NO880034L - Fremgangsmaate for fremstilling av krystallinsk aminobeskyttet beta-benzyl-l-aspartinsyre. - Google Patents

Fremgangsmaate for fremstilling av krystallinsk aminobeskyttet beta-benzyl-l-aspartinsyre.

Info

Publication number: NO880034L
Authority: NO; Norway
Prior art keywords: approx; benzyl; aspartic acid; amino; liquid phase
Prior art date: 1987-01-07

Application number

NO880034A

Other languages

English (en)

Norwegian (no)

Other versions

NO880034D0 (no

Inventor

John M Pascone

Original Assignee

Ortho Pharma Corp

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.)

1987-01-07

Filing date

1988-01-06

Publication date

1988-07-08

1988-01-06 Application filed by Ortho Pharma Corp filed Critical Ortho Pharma Corp

1988-01-06 Publication of NO880034D0 publication Critical patent/NO880034D0/no

1988-07-08 Publication of NO880034L publication Critical patent/NO880034L/no

Links

-1 AMINO Chemical class 0.000 title claims description 34
238000000034 method Methods 0.000 title claims description 27
KMVYGTIPJNGNRD-GKAPJAKFSA-N (2s)-2-amino-3-benzylbutanedioic acid Chemical compound OC(=O)[C@@H](N)C(C(O)=O)CC1=CC=CC=C1 KMVYGTIPJNGNRD-GKAPJAKFSA-N 0.000 title claims 2
238000002360 preparation method Methods 0.000 title description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 78
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 72
229960005261 aspartic acid Drugs 0.000 claims description 59
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 47
239000000203 mixture Substances 0.000 claims description 30
239000007791 liquid phase Substances 0.000 claims description 28
238000002425 crystallisation Methods 0.000 claims description 19
239000003607 modifier Substances 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
230000008025 crystallization Effects 0.000 claims description 18
125000006239 protecting group Chemical group 0.000 claims description 18
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
239000007864 aqueous solution Substances 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
239000013078 crystal Substances 0.000 claims description 11
238000004821 distillation Methods 0.000 claims description 11
239000007788 liquid Substances 0.000 claims description 11
239000003495 polar organic solvent Substances 0.000 claims description 9
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 9
150000003512 tertiary amines Chemical class 0.000 claims description 9
239000008346 aqueous phase Substances 0.000 claims description 8
238000001816 cooling Methods 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
150000002430 hydrocarbons Chemical class 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
239000004615 ingredient Substances 0.000 claims 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 32
239000000243 solution Substances 0.000 description 21
239000000047 product Substances 0.000 description 17
229940024606 amino acid Drugs 0.000 description 16
239000012044 organic layer Substances 0.000 description 15
239000012071 phase Substances 0.000 description 15
239000002253 acid Substances 0.000 description 13
230000015572 biosynthetic process Effects 0.000 description 13
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
108090000765 processed proteins & peptides Proteins 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical class OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 10
239000010410 layer Substances 0.000 description 10
230000020477 pH reduction Effects 0.000 description 10
102000004196 processed proteins & peptides Human genes 0.000 description 10
239000007795 chemical reaction product Substances 0.000 description 9
229920001184 polypeptide Polymers 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
238000010647 peptide synthesis reaction Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
125000003277 amino group Chemical group 0.000 description 7
239000002798 polar solvent Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
150000001413 amino acids Chemical class 0.000 description 6
PMPYSSMGWFNAAQ-UHFFFAOYSA-N dichloromethane;n,n-diethylethanamine Chemical compound ClCCl.CCN(CC)CC PMPYSSMGWFNAAQ-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 5
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000005187 foaming Methods 0.000 description 5
230000006911 nucleation Effects 0.000 description 5
238000010899 nucleation Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
150000007530 organic bases Chemical class 0.000 description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
VKCARTLEXJLJBZ-YFKPBYRVSA-N (3s)-4-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(N)=O)CC(O)=O VKCARTLEXJLJBZ-YFKPBYRVSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000002411 adverse Effects 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000002518 antifoaming agent Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000006378 damage Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
239000011521 glass Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000002667 nucleating agent Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
239000011343 solid material Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-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
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
101150101537 Olah gene Proteins 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000006242 amine protecting group Chemical group 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical group OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
AMTWCFIAVKBGOD-UHFFFAOYSA-N dioxosilane;methoxy-dimethyl-trimethylsilyloxysilane Chemical compound O=[Si]=O.CO[Si](C)(C)O[Si](C)(C)C AMTWCFIAVKBGOD-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000010931 ester hydrolysis Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
230000035784 germination Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
239000011133 lead Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
230000005588 protonation Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000012070 reactive reagent Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229940083037 simethicone Drugs 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
238000012800 visualization Methods 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO880034A 1987-01-07 1988-01-06 Fremgangsmaate for fremstilling av krystallinsk aminobeskyttet beta-benzyl-l-aspartinsyre. NO880034L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/001,076 US4713480A (en)	1987-01-07	1987-01-07	Method for the production of crystalline amino-protected-beta-benzyl-L-aspartic acid

Publications (2)

Publication Number	Publication Date
NO880034D0 NO880034D0 (no)	1988-01-06
NO880034L true NO880034L (no)	1988-07-08

Family

ID=21694260

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO880034A NO880034L (no)	1987-01-07	1988-01-06	Fremgangsmaate for fremstilling av krystallinsk aminobeskyttet beta-benzyl-l-aspartinsyre.

Country Status (10)

Country	Link
US (1)	US4713480A (da)
EP (1)	EP0274423A2 (da)
JP (1)	JPS63188658A (da)
AU (1)	AU1009688A (da)
DK (1)	DK4488D0 (da)
FI (1)	FI880035L (da)
IL (1)	IL85040A0 (da)
NO (1)	NO880034L (da)
PT (1)	PT86498B (da)
ZA (1)	ZA8874B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5140058A (en) *	1990-06-22	1992-08-18	Grow Group, Inc.	Method of decreasing formaldehyde content in organic paint coating systems

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3062804A (en) *	1957-03-08	1962-11-06	Sterling Drug Inc	Peptide synthesis and intermediates therefor
US3062805A (en) *	1957-03-08	1962-11-06	Sterling Drug Inc	Peptide synthesis and intermediates therefor
US3445447A (en) *	1965-02-04	1969-05-20	Ajinomoto Kk	Tert-amyloxycarbonyl derivatives of amino acids
US3875207A (en) *	1967-01-25	1975-04-01	Ciba Geigy Corp	Process for the temporary protection of amino groups in peptide syntheses
US3609164A (en) *	1968-03-27	1971-09-28	Tanabe Seiyaku Co	Process for preparing {11 -butoxycarbonyl compounds
US3711458A (en) *	1969-08-21	1973-01-16	Research Corp	Substituted and unsubstituted vinyloxycarbonyl groups as amino protecting groups in the syntheses of peptides
NL7103339A (da) *	1970-03-19	1971-09-21	Hoechst Ag
US3906031A (en) *	1971-03-15	1975-09-16	Research Corp	Novel 9-fluorenylmethoxycarbonyl compounds
US3891692A (en) *	1972-05-03	1975-06-24	Merck & Co Inc	N-(cyclopropylalkoxycarbonyl)amino acids
US4082736A (en) *	1976-04-26	1978-04-04	Syntex (U.S.A.) Inc.	Novel immunological adjuvant compounds and methods of preparation thereof
LU80207A1 (de) *	1978-09-07	1980-04-21	H Kalbacher	Neue substituierte kohlensaeureester und urethane,verfahren zu ihrer herstellung und deren verwendung

1987
- 1987-01-07 US US07/001,076 patent/US4713480A/en not_active Expired - Lifetime
- 1987-12-28 JP JP62330303A patent/JPS63188658A/ja active Pending
1988
- 1988-01-06 DK DK004488A patent/DK4488D0/da not_active Application Discontinuation
- 1988-01-06 FI FI880035A patent/FI880035L/fi not_active Application Discontinuation
- 1988-01-06 EP EP88300060A patent/EP0274423A2/en not_active Withdrawn
- 1988-01-06 AU AU10096/88A patent/AU1009688A/en not_active Abandoned
- 1988-01-06 IL IL85040A patent/IL85040A0/xx unknown
- 1988-01-06 PT PT86498A patent/PT86498B/pt not_active IP Right Cessation
- 1988-01-06 NO NO880034A patent/NO880034L/no unknown
- 1988-01-06 ZA ZA8874A patent/ZA8874B/xx unknown

Also Published As

Publication number	Publication date
PT86498B (pt)	1991-12-31
NO880034D0 (no)	1988-01-06
EP0274423A2 (en)	1988-07-13
JPS63188658A (ja)	1988-08-04
PT86498A (en)	1988-02-01
ZA8874B (en)	1989-09-27
AU1009688A (en)	1988-07-14
DK4488D0 (da)	1988-01-06
US4713480A (en)	1987-12-15
FI880035A7 (fi)	1988-07-08
IL85040A0 (en)	1988-06-30
FI880035L (fi)	1988-07-08
FI880035A0 (fi)	1988-01-06

Publication	Publication Date	Title
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