- Synthesis method of 3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one
-
The invention discloses a synthesis method of 3-bromine-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one, and belongs to the technical field of organic synthesis. The synthesis method comprises the steps that gamma-butyrolactone and benzene which are cheap and easy to obtain serve as starting raw materials, 2-bromo-1-tetralone, 2-bromo-3,4-dihydro-N-hydroxy-(2H)-naphthalimide and 3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one are synthesized in sequence . According to the synthetic method, gamma-butyrolactone and benzene are taken as starting raw materials, and 3-bromo-1,3,4,5-tetrahydro-2H-1-benzoazepin-2-one is obtained through cyclization reaction, bromination reaction, oxime forming reaction and Beckmann rearrangement reaction respectively. The method has the advantages of simple production process, low production cost, simplicity in operation, less three wastes, small environmental pollution and suitability for industrial production.
- -
-
Paragraph 0024-0025
(2021/07/24)
-
- A 3 - bromo - 1, 3, 4, 5 - tetrahydro - 2 H - 1 - benzazepine - 2 - one preparation method
-
The invention discloses a preparation method of 3-bromo-1,3,4,5-tetrahydro-2H-benzazepine-2-keto. The preparation method comprises the following stages: alpha-tetralone preparation stage, 2-bromo-3,4-dihydro-N-hydroxy-(2H)-naphthalimide preparation stage and 3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepine-2-keto, wherein the alpha-tetralone preparation stage comprises the following steps: after mixing gamma-butyrolactone, benzene and aluminum chloride anhydrous, raising the temperature to be 60-90 DEG C, and preserving the temperature for reaction for 5-30 hours; after the reaction is finished, performing hydrolysis, layering and washing on 25 parts of 6% hydrochloric acid solution until neutral; and then distilling to remove excessive benzene, and performing high vacuum rectification to obtain alpha-tetralone. Then, the finished product is finally prepared through a bromination reaction, an oximation reaction and a beckmann rearrangement reaction, the purity of the finished product is high, and the yield is as high as more than 90%. Moreover, the production technology is simple, the production cost is low, and the pollution is little.
- -
-
Paragraph 0032; 0050-0051; 0056-0057
(2017/10/22)
-
- Discovery of novel triazolobenzazepinones as γ-secretase modulators with central Aβ42 lowering in rodents and rhesus monkeys
-
Abstract Synthesis and SAR studies of novel triazolobenzazepinones as gamma secretase modulators (GSMs) are presented in this communication. Starting from our azepinone leads, optimization studies toward improving central lowering of Aβ42 led to the discovery of novel benzo-fused azepinones. Several benzazepinones were profiled in vivo and found to lower brain Aβ42 levels in Sprague Dawley rats and transgenic APP-YAC mice in a dose-dependent manner after a single oral dose. Compound 34 was further progressed into a pilot study in our cisterna-magna-ported rhesus monkey model, where we observed robust lowering of CSF Aβ42 levels.
- Fischer, Christian,Zultanski, Susan L.,Zhou, Hua,Methot, Joey L.,Shah, Sanjiv,Hayashi, Ikuo,Hughes, Bethany L.,Moxham, Christopher M.,Bays, Nathan W.,Smotrov, Nadya,Hill, Armetta D.,Pan, Bo-Sheng,Wu, Zhenhua,Moy, Lily Y.,Tanga, Flobert,Kenific, Candia,Cruz, Jonathan C.,Walker, Deborah,Bouthillette, Melanie,Nikov, George N.,Deshmukh, Sujal V.,Jeliazkova-Mecheva, Valentina V.,Diaz, Damaris,Michener, Maria S.,Cook, Jacquelynn J.,Munoz, Benito,Shearman, Mark S.
-
p. 3488 - 3494
(2015/08/06)
-
- N-formyl hydroxylamine containing compounds useful as ACE inhibitors and/or NEP inhibitors
-
N-formyl hydroxylamines are provided which have the structure wherein R is H, alkyl, alkenyl, aryl-(CH2)p—, heteroaryl-(CH2)p— or cycloheteroalkyl-(CH2)p— R1is H or COR2where R2is alkyl, aryl-(CH2)p—, cycloheteroalkyl-(CH2)p—, heteroaryl-(CH2)p—, alkoxy or cycloalkyl-(CH2)p—, p is 0 to 8, and A is a dipeptide derived from an amino acid or is a conformationally restricted dipeptide mimic. The above compounds are useful in treating hypertension congestive heart failure, renal failure, and hepatic cirrhosis.
- -
-
Page column 28
(2010/02/08)
-
- Kinetic resolution of a intermediate useful in the production of benazepril and analogues thereof
-
The present invention provides an efficient synthetic process for making benazepril and analogues thereof by having an intermediate compound undergo epimerization and kinetic resolution.
- -
-
-
- MONOCYCLIC OR BICYCLIC CARBOCYCLES AND HETEROCYCLES AS FACTOR XA INHIBITORS
-
The present application describes monocyclic or bicyclic carbocycles and heterocycles and derivatives thereof of Formula I: or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of factor Xa.
- -
-
-
- Pharmaceuticals which promote gastrointestinal blood circulation
-
The use is described of compounds of the general formula I STR1 wherein R1 represents a phenyl-lower alkyl group which can optionally be substituted in the phenyl ring by lower alkyl, lower alkoxy or halogen, or represents a naphthyl-lower alkyl group, R2 denotes hydrogen or a biolabile ester-forming group, and R3 denotes hydrogen or a biolabile ester-forming group, and physiologically acceptable salts of the acids of formula I for preparing pharmaceutical compositions for the treatment and/or prophylaxis of gastrointestinal blood circulation disturbances.
- -
-
-
- BENZAZEPINE-, BENZOXAZEPINE- AND BENZOTHIAZEPINE-N-ACETIC ACID DERIVATIVES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
-
Compounds with neutral endopeptidase (NEP) inhibitory activity corresponding to the formula I STR1 in which R 1 is a lower alkoxy-lower-alkyl group whose lower alkoxy radical is substituted by a lower alkoxy group, or a phenyl-lower-alkyl or phenyloxy-lower-alkyl group which can optionally be substituted in the phenyl ring by lower alkyl, lower alkoxy or halogen, or a naphthyl-lower-alkyl group, A is CH 2, O or S,R 2 is hydrogen or halogen,R. sup.3 is hydrogen or halogen,R 4 is hydrogen or a group forming a biolabile ester, andR 5 is hydrogen or a group forming a biolabile ester, and the physiologically acceptable acid addition salts thereof.
- -
-
-
- Aminothiazole Derivatives. II. A Facile Synthesis of Condensed 4-Aminothiazole Derivatives using α-Bromolactams and Thioamides
-
The reaction of an α-bromolactam with a thioamide was found to give a cyclic 4-aminothiazole derivative.Novel heterocyclic compounds such as 4,5,6,7-tetrahydrothiazolopyridines 10, 5,6,7,8-tetrahydro-4H-thiazoloazepines 11, 4,5,6,7,8,9-hexahydrothiazoloazocine 12 and 9,10-dihydro-4H-thiazolobenzazepines 18 were thus prepared and the utility of this method in the construction of 4-aminothiazole-containing compounds was suggested.
- Uchikawa, Osamu,Aono, Tetsuya
-
p. 1545 - 1552
(2007/10/02)
-
- 3-Amino-[1]-benzazepin-2-one-1-alkanoic acids
-
Variously substituted 1-carboxymethyl-3-(carboxymethylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-ones and functional derivatives are angiotensin converting enzyme inhibitors and are useful as antihypertensive agents. Synthesis of, compositions and methods of treatment utilizing such compounds are included.
- -
-
-
- 3-Amino-[1]-benzazepin-2-one-1-alkanoic acids
-
Variously substituted 1-carboxymethyl-3-(carboxymethylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-ones and functional derivatives are angiotension converting enzyme inhibitors and are useful as antihypertensive agents. Synthesis of, compositions and methods of treatment utilizing such compounds are included.
- -
-
-
