CH605959A5 - (thio)pyrano-indole derivs - Google Patents
(thio)pyrano-indole derivsInfo
- Publication number
- CH605959A5 CH605959A5 CH48773A CH48773A CH605959A5 CH 605959 A5 CH605959 A5 CH 605959A5 CH 48773 A CH48773 A CH 48773A CH 48773 A CH48773 A CH 48773A CH 605959 A5 CH605959 A5 CH 605959A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- formula
- indole
- methyl
- dimethyl
- Prior art date
Links
- ROUYSXBEYWORTN-UHFFFAOYSA-N thiopyrano[2,3-g]indole Chemical compound S1C=CC=C2C3=NC=CC3=CC=C21 ROUYSXBEYWORTN-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 173
- -1 hydroxy, mercapto Chemical class 0.000 claims description 110
- 238000000034 method Methods 0.000 claims description 102
- 229910052757 nitrogen Inorganic materials 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000003377 acid catalyst Substances 0.000 claims description 16
- 125000004423 acyloxy group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 239000000935 antidepressant agent Substances 0.000 abstract description 7
- 229940005513 antidepressants Drugs 0.000 abstract description 7
- 230000001430 anti-depressive effect Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 230000000767 anti-ulcer Effects 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 163
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 150
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 145
- 239000007858 starting material Substances 0.000 description 126
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 119
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 97
- 239000000243 solution Substances 0.000 description 96
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
- 239000000047 product Substances 0.000 description 73
- 150000003839 salts Chemical class 0.000 description 68
- 239000000203 mixture Substances 0.000 description 67
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 238000002844 melting Methods 0.000 description 60
- 230000008018 melting Effects 0.000 description 60
- 238000005481 NMR spectroscopy Methods 0.000 description 50
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 48
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 47
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 40
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 37
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- 238000001953 recrystallisation Methods 0.000 description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 30
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 30
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
- 150000001412 amines Chemical class 0.000 description 29
- 150000002148 esters Chemical class 0.000 description 29
- 239000002253 acid Substances 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 239000012280 lithium aluminium hydride Substances 0.000 description 27
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
- 229910052938 sodium sulfate Inorganic materials 0.000 description 26
- 235000011152 sodium sulphate Nutrition 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 24
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 24
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 24
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- 235000019341 magnesium sulphate Nutrition 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000003921 oil Substances 0.000 description 21
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 19
- 150000001408 amides Chemical class 0.000 description 18
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 18
- MBBOMCVGYCRMEA-UHFFFAOYSA-N tryptophol Chemical compound C1=CC=C2C(CCO)=CNC2=C1 MBBOMCVGYCRMEA-UHFFFAOYSA-N 0.000 description 18
- 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 17
- 239000000543 intermediate Substances 0.000 description 17
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Chemical compound C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 229910052708 sodium Inorganic materials 0.000 description 14
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 13
- 239000008346 aqueous phase Substances 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 235000017557 sodium bicarbonate Nutrition 0.000 description 13
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 12
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 12
- 229940080818 propionamide Drugs 0.000 description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- 239000002243 precursor Substances 0.000 description 11
- QCDICCVJICKQQI-UHFFFAOYSA-N 2-(3-methylindol-1-yl)ethanol Chemical compound C1=CC=C2C(C)=CN(CCO)C2=C1 QCDICCVJICKQQI-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000003513 alkali Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000011976 maleic acid Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 10
- KKZPDPNTMKHMNU-UHFFFAOYSA-N 3-(2-bromoethyl)-1h-indene Chemical class C1=CC=C2C(CCBr)=CCC2=C1 KKZPDPNTMKHMNU-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 9
- 150000004678 hydrides Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- NFWOMTTZUPDDOK-UHFFFAOYSA-N 2-(3h-inden-1-yl)ethanol Chemical compound C1=CC=C2C(CCO)=CCC2=C1 NFWOMTTZUPDDOK-UHFFFAOYSA-N 0.000 description 8
- IUUZMSMGSOUFTO-UHFFFAOYSA-N 2-indol-1-ylacetamide Chemical compound C1=CC=C2N(CC(=O)N)C=CC2=C1 IUUZMSMGSOUFTO-UHFFFAOYSA-N 0.000 description 8
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 8
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 239000012258 stirred mixture Substances 0.000 description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 description 8
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 7
- 125000005907 alkyl ester group Chemical group 0.000 description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 7
- 239000012259 ether extract Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 229940074386 skatole Drugs 0.000 description 7
- SVQCZHOYIDFGAH-UHFFFAOYSA-N 1,3,4,4a-tetrahydropyrano[3,4-b]indole Chemical compound C1=CC=C2C3CCOCC3=NC2=C1 SVQCZHOYIDFGAH-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 150000001722 carbon compounds Chemical class 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000002808 molecular sieve Substances 0.000 description 6
- 235000006408 oxalic acid Nutrition 0.000 description 6
- 235000019260 propionic acid Nutrition 0.000 description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 6
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
- UTUFVOGCRYIYHO-UHFFFAOYSA-N 2-(1-methyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)acetic acid Chemical compound N1C2=CC=CC=C2C2=C1C(C)(CC(O)=O)OCC2 UTUFVOGCRYIYHO-UHFFFAOYSA-N 0.000 description 5
- HTXWKZDRDRFVHN-UHFFFAOYSA-N 2-methyloxiran-2-ol Chemical compound CC1(O)CO1 HTXWKZDRDRFVHN-UHFFFAOYSA-N 0.000 description 5
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 150000003857 carboxamides Chemical class 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 4
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- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- VHAXQSFPTJUMLT-UHFFFAOYSA-N bis(3-methylbutan-2-yl)boron Chemical compound CC(C)C(C)[B]C(C)C(C)C VHAXQSFPTJUMLT-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UTCFREZFQSHYLP-UHFFFAOYSA-N dimethyl(3-oxobutyl)azanium;chloride Chemical compound Cl.CN(C)CCC(C)=O UTCFREZFQSHYLP-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical group CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- WVNRFZNIVDFLFZ-UHFFFAOYSA-N ethyl 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)acetate Chemical compound C1=CC=C2N3CCOC(CC(=O)OCC)(C)C3=C(C)C2=C1 WVNRFZNIVDFLFZ-UHFFFAOYSA-N 0.000 description 1
- FVHZAUFNFDXHTQ-UHFFFAOYSA-N ethyl 2-(3-methylindol-1-yl)acetate Chemical compound C1=CC=C2N(CC(=O)OCC)C=C(C)C2=C1 FVHZAUFNFDXHTQ-UHFFFAOYSA-N 0.000 description 1
- VGFGMNSKSUCONE-UHFFFAOYSA-N ethyl 3-indol-1-ylpropanoate Chemical compound C1=CC=C2N(CCC(=O)OCC)C=CC2=C1 VGFGMNSKSUCONE-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- KEBJNFBBNGKUMX-UHFFFAOYSA-N methyl 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)acetate Chemical compound C1=CC=C2N3CCOC(CC(=O)OC)(C)C3=C(C)C2=C1 KEBJNFBBNGKUMX-UHFFFAOYSA-N 0.000 description 1
- AFOFTSBHECYADG-UHFFFAOYSA-N methyl 2-(1-methyl-4,9-dihydro-3h-indeno[2,1-c]pyran-1-yl)acetate Chemical compound C1C2=CC=CC=C2C2=C1C(CC(=O)OC)(C)OCC2 AFOFTSBHECYADG-UHFFFAOYSA-N 0.000 description 1
- JLAPTBPTXYWIEN-UHFFFAOYSA-N methyl 2-(1-methyl-4,9-dihydro-3h-indeno[2,1-c]thiopyran-1-yl)acetate Chemical compound C1C2=CC=CC=C2C2=C1C(CC(=O)OC)(C)SCC2 JLAPTBPTXYWIEN-UHFFFAOYSA-N 0.000 description 1
- IDAQIDOWVXONAN-UHFFFAOYSA-N methyl 2-(1-methyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)acetate Chemical compound N1C2=CC=CC=C2C2=C1C(CC(=O)OC)(C)OCC2 IDAQIDOWVXONAN-UHFFFAOYSA-N 0.000 description 1
- GFKHDXHWUGIVBE-UHFFFAOYSA-N methyl 2-(1-methyl-4,9-dihydro-3h-thiopyrano[3,4-b]indol-1-yl)acetate Chemical compound N1C2=CC=CC=C2C2=C1C(CC(=O)OC)(C)SCC2 GFKHDXHWUGIVBE-UHFFFAOYSA-N 0.000 description 1
- URXFAMDQERDBFY-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate;1-methyl-1,3,4,9-tetrahydroindeno[2,1-c]pyran Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1.C1C2=CC=CC=C2C2=C1C(C)OCC2 URXFAMDQERDBFY-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- GHFIYNHDQCRRFT-UHFFFAOYSA-N n,n-diethyl-2-(1-methyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)acetamide Chemical compound N1C2=CC=CC=C2C2=C1C(CC(=O)N(CC)CC)(C)OCC2 GHFIYNHDQCRRFT-UHFFFAOYSA-N 0.000 description 1
- PVSONWIOQKVHSI-UHFFFAOYSA-N n,n-diethyl-2-(1-methyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)ethanamine Chemical compound N1C2=CC=CC=C2C2=C1C(CCN(CC)CC)(C)OCC2 PVSONWIOQKVHSI-UHFFFAOYSA-N 0.000 description 1
- DDUKEURYFNBEFV-UHFFFAOYSA-N n,n-dimethyl-2-(1-methyl-4,9-dihydro-3h-indeno[2,1-c]thiopyran-1-yl)ethanamine Chemical compound C1C2=CC=CC=C2C2=C1C(CCN(C)C)(C)SCC2 DDUKEURYFNBEFV-UHFFFAOYSA-N 0.000 description 1
- JKKHZEVHQJZTNQ-UHFFFAOYSA-N n,n-dimethyl-2-oxopropanamide Chemical compound CN(C)C(=O)C(C)=O JKKHZEVHQJZTNQ-UHFFFAOYSA-N 0.000 description 1
- YPEWWOUWRRQBAX-UHFFFAOYSA-N n,n-dimethyl-3-oxobutanamide Chemical compound CN(C)C(=O)CC(C)=O YPEWWOUWRRQBAX-UHFFFAOYSA-N 0.000 description 1
- SICIPBMLFSQZEQ-UHFFFAOYSA-N n-(2-oxopropyl)acetamide Chemical compound CC(=O)CNC(C)=O SICIPBMLFSQZEQ-UHFFFAOYSA-N 0.000 description 1
- CAQXYVTYTTXGKW-UHFFFAOYSA-N n-(2-oxopropyl)formamide Chemical compound CC(=O)CNC=O CAQXYVTYTTXGKW-UHFFFAOYSA-N 0.000 description 1
- HJSYCVYFTIIOPM-UHFFFAOYSA-N n-(4-oxopentyl)acetamide Chemical compound CC(=O)CCCNC(C)=O HJSYCVYFTIIOPM-UHFFFAOYSA-N 0.000 description 1
- OYMZZUUNRPGOFF-UHFFFAOYSA-N n-[(1-methyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)methyl]acetamide Chemical compound N1C2=CC=CC=C2C2=C1C(CNC(=O)C)(C)OCC2 OYMZZUUNRPGOFF-UHFFFAOYSA-N 0.000 description 1
- HORVOSLOFGUWNL-UHFFFAOYSA-N n-[(1-methyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)methyl]ethanamine;hydrochloride Chemical compound Cl.N1C2=CC=CC=C2C2=C1C(CNCC)(C)OCC2 HORVOSLOFGUWNL-UHFFFAOYSA-N 0.000 description 1
- WGZKFAQMHXHLIX-UHFFFAOYSA-N n-[2-(1-methyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)ethyl]hexan-1-amine Chemical compound N1C2=CC=CC=C2C2=C1C(CCNCCCCCC)(C)OCC2 WGZKFAQMHXHLIX-UHFFFAOYSA-N 0.000 description 1
- OEKPWHVDSBXYED-UHFFFAOYSA-N n-[2-(1-methyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)ethyl]propan-2-amine Chemical compound N1C2=CC=CC=C2C2=C1C(CCNC(C)C)(C)OCC2 OEKPWHVDSBXYED-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JCXPBGJVWJNKKN-UHFFFAOYSA-N n-ethyl-2-(1-methyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)ethanamine Chemical compound N1C2=CC=CC=C2C2=C1C(CCNCC)(C)OCC2 JCXPBGJVWJNKKN-UHFFFAOYSA-N 0.000 description 1
- IPOMZPMUBURYIY-UHFFFAOYSA-N n-methyl-2-(1-methyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)acetamide Chemical compound N1C2=CC=CC=C2C2=C1C(CC(=O)NC)(C)OCC2 IPOMZPMUBURYIY-UHFFFAOYSA-N 0.000 description 1
- RMIQNHMOQHTRQW-UHFFFAOYSA-N n-methyl-3-(1-methyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)propan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.N1C2=CC=CC=C2C2=C1C(CCCNC)(C)OCC2 RMIQNHMOQHTRQW-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- AMJPIGOYWBNJLP-UHFFFAOYSA-N pirandamine Chemical compound C1C2=CC=CC=C2C2=C1C(CCN(C)C)(C)OCC2 AMJPIGOYWBNJLP-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- LSUKIZPWGJLKKZ-UHFFFAOYSA-N propyl 2-(1-methyl-4,9-dihydro-3h-indeno[2,1-c]pyran-1-yl)acetate Chemical compound C1C2=CC=CC=C2C2=C1C(CC(=O)OCCC)(C)OCC2 LSUKIZPWGJLKKZ-UHFFFAOYSA-N 0.000 description 1
- UVLZNQQORZJXKO-UHFFFAOYSA-N propyl 2-(1-methyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)acetate Chemical compound N1C2=CC=CC=C2C2=C1C(CC(=O)OCCC)(C)OCC2 UVLZNQQORZJXKO-UHFFFAOYSA-N 0.000 description 1
- 230000001003 psychopharmacologic effect Effects 0.000 description 1
- ABPJREHLAYHTHW-UHFFFAOYSA-N pyrano[2,3-g]indole Chemical compound O1C=CC=C2C3=NC=CC3=CC=C21 ABPJREHLAYHTHW-UHFFFAOYSA-N 0.000 description 1
- DULBEIKUQPJAST-UHFFFAOYSA-N pyrano[3,4-b]indole Chemical compound O1C=CC2=C3C=CC=CC3=NC2=C1 DULBEIKUQPJAST-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 125000000169 tricyclic heterocycle group Chemical group 0.000 description 1
- 150000004798 β-ketoamides Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/02—Thiols having mercapto groups bound to acyclic carbon atoms
- C07C321/10—Thiols having mercapto groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
-
- 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00217627A US3852285A (en) | 1972-01-13 | 1972-01-13 | Pyrano- and thiopyranoindole derivatives |
| US00226287A US3833575A (en) | 1972-02-14 | 1972-02-14 | Oxazinoindole-and thiazinoindole derivatives |
| US29712972A | 1972-10-12 | 1972-10-12 | |
| US297130A US3904617A (en) | 1972-10-12 | 1972-10-12 | Process for preparing new heterocyclic derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH605959A5 true CH605959A5 (en) | 1978-10-13 |
Family
ID=27499082
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH48773A CH605959A5 (en) | 1972-01-13 | 1973-01-12 | (thio)pyrano-indole derivs |
| CH1530677A CH606030A5 (enrdf_load_html_response) | 1972-01-13 | 1973-01-12 | |
| CH1530777A CH606031A5 (enrdf_load_html_response) | 1972-01-13 | 1973-01-12 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1530677A CH606030A5 (enrdf_load_html_response) | 1972-01-13 | 1973-01-12 | |
| CH1530777A CH606031A5 (enrdf_load_html_response) | 1972-01-13 | 1973-01-12 |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE793978A (enrdf_load_html_response) |
| CH (3) | CH605959A5 (enrdf_load_html_response) |
| DK (1) | DK141201B (enrdf_load_html_response) |
| IL (1) | IL41130A (enrdf_load_html_response) |
| NL (1) | NL7300518A (enrdf_load_html_response) |
| SE (1) | SE392274B (enrdf_load_html_response) |
| SU (1) | SU728716A3 (enrdf_load_html_response) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1683521A1 (en) * | 2005-01-21 | 2006-07-26 | Centre National De La Recherche Scientifique (Cnrs) | Peptide deformylase inhibitors, their use, and pharmaceutical compositions containing the same |
-
0
- BE BE793978D patent/BE793978A/xx not_active IP Right Cessation
-
1972
- 1972-12-20 IL IL41130A patent/IL41130A/en unknown
-
1973
- 1973-01-12 NL NL7300518A patent/NL7300518A/xx not_active Application Discontinuation
- 1973-01-12 CH CH48773A patent/CH605959A5/de not_active IP Right Cessation
- 1973-01-12 CH CH1530677A patent/CH606030A5/xx not_active IP Right Cessation
- 1973-01-12 SU SU731873352A patent/SU728716A3/ru active
- 1973-01-12 CH CH1530777A patent/CH606031A5/xx not_active IP Right Cessation
- 1973-01-12 SE SE7300471A patent/SE392274B/xx unknown
- 1973-01-12 DK DK20973AA patent/DK141201B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH606031A5 (enrdf_load_html_response) | 1978-10-13 |
| SU728716A3 (ru) | 1980-04-15 |
| BE793978A (fr) | 1973-07-12 |
| DK141201B (da) | 1980-02-04 |
| IL41130A (en) | 1976-05-31 |
| CH606030A5 (enrdf_load_html_response) | 1978-10-13 |
| IL41130A0 (en) | 1973-02-28 |
| NL7300518A (enrdf_load_html_response) | 1973-07-17 |
| DK141201C (enrdf_load_html_response) | 1980-07-28 |
| SE392274B (sv) | 1977-03-21 |
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