Application Discontinuation
- 1986-09-04 ZA ZA866705A patent/ZA866705B/xx unknown
- 1986-09-04 PT PT83310A patent/PT83310B/pt not_active IP Right Cessation
- 1986-09-04 US US06/904,092 patent/US4851406A/en not_active Expired - Fee Related
- 1986-09-05 JP JP61208118A patent/JPS6256486A/ja active Pending
- 1986-09-05 KR KR1019860007440A patent/KR870003099A/ko not_active Withdrawn
- 1986-09-05 ES ES8601651A patent/ES2001936A6/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI863564A7 (fi) | 1987-03-06 |
| DK419086D0 (da) | 1986-09-02 |
| PT83310A (de) | 1986-10-01 |
| HU197000B (en) | 1989-02-28 |
| GR862248B (en) | 1986-12-31 |
| IL79911A (en) | 1991-04-15 |
| DE3531658A1 (de) | 1987-03-12 |
| DE3684415D1 (de) | 1992-04-23 |
| NZ217419A (en) | 1989-03-29 |
| AU6216686A (en) | 1987-03-12 |
| DK419086A (da) | 1987-03-06 |
| EP0223937A1 (de) | 1987-06-03 |
| HUT41770A (en) | 1987-05-28 |
| JPS6256486A (ja) | 1987-03-12 |
| ATE73797T1 (de) | 1992-04-15 |
| FI863564A0 (fi) | 1986-09-04 |
| IL79911A0 (en) | 1986-12-31 |
| ZA866705B (en) | 1987-04-29 |
| AU572405B2 (en) | 1988-05-05 |
| PT83310B (pt) | 1989-01-17 |
| KR870003099A (ko) | 1987-04-15 |
| ES2001936A6 (es) | 1988-07-01 |
| US4851406A (en) | 1989-07-25 |
| EP0223937B1 (de) | 1992-03-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |