NL1007113C2 - Werkwijze voor de bereiding van optisch actieve 2-amino-omega- oxoalkaanzuurderivaten. - Google Patents

Werkwijze voor de bereiding van optisch actieve 2-amino-omega- oxoalkaanzuurderivaten. Download PDF

Info

Publication number: NL1007113C2
Authority: NL; Netherlands
Prior art keywords: atoms; amino acid; acid amide; amino; formula
Prior art date: 1997-09-25

Application number

NL1007113A

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.)

1997-09-25

Filing date

1997-09-25

Publication date

1999-03-26

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=19765731&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NL1007113(C2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-09-25 Application filed by Dsm Nv filed Critical Dsm Nv

1997-09-25 Priority to NL1007113A priority Critical patent/NL1007113C2/nl

1998-09-04 Priority to DE69823941T priority patent/DE69823941T3/de

1998-09-04 Priority to EP98202972A priority patent/EP0905257B2/de

1998-09-04 Priority to AT98202972T priority patent/ATE267265T1/de

1998-09-04 Priority to ES98202972T priority patent/ES2221974T5/es

1998-09-15 Priority to SG1998003660A priority patent/SG74077A1/en

1998-09-23 Priority to CA002247952A priority patent/CA2247952A1/en

1998-09-23 Priority to IL12631398A priority patent/IL126313A/en

1998-09-24 Priority to KR1019980040182A priority patent/KR19990030181A/ko

1998-09-24 Priority to HU9802146A priority patent/HU220580B1/hu

1998-09-24 Priority to CN98120647.6A priority patent/CN1218797A/zh

1998-09-24 Priority to JP10306243A priority patent/JPH11236361A/ja

1998-09-24 Priority to NO984447A priority patent/NO984447L/no

1998-09-25 Priority to US09/160,342 priority patent/US6133002A/en

1998-09-25 Priority to CZ983086A priority patent/CZ308698A3/cs

1998-09-29 Priority to TW087116386A priority patent/TW430641B/zh

1999-03-26 Publication of NL1007113C2 publication Critical patent/NL1007113C2/nl

1999-03-26 Application granted granted Critical

2000-08-18 Priority to US09/641,619 priority patent/US6222052B1/en

2000-08-18 Priority to US09/640,916 priority patent/US6291701B1/en

2000-08-18 Priority to US09/640,796 priority patent/US6720169B1/en

Links

239000002253 acid Substances 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims description 20
238000000034 method Methods 0.000 title claims description 13
150000001413 amino acids Chemical class 0.000 claims abstract description 45
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 32
239000002262 Schiff base Substances 0.000 claims abstract description 25
150000004753 Schiff bases Chemical class 0.000 claims abstract description 25
150000001299 aldehydes Chemical class 0.000 claims abstract description 18
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 16
125000005219 aminonitrile group Chemical group 0.000 claims abstract description 14
238000006243 chemical reaction Methods 0.000 claims abstract description 8
230000007062 hydrolysis Effects 0.000 claims abstract description 7
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 7
230000002255 enzymatic effect Effects 0.000 claims abstract description 6
239000011541 reaction mixture Substances 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000004430 oxygen atom Chemical group O* 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 12
-1 2-Amino acid amide Chemical class 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
150000002825 nitriles Chemical class 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 11
239000012071 phase Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
241000589776 Pseudomonas putida Species 0.000 description 4
238000006359 acetalization reaction Methods 0.000 description 4
150000001241 acetals Chemical class 0.000 description 4
239000002585 base Substances 0.000 description 4
230000007071 enzymatic hydrolysis Effects 0.000 description 4
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
BCFZIUVRIDQCHF-UHFFFAOYSA-N 2-amino-5-(1,3-dioxolan-2-yl)pentanamide Chemical compound NC(=O)C(N)CCCC1OCCO1 BCFZIUVRIDQCHF-UHFFFAOYSA-N 0.000 description 3
108700023418 Amidases Proteins 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
102000005922 amidase Human genes 0.000 description 3
150000002009 diols Chemical class 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
NEROWICBJPSXRB-UHFFFAOYSA-N 4-(1,3-dioxolan-2-yl)butanal Chemical compound O=CCCCC1OCCO1 NEROWICBJPSXRB-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RQULWPSGQYZREI-LURJTMIESA-N L-Allysine Ethylene Acetal Chemical compound OC(=O)[C@@H](N)CCCC1OCCO1 RQULWPSGQYZREI-LURJTMIESA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical class [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
241000607534 Aeromonas Species 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
241000228212 Aspergillus Species 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 description 1
HXEACLLIILLPRG-RXMQYKEDSA-N D-pipecolic acid Chemical class OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 description 1
229930182820 D-proline Natural products 0.000 description 1
ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
GFXYTQPNNXGICT-YFKPBYRVSA-N L-allysine Chemical compound OC(=O)[C@@H](N)CCCC=O GFXYTQPNNXGICT-YFKPBYRVSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
241000186359 Mycobacterium Species 0.000 description 1
241000588843 Ochrobactrum Species 0.000 description 1
241000588814 Ochrobactrum anthropi Species 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
241000316848 Rhodococcus <scale insect> Species 0.000 description 1
238000007059 Strecker synthesis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 description 1
150000003935 benzaldehydes Chemical class 0.000 description 1
OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
239000005457 ice water Substances 0.000 description 1
GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Microbiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Analytical Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

NL1007113A 1997-09-25 1997-09-25 Werkwijze voor de bereiding van optisch actieve 2-amino-omega- oxoalkaanzuurderivaten. NL1007113C2 (nl)

Priority Applications (19)

Application Number	Priority Date	Filing Date	Title
NL1007113A NL1007113C2 (nl)	1997-09-25	1997-09-25	Werkwijze voor de bereiding van optisch actieve 2-amino-omega- oxoalkaanzuurderivaten.
DE69823941T DE69823941T3 (de)	1997-09-25	1998-09-04	Verfahren zur Herstellung von optisch-aktiven 2-omega-oxoalkansäurederivaten
EP98202972A EP0905257B2 (de)	1997-09-25	1998-09-04	Verfahren zur Herstellung von optisch-aktiven 2-omega-oxoalkansäurederivaten
AT98202972T ATE267265T1 (de)	1997-09-25	1998-09-04	Verfahren zur herstellung von optisch-aktiven 2- omega-oxoalkansäurederivaten
ES98202972T ES2221974T5 (es)	1997-09-25	1998-09-04	Proceso para preparar derivados de acidos 2-amino-omega-oxoalcanoicos opticamente activos.
SG1998003660A SG74077A1 (en)	1997-09-25	1998-09-15	Process for preparing optically active 2-amino-omega-oxoalkanoic acid derivatives
CA002247952A CA2247952A1 (en)	1997-09-25	1998-09-23	Process for preparing optically active 2-amino-w-oxoalkanoic acid derivatives
IL12631398A IL126313A (en)	1997-09-25	1998-09-23	PROCESS FOR PREPARING OPTICALLY ACTIVE 2-AMINO-ω-DIOXOALKANOIC ACID DERIVATIVES AND SOME INTERMEDIATES THEREOF
KR1019980040182A KR19990030181A (ko)	1997-09-25	1998-09-24	광학적 활성 ２-아미노-ω-옥소알카노산 유도체의 제조방법
HU9802146A HU220580B1 (hu)	1997-09-25	1998-09-24	Eljárás optikailag aktív 2-amino-omega-oxoalkánsav-származékok előállítására és a vegyületek
CN98120647.6A CN1218797A (zh)	1997-09-25	1998-09-24	一种制备旋光的2－氨基－ω－氧代链烷酸衍生物的方法
JP10306243A JPH11236361A (ja)	1997-09-25	1998-09-24	光学活性な２−アミノ−ω−オキソアルカン酸誘導体の製造法
NO984447A NO984447L (no)	1997-09-25	1998-09-24	FremgangsmÕte ved fremstilling av optisk aktive 2-amino-w-oksoalkanonsyrederivater
US09/160,342 US6133002A (en)	1997-09-25	1998-09-25	Process for preparing optically active 2-amino-ω-oxoalkanoic acid derivatives
CZ983086A CZ308698A3 (cs)	1997-09-25	1998-09-25	Způsob přípravy opticky aktivních derivátů kyseliny 2-amino-omega-oxoalkanové
TW087116386A TW430641B (en)	1997-09-25	1998-09-29	Process for preparing optically active 2-amino-ω-oxoalkanoic acid derivatives
US09/641,619 US6222052B1 (en)	1997-09-25	2000-08-18	Process for preparing optically active 2-amino-ω-oxoalkanoic acid derivatives
US09/640,916 US6291701B1 (en)	1997-09-25	2000-08-18	Process for preparing optically active 2-amino-ω-oxoalkanoic acid derivatives
US09/640,796 US6720169B1 (en)	1997-09-25	2000-08-18	Process for preparing optically active 2-amino-w-oxoalkanoic acid

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL1007113A NL1007113C2 (nl)	1997-09-25	1997-09-25	Werkwijze voor de bereiding van optisch actieve 2-amino-omega- oxoalkaanzuurderivaten.
NL1007113		1997-09-25

Publications (1)

Publication Number	Publication Date
NL1007113C2 true NL1007113C2 (nl)	1999-03-26

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ID=19765731

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1007113A NL1007113C2 (nl)	1997-09-25	1997-09-25	Werkwijze voor de bereiding van optisch actieve 2-amino-omega- oxoalkaanzuurderivaten.

Country Status (15)

Country	Link
EP (1)	EP0905257B2 (de)
JP (1)	JPH11236361A (de)
KR (1)	KR19990030181A (de)
CN (1)	CN1218797A (de)
AT (1)	ATE267265T1 (de)
CA (1)	CA2247952A1 (de)
CZ (1)	CZ308698A3 (de)
DE (1)	DE69823941T3 (de)
ES (1)	ES2221974T5 (de)
HU (1)	HU220580B1 (de)
IL (1)	IL126313A (de)
NL (1)	NL1007113C2 (de)
NO (1)	NO984447L (de)
SG (1)	SG74077A1 (de)
TW (1)	TW430641B (de)

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US6174711B1 (en)	1998-07-05	2001-01-16	Mitsubishi Gas Chemical Company	Method for producing L-allysine acetal
HUP0105151A3 (en)	1998-07-15	2004-11-29	Bristol Myers Squibb Co	Preparation of (s)-2-amino-6,6-dimethoxyhexanoic acid methyl ester via novel dioxolanes
US6620600B2 (en)	2000-09-15	2003-09-16	Bristol-Myers Squibb Co.	Enzymatic resolution of aryl and thio-substituted acids
JP2003081964A (ja) *	2001-09-13	2003-03-19	Japan Hydrazine Co Inc	α−アミノ酸アミドの製造方法
JP4851668B2 (ja) *	2001-09-13	2012-01-11	株式会社日本ファインケム	ジアルデヒドモノエチレンアセタールアミノニトリルの製造方法
DE10155065A1 (de) *	2001-11-09	2003-05-22	Degussa	Verfahren zur Kristallisation von Oxonorleucinacetal
WO2004089878A1 (ja) *	2003-04-02	2004-10-21	Tanabe Seiyaku Co., Ltd.	光学活性α－アミノニトリル化合物の製法
CN114988989A (zh) *	2021-03-02	2022-09-02	汉淇生医科技有限公司	戊二醛与1,6-己二醇之加成物、包含其之医药组合物及应用

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- 1997-09-25 NL NL1007113A patent/NL1007113C2/nl not_active IP Right Cessation
1998
- 1998-09-04 ES ES98202972T patent/ES2221974T5/es not_active Expired - Lifetime
- 1998-09-04 AT AT98202972T patent/ATE267265T1/de not_active IP Right Cessation
- 1998-09-04 DE DE69823941T patent/DE69823941T3/de not_active Expired - Fee Related
- 1998-09-04 EP EP98202972A patent/EP0905257B2/de not_active Expired - Lifetime
- 1998-09-15 SG SG1998003660A patent/SG74077A1/en unknown
- 1998-09-23 CA CA002247952A patent/CA2247952A1/en not_active Abandoned
- 1998-09-23 IL IL12631398A patent/IL126313A/en not_active IP Right Cessation
- 1998-09-24 HU HU9802146A patent/HU220580B1/hu not_active IP Right Cessation
- 1998-09-24 KR KR1019980040182A patent/KR19990030181A/ko not_active Withdrawn
- 1998-09-24 JP JP10306243A patent/JPH11236361A/ja active Pending
- 1998-09-24 NO NO984447A patent/NO984447L/no unknown
- 1998-09-24 CN CN98120647.6A patent/CN1218797A/zh active Pending
- 1998-09-25 CZ CZ983086A patent/CZ308698A3/cs unknown
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Also Published As

Publication number	Publication date
CN1218797A (zh)	1999-06-09
HUP9802146A2 (hu)	1999-04-28
HU9802146D0 (en)	1998-12-28
IL126313A0 (en)	1999-05-09
DE69823941T3 (de)	2007-10-18
ES2221974T3 (es)	2005-01-16
ES2221974T5 (es)	2007-10-16
NO984447L (no)	1999-03-26
HU220580B1 (hu)	2002-03-28
CA2247952A1 (en)	1999-03-25
DE69823941T2 (de)	2005-08-11
SG74077A1 (en)	2000-07-18
IL126313A (en)	2001-04-30
DE69823941D1 (de)	2004-06-24
JPH11236361A (ja)	1999-08-31
EP0905257A1 (de)	1999-03-31
NO984447D0 (no)	1998-09-24
CZ308698A3 (cs)	1999-05-12
EP0905257B1 (de)	2004-05-19
TW430641B (en)	2001-04-21
KR19990030181A (ko)	1999-04-26
HUP9802146A3 (en)	1999-09-28
ATE267265T1 (de)	2004-06-15
EP0905257B2 (de)	2007-02-21

Legal Events

Date	Code	Title	Description
1999-06-01	PD2B	A search report has been drawn up
2002-06-03	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20020401
2003-06-02	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20020401

Publication	Publication Date	Title
NL1007113C2 (nl)	1999-03-26	Werkwijze voor de bereiding van optisch actieve 2-amino-omega- oxoalkaanzuurderivaten.
DK172106B1 (da)	1997-10-27	Ny fremgangsmåde og mellemprodukter og anvendelse heraf til syntese af levodopa
NL9000386A (nl)	1991-09-16	Werkwijze voor de bereiding van optisch aktief aminozuuramide.
US6133002A (en)	2000-10-17	Process for preparing optically active 2-amino-ω-oxoalkanoic acid derivatives
KR100416927B1 (ko)	2004-05-24	광학적활성아민의제조방법
JP3714964B2 (ja)	2005-11-09	光学活性アミン類の製造方法
NL9201230A (nl)	1994-02-01	Werkwijze voor de bereiding van optisch aktief methionineamide.
CA2256396C (en)	2006-03-14	Process for producing optically active amines
EP0341462B1 (de)	1992-09-09	Diastereoselektives Verfahren zur Herstellung von Zwischenprodukten verwendbar zur Peptidderivatensynthese
JP4995429B2 (ja)	2012-08-08	マンデル酸類の精製方法
CN117069612B (zh)	2025-11-07	一种合成氰基丙烯酸酯的新方法
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HK1018952A (en)	2000-01-14	PROCESS FOR PREPARING OPTICALLY ACTIVE 2-AMINO-ω-OXOALKANOIC ACID DERIVATIVES
US5763638A (en)	1998-06-09	Preparation of aromatic nitriles
SU1321723A1 (ru)	1987-07-07	Способ получени 4-замещенных 5-алкилпиразолидонов-3
CA1238918A (fr)	1988-07-05	Thioamides, leurs preparation et applications
JPH11508567A (ja)	1999-07-27	β−アミノ−α−ヒドロキシカルボン酸及びその誘導体の製造方法
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KR100463791B1 (ko)	2005-06-10	광학활성아민의제조방법
KR20010022843A (ko)	2001-03-26	시스- 및 트랜스-피롤로피페리딘의 라세미체 분할 방법
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Hadad et al.	1991	Selective intracomplex reaction of pendant groups in a purine-pyrimidines base pair
JPH06733B2 (ja)	1994-01-05	光学活性３−ハイドロキシ−４−ハロゲノ−ブチロニトリルの製造法