WO2009000397A1 - Verfahren zur herstellung von pentahydroxyhexylcarbamoylundekansäurebenzylester - Google Patents
Verfahren zur herstellung von pentahydroxyhexylcarbamoylundekansäurebenzylester Download PDFInfo
- Publication number
- WO2009000397A1 WO2009000397A1 PCT/EP2008/004552 EP2008004552W WO2009000397A1 WO 2009000397 A1 WO2009000397 A1 WO 2009000397A1 EP 2008004552 W EP2008004552 W EP 2008004552W WO 2009000397 A1 WO2009000397 A1 WO 2009000397A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- compound
- iso
- butyloxy
- meaning
- Prior art date
Links
- KVISOLHONBWYED-UHFFFAOYSA-O OCC(C(C(C(C[NH2+]C(CCCCCCCCCCC(OCc1ccccc1)=O)=O)O)O)O)N=O Chemical compound OCC(C(C(C(C[NH2+]C(CCCCCCCCCCC(OCc1ccccc1)=O)=O)O)O)O)N=O KVISOLHONBWYED-UHFFFAOYSA-O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
Definitions
- the invention relates to an improved process for the preparation of Pentahydroxyhexylcarbamoylundekanklarebenzylester
- Pentahydroxyhexylcarbamoyl undekan Acidbenzylester has the formula I.
- the compound of formula III which is described in US 7,205,290.
- the compound of formula III can be used, for example, as a cholesterol-lowering agent.
- HOBt 1-hydroxybenzotriazole
- EDC N- (3-dimethylaminopropyl) -N'-ethylcarbodiimide hydrochloride
- the object of the present invention was now to provide an improved process for the preparation of the compound of the formula I, which does not have the abovementioned disadvantages.
- the improved process should also enable a preparation of the compound of the formula I in a large-scale production process.
- the process to the most economical conditions, that can be carried out inexpensively.
- the object is achieved by production method A)
- Preferred compounds of the formula VI are alkyl acid halides and haloformic acid alkyl esters, particularly preferably isobutyl chloroformate.
- alkyl radical is meant a straight or branched hydrocarbon chain of one to eighteen carbons, e.g. Methyl, ethyl, iso -propyl, n-butyl, i-butyl, tert -butyl, hexyl, heptyl, octyl.
- Hal is understood to mean a halogen radical which may have the meaning Br, Cl or J.
- An aryl radical is understood as meaning a phenyl, naphthyl or biphenyl radical in which one or more CH groups can be replaced by O, N or S.
- the aryl radicals can be monosubstituted or polysubstituted by suitable groups, such as, for example: F, Cl, Br, I, CF 3 , NO 2 , CN, COO (C 1 -C 6 ) alkyl, CON [(C, -C 6 ) AlkyI] 2, cycloalkyl, (C, -C, 0) alkyl, (C 2 -C 6) - alkenyl, (C 2 -C 6) -alkynyl, O- (C, -C6) alkyl, 0 - (C 2 -C 6 ) -alkenyl, O- (C 2 -C 6 ) -alkynyl, O-CO- (dC 6 ) -alkyl, O-CO- (C, -C 6 ) -aryl, 0- CO- (C 1 -C 6 ) -heterocycle, SO 2 N [(C 1 -C 6 )
- step a) Dodekandikladobenzylester in a suitable solvent in the presence of a suitable base at -30 0 C to + 70 ° C, preferably at -10 0 C to + 40 0 C, particularly preferably at -5 0 C to 0 0 C dissolved and within 30 - 150 minutes, preferably 60-120 minutes to a -10 ° C to 3O 0 C, preferably -10 0 C to 0 0 C cooled solution of compound VI, particularly preferably isobutyl chloroformate, added.
- reaction mixture can now either be used directly in the subsequent reaction, or the product formed is isolated. Preferably, the reaction mixture is used directly.
- the solvent is evaporated in vacuo.
- the reaction mixture is washed with water before evaporation of the solvent.
- Suitable bases are exemplified by tertiary amines such as triethylamine, ethyldimethylamine, ethyldiisopropylamine, tributylamine, N-ethylmorpholine, tetramethylethylenediamine, guanidine or alkylguanidines, particularly preferred are triethylamine or ethyldiisopropylamine.
- Suitable solvents are, for example, conventional aprotic organic solvents such as, for example, toluene, chlorobenzene, dichloromethane, ethyl acetate, butyl acetate, diisobutyl ether, diisopropyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, dimethylformamide, N-methylpyrrolidone or methyl ethyl ketone; particularly preferred are ethyl acetate or butyl acetate.
- conventional aprotic organic solvents such as, for example, toluene, chlorobenzene, dichloromethane, ethyl acetate, butyl acetate, diisobutyl ether, diisopropyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, dimethylformamide, N-methylpyrrolidone or methyl ethyl ketone; particularly preferred are
- step b) within 5 to 60 minutes, preferably 15-30 minutes, D-glucamine is added in portions to a solution of product V (prepared as described above, either reaction solution directly or the isolated product dissolved in a suitable solvent) and optionally one suitable base in a suitable solvent at -10 ° C to 4O 0 C, preferably -5 ° C to 0 0 C added.
- Suitable bases are exemplified by tertiary amines such as triethylamine, ethyldimethylamine, ethyldiisopropylamine, tributylamine, N-ethylmorpholine (NEM), tetramethylethylenediamine, guanidine or alkylguanidines, particularly preferred are triethylamine or ethyldiisopropylamine (Hünig's base).
- tertiary amines such as triethylamine, ethyldimethylamine, ethyldiisopropylamine, tributylamine, N-ethylmorpholine (NEM), tetramethylethylenediamine, guanidine or alkylguanidines, particularly preferred are triethylamine or ethyldiisopropylamine (Hünig's base).
- Suitable solvents are, for example, customary aprotic organic solvents such as, for example, toluene, chlorobenzene, dichloromethane, ethyl acetate, butyl acetate, diisobutyl ether, diisopropyl ether, tetrahydrofuran, 2-methyltertrahydrofuran.
- Dimethylformamide, N-methylpyrrolidone or methyl ethyl ketone particularly preferred are ethyl acetate or butyl acetate.
- the reaction mixture is stirred for 5 to 120 minutes, preferably 30 to 60 minutes at -10 0 C to 40 ° C, preferably at -5 ° C to 0 0 C, followed by another 5 to 20 hours, preferably 12 hours at 0 to 30 0 C. , Preferably 15 ° C to 2O 0 C, and then washed with water at 10 0 C - 80 0 C, preferably at 50 0 C - 70 0 C washed out. In the subsequent cooling to 20 0 C, the product of the formula I.
- Another aspect of this invention is an alternative manufacturing process B)
- step a) dodecanedioic acid monobenzyl ester is dissolved in a suitable solvent in the presence of a suitable base at -30 ° C to + 70 ° C, preferably at -10 ° C to + 40 0 C, more preferably at -5 ° C to O 0 C. and within 30 to 150 minutes, preferably 60-120 minutes to a -10 to 0 C to 30 0 C, preferably -10 ° C cooled to 0 ° C solution of compound VI, particularly preferably isobutyl chloroformate, is metered in.
- a suitable base at -30 ° C to + 70 ° C, preferably at -10 ° C to + 40 0 C, more preferably at -5 ° C to O 0 C. and within 30 to 150 minutes, preferably 60-120 minutes to a -10 to 0 C to 30 0 C, preferably -10 ° C cooled to 0 ° C solution of compound VI, particularly preferably isobutyl chloroformate,
- a to -10 0 C to 30 0 C, preferably -10 0 C to 0 0 C cooled solution of compound VI, preferably butyl chloroformate, are initially charged in a suitable solvent and then Dodekandikladobenzylester and a suitable base in a suitable solvent at -30 0 C to +70 0 C, vozugêt at -10 0 C to +40 0 C, more preferably at -5 to 0 C 0 0 C within 30-150 minutes, preferably 60-120 minutes are added.
- the reaction mixture is stirred at -10 0 C to 40 0 C, preferably at -10 0 C to 0 0 C for 15 to 150 minutes, preferably 30 - 120 minutes.
- the reaction gypsum can now either be used directly in the subsequent reaction, or the product formed is isolated.
- the reaction mixture is used directly.
- the solvent is evaporated in vacuo.
- the reaction mixture is washed with water prior to evaporation of the solvent.
- Suitable bases are, for example, tertiary amines such as, for example, triethylamine, ethyldimethylamine, ethyldiisopropylamine, tributylamine, N-ethylmorpholine, Tetramethylethylenediamine, guanidine or alkylguanidines, particularly preferred are triethylamine or ethyldiisopropylamine.
- Suitable solvents are, for example, conventional aprotic organic solvents such as, for example, toluene, chlorobenzene, dichloromethane, ethyl acetate, butyl acetate, diisobutyl ether, diisopropyl ether, tetrahydrofuran, 2-methyltertrahydrofuran, dimethylformamide, N-methylpyrrolidone or methyl ethyl ketone; particularly preferred are ethyl acetate or butyl acetate.
- conventional aprotic organic solvents such as, for example, toluene, chlorobenzene, dichloromethane, ethyl acetate, butyl acetate, diisobutyl ether, diisopropyl ether, tetrahydrofuran, 2-methyltertrahydrofuran, dimethylformamide, N-methylpyrrolidone or methyl ethyl ketone; particularly preferred are eth
- step b) is within 5 to 60 minutes, preferably 15-30 minutes
- Dodecanedioic acid monobenzyl ester of formula IV in portions to a solution of product V (prepared as described above, either use reaction solution directly or isolate the isolated product in a suitable solvent) and optionally a suitable base in a suitable solvent at -10 ° C to 40 ° C, preferably 0 0 C to 25 ° C added.
- Suitable bases are exemplified by tertiary amines such as triethylamine, ethyldimethylamine, ethyldiisopropylamine, tributylamine, N-ethylmorpholine, tetramethylethylenediamine, guanidine or alkylguanidines, particularly preferred are triethylamine or ethyldiisopropylamine.
- Suitable solvents are, for example, conventional aprotic organic solvents such as, for example, toluene, chlorobenzene, dichloromethane, ethyl acetate, butyl acetate, diisobutyl ether, diisopropyl ether, tetrahydrofuran, 2-methyltertrahydrofuran, dimethylformamide, N-methylpyrrolidone or methyl ethyl ketone; particularly preferred are ethyl acetate or butyl acetate.
- the reaction mixture is stirred for 5 to 240 minutes, preferably 60 to 150 minutes at -10 ° C to 40 ° C, preferably at 0 0 C to 25 ° C.
- the resulting precipitate is filtered off and dried to give product of formula VIII
- step c) within 5 to 60 minutes, preferably 15-30 minutes, D-glucamine is added in portions to a solution of product VIII and optionally a suitable base in a suitable solvent at -10 ° C to 40 ° C, preferably -5 ° C added to 5 ° C.
- Suitable bases are, for example, tertiary amines such as, for example, triethylamine, ethyldimethylamine, ethyldiisopropylamine, tributylamine, N-ethylmorpholine, Tetramethylethylenediamine, guanidine or alkylguanidines, particularly preferred are triethylamine or ethyldiisopropylamine.
- Suitable solvents are, for example, conventional aprotic organic solvents such as, for example, toluene, chlorobenzene, dichloromethane, ethyl acetate, butyl acetate, diisobutyl ether, diisopropyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, dimethylformamide, N-methylpyrrolidone or methyl ethyl ketone; particularly preferred are ethyl acetate or butyl acetate.
- conventional aprotic organic solvents such as, for example, toluene, chlorobenzene, dichloromethane, ethyl acetate, butyl acetate, diisobutyl ether, diisopropyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, dimethylformamide, N-methylpyrrolidone or methyl ethyl ketone; particularly preferred are
- the reaction mixture is stirred for 1 to 20 hours, preferably 10 to 18 hours at -10 ° C to 40 ° C, preferably at 10 ° C to 25 ° C and then with water at 10 0 C - 80 0 C, preferably at 50 ° C - 70 0 C washed out.
- the product of formula I In the subsequent cooling to 20 ° C, the product of formula I.
- the compound of formula I is converted by cleavage of the benzyl protecting group, for example by saponification of the ester under alkaline conditions or by hydrogenation of the ester, in the compound of formula II and then
- Suitable peptide coupling reagents and solvents or solubilizing agents are described inter alia in, for example, A. Speicher et al., Journal of Practical Chemistry / Chemiker-Zeitung (1998), 340, 581-583; YS Klausner and M. Bodansky, Synthesis, (1972), 453 ff; K. Ishihara et al., J. Org. Chem., 61, 4196 (1996); Kunishima et al., Tetrahedron 55, 13159-13170 (1999) or RC Larock: Comprehensive Organic Transformations; VCH, New York, 1989, page 981 et seq.
- reaction of the compound of formula II with the amine of formula VII is e.g. in WO 02/50027 or US Pat. No. 7,205,290.
- a further aspect of the invention is the novel compound of formula Va.
- a further aspect of the invention is the novel compound of formula VIII.
- the H-isobutoxycarbonyloxy-n-oxo-dodecanoic acid benzyl ester prepared according to 1. is dissolved in 15 ml of ethyl acetate and treated at 0.degree. C. with 0.9 g (5.2 mmol) of 2R, 3R, 4R, 5S-6-amino- hexane-1,2,3,4,5-pentanol (D-glucamine). The mixture is stirred for one hour at 0 0 C, heated to 20 0 C and allowed to stand overnight. The resulting white suspension is shaken out at 65 ° C. three times with 20 ml of water at the same temperature. The organic phase is then concentrated to dryness. A colorless solid is obtained in a yield of 92.9%.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2008267515A AU2008267515A1 (en) | 2007-06-22 | 2008-06-07 | Process for preparing benzyl pentahydroxyhexylcarbamoylundecanoate |
CN200880021496A CN101687769A (zh) | 2007-06-22 | 2008-06-07 | 用于制备五羟基己基氨基甲酰十一酸苯甲酯的工艺方法 |
CA2691065A CA2691065A1 (en) | 2007-06-22 | 2008-06-07 | Process for preparing benzyl pentahydroxyhexylcarbamoylundecanoate |
BRPI0813120A BRPI0813120A2 (pt) | 2007-06-22 | 2008-06-07 | processo para preparar penta -hidróxi-hexilcarbamoilundecanoato de benzila |
MX2009012727A MX2009012727A (es) | 2007-06-22 | 2008-06-07 | Procedimiento para preparar pentahidroxihexilcar-bamoilundecanoato de bencilo. |
IL202824A IL202824A0 (en) | 2007-06-22 | 2009-12-17 | Process for preparing benzyl pentahydroxyhexylcarbamoylundecanoate |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/767,284 US20080319218A1 (en) | 2007-06-22 | 2007-06-22 | Processes for Making and Using Benzyl Pentahydroxyhexylcarbamoylundecanoate |
US11/767,284 | 2007-06-22 | ||
US11/767,298 | 2007-06-22 | ||
US11/767,298 US20080319221A1 (en) | 2007-06-22 | 2007-06-22 | Esters of Pentahydroxyhexylcarbamoyl Alkanoic Acids |
DE102007029612.8 | 2007-06-27 | ||
DE102007029612A DE102007029612A1 (de) | 2007-06-27 | 2007-06-27 | Verfahren zur Herstellung von Pentahydroxyhexylcarbamoylundekan- säurebenzylester |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2009000397A1 true WO2009000397A1 (de) | 2008-12-31 |
Family
ID=39695874
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2008/004552 WO2009000397A1 (de) | 2007-06-22 | 2008-06-07 | Verfahren zur herstellung von pentahydroxyhexylcarbamoylundekansäurebenzylester |
Country Status (12)
Country | Link |
---|---|
KR (1) | KR20100023886A (de) |
CN (1) | CN101687769A (de) |
AR (1) | AR068977A1 (de) |
AU (1) | AU2008267515A1 (de) |
BR (1) | BRPI0813120A2 (de) |
CA (1) | CA2691065A1 (de) |
CL (1) | CL2008001857A1 (de) |
IL (1) | IL202824A0 (de) |
MX (1) | MX2009012727A (de) |
TW (1) | TW200914406A (de) |
UY (1) | UY31165A1 (de) |
WO (1) | WO2009000397A1 (de) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09117279A (ja) * | 1995-10-25 | 1997-05-06 | Samu Kenkyusho:Kk | レシチン化スーパーオキシドディスムターゼおよびそれを有効成分とする医薬 |
US7067689B1 (en) * | 2005-07-08 | 2006-06-27 | Microbia, Inc. | Process for production of pentahydroxyhexylcarbamoyl alkanoic acids |
-
2008
- 2008-06-07 AU AU2008267515A patent/AU2008267515A1/en not_active Abandoned
- 2008-06-07 MX MX2009012727A patent/MX2009012727A/es not_active Application Discontinuation
- 2008-06-07 CN CN200880021496A patent/CN101687769A/zh active Pending
- 2008-06-07 WO PCT/EP2008/004552 patent/WO2009000397A1/de active Application Filing
- 2008-06-07 CA CA2691065A patent/CA2691065A1/en not_active Abandoned
- 2008-06-07 KR KR1020097026689A patent/KR20100023886A/ko not_active Application Discontinuation
- 2008-06-07 BR BRPI0813120A patent/BRPI0813120A2/pt not_active Application Discontinuation
- 2008-06-19 AR ARP080102606A patent/AR068977A1/es unknown
- 2008-06-19 TW TW097122784A patent/TW200914406A/zh unknown
- 2008-06-20 UY UY31165A patent/UY31165A1/es unknown
- 2008-06-20 CL CL200801857A patent/CL2008001857A1/es unknown
-
2009
- 2009-12-17 IL IL202824A patent/IL202824A0/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09117279A (ja) * | 1995-10-25 | 1997-05-06 | Samu Kenkyusho:Kk | レシチン化スーパーオキシドディスムターゼおよびそれを有効成分とする医薬 |
US7067689B1 (en) * | 2005-07-08 | 2006-06-27 | Microbia, Inc. | Process for production of pentahydroxyhexylcarbamoyl alkanoic acids |
Non-Patent Citations (1)
Title |
---|
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; MIZUSHIMA, HIROSHI ET AL: "Lecithinized human Cu-Zn type superoxide dismutase (h-SOD) with improved pharmacological activities", XP002493287, retrieved from STN Database accession no. 1997:335273 * |
Also Published As
Publication number | Publication date |
---|---|
UY31165A1 (es) | 2009-01-30 |
MX2009012727A (es) | 2009-12-08 |
AR068977A1 (es) | 2009-12-23 |
BRPI0813120A2 (pt) | 2019-09-10 |
TW200914406A (en) | 2009-04-01 |
AU2008267515A1 (en) | 2008-12-31 |
KR20100023886A (ko) | 2010-03-04 |
CA2691065A1 (en) | 2008-12-31 |
IL202824A0 (en) | 2010-06-30 |
CL2008001857A1 (es) | 2008-10-10 |
CN101687769A (zh) | 2010-03-31 |
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