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1. (WO2014202765) PREPARATION OF CHIRAL 1-METHYL-2,3,4,5-1H-BENZODIAZEPINES VIA ASYMMETRIC REDUCTION OF ALPHA-SUBSTITUTED STYRENES
Latest bibliographic data on file with the International Bureau   

Pub. No.: WO/2014/202765 International Application No.: PCT/EP2014/063048
Publication Date: 24.12.2014 International Filing Date: 20.06.2014
IPC:
C07D 223/16 (2006.01) ,C07C 67/03 (2006.01) ,C07C 69/635 (2006.01) ,C07C 201/12 (2006.01) ,C07C 205/09 (2006.01) ,C07C 209/34 (2006.01) ,C07C 209/48 (2006.01) ,C07C 211/29 (2006.01) ,C07C 217/40 (2006.01) ,C07C 233/18 (2006.01) ,C07C 253/30 (2006.01) ,C07C 255/10 (2006.01) ,C07C 311/17 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
223
Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
14
condensed with carbocyclic rings or ring systems
16
Benzazepines; Hydrogenated benzazepines
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
67
Preparation of carboxylic acid esters
03
by reacting an ester group with a hydroxy group
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
69
Esters of carboxylic acids; Esters of carbonic or haloformic acids
62
Halogen-containing esters
63
of saturated acids
635
containing rings in the acid moiety
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
201
Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
06
Preparation of nitro compounds
12
by reactions not involving the formation of nitro groups
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
205
Compounds containing nitro groups bound to a carbon skeleton
07
the carbon skeleton being further substituted by halogen atoms
08
having nitro groups bound to acyclic carbon atoms
09
of an unsaturated carbon skeleton
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
209
Preparation of compounds containing amino groups bound to a carbon skeleton
30
by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
32
by reduction of nitro groups
34
by reduction of nitro groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
209
Preparation of compounds containing amino groups bound to a carbon skeleton
44
by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
48
by reduction of nitriles
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
211
Compounds containing amino groups bound to a carbon skeleton
01
having amino groups bound to acyclic carbon atoms
26
of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
29
the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
217
Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
02
having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
04
the carbon skeleton being acyclic and saturated
28
having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
40
having at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the same carbon atom of the carbon skeleton, e.g. amino-ketals, ortho esters
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
233
Carboxylic acid amides
01
having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
16
having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
17
with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
18
having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
253
Preparation of carboxylic acid nitriles
30
by reactions not involving the formation of cyano groups
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
255
Carboxylic acid nitriles
01
having cyano groups bound to acyclic carbon atoms
10
containing cyano groups and halogen atoms, or nitro or nitroso groups, bound to the same acyclic carbon skeleton
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
311
Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
15
Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
16
having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
17
to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Applicants: LEK PHARMACEUTICALS D.D.[SI/SI]; Verovskova 57 1526 Ljubljana, SI
Inventors: STAVBER, Gaj; SI
GAZIC SMILOVIC, Ivana; SI
CLUZEAU, Jerome; SI
RICHTER, Frank; AT
Agent: KLUSCHANZOFF, Harald; Industriestr. 25 83607 Holzkirchen, DE
Priority Data:
13173237.221.06.2013EP
Title (EN) PREPARATION OF CHIRAL 1-METHYL-2,3,4,5-1H-BENZODIAZEPINES VIA ASYMMETRIC REDUCTION OF ALPHA-SUBSTITUTED STYRENES
(FR) PRÉPARATION DE 1-MÉTHYL-2,3,4,5-1H-BENZODIAZÉPINES CHIRALES PAR RÉDUCTION ASYMÉTRIQUE DE STYRÈNES ALPHA-SUBST ITUÉS
Abstract:
(EN) The present invention provides an asymmetric and economic synthesis of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine via novel intermediates applying an asymmetric enzymatic, biomimetic or catalytic reduction. The present invention also provides a novel green asymmetric catalytic reduction adapted for an aqueous medium to be applied in the synthesis of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1 H-benzo[d]azepine or novel intermediates.
(FR) La présente invention concerne une synthèse asymétrique et économique de 8-chloro-1-méthyl-2,3,4,5-tétrahydro-1H-benzo[d]azépine par de nouveaux intermédiaires appliquant une réduction enzymatique, biomimétique ou catalytique asymétrique. La présente invention concerne également une nouvelle réduction catalytique asymétrique verte adaptée pour un milieu aqueux devant être appliqué dans la synthèse de 8-chloro-1-méthyl-2,3,4,5-tétrahydro-1H-benzo[d]azépine ou de nouveaux intermédiaires.
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Designated States: AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
African Regional Intellectual Property Organization (ARIPO) (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Office (AM, AZ, BY, KG, KZ, RU, TJ, TM)
European Patent Office (EPO) (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)