EP0478787B1
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Novel process for producing benzoic acid derivative
Assignee: Shionogi and Co Ltd
•
Filing: 1991-03-15
•
Granted: 1994-12-21
•
Expires: 2011-03-15
Abstract
Abstract Prepn. of a benzoic acid of formula (V) comprises (a) subjecting an acetanilide of formula (I) and a 1,4-dihalobutane deriv. of formula (II) to a Friedel-Crafts reaction to give a 1,2,3,4-tetrahydro-6-amido- naphthalene cpd. of formula (III); (b) reacting (III) with a monoester halide of terephthalic acid to give a benzoic acid ester of formula (IV); and (c) hydrolysing (IV). R1 = lower alkyl or aryl; R2 = H or lower alkyl; R3-R6 = lower alkyl; R7 = H or lower alkyl; X = halo; R8 = lower alkyl; R9 = H or lower alkyl. - Also claimed is 4-((5,6,7,8-tetra hydro-5,5,8,8- tetramethyl-2-naphthalenyl) carbamoyl benzoic acid with a X-ray diffraction pattern given in the claims.
Inventors
- 👤 Yoshinori Hamada
- 👤 Isamu Yamada
- 👤 Masaaki Uenaka
- 👤 Teruo Sakata
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-30 21:07
CPC Classifications
A; A61; A61K; A61K9/00; A61K9/10; A61K9/127; A61K9/1271; A61P; A61P3/00; C; C07; C07C; C07C231/00; C07C231/12; C07C231/14; C07C233/00; C07C233/01; C07C233/02; C07C233/04; C07C233/07; C07C233/64; C07C233/65; C07C2602/00; C07C2602/02; C07C2602/04; C07C2602/10
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
178 words
A method for preparing a benzoic acid derivative of the general formula (V): wherein R², R⁷ and R⁹ are independently hydrogen or lower alkyl, and R³, R⁴, R⁵ and R⁶ are independently lower alkyl, which comprises: (a) subjecting acyl aniline derivative of the general formula (I): wherein R¹ is lower alkyl or aryl and R² is the same as above, and 1,4-butyl dihalide derivative (II): wherein R³, R⁴, R⁵, R⁶, and R⁷ are respectively the same as above, and X is halogen, to Friedel-Crafts reaction to give a bicyclic amide compound of the general formula (III): wherein R¹, R², R³, R⁴, R⁵, R⁶, and R⁷ are respectively the same as above: (b) reacting the compound (III) obtained in the step (a) with a monoester terephthalic halide to form a compound of the general formula (IV): wherein R², R³, R⁴, R⁵, R⁶, R⁷, and R⁹ are respectively the same as above, and R⁸ is lower alkyl; and (c) subjecting the compound (IV) obtained in the step (b) to deesterification reaction to give the compound of the general formula (V).
Claim 2
Dependent Claim
24 words
A bicyclic amide compound of the general formula (III): wherein R¹, R², R³, R⁴, R⁵, R⁶, and R⁷ are respectively the same as above.
Claim 3
Dependent Claim
95 words
A crystal form of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbamoyl]benzoic acid which exhibits the angles and strength ratios of X-ray diffraction shown in the table below: 2ϑ Intensity ratio 2ϑ Intensity ratio 6.58 2685 23.94 677 7.84 455 26.14 335 9.80 177 26.84 248 11.90 664 26.96 310 13.24 10000 27.16 469 15.74 1558 27.8 448 16.02 1671 28.34 332 16.80 871 28.76 1552 17.52 213 29.18 202 17.76 1069 30.2 192 18.1 4112 31.66 429 19.5 2685 31.82 213 19.86 924 33.96 166 20.56 256 35.56 227 21.54 1385 35.78 158 22.08 1326 38.04 237 22.48 987 38.28 771
Claim 4
Dependent Claim
28 words
A method for preparing a crystalline 4-[(5,6,7,8-tetrahydro-5,5, 8,8-tetramethyl-2-naphthyl)carbamoyl]benzoic acid claimed in claim 3 comprising the step of recrystallizing a compound of the formula: from a methanol type solvent.
Claim 5
Dependent Claim
91 words
A method for preparing a bicyclic amide compound of the general formula (III): wherein R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are the same as in claim 1, which comprises subjecting an acyl aniline derivative of the general formula (I): wherein R¹ and R² are the same as above, and a 1,4-butyl dihalide derivative of the general formula (II): wherein R³, R⁴, R⁵, R⁶ and R⁷ are the same as above, and X is halogen, to a Friedel-Crafts reaction in an inert solvent in the presence of a Friedel-Crafts catalyst.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
Maintenance schedule is calculated for granted US utility patents.