CS103091A3 - Protected substituted benzhydrylamines as shoulders for the synthesis ofpeptides on solid phase, process of their preparation and use - Google Patents

Protected substituted benzhydrylamines as shoulders for the synthesis ofpeptides on solid phase, process of their preparation and use Download PDF

Info

Publication number: CS103091A3
Authority: CS; Czechoslovakia
Prior art keywords: substituted; benzhydrylamines; protected; preparation; peptide
Prior art date: 1991-04-12

Application number

CS911030A

Other languages

Czech (cs)

English (en)

Inventor

Marcel Ing Patek

Michal Ing Csc Lebl

Original Assignee

Ustav Organicke Chemie A Bioch

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.)

1991-04-12

Filing date

1991-04-12

Publication date

1992-10-14

1991-04-12 Application filed by Ustav Organicke Chemie A Bioch filed Critical Ustav Organicke Chemie A Bioch

1991-04-12 Priority to CS911030A priority Critical patent/CS103091A3/cs

1992-04-10 Priority to AT92917473T priority patent/ATE139995T1/de

1992-04-10 Priority to PCT/US1992/002962 priority patent/WO1992018144A1/en

1992-04-10 Priority to CA002109433A priority patent/CA2109433C/en

1992-04-10 Priority to DK92917473.8T priority patent/DK0579785T3/da

1992-04-10 Priority to US08/137,048 priority patent/US5684131A/en

1992-04-10 Priority to DE69211990T priority patent/DE69211990T2/de

1992-04-10 Priority to ES92917473T priority patent/ES2089548T3/es

1992-04-10 Priority to HU9302867A priority patent/HU222239B1/hu

1992-04-10 Priority to JP51027792A priority patent/JP3634356B2/ja

1992-04-10 Priority to EP92917473A priority patent/EP0579785B1/de

1992-10-14 Publication of CS103091A3 publication Critical patent/CS103091A3/cs

1996-07-04 Priority to GR960401664T priority patent/GR3020463T3/el

1997-10-30 Priority to US08/960,882 priority patent/US5891995A/en

Links

MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical class C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 title claims abstract description 15
230000015572 biosynthetic process Effects 0.000 title claims abstract description 7
238000003786 synthesis reaction Methods 0.000 title claims abstract description 7
238000000034 method Methods 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title claims description 6
239000007790 solid phase Substances 0.000 title abstract 2
108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 18
150000001408 amides Chemical class 0.000 claims abstract description 7
239000002253 acid Substances 0.000 claims description 8
150000001413 amino acids Chemical class 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 6
150000003462 sulfoxides Chemical class 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 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 claims description 4
239000011701 zinc Substances 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
239000012965 benzophenone Substances 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
230000004913 activation Effects 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
150000002923 oximes Chemical class 0.000 claims description 2
150000003568 thioethers Chemical class 0.000 claims description 2
150000008366 benzophenones Chemical class 0.000 claims 2
125000005519 fluorenylmethyloxycarbonyl group Chemical group 0.000 claims 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
150000001412 amines Chemical group 0.000 claims 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 abstract description 6
230000007017 scission Effects 0.000 abstract description 6
238000010647 peptide synthesis reaction Methods 0.000 abstract description 4
125000003275 alpha amino acid group Chemical group 0.000 abstract 1
238000010511 deprotection reaction Methods 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 6
239000000047 product Substances 0.000 description 6
-1 4-benzylthiophenyl Chemical group 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 3
102000004196 processed proteins & peptides Human genes 0.000 description 3
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
238000002451 electron ionisation mass spectrometry Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
GRHQDJDRGZFIPO-UHFFFAOYSA-N 4-bromobutanoic acid Chemical compound OC(=O)CCCBr GRHQDJDRGZFIPO-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
AYGXHRXZVUYYPT-UHFFFAOYSA-N anisole;dichloromethane;2,2,2-trifluoroacetic acid Chemical compound ClCCl.OC(=O)C(F)(F)F.COC1=CC=CC=C1 AYGXHRXZVUYYPT-UHFFFAOYSA-N 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
238000002523 gelfiltration Methods 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000007420 reactivation Effects 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000011697 sodium iodate Substances 0.000 description 1
235000015281 sodium iodate Nutrition 0.000 description 1
229940032753 sodium iodate Drugs 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/16—Oxytocins; Vasopressins; Related peptides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
- C07K1/042—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers characterised by the nature of the carrier
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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)
Analytical Chemistry (AREA)
Peptides Or Proteins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS911030A 1991-04-12 1991-04-12 Protected substituted benzhydrylamines as shoulders for the synthesis ofpeptides on solid phase, process of their preparation and use CS103091A3 (en)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
CS911030A CS103091A3 (en)	1991-04-12	1991-04-12	Protected substituted benzhydrylamines as shoulders for the synthesis ofpeptides on solid phase, process of their preparation and use
US08/137,048 US5684131A (en)	1991-04-12	1992-04-10	Substituted benzhydrylamines as handles for solid phase peptide synthesis
PCT/US1992/002962 WO1992018144A1 (en)	1991-04-12	1992-04-10	Substituted benzhydrylamines as handles for solid phase peptide synthesis
CA002109433A CA2109433C (en)	1991-04-12	1992-04-10	Substituted benzhydrylamines as handles for solid phase peptide synthesis
DK92917473.8T DK0579785T3 (da)	1991-04-12	1992-04-10	Substituerede benzhydrylaminer som tlslutningsmolekyler til fastfasepeptidsyntese
AT92917473T ATE139995T1 (de)	1991-04-12	1992-04-10	Substituierte benzhydrylamine als anknüpfungsmoleküle bei der festphasenpeptidsynthese
DE69211990T DE69211990T2 (de)	1991-04-12	1992-04-10	Substituierte benzhydrylamine als anknüpfungsmoleküle bei der festphasenpeptidsynthese
ES92917473T ES2089548T3 (es)	1991-04-12	1992-04-10	Benzhidrilaminas sustituidas como agentes de conexion para sintesis de peptidos en fase solida.
HU9302867A HU222239B1 (hu)	1991-04-12	1992-04-10	Eljárás szilárd fázisú peptidszintézisben alkalmazható szubsztituált benzhidril-amin kapcsoló vegyületek és ezeket tartalmazó konjugátumok előállítására, valamint az azokkal végzett peptidszintézisre
JP51027792A JP3634356B2 (ja)	1991-04-12	1992-04-10	固相ペプチド合成用ハンドルとしての置換ベンズヒドリルアミン
EP92917473A EP0579785B1 (de)	1991-04-12	1992-04-10	Substituierte benzhydrylamine als anknüpfungsmoleküle bei der festphasenpeptidsynthese
GR960401664T GR3020463T3 (en)	1991-04-12	1996-07-04	Substituted benzhydrylamines as handles for solid phase peptide synthesis
US08/960,882 US5891995A (en)	1991-04-12	1997-10-30	Substituted benzhydrylamines as handles for solid phase peptide synthesis

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS911030A CS103091A3 (en)	1991-04-12	1991-04-12	Protected substituted benzhydrylamines as shoulders for the synthesis ofpeptides on solid phase, process of their preparation and use

Publications (1)

Publication Number	Publication Date
CS103091A3 true CS103091A3 (en)	1992-10-14

Family

ID=5343649

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS911030A CS103091A3 (en)	1991-04-12	1991-04-12	Protected substituted benzhydrylamines as shoulders for the synthesis ofpeptides on solid phase, process of their preparation and use

Country Status (12)

Country	Link
US (2)	US5684131A (de)
EP (1)	EP0579785B1 (de)
JP (1)	JP3634356B2 (de)
AT (1)	ATE139995T1 (de)
CA (1)	CA2109433C (de)
CS (1)	CS103091A3 (de)
DE (1)	DE69211990T2 (de)
DK (1)	DK0579785T3 (de)
ES (1)	ES2089548T3 (de)
GR (1)	GR3020463T3 (de)
HU (1)	HU222239B1 (de)
WO (1)	WO1992018144A1 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT1156059E (pt) *	1993-06-21	2007-10-19	Aventis Pharma Inc	Ligantes cliváveis selectivamente com base num grupo de metionina e um grupo éster
ES2115543B1 (es) *	1996-08-06	1999-02-16	Lipotec Sa	Procedimiento para la obtencion de carbetocina y sus sales de adicion de acido farmaceuticamente aceptables o complejos de la misma.
GB9620202D0 (en) *	1996-09-27	1996-11-13	Rhone Poulenc Agriculture	New herbicides
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1991
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1992
- 1992-04-10 ES ES92917473T patent/ES2089548T3/es not_active Expired - Lifetime
- 1992-04-10 AT AT92917473T patent/ATE139995T1/de not_active IP Right Cessation
- 1992-04-10 US US08/137,048 patent/US5684131A/en not_active Expired - Fee Related
- 1992-04-10 CA CA002109433A patent/CA2109433C/en not_active Expired - Fee Related
- 1992-04-10 DK DK92917473.8T patent/DK0579785T3/da not_active Application Discontinuation
- 1992-04-10 WO PCT/US1992/002962 patent/WO1992018144A1/en not_active Ceased
- 1992-04-10 EP EP92917473A patent/EP0579785B1/de not_active Expired - Lifetime
- 1992-04-10 JP JP51027792A patent/JP3634356B2/ja not_active Expired - Fee Related
- 1992-04-10 DE DE69211990T patent/DE69211990T2/de not_active Expired - Fee Related
- 1992-04-10 HU HU9302867A patent/HU222239B1/hu not_active IP Right Cessation
1996
- 1996-07-04 GR GR960401664T patent/GR3020463T3/el unknown
1997
- 1997-10-30 US US08/960,882 patent/US5891995A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE69211990T2 (de)	1996-11-28
HU222239B1 (hu)	2003-05-28
HU9302867D0 (en)	1993-12-28
HUT70198A (en)	1995-09-28
US5891995A (en)	1999-04-06
DK0579785T3 (da)	1996-10-28
ATE139995T1 (de)	1996-07-15
WO1992018144A1 (en)	1992-10-29
ES2089548T3 (es)	1996-10-01
EP0579785B1 (de)	1996-07-03
EP0579785A4 (en)	1994-07-06
US5684131A (en)	1997-11-04
DE69211990D1 (de)	1996-08-08
CA2109433C (en)	2006-07-11
GR3020463T3 (en)	1996-10-31
JP3634356B2 (ja)	2005-03-30
CA2109433A1 (en)	1992-10-13
JPH06506940A (ja)	1994-08-04
EP0579785A1 (de)	1994-01-26

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