PL91876B1 - New 6-aza-3h-1,4-benzodiazepines[au4993172a] - Google Patents
New 6-aza-3h-1,4-benzodiazepines[au4993172a] Download PDFInfo
- Publication number
- PL91876B1 PL91876B1 PL1972175581A PL17558172A PL91876B1 PL 91876 B1 PL91876 B1 PL 91876B1 PL 1972175581 A PL1972175581 A PL 1972175581A PL 17558172 A PL17558172 A PL 17558172A PL 91876 B1 PL91876 B1 PL 91876B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- aza
- carbon atoms
- chloro
- group
- Prior art date
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- 229940049706 benzodiazepine Drugs 0.000 title claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- -1 aliphatic mono- Chemical class 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000375 suspending agent Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OGAHUEVSKIVFRF-UHFFFAOYSA-N [1-acetyl-7-chloro-5-(2-chlorophenyl)-2-oxo-3H-pyrido[3,2-e][1,4]diazepin-3-yl] acetate Chemical compound CC(=O)OC1N=C(C2=C(Cl)C=CC=C2)C2=NC(Cl)=CC=C2N(C(C)=O)C1=O OGAHUEVSKIVFRF-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- CMEPUAROFJSGJN-UHFFFAOYSA-N 1,4-dioxan-2-ylmethanol Chemical compound OCC1COCCO1 CMEPUAROFJSGJN-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- BTQDZLVHRYXJDK-UHFFFAOYSA-N 3h-pyrido[3,2-e][1,4]diazepine Chemical class C1=NCC=NC2=CC=CN=C21 BTQDZLVHRYXJDK-UHFFFAOYSA-N 0.000 description 1
- MKJXSZNGGPAISN-UHFFFAOYSA-N 7-chloro-3-hydroxy-5-phenyl-1,3-dihydropyrido[3,2-e][1,4]diazepin-2-one Chemical compound C12=NC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 MKJXSZNGGPAISN-UHFFFAOYSA-N 0.000 description 1
- LKFURKIXTDVVSZ-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-methyl-3H-pyrido[3,2-e][1,4]diazepin-2-one Chemical compound CN1C2=CC=C(Cl)N=C2C(=NCC1=O)C1=C(Cl)C=CC=C1 LKFURKIXTDVVSZ-UHFFFAOYSA-N 0.000 description 1
- VBDSHKZRBJQWFJ-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-3-hydroxy-1,3-dihydropyrido[3,2-e][1,4]diazepin-2-one Chemical compound OC1N=C(C2=C(F)C=CC=C2)C2=NC(Cl)=CC=C2NC1=O VBDSHKZRBJQWFJ-UHFFFAOYSA-N 0.000 description 1
- PMMIUMNVGBRIKB-UHFFFAOYSA-N 7-chloro-5-phenyl-1,3-dihydropyrido[3,2-e][1,4]diazepin-2-one Chemical compound C12=NC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 PMMIUMNVGBRIKB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- ABHFDGMIPURLMM-UHFFFAOYSA-N CC(=O)OC1N=C(C2=CC=CC=C2)C2=NC(Cl)=CC=C2N(C(C)=O)C1=O Chemical compound CC(=O)OC1N=C(C2=CC=CC=C2)C2=NC(Cl)=CC=C2N(C(C)=O)C1=O ABHFDGMIPURLMM-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 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
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JEJOFYTVMFVKQA-UHFFFAOYSA-N lopirazepam Chemical compound C12=NC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1Cl JEJOFYTVMFVKQA-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000725 suspension Substances 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
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT1060471A AT333284B (de) | 1971-12-09 | 1971-12-09 | Verfahren zur herstellung von neuen 6-aza-3h-1,4-benzodiazepinen, deren optischen isomeren und deren salzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL91876B1 true PL91876B1 (en) | 1977-03-31 |
Family
ID=3623479
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972175581A PL91876B1 (en) | 1971-12-09 | 1972-12-07 | New 6-aza-3h-1,4-benzodiazepines[au4993172a] |
| PL1972175582A PL91828B1 (en) | 1971-12-09 | 1972-12-07 | New 6-aza-3h-1,4-benzodiazepines[au4993172a] |
| PL1972159365A PL89682B1 (en) | 1971-12-09 | 1972-12-07 | New 6-aza-3h-1,4-benzodiazepines[au4993172a] |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972175582A PL91828B1 (en) | 1971-12-09 | 1972-12-07 | New 6-aza-3h-1,4-benzodiazepines[au4993172a] |
| PL1972159365A PL89682B1 (en) | 1971-12-09 | 1972-12-07 | New 6-aza-3h-1,4-benzodiazepines[au4993172a] |
Country Status (26)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2364636C2 (de) * | 1973-12-24 | 1982-11-04 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von 2-Benzoyl-6-chlor-3-nitro-pyridinen |
| EP0032516B1 (en) * | 1980-01-16 | 1984-05-02 | Lacer, S.A. | New 2-halo-pyridines, their production and pharmaceutical compositions |
| JPS60132610A (ja) * | 1983-12-20 | 1985-07-15 | Japan Organo Co Ltd | 汚泥脱水装置 |
| JPS6219221A (ja) * | 1985-07-16 | 1987-01-28 | Chiyoda Chem Eng & Constr Co Ltd | 原液中の微細粒子を除去する濾過方法と濾過装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3314941A (en) * | 1964-06-23 | 1967-04-18 | American Cyanamid Co | Novel substituted pyridodiazepins |
| US3523939A (en) * | 1967-07-03 | 1970-08-11 | Hoffmann La Roche | 5-(2,6-disubstituted phenyl)-1,4-benzodiazepines and methods for their preparation |
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1971
- 1971-12-09 AT AT1060471A patent/AT333284B/de not_active IP Right Cessation
- 1971-12-09 AT AT902174A patent/AT332877B/de active
- 1971-12-09 AT AT902274A patent/AT332878B/de active
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1972
- 1972-11-29 ES ES409089A patent/ES409089A1/es not_active Expired
- 1972-11-29 ES ES409090A patent/ES409090A1/es not_active Expired
- 1972-11-30 FI FI3390/72A patent/FI54710C/fi active
- 1972-11-30 ZA ZA728497A patent/ZA728497B/xx unknown
- 1972-12-05 DE DE2259471A patent/DE2259471C2/de not_active Expired
- 1972-12-05 SE SE7215858A patent/SE404803B/xx unknown
- 1972-12-06 FR FR7243359A patent/FR2162482B1/fr not_active Expired
- 1972-12-06 HU HUDE799A patent/HU169468B/hu unknown
- 1972-12-06 EG EG502/72A patent/EG10918A/xx active
- 1972-12-07 IT IT7254583Q patent/IT1035053B/it active
- 1972-12-07 RO RO7281196A patent/RO65263A/ro unknown
- 1972-12-07 RO RO7281197A patent/RO67345A/ro unknown
- 1972-12-07 RO RO7200073075A patent/RO62312A/ro unknown
- 1972-12-07 PL PL1972175581A patent/PL91876B1/pl unknown
- 1972-12-07 PL PL1972175582A patent/PL91828B1/pl unknown
- 1972-12-07 PL PL1972159365A patent/PL89682B1/pl unknown
- 1972-12-07 RO RO7281195A patent/RO65264A/ro unknown
- 1972-12-07 NL NLAANVRAGE7216621,A patent/NL171986C/xx not_active IP Right Cessation
- 1972-12-08 GB GB5688372A patent/GB1400755A/en not_active Expired
- 1972-12-08 CS CS728424A patent/CS212736B2/cs unknown
- 1972-12-08 IL IL41034A patent/IL41034A/en unknown
- 1972-12-08 DK DK615172AA patent/DK138425B/da not_active IP Right Cessation
- 1972-12-08 YU YU03059/72A patent/YU305972A/xx unknown
- 1972-12-08 SU SU1855103A patent/SU468423A3/ru active
- 1972-12-08 NO NO4536/72A patent/NO137094C/no unknown
- 1972-12-08 BE BE792541A patent/BE792541A/xx not_active IP Right Cessation
- 1972-12-09 JP JP12387872A patent/JPS569509B2/ja not_active Expired
- 1972-12-11 CH CH1794972A patent/CH594665A5/xx not_active IP Right Cessation
- 1972-12-11 DD DD167428A patent/DD105448A5/xx unknown
- 1972-12-11 CH CH1526076A patent/CH603645A5/xx not_active IP Right Cessation
- 1972-12-11 CH CH1506576A patent/CH605946A5/xx not_active IP Right Cessation
- 1972-12-11 AU AU49931/72A patent/AU473253B2/en not_active Expired
- 1972-12-11 CH CH1506676A patent/CH603644A5/xx not_active IP Right Cessation
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1973
- 1973-09-10 AR AR250008A patent/AR201201A1/es active
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1974
- 1974-03-20 AR AR252867A patent/AR200309A1/es active
- 1974-07-08 SU SU742041603A patent/SU674675A3/ru active
- 1974-07-08 SU SU7402042686A patent/SU564809A3/ru active
- 1974-10-15 SU SU7402067128A patent/SU574156A3/ru active
- 1974-10-31 AR AR256352A patent/AR203311A1/es active
- 1974-11-11 AT AT902074A patent/AT338798B/de not_active IP Right Cessation
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1980
- 1980-04-15 JP JP5022280A patent/JPS55147282A/ja active Granted
- 1980-04-15 JP JP5022180A patent/JPS5625180A/ja active Granted
- 1980-04-15 JP JP5022380A patent/JPS5625181A/ja active Granted
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1981
- 1981-05-07 YU YU01168/81A patent/YU116881A/xx unknown
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