CA1065874A - 3-substituted indoles and precursors therefor - Google Patents
3-substituted indoles and precursors thereforInfo
- Publication number
- CA1065874A CA1065874A CA242,669A CA242669A CA1065874A CA 1065874 A CA1065874 A CA 1065874A CA 242669 A CA242669 A CA 242669A CA 1065874 A CA1065874 A CA 1065874A
- Authority
- CA
- Canada
- Prior art keywords
- indole
- acid addition
- methyl
- therapeutically active
- active acid
- 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
- -1 3-substituted indoles Chemical class 0.000 title claims abstract description 48
- 239000002243 precursor Substances 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
- 239000004305 biphenyl Substances 0.000 claims abstract description 4
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 134
- 239000002253 acid Substances 0.000 claims description 124
- 150000003839 salts Chemical class 0.000 claims description 124
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 69
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 58
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 39
- 230000008569 process Effects 0.000 claims description 35
- 239000000126 substance Substances 0.000 claims description 35
- 238000004519 manufacturing process Methods 0.000 claims description 34
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 27
- 239000002585 base Substances 0.000 claims description 21
- 239000003960 organic solvent Substances 0.000 claims description 17
- 239000012458 free base Substances 0.000 claims description 16
- RZCPVVSHZUUUCW-UHFFFAOYSA-N 2-(1h-indol-3-ylsulfanyl)ethanamine Chemical compound C1=CC=C2C(SCCN)=CNC2=C1 RZCPVVSHZUUUCW-UHFFFAOYSA-N 0.000 claims description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 10
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 10
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
- RXYRVOTXAHJEAZ-UHFFFAOYSA-N 1-methyl-n-[2-(1-methylindol-3-yl)sulfanylethyl]pyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC1=CN(C)C2=CC=CC=C12 RXYRVOTXAHJEAZ-UHFFFAOYSA-N 0.000 claims description 3
- NAJUALUXJIMLNZ-UHFFFAOYSA-N 2-(1h-indol-2-ylsulfanyl)ethanamine Chemical compound C1=CC=C2NC(SCCN)=CC2=C1 NAJUALUXJIMLNZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- PTFFWCHVBDAOMF-UHFFFAOYSA-N 1-methyl-2-methylsulfanyl-4,5-dihydroimidazole Chemical compound CSC1=NCCN1C PTFFWCHVBDAOMF-UHFFFAOYSA-N 0.000 claims description 2
- TXWCNYYMLZIVMT-UHFFFAOYSA-N 1-methyl-n-[2-[1-(2-methylprop-2-enyl)indol-3-yl]sulfanylethyl]pyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC1=CN(CC(C)=C)C2=CC=CC=C12 TXWCNYYMLZIVMT-UHFFFAOYSA-N 0.000 claims description 2
- LDEALPZWPDFIBH-UHFFFAOYSA-N 2-(1h-indol-2-ylsulfanyl)ethylthiourea Chemical compound C1=CC=C2NC(SCCNC(=S)N)=CC2=C1 LDEALPZWPDFIBH-UHFFFAOYSA-N 0.000 claims description 2
- ZFNRKNCSGAIMAP-UHFFFAOYSA-N 3-(1h-indol-3-ylsulfanyl)propan-1-amine Chemical compound C1=CC=C2C(SCCCN)=CNC2=C1 ZFNRKNCSGAIMAP-UHFFFAOYSA-N 0.000 claims description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 2
- JEXZIPDINVAURS-UHFFFAOYSA-N n-[2-(1h-indol-3-ylsulfanyl)ethyl]-1-methyl-5-phenylpyrrolidin-2-imine Chemical compound C1CC(=NCCSC=2C3=CC=CC=C3NC=2)N(C)C1C1=CC=CC=C1 JEXZIPDINVAURS-UHFFFAOYSA-N 0.000 claims description 2
- KXONXFGXQQWGQE-UHFFFAOYSA-N n-[2-[(5-ethyl-1h-indol-3-yl)sulfanyl]ethyl]-1-methylpyrrolidin-2-imine Chemical compound C12=CC(CC)=CC=C2NC=C1SCCN=C1CCCN1C KXONXFGXQQWGQE-UHFFFAOYSA-N 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- VNWHJJCHHGPAEO-UHFFFAOYSA-N fluoroboronic acid Chemical class OB(O)F VNWHJJCHHGPAEO-UHFFFAOYSA-N 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 3
- NUAPDCJBTTVILP-UHFFFAOYSA-N 1-methyl-n-[2-(1-octylindol-3-yl)sulfanylethyl]pyrrolidin-2-imine Chemical compound C12=CC=CC=C2N(CCCCCCCC)C=C1SCCN=C1CCCN1C NUAPDCJBTTVILP-UHFFFAOYSA-N 0.000 claims 2
- WATJTPAURVJTIL-UHFFFAOYSA-N 1-methyl-n-[2-(1-prop-2-enylindol-3-yl)sulfanylethyl]pyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC1=CN(CC=C)C2=CC=CC=C12 WATJTPAURVJTIL-UHFFFAOYSA-N 0.000 claims 2
- USGUADDJRRJMTD-UHFFFAOYSA-N 1-methyl-n-[2-(1-propylindol-3-yl)sulfanylethyl]pyrrolidin-2-imine Chemical compound C12=CC=CC=C2N(CCC)C=C1SCCN=C1CCCN1C USGUADDJRRJMTD-UHFFFAOYSA-N 0.000 claims 2
- XGNLIUMFTNNCDN-UHFFFAOYSA-N 1-methyl-n-[2-[(2-methyl-1h-indol-3-yl)sulfanyl]ethyl]pyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC1=C(C)NC2=CC=CC=C12 XGNLIUMFTNNCDN-UHFFFAOYSA-N 0.000 claims 2
- PACOFOGXUYPFEE-UHFFFAOYSA-N 1-methyl-n-[2-[(2-phenyl-1h-indol-3-yl)sulfanyl]ethyl]pyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC1=C(C=2C=CC=CC=2)NC2=CC=CC=C12 PACOFOGXUYPFEE-UHFFFAOYSA-N 0.000 claims 2
- JDXBCGVFLCODMT-UHFFFAOYSA-N n-[2-(1-benzylindol-3-yl)sulfanylethyl]-1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC(C1=CC=CC=C11)=CN1CC1=CC=CC=C1 JDXBCGVFLCODMT-UHFFFAOYSA-N 0.000 claims 2
- DZIZSWKLRAMDCE-UHFFFAOYSA-N n-[2-(1-ethylindol-3-yl)sulfanylethyl]-1-methylpyrrolidin-2-imine Chemical compound C12=CC=CC=C2N(CC)C=C1SCCN=C1CCCN1C DZIZSWKLRAMDCE-UHFFFAOYSA-N 0.000 claims 2
- ZVNAAALOGJRJBU-UHFFFAOYSA-N n-[2-(1h-indol-3-ylsulfanyl)ethyl]-1-methyl-4,5-dihydroimidazol-2-amine Chemical compound CN1CCN=C1NCCSC1=CNC2=CC=CC=C12 ZVNAAALOGJRJBU-UHFFFAOYSA-N 0.000 claims 2
- TVKIRHQKMIOXKV-UHFFFAOYSA-N n-[2-(1h-indol-3-ylsulfanyl)ethyl]-1-methylpiperidin-2-imine Chemical compound CN1CCCCC1=NCCSC1=CNC2=CC=CC=C12 TVKIRHQKMIOXKV-UHFFFAOYSA-N 0.000 claims 2
- JGFUFYJQVPUYJW-UHFFFAOYSA-N n-[2-(1h-indol-3-ylsulfanyl)ethyl]-1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC1=CNC2=CC=CC=C12 JGFUFYJQVPUYJW-UHFFFAOYSA-N 0.000 claims 2
- XBVRKYFNRPVVHX-UHFFFAOYSA-N n-[2-(1h-indol-3-ylsulfanyl)ethyl]-1-prop-2-enylpyrrolidin-2-imine Chemical compound C=CCN1CCCC1=NCCSC1=CNC2=CC=CC=C12 XBVRKYFNRPVVHX-UHFFFAOYSA-N 0.000 claims 2
- BVGLPIFIBWECNX-UHFFFAOYSA-N n-[2-(1h-indol-3-ylsulfanyl)ethyl]-3,4-dihydro-2h-pyrrol-5-amine Chemical compound C=1NC2=CC=CC=C2C=1SCCN=C1CCCN1 BVGLPIFIBWECNX-UHFFFAOYSA-N 0.000 claims 2
- RRWMBIGPQXYGDE-UHFFFAOYSA-N n-[2-[(5-chloro-1h-indol-3-yl)sulfanyl]ethyl]-1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC1=CNC2=CC=C(Cl)C=C12 RRWMBIGPQXYGDE-UHFFFAOYSA-N 0.000 claims 2
- RNYDVTBLPFCTQD-UHFFFAOYSA-N n-[2-[(5-methoxy-1h-indol-3-yl)sulfanyl]ethyl]-1-methylpyrrolidin-2-imine Chemical compound C12=CC(OC)=CC=C2NC=C1SCCN=C1CCCN1C RNYDVTBLPFCTQD-UHFFFAOYSA-N 0.000 claims 2
- ZXGOFEDPYQHUCF-UHFFFAOYSA-N n-[2-[1-(2-methoxyethyl)indol-3-yl]sulfanylethyl]-1-methylpyrrolidin-2-imine Chemical compound C12=CC=CC=C2N(CCOC)C=C1SCCN=C1CCCN1C ZXGOFEDPYQHUCF-UHFFFAOYSA-N 0.000 claims 2
- KJGRMOWBXFTNMH-UHFFFAOYSA-N n-[2-[1-(furan-2-ylmethyl)indol-3-yl]sulfanylethyl]-1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC(C1=CC=CC=C11)=CN1CC1=CC=CO1 KJGRMOWBXFTNMH-UHFFFAOYSA-N 0.000 claims 2
- URNLJDXQPLMCDO-UHFFFAOYSA-N n-[3-(1h-indol-3-ylsulfanyl)propyl]-1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=NCCCSC1=CNC2=CC=CC=C12 URNLJDXQPLMCDO-UHFFFAOYSA-N 0.000 claims 2
- YLUCUTOCJNFZDL-UHFFFAOYSA-N 1-(1-methylindol-3-yl)sulfanylpropan-2-amine Chemical compound NC(CSC1=CN(C2=CC=CC=C12)C)C YLUCUTOCJNFZDL-UHFFFAOYSA-N 0.000 claims 1
- CUEHCKZHRICMFY-UHFFFAOYSA-N 1-methyl-5-phenylpyrrolidin-2-one Chemical compound C1CC(=O)N(C)C1C1=CC=CC=C1 CUEHCKZHRICMFY-UHFFFAOYSA-N 0.000 claims 1
- VFOJHMFMHHQHOT-UHFFFAOYSA-N 1-methyl-n-[2-(1-propan-2-ylindol-3-yl)sulfanylethyl]pyrrolidin-2-imine Chemical compound C12=CC=CC=C2N(C(C)C)C=C1SCCN=C1CCCN1C VFOJHMFMHHQHOT-UHFFFAOYSA-N 0.000 claims 1
- WQGKQFVLIZNUSC-UHFFFAOYSA-N 2-(1-cyclopentylindol-3-yl)sulfanylethanamine Chemical compound C12=CC=CC=C2C(SCCN)=CN1C1CCCC1 WQGKQFVLIZNUSC-UHFFFAOYSA-N 0.000 claims 1
- WRHYDNDLPSEYFH-UHFFFAOYSA-N 2-(1-ethylindol-3-yl)sulfanylethanamine Chemical compound C1=CC=C2N(CC)C=C(SCCN)C2=C1 WRHYDNDLPSEYFH-UHFFFAOYSA-N 0.000 claims 1
- MQBVRKQCYYNJIC-UHFFFAOYSA-N 2-(1-methylindol-3-yl)sulfanylethanamine Chemical compound C1=CC=C2N(C)C=C(SCCN)C2=C1 MQBVRKQCYYNJIC-UHFFFAOYSA-N 0.000 claims 1
- OVRSEWBNQKTKAZ-UHFFFAOYSA-N 2-(1-prop-2-enylindol-3-yl)sulfanylethanamine Chemical compound C1=CC=C2C(SCCN)=CN(CC=C)C2=C1 OVRSEWBNQKTKAZ-UHFFFAOYSA-N 0.000 claims 1
- XPSOAAGRIIESBL-UHFFFAOYSA-N 2-(1-propan-2-ylindol-3-yl)sulfanylethanamine Chemical compound C1=CC=C2N(C(C)C)C=C(SCCN)C2=C1 XPSOAAGRIIESBL-UHFFFAOYSA-N 0.000 claims 1
- GMSQJRQUGADEBQ-UHFFFAOYSA-N 2-(1-propylindol-3-yl)sulfanylethanamine Chemical compound C1=CC=C2N(CCC)C=C(SCCN)C2=C1 GMSQJRQUGADEBQ-UHFFFAOYSA-N 0.000 claims 1
- HMFRHODWXBWUNH-UHFFFAOYSA-N 2-[(2-phenyl-1h-indol-3-yl)sulfanyl]ethanamine Chemical compound N1C2=CC=CC=C2C(SCCN)=C1C1=CC=CC=C1 HMFRHODWXBWUNH-UHFFFAOYSA-N 0.000 claims 1
- JNAGIIJCIXUDEZ-UHFFFAOYSA-N 2-[(5-chloro-1h-indol-3-yl)sulfanyl]ethanamine Chemical compound C1=C(Cl)C=C2C(SCCN)=CNC2=C1 JNAGIIJCIXUDEZ-UHFFFAOYSA-N 0.000 claims 1
- VHZQWAZVILBZAJ-UHFFFAOYSA-N 2-[(5-ethyl-1h-indol-3-yl)sulfanyl]ethanamine Chemical compound CCC1=CC=C2NC=C(SCCN)C2=C1 VHZQWAZVILBZAJ-UHFFFAOYSA-N 0.000 claims 1
- DGXORTSKCZBZRZ-UHFFFAOYSA-N 2-[(5-methoxy-1h-indol-3-yl)sulfanyl]ethanamine Chemical compound COC1=CC=C2NC=C(SCCN)C2=C1 DGXORTSKCZBZRZ-UHFFFAOYSA-N 0.000 claims 1
- OKXYDXXQBJMAMY-UHFFFAOYSA-N 2-[1-(2-methylprop-2-enyl)indol-3-yl]sulfanylethanamine Chemical compound NCCSC1=CN(C2=CC=CC=C12)CC(=C)C OKXYDXXQBJMAMY-UHFFFAOYSA-N 0.000 claims 1
- YKTYALCYYJASLP-UHFFFAOYSA-N 2-[1-(furan-2-ylmethyl)indol-3-yl]sulfanylethanamine Chemical compound NCCSC1=CN(C2=CC=CC=C12)CC=1OC=CC1 YKTYALCYYJASLP-UHFFFAOYSA-N 0.000 claims 1
- WEUSGRBRZNLKBY-UHFFFAOYSA-N 4-(1h-indol-3-ylsulfanyl)butan-1-amine Chemical compound C1=CC=C2C(SCCCCN)=CNC2=C1 WEUSGRBRZNLKBY-UHFFFAOYSA-N 0.000 claims 1
- OBZYOUFHSYJBQT-UHFFFAOYSA-N N-[2-(1H-indol-3-ylsulfonyl)ethyl]-1-methylpyrrolidin-2-imine Chemical compound CN1C(CCC1)=NCCS(=O)(=O)C1=CNC2=CC=CC=C12 OBZYOUFHSYJBQT-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- KGOAMGRGYVQMOW-UHFFFAOYSA-N n-[1-(1h-indol-3-ylsulfanyl)propan-2-yl]-1-methylpyrrolidin-2-imine Chemical compound C=1NC2=CC=CC=C2C=1SCC(C)N=C1CCCN1C KGOAMGRGYVQMOW-UHFFFAOYSA-N 0.000 claims 1
- JNLKGYKHNNAGJO-UHFFFAOYSA-N n-[2-(1,2-dimethylindol-3-yl)sulfanylethyl]-1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC1=C(C)N(C)C2=CC=CC=C12 JNLKGYKHNNAGJO-UHFFFAOYSA-N 0.000 claims 1
- GDAKMUMLYHFBRN-UHFFFAOYSA-N n-[2-(1-cyclopentylindol-3-yl)sulfanylethyl]-1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC(C1=CC=CC=C11)=CN1C1CCCC1 GDAKMUMLYHFBRN-UHFFFAOYSA-N 0.000 claims 1
- SAJALXPXCGXYLR-UHFFFAOYSA-N n-[2-(1h-indol-2-ylsulfanyl)ethyl]-1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC1=CC2=CC=CC=C2N1 SAJALXPXCGXYLR-UHFFFAOYSA-N 0.000 claims 1
- ZNDIZIWYZXDCKS-UHFFFAOYSA-N n-[2-(1h-indol-3-ylsulfinyl)ethyl]-1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=NCCS(=O)C1=CNC2=CC=CC=C12 ZNDIZIWYZXDCKS-UHFFFAOYSA-N 0.000 claims 1
- ZWYPKZUTLGJVKN-UHFFFAOYSA-N n-[2-[1-(cyclopropylmethyl)indol-3-yl]sulfanylethyl]-1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC(C1=CC=CC=C11)=CN1CC1CC1 ZWYPKZUTLGJVKN-UHFFFAOYSA-N 0.000 claims 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 230000000747 cardiac effect Effects 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000003457 sulfones Chemical class 0.000 abstract 1
- 150000003462 sulfoxides Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
- 239000000243 solution Substances 0.000 description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000000047 product Substances 0.000 description 34
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- 241000700159 Rattus Species 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229960004132 diethyl ether Drugs 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 229960005419 nitrogen Drugs 0.000 description 12
- 239000012267 brine Substances 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
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- 244000180577 Sambucus australis Species 0.000 description 1
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- 241000212342 Sium Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 210000003815 abdominal wall Anatomy 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- 108091008698 baroreceptors Proteins 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 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 1
- ZKSSGAMPQUXHNK-UHFFFAOYSA-N but-2-enedioic acid;n-[2-[1-(furan-2-ylmethyl)indol-3-yl]sulfanylethyl]-1-methylpyrrolidin-2-imine Chemical compound OC(=O)C=CC(O)=O.CN1CCCC1=NCCSC(C1=CC=CC=C11)=CN1CC1=CC=CO1 ZKSSGAMPQUXHNK-UHFFFAOYSA-N 0.000 description 1
- VCUCOAOTAJUURW-UHFFFAOYSA-N but-2-enedioic acid;n-[4-(1h-indol-3-ylsulfanyl)butyl]-1-methylpyrrolidin-2-imine Chemical compound OC(=O)C=CC(O)=O.CN1CCCC1=NCCCCSC1=CNC2=CC=CC=C12 VCUCOAOTAJUURW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 210000001326 carotid sinus Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229940106265 charcoal Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- YVPJFAHPSNUGOV-UHFFFAOYSA-N cyclohexylsulfamic acid;hydrate Chemical compound O.OS(=O)(=O)NC1CCCCC1 YVPJFAHPSNUGOV-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002550 fecal effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229940077844 iodine / potassium iodide Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 1
- QZCMDHHYFMXWQO-UHFFFAOYSA-N n-[2-[(2-benzyl-1h-indol-3-yl)sulfanyl]ethyl]-1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=NCCSC(C1=CC=CC=C1N1)=C1CC1=CC=CC=C1 QZCMDHHYFMXWQO-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- SUMPVOWEIHBNQO-UHFFFAOYSA-N pentane;propan-2-ol Chemical compound CC(C)O.CCCCC SUMPVOWEIHBNQO-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 210000003516 pericardium Anatomy 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001774 pressoreceptor Anatomy 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 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 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 230000000213 tachycardiac effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229960000340 thiopental sodium Drugs 0.000 description 1
- AWLILQARPMWUHA-UHFFFAOYSA-M thiopental sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC([S-])=NC1=O AWLILQARPMWUHA-UHFFFAOYSA-M 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 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
- C07D209/30—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)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53761274A | 1974-12-30 | 1974-12-30 | |
| US63179875A | 1975-11-13 | 1975-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1065874A true CA1065874A (en) | 1979-11-06 |
Family
ID=27065555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA242,669A Expired CA1065874A (en) | 1974-12-30 | 1975-12-29 | 3-substituted indoles and precursors therefor |
Country Status (27)
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 |
| EP1216988A4 (en) * | 1999-09-28 | 2005-04-20 | Nihon Nohyaku Co Ltd | THIOALKYLAMINE DERIVATIVES AND METHOD FOR THE PREPARATION OF SAID DERIVATIVES |
| 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 IN IN2354/CAL/75A patent/IN142735B/en unknown
- 1975-12-17 NZ NZ179580A patent/NZ179580A/xx unknown
- 1975-12-18 NO NO754313A patent/NO145383C/no unknown
- 1975-12-19 SE SE7514458A patent/SE422210B/xx unknown
- 1975-12-19 DK DK580175A patent/DK580175A/da not_active Application Discontinuation
- 1975-12-24 NL NL7515100A patent/NL7515100A/xx not_active Application Discontinuation
- 1975-12-24 CH CH1679775A patent/CH622516A5/de not_active IP Right Cessation
- 1975-12-26 JP JP50155154A patent/JPS51131872A/ja active Pending
- 1975-12-29 PH PH7517930A patent/PH12328A/en unknown
- 1975-12-29 GB GB53024/75A patent/GB1527510A/en not_active Expired
- 1975-12-29 RO RO7584353A patent/RO69196A/ro unknown
- 1975-12-29 YU YU03322/75A patent/YU332275A/xx unknown
- 1975-12-29 AT AT986075A patent/AT356648B/de not_active IP Right Cessation
- 1975-12-29 IT IT7552899A patent/IT1052654B/it active
- 1975-12-29 CA CA242,669A patent/CA1065874A/en not_active Expired
- 1975-12-29 ES ES443935A patent/ES443935A1/es not_active Expired
- 1975-12-29 DD DD190619A patent/DD125781A5/xx unknown
- 1975-12-29 IL IL48756A patent/IL48756A/xx unknown
- 1975-12-29 FI FI753669A patent/FI64590C/fi not_active IP Right Cessation
- 1975-12-30 FR FR7540132A patent/FR2296413A1/fr active Granted
- 1975-12-30 HU HU75ME1936A patent/HU174948B/hu unknown
- 1975-12-30 DE DE19752559211 patent/DE2559211A1/de not_active Ceased
- 1975-12-30 PL PL1975186097A patent/PL99353B1/pl unknown
- 1975-12-30 AR AR261797A patent/AR219052A1/es active
- 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 HU75ME2020A patent/HU174949B/hu unknown
-
1976
- 1976-08-30 FR FR7626153A patent/FR2315921A1/fr active Granted
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