NO133895B - - Google Patents
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- Publication number
- NO133895B NO133895B NO423471A NO423471A NO133895B NO 133895 B NO133895 B NO 133895B NO 423471 A NO423471 A NO 423471A NO 423471 A NO423471 A NO 423471A NO 133895 B NO133895 B NO 133895B
- Authority
- NO
- Norway
- Prior art keywords
- parts
- mixture
- volume
- benzodiazepine
- phenyl
- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 claims description 12
- HDQYKTQKHDIKRF-UHFFFAOYSA-N 1,2-benzodiazepin-2-ylhydrazine Chemical class NNN1C=CC=C2C=CC=CC2=N1 HDQYKTQKHDIKRF-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000000543 intermediate Substances 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229940049706 benzodiazepine Drugs 0.000 claims description 4
- 150000001557 benzodiazepines Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 24
- 239000013078 crystal Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- 238000000921 elemental analysis Methods 0.000 description 15
- 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 13
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- IEGKHNXXLDCDTE-UHFFFAOYSA-N 1,2-benzodiazepin-2-amine Chemical compound NN1C=CC=C2C=CC=CC2=N1 IEGKHNXXLDCDTE-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- GWSXDWFXNVOIIC-UHFFFAOYSA-N (7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-yl)hydrazine Chemical compound N=1CC(NN)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 GWSXDWFXNVOIIC-UHFFFAOYSA-N 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001409 amidines Chemical class 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- CWFCXHIENFOUBG-UHFFFAOYSA-N [7-chloro-3-(2-methylpropyl)-5-phenyl-3h-1,4-benzodiazepin-2-yl]hydrazine Chemical compound C12=CC(Cl)=CC=C2N=C(NN)C(CC(C)C)N=C1C1=CC=CC=C1 CWFCXHIENFOUBG-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- WCMAUNJFJLYSRI-UHFFFAOYSA-N (7-methyl-5-phenyl-3h-1,4-benzodiazepin-2-yl)hydrazine Chemical compound C12=CC(C)=CC=C2N=C(NN)CN=C1C1=CC=CC=C1 WCMAUNJFJLYSRI-UHFFFAOYSA-N 0.000 description 1
- ZGBRDDCNIPCLMZ-UHFFFAOYSA-N (7-nitro-5-phenyl-3h-1,4-benzodiazepin-2-yl)hydrazine Chemical compound N=1CC(NN)=NC2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 ZGBRDDCNIPCLMZ-UHFFFAOYSA-N 0.000 description 1
- FWEBLHYEGFAQCZ-UHFFFAOYSA-N 2-[(2-aminophenyl)methylideneamino]-2-phenylacetonitrile Chemical class NC1=C(C=NC(C#N)C2=CC=CC=C2)C=CC=C1 FWEBLHYEGFAQCZ-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- CCXDTSHAFSPWMG-UHFFFAOYSA-N 5-phenyl-3h-1,4-benzodiazepin-2-amine Chemical compound N=1CC(N)=NC2=CC=CC=C2C=1C1=CC=CC=C1 CCXDTSHAFSPWMG-UHFFFAOYSA-N 0.000 description 1
- DBFLXAXACNTBEP-UHFFFAOYSA-N 5-phenyl-3h-1,4-benzodiazepine Chemical compound N=1CC=NC2=CC=CC=C2C=1C1=CC=CC=C1 DBFLXAXACNTBEP-UHFFFAOYSA-N 0.000 description 1
- GAISEDVHTOHOCO-UHFFFAOYSA-N 5-phenyl-7-(trifluoromethyl)-3h-1,4-benzodiazepin-2-amine Chemical compound N=1CC(N)=NC2=CC=C(C(F)(F)F)C=C2C=1C1=CC=CC=C1 GAISEDVHTOHOCO-UHFFFAOYSA-N 0.000 description 1
- -1 7-chloro-2-hydrazino-5-phenyl-3H-1,3-benzodiazepine Chemical compound 0.000 description 1
- QXNZVHPJLBVBBO-UHFFFAOYSA-N 7-chloro-3-(2-methylpropyl)-2-methylsulfanyl-5-phenyl-3h-1,4-benzodiazepine Chemical compound N=1C(CC(C)C)C(SC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 QXNZVHPJLBVBBO-UHFFFAOYSA-N 0.000 description 1
- YMFQQGSCYMGATB-UHFFFAOYSA-N 7-chloro-3-(2-methylpropyl)-5-phenyl-3h-1,4-benzodiazepin-2-amine Chemical compound C12=CC(Cl)=CC=C2N=C(N)C(CC(C)C)N=C1C1=CC=CC=C1 YMFQQGSCYMGATB-UHFFFAOYSA-N 0.000 description 1
- FZKNTBXBZONMAY-UHFFFAOYSA-N 7-chloro-5-(4-methoxyphenyl)-3h-1,4-benzodiazepin-2-amine Chemical compound C1=CC(OC)=CC=C1C1=NCC(N)=NC2=CC=C(Cl)C=C12 FZKNTBXBZONMAY-UHFFFAOYSA-N 0.000 description 1
- ULILTJWAJZIROM-UHFFFAOYSA-N 7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione Chemical compound C12=CC(Cl)=CC=C2NC(=S)CN=C1C1=CC=CC=C1 ULILTJWAJZIROM-UHFFFAOYSA-N 0.000 description 1
- UMBZDAJGYNJMGS-UHFFFAOYSA-N 7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-amine Chemical compound N=1CC(N)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 UMBZDAJGYNJMGS-UHFFFAOYSA-N 0.000 description 1
- TVPIWCSCVOUSLA-UHFFFAOYSA-N 7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-amine;dihydrochloride Chemical compound Cl.Cl.N=1CC(N)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 TVPIWCSCVOUSLA-UHFFFAOYSA-N 0.000 description 1
- MAGHIESVKJMHKN-UHFFFAOYSA-N 7-methoxy-5-phenyl-3h-1,4-benzodiazepin-2-amine Chemical compound C12=CC(OC)=CC=C2N=C(N)CN=C1C1=CC=CC=C1 MAGHIESVKJMHKN-UHFFFAOYSA-N 0.000 description 1
- CKLBCCMYEQGUCZ-UHFFFAOYSA-N 7-methyl-5-phenyl-3h-1,4-benzodiazepin-2-amine Chemical compound C12=CC(C)=CC=C2N=C(N)CN=C1C1=CC=CC=C1 CKLBCCMYEQGUCZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- GQZZWGZHSUQJNS-UHFFFAOYSA-N [7-chloro-5-(4-methoxyphenyl)-3h-1,4-benzodiazepin-2-yl]hydrazine Chemical compound C1=CC(OC)=CC=C1C1=NCC(NN)=NC2=CC=C(Cl)C=C12 GQZZWGZHSUQJNS-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008361 aminoacetonitriles Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QUXOOPXHOIPUOJ-UHFFFAOYSA-N n'-(7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-yl)-2-phenylacetohydrazide Chemical compound C12=CC(Cl)=CC=C2N=C(NNC(=O)CC=2C=CC=CC=2)CN=C1C1=CC=CC=C1 QUXOOPXHOIPUOJ-UHFFFAOYSA-N 0.000 description 1
- RIYMFZCORTVORQ-UHFFFAOYSA-N n'-(7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-yl)acetohydrazide Chemical compound N=1CC(NNC(=O)C)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 RIYMFZCORTVORQ-UHFFFAOYSA-N 0.000 description 1
- BAHBJBUUVMGWBD-UHFFFAOYSA-N n'-(7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-yl)propanehydrazide Chemical compound N=1CC(NNC(=O)CC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 BAHBJBUUVMGWBD-UHFFFAOYSA-N 0.000 description 1
- GRAZLATXVZRMNL-UHFFFAOYSA-N n'-[(7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-yl)amino]ethanimidamide Chemical compound N=1CC(NN=C(N)C)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 GRAZLATXVZRMNL-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO423471A NO133895C (ja) | 1968-11-05 | 1971-11-16 |
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8081368 | 1968-11-05 | ||
| JP9292968A JPS4843754B1 (ja) | 1968-12-17 | 1968-12-17 | |
| JP9293168 | 1968-12-17 | ||
| JP9293068 | 1968-12-17 | ||
| JP9292868 | 1968-12-17 | ||
| JP9518768A JPS4916436B1 (ja) | 1968-12-25 | 1968-12-25 | |
| JP1070269A JPS4920596B1 (ja) | 1969-02-13 | 1969-02-13 | |
| NO436869A NO126325B (ja) | 1968-11-05 | 1969-11-04 | |
| NO423471A NO133895C (ja) | 1968-11-05 | 1971-11-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133895B true NO133895B (ja) | 1976-04-05 |
| NO133895C NO133895C (ja) | 1976-07-14 |
Family
ID=27576615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO423471A NO133895C (ja) | 1968-11-05 | 1971-11-16 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO133895C (ja) |
-
1971
- 1971-11-16 NO NO423471A patent/NO133895C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO133895C (ja) | 1976-07-14 |
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