NO134910B - - Google Patents
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- NO134910B NO134910B NO743997A NO743997A NO134910B NO 134910 B NO134910 B NO 134910B NO 743997 A NO743997 A NO 743997A NO 743997 A NO743997 A NO 743997A NO 134910 B NO134910 B NO 134910B
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- NO
- Norway
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- parts
- acid
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- 150000001875 compounds Chemical class 0.000 claims description 72
- 238000000034 method Methods 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 71
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 56
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000013078 crystal Substances 0.000 description 45
- 239000000203 mixture Substances 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- 238000000921 elemental analysis Methods 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 229960000583 acetic acid Drugs 0.000 description 25
- 238000001953 recrystallisation Methods 0.000 description 25
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 23
- 235000011054 acetic acid Nutrition 0.000 description 22
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- -1 etc.) Chemical compound 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 11
- 229910000029 sodium carbonate Inorganic materials 0.000 description 11
- 235000017550 sodium carbonate Nutrition 0.000 description 11
- 150000008366 benzophenones Chemical class 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- 150000002905 orthoesters Chemical class 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- ZAXFFQSOWYVGER-UHFFFAOYSA-N 3-amino-6-chloro-4-phenylquinazolin-4-ol Chemical compound NN1C=NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1 ZAXFFQSOWYVGER-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- UZXMWIGOTGGWPU-UHFFFAOYSA-N 3-amino-2-methyl-6-nitro-4-phenylquinazolin-4-ol Chemical compound NN1C(=NC2=CC=C(C=C2C1(C1=CC=CC=C1)O)[N+](=O)[O-])C UZXMWIGOTGGWPU-UHFFFAOYSA-N 0.000 description 4
- FDIDQVQHCGSJMT-UHFFFAOYSA-N 3-amino-6-nitro-4-phenylquinazolin-4-ol Chemical compound NN1C=NC2=CC=C(C=C2C1(C1=CC=CC=C1)O)[N+](=O)[O-] FDIDQVQHCGSJMT-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 229940106681 chloroacetic acid Drugs 0.000 description 4
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 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 4
- 238000010992 reflux Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 3
- PZPZDEIASIKHPY-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-phenylmethanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 PZPZDEIASIKHPY-UHFFFAOYSA-N 0.000 description 3
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 3
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 3
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
- VWHPCNYXEBGHQF-UHFFFAOYSA-N 3-amino-2,6-dimethyl-4-phenylquinazolin-4-ol Chemical compound NN1C(C)=NC2=CC=C(C)C=C2C1(O)C1=CC=CC=C1 VWHPCNYXEBGHQF-UHFFFAOYSA-N 0.000 description 3
- IEQYCNKKNGEMAN-UHFFFAOYSA-N 3-amino-6-chloro-2-methyl-4-phenylquinazolin-4-ol Chemical compound NN1C(C)=NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1 IEQYCNKKNGEMAN-UHFFFAOYSA-N 0.000 description 3
- IIEZZJWHRMCMML-UHFFFAOYSA-N 3-amino-6-chloro-4-(2-fluorophenyl)quinazolin-4-ol Chemical compound NN1C=NC2=CC=C(C=C2C1(O)C1=C(C=CC=C1)F)Cl IIEZZJWHRMCMML-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- DNMANFUDPSVMBH-UHFFFAOYSA-N [5-chloro-2-[3-(chloromethyl)-1,2,4-triazol-4-yl]phenyl]-phenylmethanone;hydrochloride Chemical compound Cl.ClCC1=NN=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 DNMANFUDPSVMBH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- AXPOBLRMPCKWIT-UHFFFAOYSA-N 3-amino-4-phenyl-6-(trifluoromethyl)quinazolin-4-ol Chemical compound NN1C=NC2=CC=C(C=C2C1(C1=CC=CC=C1)O)C(F)(F)F AXPOBLRMPCKWIT-UHFFFAOYSA-N 0.000 description 2
- BQFFHUASKUKCMD-UHFFFAOYSA-N 3-amino-6-chloro-4-(2-chlorophenyl)quinazolin-4-ol Chemical compound NN1C=NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1Cl BQFFHUASKUKCMD-UHFFFAOYSA-N 0.000 description 2
- WQXVDQYPSMONGQ-UHFFFAOYSA-N 3-amino-6-chloro-4-(4-methoxyphenyl)quinazolin-4-ol Chemical compound NN1C=NC2=CC=C(C=C2C1(C1=CC=C(C=C1)OC)O)Cl WQXVDQYPSMONGQ-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 2
- GAXZKXGNLYXGNR-UHFFFAOYSA-N ethyl N-(2-benzoyl-4-nitrophenyl)methanimidate Chemical compound C(C)OC=NC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)[N+](=O)[O-] GAXZKXGNLYXGNR-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- AOZBUHWFXIOKQF-UHFFFAOYSA-N ethyl n-(2-benzoyl-4-chlorophenyl)ethanimidate Chemical compound CCOC(C)=NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 AOZBUHWFXIOKQF-UHFFFAOYSA-N 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000000659 freezing mixture Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- IMDBCUZFBKBACV-UHFFFAOYSA-N n'-(2-benzoyl-4-chlorophenyl)-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 IMDBCUZFBKBACV-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003246 quinazolines Chemical class 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
- FUKOTTQGWQVMQB-UHFFFAOYSA-N (2-bromoacetyl) 2-bromoacetate Chemical compound BrCC(=O)OC(=O)CBr FUKOTTQGWQVMQB-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- VDDAVZWCRBHDLQ-UHFFFAOYSA-N 2-phenylquinazoline Chemical compound C1=CC=CC=C1C1=NC=C(C=CC=C2)C2=N1 VDDAVZWCRBHDLQ-UHFFFAOYSA-N 0.000 description 1
- BXBSDHSVTCGOFC-UHFFFAOYSA-N 3-amino-4-phenylquinazolin-4-ol Chemical compound NN1C=NC2=CC=CC=C2C1(O)C1=CC=CC=C1 BXBSDHSVTCGOFC-UHFFFAOYSA-N 0.000 description 1
- BLYWAXNJULTJLN-UHFFFAOYSA-N 3-amino-6-chloro-4-(2-chlorophenyl)-2-methylquinazolin-4-ol Chemical compound NN1C(C)=NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1Cl BLYWAXNJULTJLN-UHFFFAOYSA-N 0.000 description 1
- FYPMXJFSUJYXPP-UHFFFAOYSA-N 3-amino-6-methoxy-4-phenylquinazolin-4-ol Chemical compound NN1C=NC2=CC=C(C=C2C1(C1=CC=CC=C1)O)OC FYPMXJFSUJYXPP-UHFFFAOYSA-N 0.000 description 1
- DFCAASWTVOVKKZ-UHFFFAOYSA-N 3-amino-6-methyl-4-phenylquinazolin-4-ol Chemical compound NN1C=NC2=CC=C(C=C2C1(C1=CC=CC=C1)O)C DFCAASWTVOVKKZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UGHRQJOWHVJDOR-UHFFFAOYSA-N C(=O)NC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)C(F)(F)F Chemical compound C(=O)NC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)C(F)(F)F UGHRQJOWHVJDOR-UHFFFAOYSA-N 0.000 description 1
- KRBFUPVLMXDYGO-UHFFFAOYSA-N CN(C)C=NC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)OC Chemical compound CN(C)C=NC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)OC KRBFUPVLMXDYGO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- AFTOYQREHQCUIB-UHFFFAOYSA-N ClC=1C=CC(=C(C(=O)C2=C(C=CC=C2)F)C1)NC=O Chemical compound ClC=1C=CC(=C(C(=O)C2=C(C=CC=C2)F)C1)NC=O AFTOYQREHQCUIB-UHFFFAOYSA-N 0.000 description 1
- HMBRVDQHILYKRN-UHFFFAOYSA-N ClC=1C=CC(=C(C(=O)C2=CC=C(C=C2)OC)C=1)NC=O Chemical compound ClC=1C=CC(=C(C(=O)C2=CC=C(C=C2)OC)C=1)NC=O HMBRVDQHILYKRN-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- WBXXIQDTKCKNTG-UHFFFAOYSA-N N'-(2-benzoyl-4-nitrophenyl)-N,N-dimethylmethanimidamide Chemical compound CN(C)C=NC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)[N+](=O)[O-] WBXXIQDTKCKNTG-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CNCSRKWHUULEDB-UHFFFAOYSA-N [2-[3-(chloromethyl)-1,2,4-triazol-4-yl]-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound FC(F)(F)C1=CC(C(=O)C2=CC=CC=C2)=C(C=C1)N1C=NN=C1CCl CNCSRKWHUULEDB-UHFFFAOYSA-N 0.000 description 1
- WADQPAMHVOGKMH-UHFFFAOYSA-N [2-[3-(chloromethyl)-1,2,4-triazol-4-yl]-5-nitrophenyl]-phenylmethanone Chemical compound ClCC1=NN=CN1C1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)[N+](=O)[O-] WADQPAMHVOGKMH-UHFFFAOYSA-N 0.000 description 1
- DVJBEKKCYUFDDM-UHFFFAOYSA-N [2-[3-(chloromethyl)-1,2,4-triazol-4-yl]phenyl]-phenylmethanone Chemical compound ClCC1=NN=CN1C1=C(C(=O)C2=CC=CC=C2)C=CC=C1 DVJBEKKCYUFDDM-UHFFFAOYSA-N 0.000 description 1
- RBWJIUYBFAQPHB-UHFFFAOYSA-N [2-[3-(chloromethyl)-5-methyl-1,2,4-triazol-4-yl]-5-nitrophenyl]-phenylmethanone Chemical compound CC1=NN=C(CCl)N1C1=C(C=C(C=C1)[N+]([O-])=O)C(=O)C1=CC=CC=C1 RBWJIUYBFAQPHB-UHFFFAOYSA-N 0.000 description 1
- IGAVJXNWXRLHDP-UHFFFAOYSA-N [5-chloro-2-[3-(chloromethyl)-1,2,4-triazol-4-yl]phenyl]-(2-chlorophenyl)methanone Chemical compound ClCC1=NN=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl IGAVJXNWXRLHDP-UHFFFAOYSA-N 0.000 description 1
- ZFAYQBSOGTUALH-UHFFFAOYSA-N [5-chloro-2-[3-(chloromethyl)-1,2,4-triazol-4-yl]phenyl]-(2-fluorophenyl)methanone Chemical compound ClC=1C=CC(=C(C(=O)C2=C(C=CC=C2)F)C1)N1C(=NN=C1)CCl ZFAYQBSOGTUALH-UHFFFAOYSA-N 0.000 description 1
- OCFIFDKHQAXLOL-UHFFFAOYSA-N [5-chloro-2-[3-(chloromethyl)-1,2,4-triazol-4-yl]phenyl]-(4-methoxyphenyl)methanone Chemical compound COC1=CC=C(C=C1)C(=O)C1=C(C=CC(Cl)=C1)N1C=NN=C1CCl OCFIFDKHQAXLOL-UHFFFAOYSA-N 0.000 description 1
- KBWXJZXYNPXORC-UHFFFAOYSA-N [5-chloro-2-[3-(chloromethyl)-1,2,4-triazol-4-yl]phenyl]-phenylmethanone Chemical compound ClCC1=NN=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 KBWXJZXYNPXORC-UHFFFAOYSA-N 0.000 description 1
- CPBUCUDVFXOMHN-UHFFFAOYSA-N [5-chloro-2-[3-(chloromethyl)-5-methyl-1,2,4-triazol-4-yl]phenyl]-phenylmethanone Chemical compound CC1=NN=C(CCl)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 CPBUCUDVFXOMHN-UHFFFAOYSA-N 0.000 description 1
- GTRWBBPANWZXAU-UHFFFAOYSA-N [5-chloro-2-[3-(iodomethyl)-5-methyl-1,2,4-triazol-4-yl]phenyl]-phenylmethanone Chemical compound CC1=NN=C(CI)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 GTRWBBPANWZXAU-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 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
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- XCPXPFNKTCFWTA-UHFFFAOYSA-N ethyl carbonobromidate Chemical compound CCOC(Br)=O XCPXPFNKTCFWTA-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960004011 methenamine Drugs 0.000 description 1
- PTCDPYRWMWZMCE-UHFFFAOYSA-N methyl n-(2-benzoyl-4-methylphenyl)ethanimidate Chemical compound COC(C)=NC1=CC=C(C)C=C1C(=O)C1=CC=CC=C1 PTCDPYRWMWZMCE-UHFFFAOYSA-N 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- DSPFYCLSZSPMTO-UHFFFAOYSA-N n-(2-benzoyl-4-chlorophenyl)formamide Chemical compound ClC1=CC=C(NC=O)C(C(=O)C=2C=CC=CC=2)=C1 DSPFYCLSZSPMTO-UHFFFAOYSA-N 0.000 description 1
- FPFNOZQDAQHPOZ-UHFFFAOYSA-N n-(2-benzoylphenyl)formamide Chemical compound O=CNC1=CC=CC=C1C(=O)C1=CC=CC=C1 FPFNOZQDAQHPOZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000007958 sleep Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KYTREVLPRJOBEM-UHFFFAOYSA-N triazolo[4,5-i][1,2]benzodiazepine Chemical class C1=CC2=CC=CN=NC2=C2C1=NN=N2 KYTREVLPRJOBEM-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO743997A NO134910C (enrdf_load_html_response) | 1970-10-07 | 1974-11-06 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8867570A JPS4925952B1 (enrdf_load_html_response) | 1970-10-07 | 1970-10-07 | |
| JP4362471A JPS5421352B1 (enrdf_load_html_response) | 1971-06-17 | 1971-06-17 | |
| JP6994971A JPS5246959B2 (enrdf_load_html_response) | 1971-09-08 | 1971-09-08 | |
| NO367271A NO133671C (enrdf_load_html_response) | 1970-10-07 | 1971-10-06 | |
| NO743997A NO134910C (enrdf_load_html_response) | 1970-10-07 | 1974-11-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134910B true NO134910B (enrdf_load_html_response) | 1976-09-27 |
| NO134910C NO134910C (enrdf_load_html_response) | 1977-01-05 |
Family
ID=27522330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO743997A NO134910C (enrdf_load_html_response) | 1970-10-07 | 1974-11-06 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO134910C (enrdf_load_html_response) |
-
1974
- 1974-11-06 NO NO743997A patent/NO134910C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO134910C (enrdf_load_html_response) | 1977-01-05 |
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