DE3626095A1 - Neue substituierte pyrido(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel - Google Patents
Neue substituierte pyrido(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelInfo
- Publication number
- DE3626095A1 DE3626095A1 DE19863626095 DE3626095A DE3626095A1 DE 3626095 A1 DE3626095 A1 DE 3626095A1 DE 19863626095 DE19863626095 DE 19863626095 DE 3626095 A DE3626095 A DE 3626095A DE 3626095 A1 DE3626095 A1 DE 3626095A1
- Authority
- DE
- Germany
- Prior art keywords
- benzodiazepin
- pyrido
- group
- methyl
- atom
- 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- Withdrawn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 31
- QYETZOYLEWPRIX-UHFFFAOYSA-N pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical class O=C1N=C2C=CC=NC2=NC2=CC=CC=C12 QYETZOYLEWPRIX-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 8
- 229940126601 medicinal product Drugs 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- -1 1,2- ethylene group Chemical group 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 9
- 150000007524 organic acids Chemical class 0.000 claims abstract description 9
- 235000005985 organic acids Nutrition 0.000 claims abstract description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 208000006218 bradycardia Diseases 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000036471 bradycardia Effects 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- 239000011737 fluorine Substances 0.000 claims abstract description 4
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- PGBFOEXPMAAGPS-UHFFFAOYSA-N 9-chloro-11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(Cl)C=C21 PGBFOEXPMAAGPS-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000012442 inert solvent Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000005252 haloacyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- LZZHZDKCHWMXTK-UHFFFAOYSA-N pyrido[2,3-i][1,4]benzodiazepin-6-one Chemical class N1=CC=NC=C2C1=C1C(=CC2=O)N=CC=C1 LZZHZDKCHWMXTK-UHFFFAOYSA-N 0.000 claims 1
- 210000002216 heart Anatomy 0.000 abstract description 14
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 230000001515 vagal effect Effects 0.000 abstract description 4
- 230000002349 favourable effect Effects 0.000 abstract description 3
- 206010039424 Salivary hypersecretion Diseases 0.000 abstract description 2
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 230000002911 mydriatic effect Effects 0.000 abstract description 2
- 208000026451 salivation Diseases 0.000 abstract description 2
- 210000004211 gastric acid Anatomy 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 23
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 22
- 239000000126 substance Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 210000000056 organ Anatomy 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 230000001965 increasing effect Effects 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 239000000829 suppository Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000027455 binding Effects 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 210000003296 saliva Anatomy 0.000 description 6
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 5
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
- 238000010494 dissociation reaction Methods 0.000 description 5
- 230000005593 dissociations Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- WTIYGHQFUHZRDA-UHFFFAOYSA-N n-ethyl-n-(piperidin-2-ylmethyl)ethanamine Chemical compound CCN(CC)CC1CCCCN1 WTIYGHQFUHZRDA-UHFFFAOYSA-N 0.000 description 5
- 230000028327 secretion Effects 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
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- 150000001412 amines Chemical class 0.000 description 4
- 230000001022 anti-muscarinic effect Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- DHZYXWMZLAKTQV-UHFFFAOYSA-N diazepin-3-one Chemical class O=C1C=CC=CN=N1 DHZYXWMZLAKTQV-UHFFFAOYSA-N 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 239000007858 starting material Substances 0.000 description 4
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- UZEBJLIOUJPVCE-UHFFFAOYSA-N 9-chloro-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C2=NC=CC=C2NC(=O)C2=CC=C(Cl)C=C12 UZEBJLIOUJPVCE-UHFFFAOYSA-N 0.000 description 3
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- HGWUGHJZLKPTHL-UHFFFAOYSA-N n-ethyl-n-(morpholin-3-ylmethyl)ethanamine Chemical compound CCN(CC)CC1COCCN1 HGWUGHJZLKPTHL-UHFFFAOYSA-N 0.000 description 1
- HOIFYAYAOLSLBR-UHFFFAOYSA-N n-ethyl-n-(pyrrolidin-3-ylmethyl)ethanamine Chemical compound CCN(CC)CC1CCNC1 HOIFYAYAOLSLBR-UHFFFAOYSA-N 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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Classifications
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Lubricants (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863626095 DE3626095A1 (de) | 1986-07-31 | 1986-07-31 | Neue substituierte pyrido(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| PH35517A PH26406A (en) | 1986-07-31 | 1987-07-09 | Substituted pyrido (2,3-b) (1-4) benzodiazepin-6-ones and medicaments containing these compounds |
| JP62175802A JP2519734B2 (ja) | 1986-07-31 | 1987-07-14 | 新規置換ピリド〔２，３−ｂ〕〔１，４〕ベンゾジアゼピン−６−オン，その製法及びその化合物を含む医薬 |
| ES87110190T ES2042523T3 (es) | 1986-07-31 | 1987-07-15 | Procedimiento para la preparacion de pirido-(2,3-b)(1,4)-benzodiazepin-6-onas. |
| DE8787110190T DE3779369D1 (de) | 1986-07-31 | 1987-07-15 | Substituierte pyrido-(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. |
| EP87110190A EP0254955B1 (de) | 1986-07-31 | 1987-07-15 | Substituierte Pyrido-[2,3-b][1,4]benzodiazepin-6-one, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| AT87110190T ATE76643T1 (de) | 1986-07-31 | 1987-07-15 | Substituierte pyrido-(2,3-b>(1,4>benzodiazepin-6- one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. |
| FI873297A FI85479C (fi) | 1986-07-31 | 1987-07-29 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla substituerade 11-//2-/(dietylamino) metyl/-1 -piperidinyl/-asetyl/5,11-dihydro-6h-pyrido/2,3-b//1,4/-bensodiazepin-6 -oner. |
| DD87305486A DD265146A5 (de) | 1986-07-31 | 1987-07-29 | Verfahren zur herstellung von neuen substituierten 6 h-pyrido [2,3-b] [1,4]benzodiazepin-6-onen |
| IL83366A IL83366A (en) | 1986-07-31 | 1987-07-29 | 11-(amino-or aminomethyl-cyclic-aminoacetyl)-5,11-dihydro(2,3-b)(1,4)benzodiazepin-6-ones,their preparation and pharmaceutical compositions containing them |
| CA000543258A CA1311752C (en) | 1986-07-31 | 1987-07-29 | Substituted pyrido (2,3-b)(1,4)benzodiazepin-6-ones, processes for theirpreparation and medicaments containing these compounds |
| IE206287A IE60861B1 (en) | 1986-07-31 | 1987-07-30 | New substituted pyrido(2,3-b)(1,4)benzodiazepin-6-ones, processes for their preparation and medicaments containing these compounds |
| NO873189A NO165345C (no) | 1986-07-31 | 1987-07-30 | Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrido (2,3-b)(1,4)benzodiazepin-6-on-derivater. |
| PT85455A PT85455B (pt) | 1986-07-31 | 1987-07-30 | Processo para a preparacao de novas pirido{2,3-b}{1,4}-benzodiazepino-6-onas substituidas e de composicoes farmaceuticas que as contem |
| DK397687A DK169722B1 (da) | 1986-07-31 | 1987-07-30 | Substituerede pyrido [2,3-b][1,4]benzodiazepin-6-oner, lægemidler med indhold af forbindelserne, forbindelserne til anvendelse ved behandling af bradycardi og bradyarrhytmi samt fremgangsmåde til fremstilling af forbindelserne |
| ZA875623A ZA875623B (en) | 1986-07-31 | 1987-07-30 | Substituted pyrido(2,3-b)(1,4)benzodiazepin-6-ones |
| NZ221278A NZ221278A (en) | 1986-07-31 | 1987-07-30 | Substituted pyrido(2,3-b)(1,4)benzodiazepin-6-ones and pharmaceutical compositions |
| HU873522A HU197745B (en) | 1986-07-31 | 1987-07-30 | Process for producing pyrido/2,3-b//1,4/benzodiazepinon derivatives and pharmaceutical compositions containing them as active components |
| AU76350/87A AU594489B2 (en) | 1986-07-31 | 1987-07-31 | Substituted pyrido(2,3-b)(1,4) Benzodiazepin-6-ones |
| KR1019870008387A KR950010073B1 (ko) | 1986-07-31 | 1987-07-31 | 치환된 피리도[2,3-b][1,4]벤조디아제핀-6-온, 이의 제조방법 및 이를 함유하는 약제 |
| US07/080,716 US4971966A (en) | 1986-07-31 | 1987-07-31 | Substituted pyrido(2,3-B) (1,4) benzodiazepin-6-ones, and medicaments containing these compounds |
| GR920401502T GR3005157T3 (enExample) | 1986-07-31 | 1992-07-13 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863626095 DE3626095A1 (de) | 1986-07-31 | 1986-07-31 | Neue substituierte pyrido(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3626095A1 true DE3626095A1 (de) | 1988-02-11 |
Family
ID=6306503
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863626095 Withdrawn DE3626095A1 (de) | 1986-07-31 | 1986-07-31 | Neue substituierte pyrido(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE8787110190T Expired - Lifetime DE3779369D1 (de) | 1986-07-31 | 1987-07-15 | Substituierte pyrido-(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8787110190T Expired - Lifetime DE3779369D1 (de) | 1986-07-31 | 1987-07-15 | Substituierte pyrido-(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4971966A (enExample) |
| EP (1) | EP0254955B1 (enExample) |
| JP (1) | JP2519734B2 (enExample) |
| KR (1) | KR950010073B1 (enExample) |
| AT (1) | ATE76643T1 (enExample) |
| AU (1) | AU594489B2 (enExample) |
| CA (1) | CA1311752C (enExample) |
| DD (1) | DD265146A5 (enExample) |
| DE (2) | DE3626095A1 (enExample) |
| DK (1) | DK169722B1 (enExample) |
| ES (1) | ES2042523T3 (enExample) |
| FI (1) | FI85479C (enExample) |
| GR (1) | GR3005157T3 (enExample) |
| HU (1) | HU197745B (enExample) |
| IE (1) | IE60861B1 (enExample) |
| IL (1) | IL83366A (enExample) |
| NO (1) | NO165345C (enExample) |
| NZ (1) | NZ221278A (enExample) |
| PH (1) | PH26406A (enExample) |
| PT (1) | PT85455B (enExample) |
| ZA (1) | ZA875623B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3726908A1 (de) * | 1987-08-13 | 1989-02-23 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3820346A1 (de) * | 1988-06-15 | 1989-12-21 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5179090A (en) * | 1989-09-11 | 1993-01-12 | Klaus Rudolf | Condensed diazepinones and medicaments containing these compounds |
| 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 |
| US6531502B1 (en) * | 1998-01-21 | 2003-03-11 | Sugen, Inc. | 3-Methylidenyl-2-indolinone modulators of protein kinase |
| CN1241833C (zh) | 2000-10-20 | 2006-02-15 | 昭和电工株式会社 | 生产低碱氧化铝的方法及其设备 |
| GB0428250D0 (en) * | 2004-12-23 | 2005-01-26 | Novartis Ag | Organic compounds |
| JP2007051037A (ja) * | 2005-08-19 | 2007-03-01 | Asahi Kagaku Kogyo Co Ltd | 薄片状αアルミナ粒子の製造方法 |
| JPWO2023190663A1 (enExample) * | 2022-03-30 | 2023-10-05 |
Family Cites Families (5)
| 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 |
| US4210648A (en) * | 1977-05-31 | 1980-07-01 | Boehringer Ingelheim Gmbh | II-Aminoacyl-5,11-dihydro-6H-pyrido(2,3-B) (1,4)benzodiazepin-6-ones and salts thereof |
| DE3204403A1 (de) * | 1982-02-09 | 1983-08-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| 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 |
| DE3409237A1 (de) * | 1984-03-14 | 1985-09-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
-
1986
- 1986-07-31 DE DE19863626095 patent/DE3626095A1/de not_active Withdrawn
-
1987
- 1987-07-09 PH PH35517A patent/PH26406A/en unknown
- 1987-07-14 JP JP62175802A patent/JP2519734B2/ja not_active Expired - Lifetime
- 1987-07-15 DE DE8787110190T patent/DE3779369D1/de not_active Expired - Lifetime
- 1987-07-15 AT AT87110190T patent/ATE76643T1/de not_active IP Right Cessation
- 1987-07-15 EP EP87110190A patent/EP0254955B1/de not_active Expired - Lifetime
- 1987-07-15 ES ES87110190T patent/ES2042523T3/es not_active Expired - Lifetime
- 1987-07-29 IL IL83366A patent/IL83366A/xx unknown
- 1987-07-29 DD DD87305486A patent/DD265146A5/de not_active IP Right Cessation
- 1987-07-29 FI FI873297A patent/FI85479C/fi not_active IP Right Cessation
- 1987-07-29 CA CA000543258A patent/CA1311752C/en not_active Expired - Lifetime
- 1987-07-30 HU HU873522A patent/HU197745B/hu not_active IP Right Cessation
- 1987-07-30 NO NO873189A patent/NO165345C/no unknown
- 1987-07-30 NZ NZ221278A patent/NZ221278A/xx unknown
- 1987-07-30 IE IE206287A patent/IE60861B1/en not_active IP Right Cessation
- 1987-07-30 DK DK397687A patent/DK169722B1/da not_active IP Right Cessation
- 1987-07-30 ZA ZA875623A patent/ZA875623B/xx unknown
- 1987-07-30 PT PT85455A patent/PT85455B/pt not_active IP Right Cessation
- 1987-07-31 AU AU76350/87A patent/AU594489B2/en not_active Ceased
- 1987-07-31 KR KR1019870008387A patent/KR950010073B1/ko not_active Expired - Fee Related
- 1987-07-31 US US07/080,716 patent/US4971966A/en not_active Expired - Fee Related
-
1992
- 1992-07-13 GR GR920401502T patent/GR3005157T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |