AU594489B2 - Substituted pyrido(2,3-b)(1,4) Benzodiazepin-6-ones - Google Patents
Substituted pyrido(2,3-b)(1,4) Benzodiazepin-6-ones Download PDFInfo
- Publication number
- AU594489B2 AU594489B2 AU76350/87A AU7635087A AU594489B2 AU 594489 B2 AU594489 B2 AU 594489B2 AU 76350/87 A AU76350/87 A AU 76350/87A AU 7635087 A AU7635087 A AU 7635087A AU 594489 B2 AU594489 B2 AU 594489B2
- Authority
- AU
- Australia
- Prior art keywords
- formula
- group
- methyl
- pyrido
- dihydro
- 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.)
- Ceased
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- 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 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 53
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 208000006218 bradycardia Diseases 0.000 claims abstract description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 14
- -1 1,2- ethylene group Chemical group 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
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- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
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- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical class N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 210000001138 tear Anatomy 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3626095.9 | 1986-07-31 | ||
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| AU7635087A AU7635087A (en) | 1988-02-04 |
| AU594489B2 true AU594489B2 (en) | 1990-03-08 |
Family
ID=6306503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU76350/87A Ceased AU594489B2 (en) | 1986-07-31 | 1987-07-31 | Substituted pyrido(2,3-b)(1,4) Benzodiazepin-6-ones |
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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1123283A (en) * | 1982-02-09 | 1983-08-18 | Thomae, Karl G.M.B.H. | Pyridobenzodiazepinone derivatives |
| AU9163382A (en) * | 1982-07-02 | 1984-01-05 | A.H. Robins Company, Incorporated | N-phenylpyridinamines and pyrido(1,4)-benzodiazepines |
| AU571315B2 (en) * | 1984-03-14 | 1988-04-14 | Dr. Karl Thomae Gmbh | Diazepinone derivatives |
Family Cites Families (2)
| 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 |
-
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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1123283A (en) * | 1982-02-09 | 1983-08-18 | Thomae, Karl G.M.B.H. | Pyridobenzodiazepinone derivatives |
| AU9163382A (en) * | 1982-07-02 | 1984-01-05 | A.H. Robins Company, Incorporated | N-phenylpyridinamines and pyrido(1,4)-benzodiazepines |
| AU571315B2 (en) * | 1984-03-14 | 1988-04-14 | Dr. Karl Thomae Gmbh | Diazepinone derivatives |
Also Published As
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