CA1036596A - Oxazinoindole-and thiazinoindole derivatives - Google Patents
Oxazinoindole-and thiazinoindole derivativesInfo
- Publication number
- CA1036596A CA1036596A CA161,193A CA161193A CA1036596A CA 1036596 A CA1036596 A CA 1036596A CA 161193 A CA161193 A CA 161193A CA 1036596 A CA1036596 A CA 1036596A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- dihydro
- indole
- oxazino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- NSKZWNALRFCVML-UHFFFAOYSA-N C1=CC2=NOC=CC2=C2C1=CC=N2.C1=CC2=NSC=CC2=C2C1=CC=N2 Chemical class C1=CC2=NOC=CC2=C2C1=CC=N2.C1=CC2=NSC=CC2=C2C1=CC=N2 NSKZWNALRFCVML-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 160
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 56
- 150000001875 compounds Chemical class 0.000 claims description 297
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 113
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 105
- -1 piperazino, morpholino, piperazino Chemical group 0.000 claims description 87
- 239000002253 acid Substances 0.000 claims description 79
- 150000001412 amines Chemical class 0.000 claims description 72
- 239000003377 acid catalyst Substances 0.000 claims description 62
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 51
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 50
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 50
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 49
- QCDICCVJICKQQI-UHFFFAOYSA-N 2-(3-methylindol-1-yl)ethanol Chemical compound C1=CC=C2C(C)=CN(CCO)C2=C1 QCDICCVJICKQQI-UHFFFAOYSA-N 0.000 claims description 46
- 150000001408 amides Chemical class 0.000 claims description 44
- 239000000126 substance Substances 0.000 claims description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 229910052987 metal hydride Inorganic materials 0.000 claims description 21
- 150000004681 metal hydrides Chemical class 0.000 claims description 21
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 17
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 13
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 claims description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 11
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 9
- 238000007126 N-alkylation reaction Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 7
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 230000009435 amidation Effects 0.000 claims description 6
- 238000007112 amidation reaction Methods 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 150000002923 oximes Chemical class 0.000 claims description 5
- 150000003138 primary alcohols Chemical class 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- QYAHGDMPUORRQD-UHFFFAOYSA-N 4-oxopentyl acetate Chemical compound CC(=O)CCCOC(C)=O QYAHGDMPUORRQD-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- YOFYTIAEHLUATG-UHFFFAOYSA-N 5-(methylamino)pentan-2-one Chemical compound CNCCCC(C)=O YOFYTIAEHLUATG-UHFFFAOYSA-N 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 41
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 12
- NOJNFBUPYOSGTM-UHFFFAOYSA-N 3-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n,n-dimethylpropan-1-amine Chemical compound C1=CC=C2N3CCOC(CCCN(C)C)(C)C3=C(C)C2=C1 NOJNFBUPYOSGTM-UHFFFAOYSA-N 0.000 claims 9
- HUOFUWXIOPKGKB-UHFFFAOYSA-N 3-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n-methylpropan-1-amine Chemical compound C1=CC=C2N3CCOC(CCCNC)(C)C3=C(C)C2=C1 HUOFUWXIOPKGKB-UHFFFAOYSA-N 0.000 claims 8
- WVNRFZNIVDFLFZ-UHFFFAOYSA-N ethyl 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)acetate Chemical group C1=CC=C2N3CCOC(CC(=O)OCC)(C)C3=C(C)C2=C1 WVNRFZNIVDFLFZ-UHFFFAOYSA-N 0.000 claims 8
- YCBXHWWPTZWNCM-UHFFFAOYSA-N ethyl 3-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)propanoate Chemical group C1=CC=C2N3CCOC(CCC(=O)OCC)(C)C3=C(C)C2=C1 YCBXHWWPTZWNCM-UHFFFAOYSA-N 0.000 claims 8
- 239000007800 oxidant agent Substances 0.000 claims 8
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical group CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 6
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 claims 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- GNUXDAZNFMNATG-UHFFFAOYSA-N 3-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)propan-1-amine Chemical compound C1=CC=C2C(C)=C3C(CCCN)(C)OCCN3C2=C1 GNUXDAZNFMNATG-UHFFFAOYSA-N 0.000 claims 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 4
- KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 claims 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 4
- MGPSIDGTLFKDEY-UHFFFAOYSA-N ethyl 5-oxohexanoate Chemical compound CCOC(=O)CCCC(C)=O MGPSIDGTLFKDEY-UHFFFAOYSA-N 0.000 claims 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 3
- GRXACLVKUNDTBZ-UHFFFAOYSA-N 1,10-dimethyl-1-(2-pyrrolidin-1-ylethyl)-3,4-dihydro-[1,4]oxazino[4,3-a]indole Chemical compound C12=CC=CC=C2C(C)=C2N1CCOC2(C)CCN1CCCC1 GRXACLVKUNDTBZ-UHFFFAOYSA-N 0.000 claims 2
- BNQYTYSXALJLPX-UHFFFAOYSA-N 1,10-dimethyl-1-[2-(4-methylpiperazin-1-yl)ethyl]-3,4-dihydro-[1,4]oxazino[4,3-a]indole Chemical compound C1CN(C)CCN1CCC1(C)C2=C(C)C3=CC=CC=C3N2CCO1 BNQYTYSXALJLPX-UHFFFAOYSA-N 0.000 claims 2
- HJIZQWRRMILSFI-UHFFFAOYSA-N 1,10-dimethyl-1-[3-(4-methylpiperazin-1-yl)propyl]-3,4-dihydro-[1,4]oxazino[4,3-a]indole Chemical compound C1CN(C)CCN1CCCC1(C)C2=C(C)C3=CC=CC=C3N2CCO1 HJIZQWRRMILSFI-UHFFFAOYSA-N 0.000 claims 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 2
- VQOCGOITDGGAPS-UHFFFAOYSA-N 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n,n-diethylethanamine Chemical compound C1=CC=C2N3CCOC(CCN(CC)CC)(C)C3=C(C)C2=C1 VQOCGOITDGGAPS-UHFFFAOYSA-N 0.000 claims 2
- HCXPSQZGBNZUHH-UHFFFAOYSA-N 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n-ethylethanamine Chemical compound C1=CC=C2N3CCOC(CCNCC)(C)C3=C(C)C2=C1 HCXPSQZGBNZUHH-UHFFFAOYSA-N 0.000 claims 2
- MZBUWOBDRGRXBC-UHFFFAOYSA-N 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)ethanamine Chemical group C1=CC=C2C(C)=C3C(CCN)(C)OCCN3C2=C1 MZBUWOBDRGRXBC-UHFFFAOYSA-N 0.000 claims 2
- VNLUDHLMJQGKQM-UHFFFAOYSA-N 3-(10-ethyl-1-methyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n-methylpropan-1-amine Chemical compound C1=CC=C2C(CC)=C3C(CCCNC)(C)OCCN3C2=C1 VNLUDHLMJQGKQM-UHFFFAOYSA-N 0.000 claims 2
- JSSRPIIRNHYUND-UHFFFAOYSA-N 4-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n-methylbutan-1-amine Chemical compound C1=CC=C2N3CCOC(CCCCNC)(C)C3=C(C)C2=C1 JSSRPIIRNHYUND-UHFFFAOYSA-N 0.000 claims 2
- XVRIEWDDMODMGA-UHFFFAOYSA-N 5-chloropentan-2-one Chemical compound CC(=O)CCCCl XVRIEWDDMODMGA-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- 239000002262 Schiff base Substances 0.000 claims 2
- 150000004753 Schiff bases Chemical class 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 230000002140 halogenating effect Effects 0.000 claims 2
- 229940102396 methyl bromide Drugs 0.000 claims 2
- 229940050176 methyl chloride Drugs 0.000 claims 2
- MDMUXLSAMUQPDS-UHFFFAOYSA-N n-methyl-2-(10-methyl-1-propyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)ethanamine Chemical compound C1=CC=C2N3CCOC(CCC)(CCNC)C3=C(C)C2=C1 MDMUXLSAMUQPDS-UHFFFAOYSA-N 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- MKDGKNQPZHELSR-UHFFFAOYSA-N 1,10-dimethyl-1-(2-morpholin-4-ylethyl)-3,4-dihydro-[1,4]oxazino[4,3-a]indole Chemical compound C12=CC=CC=C2C(C)=C2N1CCOC2(C)CCN1CCOCC1 MKDGKNQPZHELSR-UHFFFAOYSA-N 0.000 claims 1
- GYNVMMXZHSRQIP-UHFFFAOYSA-N 1,10-dimethyl-1-(2-piperidin-1-ylethyl)-3,4-dihydro-[1,4]oxazino[4,3-a]indole Chemical compound C12=CC=CC=C2C(C)=C2N1CCOC2(C)CCN1CCCCC1 GYNVMMXZHSRQIP-UHFFFAOYSA-N 0.000 claims 1
- HJPWWUZRYSJMCM-UHFFFAOYSA-N 1,10-dimethyl-1-(3-nitropropyl)-3,4-dihydro-[1,4]oxazino[4,3-a]indole Chemical group CC1(OCCN2C1=C(C=1C=CC=CC21)C)CCC[N+](=O)[O-] HJPWWUZRYSJMCM-UHFFFAOYSA-N 0.000 claims 1
- GZCXYFTWJFEPIM-UHFFFAOYSA-N 1,10-dimethyl-1-(3-piperidin-1-ylpropyl)-3,4-dihydro-[1,4]oxazino[4,3-a]indole Chemical compound C12=CC=CC=C2C(C)=C2N1CCOC2(C)CCCN1CCCCC1 GZCXYFTWJFEPIM-UHFFFAOYSA-N 0.000 claims 1
- DJPWWCVPNPVFOA-UHFFFAOYSA-N 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-1-(4-methylpiperazin-1-yl)ethanone Chemical group C1CN(C)CCN1C(=O)CC1(C)C2=C(C)C3=CC=CC=C3N2CCO1 DJPWWCVPNPVFOA-UHFFFAOYSA-N 0.000 claims 1
- UAEZBPCTIFICDR-UHFFFAOYSA-N 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-1-pyrrolidin-1-ylethanone Chemical group C12=CC=CC=C2C(C)=C2N1CCOC2(C)CC(=O)N1CCCC1 UAEZBPCTIFICDR-UHFFFAOYSA-N 0.000 claims 1
- KLAOZAWNQBURGT-UHFFFAOYSA-N 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n,n-diethylacetamide Chemical group C1=CC=C2N3CCOC(CC(=O)N(CC)CC)(C)C3=C(C)C2=C1 KLAOZAWNQBURGT-UHFFFAOYSA-N 0.000 claims 1
- CBULJKWJBOAMRE-UHFFFAOYSA-N 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n,n-dimethylacetamide Chemical group C1=CC=C2N3CCOC(CC(=O)N(C)C)(C)C3=C(C)C2=C1 CBULJKWJBOAMRE-UHFFFAOYSA-N 0.000 claims 1
- PGVDVKDLPXJDGI-UHFFFAOYSA-N 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n-ethylacetamide Chemical group C1=CC=C2N3CCOC(CC(=O)NCC)(C)C3=C(C)C2=C1 PGVDVKDLPXJDGI-UHFFFAOYSA-N 0.000 claims 1
- JRYICBKBQQSDER-UHFFFAOYSA-N 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n-methylacetamide Chemical group C1=CC=C2N3CCOC(CC(=O)NC)(C)C3=C(C)C2=C1 JRYICBKBQQSDER-UHFFFAOYSA-N 0.000 claims 1
- HFRMXRWHDPEKCC-UHFFFAOYSA-N 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n-methylethanamine Chemical compound C1=CC=C2N3CCOC(CCNC)(C)C3=C(C)C2=C1 HFRMXRWHDPEKCC-UHFFFAOYSA-N 0.000 claims 1
- YUNAQCLYQXINHD-UHFFFAOYSA-N 2-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)acetamide Chemical group C1=CC=C2C(C)=C3C(CC(N)=O)(C)OCCN3C2=C1 YUNAQCLYQXINHD-UHFFFAOYSA-N 0.000 claims 1
- GKIDSGKLNGBHAB-UHFFFAOYSA-N 2-(3-ethylindol-1-yl)ethanol Chemical compound C(C)C1=CN(C2=CC=CC=C12)CCO GKIDSGKLNGBHAB-UHFFFAOYSA-N 0.000 claims 1
- CNLPRDWYSPNZCZ-UHFFFAOYSA-N 3-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n-ethylpropan-1-amine Chemical compound C1=CC=C2N3CCOC(CCCNCC)(C)C3=C(C)C2=C1 CNLPRDWYSPNZCZ-UHFFFAOYSA-N 0.000 claims 1
- HOFUXAVDJWRFQZ-UHFFFAOYSA-N 3-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)propanoic acid Chemical group C1=CC=C2C(C)=C3C(CCC(O)=O)(C)OCCN3C2=C1 HOFUXAVDJWRFQZ-UHFFFAOYSA-N 0.000 claims 1
- VITGGSSBWKUFGR-UHFFFAOYSA-N 3-indol-1-ylpropanamide Chemical compound C1=CC=C2N(CCC(=O)N)C=CC2=C1 VITGGSSBWKUFGR-UHFFFAOYSA-N 0.000 claims 1
- NWCYECXHIYEBJE-UHFFFAOYSA-N 3-oxobutyl acetate Chemical compound CC(=O)CCOC(C)=O NWCYECXHIYEBJE-UHFFFAOYSA-N 0.000 claims 1
- FDWXBWXTQDHGAC-UHFFFAOYSA-N 4-(1,10-dimethyl-3,4-dihydro-[1,4]oxazino[4,3-a]indol-1-yl)-n-ethylbutan-1-amine Chemical compound C1=CC=C2N3CCOC(CCCCNCC)(C)C3=C(C)C2=C1 FDWXBWXTQDHGAC-UHFFFAOYSA-N 0.000 claims 1
- WQVAMFRPCWXWSS-UHFFFAOYSA-N 4-(dimethylamino)butan-2-one Chemical compound CN(C)CCC(C)=O WQVAMFRPCWXWSS-UHFFFAOYSA-N 0.000 claims 1
- MAGOYBJJLVSJIC-UHFFFAOYSA-N 4-chlorobutan-2-one Chemical compound CC(=O)CCCl MAGOYBJJLVSJIC-UHFFFAOYSA-N 0.000 claims 1
- ZZUHQGCKXVUCFZ-UHFFFAOYSA-N 4-nitrobutan-2-one Chemical compound CC(=O)CC[N+]([O-])=O ZZUHQGCKXVUCFZ-UHFFFAOYSA-N 0.000 claims 1
- HCRLXYVAWDRFBV-UHFFFAOYSA-N 5-(dimethylamino)pentan-2-one Chemical compound CN(C)CCCC(C)=O HCRLXYVAWDRFBV-UHFFFAOYSA-N 0.000 claims 1
- MBFOTTCUUAIBDW-UHFFFAOYSA-N 5-nitropentan-2-one Chemical compound CC(=O)CCC[N+]([O-])=O MBFOTTCUUAIBDW-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
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- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 101150084216 thiB gene Proteins 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00226287A US3833575A (en) | 1972-02-14 | 1972-02-14 | Oxazinoindole-and thiazinoindole derivatives |
| US297130A US3904617A (en) | 1972-10-12 | 1972-10-12 | Process for preparing new heterocyclic derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1036596A true CA1036596A (en) | 1978-08-15 |
Family
ID=26920388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA161,193A Expired CA1036596A (en) | 1972-02-14 | 1973-01-12 | Oxazinoindole-and thiazinoindole derivatives |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4886895A (en:Method) |
| CA (1) | CA1036596A (en:Method) |
| DE (1) | DE2306809A1 (en:Method) |
| FR (1) | FR2181727B1 (en:Method) |
| GB (1) | GB1421063A (en:Method) |
| IE (1) | IE37234B1 (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU190458B (en) * | 1983-10-25 | 1986-09-29 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing /1,3/ oxazino /4,3-a/ isoquinoline-derivatives |
| HU191301B (en) * | 1984-03-23 | 1987-02-27 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing 1-/hydroxy-methyl/-1,6,7,11b-tetrahydro-2h,4h-/1,3/-oxazino- or -thiazino/4,3-a/isoquinoline -derivatives |
| TW270114B (en:Method) * | 1993-10-22 | 1996-02-11 | Hoffmann La Roche |
-
1972
- 1972-12-19 IE IE176872A patent/IE37234B1/xx unknown
-
1973
- 1973-01-12 CA CA161,193A patent/CA1036596A/en not_active Expired
- 1973-02-12 DE DE19732306809 patent/DE2306809A1/de active Pending
- 1973-02-13 JP JP48019694A patent/JPS4886895A/ja active Pending
- 1973-02-13 FR FR7305071A patent/FR2181727B1/fr not_active Expired
- 1973-02-13 GB GB688373A patent/GB1421063A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2181727B1 (en:Method) | 1976-10-22 |
| FR2181727A1 (en:Method) | 1973-12-07 |
| GB1421063A (en) | 1976-01-14 |
| IE37234L (en) | 1973-08-14 |
| IE37234B1 (en) | 1977-06-08 |
| JPS4886895A (en:Method) | 1973-11-15 |
| DE2306809A1 (de) | 1973-08-30 |
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