NL1013404C2 - Werkwijze voor de bereiding van een dipeptide en tussenproduct in een dergelijke werkwijze. - Google Patents

Werkwijze voor de bereiding van een dipeptide en tussenproduct in een dergelijke werkwijze. Download PDF

Info

Publication number: NL1013404C2
Authority: NL; Netherlands
Prior art keywords: leucine; tert; methylamide; formyl; leucyl
Prior art date: 1999-10-27

Application number

NL1013404A

Other languages

English (en)

Dutch (nl)

Inventor

Wilhelmus Hubertus Jos Boesten

Quirinus Bernardus Broxterman

Marcus Joseph Maria Plaum

Original Assignee

Dsm Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-10-27

Filing date

1999-10-27

Publication date

2001-05-01

1999-10-27 Priority to NL1013404A priority Critical patent/NL1013404C2/nl

1999-10-27 Application filed by Dsm Nv filed Critical Dsm Nv

2000-09-08 Priority to AT00963143T priority patent/ATE237632T1/de

2000-09-08 Priority to JP2001533158A priority patent/JP2003512476A/ja

2000-09-08 Priority to EP00963143A priority patent/EP1224211B1/en

2000-09-08 Priority to AU74593/00A priority patent/AU7459300A/en

2000-09-08 Priority to PCT/NL2000/000635 priority patent/WO2001030807A1/en

2000-09-08 Priority to CA002389024A priority patent/CA2389024A1/en

2000-09-08 Priority to HU0203284A priority patent/HUP0203284A3/hu

2000-09-08 Priority to CZ20021446A priority patent/CZ20021446A3/cs

2000-09-08 Priority to ES00963143T priority patent/ES2197115T3/es

2000-09-08 Priority to CN00814737.XA priority patent/CN1382155A/zh

2000-09-08 Priority to DE60002229T priority patent/DE60002229T2/de

2001-05-01 Application granted granted Critical

2001-05-01 Publication of NL1013404C2 publication Critical patent/NL1013404C2/nl

Links

238000000034 method Methods 0.000 title claims abstract description 23
238000002360 preparation method Methods 0.000 title claims abstract description 14
108010016626 Dipeptides Proteins 0.000 title claims abstract description 10
HFBHOAHFRNLZGN-LURJTMIESA-N (2s)-2-formamido-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC=O HFBHOAHFRNLZGN-LURJTMIESA-N 0.000 claims abstract description 11
238000002425 crystallisation Methods 0.000 claims abstract description 11
230000008025 crystallization Effects 0.000 claims abstract description 11
239000003814 drug Substances 0.000 claims abstract description 4
BPKJNEIOHOEWLO-UHFFFAOYSA-N 2-amino-n,3,3-trimethylbutanamide Chemical compound CNC(=O)C(N)C(C)(C)C BPKJNEIOHOEWLO-UHFFFAOYSA-N 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 7
-1 N-protected L-leucine Chemical class 0.000 claims description 6
125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 claims description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
239000012190 activator Substances 0.000 claims description 2
238000011835 investigation Methods 0.000 claims 1
230000003213 activating effect Effects 0.000 abstract description 4
239000003795 chemical substances by application Substances 0.000 abstract description 3
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 12
229940011051 isopropyl acetate Drugs 0.000 description 12
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000004395 L-leucine Substances 0.000 description 7
125000000217 alkyl group Chemical group 0.000 description 7
229960003136 leucine Drugs 0.000 description 7
235000019454 L-leucine Nutrition 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
230000004913 activation Effects 0.000 description 6
230000008878 coupling Effects 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
229940024606 amino acid Drugs 0.000 description 5
150000001413 amino acids Chemical class 0.000 description 5
239000012634 fragment Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
230000006340 racemization Effects 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
125000001072 heteroaryl group Chemical group 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 3
FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 3
OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000005897 peptide coupling reaction Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
LIBDTAYIDBPBRN-LURJTMIESA-N (2s)-2-amino-n,4-dimethylpentanamide Chemical compound CNC(=O)[C@@H](N)CC(C)C LIBDTAYIDBPBRN-LURJTMIESA-N 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
230000006198 deformylation Effects 0.000 description 2
238000006344 deformylation reaction Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
239000000725 suspension Substances 0.000 description 2
GRDXOXRGSKKLNH-SCSAIBSYSA-N (4s)-4-tert-butyl-1,3-oxazolidine-2,5-dione Chemical compound CC(C)(C)[C@@H]1NC(=O)OC1=O GRDXOXRGSKKLNH-SCSAIBSYSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
125000001433 C-terminal amino-acid group Chemical group 0.000 description 1
101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
150000003862 amino acid derivatives Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
239000000047 product Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06043—Leu-amino acid

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Life Sciences & Earth Sciences (AREA)
Peptides Or Proteins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

NL1013404A 1999-10-27 1999-10-27 Werkwijze voor de bereiding van een dipeptide en tussenproduct in een dergelijke werkwijze. NL1013404C2 (nl)

Priority Applications (12)

Application Number	Priority Date	Filing Date	Title
NL1013404A NL1013404C2 (nl)	1999-10-27	1999-10-27	Werkwijze voor de bereiding van een dipeptide en tussenproduct in een dergelijke werkwijze.
JP2001533158A JP2003512476A (ja)	1999-10-27	2000-09-08	ジペプチドの製造法および該方法における中間生成物
EP00963143A EP1224211B1 (en)	1999-10-27	2000-09-08	Process for the preparation of a dipeptide and intermediate product in such a process
AU74593/00A AU7459300A (en)	1999-10-27	2000-09-08	Process for the preparation of a dipeptide and intermediate product in such a process
AT00963143T ATE237632T1 (de)	1999-10-27	2000-09-08	Verfahren zur herstellung eines dipeptids und zwischenverbindung bei diesem verfahren
PCT/NL2000/000635 WO2001030807A1 (en)	1999-10-27	2000-09-08	Process for the preparation of a dipeptide and intermediate product in such a process
CA002389024A CA2389024A1 (en)	1999-10-27	2000-09-08	Process for the preparation of a dipeptide and intermediate product in such a process
HU0203284A HUP0203284A3 (en)	1999-10-27	2000-09-08	Process for the preparation of a dipeptide and intermediate product in such a process
CZ20021446A CZ20021446A3 (cs)	1999-10-27	2000-09-08	Způsob výroby dipeptidu, meziprodukt vzniklý při tomto způsobu a jeho pouľití při výrobě léčiv
ES00963143T ES2197115T3 (es)	1999-10-27	2000-09-08	Procedimiento para la preparacion de un dipeptido y producto intermedio en dicho procedimiento.
CN00814737.XA CN1382155A (zh)	1999-10-27	2000-09-08	制备二肽的方法以及该方法的中间产物
DE60002229T DE60002229T2 (de)	1999-10-27	2000-09-08	Verfahren zur herstellung eines dipeptids und zwischenverbindung bei diesem verfahren

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL1013404A NL1013404C2 (nl)	1999-10-27	1999-10-27	Werkwijze voor de bereiding van een dipeptide en tussenproduct in een dergelijke werkwijze.
NL1013404		1999-10-27

Publications (1)

Publication Number	Publication Date
NL1013404C2 true NL1013404C2 (nl)	2001-05-01

Family

ID=19770139

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1013404A NL1013404C2 (nl)	1999-10-27	1999-10-27	Werkwijze voor de bereiding van een dipeptide en tussenproduct in een dergelijke werkwijze.

Country Status (12)

Country	Link
EP (1)	EP1224211B1 (cs)
JP (1)	JP2003512476A (cs)
CN (1)	CN1382155A (cs)
AT (1)	ATE237632T1 (cs)
AU (1)	AU7459300A (cs)
CA (1)	CA2389024A1 (cs)
CZ (1)	CZ20021446A3 (cs)
DE (1)	DE60002229T2 (cs)
ES (1)	ES2197115T3 (cs)
HU (1)	HUP0203284A3 (cs)
NL (1)	NL1013404C2 (cs)
WO (1)	WO2001030807A1 (cs)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1996011209A1 (en) *	1994-10-05	1996-04-18	Chiroscience Limited	Peptidyl compounds and their therapeutic use as inhibitors of metalloproteases
WO1997012902A1 (en) *	1995-10-05	1997-04-10	Darwin Discovery Limited	Thio-substituted peptides as inhibitors for metalloproteinases and tnf liberation

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0680075B2 (ja) *	1985-12-24	1994-10-12	味の素株式会社	Ｎ―ホルミル―α―Ｌ―アスパルチル―Ｌ―フェニルアラニンメチルエステルの製造法

1999
- 1999-10-27 NL NL1013404A patent/NL1013404C2/nl not_active IP Right Cessation
2000
- 2000-09-08 CZ CZ20021446A patent/CZ20021446A3/cs unknown
- 2000-09-08 JP JP2001533158A patent/JP2003512476A/ja active Pending
- 2000-09-08 AT AT00963143T patent/ATE237632T1/de not_active IP Right Cessation
- 2000-09-08 WO PCT/NL2000/000635 patent/WO2001030807A1/en not_active Ceased
- 2000-09-08 AU AU74593/00A patent/AU7459300A/en not_active Abandoned
- 2000-09-08 CA CA002389024A patent/CA2389024A1/en not_active Abandoned
- 2000-09-08 HU HU0203284A patent/HUP0203284A3/hu unknown
- 2000-09-08 DE DE60002229T patent/DE60002229T2/de not_active Expired - Fee Related
- 2000-09-08 EP EP00963143A patent/EP1224211B1/en not_active Expired - Lifetime
- 2000-09-08 CN CN00814737.XA patent/CN1382155A/zh active Pending
- 2000-09-08 ES ES00963143T patent/ES2197115T3/es not_active Expired - Lifetime

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1996011209A1 (en) *	1994-10-05	1996-04-18	Chiroscience Limited	Peptidyl compounds and their therapeutic use as inhibitors of metalloproteases
WO1997012902A1 (en) *	1995-10-05	1997-04-10	Darwin Discovery Limited	Thio-substituted peptides as inhibitors for metalloproteinases and tnf liberation

Also Published As

Publication number	Publication date
CA2389024A1 (en)	2001-05-03
HUP0203284A3 (en)	2003-12-29
EP1224211B1 (en)	2003-04-16
CN1382155A (zh)	2002-11-27
ATE237632T1 (de)	2003-05-15
ES2197115T3 (es)	2004-01-01
WO2001030807A1 (en)	2001-05-03
AU7459300A (en)	2001-05-08
DE60002229D1 (de)	2003-05-22
CZ20021446A3 (cs)	2002-10-16
DE60002229T2 (de)	2004-03-25
EP1224211A1 (en)	2002-07-24
JP2003512476A (ja)	2003-04-02
HUP0203284A2 (hu)	2003-02-28

Legal Events

Date	Code	Title	Description
2001-07-02	PD2B	A search report has been drawn up
2005-07-01	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20050501

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CA1270098A (en)	1990-06-05	Acyltripeptide immunostimulants
RU2007396C1 (ru)	1994-02-15	Способ получения n-карбоксиангидридов или n-тиокарбоксиангидридов уретанзащищенных аминокислот
JP2000256397A (ja)	2000-09-19	新規な環状テトラペプチド誘導体とその医薬用途
JPS6253952A (ja)	1987-03-09	レニン阻害剤製造用中間体の立体選択的製法
EP0253190B1 (en)	1992-12-30	Partially retro-inverted tuftsin analogues, method for the preparation thereof and pharmaceutical compositions containing them
Wu et al.	1993	An Efficient Method for The Preparation of w, w′-bis-Urethane Protected Arginine Derivatives
US6184345B1 (en)	2001-02-06	Branched building units for synthesizing cyclic peptides
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