HU176315B - Process for producing substituted aminocarbonyloxy-isoindolinone-, -pyrrolo-pyridine-, pyrrolo-pyrasine and oxathiino-pyrrole derivatives - Google Patents
Process for producing substituted aminocarbonyloxy-isoindolinone-, -pyrrolo-pyridine-, pyrrolo-pyrasine and oxathiino-pyrrole derivatives Download PDFInfo
- Publication number
- HU176315B HU176315B HU76RO886A HURO000886A HU176315B HU 176315 B HU176315 B HU 176315B HU 76RO886 A HU76RO886 A HU 76RO886A HU RO000886 A HURO000886 A HU RO000886A HU 176315 B HU176315 B HU 176315B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- alkyl
- chloro
- oxo
- isoindolinone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 36
- PNAANLYLOFUMKL-UHFFFAOYSA-N (3-oxo-1H-isoindol-2-yl) carbamate Chemical class NC(=O)ON1C(C2=CC=CC=C2C1)=O PNAANLYLOFUMKL-UHFFFAOYSA-N 0.000 title claims description 3
- PFOLPSNENWUAAA-UHFFFAOYSA-N 5H-oxathiino[4,3-b]pyrrole Chemical class S1OC=CC2=C1C=CN2 PFOLPSNENWUAAA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 24
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical group C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 8
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 5
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- CGULSYWKVCXEHE-UHFFFAOYSA-N 5,6-dihydropyrrolo[3,4-b]pyridin-7-one Chemical group C1=CN=C2C(=O)NCC2=C1 CGULSYWKVCXEHE-UHFFFAOYSA-N 0.000 claims description 4
- KQMCKDYNYRLDPL-UHFFFAOYSA-N 6,7-dihydropyrrolo[3,4-b]pyrazin-5-one Chemical group C1=CN=C2C(=O)NCC2=N1 KQMCKDYNYRLDPL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical class C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims description 3
- HFTVJMFWJUFBNO-UHFFFAOYSA-N 5h-pyrrolo[2,3-b]pyrazine Chemical class C1=CN=C2NC=CC2=N1 HFTVJMFWJUFBNO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- HOHLESHUQGXSLJ-UHFFFAOYSA-N 2-(trifluoromethyl)-3h-isoindol-1-one Chemical group C1=CC=C2C(=O)N(C(F)(F)F)CC2=C1 HOHLESHUQGXSLJ-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001923 cyclic compounds Chemical class 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 177
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- 239000011541 reaction mixture Substances 0.000 description 42
- 238000001914 filtration Methods 0.000 description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
- -1 piperazinylcarbonyloxy Chemical group 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 31
- 239000000243 solution Substances 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- 239000002244 precipitate Substances 0.000 description 28
- 239000000725 suspension Substances 0.000 description 28
- 239000000203 mixture Substances 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 20
- 239000000706 filtrate Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZESSRQSTYNMBBB-UHFFFAOYSA-N [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] phenyl carbonate Chemical compound N=1C2=NC(Cl)=CC=C2C=CC=1N(C(C1=CC=CC=C11)=O)C1OC(=O)OC1=CC=CC=C1 ZESSRQSTYNMBBB-UHFFFAOYSA-N 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- UWERZJBLURGYFF-UHFFFAOYSA-N 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-3h-isoindol-1-one Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC=CC=C4C3=O)O)=CC=C21 UWERZJBLURGYFF-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
- 238000001035 drying Methods 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- NSPQTGOJGZXAJM-UHFFFAOYSA-N 7-amino-1h-1,8-naphthyridin-2-one Chemical compound C1=CC(=O)NC2=NC(N)=CC=C21 NSPQTGOJGZXAJM-UHFFFAOYSA-N 0.000 description 7
- MLZSNSFBRPLAPB-UHFFFAOYSA-N 6-(7-chloro-1,8-naphthyridin-2-yl)-7-hydroxy-7h-pyrrolo[3,4-b]pyrazin-5-one Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=NC=CN=C4C3=O)O)=CC=C21 MLZSNSFBRPLAPB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical group C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 4
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- CRADWWWVIYEAFR-UHFFFAOYSA-N 1,8-naphthyridin-2-amine Chemical compound C1=CC=NC2=NC(N)=CC=C21 CRADWWWVIYEAFR-UHFFFAOYSA-N 0.000 description 3
- LUJWIDFODBQELS-UHFFFAOYSA-N 2-(7-chloro-1,8-naphthyridin-2-yl)-5-(trifluoromethyl)isoindole-1,3-dione Chemical compound C1=CC(Cl)=NC2=NC(N3C(=O)C4=CC=C(C=C4C3=O)C(F)(F)F)=CC=C21 LUJWIDFODBQELS-UHFFFAOYSA-N 0.000 description 3
- VFDUATBWQMJDFP-UHFFFAOYSA-N 2-amino-3-methyl-4-(trifluoromethyl)benzoic acid Chemical compound CC1=C(N)C(C(O)=O)=CC=C1C(F)(F)F VFDUATBWQMJDFP-UHFFFAOYSA-N 0.000 description 3
- XKHHGHINTBPDST-UHFFFAOYSA-N 2-cyano-3-methyl-4-(trifluoromethyl)benzoic acid Chemical compound Cc1c(C#N)c(ccc1C(F)(F)F)C(O)=O XKHHGHINTBPDST-UHFFFAOYSA-N 0.000 description 3
- VNLYHYHJIXGBFX-UHFFFAOYSA-N 4-(trifluoromethyl)phthalic acid Chemical compound OC(=O)C1=CC=C(C(F)(F)F)C=C1C(O)=O VNLYHYHJIXGBFX-UHFFFAOYSA-N 0.000 description 3
- AKAAHMXNWDUFTD-UHFFFAOYSA-N 5-(trifluoromethyl)-2-benzofuran-1,3-dione Chemical compound FC(F)(F)C1=CC=C2C(=O)OC(=O)C2=C1 AKAAHMXNWDUFTD-UHFFFAOYSA-N 0.000 description 3
- LDCOFKXSMUTNAB-UHFFFAOYSA-N 5-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-3h-isoindol-1-one Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC(Cl)=CC=C4C3=O)O)=CC=C21 LDCOFKXSMUTNAB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LMIXRIDQXIGFPG-UHFFFAOYSA-N [6-(7-chloro-1,8-naphthyridin-2-yl)-5-oxo-7h-pyrrolo[3,4-b]pyrazin-7-yl] phenyl carbonate Chemical compound N=1C2=NC(Cl)=CC=C2C=CC=1N(C(C1=NC=CN=C11)=O)C1OC(=O)OC1=CC=CC=C1 LMIXRIDQXIGFPG-UHFFFAOYSA-N 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- CHGVIQWWXDOWRN-UHFFFAOYSA-N n-butyl-n-methylcarbamoyl chloride Chemical compound CCCCN(C)C(Cl)=O CHGVIQWWXDOWRN-UHFFFAOYSA-N 0.000 description 3
- XZVYDRLPXWFRIS-UHFFFAOYSA-N n-ethyl-n-methylcarbamoyl chloride Chemical compound CCN(C)C(Cl)=O XZVYDRLPXWFRIS-UHFFFAOYSA-N 0.000 description 3
- YEMRRHHMLASGRQ-UHFFFAOYSA-N n-methyl-n-propylcarbamoyl chloride Chemical compound CCCN(C)C(Cl)=O YEMRRHHMLASGRQ-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VBDNYRVQYGYKIT-UHFFFAOYSA-N 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-5-(trifluoromethyl)-3h-isoindol-1-one Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC(=CC=C4C3=O)C(F)(F)F)O)=CC=C21 VBDNYRVQYGYKIT-UHFFFAOYSA-N 0.000 description 2
- OJFGKHPNYXIDRK-UHFFFAOYSA-N 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-6-(trifluoromethyl)-3h-isoindol-1-one Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC=C(C=C4C3=O)C(F)(F)F)O)=CC=C21 OJFGKHPNYXIDRK-UHFFFAOYSA-N 0.000 description 2
- NQTLZJODEOHALT-UHFFFAOYSA-N 2-amino-4-(trifluoromethyl)benzoic acid Chemical compound NC1=CC(C(F)(F)F)=CC=C1C(O)=O NQTLZJODEOHALT-UHFFFAOYSA-N 0.000 description 2
- HTIZLJISEUYGSA-UHFFFAOYSA-N 2-chloro-1,8-naphthyridine Chemical compound C1=CC=NC2=NC(Cl)=CC=C21 HTIZLJISEUYGSA-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- BTTRMCQEPDPCPA-UHFFFAOYSA-N 4-chlorophthalic anhydride Chemical compound ClC1=CC=C2C(=O)OC(=O)C2=C1 BTTRMCQEPDPCPA-UHFFFAOYSA-N 0.000 description 2
- SWCFXQOKDPKZQD-UHFFFAOYSA-N 5-chloro-7a-(7-chloro-1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC(Cl)=NC2=NC(C34C(=O)NC(=O)C3C=C(C=C4)Cl)=CC=C21 SWCFXQOKDPKZQD-UHFFFAOYSA-N 0.000 description 2
- NIITWRNWQGFEPV-UHFFFAOYSA-N 5-chloro-7a-(7-oxo-8h-1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC(=O)NC2=NC(C34C(=O)NC(=O)C3C=C(C=C4)Cl)=CC=C21 NIITWRNWQGFEPV-UHFFFAOYSA-N 0.000 description 2
- SJMNQXLXIIXDDS-UHFFFAOYSA-N 6,7-dihydro-5h-pyrrolo[3,4-b]pyridine Chemical group C1=CC=C2CNCC2=N1 SJMNQXLXIIXDDS-UHFFFAOYSA-N 0.000 description 2
- RDYDMTCWKUJZNZ-UHFFFAOYSA-N 6-(7-chloro-1,8-naphthyridin-2-yl)-5-hydroxy-5h-pyrrolo[3,4-b]pyridin-7-one Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC=CN=C4C3=O)O)=CC=C21 RDYDMTCWKUJZNZ-UHFFFAOYSA-N 0.000 description 2
- YAWCXNBQBCOBBF-UHFFFAOYSA-N 6-(7-chloro-1,8-naphthyridin-2-yl)pyrrolo[3,4-b]pyrazine-5,7-dione Chemical compound O=C1C2=NC=CN=C2C(=O)N1C1=NC2=NC(Cl)=CC=C2C=C1 YAWCXNBQBCOBBF-UHFFFAOYSA-N 0.000 description 2
- SNHTYMYYIHSPLP-UHFFFAOYSA-N 6-(7-oxo-8h-1,8-naphthyridin-2-yl)pyrrolo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CC(=O)NC2=NC(N3C(C4=NC=CN=C4C3=O)=O)=CC=C21 SNHTYMYYIHSPLP-UHFFFAOYSA-N 0.000 description 2
- HRXBYPUUCBEZAS-UHFFFAOYSA-N 7-chloro-1,8-naphthyridin-2-amine Chemical compound C1=CC(Cl)=NC2=NC(N)=CC=C21 HRXBYPUUCBEZAS-UHFFFAOYSA-N 0.000 description 2
- RJLATJCUBXLWQV-UHFFFAOYSA-N 7a-(7-chloro-1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC=CC2C(=O)NC(=O)C21C1=NC2=NC(Cl)=CC=C2C=C1 RJLATJCUBXLWQV-UHFFFAOYSA-N 0.000 description 2
- RMPKHFJYALJCOR-UHFFFAOYSA-N 7a-(7-oxo-8h-1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC(=O)NC2=NC(C34C(=O)NC(C3C=CC=C4)=O)=CC=C21 RMPKHFJYALJCOR-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 231100000111 LD50 Toxicity 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
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- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
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- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
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- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
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- 238000004821 distillation Methods 0.000 description 1
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- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
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- MCQOWYALZVKMAR-UHFFFAOYSA-N furo[3,4-b]pyridine-5,7-dione Chemical compound C1=CC=C2C(=O)OC(=O)C2=N1 MCQOWYALZVKMAR-UHFFFAOYSA-N 0.000 description 1
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- FMNXOVQDRMSXLX-UHFFFAOYSA-N methyl 2-[[2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl]oxycarbonylamino]acetate Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC=CC=C4C3=O)OC(=O)NCC(=O)OC)=CC=C21 FMNXOVQDRMSXLX-UHFFFAOYSA-N 0.000 description 1
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- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
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- 238000000053 physical method Methods 0.000 description 1
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- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- ZRKGTINFVOLLNT-UHFFFAOYSA-N pyrrolo[3,4-b]pyridine-5,7-dione Chemical compound C1=CC=C2C(=O)NC(=O)C2=N1 ZRKGTINFVOLLNT-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YOEWQQVKRJEPAE-UHFFFAOYSA-L succinylcholine chloride (anhydrous) Chemical compound [Cl-].[Cl-].C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C YOEWQQVKRJEPAE-UHFFFAOYSA-L 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7510756A FR2321290A1 (fr) | 1975-04-07 | 1975-04-07 | Nouveaux derives de l'isoindoline, leur preparation et les compositions qui les contiennent |
| FR7603773A FR2340733A2 (fr) | 1976-02-11 | 1976-02-11 | Nouveaux derives de l'isoindoline, leur preparation et les compositions qui les contiennent |
| FR7603774A FR2340731A1 (fr) | 1976-02-11 | 1976-02-11 | Nouveaux composes heterocycliques, leur preparation et les compositions qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU176315B true HU176315B (en) | 1981-01-28 |
Family
ID=27250439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU76RO886A HU176315B (en) | 1975-04-07 | 1976-04-07 | Process for producing substituted aminocarbonyloxy-isoindolinone-, -pyrrolo-pyridine-, pyrrolo-pyrasine and oxathiino-pyrrole derivatives |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4086348A (en, 2012) |
| JP (1) | JPS51122094A (en, 2012) |
| AR (3) | AR214286A1 (en, 2012) |
| AT (1) | AT348524B (en, 2012) |
| CA (1) | CA1072957A (en, 2012) |
| CH (2) | CH613453A5 (en, 2012) |
| CS (3) | CS186748B2 (en, 2012) |
| CY (1) | CY1085A (en, 2012) |
| DD (1) | DD123605A5 (en, 2012) |
| DE (1) | DE2615067A1 (en, 2012) |
| DK (1) | DK162976A (en, 2012) |
| ES (2) | ES446762A1 (en, 2012) |
| FI (1) | FI60012C (en, 2012) |
| GB (1) | GB1483996A (en, 2012) |
| HK (1) | HK54580A (en, 2012) |
| HU (1) | HU176315B (en, 2012) |
| IE (1) | IE42973B1 (en, 2012) |
| IL (1) | IL49344A (en, 2012) |
| LU (1) | LU74703A1 (en, 2012) |
| MX (1) | MX3138E (en, 2012) |
| NL (1) | NL7603307A (en, 2012) |
| NO (1) | NO144019C (en, 2012) |
| OA (1) | OA05287A (en, 2012) |
| PH (1) | PH14015A (en, 2012) |
| PL (3) | PL100987B1 (en, 2012) |
| PT (1) | PT64976B (en, 2012) |
| SE (2) | SE7604044L (en, 2012) |
| SU (3) | SU648102A3 (en, 2012) |
| YU (3) | YU86976A (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1265803A (fr) * | 1985-07-11 | 1990-02-13 | Claude Cotrel | Amides substitues, leur preparation et les medicaments qui les contiennent |
| DE10042093A1 (de) * | 2000-08-26 | 2002-03-07 | Dresden Arzneimittel | Antikonvulsiv wirkende 6,7-Dihydro-pyrrolo[3,4-d]pyridin-5-one und Verfahren zu deren Darstellung |
| UY28094A1 (es) * | 2002-11-26 | 2004-06-30 | Maruishi Pharma | Derivados de la isoindolina |
| WO2007080430A1 (en) * | 2006-01-16 | 2007-07-19 | Generics [Uk] Limited | Novel process |
| WO2014114779A1 (en) * | 2013-01-28 | 2014-07-31 | H. Lundbeck A/S | N-substituted-5-substituted phthalamic acids as sortilin inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA04700A (fr) * | 1973-05-15 | 1980-07-31 | Rhone Poulenc Sa | Nouveaux dérivés de la naphtyridine et leur procédé de préparation. |
-
1976
- 1976-03-26 OA OA55782A patent/OA05287A/xx unknown
- 1976-03-30 NL NL7603307A patent/NL7603307A/xx not_active Application Discontinuation
- 1976-03-31 CS CS7700002624A patent/CS186748B2/cs unknown
- 1976-03-31 CS CS7700002623A patent/CS186747B2/cs unknown
- 1976-03-31 CS CS7600002084A patent/CS186734B2/cs unknown
- 1976-04-05 US US05/673,868 patent/US4086348A/en not_active Expired - Lifetime
- 1976-04-05 CA CA249,577A patent/CA1072957A/fr not_active Expired
- 1976-04-05 GB GB13703/76A patent/GB1483996A/en not_active Expired
- 1976-04-05 CY CY1085A patent/CY1085A/xx unknown
- 1976-04-05 IE IE704/76A patent/IE42973B1/en unknown
- 1976-04-05 IL IL49344A patent/IL49344A/xx unknown
- 1976-04-05 PH PH18289A patent/PH14015A/en unknown
- 1976-04-05 JP JP51038103A patent/JPS51122094A/ja active Granted
- 1976-04-05 DD DD192209A patent/DD123605A5/xx unknown
- 1976-04-06 YU YU00869/76A patent/YU86976A/xx unknown
- 1976-04-06 SE SE7604044D patent/SE7604044L/xx not_active Application Discontinuation
- 1976-04-06 SU SU762339152A patent/SU648102A3/ru active
- 1976-04-06 PT PT64976A patent/PT64976B/pt unknown
- 1976-04-06 NO NO761168A patent/NO144019C/no unknown
- 1976-04-06 CH CH430576A patent/CH613453A5/xx not_active IP Right Cessation
- 1976-04-06 CH CH1212178A patent/CH614209A5/fr not_active IP Right Cessation
- 1976-04-06 DK DK162976A patent/DK162976A/da not_active IP Right Cessation
- 1976-04-06 MX MX14476U patent/MX3138E/es unknown
- 1976-04-06 LU LU74703A patent/LU74703A1/xx unknown
- 1976-04-06 SE SE7604044A patent/SE421793B/xx not_active IP Right Cessation
- 1976-04-07 AR AR262814A patent/AR214286A1/es active
- 1976-04-07 PL PL1976202791A patent/PL100987B1/pl unknown
- 1976-04-07 PL PL1976202792A patent/PL100988B1/pl unknown
- 1976-04-07 HU HU76RO886A patent/HU176315B/hu unknown
- 1976-04-07 ES ES446762A patent/ES446762A1/es not_active Expired
- 1976-04-07 PL PL1976188560A patent/PL100184B1/pl unknown
- 1976-04-07 FI FI760937A patent/FI60012C/fi not_active IP Right Cessation
- 1976-04-07 DE DE19762615067 patent/DE2615067A1/de not_active Ceased
- 1976-04-07 AT AT249776A patent/AT348524B/de not_active IP Right Cessation
- 1976-06-14 ES ES448847A patent/ES448847A1/es not_active Expired
- 1976-09-28 AR AR264893A patent/AR213739A1/es active
- 1976-09-30 AR AR264924A patent/AR214055A1/es active
-
1977
- 1977-04-21 SU SU772473623A patent/SU638258A3/ru active
- 1977-04-21 SU SU772473622A patent/SU637082A3/ru active
-
1980
- 1980-09-25 HK HK545/80A patent/HK54580A/xx unknown
-
1982
- 1982-06-15 YU YU01305/82A patent/YU130582A/xx unknown
- 1982-06-15 YU YU01304/82A patent/YU130482A/xx unknown
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