CH513151A - Verfahren zur Herstellung von S- bzw. O-Heterocyclen mit ankondensierten Phenylresten und deren Verwendung - Google Patents
Verfahren zur Herstellung von S- bzw. O-Heterocyclen mit ankondensierten Phenylresten und deren VerwendungInfo
- Publication number
- CH513151A CH513151A CH165168A CH165168A CH513151A CH 513151 A CH513151 A CH 513151A CH 165168 A CH165168 A CH 165168A CH 165168 A CH165168 A CH 165168A CH 513151 A CH513151 A CH 513151A
- Authority
- CH
- Switzerland
- Prior art keywords
- xanthenone
- groups
- formula
- benzyl
- benzene
- Prior art date
Links
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 title description 4
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 title description 2
- 230000003276 anti-hypertensive effect Effects 0.000 title description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 title description 2
- -1 polymethyleneimino Polymers 0.000 claims abstract description 70
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 7
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 114
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 72
- 238000000034 method Methods 0.000 claims description 67
- 238000002844 melting Methods 0.000 claims description 42
- 230000008018 melting Effects 0.000 claims description 42
- 238000001953 recrystallisation Methods 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 16
- 230000001419 dependent effect Effects 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000010410 layer Substances 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000001302 tertiary amino group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
- GGHJNAUOIAYTQO-UHFFFAOYSA-N 3-[3-(dimethylamino)propoxy]thioxanthen-9-one Chemical compound CN(CCCOC=1C=CC=2C(C3=CC=CC=C3SC2C1)=O)C GGHJNAUOIAYTQO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002902 organometallic compounds Chemical class 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- 238000005956 quaternization reaction Methods 0.000 claims description 3
- 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 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- MOCWZFGEEKNOSW-UHFFFAOYSA-N 9-benzyl-3-[3-(dimethylamino)propoxy]-10,10-dioxothioxanthen-9-ol Chemical compound CN(CCCOC=1C=CC=2C(C3=CC=CC=C3S(C2C1)(=O)=O)(O)CC1=CC=CC=C1)C MOCWZFGEEKNOSW-UHFFFAOYSA-N 0.000 claims description 2
- BBHOXOOJEVRXMD-UHFFFAOYSA-N 9-benzyl-3-[4-(dimethylamino)butoxy]thioxanthen-9-ol Chemical compound CN(CCCCOC=1C=CC=2C(C3=CC=CC=C3SC2C1)(O)CC1=CC=CC=C1)C BBHOXOOJEVRXMD-UHFFFAOYSA-N 0.000 claims description 2
- PGKCUIGJFAIWJK-UHFFFAOYSA-N CN(CC(COC=1C=CC=2C(C3=CC=CC=C3SC2C1)(O)CC1=CC=CC=C1)C)C Chemical compound CN(CC(COC=1C=CC=2C(C3=CC=CC=C3SC2C1)(O)CC1=CC=CC=C1)C)C PGKCUIGJFAIWJK-UHFFFAOYSA-N 0.000 claims description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000012044 organic layer Substances 0.000 claims description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
- 150000002367 halogens Chemical class 0.000 abstract description 4
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 239000003146 anticoagulant agent Substances 0.000 abstract 1
- 229940127219 anticoagulant drug Drugs 0.000 abstract 1
- 229940125681 anticonvulsant agent Drugs 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 239000003218 coronary vasodilator agent Substances 0.000 abstract 1
- 239000002532 enzyme inhibitor Substances 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 42
- 239000000203 mixture Substances 0.000 description 32
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 20
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 14
- XGZXBBPFQWKRNO-UHFFFAOYSA-N 3-[2-(diethylamino)ethoxy]-6-methylxanthen-9-one Chemical compound C(C)N(CCOC=1C=CC=2C(C3=CC=C(C=C3OC2C1)C)=O)CC XGZXBBPFQWKRNO-UHFFFAOYSA-N 0.000 description 13
- RFJHVTPHJIFIOK-UHFFFAOYSA-N 3-hydroxythioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=C(O)C=C3SC2=C1 RFJHVTPHJIFIOK-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ARDFIPMALCNGJV-UHFFFAOYSA-N 3-[2-(diethylamino)ethoxy]thioxanthen-9-one Chemical compound C(C)N(CCOC=1C=CC=2C(C3=CC=CC=C3SC2C1)=O)CC ARDFIPMALCNGJV-UHFFFAOYSA-N 0.000 description 9
- XCJHDJAODLKGLG-UHFFFAOYSA-N 3-hydroxyxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=C(O)C=C3OC2=C1 XCJHDJAODLKGLG-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 8
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 7
- GSUPYROXEHRTBV-UHFFFAOYSA-N 3-[2-(diethylamino)ethoxy]xanthen-9-one Chemical compound C(C)N(CCOC=1C=CC=2C(C3=CC=CC=C3OC2C1)=O)CC GSUPYROXEHRTBV-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- LOHQSBXOVKACBD-UHFFFAOYSA-N 3-[2-(dimethylamino)ethoxy]thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=C(OCCN(C)C)C=C3SC2=C1 LOHQSBXOVKACBD-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical group ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 5
- MDRSIQUHZAUVLE-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(OCCN(C)C)=CC=C3SC2=C1 MDRSIQUHZAUVLE-UHFFFAOYSA-N 0.000 description 4
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 4
- YEWPOEMHUBKIIQ-UHFFFAOYSA-N 3-[2-(4-methylpiperazin-1-yl)ethoxy]thioxanthen-9-one Chemical compound C1CN(C)CCN1CCOC1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YEWPOEMHUBKIIQ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229940073608 benzyl chloride Drugs 0.000 description 4
- GVNSCNGKEXNKBU-UHFFFAOYSA-M magnesium;1-chloro-4-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=C(Cl)C=C1 GVNSCNGKEXNKBU-UHFFFAOYSA-M 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- WNRWEBKEQARBKV-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine Chemical compound ClCCN1CCCCC1 WNRWEBKEQARBKV-UHFFFAOYSA-N 0.000 description 3
- BNLRKUSVMCIOGU-UHFFFAOYSA-N 1-hydroxyxanthen-9-one Chemical compound O1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BNLRKUSVMCIOGU-UHFFFAOYSA-N 0.000 description 3
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 3
- ANHLDZMOXDYFMQ-UHFFFAOYSA-N 2-hydroxythioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(O)=CC=C3SC2=C1 ANHLDZMOXDYFMQ-UHFFFAOYSA-N 0.000 description 3
- XRSUCFIMABMZSG-UHFFFAOYSA-N 3-(2-pyrrolidin-1-ylethoxy)thioxanthen-9-one Chemical compound C=1C=C2C(=O)C3=CC=CC=C3SC2=CC=1OCCN1CCCC1 XRSUCFIMABMZSG-UHFFFAOYSA-N 0.000 description 3
- ZYGWEVRVJRIJDD-UHFFFAOYSA-N 3-[4-(dimethylamino)butoxy]thioxanthen-9-one Chemical compound CN(CCCCOC=1C=CC=2C(C3=CC=CC=C3SC2C1)=O)C ZYGWEVRVJRIJDD-UHFFFAOYSA-N 0.000 description 3
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FHDYRFNCTJFNQX-UHFFFAOYSA-N 1-(2-chloroethyl)-4-methylpiperazine Chemical compound CN1CCN(CCCl)CC1 FHDYRFNCTJFNQX-UHFFFAOYSA-N 0.000 description 2
- RMGFLMXDCGQKPS-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine Chemical compound ClCCN1CCCC1 RMGFLMXDCGQKPS-UHFFFAOYSA-N 0.000 description 2
- DPPSGECSVOYTHT-UHFFFAOYSA-N 2,4-dichloro-6-[2-(diethylamino)ethoxy]xanthen-9-one Chemical compound C(C)N(CCOC=1C=CC=2C(C3=CC(=CC(=C3OC2C1)Cl)Cl)=O)CC DPPSGECSVOYTHT-UHFFFAOYSA-N 0.000 description 2
- BKWDXFZHQNKXNU-UHFFFAOYSA-N 2,4-dichloro-6-hydroxyxanthen-9-one Chemical compound OC=1C=CC=2C(C3=CC(=CC(=C3OC2C1)Cl)Cl)=O BKWDXFZHQNKXNU-UHFFFAOYSA-N 0.000 description 2
- GWYUYOJQQRAJLT-UHFFFAOYSA-N 2-chloro-6-[2-(diethylamino)ethoxy]xanthen-9-one Chemical compound CCN(CC)CCOC1=CC=C2C(=O)C3=CC(Cl)=CC=C3OC2=C1 GWYUYOJQQRAJLT-UHFFFAOYSA-N 0.000 description 2
- CHPBWMASIQIDGT-UHFFFAOYSA-N 2-chloro-6-hydroxyxanthen-9-one Chemical compound OC=1C=CC=2C(C3=CC(=CC=C3OC2C1)Cl)=O CHPBWMASIQIDGT-UHFFFAOYSA-N 0.000 description 2
- RYRHJZDRBCAWMB-UHFFFAOYSA-N 2-ethylsulfanyl-6-hydroxyxanthen-9-one Chemical compound C(C)SC1=CC=C2OC=3C=C(C=CC3C(C2=C1)=O)O RYRHJZDRBCAWMB-UHFFFAOYSA-N 0.000 description 2
- RYCDVTIHVQEAIA-UHFFFAOYSA-N 3-(4-chlorobutoxy)thioxanthen-9-one Chemical compound ClCCCCOC=1C=CC=2C(C3=CC=CC=C3SC2C1)=O RYCDVTIHVQEAIA-UHFFFAOYSA-N 0.000 description 2
- AIQAECOMVINKJC-UHFFFAOYSA-N 3-[2-(dicyclohexylamino)ethoxy]xanthen-9-one Chemical compound O=C1C2=CC=CC=C2OC2=CC(OCCN(C3CCCCC3)C3CCCCC3)=CC=C12 AIQAECOMVINKJC-UHFFFAOYSA-N 0.000 description 2
- VNORFCMSFOSRAE-UHFFFAOYSA-N 3-[2-(diethylamino)ethoxy]-5-iodoxanthen-9-one Chemical compound CCN(CC)CCOC1=CC=C2C(=O)C3=CC=CC(I)=C3OC2=C1 VNORFCMSFOSRAE-UHFFFAOYSA-N 0.000 description 2
- GCAWONWXLOTEOM-UHFFFAOYSA-N 3-[2-(diethylamino)ethoxy]-6-hexoxyxanthen-9-one Chemical compound C(C)N(CCOC=1C=CC=2C(C3=CC=C(C=C3OC2C1)OCCCCCC)=O)CC GCAWONWXLOTEOM-UHFFFAOYSA-N 0.000 description 2
- AVVSQPCUTMEADJ-UHFFFAOYSA-N 3-[2-(dimethylamino)propoxy]xanthen-9-one Chemical compound CN(C(COC=1C=CC=2C(C3=CC=CC=C3OC2C1)=O)C)C AVVSQPCUTMEADJ-UHFFFAOYSA-N 0.000 description 2
- KPJSYKOOPHZMNB-UHFFFAOYSA-N 3-[3-(diethylamino)propoxy]thioxanthen-9-one Chemical compound C(C)N(CCCOC=1C=CC=2C(C3=CC=CC=C3SC2C1)=O)CC KPJSYKOOPHZMNB-UHFFFAOYSA-N 0.000 description 2
- OBMOGACIMUVSQP-UHFFFAOYSA-N 3-[3-(dimethylamino)propoxy]-10,10-dioxothioxanthen-9-one Chemical compound CN(CCCOC=1C=CC=2C(C3=CC=CC=C3S(C2C1)(=O)=O)=O)C OBMOGACIMUVSQP-UHFFFAOYSA-N 0.000 description 2
- DMBPIWMNQSJGNE-UHFFFAOYSA-N 3-[3-(dimethylamino)propoxy]xanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=C(OCCCN(C)C)C=C3OC2=C1 DMBPIWMNQSJGNE-UHFFFAOYSA-N 0.000 description 2
- WJNPOHGUEPIOAJ-UHFFFAOYSA-N 3-ethoxy-6-hydroxyxanthen-9-one Chemical compound OC=1C=CC=2C(C3=CC=C(C=C3OC2C1)OCC)=O WJNPOHGUEPIOAJ-UHFFFAOYSA-N 0.000 description 2
- QAGCSAUIYUWHPO-UHFFFAOYSA-N 3-hexoxy-6-hydroxyxanthen-9-one Chemical compound OC=1C=CC=2C(C3=CC=C(C=C3OC2C1)OCCCCCC)=O QAGCSAUIYUWHPO-UHFFFAOYSA-N 0.000 description 2
- ILJBVMUFCSSEKM-UHFFFAOYSA-N 3-hydroxy-5-iodoxanthen-9-one Chemical compound OC=1C=CC=2C(C3=CC=CC(=C3OC2C1)I)=O ILJBVMUFCSSEKM-UHFFFAOYSA-N 0.000 description 2
- ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 2
- JKBJVOLQKOVXKJ-UHFFFAOYSA-N 4-bromo-6-hydroxy-1,3-dimethoxyxanthen-9-one Chemical compound OC=1C=CC=2C(C3=C(C=C(C(=C3OC2C1)Br)OC)OC)=O JKBJVOLQKOVXKJ-UHFFFAOYSA-N 0.000 description 2
- PFLOBTHSRMEGBI-UHFFFAOYSA-N 4-bromo-6-hydroxy-2,3-dimethylxanthen-9-one Chemical compound OC=1C=CC=2C(C3=CC(=C(C(=C3OC2C1)Br)C)C)=O PFLOBTHSRMEGBI-UHFFFAOYSA-N 0.000 description 2
- UVLVRNPBVBLQKL-UHFFFAOYSA-N 5-butyl-3-hydroxyxanthen-9-one Chemical compound OC=1C=CC=2C(C3=CC=CC(=C3OC2C1)CCCC)=O UVLVRNPBVBLQKL-UHFFFAOYSA-N 0.000 description 2
- AVRZHIWTCVPBSM-UHFFFAOYSA-N 5-fluoro-3-hydroxyxanthen-9-one Chemical compound OC=1C=CC=2C(C3=CC=CC(=C3OC2C1)F)=O AVRZHIWTCVPBSM-UHFFFAOYSA-N 0.000 description 2
- JLYKXLNXOATTLC-UHFFFAOYSA-N 6-[2-(diethylamino)ethoxy]-2-ethylsulfanylxanthen-9-one Chemical compound C(C)N(CCOC=1C=CC=2C(C3=CC(=CC=C3OC2C1)SCC)=O)CC JLYKXLNXOATTLC-UHFFFAOYSA-N 0.000 description 2
- ZMGNUPJXCWCLIY-UHFFFAOYSA-N 6-hydroxy-2-propan-2-ylxanthen-9-one Chemical compound OC=1C=CC=2C(C3=CC(=CC=C3OC2C1)C(C)C)=O ZMGNUPJXCWCLIY-UHFFFAOYSA-N 0.000 description 2
- LYXDRLVRYQTOLB-UHFFFAOYSA-N 6-hydroxy-3,4-dimethoxyxanthen-9-one Chemical compound OC=1C=CC=2C(C3=CC=C(C(=C3OC2C1)OC)OC)=O LYXDRLVRYQTOLB-UHFFFAOYSA-N 0.000 description 2
- GOMPWLZAVGHEDF-UHFFFAOYSA-N 9h-thioxanthene;9h-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1.C1=CC=C2CC3=CC=CC=C3SC2=C1 GOMPWLZAVGHEDF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KKUUXTKWHCQOAM-UHFFFAOYSA-N C(C)N(CCOC=1C=CC=2C(C3=CC=C(C(=C3OC2C1)OC)OC)=O)CC Chemical compound C(C)N(CCOC=1C=CC=2C(C3=CC=C(C(=C3OC2C1)OC)OC)=O)CC KKUUXTKWHCQOAM-UHFFFAOYSA-N 0.000 description 2
- MPMQYIBAAYREFK-UHFFFAOYSA-N C(C1=CC=CC=C1)N(CCOC=1C=CC=2C(C3=CC=CC=C3OC2C1)=O)CC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)N(CCOC=1C=CC=2C(C3=CC=CC=C3OC2C1)=O)CC1=CC=CC=C1 MPMQYIBAAYREFK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- ADGLVKPKVYPNFV-UHFFFAOYSA-N CCN(CC)CCOC1=CC=C2C(OC3=C(Br)C(C)=C(C)C=C3C2(O)CC2=CC=CC=C2)=C1 Chemical compound CCN(CC)CCOC1=CC=C2C(OC3=C(Br)C(C)=C(C)C=C3C2(O)CC2=CC=CC=C2)=C1 ADGLVKPKVYPNFV-UHFFFAOYSA-N 0.000 description 1
- OJRTUKWUWAKVQS-UHFFFAOYSA-N CCN(CC)CCOC1=CC=C2C(OC3=CC=C(Cl)C=C3C2(O)CC2=CC=CC=C2)=C1 Chemical compound CCN(CC)CCOC1=CC=C2C(OC3=CC=C(Cl)C=C3C2(O)CC2=CC=CC=C2)=C1 OJRTUKWUWAKVQS-UHFFFAOYSA-N 0.000 description 1
- ZVNOIUMCZADWRN-UHFFFAOYSA-N CCOC1=CC=C2C(OC3=CC(OCCN(CC)CC)=CC=C3C2(O)CC2=CC=CC=C2)=C1 Chemical compound CCOC1=CC=C2C(OC3=CC(OCCN(CC)CC)=CC=C3C2(O)CC2=CC=CC=C2)=C1 ZVNOIUMCZADWRN-UHFFFAOYSA-N 0.000 description 1
- BGNJVTXOTODYBV-UHFFFAOYSA-N CN(CC(COC=1C=CC=2C(C3=CC=CC=C3SC2C1)=O)C)C Chemical compound CN(CC(COC=1C=CC=2C(C3=CC=CC=C3SC2C1)=O)C)C BGNJVTXOTODYBV-UHFFFAOYSA-N 0.000 description 1
- NSICEWYVKWHFRP-UHFFFAOYSA-N CN(CCCOC=1C=CC=2C(C3=CC=CC=C3OC2C1)(O)CC1=CC=CC=C1)C Chemical compound CN(CCCOC=1C=CC=2C(C3=CC=CC=C3OC2C1)(O)CC1=CC=CC=C1)C NSICEWYVKWHFRP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- HQFJLIRZOLCAPG-UHFFFAOYSA-N N1(CCOCC1)CCOC=1C=CC=2C(C3=CC=CC=C3SC2C1)(O)CC1=CC=CC=C1 Chemical compound N1(CCOCC1)CCOC=1C=CC=2C(C3=CC=CC=C3SC2C1)(O)CC1=CC=CC=C1 HQFJLIRZOLCAPG-UHFFFAOYSA-N 0.000 description 1
- SAEZMAXQOGFHKT-UHFFFAOYSA-N OC1(CC2=CC=C(Cl)C=C2)C2=CC=CC=C2SC2=CC(OCCN3CCCCC3)=CC=C12 Chemical compound OC1(CC2=CC=C(Cl)C=C2)C2=CC=CC=C2SC2=CC(OCCN3CCCCC3)=CC=C12 SAEZMAXQOGFHKT-UHFFFAOYSA-N 0.000 description 1
- IIWLFVIGTHQYHC-UHFFFAOYSA-N OC1(CC2=CC=CC=C2)C(C=CC(OCCN2CCCCCC2)=C2)=C2OC2=CC=CC=C12 Chemical compound OC1(CC2=CC=CC=C2)C(C=CC(OCCN2CCCCCC2)=C2)=C2OC2=CC=CC=C12 IIWLFVIGTHQYHC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- JDHHFCKOCSYEJV-UHFFFAOYSA-M [Br-].CC1=CC=C(C[Mg+])C=C1 Chemical compound [Br-].CC1=CC=C(C[Mg+])C=C1 JDHHFCKOCSYEJV-UHFFFAOYSA-M 0.000 description 1
- ZHADUEJLBZZTHE-UHFFFAOYSA-M [Cl-].BrC1=CC=C(C[Mg+])C=C1 Chemical compound [Cl-].BrC1=CC=C(C[Mg+])C=C1 ZHADUEJLBZZTHE-UHFFFAOYSA-M 0.000 description 1
- PQDGQUPDDGUKLP-UHFFFAOYSA-M [Cl-].FC1=CC=C(C[Mg+])C=C1 Chemical compound [Cl-].FC1=CC=C(C[Mg+])C=C1 PQDGQUPDDGUKLP-UHFFFAOYSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000000026 anti-ulcerogenic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical class [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- PHSLYQFWLCWIBU-UHFFFAOYSA-M magnesium;1-chloro-2-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1Cl PHSLYQFWLCWIBU-UHFFFAOYSA-M 0.000 description 1
- BQNQIHYLDYHYQP-UHFFFAOYSA-M magnesium;1-chloro-3-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC(Cl)=C1 BQNQIHYLDYHYQP-UHFFFAOYSA-M 0.000 description 1
- JHMNJUQVLPODJN-UHFFFAOYSA-M magnesium;1-fluoro-4-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=C(F)C=C1 JHMNJUQVLPODJN-UHFFFAOYSA-M 0.000 description 1
- NMQPDYTXGLHYDX-UHFFFAOYSA-M magnesium;1-methanidyl-4-methylbenzene;chloride Chemical compound [Mg+2].[Cl-].CC1=CC=C([CH2-])C=C1 NMQPDYTXGLHYDX-UHFFFAOYSA-M 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- PEDYEFUCMXSQJM-UHFFFAOYSA-N n-benzyl-2-chloro-n-ethylethanamine Chemical compound ClCCN(CC)CC1=CC=CC=C1 PEDYEFUCMXSQJM-UHFFFAOYSA-N 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes 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 in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH848170A CH515900A (de) | 1967-02-10 | 1968-02-05 | Verfahren zur Herstellung von S- bzw. O-Heterocyclien mit ankondensierten Phenylresten und deren Verwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61505867A | 1967-02-10 | 1967-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH513151A true CH513151A (de) | 1971-09-30 |
Family
ID=24463820
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH165168A CH513151A (de) | 1967-02-10 | 1968-02-05 | Verfahren zur Herstellung von S- bzw. O-Heterocyclen mit ankondensierten Phenylresten und deren Verwendung |
| CH182871A CH546757A (de) | 1967-02-10 | 1968-02-05 | Verfahren zur herstellung von s- bzw. o-heterocyclen mit ankondensierten benzolkernen und deren verwendung. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH182871A CH546757A (de) | 1967-02-10 | 1968-02-05 | Verfahren zur herstellung von s- bzw. o-heterocyclen mit ankondensierten benzolkernen und deren verwendung. |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE710423A (en, 2012) |
| CH (2) | CH513151A (en, 2012) |
| DE (1) | DE1668974A1 (en, 2012) |
| FR (1) | FR8379M (en, 2012) |
| GB (1) | GB1195752A (en, 2012) |
| NL (2) | NL6801093A (en, 2012) |
| SE (1) | SE352355B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106810532B (zh) * | 2016-12-20 | 2019-03-15 | 四川大学 | 一类胺烷氧基噻吨酮类化合物、其制备方法和用途 |
-
1968
- 1968-01-09 GB GB133868A patent/GB1195752A/en not_active Expired
- 1968-01-24 FR FR137212A patent/FR8379M/fr not_active Expired
- 1968-01-24 NL NL6801093A patent/NL6801093A/xx unknown
- 1968-02-05 CH CH165168A patent/CH513151A/de not_active IP Right Cessation
- 1968-02-05 DE DE19681668974 patent/DE1668974A1/de active Pending
- 1968-02-05 SE SE147468A patent/SE352355B/xx unknown
- 1968-02-05 CH CH182871A patent/CH546757A/xx not_active IP Right Cessation
- 1968-02-07 BE BE710423D patent/BE710423A/xx unknown
-
1972
- 1972-03-10 NL NL7203258A patent/NL7203258A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6801093A (en, 2012) | 1968-08-12 |
| BE710423A (en, 2012) | 1968-08-07 |
| GB1195752A (en) | 1970-06-24 |
| SE352355B (en, 2012) | 1972-12-27 |
| FR8379M (en, 2012) | 1971-03-01 |
| CH546757A (de) | 1974-03-15 |
| NL7203258A (en, 2012) | 1972-06-26 |
| DE1668974A1 (de) | 1971-09-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |