FI64590C - Analogifoerfarande foer framstaellning av terapeutiskt aktiva indoler - Google Patents
Analogifoerfarande foer framstaellning av terapeutiskt aktiva indoler Download PDFInfo
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- FI64590C FI64590C FI753669A FI753669A FI64590C FI 64590 C FI64590 C FI 64590C FI 753669 A FI753669 A FI 753669A FI 753669 A FI753669 A FI 753669A FI 64590 C FI64590 C FI 64590C
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- 230000001225 therapeutic effect Effects 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 102
- -1 C 1 -C 6 alkoxyalkyl Chemical group 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 239000002585 base Substances 0.000 claims description 21
- 239000003960 organic solvent Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000012458 free base Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002475 indoles Chemical class 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- JMSVCTWVEWCHDZ-UHFFFAOYSA-M syringate Chemical class COC1=CC(C([O-])=O)=CC(OC)=C1O JMSVCTWVEWCHDZ-UHFFFAOYSA-M 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
- 239000000243 solution Substances 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 47
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 23
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- 238000012360 testing method Methods 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 241000700159 Rattus Species 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- NYJACYLXVJMNOM-UHFFFAOYSA-N 2-(1h-indol-3-ylsulfanyl)acetonitrile Chemical compound C1=CC=C2C(SCC#N)=CNC2=C1 NYJACYLXVJMNOM-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 239000003637 basic solution Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 230000000747 cardiac effect Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 3
- 229930182837 (R)-adrenaline Natural products 0.000 description 3
- KFHKQNPSQKPULZ-UHFFFAOYSA-N 2-(1-methylindol-3-yl)sulfanylacetonitrile Chemical compound C1=CC=C2N(C)C=C(SCC#N)C2=C1 KFHKQNPSQKPULZ-UHFFFAOYSA-N 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 210000001015 abdomen Anatomy 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- PECIYKGSSMCNHN-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=NC=N[C]21.O=C1N(C)C(=O)N(C)C2=NC=N[C]21 PECIYKGSSMCNHN-UHFFFAOYSA-N 0.000 description 3
- 229960003556 aminophylline Drugs 0.000 description 3
- 230000037005 anaesthesia Effects 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 230000004872 arterial blood pressure Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- SKJFTWMIXZFOBU-UHFFFAOYSA-N but-2-enedioic acid;1h-indole Chemical compound OC(=O)C=CC(O)=O.C1=CC=C2NC=CC2=C1 SKJFTWMIXZFOBU-UHFFFAOYSA-N 0.000 description 3
- 229960001948 caffeine Drugs 0.000 description 3
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- 239000013078 crystal Substances 0.000 description 3
- 229960005139 epinephrine Drugs 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- SKJFTWMIXZFOBU-WLHGVMLRSA-N (e)-but-2-enedioic acid;1h-indole Chemical compound OC(=O)\C=C\C(O)=O.C1=CC=C2NC=CC2=C1 SKJFTWMIXZFOBU-WLHGVMLRSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HJLJWGUVEDDGJZ-UHFFFAOYSA-N 1-(1h-indol-3-ylsulfanyl)propan-2-amine Chemical compound C1=CC=C2C(SCC(N)C)=CNC2=C1 HJLJWGUVEDDGJZ-UHFFFAOYSA-N 0.000 description 2
- ACDCKENQGVJWQI-UHFFFAOYSA-N 1H-indol-2-ylcarbamothioylazanium iodide Chemical compound [I-].N1C(=CC2=CC=CC=C12)NC(=[NH2+])S ACDCKENQGVJWQI-UHFFFAOYSA-N 0.000 description 2
- RZCPVVSHZUUUCW-UHFFFAOYSA-N 2-(1h-indol-3-ylsulfanyl)ethanamine Chemical compound C1=CC=C2C(SCCN)=CNC2=C1 RZCPVVSHZUUUCW-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 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
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- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
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- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
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- RJTZUHVCZIGJMB-UHFFFAOYSA-N hydron;1h-indole;chloride Chemical compound Cl.C1=CC=C2NC=CC2=C1 RJTZUHVCZIGJMB-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
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- VYIGETPDYVCSDM-UHFFFAOYSA-N n-(2-chloroethyl)-3,4-dihydro-2h-pyrrol-5-amine Chemical compound ClCCN=C1CCCN1 VYIGETPDYVCSDM-UHFFFAOYSA-N 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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- OJYGBLRPYBAHRT-GVUNPQSCSA-N (1r)-1-[(2s,3ar,5r,6s,6ar)-6-hydroxy-2-(trichloromethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol Chemical compound O1[C@@H](C(Cl)(Cl)Cl)O[C@@H]2[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]21 OJYGBLRPYBAHRT-GVUNPQSCSA-N 0.000 description 1
- MLIWQXBKMZNZNF-KUHOPJCQSA-N (2e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-KUHOPJCQSA-N 0.000 description 1
- YLXIPWWIOISBDD-NDAAPVSOSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;4-[(1r)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.CNC[C@H](O)C1=CC=C(O)C(O)=C1 YLXIPWWIOISBDD-NDAAPVSOSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 1
- CBXYRDIMGFMFBQ-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(1-methylindol-3-yl)sulfanylethanamine Chemical compound OC(=O)\C=C\C(O)=O.C1=CC=C2N(C)C=C(SCCN)C2=C1 CBXYRDIMGFMFBQ-WLHGVMLRSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53761274A | 1974-12-30 | 1974-12-30 | |
| US53761274 | 1974-12-30 | ||
| US63179875A | 1975-11-13 | 1975-11-13 | |
| US63179875 | 1975-11-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI753669A7 FI753669A7 (de) | 1976-07-01 |
| FI64590B FI64590B (fi) | 1983-08-31 |
| FI64590C true FI64590C (fi) | 1983-12-12 |
Family
ID=27065555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI753669A FI64590C (fi) | 1974-12-30 | 1975-12-29 | Analogifoerfarande foer framstaellning av terapeutiskt aktiva indoler |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS51131872A (de) |
| AR (1) | AR219052A1 (de) |
| AT (1) | AT356648B (de) |
| AU (1) | AU505215B2 (de) |
| CA (1) | CA1065874A (de) |
| CH (1) | CH622516A5 (de) |
| DD (1) | DD125781A5 (de) |
| DE (1) | DE2559211A1 (de) |
| DK (1) | DK580175A (de) |
| ES (1) | ES443935A1 (de) |
| FI (1) | FI64590C (de) |
| FR (2) | FR2296413A1 (de) |
| GB (1) | GB1527510A (de) |
| HU (2) | HU174948B (de) |
| IE (1) | IE42390B1 (de) |
| IL (1) | IL48756A (de) |
| IN (1) | IN142735B (de) |
| IT (1) | IT1052654B (de) |
| NL (1) | NL7515100A (de) |
| NO (1) | NO145383C (de) |
| NZ (1) | NZ179580A (de) |
| PH (1) | PH12328A (de) |
| PL (1) | PL99353B1 (de) |
| RO (1) | RO69196A (de) |
| SE (1) | SE422210B (de) |
| SU (1) | SU667132A3 (de) |
| YU (1) | YU332275A (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1595056A (en) * | 1976-10-12 | 1981-08-05 | Wellcome Found | Pharmaceutical combination |
| FR2540109B1 (fr) * | 1983-01-28 | 1985-08-30 | Logeais Labor Jacques | Imino-2 pyrrolidines, leur procede de preparation et leurs applications en therapeutique |
| US4558048A (en) * | 1984-04-06 | 1985-12-10 | Pfizer Inc. | Method of treating diarrhoea using indole compounds |
| WO2001023350A1 (fr) * | 1999-09-28 | 2001-04-05 | Nihon Nohyaku Co., Ltd. | Derives de thioalkylamine et methode de preparation desdits derives |
| UA79504C2 (en) * | 2002-11-07 | 2007-06-25 | Organon Nv | Indols for treating diseases associated with androgen receptors |
| MXPA05004929A (es) | 2002-11-07 | 2005-08-18 | Akzo Nobel Nv | Indoles utiles en el tratamiento de enfermedades relacionadas a receptor de androgeno. |
| TW200602317A (en) | 2004-04-23 | 2006-01-16 | Akzo Nobel Nv | Novel androgens |
| WO2007020653A1 (en) * | 2005-08-12 | 2007-02-22 | Suven Life Sciences Limited | Thioether derivatives as functional 5-ht6 ligands |
-
1975
- 1975-12-17 NZ NZ179580A patent/NZ179580A/xx unknown
- 1975-12-17 IN IN2354/CAL/75A patent/IN142735B/en unknown
- 1975-12-18 NO NO754313A patent/NO145383C/no unknown
- 1975-12-19 DK DK580175A patent/DK580175A/da not_active Application Discontinuation
- 1975-12-19 SE SE7514458A patent/SE422210B/xx unknown
- 1975-12-24 CH CH1679775A patent/CH622516A5/de not_active IP Right Cessation
- 1975-12-24 NL NL7515100A patent/NL7515100A/xx not_active Application Discontinuation
- 1975-12-26 JP JP50155154A patent/JPS51131872A/ja active Pending
- 1975-12-29 GB GB53024/75A patent/GB1527510A/en not_active Expired
- 1975-12-29 IT IT7552899A patent/IT1052654B/it active
- 1975-12-29 ES ES443935A patent/ES443935A1/es not_active Expired
- 1975-12-29 AT AT986075A patent/AT356648B/de not_active IP Right Cessation
- 1975-12-29 DD DD190619A patent/DD125781A5/xx unknown
- 1975-12-29 IL IL48756A patent/IL48756A/xx unknown
- 1975-12-29 RO RO7584353A patent/RO69196A/ro unknown
- 1975-12-29 FI FI753669A patent/FI64590C/fi not_active IP Right Cessation
- 1975-12-29 YU YU03322/75A patent/YU332275A/xx unknown
- 1975-12-29 PH PH7517930A patent/PH12328A/en unknown
- 1975-12-29 CA CA242,669A patent/CA1065874A/en not_active Expired
- 1975-12-30 AR AR261797A patent/AR219052A1/es active
- 1975-12-30 PL PL1975186097A patent/PL99353B1/pl unknown
- 1975-12-30 SU SU752307502A patent/SU667132A3/ru active
- 1975-12-30 IE IE2830/75A patent/IE42390B1/en unknown
- 1975-12-30 AU AU87916/75A patent/AU505215B2/en not_active Expired
- 1975-12-30 HU HU75ME1936A patent/HU174948B/hu unknown
- 1975-12-30 HU HU75ME2020A patent/HU174949B/hu unknown
- 1975-12-30 DE DE19752559211 patent/DE2559211A1/de not_active Ceased
- 1975-12-30 FR FR7540132A patent/FR2296413A1/fr active Granted
-
1976
- 1976-08-30 FR FR7626153A patent/FR2315921A1/fr active Granted
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: MCNEIL LABORATORIES INC. |