cas 20925-64-8, 7,8-Dimethoxy-1,3,4,5-tetrahydrobenzo[d]azepin-2-one

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Design of oxa-spirocyclic PHOX ligands for the asymmetric synthesis of lorcaserin: Via iridium-catalyzed asymmetric hydrogenation
Phosphine-oxazoline (PHOX) ligands are a very important class of privileged ligands in asymmetric catalysis. A series of highly rigid oxa-spiro phosphine-oxazoline (O-SIPHOX) ligands based on O-SPINOL was synthesized efficiently, and their iridium complexes were synthesized by coordination of the O-SIPHOX ligands to [Ir(cod)Cl]2 in the presence of sodium tetrakis-3,5-bis(trifluoromethyl)phenylborate (NaBArF). The cationic iridium complexes showed high reactivity and excellent enantioselectivity in the asymmetric hydrogenation of 1-methylene-tetrahydro-benzo[d]azepin-2-ones (up to 99% yield and up to 99% ee). A key intermediate of the anti-obesity drug lorcaserin could be efficiently synthesized using this protocol.
Ye, Xiang-Yu,Liang, Zhi-Qin,Jin, Cong,Lang, Qi-Wei,Chen, Gen-Qiang,Zhang, Xumu
supporting information
p. 195 - 198
(2021/01/14)

A ring expansion strategy towards diverse azaheterocycles
The development of innovative strategies for the synthesis of N-heterocyclic compounds is an important topic in organic synthesis. Ring expansion methods to form large N-heterocycles often involve the cycloaddition of strained aza rings with π bonds. However, in some cases such strategies suffer from some limitations owing to the difficulties in controlling the regioselectivity and the accessibility of specific π-bond synthons. Here, we report the development of a general ring expansion strategy that involves a formal cross-dimerization between three-membered aza heterocycles and three- and four-membered-ring ketones through synergistic bimetallic catalysis. These formal cross-dimerizations of two different strained rings are efficient and scalable, and provide a straightforward and broadly applicable means of assembling diverse N-heterocycles, such as 3-benzazepinones, dihydropyridinones and uracils, which are versatile units in numerous drugs and biologically active compounds. Preliminary mechanistic studies revealed that the C–C bond of strained ring ketones is first cleaved by the Pd0 species during the reaction. [Figure not available: see fulltext.].
Li, Ruirui,Li, Bo,Zhang, Hongpeng,Ju, Cheng-Wei,Qin, Ying,Xue, Xiao-Song,Zhao, Dongbing
p. 1006 - 1016
(2021/07/25)

Process for preparation of ivabradine hydrochloride
The present invention relates to crystalline Ivabradine hydrochloride Form-I and a process for its preparation.
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(2012/02/15)

1,2,4,5-Tetrahydro-3H-benzazepine compounds, a process for their preparation and pharmaceutical compositions containing them
Compounds of formula (I): wherein: R1 represents a hydrogen atom or a group selected from cycloalkyl, benzyl and optionally substituted alkyl,R2, R3, R4 and R5 each represent a hydrogen atom or a hydroxy, methyl, —OSO2R10, —OCOR10 or optionally substituted alkoxy group, or R2 and R3, or R3 and R4, or R4 and R5 together form a group —O—(CH2)q—O—, —O—CH═CH—O— or —O—CH═CH—,R6, R7, R8 and R9 each represent a hydrogen atom or an alkoxy group, or R6 and R7, or R7 and R8, or R8 and R9 together form a group —O—(CH2)q—O—-,R10 represents a group selected from linear or branched C1-C6alkoxy, NR11R′11 and optionally substituted alkyl,R11 and R′11 each represent a hydrogen atom or an alkyl group, or R11 and R′1 together with the nitrogen atom carrying them form an optionally substituted, monocyclic or bicyclic, nitrogen-containing heterocycle,X represents O, NH or CH2,m and p each represent 0 or 1,n and q each represent 1 or 2, in racemic form or in the form of optical isomers,and also addition salts thereof with a pharmaceutically acceptable acid. Medicinal products containing the same which are useful in treating various pathologies.
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(2009/04/24)

HETEROCYCLIC AMIDE COMPOUNDS AS PROTEIN KINASE INHIBITORS
The present invention related to novel heterocyclic amide compounds of Formula 1: as disclosed herein or a pharmaceutically accept able salt, solvate, ester, prodrug or stereoisomer thereof. Also disclosedare compositions comprising said compounds, and methods for using said compounds for treating or preventing a proliferative disease, an anti-proliferative disorder, inflammation, arthritis, a neurological or neurodenerative disease, a cardiovascular disease, alopecia, a neuronal disease, an ischemic injury, a viral disease or a fungal disease
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Page/Page column 87-88

(2009/03/07)

SAR studies of capsazepinoid bronchodilators. Part 1: The importance of the catechol moiety and aspects of the B-ring structure
Capsazepine as well as its derivatives and analogues are general inhibitors of constriction of human small airways. From a systematic variation of the capsazepine structure, divided into four regions, SARs were established. This part concerns the catechol moiety of the A-ring as well as the 2,3,4,5-tetrahydro-1H-2-azepine moiety (the B-ring) of capsazepine. It is revealed that a conformational constrain (as a fused ring) is important and that compounds with a six-membered B-ring (as a 1,2,3,4-tetrahydroisoquinoline) in general are more potent than the corresponding isoindoline, 2,3,4,5-tetrahydro-1H-2-benzazepine and 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives.
Dalence-Guzman, Maria F.,Berglund, Magnus,Skogvall, Staffan,Sterner, Olov
p. 2499 - 2512
(2008/09/21)

Silver nitrate-promoted ring enlargement of 1-tribromomethyl-1,2-dihydro- and 1-tribromomethyl-1,2,3,4-tetrahydro-isoquinoline derivatives: Application to the synthesis of the anti-anginal zatebradine
The one step AgNO3-mediated ring enlargement of 1-tribromomethyl-1,2-dihydro- and 1-tribromomethyl-1,2,3,4-tetrahydro-isoquinoline derivatives into 1,2-dihydro- and 1,2,3,4-tetrahydro-benzo[d]azepin-2-ones, respectively, is reported. This reaction offers a convenient entry to potentially active substances such as the anti-anginal zatebradine.
Pauvert, Micka?l,Collet, Sylvain,Guingant, André
p. 4203 - 4206
(2007/10/03)

Benzoxazine derivatives and their application in therapy
Compounds of the formula STR1 in which Y represents hydrogen, fluorine, chlorine, methyl or methoxy, R1 represents phenyl substituted by fluorine, methyl, methoxy, trifluoromethyl or phenyl, or R1 represents 2-thienyl, R2 represents methyl, and R3 represents (C1 -C4)-alkyl, or phenyl-(C1 -C2)-alkyl optionally substituted on the ring by 2 to 3 methoxy groups, or 2-(2-pyridyl)ethyl, or R2 and R3 form, with the adjacent nitrogen, 4-phenyl(1-piperidyl), 4-phenylmethyl(1-piperidyl), 1,2,3,4-tetrahydro-2-isoquinolyl, 6-methoxy-1,2,3,4-tetrahydro-2-isoquinolyl, 5,8-dimethoxy-1,2,3,4-tetrahydro-2-isoquinolyl, 6,7-dimethoxy 1,2,3,4-tetrahydro-2-isoquinolyl, 2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl, or 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl, and X represents carbonyl or sulphonyl, and their salts are useful as neuroprotective and antiiischaemic agents.
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(2008/06/13)

STUDIES ON m-CYCLOPHANE FORMATION FROM THE PHOTOLYSIS OF CHLOROACETAMIDE DERIVATIVES
The synthesis of 12-hydroxy-2-oxa-6-azabicyclotrideca-1(13),9,11-trien-5-one (4) is described.Two routes to (4) based on the photolysis of N-chloroacetamide (2b) and N-chloroacetamide (2c) followed by O-demethylation or O-desilylation, were developed.Extension of the work has given the new m-cyclophane ester derivative (9), whose structure has been confirmed by X-ray crystallography.
Rezaie, Robert,Bremner, John B.,Blanch, Gregory K.,Skelton, Brian W.,White, Allan H.
p. 959 - 972
(2007/10/02)

Tetrahydro-3-benzazepin-2-ones by lead tetraacetate oxidation of isoquinoline enamides: 7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one
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Lenz, George R.,Lessor, Ralph A.
p. 139 - 139
(2017/05/30)

(2H)-3-benzazepin-2-ones, their pharmaceutical compositions and their pharmaceutical uses
The invention relates to new heteroaromatic amine derivatives of formula STR1 wherein A represents a --CH2 --CH2 --, --CH=CH--or STR2 group and B represents a methylene, carbonyl or thiocarbonyl group or A represents a --CO--CO or STR3 group and B represents a methylene group, in which the carbon atom marked x is linked to the phenyl nucleus, E represents a straight-chained alkylene group optionally substituted by an alkyl group, G represents a straight-chained alkylene group optionally substituted by an alkyl group, R1 represents a hydrogen, fluorine, chlorine or bromine atom, a trifluoromethyl, nitro, amino, alkylamino, dialkylamino, alkyl, alkylmercapto, hydroxy, alkoxy or phenylalkoxy group, R2 represents a hydrogen, chlorine or bromine atom or a hydroxy, alkoxy, phenylalkoxy or alkyl group or R1 and R2 together represent an alkylenedioxy group, R3 represents a hydrogen atom, an alkenyl group, an alkyl or phenylalkyl group, and Het represents a 5- or 6-membered heteroaromtic ring bonded via a carbon or nitrogen atom, which contains an oxygen, sulphur or nitrogen atom, two nitrogen atoms or a nitrogen atom and an oxygen or sulphur atom, and onto which additionally a phenyl ring can be condensed, in which case the bond can also be via the phenyl nucleus, or an imidazo[1,2-a]pyridyl group wherein the carbon structure of the above-mentioned groups can be substituted by a methylenedioxy or ethylenedioxy group or can be mono- or disubstituted by a halogen atom or an alkyl, hydroxy, alkoxy, phenylalkoxy, phenyl, dimethoxyphenyl, nitro, amino, acetylamino, carbamoylamino, N-alkyl-carbamoylamino, hydroxymethyl, mercapto, alkylmercapto, alkylsulphinyl, alkylsulphonyl, alkylsulphonyloxy, alkylsulphonylamino, alkoxycarbonylmethoxy, carboxymethoxy or alkoxymethyl group, and at the same time any imino group present in the above-mentioned heteroaromatic groups can be substituted by an alkyl, phenylalkyl or phenyl group, the N-oxides and the acid addition salts thereof with inorganic or organic acids, which have valuable pharmacological properties, particularly the effect of lowering heart rate and oxygen requirement of the heart. They can be used to treat sinus tachycardia or ischaemic heart disease.
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(2008/06/13)

Aminotetralin derivatives
This invention related to new aminotetralin derivatives of formula I STR1 wherein STR2 B is methylene or, when A is --CH2 --CH2 --, --CH=CH--, --NH--CO-- or --CH2 --CO--, B can also be carbonyl or thiocarbonyl; E is a C2 -C4 straight-chain alkylene, optionally substituted by a C1 -C3 alkyl, or is 2-hydroxy-n-propylene, 2-hydroxy-n-butylene or 3-hydroxy-n-butylene; R1 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, nitro, amino, C1 -C3 alkylamino, C1 -C3 dialkylamino, C1 -C3 alkyl, C1 -C3 alkylthio, hydroxy, C1 -C3 alkoxy or phenyl C1 -C3 alkoxy; R2 is hydrogen, chlorine, bromine, hydroxy, C1 -C3 alkoxy phenyl C1 -C3 alkoxy, or C1 -C3 alkyl or, together with R1, can be a C1 -C2 alkylenedioxy; R3 and R4 are each independently selected from hydrogen, fluorine, chlorine, bromine, C1 -C3 alkyl, hydroxy, C1 -C3 alkoxy, nitro, amino, C1 -C3 alkylamino, or C1 -C3 dialkylamino, or together can be methylenedioxy; and R5 is hydrogen, C3 -C5 alkenyl, C1 -C3 alkyl, or phenyl C1 -C3 alkyl, and nontoxic, pharmaceutically acceptable addition salts thereof which have valuable pharmacological properties, particularly a long-lasting heart rate lowering effect and the effect of reducing the O2 requirement of the heart.
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(2008/06/13)

One-step Synthesis of the Erythrinane Skeleton by Acid-promoted Double Cyclization of N-(Cyclohex-1-enyl)-N--α-(mehylsulphinyl)acetamide and its Derivatives
On being heated with toluene-p-sulphonic acid, N-(cyclohex-1-enyl)-N--α-(methylsulphinyl)acetamide (8) underwent double cyclization to give the erythrinane derivative (11), which was converted into the amide (13) by reduction with Raney nickel and into the enamide (14) by thermolysis of the corresponding sulphoxide.The double cyclization of the sulphoxide (18) gave a stereoisomeric mixture of the ether products (19a) and (19b).On treatment with Raney nickel, either (19a) or (19b) afforded a mixture of the alcohols (20a) and (20b), each o f which was oxidized with chromium trioxide-pyridine to give the same ketone (21).The sulphoxide (25) also cyclized to afford two products (26) and (27), but in low yields, which were desulphurized with Raney nickel to give the erythrinones (28) and (29), respectively.
Ishibashi, Hiroyuki,Sato, Kazumi,Ikeda, Masazumi,Maeda, Hiroshi,Akai, Shuji,Tamura, Yasumitsu
p. 605 - 610
(2007/10/02)

Benzazepine derivatives, their pharmaceutical compositions and method of use
Compounds of the formula STR1 wherein A is --CH2 --CH2 --, --CH=CH--, --NH--CO--, --CH2 --CO-- or STR2 where R7 is alkyl of 1 to 3 carbon atoms, and B is methylene, carbonyl or thiocarbonyl, or A is --CO--CO--, --N=CH--, STR3 where R8 is hydrogen or alkyl of 1 to 3 carbon atoms substituted by a phenyl, methoxyphenyl or dimethoxyphenyl, and B is methylene; E is n-alkylene of 2 to 4 carbon atoms optionally substituted by an alkyl of 1 to 3 carbon atoms, 2-hydroxy-n-propylene, 2-hydroxy-n-butylene or 3-hydroxy-n-butylene; G is n-alkylene of 1 to 5 carbon atoms optionally substituted by an alkyl of 1 to 3 carbon atoms, wherein one methylene group of an n-alkylene of 2 to 5 carbon atoms can be replaced by a carbonyl group, with the proviso that B represents a methylene or carbonyl group, or methylene-n-hydroxy-alkylene of 1 to 4 carbon atoms, where the methylene group is attached to the nitrogen atom; and R1 to R5 are simple substituents of various types; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as bradycardiacs.
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(2008/06/13)

ACID-CATALYZED CYCLIZATIONS OF N-VINYL-α-SULFINYLACETAMIDES A NOVEL SYNTHETIC APPROACH TO ERYTHRINANE
Under the Pummerer reaction conditions, N-(1-cyclohexenyl)-N-methyl-α-(methylsulfinyl)acetamide (7a) cyclized in a 5-endo trigonal fashion through the intermediary cation (8) to give the tetrahydro-4H-oxindole (10).The reaction was successively applied to a novel synthesis of erythrinane skeleton.
Tamura, Y.,Maeda, H.,Akai, S.,Ishibashi, H.
p. 2209 - 2212
(2007/10/02)

6-PHENYL THIO- AND 6-CYCLOHEXYL THIO-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINES
Mercapto substituted-2,3,4,5-tetrahydro-1H-3-benzazepines having dopamine receptor blocking activity are prepared from o-quinones or via standard preparative procedures.
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(2008/06/13)