DE3409237A1 - Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel - Google Patents
Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelInfo
- Publication number
- DE3409237A1 DE3409237A1 DE19843409237 DE3409237A DE3409237A1 DE 3409237 A1 DE3409237 A1 DE 3409237A1 DE 19843409237 DE19843409237 DE 19843409237 DE 3409237 A DE3409237 A DE 3409237A DE 3409237 A1 DE3409237 A1 DE 3409237A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- deep
- acetyl
- dihydro
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims abstract description 24
- DHZYXWMZLAKTQV-UHFFFAOYSA-N diazepin-3-one Chemical compound O=C1C=CC=CN=N1 DHZYXWMZLAKTQV-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title description 8
- 229940126601 medicinal product Drugs 0.000 title 1
- -1 hydroxyalkyl radical Chemical class 0.000 claims abstract description 162
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 81
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 18
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 7
- 208000006218 bradycardia Diseases 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 63
- 238000009835 boiling Methods 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 28
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- UBRKDAVQCKZSPO-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)-1-piperidinyl]-1-oxoethyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 UBRKDAVQCKZSPO-UHFFFAOYSA-N 0.000 claims description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 8
- 150000003335 secondary amines Chemical class 0.000 claims description 7
- KSSXNHGPIDAUAS-UHFFFAOYSA-N 1,4-benzodiazepin-6-one Chemical compound N1=CC=NC=C2C(=O)C=CC=C21 KSSXNHGPIDAUAS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 5
- HHODBPVGUPPYGP-HBCBNPTOSA-N O[C@@H]1CC[C@H](CC1)N(C)CC1N(CCCC1)CC(=O)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2 Chemical compound O[C@@H]1CC[C@H](CC1)N(C)CC1N(CCCC1)CC(=O)N1C2=C(NC(C3=C1C=CC=C3)=O)C=CC=N2 HHODBPVGUPPYGP-HBCBNPTOSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000005252 haloacyl group Chemical group 0.000 claims description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 3
- VRQOSIAJWZNUSL-UHFFFAOYSA-N 2h-pyrrolo[2,3-i][1,2]benzodiazepin-3-one Chemical class C12=NNC(=O)C=CC2=CC=C2C1=CC=N2 VRQOSIAJWZNUSL-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 230000036471 bradycardia Effects 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 210000002216 heart Anatomy 0.000 abstract description 10
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- 230000002911 mydriatic effect Effects 0.000 abstract description 4
- 230000027119 gastric acid secretion Effects 0.000 abstract description 3
- 206010039424 Salivary hypersecretion Diseases 0.000 abstract description 2
- 208000026451 salivation Diseases 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 abstract 1
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 abstract 1
- 230000001515 vagal effect Effects 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 102
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 59
- 238000002844 melting Methods 0.000 description 54
- 230000008018 melting Effects 0.000 description 54
- 239000013078 crystal Substances 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 46
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- RMBZFWLMYVPNGI-UHFFFAOYSA-N 11-(2-chloroacetyl)-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1NC2=CC=CN=C2N(C(=O)CCl)C2=CC=CC=C21 RMBZFWLMYVPNGI-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- OYGJCGQSFROSHD-UHFFFAOYSA-N 11-(2-chloroacetyl)-5h-benzo[b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC=C2N(C(=O)CCl)C2=CC=CC=C21 OYGJCGQSFROSHD-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- WTIYGHQFUHZRDA-UHFFFAOYSA-N n-ethyl-n-(piperidin-2-ylmethyl)ethanamine Chemical compound CCN(CC)CC1CCCCN1 WTIYGHQFUHZRDA-UHFFFAOYSA-N 0.000 description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- 210000000056 organ Anatomy 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 239000000829 suppository Substances 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- SQMFFRGUTWMNIV-UHFFFAOYSA-N 10-(2-chloroacetyl)-5h-thieno[3,4-b][1,5]benzodiazepin-4-one Chemical compound O=C1NC2=CC=CC=C2N(C(=O)CCl)C2=CSC=C21 SQMFFRGUTWMNIV-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
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- YGJQTYMPKOQMRK-UHFFFAOYSA-N 10-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-1,3-dimethyl-5h-pyrrolo[2,3-c][1,5]benzodiazepin-4-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=CC=CC=C2NC(=O)C2=C1C(C)=CN2C YGJQTYMPKOQMRK-UHFFFAOYSA-N 0.000 description 4
- XMVOGXZDRUZXAP-UHFFFAOYSA-N 2,2,3-trichloropropanenitrile Chemical compound ClCC(Cl)(Cl)C#N XMVOGXZDRUZXAP-UHFFFAOYSA-N 0.000 description 4
- GJJCBYJAVZCDCB-UHFFFAOYSA-N 2-(pyrrolidin-1-ylmethyl)piperidine Chemical compound C1CCCN1CC1CCCCN1 GJJCBYJAVZCDCB-UHFFFAOYSA-N 0.000 description 4
- CTJYUVGVMCELLF-UHFFFAOYSA-N 4-(piperidin-2-ylmethyl)morpholine Chemical compound C1COCCN1CC1CCCCN1 CTJYUVGVMCELLF-UHFFFAOYSA-N 0.000 description 4
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
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- 239000008096 xylene Substances 0.000 description 4
- QYKGBJGIKHJGFR-UHFFFAOYSA-N 1-(piperidin-2-ylmethyl)piperidine Chemical compound C1CCCCN1CC1CCCCN1 QYKGBJGIKHJGFR-UHFFFAOYSA-N 0.000 description 3
- YLBWRMSQRFEIEB-VIFPVBQESA-N 1-[[(2s)-pyrrolidin-2-yl]methyl]pyrrolidine Chemical compound C1CCCN1C[C@@H]1CCCN1 YLBWRMSQRFEIEB-VIFPVBQESA-N 0.000 description 3
- RRULGRNBUCHBHW-UHFFFAOYSA-N 1-chloro-10-[2-[2-[(dimethylamino)methyl]piperidin-1-yl]acetyl]-3-methyl-5h-pyrrolo[2,3-c][1,5]benzodiazepin-4-one Chemical compound CN(C)CC1CCCCN1CC(=O)N1C2=CC=CC=C2NC(=O)C2=C1C(Cl)=CN2C RRULGRNBUCHBHW-UHFFFAOYSA-N 0.000 description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- DXMNQWXQCLWORB-UHFFFAOYSA-N 10-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-3-methyl-5h-pyrrolo[2,3-c][1,5]benzodiazepin-4-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=CC=CC=C2NC(=O)C2=C1C=CN2C DXMNQWXQCLWORB-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
- C07D223/08—Oxygen atoms
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- 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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
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- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Tests Of Electric Status Of Batteries (AREA)
- Electrically Operated Instructional Devices (AREA)
- Toys (AREA)
- Pyrrole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Priority Applications (26)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19843409237 DE3409237A1 (de) | 1984-03-14 | 1984-03-14 | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
ZA851871A ZA851871B (en) | 1984-03-14 | 1985-01-13 | Condensed diazepinones processes for preparing them and pharmaceutical compositions containing these compounds |
AT85102387T ATE44744T1 (de) | 1984-03-14 | 1985-03-04 | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. |
EP85102387A EP0156191B1 (de) | 1984-03-14 | 1985-03-04 | Kondensierte Diazepinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
DE8585102387T DE3571620D1 (en) | 1984-03-14 | 1985-03-04 | Condensed diazepinones, process for their preparation and medicaments containing these compounds |
PH31947A PH21031A (en) | 1984-03-14 | 1985-03-06 | Condensed diazepinones, pharmaceutical composition containing same and method of using said compound |
GR850612A GR850612B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-03-14 | 1985-03-11 | |
DD85274054A DD235260A5 (de) | 1984-03-14 | 1985-03-12 | Verfahren zur herstellung neuer kondensierter diazepinone |
IL74573A IL74573A (en) | 1984-03-14 | 1985-03-12 | ((aminoalkyl)cyclic amino)alkanoyl-condensed benzodiazepinones,their preparation and pharmaceutical compositions containing them |
AU39815/85A AU571315B2 (en) | 1984-03-14 | 1985-03-13 | Diazepinone derivatives |
CA000476368A CA1244016A (en) | 1984-03-14 | 1985-03-13 | Condensed diazepinones, processes for preparing them and pharmaceutical compositions containing these compounds |
NO850992A NO161371C (no) | 1984-03-14 | 1985-03-13 | Analogifremgangsmaate for fremstilling av terapeutisk aktive diazepinon-derivater. |
DK114985A DK171023B1 (da) | 1984-03-14 | 1985-03-13 | Basisk substituerede tricykliske diazepinoner, fremgangsmåde til deres fremstilling og lægemiddel indeholdende sådanne forbindelser |
JP60050229A JPS60215683A (ja) | 1984-03-14 | 1985-03-13 | 新規縮合ジアゼピノン |
ES541212A ES8607282A1 (es) | 1984-03-14 | 1985-03-13 | Procedimiento de preparar nuevas diazepinonas condensadas |
IE64585A IE58237B1 (en) | 1984-03-14 | 1985-03-13 | Condensed diazepinones, processes for preparing them and pharmaceutical compositions containing these compounds |
PT80097A PT80097B (pt) | 1984-03-14 | 1985-03-13 | Processo para a preparacao de diazepinonas condensadas e de composicoes farmaceuticas contendo estes compostos |
FI850991A FI81342C (fi) | 1984-03-14 | 1985-03-13 | Foerfarande foer framstaellning av farmaceutiskt vaerdefulla basiskt substituerade tricykliska diazepinoner. |
HU85939A HU192272B (en) | 1984-03-14 | 1985-03-13 | Process for production of condensated diasepinons |
NZ211425A NZ211425A (en) | 1984-03-14 | 1985-03-13 | Diazepines and pharmaceutical compositions |
US06/711,913 US4550107A (en) | 1984-03-14 | 1985-03-14 | Condensed diazepinones, their compositions and methods of use as pharmaceuticals |
KR1019850001629A KR920003980B1 (ko) | 1984-03-14 | 1985-03-14 | 축합 디아제핀온의 제조방법 |
ES551277A ES8702908A1 (es) | 1984-03-14 | 1986-01-27 | Procedimiento de preparar nuevas diazepinonas condensadas |
ES551276A ES8701750A1 (es) | 1984-03-14 | 1986-01-27 | Procedimiento de preparar nuevas diazepinonas condensadas |
CS914096A CS409691A3 (en) | 1984-03-14 | 1991-12-27 | Condensed diazepinones, process of their preparation and pharmaceuticalcompositions containing them |
MX9202791A MX9202791A (es) | 1984-03-14 | 1992-06-11 | Diazepinonas condesadas y procedimiento para su preparacion. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19843409237 DE3409237A1 (de) | 1984-03-14 | 1984-03-14 | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
Publication Number | Publication Date |
---|---|
DE3409237A1 true DE3409237A1 (de) | 1985-09-19 |
Family
ID=6230402
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19843409237 Withdrawn DE3409237A1 (de) | 1984-03-14 | 1984-03-14 | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DE8585102387T Expired DE3571620D1 (en) | 1984-03-14 | 1985-03-04 | Condensed diazepinones, process for their preparation and medicaments containing these compounds |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE8585102387T Expired DE3571620D1 (en) | 1984-03-14 | 1985-03-04 | Condensed diazepinones, process for their preparation and medicaments containing these compounds |
Country Status (23)
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0333315A1 (en) * | 1988-02-12 | 1989-09-20 | Dr. Lo. Zambeletti S.p.A. | Azacyclic compounds, processes for their preparation and their pharmaceutical use |
EP0411567A1 (de) * | 1989-07-31 | 1991-02-06 | ARZNEIMITTELWERK DRESDEN GmbH | Neue 5-(omega-Aminoacyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]-diazepin-11-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
WO1991017116A1 (en) * | 1990-04-28 | 1991-11-14 | Dr. Lo. Zambeletti S.P.A. | Novel 1-(2h-1-oxo-3,4-dihydronaphtyl-6)-acetyl-piperidines, process for their preparation and therapeutic use |
EP0515796A1 (de) * | 1991-05-25 | 1992-12-02 | ARZNEIMITTELWERK DRESDEN GmbH | Neue 5-Aminoacyl-5.10-dihydro-11H-dibenzo/b,e/1,4/diazepin-11-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3683217D1 (de) * | 1985-06-27 | 1992-02-13 | Thomae Gmbh Dr K | In 11-stellung substituierte 5,11-dihydro-6h-pyrido-(2,3-b)(1,4)benzodiazepin-6-one, verfahren zur ihrer herstellung und diese verbindungen enthaltende arzneimittel. |
DE3529372A1 (de) * | 1985-08-16 | 1987-02-19 | Dompe Farmaceutici Spa | Aminoacyl-derivat von 4,9-dihydro-10h-pyrido(3,2-b)-thieno(3,2-e) (1,4)-diazepinon und von 4,9-dihydro-10h-pyrido(3,2-b)thieno(3,4-e) (1,4)diazepinon, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen |
DE3531682A1 (de) * | 1985-09-05 | 1987-03-12 | Thomae Gmbh Dr K | (+)-6-chlor-5,10-dihydro-5-((1-methyl-4- piperidinyl)acetyl)-11h-dibenzo(b,e)(1,4) diazepin-11-on, seine isolierung und verwendung als arzneimittel |
JPS62107216A (ja) * | 1985-11-05 | 1987-05-18 | Ngk Insulators Ltd | バルブシートインサート及びその製造法並びにそれを使用してなるシリンダーヘッド |
DE3626095A1 (de) * | 1986-07-31 | 1988-02-11 | Thomae Gmbh Dr K | Neue substituierte pyrido(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DE3643666A1 (de) * | 1986-12-20 | 1988-06-30 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DE3726908A1 (de) * | 1987-08-13 | 1989-02-23 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DE3735895A1 (de) * | 1987-10-23 | 1989-05-03 | Thomae Gmbh Dr K | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DE3802334A1 (de) * | 1988-01-27 | 1989-08-10 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DE3819444A1 (de) * | 1988-06-08 | 1989-12-14 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DE3820347A1 (de) * | 1988-06-15 | 1989-12-21 | Thomae Gmbh Dr K | Verwendung von in 11-stellung substituierten 5,11-dihydro-6h-pyrido(2,3-b) (1,4)benzodiazepin-6-onen zur behandlung von bradycardien und bradyarrhythmien in der human- und veterinaermedizin |
US4931436A (en) * | 1988-08-09 | 1990-06-05 | Dr. Karl Thomae Gmbh | Condensed diazepinones, processes for preparing them and pharmaceutical compositions containing these compounds |
US5179090A (en) * | 1989-09-11 | 1993-01-12 | Klaus Rudolf | Condensed diazepinones and medicaments containing these compounds |
DE4112014A1 (de) * | 1991-04-12 | 1992-10-15 | Thomae Gmbh Dr K | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel zur behandlung von erkrankungen des zentralnervensystems und zur foerderung der cerebralen durchblutung |
US5324832A (en) * | 1991-07-03 | 1994-06-28 | The United States Of America As Represented By The Department Of Health And Human Services | Muscarinic antagonists |
US5716952A (en) * | 1992-03-18 | 1998-02-10 | Allergan | Method for reducing intraocular pressure in the mammalian eye by administration of muscarinic antagonists |
WO2023190663A1 (ja) | 2022-03-30 | 2023-10-05 | 参天製薬株式会社 | 高純度化合物の製造方法および精製方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1795183B1 (de) * | 1968-08-20 | 1972-07-20 | Thomae Gmbh Dr K | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate und Arzneimittel |
IL62792A (en) * | 1980-05-07 | 1985-02-28 | Byk Gulden Lomberg Chem Fab | Acylated dihydrothienodiazepinone compounds,process for their preparation,and medicaments containing them |
DE3028001A1 (de) * | 1980-07-24 | 1982-02-18 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue, in 5-stellung substituierte 5,10-dihydro-11h-dibenzo (b,e)(1,4) diazepin-11-one, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel |
DE3262922D1 (en) * | 1981-02-02 | 1985-05-15 | Byk Gulden Lomberg Chem Fab | Tricyclic pyrrols, process for their preparation, their use and compositions containing them |
DE3204153A1 (de) * | 1982-02-06 | 1983-08-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Substituierte thienobenzodiazepinone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
DE3204158A1 (de) * | 1982-02-06 | 1983-08-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | "substituierte dibenzodiazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel" |
EP0086591A1 (en) * | 1982-02-10 | 1983-08-24 | George Patrick Allnutt | Apparatus for dispensing particulate materials |
US4558132A (en) * | 1982-07-02 | 1985-12-10 | A. H. Robins Company, Incorporated | Nitro, amino and aroylamino-N-phenylpyridinamines in a process for preparing pyrido[1,4]benzodiazepines |
IT1212742B (it) * | 1983-05-17 | 1989-11-30 | Dompe Farmaceutici Spa | Derivati dibenzo [1,4]diazepinonici pirido [1,4] benzodiazepinonici,pirido [1,5] benzodiazepinonici e loro attivita' farmacologica |
-
1984
- 1984-03-14 DE DE19843409237 patent/DE3409237A1/de not_active Withdrawn
-
1985
- 1985-01-13 ZA ZA851871A patent/ZA851871B/xx unknown
- 1985-03-04 DE DE8585102387T patent/DE3571620D1/de not_active Expired
- 1985-03-04 AT AT85102387T patent/ATE44744T1/de not_active IP Right Cessation
- 1985-03-04 EP EP85102387A patent/EP0156191B1/de not_active Expired
- 1985-03-06 PH PH31947A patent/PH21031A/en unknown
- 1985-03-11 GR GR850612A patent/GR850612B/el unknown
- 1985-03-12 IL IL74573A patent/IL74573A/xx not_active IP Right Cessation
- 1985-03-12 DD DD85274054A patent/DD235260A5/de not_active IP Right Cessation
- 1985-03-13 JP JP60050229A patent/JPS60215683A/ja active Granted
- 1985-03-13 AU AU39815/85A patent/AU571315B2/en not_active Ceased
- 1985-03-13 CA CA000476368A patent/CA1244016A/en not_active Expired
- 1985-03-13 NZ NZ211425A patent/NZ211425A/en unknown
- 1985-03-13 NO NO850992A patent/NO161371C/no unknown
- 1985-03-13 FI FI850991A patent/FI81342C/fi not_active IP Right Cessation
- 1985-03-13 HU HU85939A patent/HU192272B/hu not_active IP Right Cessation
- 1985-03-13 DK DK114985A patent/DK171023B1/da not_active IP Right Cessation
- 1985-03-13 PT PT80097A patent/PT80097B/pt not_active IP Right Cessation
- 1985-03-13 ES ES541212A patent/ES8607282A1/es not_active Expired
- 1985-03-13 IE IE64585A patent/IE58237B1/en not_active IP Right Cessation
- 1985-03-14 US US06/711,913 patent/US4550107A/en not_active Expired - Lifetime
- 1985-03-14 KR KR1019850001629A patent/KR920003980B1/ko not_active Expired
-
1986
- 1986-01-27 ES ES551276A patent/ES8701750A1/es not_active Expired
- 1986-01-27 ES ES551277A patent/ES8702908A1/es not_active Expired
-
1991
- 1991-12-27 CS CS914096A patent/CS409691A3/cs unknown
-
1992
- 1992-06-11 MX MX9202791A patent/MX9202791A/es unknown
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0333315A1 (en) * | 1988-02-12 | 1989-09-20 | Dr. Lo. Zambeletti S.p.A. | Azacyclic compounds, processes for their preparation and their pharmaceutical use |
EP0411567A1 (de) * | 1989-07-31 | 1991-02-06 | ARZNEIMITTELWERK DRESDEN GmbH | Neue 5-(omega-Aminoacyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]-diazepin-11-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
WO1991017116A1 (en) * | 1990-04-28 | 1991-11-14 | Dr. Lo. Zambeletti S.P.A. | Novel 1-(2h-1-oxo-3,4-dihydronaphtyl-6)-acetyl-piperidines, process for their preparation and therapeutic use |
US5428042A (en) * | 1990-04-28 | 1995-06-27 | Dr Lo Zambeletti S.P.A. | 1-(2H-1-oxo-3,4-dihydronaphtyl-6-yl)-acetyl-piperidines as kappa agonists |
EP0515796A1 (de) * | 1991-05-25 | 1992-12-02 | ARZNEIMITTELWERK DRESDEN GmbH | Neue 5-Aminoacyl-5.10-dihydro-11H-dibenzo/b,e/1,4/diazepin-11-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
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