PL82688B1 - Benzodiazepine derivatives preparation[gb1276909a] - Google Patents
Benzodiazepine derivatives preparation[gb1276909a] Download PDFInfo
- Publication number
- PL82688B1 PL82688B1 PL1969136465A PL13646569A PL82688B1 PL 82688 B1 PL82688 B1 PL 82688B1 PL 1969136465 A PL1969136465 A PL 1969136465A PL 13646569 A PL13646569 A PL 13646569A PL 82688 B1 PL82688 B1 PL 82688B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- chloro
- tetrahydro
- benzodiazepinone
- phenyl
- Prior art date
Links
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title claims abstract description 4
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 title claims abstract description 4
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- -1 alkyl radicals Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 5
- 239000007858 starting material Substances 0.000 abstract description 3
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 2
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 238000009835 boiling Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 4
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229940102253 isopropanolamine Drugs 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- GTLLBGFJGUJABH-UHFFFAOYSA-N (2-amino-5-bromophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1Cl GTLLBGFJGUJABH-UHFFFAOYSA-N 0.000 description 3
- LXJVUGANBDAASB-UHFFFAOYSA-N (2-amino-5-bromophenyl)-phenylmethanone Chemical compound NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1 LXJVUGANBDAASB-UHFFFAOYSA-N 0.000 description 3
- KWZYIAJRFJVQDO-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl KWZYIAJRFJVQDO-UHFFFAOYSA-N 0.000 description 3
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- BHIQWPLMSSPGNB-UHFFFAOYSA-N (2-amino-3,5-dimethylphenyl)-phenylmethanone Chemical compound CC1=CC(C)=C(N)C(C(=O)C=2C=CC=CC=2)=C1 BHIQWPLMSSPGNB-UHFFFAOYSA-N 0.000 description 2
- ZVPLWDRTHNDLQO-UHFFFAOYSA-N (2-amino-5-chloro-3-methylphenyl)-phenylmethanone Chemical compound CC1=CC(Cl)=CC(C(=O)C=2C=CC=CC=2)=C1N ZVPLWDRTHNDLQO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FUKOTTQGWQVMQB-UHFFFAOYSA-N (2-bromoacetyl) 2-bromoacetate Chemical compound BrCC(=O)OC(=O)CBr FUKOTTQGWQVMQB-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- BASRYQBPQWFPEF-UHFFFAOYSA-N [5-chloro-2-(ethylamino)phenyl]-phenylmethanone Chemical compound CCNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 BASRYQBPQWFPEF-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- WSXPCBBBFNSXNG-UHFFFAOYSA-N (2-amino-3,5-dichlorophenyl)-phenylmethanone Chemical compound NC1=C(Cl)C=C(Cl)C=C1C(=O)C1=CC=CC=C1 WSXPCBBBFNSXNG-UHFFFAOYSA-N 0.000 description 1
- GTGMXPIQRQSORU-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-fluorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F GTGMXPIQRQSORU-UHFFFAOYSA-N 0.000 description 1
- VKTIPANBPNEKBN-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC(Cl)=CC=C1N VKTIPANBPNEKBN-UHFFFAOYSA-N 0.000 description 1
- TUFWUVGXYPKWNV-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(4-nitrophenyl)methanone Chemical compound ClC=1C=CC(=C(C(=O)C2=CC=C(C=C2)[N+](=O)[O-])C=1)N TUFWUVGXYPKWNV-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- PKBWSVYZZFPORW-UHFFFAOYSA-N 1-(benzylideneamino)ethanol Chemical class CC(O)N=CC1=CC=CC=C1 PKBWSVYZZFPORW-UHFFFAOYSA-N 0.000 description 1
- HNYFXDWMIDCTPH-UHFFFAOYSA-N 1-[[(2-amino-5-bromophenyl)-(2-chlorophenyl)methylidene]amino]propan-2-ol Chemical compound NC1=C(C(C2=C(C=CC=C2)Cl)=NCC(O)C)C=C(C=C1)Br HNYFXDWMIDCTPH-UHFFFAOYSA-N 0.000 description 1
- QKGHBPBXZNOVTL-UHFFFAOYSA-N 1-[[(2-amino-5-chlorophenyl)-(2-methylphenyl)methylidene]amino]propan-2-ol Chemical compound NC1=C(C(C2=C(C=CC=C2)C)=NCC(O)C)C=C(C=C1)Cl QKGHBPBXZNOVTL-UHFFFAOYSA-N 0.000 description 1
- DYOYRAOVVFWIGJ-UHFFFAOYSA-N 2,4-dimethyl-6-(2-phenyl-1,3-oxazolidin-2-yl)aniline Chemical compound CC=1C(=C(C=C(C1)C)C1(OCCN1)C1=CC=CC=C1)N DYOYRAOVVFWIGJ-UHFFFAOYSA-N 0.000 description 1
- KJGWZWJHDVNZAW-UHFFFAOYSA-N 2,4-dimethyl-6-(5-methyl-2-phenyl-1,3-oxazolidin-2-yl)aniline Chemical compound CC=1C(=C(C=C(C1)C)C1(OC(CN1)C)C1=CC=CC=C1)N KJGWZWJHDVNZAW-UHFFFAOYSA-N 0.000 description 1
- MLNWJLSLQSUYCO-UHFFFAOYSA-N 2-[[(2-amino-5-bromophenyl)-(2-chlorophenyl)methylidene]amino]propan-1-ol Chemical compound NC1=C(C(C2=C(C=CC=C2)Cl)=NC(CO)C)C=C(C=C1)Br MLNWJLSLQSUYCO-UHFFFAOYSA-N 0.000 description 1
- VRZYTUVCIRDLCK-UHFFFAOYSA-N 2-[[(2-amino-5-chlorophenyl)-(2-chlorophenyl)methylidene]amino]ethanol Chemical compound NC1=CC=C(Cl)C=C1C(=NCCO)C1=CC=CC=C1Cl VRZYTUVCIRDLCK-UHFFFAOYSA-N 0.000 description 1
- IPZIWCWMDPINKE-UHFFFAOYSA-N 2-[[(2-amino-5-chlorophenyl)-(2-chlorophenyl)methylidene]amino]propan-1-ol Chemical compound NC1=C(C(C2=C(C=CC=C2)Cl)=NC(CO)C)C=C(C=C1)Cl IPZIWCWMDPINKE-UHFFFAOYSA-N 0.000 description 1
- DRRPSTDRWJZCBV-UHFFFAOYSA-N 2-[[(2-amino-5-chlorophenyl)-phenylmethylidene]amino]ethanol Chemical compound NC1=CC=C(Cl)C=C1C(=NCCO)C1=CC=CC=C1 DRRPSTDRWJZCBV-UHFFFAOYSA-N 0.000 description 1
- XNVZEGJVLJTGKZ-UHFFFAOYSA-N 2-[[(2-amino-5-chlorophenyl)-phenylmethylidene]amino]propan-1-ol Chemical compound C=1C(Cl)=CC=C(N)C=1C(=NC(CO)C)C1=CC=CC=C1 XNVZEGJVLJTGKZ-UHFFFAOYSA-N 0.000 description 1
- RIQCMHMDODNXHZ-UHFFFAOYSA-N 2-[[(2-amino-5-nitrophenyl)-phenylmethylidene]amino]propan-1-ol Chemical compound NC1=C(C(C2=CC=CC=C2)=NC(CO)C)C=C(C=C1)[N+](=O)[O-] RIQCMHMDODNXHZ-UHFFFAOYSA-N 0.000 description 1
- DWKNOLCXIFYNFV-HSZRJFAPSA-N 2-[[(2r)-1-[1-[(4-chloro-3-methylphenyl)methyl]piperidin-4-yl]-5-oxopyrrolidine-2-carbonyl]amino]-n,n,6-trimethylpyridine-4-carboxamide Chemical compound CN(C)C(=O)C1=CC(C)=NC(NC(=O)[C@@H]2N(C(=O)CC2)C2CCN(CC=3C=C(C)C(Cl)=CC=3)CC2)=C1 DWKNOLCXIFYNFV-HSZRJFAPSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- MSJLLBZKYRLPOF-UHFFFAOYSA-N 4-bromo-2-[2-(2-chlorophenyl)-5-methyl-1,3-oxazolidin-2-yl]aniline Chemical compound BrC=1C=CC(=C(C1)C1(OC(CN1)C)C1=C(C=CC=C1)Cl)N MSJLLBZKYRLPOF-UHFFFAOYSA-N 0.000 description 1
- IRWPZPMPDLRSIS-UHFFFAOYSA-N 4-chloro-2-(2-phenyl-1,3-oxazolidin-2-yl)aniline Chemical compound ClC=1C=CC(=C(C1)C1(OCCN1)C1=CC=CC=C1)N IRWPZPMPDLRSIS-UHFFFAOYSA-N 0.000 description 1
- YQUYQRNOQMUXQC-UHFFFAOYSA-N 4-chloro-2-[2-(2-chlorophenyl)-5-methyl-1,3-oxazolidin-2-yl]aniline Chemical compound ClC=1C=CC(=C(C1)C1(OC(CN1)C)C1=C(C=CC=C1)Cl)N YQUYQRNOQMUXQC-UHFFFAOYSA-N 0.000 description 1
- JEHVULXLGBRSMT-UHFFFAOYSA-N 4-chloro-2-methyl-6-(2-phenyl-1,3-oxazolidin-2-yl)aniline Chemical compound CC=1C(=C(C=C(C1)Cl)C1(OCCN1)C1=CC=CC=C1)N JEHVULXLGBRSMT-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- JJMTWGHPIRGCTE-UHFFFAOYSA-N 5-methyl-2-phenyl-1,3-oxazolidine Chemical compound O1C(C)CNC1C1=CC=CC=C1 JJMTWGHPIRGCTE-UHFFFAOYSA-N 0.000 description 1
- VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HPVUXGAKPJOZBW-UHFFFAOYSA-N [2-(benzylamino)-5-chlorophenyl]-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1NCC1=CC=CC=C1 HPVUXGAKPJOZBW-UHFFFAOYSA-N 0.000 description 1
- FUYPDDZLQLWFBR-UHFFFAOYSA-N [3-amino-5-chloro-2-[(4-chlorophenyl)methyl]phenyl]-phenylmethanone Chemical compound ClC=1C=C(C(=C(C(=O)C2=CC=CC=C2)C=1)CC1=CC=C(C=C1)Cl)N FUYPDDZLQLWFBR-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- VWUPQQFMCOQIEJ-UHFFFAOYSA-M potassium;hydrogen carbonate;hydrate Chemical compound O.[K+].OC([O-])=O VWUPQQFMCOQIEJ-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Furnace Details (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP43077500A JPS4834752B1 (enrdf_load_stackoverflow) | 1968-10-24 | 1968-10-24 | |
| JP43077504A JPS4834756B1 (enrdf_load_stackoverflow) | 1968-10-24 | 1968-10-24 | |
| JP44029908A JPS4925276B1 (enrdf_load_stackoverflow) | 1969-04-17 | 1969-04-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL82688B1 true PL82688B1 (en) | 1975-10-31 |
Family
ID=27286759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1969136465A PL82688B1 (en) | 1968-10-24 | 1969-10-23 | Benzodiazepine derivatives preparation[gb1276909a] |
Country Status (17)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH565180A5 (enrdf_load_stackoverflow) * | 1970-12-23 | 1975-08-15 | Hoffmann La Roche |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3914215A (en) * | 1967-11-27 | 1975-10-21 | Sankyo Co | Benzodiazepine derivatives and process for preparing the same |
| GB1222294A (en) * | 1968-09-19 | 1971-02-10 | Upjohn Co | Oxazinobenzodiazepine derivatives |
-
1969
- 1969-10-15 IL IL33190A patent/IL33190A/xx unknown
- 1969-10-21 BE BE740587D patent/BE740587A/xx not_active IP Right Cessation
- 1969-10-23 OA OA53762A patent/OA03155A/xx unknown
- 1969-10-23 DE DE1954065A patent/DE1954065C3/de not_active Expired
- 1969-10-23 BG BG020368A patent/BG19175A3/xx unknown
- 1969-10-23 PL PL1969136465A patent/PL82688B1/pl unknown
- 1969-10-23 NL NL6915994.A patent/NL166262C/xx not_active IP Right Cessation
- 1969-10-23 DK DK561869A patent/DK153152C/da not_active IP Right Cessation
- 1969-10-23 FR FR696936338A patent/FR2021469B1/fr not_active Expired
- 1969-10-23 NO NO04212/69A patent/NO128109B/no unknown
- 1969-10-23 IE IE1447/69A patent/IE33825B1/xx unknown
- 1969-10-23 BG BG013231A patent/BG20109A3/xx unknown
- 1969-10-24 GB GB52353/69A patent/GB1276909A/en not_active Expired
- 1969-10-24 SE SE14615/69A patent/SE366314B/xx unknown
- 1969-10-24 RO RO61341A patent/RO55843A/ro unknown
- 1969-10-24 RO RO69346A patent/RO57031A/ro unknown
- 1969-10-24 CH CH1592069A patent/CH533130A/de not_active IP Right Cessation
- 1969-10-24 FI FI693070A patent/FI49621C/fi active
- 1969-10-24 SE SE7215303A patent/SE384857B/xx unknown
-
1971
- 1971-01-01 AR AR236342A patent/AR207426A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| SE366314B (enrdf_load_stackoverflow) | 1974-04-22 |
| CH533130A (de) | 1973-01-31 |
| FR2021469B1 (enrdf_load_stackoverflow) | 1973-04-06 |
| NL6915994A (enrdf_load_stackoverflow) | 1970-04-28 |
| NO128109B (enrdf_load_stackoverflow) | 1973-10-01 |
| NL166262B (nl) | 1981-02-16 |
| AR207426A1 (es) | 1976-10-08 |
| RO57031A (enrdf_load_stackoverflow) | 1974-12-15 |
| SE384857B (sv) | 1976-05-24 |
| NL166262C (nl) | 1981-07-15 |
| DE1954065B2 (de) | 1979-01-11 |
| BG20109A3 (bg) | 1975-10-30 |
| DK153152C (da) | 1988-12-05 |
| GB1276909A (en) | 1972-06-07 |
| FI49621B (enrdf_load_stackoverflow) | 1975-04-30 |
| FR2021469A1 (enrdf_load_stackoverflow) | 1970-07-24 |
| OA03155A (fr) | 1970-12-15 |
| IE33825L (en) | 1970-04-24 |
| RO55843A (enrdf_load_stackoverflow) | 1974-02-01 |
| FI49621C (fi) | 1975-08-11 |
| DE1954065A1 (de) | 1970-08-27 |
| BG19175A3 (bg) | 1975-04-30 |
| IE33825B1 (en) | 1974-11-13 |
| DK153152B (da) | 1988-06-20 |
| IL33190A (en) | 1972-11-28 |
| DE1954065C3 (de) | 1979-09-13 |
| IL33190A0 (en) | 1969-12-31 |
| BE740587A (enrdf_load_stackoverflow) | 1970-04-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5679678A (en) | Thienithiazine derivatives | |
| US3100770A (en) | 5-pyridyl-1,4-benzodiazepine compounds | |
| US3962261A (en) | 2,3,4,5-tetra hydro-5-oxo-1-benzothiepi n-4-carboxamide 1,1-dioxides | |
| US3991064A (en) | Benzonaphthyridines | |
| PL132141B1 (en) | Process for preparing novel derivatives of dibenzoimidazoazepins | |
| US3988345A (en) | Imidazoline derivatives and the preparation thereof | |
| US3530139A (en) | Process for producing certain intermediates for 1,4-benzodiazepines | |
| US3798226A (en) | 3-acylamino-4-phenylquinolines carrying a substituent on the benzene ring | |
| US3925371A (en) | Benzothiazine-1,1-dioxides | |
| CA1049009A (en) | 6h-thieno (3,2-f)-s-triazolo (4,3-a)-(1,4) diazepines | |
| PL82688B1 (en) | Benzodiazepine derivatives preparation[gb1276909a] | |
| US3703525A (en) | Triazolo(1,5-a)(1,4)benzodiazepine derivatives | |
| US4046778A (en) | Processes for the preparation of 4-hydroxy-2H-1-benzothiopyran-3-carboxamide 1,1-dioxides | |
| US3951982A (en) | Trialkylsilyl esters of 6(substituted amino)phenyl-1,-dihydro-2-oxonicotinic acid, methods for their production and conversion to the corresponding acid chlorides | |
| US3450700A (en) | 2-tertiary amino-4h-3,1-benzoxazin-4-ones | |
| US3755300A (en) | Process for the preparation of benzodiazepine compounds | |
| JPH0576946B2 (enrdf_load_stackoverflow) | ||
| US3920687A (en) | 2,3,6,7-tetrahydro-6-phenyl-5h-imidazo(1,2-d)+8 1,4)benzodiazepin-5-ones and diazepines | |
| US3661925A (en) | Process for the preparation of 2-benzimidazolecarboxamides | |
| US3297698A (en) | Process for the preparation of quinazoline 3-oxides | |
| SE407686B (sv) | Analogiforfarande for framstellning av kondenserade pyrimidinderivat | |
| NO140860B (no) | Analogifremgangsmaate for fremstilling av fysiologisk aktive triazolo-1,5-benzodiazepiner | |
| US4116956A (en) | Benzodiazepine derivatives | |
| US3887541A (en) | 1,4-Benzodiazepine derivatives | |
| US3746701A (en) | Method for the production of benzodiazepine derivatives |