DK169722B1 - 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 - Google Patents
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 Download PDFInfo
- Publication number
- DK169722B1 DK169722B1 DK397687A DK397687A DK169722B1 DK 169722 B1 DK169722 B1 DK 169722B1 DK 397687 A DK397687 A DK 397687A DK 397687 A DK397687 A DK 397687A DK 169722 B1 DK169722 B1 DK 169722B1
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- DK
- Denmark
- Prior art keywords
- pyrido
- methyl
- dihydro
- general formula
- group
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 80
- 208000006218 bradycardia Diseases 0.000 title claims abstract description 12
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- 230000036471 bradycardia Effects 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 14
- 206010049765 Bradyarrhythmia Diseases 0.000 title claims description 4
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- -1 1,2- ethylene group Chemical group 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
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- 239000000460 chlorine Substances 0.000 claims abstract description 8
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- 125000000217 alkyl group Chemical group 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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- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005252 haloacyl group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 1
- 229960002329 methacholine Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003149 muscarinic antagonist Substances 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- JECMDTMOQOVPIU-UHFFFAOYSA-N n-(piperidin-2-ylmethyl)-n-propylpropan-1-amine Chemical compound CCCN(CCC)CC1CCCCN1 JECMDTMOQOVPIU-UHFFFAOYSA-N 0.000 description 1
- ZPTBFHQKECXGFX-UHFFFAOYSA-N n-ethyl-n-(piperidin-1-ylmethyl)ethanamine Chemical compound CCN(CC)CN1CCCCC1 ZPTBFHQKECXGFX-UHFFFAOYSA-N 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical group C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 150000003235 pyrrolidines Chemical class 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
- 239000000700 radioactive tracer Substances 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000002460 smooth muscle Anatomy 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
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 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
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- 238000010626 work up procedure 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 | 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 (3)
| Publication Number | Publication Date |
|---|---|
| DK397687D0 DK397687D0 (da) | 1987-07-30 |
| DK397687A DK397687A (da) | 1988-02-01 |
| DK169722B1 true DK169722B1 (da) | 1995-01-23 |
Family
ID=6306503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
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 |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |