IE38775B1 - Benzazepine derivatives - Google Patents
Benzazepine derivativesInfo
- Publication number
- IE38775B1 IE38775B1 IE123/74A IE12374A IE38775B1 IE 38775 B1 IE38775 B1 IE 38775B1 IE 123/74 A IE123/74 A IE 123/74A IE 12374 A IE12374 A IE 12374A IE 38775 B1 IE38775 B1 IE 38775B1
- Authority
- IE
- Ireland
- Prior art keywords
- methyl
- substituted
- chloro
- hydrogen
- benzyl
- Prior art date
Links
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
- C07D471/12—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 three hetero rings
- C07D471/16—Peri-condensed systems
Abstract
1449331 Octahydropyridoindolobenzazepines ENDO LABORATORIES Inc 21 Jan 1974 [22 Jan 1973 11 May 1973 6 Dec 1973 (2)] 02657/74 Heading C2C Novel octahydropyridoindolobenzazepines of the general formula n is zero or one; X is an anion of a pharmaceutically suitable acid; and R is hydrogen; 3-chloro-2-butenyl; 2-bromoallyl; benzyl; benzyl ring-substituted with methyl, methoxy or chloro; phenethyl; 3-phenylpropyl; 3-phenylpropyl ring substituted with chloro, bromo or methoxy; furfurtyl; 2-thenyl; acetonyl; phenacyl; C 1 -C 5 , alkyl; C 3 -C 5 alkenyl; C 3 -C 5 alkynyl; cinnamyl; cinnamyl ring-substituted with chloro, bromo, or methoxy; 3-phenyl-2- propynyl; cyclopropyl ; C 4 -C 8 cycloalkylmethyl (methylcyclopropyl)methyl; (cis - 2,3 - dimethylcyclopropyl)methyl; C 6 -C 8 cyclo = alkenylmethyl; C 6 -C 8 cycloalkadienylmethyl; (2,3-dimethylcycloprop- 2 - en - 1 - yl)methyl; exo - 7 - norcarylmethyl; (cis - 1,6 - dimethylendo - 3 - norcaren - 7 - yl)methyl; (4 - methylbicyclo[2.2.2]oct - 1 - yl)methyl; (4 - methylbicyclo[2.2.2]oct - 2 - en - 1 - yl) methyl; (bicyclo[2.2.1]hept - 2 - yl)methyl; bicyclo[2.2.1]- hept - 2 - en - 5 - yl)methyl; 1 - adamantylmethyl; or 2 - adamantylmethyl, and the hydrogens in the 4a and 14a positions are in trans relationship to each other, are prepared (a) when R is R<SP>a</SP>, which is benzyl; benzyl ring- substituted with methyl, methoxy or chloro; phenethyl; 3 - phenylpropyl; 3 - phenylpropyl ring-substituted by chloro, bromo or methoxy; furfuryl; 2-thenyl; C 1 -C 5 alkyl; cyclopropyl; C 4 -C 8 cycloalkylmethyl; (methyl-cyclopropyl)- methyl; exo - 7 - norcarylmethyl; (4 - methylbicyclo[2.2.2]oct - 1 - yl)methyl; (bicyclo- [2.2.1]hept- 2 - yl)methyl; 1 - adamantylmethyl; or 2 - adamantylmethyl, by reducing with a boron hydride/tetrahydrofuran complex a hexahydro pyridoindolobenzazepine of the general formula wherein R<SP>2</SP> is as R<SP>a</SP> or methoxymethyl or -COR<SP>7</SP>, in which R<SP>7</SP> is phenyl; chlorophenyl; methylphenyl; methoxyphenyl; benzylphenethyl; phenethyl ring - substituted by chloro, bromo or methoxy; 2-furyl; 2-thienyl; hydrogen; C 1 -C 4 alkyl; C 2 -C 4 alkenyl; styryl; styryl ring - substituted by chloro, bromo or methoxy; C 2 -C 7 , cycloalkyl; methylcyclopropyl; C 5 -C 7 cycloalkenyl; C 5 -C 7 cycloalkadienyl; exo - 7 - norcaryl; 4 - methylbioyclo- [2.2.2]oct - 1 - yl; bicyclo[2.2.1]hept - 2 - yl; 4 - methyl - bicyclo[2.2.2]oct - 2 - en - 1 - yl; bicyclo[2.2.1]hept - 2 - en - 5 - yl; 1 - adamantyl; or 2 - adamantyl; followed by acidification; (b) when R is hydrogen, by reacting the corresponding compound in which R is R<SP>6</SP>, which is methyl; ethyl; benzyl; benzyl ring- substituted by chloro, methyl or methoxy; or cyclopropylmethyl, with a compound of the general formula ClCOOR<SP>3</SP>, wherein R<SP>3</SP> is C 1 -C 4 alkyl; vinyl; benzyl; p-methylbenzyl; p-methoxybenzyl; or phenyl, and subjecting the resulting ester of the general formula to hydrolysis or, when R<SP>3</SP> is benzyl or substituted benzyl, to hydrolysis or hydrogenolysis; (c) when R is R<SP>c</SP>, which is as R with the exception of hydrogen, cyclopropyl and (cis-2,3-dimethylcyclopropyl)methyl, by alkylating the corresponding compound in which R is hydrogen with a compound of the general formula (i) R<SP>c</SP>Z, wherein Z is Cl, Br, I or -OS(O) 2 R<SP>8</SP>, in which R<SP>8</SP> is CH 3 , phenyl or p-tolyl, or (ii) wherein R<SP>9</SP> is C 1 -C 4 alkyl, in the presence of an acid acceptor; (d) when R is R<SP>d</SP>, which is as R with the exception of hydrogen, acetonyl, phenacyl, cyclopropyl, cinnamyl, substituted cinnamyl, 3-phenyl-2-propynyl and (cis-2,3- dimethylcyclopropyl)methyl, by acylating the corresponding compound wherein R is hydrogen with a compound of the general formula QCOR<SP>4</SP>, wherein R<SP>4</SP> is 2-chloro-1-propenyl; 1- bromovinyl; phenyl; chlorophenyl; methylphenyl; methoxyphenyl; benzyl; phenethyl; phenethyl ring-substituted with chloro, bromo, or methoxy; 2-furyl; 2-thienyl; hydrogen; C 1 -C 4 -alkyl; C 2 -C 4 alkenyl; C 2 -C 4 alkynyl; styryl; styryl ring substituted with chloro, bromo, or methoxy; phenylethynyl; C 3 -C 7 cycloalkyl; methylcyclopropyl; C 5 -C 7 cycloalkenyl; C 5 -C 7 cycloalkadienyl; 2,3-dimethylcycloprop - 2 - en - 1 - yl; exo - 7 - norcaryl; cis - 1,6 - dimethyl - endo - 3 - norcaren - 7 - yl; 4 - methyl - bicyclo[2.2.2]oct - 1 - yl; bicyclo- [2.2.1]hept - 2 - yl; 4 - methylbicyclo[2.2.2]- oct - 2 - en - 1 - yl; bicyclo - [2.2.1]hept - 2 - en- 5 - yl; 1 - adamantyl; or 2 - adamantyl; Q is -Cl, -Br, C 1 -C 4 alkoxy; or R<SP>5</SP> is different from R<SP>4</SP> and is C 1 -C 4 alkyl, provided that when R<SP>4</SP> is hydrogen, R<SP>5</SP> is methyl; and R<SP>6</SP> is C 1 -C 4 alkyl; and reducing the resulting ketone of the general formula with a metal hydride; and (e) when R is (cis- 2,3-dimethylcyclopropyl)methyl, by catalytically hydrogenating the corresponding compound in which R is (2,3-dimethylcycloprop-2-en-1-yl)- methyl; followed optionally by salification of a resulting free base. Hexahydropyridoindolobenzazepines of the second general formula above are prepared (a) when R<SP>2</SP> is methoxymethyl, by reacting the corresponding compound in which R<SP>2</SP> is hydrogen with chloromethyl methyl ether; (b) when R<SP>2</SP> is hydrogen, benzyl or -COR<SP>7</SP>, by condensing 5 - amino - 10,11 - dihydro - 5H - dibenz- [b,f]azepine with 4-piperidone, optionally 1- substituted by benzyl or -COR<SP>7</SP>, in the presence of an acid; (c) when R<SP>2</SP> is -CH 2 R<SP>7</SP>, by reducing the corresponding compound in which R<SP>2</SP> is -COR<SP>7</SP>; and (d) when R<SP>2</SP> is -COR<SP>7</SP>, by acylating the corresponding compound in which R<SP>2</SP> is hydrogen. Pharmaceutical compositions having analgesic and sedative-tranquillizer activity comprise, as active ingredient, at least one pyridoindolobenzazepine of the first general formula above, together with a pharmaceutically suitable vehicle.
[GB1449331A]
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32535273A | 1973-01-22 | 1973-01-22 | |
| US359504A US3890327A (en) | 1973-05-11 | 1973-05-11 | Trans-1,2,3,4,4a,8,9,14a-octahydropyrido(r',3':2,3)indolo(1,7-ab)+8 1)benzazepine |
| US42261573A | 1973-12-06 | 1973-12-06 | |
| US05/422,616 US3932650A (en) | 1973-01-22 | 1973-12-06 | Trans-octahydropyridoindolobenzazepines as central nervous system depressants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE38775L IE38775L (en) | 1974-07-22 |
| IE38775B1 true IE38775B1 (en) | 1978-05-24 |
Family
ID=27502310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE123/74A IE38775B1 (en) | 1973-01-22 | 1974-01-22 | Benzazepine derivatives |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS49108100A (en) |
| AR (1) | AR207113A1 (en) |
| AT (1) | AT340429B (en) |
| BE (1) | BE809977A (en) |
| CA (1) | CA993872A (en) |
| CH (1) | CH601298A5 (en) |
| DD (1) | DD111906A5 (en) |
| DE (1) | DE2402391A1 (en) |
| FR (1) | FR2214478B1 (en) |
| GB (1) | GB1449331A (en) |
| HU (1) | HU169309B (en) |
| IE (1) | IE38775B1 (en) |
| IL (1) | IL44042A (en) |
| LU (1) | LU69210A1 (en) |
| NL (1) | NL7400849A (en) |
| NO (1) | NO140822C (en) |
| PH (1) | PH11128A (en) |
| SE (1) | SE407802B (en) |
-
1973
- 1973-12-13 SE SE7316847A patent/SE407802B/en unknown
-
1974
- 1974-01-01 AR AR251998A patent/AR207113A1/en active
- 1974-01-18 DD DD176085A patent/DD111906A5/xx unknown
- 1974-01-18 DE DE2402391A patent/DE2402391A1/en active Pending
- 1974-01-21 AT AT50074A patent/AT340429B/en not_active IP Right Cessation
- 1974-01-21 FR FR7401949A patent/FR2214478B1/fr not_active Expired
- 1974-01-21 LU LU69210A patent/LU69210A1/xx unknown
- 1974-01-21 GB GB265774A patent/GB1449331A/en not_active Expired
- 1974-01-21 CA CA190,610A patent/CA993872A/en not_active Expired
- 1974-01-21 NO NO740177A patent/NO140822C/en unknown
- 1974-01-21 PH PH15429A patent/PH11128A/en unknown
- 1974-01-21 BE BE140016A patent/BE809977A/en unknown
- 1974-01-21 IL IL44042A patent/IL44042A/en unknown
- 1974-01-22 IE IE123/74A patent/IE38775B1/en unknown
- 1974-01-22 JP JP49010045A patent/JPS49108100A/ja active Pending
- 1974-01-22 NL NL7400849A patent/NL7400849A/xx not_active Application Discontinuation
- 1974-01-22 CH CH84874A patent/CH601298A5/xx not_active IP Right Cessation
- 1974-01-22 HU HUEO311A patent/HU169309B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS49108100A (en) | 1974-10-14 |
| AT340429B (en) | 1977-12-12 |
| ATA50074A (en) | 1977-04-15 |
| HU169309B (en) | 1976-11-28 |
| LU69210A1 (en) | 1975-04-11 |
| BE809977A (en) | 1974-07-22 |
| NO140822B (en) | 1979-08-13 |
| IL44042A0 (en) | 1974-05-16 |
| IE38775L (en) | 1974-07-22 |
| SE407802B (en) | 1979-04-23 |
| DD111906A5 (en) | 1975-03-12 |
| NL7400849A (en) | 1974-07-24 |
| DE2402391A1 (en) | 1974-07-25 |
| GB1449331A (en) | 1976-09-15 |
| PH11128A (en) | 1977-10-27 |
| CH601298A5 (en) | 1978-07-14 |
| IL44042A (en) | 1977-02-28 |
| CA993872A (en) | 1976-07-27 |
| FR2214478B1 (en) | 1978-01-13 |
| AU6470774A (en) | 1975-07-24 |
| NO140822C (en) | 1979-11-21 |
| FR2214478A1 (en) | 1974-08-19 |
| NO740177L (en) | 1974-07-23 |
| AR207113A1 (en) | 1976-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Matsmura et al. | Stereoselective syntheses of solenopsin A and B | |
| GB1450002A (en) | Pyridoindoles | |
| Yadav et al. | Cyclopentane synthesis and annulation: intramolecular radical cyclization of acetals | |
| EP0996619A1 (en) | Tropane analogs and methods for inhibition of monoamine transport | |
| IE38775B1 (en) | Benzazepine derivatives | |
| Umezawa et al. | A synthesis of (±)-Δ2-α-Lycoren-7-one, the key intermediate for the total synthesis of (±)-lycorine | |
| Sauers et al. | Stereochemistry of Reactions of 7-Norbornenyl Anions | |
| KAHN et al. | Design and synthesis of nonpeptide mimetics of jaspamide | |
| Macdonald et al. | Pyrrolizidine alkaloid synthesis.(.+-.)-Supinidine | |
| Moursounidis et al. | A synthesis and some reactions of 7-Oxabicyclo [2.2. 1] heptan-2-one | |
| Hino et al. | Synthesis of bioactive nitrogen heterocycles from marine organisms | |
| Cainelli et al. | A synthetic approach to 4-oxo and 4-thioxo azetidinones from heterocumulenes and ester enolates. A novel synthesis of 4-thio-acetoxy azetidin-2-ones. | |
| Garin | Cyclobutene epoxides. Stereospecific Lewis acid rearrangement | |
| Wolfe et al. | Dianions derived from glutarimide, 3, 5-morpholinedione, and 3, 5-thiomorpholinedione as useful new synthetic intermediates | |
| Alber et al. | 6-Methyltetracyclo [4.2. 0.01, 7.05, 7] octane-a bridged [3.3. 3] fenestrane | |
| Schaub et al. | Prostaglandins and congeners II. The conjugate addition of 3-t-butoxyoctyl magnesium bromide to cyclopentenones. A synthesis of rac. 11-deoxy-13-dihydroprostaglandin-E1. | |
| HAGIWARA | Annulation via Sequential Multifold Michael Reaction-One Aspect of Terpenoid Synthesis | |
| GB1289273A (en) | ||
| ES364930A1 (en) | 10 (or 11) - dihald - 5-(3-dimethylaminopropyl or -propylidene) - 5h-dibenzo(a | |
| IMANISHI et al. | 1, 6-Dihydro-3 (2H)-pyridinones. II. Synthesis of 2-Azabicyclo [2. 2. 2] octanes by the Reaction of N-Substituted 1, 6-Dihydro-3 (2H)-pyridinones with 1, 3-Dicarbonyl Compounds | |
| Goldberg et al. | Alumina-catalyzed dehydration of 1-ferrocenylethanol. Formation of 1, 3-diferrocenyl-1-butene | |
| Veselovsky et al. | Cationic cyclization of regular α-monoterpenols as a model for tri-and tetracyclic diterpene biosynthesis | |
| Walter et al. | Annelation of ethyl propiolate with ethyl pipecolate | |
| Jeng et al. | Formation of Pyrrole Derivatives from Heteroatom‐Substituted Acetonitriles | |
| Kawano et al. | Thermal cyclization of 1-{(Z)-1-hexene-3, 5-diynyl}-2-(1, 3-butanediynyl) benzene leading to dinaphtho [1, 2-b: 2, 1-f] semibullvalene and dinaphtho [2, 1-b: 1, 2-j] elassovalene skeletons via cyclobuta [a] naphthalene |