NO890293L - Analogifremgangsmaate for fremstilling av terapeutisk aktive dibenzo- og pyridobenzo-azepinon-derivater. - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive dibenzo- og pyridobenzo-azepinon-derivater.Info
- Publication number
- NO890293L NO890293L NO89890293A NO890293A NO890293L NO 890293 L NO890293 L NO 890293L NO 89890293 A NO89890293 A NO 89890293A NO 890293 A NO890293 A NO 890293A NO 890293 L NO890293 L NO 890293L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- dihydro
- piperidinyl
- carbonyl
- dibenz
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 30
- 238000002360 preparation method Methods 0.000 title claims description 12
- PCYKWFJOWLMXRT-UHFFFAOYSA-N pyrido[2,3-i][1]benzazepin-2-one Chemical class O=C1C=CC=C2C=CC3=NC=CC=C3C2=N1 PCYKWFJOWLMXRT-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 85
- 239000000460 chlorine Substances 0.000 claims description 74
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- -1 2-chloro-6,11-dihydro-11-[(1-methyl-4-piperidinyl)-carbonyl]-5H-pyrido[2,3-b]-benzazepine -6-on Chemical compound 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- IBGGTRIVSSWMCS-UHFFFAOYSA-N 1-fluoro-11-(1-methylpiperidine-4-carbonyl)-5,11-dihydrobenzo[c][1]benzazepin-6-one Chemical compound C1CN(C)CCC1C(=O)C1C2=C(F)C=CC=C2NC(=O)C2=CC=CC=C21 IBGGTRIVSSWMCS-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- JTNYLLAZCRMXBN-UHFFFAOYSA-N 11-(1-methylpiperidine-4-carbonyl)-5,11-dihydrobenzo[c][1]benzazepin-6-one Chemical compound C1CN(C)CCC1C(=O)C1C2=CC=CC=C2C(=O)NC2=CC=CC=C21 JTNYLLAZCRMXBN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000002900 organolithium compounds Chemical class 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims 1
- 159000000002 lithium salts Chemical class 0.000 claims 1
- 238000004458 analytical method Methods 0.000 description 67
- 239000000203 mixture Substances 0.000 description 52
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- 238000002844 melting Methods 0.000 description 16
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
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- 239000002904 solvent Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
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- 238000006243 chemical reaction Methods 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 229960004633 pirenzepine Drugs 0.000 description 8
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- 125000005843 halogen 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
- 229960001340 histamine Drugs 0.000 description 1
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- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- AYLUKTKPNDSZBS-UHFFFAOYSA-N methyl 1-ethylpiperidine-4-carboxylate Chemical compound CCN1CCC(C(=O)OC)CC1 AYLUKTKPNDSZBS-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- PXIVVJDSBGBMPZ-UHFFFAOYSA-N n-[2-[(2-fluorophenyl)methyl]phenyl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=CC=C1CC1=CC=CC=C1F PXIVVJDSBGBMPZ-UHFFFAOYSA-N 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- 230000024717 negative regulation of secretion Effects 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8819192A IT8819192A0 (it) | 1988-01-25 | 1988-01-25 | Amminochetoni di dibenzo e piridobenzo azepinoni sostituiti e composizioni farmaceutiche. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO890293D0 NO890293D0 (no) | 1989-01-24 |
| NO890293L true NO890293L (no) | 1989-07-26 |
Family
ID=11155667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO89890293A NO890293L (no) | 1988-01-25 | 1989-01-24 | Analogifremgangsmaate for fremstilling av terapeutisk aktive dibenzo- og pyridobenzo-azepinon-derivater. |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0326526A1 (it) |
| JP (1) | JPH01216989A (it) |
| KR (1) | KR890011885A (it) |
| AU (1) | AU2880089A (it) |
| DD (1) | DD283387A5 (it) |
| DK (1) | DK29489A (it) |
| FI (1) | FI890324A (it) |
| HU (1) | HU199452B (it) |
| IL (1) | IL89061A0 (it) |
| IT (1) | IT8819192A0 (it) |
| NO (1) | NO890293L (it) |
| PL (1) | PL277329A1 (it) |
| PT (1) | PT89519B (it) |
| YU (1) | YU16389A (it) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100486316B1 (ko) * | 2002-07-06 | 2005-04-29 | 일동제약주식회사 | 5,11-디히드로-6에이치-디벤즈[비,이]아제핀-6-온의새로운 제조방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3402060A1 (de) * | 1984-01-21 | 1985-08-01 | Dr. Karl Thomae Gmbh, 7950 Biberach | Substituierte 5,11-dihydro-6h-dibenz(b,e)azepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
-
1988
- 1988-01-25 IT IT8819192A patent/IT8819192A0/it unknown
-
1989
- 1989-01-23 DD DD89325189A patent/DD283387A5/de not_active IP Right Cessation
- 1989-01-23 PL PL27732989A patent/PL277329A1/xx unknown
- 1989-01-23 KR KR1019890000676A patent/KR890011885A/ko not_active Application Discontinuation
- 1989-01-23 FI FI890324A patent/FI890324A/fi not_active Application Discontinuation
- 1989-01-24 DK DK029489A patent/DK29489A/da not_active Application Discontinuation
- 1989-01-24 YU YU00163/89A patent/YU16389A/xx unknown
- 1989-01-24 PT PT89519A patent/PT89519B/pt active IP Right Grant
- 1989-01-24 IL IL89061A patent/IL89061A0/xx unknown
- 1989-01-24 EP EP89830023A patent/EP0326526A1/en not_active Withdrawn
- 1989-01-24 HU HU89296A patent/HU199452B/hu not_active IP Right Cessation
- 1989-01-24 JP JP1014942A patent/JPH01216989A/ja active Pending
- 1989-01-24 NO NO89890293A patent/NO890293L/no unknown
- 1989-01-25 AU AU28800/89A patent/AU2880089A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| FI890324A (fi) | 1989-07-26 |
| HUT49130A (en) | 1989-08-28 |
| DK29489A (da) | 1989-07-26 |
| KR890011885A (ko) | 1989-08-23 |
| DD283387A5 (de) | 1990-10-10 |
| PT89519B (pt) | 1994-02-28 |
| NO890293D0 (no) | 1989-01-24 |
| IL89061A0 (en) | 1989-08-15 |
| YU16389A (en) | 1991-10-31 |
| DK29489D0 (da) | 1989-01-24 |
| PL277329A1 (en) | 1989-09-18 |
| JPH01216989A (ja) | 1989-08-30 |
| IT8819192A0 (it) | 1988-01-25 |
| FI890324A0 (fi) | 1989-01-23 |
| AU2880089A (en) | 1989-07-27 |
| HU199452B (en) | 1990-02-28 |
| EP0326526A1 (en) | 1989-08-02 |
| PT89519A (pt) | 1989-10-04 |
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