ES261027A1 - Substituted 5h-dibenz[b,f]azepines and their 10,11-dihydro derivatives - Google Patents
Substituted 5h-dibenz[b,f]azepines and their 10,11-dihydro derivativesInfo
- Publication number
- ES261027A1 ES261027A1 ES0261027A ES261027A ES261027A1 ES 261027 A1 ES261027 A1 ES 261027A1 ES 0261027 A ES0261027 A ES 0261027A ES 261027 A ES261027 A ES 261027A ES 261027 A1 ES261027 A1 ES 261027A1
- Authority
- ES
- Spain
- Prior art keywords
- general formula
- reaction
- compounds
- compound
- prepared
- 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.)
- Expired
Links
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical class C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 7
- 150000002148 esters Chemical class 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 abstract 2
- 238000006722 reduction reaction Methods 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- -1 aliphatic oxo compound Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- 230000002082 anti-convulsion Effects 0.000 abstract 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 239000000812 cholinergic antagonist Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 150000003949 imides Chemical class 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- 150000003385 sodium Chemical class 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 230000002048 spasmolytic effect Effects 0.000 abstract 1
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
- C07D401/12—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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of general formula <FORM:0908788/IV (b)/1> wherein X represents -CH2-CH2-or-CH= CH- Y and Z represent hydrogen, halogen, or alkyl (1 to 4 carbon atoms) alkylene represents a straight or branched chain with 2-6 carbon atoms and R represents an alkyl, cycloalkyl or alkenyl group (maximum of 8 carbon atoms each), and processes for their production (1) by reaction of a reactive ester of a hydroxy compound of general formula <FORM:0908788/IV (b)/2> with a primary amine of general formula NH2-R III (2) by reaction of a compound of general formula <FORM:0908788/IV (b)/3> with an aliphatic oxo compound which may be saturated or may contain a double linkage, and reduction of the product, (3) by reduction of a compound of general formula <FORM:0908788/IV (b)/4> wherein alkylene1 and R1 differ from alkylene and R as defined above only in that, in at least one of these radicals, the group bound to a nitrogen atom is a carbonyl group, (4) by splitting into an acid and a secondary amine an amide of general formula <FORM:0908788/IV (b)/5> wherein Ar represents an acyl radical and (5) by catalytic reduction of a compound of general formula <FORM:0908788/IV (b)/6> wherein Av represents an arylmethyl radical. The products have antiallergic, spasmolytic, anticonvulsive and sedative activity. Acyl derivatives of general formula V are prepared, for example, by acylation of amines of general formula IV Acyl derivatives of general formula VI are prepared, for example, by reaction of alkali metal derivatives of compounds of general formula V with reactive esters (such as halides) of low molecular weight alkanols or alkenols by reaction of compounds of general formula <FORM:0908788/IV (b)/7> with reactive esters of alcohols of general formula <FORM:0908788/IV (b)/8> or by reaction of reactive esters of alcohols of general formula II with amides of general formula <FORM:0908788/IV (b)/9> Imides reducible to compounds of general formula I are prepared by reaction of appropriate oxo compounds (aldehydes or ketones) with amino compounds of general formula IV. 5-g -Chloropropyldibenz[b,f]azepine is prepared by reaction of g -chloropropyl bromide with the sodium derivative formed by reaction of sodium amide with dibenz[b,f]azepine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7780659A CH374678A (en) | 1959-09-04 | 1959-09-04 | Process for the preparation of new N-heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES261027A1 true ES261027A1 (en) | 1961-05-16 |
Family
ID=4535970
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0261027A Expired ES261027A1 (en) | 1959-09-04 | 1960-09-03 | Substituted 5h-dibenz[b,f]azepines and their 10,11-dihydro derivatives |
| ES0261025A Expired ES261025A1 (en) | 1959-09-04 | 1960-09-03 | Substituted 5h-dibenz[b,f]azepines and their 10,11-dihydro derivatives |
| ES0261028A Expired ES261028A1 (en) | 1959-09-04 | 1960-09-03 | Substituted 5h-dibenz[b,f]azepines and their 10,11-dihydro derivatives |
| ES0261024A Expired ES261024A1 (en) | 1959-09-04 | 1960-09-03 | Substituted 5h-dibenz[b,f]azepines and their 10,11-dihydro derivatives |
| ES0261026A Expired ES261026A1 (en) | 1959-09-04 | 1960-09-03 | Substituted 5h-dibenz[b,f]azepines and their 10,11-dihydro derivatives |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0261025A Expired ES261025A1 (en) | 1959-09-04 | 1960-09-03 | Substituted 5h-dibenz[b,f]azepines and their 10,11-dihydro derivatives |
| ES0261028A Expired ES261028A1 (en) | 1959-09-04 | 1960-09-03 | Substituted 5h-dibenz[b,f]azepines and their 10,11-dihydro derivatives |
| ES0261024A Expired ES261024A1 (en) | 1959-09-04 | 1960-09-03 | Substituted 5h-dibenz[b,f]azepines and their 10,11-dihydro derivatives |
| ES0261026A Expired ES261026A1 (en) | 1959-09-04 | 1960-09-03 | Substituted 5h-dibenz[b,f]azepines and their 10,11-dihydro derivatives |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE594720A (en) |
| CH (1) | CH374678A (en) |
| CY (1) | CY340A (en) |
| ES (5) | ES261027A1 (en) |
| GB (1) | GB908788A (en) |
| MY (1) | MY6600056A (en) |
-
1959
- 1959-09-04 CH CH7780659A patent/CH374678A/en unknown
-
1960
- 1960-09-02 GB GB30261/60A patent/GB908788A/en not_active Expired
- 1960-09-03 ES ES0261027A patent/ES261027A1/en not_active Expired
- 1960-09-03 ES ES0261025A patent/ES261025A1/en not_active Expired
- 1960-09-03 ES ES0261028A patent/ES261028A1/en not_active Expired
- 1960-09-03 ES ES0261024A patent/ES261024A1/en not_active Expired
- 1960-09-03 ES ES0261026A patent/ES261026A1/en not_active Expired
- 1960-09-05 BE BE594720A patent/BE594720A/en unknown
-
1966
- 1966-02-12 CY CY34066A patent/CY340A/en unknown
- 1966-12-31 MY MY196656A patent/MY6600056A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH374678A (en) | 1964-01-31 |
| GB908788A (en) | 1962-10-24 |
| ES261028A1 (en) | 1961-05-16 |
| ES261025A1 (en) | 1961-05-16 |
| MY6600056A (en) | 1966-12-31 |
| ES261024A1 (en) | 1961-05-16 |
| ES261026A1 (en) | 1961-05-16 |
| CY340A (en) | 1966-02-12 |
| BE594720A (en) | 1961-03-06 |
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