GB1038914A - New azepine derivatives, processes for their production and compositions containing same - Google Patents
New azepine derivatives, processes for their production and compositions containing sameInfo
- Publication number
- GB1038914A GB1038914A GB47592/63A GB4759263A GB1038914A GB 1038914 A GB1038914 A GB 1038914A GB 47592/63 A GB47592/63 A GB 47592/63A GB 4759263 A GB4759263 A GB 4759263A GB 1038914 A GB1038914 A GB 1038914A
- Authority
- GB
- United Kingdom
- Prior art keywords
- azepine
- dibenz
- methyl
- acetyl
- chloro
- 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
- 150000001538 azepines Chemical class 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 title 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 12
- -1 alkanoyl radical Chemical class 0.000 abstract 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 230000007062 hydrolysis Effects 0.000 abstract 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract 4
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 239000000932 sedative agent Substances 0.000 abstract 2
- KEVXBVBTHBDMBY-UHFFFAOYSA-N (6-methyl-11H-benzo[b][1]benzazepin-4-yl)methanamine Chemical compound CC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2CN KEVXBVBTHBDMBY-UHFFFAOYSA-N 0.000 abstract 1
- IPXXMSDJCAXSFN-UHFFFAOYSA-N 1-(11H-benzo[b][1]benzazepin-5-yl)-N,N-diethylethanamine Chemical compound C(C)N(C(C)C1=CC2=C(NC3=C1C=CC=C3)C=CC=C2)CC IPXXMSDJCAXSFN-UHFFFAOYSA-N 0.000 abstract 1
- CHPUDNBTTNDZHC-UHFFFAOYSA-N 1-(11H-benzo[b][1]benzazepin-5-yl)-N,N-dimethylethanamine Chemical compound CN(C(C)C1=CC2=C(NC3=C1C=CC=C3)C=CC=C2)C CHPUDNBTTNDZHC-UHFFFAOYSA-N 0.000 abstract 1
- JMGCRTKWZXSNEW-UHFFFAOYSA-N 1-(11H-benzo[b][1]benzazepin-5-yl)-N,N-dimethylmethanamine Chemical compound CN(C)CC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2 JMGCRTKWZXSNEW-UHFFFAOYSA-N 0.000 abstract 1
- IZHJALHRUHBPNC-UHFFFAOYSA-N 1-(11H-benzo[b][1]benzazepin-5-yl)-N-methylethanamine Chemical compound CNC(C)C1=CC2=C(NC3=C1C=CC=C3)C=CC=C2 IZHJALHRUHBPNC-UHFFFAOYSA-N 0.000 abstract 1
- MGEGVIICZIJBSA-UHFFFAOYSA-N 1-(11H-benzo[b][1]benzazepin-5-yl)-N-methylmethanamine Chemical compound CNCC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2 MGEGVIICZIJBSA-UHFFFAOYSA-N 0.000 abstract 1
- XRNUHRNXIZMCIH-UHFFFAOYSA-N 1-(2,9-dichloro-11H-benzo[b][1]benzazepin-5-yl)-N,N-dimethylmethanamine Chemical compound ClC=1C=CC2=C(NC3=C(C(=C2)CN(C)C)C=CC(=C3)Cl)C1 XRNUHRNXIZMCIH-UHFFFAOYSA-N 0.000 abstract 1
- IKAKEAOWHJQDSQ-UHFFFAOYSA-N 1-(2,9-dichloro-5-methylbenzo[b][1]benzazepin-11-yl)ethanone Chemical compound C(C)(=O)N1C2=C(C=C(C3=C1C=C(C=C3)Cl)C)C=CC(=C2)Cl IKAKEAOWHJQDSQ-UHFFFAOYSA-N 0.000 abstract 1
- LEKLXMHRVHTZIH-UHFFFAOYSA-N 1-(2-chlorobenzo[b][1]benzazepin-11-yl)ethanone Chemical compound C(C)(=O)N1C2=C(C=CC3=C1C=CC=C3)C=CC(=C2)Cl LEKLXMHRVHTZIH-UHFFFAOYSA-N 0.000 abstract 1
- PTSJWMUKAASJOV-UHFFFAOYSA-N 1-(5,6-dibromo-2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethanone Chemical compound ClC=1C=CC2=C(N(C3=C(C(C2Br)Br)C=CC=C3)C(C)=O)C1 PTSJWMUKAASJOV-UHFFFAOYSA-N 0.000 abstract 1
- GYXAGFQSEKCVIB-UHFFFAOYSA-N 1-(5-methylbenzo[b][1]benzazepin-11-yl)ethanone Chemical compound C(C)(=O)N1C2=C(C=C(C3=C1C=CC=C3)C)C=CC=C2 GYXAGFQSEKCVIB-UHFFFAOYSA-N 0.000 abstract 1
- OLUOSLXXLHKQHM-UHFFFAOYSA-N 1-[5-(bromomethyl)-2,9-dichlorobenzo[b][1]benzazepin-11-yl]ethanone Chemical compound C(C)(=O)N1C2=C(C=C(C3=C1C=C(C=C3)Cl)CBr)C=CC(=C2)Cl OLUOSLXXLHKQHM-UHFFFAOYSA-N 0.000 abstract 1
- RTXGWROFMKXMKB-UHFFFAOYSA-N 1-[5-(bromomethyl)-2-chlorobenzo[b][1]benzazepin-11-yl]ethanone Chemical compound ClC=1C=CC2=C(N(C3=C(C=C2CBr)C=CC=C3)C(C)=O)C1 RTXGWROFMKXMKB-UHFFFAOYSA-N 0.000 abstract 1
- FJEVESSCCQDZBU-UHFFFAOYSA-N 1-[5-(bromomethyl)benzo[b][1]benzazepin-11-yl]ethanone Chemical compound BrCC1=CC2=C(N(C3=C1C=CC=C3)C(C)=O)C=CC=C2 FJEVESSCCQDZBU-UHFFFAOYSA-N 0.000 abstract 1
- GPBIDTQXIMEYFB-UHFFFAOYSA-N 1-[6-(bromomethyl)-2-chlorobenzo[b][1]benzazepin-11-yl]ethanone Chemical compound ClC=1C=CC2=C(N(C3=C(C(=C2)CBr)C=CC=C3)C(C)=O)C1 GPBIDTQXIMEYFB-UHFFFAOYSA-N 0.000 abstract 1
- ARXZZCMGABHGTL-UHFFFAOYSA-N 1-[6-(dimethylamino)-4-methylbenzo[b][1]benzazepin-11-yl]ethanone Chemical compound CN(C1=CC2=C(N(C3=C1C=CC=C3)C(C)=O)C=CC=C2C)C ARXZZCMGABHGTL-UHFFFAOYSA-N 0.000 abstract 1
- PNCDVDWIMYCMEI-UHFFFAOYSA-N 11-benzyl-2-chloro-5-methyl-6H-benzo[b][1]benzazepin-5-ol Chemical compound ClC=1C=CC2=C(N(C3=C(CC2(O)C)C=CC=C3)CC3=CC=CC=C3)C1 PNCDVDWIMYCMEI-UHFFFAOYSA-N 0.000 abstract 1
- LKAUEOQKFVQEEA-UHFFFAOYSA-N 11-benzyl-2-chloro-5-methylbenzo[b][1]benzazepine Chemical compound ClC=1C=CC2=C(N(C3=C(C=C2C)C=CC=C3)CC3=CC=CC=C3)C1 LKAUEOQKFVQEEA-UHFFFAOYSA-N 0.000 abstract 1
- KOGOKDZBPJSSIL-UHFFFAOYSA-N 11-benzyl-2-chloro-5H-benzo[b][1]benzazepin-6-one hydrochloride Chemical compound ClC=1C=CC2=C(N(C3=C(C(C2)=O)C=CC=C3)CC3=CC=CC=C3)C1.Cl KOGOKDZBPJSSIL-UHFFFAOYSA-N 0.000 abstract 1
- PUJNXDVXQDIMLE-UHFFFAOYSA-N 11-benzyl-2-chloro-6-methoxybenzo[b][1]benzazepine Chemical compound ClC=1C=CC2=C(N(C3=C(C(=C2)OC)C=CC=C3)CC3=CC=CC=C3)C1 PUJNXDVXQDIMLE-UHFFFAOYSA-N 0.000 abstract 1
- GJPUTKWVQJEZPE-UHFFFAOYSA-N 1h-azepin-2-amine Chemical compound NC1=CC=CC=CN1 GJPUTKWVQJEZPE-UHFFFAOYSA-N 0.000 abstract 1
- GBJXYEFCCOLWFW-UHFFFAOYSA-N 2-chloro-5-methyl-11H-benzo[b][1]benzazepine Chemical compound ClC=1C=CC2=C(NC3=C(C=C2C)C=CC=C3)C1 GBJXYEFCCOLWFW-UHFFFAOYSA-N 0.000 abstract 1
- FCQUTDPPHFRPNJ-UHFFFAOYSA-N 2-chloro-6-methyl-11H-benzo[b][1]benzazepine Chemical compound CC1=CC2=C(NC3=C1C=CC=C3)C=C(C=C2)Cl FCQUTDPPHFRPNJ-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- FLYQOYRQGQYTKP-UHFFFAOYSA-N 5-(piperidin-1-ylmethyl)-11H-benzo[b][1]benzazepine hydrochloride Chemical compound Cl.N1(CCCCC1)CC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2 FLYQOYRQGQYTKP-UHFFFAOYSA-N 0.000 abstract 1
- VOGVWOSRBPITFC-UHFFFAOYSA-N 5-methyl-11h-benzo[b][1]benzazepine Chemical compound CC1=CC2=CC=CC=C2NC2=CC=CC=C12 VOGVWOSRBPITFC-UHFFFAOYSA-N 0.000 abstract 1
- 206010002091 Anaesthesia Diseases 0.000 abstract 1
- 238000003747 Grignard reaction Methods 0.000 abstract 1
- OXZFCLQNDKQGKE-UHFFFAOYSA-N N-(11H-benzo[b][1]benzazepin-5-ylmethyl)-N-ethylethanamine Chemical compound C(C)N(CC)CC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2 OXZFCLQNDKQGKE-UHFFFAOYSA-N 0.000 abstract 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 150000001263 acyl chlorides Chemical class 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000746 allylic group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000037005 anaesthesia Effects 0.000 abstract 1
- 238000001949 anaesthesia Methods 0.000 abstract 1
- 230000002082 anti-convulsion Effects 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 230000001387 anti-histamine Effects 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000006264 debenzylation reaction Methods 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- XNTYINWAOZRMSU-UHFFFAOYSA-N ethyl N-(11H-benzo[b][1]benzazepin-5-ylmethyl)-N-methylcarbamate Chemical compound C(C)OC(=O)N(C)CC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2 XNTYINWAOZRMSU-UHFFFAOYSA-N 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 229940125723 sedative agent Drugs 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1421662A CH412906A (de) | 1962-12-04 | 1962-12-04 | Verfahren zur Herstellung von neuen Azepinderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1038914A true GB1038914A (en) | 1966-08-10 |
Family
ID=4398918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47592/63A Expired GB1038914A (en) | 1962-12-04 | 1963-12-03 | New azepine derivatives, processes for their production and compositions containing same |
Country Status (10)
| Country | Link |
|---|---|
| AT (2) | AT243274B (https=) |
| BE (1) | BE640820A (https=) |
| BR (1) | BR6355096D0 (https=) |
| CH (2) | CH416645A (https=) |
| DE (2) | DE1445826B1 (https=) |
| DK (2) | DK107750C (https=) |
| ES (2) | ES294339A1 (https=) |
| FI (2) | FI42560B (https=) |
| GB (1) | GB1038914A (https=) |
| NL (2) | NL125064C (https=) |
-
0
- NL NL301291D patent/NL301291A/xx unknown
- NL NL125064D patent/NL125064C/xx active
-
1962
- 1962-11-04 CH CH564066A patent/CH416645A/de unknown
- 1962-12-04 CH CH1421662A patent/CH412906A/de unknown
-
1963
- 1963-12-02 FI FI2374/63A patent/FI42560B/fi active
- 1963-12-03 GB GB47592/63A patent/GB1038914A/en not_active Expired
- 1963-12-03 DE DE19631445826D patent/DE1445826B1/de active Pending
- 1963-12-03 ES ES0294339A patent/ES294339A1/es not_active Expired
- 1963-12-03 AT AT968063A patent/AT243274B/de active
- 1963-12-03 ES ES0294340A patent/ES294340A1/es not_active Expired
- 1963-12-03 AT AT460764A patent/AT242159B/de active
- 1963-12-03 DE DE19631795513 patent/DE1795513A1/de active Pending
- 1963-12-03 DK DK161965AA patent/DK107750C/da active
- 1963-12-03 DK DK564863AA patent/DK107293C/da active
- 1963-12-03 BR BR155096/63A patent/BR6355096D0/pt unknown
- 1963-12-04 BE BE640820D patent/BE640820A/xx unknown
-
1969
- 1969-10-06 FI FI2873/69A patent/FI42562B/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| DE1445826B1 (de) | 1970-11-19 |
| CH412906A (de) | 1966-05-15 |
| DK107750C (da) | 1967-07-03 |
| DK107293C (da) | 1967-05-16 |
| CH416645A (de) | 1966-07-15 |
| ES294339A1 (es) | 1964-05-16 |
| BE640820A (https=) | 1964-06-04 |
| NL301291A (https=) | |
| NL125064C (https=) | |
| ES294340A1 (es) | 1964-06-01 |
| AT242159B (de) | 1965-09-10 |
| DE1795513A1 (de) | 1972-01-13 |
| FI42562B (https=) | 1970-06-01 |
| BR6355096D0 (pt) | 1973-07-19 |
| FI42560B (https=) | 1970-06-01 |
| AT243274B (de) | 1965-11-10 |
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