PL92569B1 - - Google Patents
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- PL92569B1 PL92569B1 PL18373771A PL18373771A PL92569B1 PL 92569 B1 PL92569 B1 PL 92569B1 PL 18373771 A PL18373771 A PL 18373771A PL 18373771 A PL18373771 A PL 18373771A PL 92569 B1 PL92569 B1 PL 92569B1
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- PL
- Poland
- Prior art keywords
- radical
- acid
- carbon atoms
- formula
- dihydro
- Prior art date
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- -1 alkoxy radical Chemical class 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical group C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 2
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims 2
- SPAGIJMPHSUYSE-UHFFFAOYSA-N Magnesium peroxide Chemical compound [Mg+2].[O-][O-] SPAGIJMPHSUYSE-UHFFFAOYSA-N 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 2
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
- MLIWQXBKMZNZNF-KUHOPJCQSA-N (2e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-KUHOPJCQSA-N 0.000 description 1
- BAVAZRNEAWBRLO-UHFFFAOYSA-N 1,2-benzodiazepin-4-one Chemical compound O=C1C=NN=C2C=CC=CC2=C1 BAVAZRNEAWBRLO-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [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
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NAHBVNMACPIHAH-HLICZWCASA-N p-ii Chemical compound C([C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H]2CSSC[C@H](NC(=O)[C@H](CC=3C=CC=CC=3)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC2=O)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O)=O)C(C)C)C1=CC=CC=C1 NAHBVNMACPIHAH-HLICZWCASA-N 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- C07D243/26—Preparation from compounds already containing the benzodiazepine skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- C07D243/28—Preparation including building-up the benzodiazepine skeleton from compounds containing no hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- C07D243/30—Preparation including building-up the benzodiazepine skeleton from compounds already containing hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- C07D243/30—Preparation including building-up the benzodiazepine skeleton from compounds already containing hetero rings
- C07D243/36—Preparation including building-up the benzodiazepine skeleton from compounds already containing hetero rings containing an indole or hydrogenated indole ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarza¬ nia nowych pochodnych benzodwuazepiny, podsta¬ wianych w pozycji 1, o wzorze 1, w którymi Ri oznacza atom wodoru, chlorowca, grupe nitrowa, cyjanowa, nizszy rodnik alkoksylowy lub rodnik trójfluorometylowy, R5 i R6 oznaczaja niezaleznie od siebie atom wodoru, chlorowca, nizszy rodnik alkilowy o 1—2 atomach wegla lub rodnik trój¬ fluorometylowy, R4 oznacza nizszy rodnik alkilo¬ wy o 1—4 atomach wegla, rodnik cykloalkdlowy o 3—6 atomach wegla, rodnik cykloalkiloalkilowy, w którym czesc cykloalkilowa zawiera 3—6 ato¬ mów wegla, a czesc alkilowa 1—4 atomów wegla, rodnik aryIowy lub rodnik aryloalkilowy, m jest równe 1 lub 2, a n' jest liczba calkowita 2 lub 3 oraz ich soli.W zwiazkach o wzorze 1 atom chlorowca moze oznaczac atom fluoru, chloru, bromu lub jodu; rodnik alkilowy moze miec lancuch prosty lub rozgaleziony; nizszy rodnik alkilowy moze na przy¬ klad oznaczac rodnik metylowy, etylowy, n-propy- lowy, izopropylowy, n-butylowy i III rzed. butylo¬ wy; nizszy rodnik alkoksylowy moze oznaczac na przyklad rodnik metoksylowy, etoksylowy, n-pro- poksylowy, izopropoksylowy, n-butoksylowy i III- -rzed. butoksylowy; rodnik cykloalkilowy moze oznaczac na przyklad rodnik cyklopropylowy, cy- klobutylowy, cyfldoheksylowy i cyklopentylowy; ro¬ dnik cykloalkiloalkilowy moze oznaczac na przy¬ klad rodnik cyfclopropylometylowy, cykfloibutylome- . tylowy, cyklopentylometylowy, cykloheksylometylo- wy, i cyklonetosyiloetyilowy; rodnik arylowy moze oznaczac na przyklad rodnik fenylowy, jedno-lub dwupodstawiony rodnik fenylowy, w którym pod¬ stawnikami w pierscieniu fenylowym moga byc ato¬ my chlorowca takie jak atom cMoru, fluoru, bromu lub jodu, nizszy rodnik alkilowy, taki jak metylowy lub etylowy, nizszy rodnik alkoksylowy, taki jak metoksylowy lub etoksylowy, grupa nitrowa i rod¬ nik trójfluorometylowy, rodnik aryloalkilowy mo¬ ze oznaczac na przyklad rodnik fenyloetylowy; ro¬ dnik alkenylowy —Cn,H2n, — ma lancuch prosty lub rozgaleziony o 2 lub 3 atomach wegla, taki na przyklad jak rodnik etylenowy, 1-metyloetylenowy, 2-metyloetylenowy lub trójmetylenowy.Pochodne benzodwuazepiny o wzorze 1, podsta¬ wione w pozycji 1 oraz ich sole sa zwiazka.mJi no¬ wymi. Nieoczekiwanie stwierdzono, ze zwiazki oraz ich dopuszczalne farmaceutycznie sole z kwasami nieorganicznymi i organicznymi maja cenne wlasci¬ wosci farmakologiczne, szczególnie uspakajajace, rozluzniajace miesnie, spazmolityczne i nasenne.Sposób wytwarzania nowych pochodnych benzo¬ dwuazepiny o wzorze 1 wedlug wynalazku polega na reakcji utleniania pochodnej benzodwuazepiny lub jej soli o wzorze 2, w którym Rlt R4, R5, R8 i sn maja znaczenie podane powyzej, a p jest równe ze¬ ro lub 1 srodkiem utleniajacym. Jako srodek utle¬ niajacy stosuje sie, na przyklad, kwas chromowy, 925693 92569 kwas azotowy, nadtlenek wodoru, organiczne kwasy nadtlenowe, takie jak kwas nadnirówkowy, nadoc¬ towy, nadbenzoesowy lub m-chloronadbenzoesowy, nadjodan sodowy, nadjodan potasowy, nadsiarczan, dwutlenek selenu, czterooctan olowiu, dwutlenek 5 mafenezg lulx czt^otlenek rutenu.Reakcje prowadzi sie zwykle w obecnosci roz¬ puszczalnika, a wybór rozpuszczalnika zalezy od zastosowanego srodka utleniajacego. Jako rozpusz¬ czalniki stosuje siie wode, chloroform, czterochlorek *° wegla, aceton, kwas octowy, kwas mrówjtpwy, kwas , aiarkowy, pirydyne, dioksan, benzen, toluen, eter, octan etylu, metanol, etanol itp. lub ich mieszani¬ ny. Temperatura reakcji zmienia sie w zaleznosci od zastosowanego srodka utleniajacego. W przypad- 15 ku, kiedy dajzy sie do otrzymania zwiazku o wzo¬ rze 1, w którym im jest równe 1 reakcje prowadzi . sie w ,¦ i^empe^ajjurze pokojowej lufo nizszej. W przypadku,; Jdy 4aSX ste do otrzymania zwiazek o wzorze 1, w którym im jest równe 2, reakcje paro- zo wadzi sie w temperaturze pokojowej lub wyzszej.Siposobem wedlug wynalazku wytwarza sie na przyklad nastepujace zwiazki: 1- / p^metylosulfonyloetylo / -5-fenylo-7^chloro-l,3- -dwuwodorp-2H-l,4-benzodwuazepinon-2 1- / p-metylosulfonyloetylo / -5-fenylo-7-cyjano-l,3- -dwuwodoro-2H-l,4-foenzodwuazepinon-2 1- / p-metylosulfonyloetylo / f-5-fe^yto-t-nittb-l,3-.i -dwuwodoro-2H-l,4-foenzodwuazepinon-2 1-7 flnmetylosuMonyloetylo / -5-fenylo-7-tmetoksylo- -l,3-dwuwodoro-2H-l,4-«benzodwuazepinon-2 1-;/^-metylosulfonyiloetylo / -5rfenylp-7-trójfluoro- nietyloTl,3-dwuwodpTO-2H-l ,4rbenzo4w^ajze(pinon-2 1- / p^metylosiulifonyloetylo / T5Tfeiiylo-7-bromo-l,3- -dwuwodow-2H-lj4-benzodwua9e!pinonr2 1 --;¦/ Pr^metyilosufkfonyiloetyilo / -5HfenyikHl^ndwu^o- d^o^^rHl,4dben^oxtwuaeej)inon^ ¦•< j. l-v/^ P-metyteuifonyloetylo / ^-metyk -5*fenyilo -7- -chlord-l,3-dwuwodoro-2IJ-l,4-benzodwuazepinon-2 l-/p-metylosulfonyloetylo / -5- / 2'ipirydylp/-7-chlo- ro-1,3-dwuwodoro-2II-l,4-foenzodwuazepinonr2 1- / Prmetylosulifoiiiyloetylo / *£- / onfluorofenylo / -7- ^chlqro-1,3-dwuwodoro-2H-l,4-benzodwuazepinon-2 1-7 ^Hmetylosuilfonyloetylo / -5- /2'-pirydyIp / -74ro- mo-1,3-dwuwodoro^2H-l,4-benzodwuazepanon-2 1- / p-metyljosulfonyloetylo / -5- /Onchlorofenylo/ -7f -chloro-l,3-dwuwodoro-2H-l,4-ibenzodwuazepinon-2 1- / ^-metylosulfohyloetylo -/'-"5- / o-tólilo / -7-chloro- -1,3-dwuwodbro-2 1-7 p-metylosulifonyloetylo / -5- / o-chiorofenylo / -7- -natrp-l j3-dwuWodoro-2H-l ,4-ibenzodwuazepinon-2 1- / p-metyiosulfonylioetylo / -5- / o-trójfluorometylo- feriyilo / -7-chloro-l ,3-dwuwodoró-2iH-l,4-toenzodwu- azepinori-2 1 -/^-etylosulfonyloetylo,/ -5-1enylo-7-chloro-1^3;-dwu- wodoro-2H- Wf^etylosulifonyloetylo /-5-fenylo-7-cyjano^M-dwu- Wodoro-2H-l,4^benzodwuazepinon-2 1- / 0-etylosulfonyloetylo-/ -5-fenylo-7-niitiro-l,3-dwu- wo4orc^2iH-l,4Hbenzod'wuaz \-1 flf-etylosulfonyloetylo / -5rfenylo-7-trójfluorome- tylo-l,3-dwuwodoro-2H-l,4-foenzodwuazepinon-2 1- / p-etylosulfonyloetylo / -5-fenylo -7-bromo -1,3- -dwuwodoro-2H-l,4-foenzodwuazepinon-2 1- / p-etylosulfonyloetylo / -5* / o*-fklorodfenylb / -7t -chloro -l]3-diwuwodoro-2H-l,4--beaizodwuazepiriph^2 1- / p-etylosulfonyloetylp / -5- / 2^pirydyio y ^7-bro- mo-1,3-dwuwodorb-2H-l ,4-ibenzodwuazepinon-2 1-7 P-etylosuLfónyloetylo / -5- / o-chlorofenylo / -7- -chloro-1,3-dwuwodoro-2H-l,4-benzodwuazepinon -2 1- /p-etylosuHfonyloetylo7-5- /o-tolilo /V7-cliloro-l,3- -dwuwodoro-2H-l,4-foenzodwuazepiLnoni# n 1- / j5-etylosulifonyloetyilo / -5- / o-ch;loxpfsnyk) / -7-ni- tTo-l,3-dwuwodoro-i2iH-l,4-(benzodwuazepinian-2 .1-7 P-propylosulfonyloetylo J -5-fenylo^7-chloro-l,3- -dwuwodoro-2fl-l,4-foenzodwuazepmon-2 4- / p-propylosulfonyloetylo / -5-fenylo / -7-nitro-l,3- -dwuwodoro-2H-l,4-ibenzodwuazepiinpn-2v l-/p-ii|ppropylosulfonyloetylo / -5- / o-chlorofenylo/- -7-chloro-l,3-dwuwodoro-2H-l,4-benzodwuazepinon - -2 : '¦-." 1- / p-izc0rópylosulfonyloetylo / -5- / b-tolijo / -7-chlo¬ ro-l ,3-dwuwcdoro-2H-l,4-benzodwuazepinon-2 1- / P-izopropylosulfonyloetylo / -5- / o-chlorofenylo /- -7-nitiro-l,3-dwuwodpro-2H-l,4nbenzodwuazepinon-2 l-/y-(metylosulifonylopropylo / -5-fenylo-7-chloro-l,3- -dwuwodoro-2iH-l,4-benzodwuazepinon-2 1- / y-metylosulfonylopropylo / -5-fenylo-7-nitro-l,3- -dwiiwodoro-2iH-l,4-benzodwuazepkion-2 1- / Y-ttietylosuifonyloprbpylo / -5- / o-fluorofenylo /- -7-chloro-l ,3-dwuwodoro-2H-l ,4-benzodwuazepinori- -2 r 1 - /Yrmetylps^lfonyloprppyló. /-5,-i /o-chlorofenylo/- -7-chloro-l,3-dwiuwodoro-2H-l,4^benzodwuazep(inon- -2 1- / Y-metylosuLfonylopropydo/ -5- / o-tolilo / -7-chlo¬ ro-l,3-dwu^vodoro-2Hrl,4-ben2odwuazepinon-2 1- / y-^nieitylosjulfonylopiropylo / -5- / o-chlprofenylo/- -7-nitrowi,3-dwuwodoro-2H-l,4-(benzodwuazepinon-2 1-^ / Y^etylosulfonyilppropylo / -5-fenylor7HqhlorQ-l,3- -dv^lrwodoro-2H*l,4-„benaodwuaizepinon-2 r l-Z^etytoulipnyloproipylo /-5-fenylo-7-nitrOrl,3j ^wuwodoro^^-l,4^benzodwuazepino^ . 1-/ y-6tylc«ull0(nylp|)r;opylo / -5-fenylo*7^trójfluoro^ metylo-lA^waw^orx-2H-l,4-(banzodwuazepinQn-2 1- / Y-etylOsuiUonylopropylo / -5^fenyao-7^bromo-l3- -dwuwodoroH2H-l,4-benzodwuazepinon-2 l-/Y-etylosUiMonylopropylo7-5-/ 2'-pirydylo /-7-chlo¬ ro-ly3-dwuwodoro-2H-l,4-benzodwiuazepdnon-2 1- / Y-etylosulifonylopropylo / -5- ./ o-fluorofenylo / -7- -chloro-1,3-dwuwodoro-2H-l,4-benzodwuazepinon-2 1- / Y-etylosuilfonylopropylo / -5- ,/ 2/-piirydylo / -7- -bromÓ-1,3-dwuw;o»doro-2H-l ,4-benzodwuazepinon-2 1- / Y^etylosuifonylopropylo / -5- / o-chlorofenylo / -7- -chloTo-1,3-dwuWodoro-2H-l,4-benzodwuazepinon-2 1- / Y-otylosulfonylopropylo / -5- /o-tolrlo/ -7-chloro- -l,3-diwuwodoro-2H-i,4-benzodwua!zepinon-2 1- / Y-ptyl -7-nitoo-l,3-dwuwpdo]X)-2H-l,4-benzodwuaze;pin^ 1-/ Y-etylpssu^onyipp.ropylo / -5- / o-trójfluoromety- lófenylo7-7-cl4
Claims (5)
- Zastrzezenia patentowe ' 1. Sposób wytwarzania nowych pochodnych ben- zodwuazepiny o wzorze 1, w którym R! oznacza atom wodoru, atom chlorowca, grupe nitrowa, gru¬ pe cyjanowa, nizszy rodnik alkoksylowy, lub rod¬ nik trójfluorometyIowy, R5 i R6 ozmaczaja niezalez7 nie od siebie atom wodoru, atom chlorowca, niz¬ szy rodnik alkilowy o 1—2 atomach wegla lub rodnik trójfluorometylowy, R4 oznacza rodnik cy- kioalkilowy o 3—6 atomach wegla, rodoik cyklo- alkiloaikilowy, w którym czesc cykloalkilowa za¬ wiera 3—6 atomów wegla, a czesc alkilowa 1—4 atomów wegla, rodnik arylowy lub rodnik aorylo- alkilowy, m jest równe 1 lub 2, a n' jest liczba calkowita 2 lub 3 oraz ich soli, znamienny tym, ze pochodna benzodwuazepiny lub jej sól o wzo¬ rze 2, w którym Ri, R4, R5, Re iii' maja znacze¬ nie podane powyzej a p jest równe zero lufo 1 poddaje sie reakcji ze srodkiem utleniajacym.
- 2. Spos6b wedlug zastrz. 1, znamienny Cym, ze reakcje ze srodkiem utleniajacym prowadzi sie w obecnosci rozpuszczalnika.
- 3. Sposób wedlug zastrz. 1, znamienny tym, ze jako srodek utleniajacy stosuje sie kwas chromo¬ wy, kwas azotowy, nadtlenek wodoru, kwas nad- mrówkowy, kwas nadoctowy, kwas nadbenzoeso- wy, kwas m-nadchlorobenzoesowy, nadsiarczan, dwutlenek selenu, czterooctan olowiu, dwutlenek magnezu lub czterotlpnek rutenu.
- 4. Sposób wedlug zastrz. 2, znamienny tym, ze jako rozpuszczalnik stosuje sie wode, chloroform, czterochlorek wegla, aceton, kwas octowy, kwas mrówkowy, kwas siarkowy, pirydyne, dioksan, benzen, toluen, eter, .octan etylu, metanol lub eta¬ nol.
- 5. Sposób wytwarzania nowych pochodnych ben¬ zodwuazepiny o wzorze 1, w którym Ri oznacza atom wodoru, atom chlorowca, grupe nitrowa, gru¬ pe cyjanowa, nizszy rodnik alkoksylowy, lufo rod¬ nik trójfluorometylowy, R5 i R6 oznaczaja nieza¬ leznie od siebie atom wodoru, atom chlorowca, nizszy rodnik alkilowy o 1—2 atomach wegla lub rodnik trójfluorometylowy, R4 oznacza nizszy rod¬ nik alkilowy o 1—4 atomach wegla, m jest równe 1 lub 2, a n' jest liczba calkowita 1—4, znamienny tym, ze pochodna benzodwuazepiny lub jej sól o wzorze 2, w którym Rlf R4, R5, R9 i n' maja zna¬ czenie podane powyzej, a p jest równe zero lub 1 poddaje sie reakcji ze srodkiem utleniajacym. 10 15 20 23 30 3592569 Ri Ri C=NN N-C :ch, i Cn'H2n' O Wzór 1 C=N \ CH, N-C % O Cn'H2rf S(o).p-R, Wzór 2 Drukarnia Narodowa Zaklad Nr 6, zam. 382/77 Cena 10 zl PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5552970A JPS4831118B1 (pl) | 1970-06-24 | 1970-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL92569B1 true PL92569B1 (pl) | 1977-04-30 |
Family
ID=13001241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL18373771A PL92569B1 (pl) | 1970-06-24 | 1971-02-02 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4831118B1 (pl) |
| AT (1) | AT306733B (pl) |
| CH (1) | CH578545A5 (pl) |
| CS (1) | CS179398B2 (pl) |
| HU (1) | HU163792B (pl) |
| PL (1) | PL92569B1 (pl) |
-
1970
- 1970-06-24 JP JP5552970A patent/JPS4831118B1/ja active Pending
-
1971
- 1971-01-27 HU HUSU000745 patent/HU163792B/hu unknown
- 1971-01-28 AT AT352672A patent/AT306733B/de not_active IP Right Cessation
- 1971-02-01 CS CS426571A patent/CS179398B2/cs unknown
- 1971-02-02 PL PL18373771A patent/PL92569B1/pl unknown
-
1976
- 1976-01-28 CH CH104576A patent/CH578545A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH578545A5 (en) | 1976-08-13 |
| AT306733B (de) | 1973-04-25 |
| HU163792B (pl) | 1973-10-27 |
| CS179398B2 (en) | 1977-10-31 |
| JPS4831118B1 (pl) | 1973-09-26 |
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