DD284031A5 - Verfahren zur herstellung eines kunstharzes - Google Patents

Verfahren zur herstellung eines kunstharzes Download PDF

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Publication number: DD284031A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; group; amino; amino acid; groups
Prior art date: 1987-03-30

Application number

DD88331994A

Other languages

German (de)

English (en)

Inventor

Hans Rink

Original Assignee

��`��@��k��

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.)

1987-03-30

Filing date

1988-03-28

Publication date

1990-10-31

1988-03-28 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1990-10-31 Publication of DD284031A5 publication Critical patent/DD284031A5/de

Links

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- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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Peptides Or Proteins (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Materials For Medical Uses (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Compositions Of Macromolecular Compounds (AREA)
Dental Preparations (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Glass Compositions (AREA)
Polyamides (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Polyesters Or Polycarbonates (AREA)
Working-Up Tar And Pitch (AREA)
Paper (AREA)

DD88331994A 1987-03-30 1988-03-28 Verfahren zur herstellung eines kunstharzes DD284031A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH121487		1987-03-30

Publications (1)

Publication Number	Publication Date
DD284031A5 true DD284031A5 (de)	1990-10-31

Family

ID=4205167

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
DD88331994A DD284031A5 (de)	1987-03-30	1988-03-28	Verfahren zur herstellung eines kunstharzes
DD88314098A DD274033A5 (de)	1987-03-30	1988-03-28	Verfahren zur herstellung von peptiden und peptidamiden
DD88331996A DD296087A5 (de)	1987-03-30	1988-03-28	Verfahren zur herstellung eines kunstharzes

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
DD88314098A DD274033A5 (de)	1987-03-30	1988-03-28	Verfahren zur herstellung von peptiden und peptidamiden
DD88331996A DD296087A5 (de)	1987-03-30	1988-03-28	Verfahren zur herstellung eines kunstharzes

Country Status (19)

Country	Link
US (3)	US4859736A (pt)
EP (1)	EP0285562B1 (pt)
JP (1)	JP2513775B2 (pt)
KR (1)	KR950013679B1 (pt)
AT (1)	ATE88726T1 (pt)
AU (1)	AU615181B2 (pt)
CA (1)	CA1318462C (pt)
DD (3)	DD284031A5 (pt)
DE (1)	DE3880541D1 (pt)
DK (1)	DK175042B1 (pt)
ES (1)	ES2054863T3 (pt)
FI (1)	FI90780C (pt)
GR (1)	GR3007996T3 (pt)
HU (1)	HU208155B (pt)
IE (1)	IE61485B1 (pt)
IL (1)	IL85884A (pt)
MX (1)	MX10917A (pt)
PT (1)	PT87105B (pt)
YU (1)	YU62588A (pt)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8430252D0 (en) *	1984-11-30	1985-01-09	Beecham Group Plc	Compounds
NL194729C (nl) *	1986-10-13	2003-01-07	Novartis Ag	Werkwijze voor de bereiding van peptidealcoholen via vaste fase.
US4859736A (en) *	1987-03-30	1989-08-22	Ciba-Geigy Corporation	Synthetic polystyrene resin and its use in solid phase peptide synthesis
US5242974A (en) *	1991-11-22	1993-09-07	Affymax Technologies N.V.	Polymer reversal on solid surfaces
US5212288A (en) *	1990-02-20	1993-05-18	Syntex (U.S.A.) Inc.	Temporary minimal protection synthesis of serine-containing polypeptides
US5155166A (en) *	1990-06-18	1992-10-13	Eastman Kodak Company	Use of 1-(1-pyrrolidinylcarbonyl)pyridinium salts to attach compounds to carboxylated particles and a kit containing same
US5071565A (en) *	1991-02-04	1991-12-10	Iowa State University Research Foundation, Inc.	Modified resins for solid-phase extraction
US5550215A (en) *	1991-11-22	1996-08-27	Holmes; Christopher P.	Polymer reversal on solid surfaces
US5268423A (en) *	1992-02-28	1993-12-07	New York University	Method for preparation of peptide synthesis resins and peptide synthesis resins
US5516891A (en) *	1992-06-16	1996-05-14	Kinerton, Ltd.	Liquid phase synthesis of peptides and peptide derivatives
IE921942A1 (en) *	1992-06-16	1993-12-29	Gary A Siwruk John S Eynon	Liquid phase synthesis of peptides and peptide derivatives
US5463564A (en)	1994-09-16	1995-10-31	3-Dimensional Pharmaceuticals, Inc.	System and method of automatically generating chemical compounds with desired properties
US6571227B1 (en)	1996-11-04	2003-05-27	3-Dimensional Pharmaceuticals, Inc.	Method, system and computer program product for non-linear mapping of multi-dimensional data
US6295514B1 (en)	1996-11-04	2001-09-25	3-Dimensional Pharmaceuticals, Inc.	Method, system, and computer program product for representing similarity/dissimilarity between chemical compounds
US6453246B1 (en)	1996-11-04	2002-09-17	3-Dimensional Pharmaceuticals, Inc.	System, method, and computer program product for representing proximity data in a multi-dimensional space
US6392010B1 (en)	1996-12-19	2002-05-21	Aventis Pharmaceuticals Inc.	Process for the solid phase synthesis of aldehyde, ketone, oxime, amine, hydroxamic acid and αβ-unsaturated carboxylic acid and aldehyde compounds
GB9717173D0 (en)	1997-08-13	1997-10-22	Akzo Nobel Nv	Solid phase supports
US6114468A (en) *	1998-06-01	2000-09-05	Novartis Ag	Synthetic resins for use in solid phase synthesis
US7416524B1 (en)	2000-02-18	2008-08-26	Johnson & Johnson Pharmaceutical Research & Development, L.L.C.	System, method and computer program product for fast and efficient searching of large chemical libraries
US6671627B2 (en)	2000-02-29	2003-12-30	3-D Pharmaceuticals, Inc.	Method and computer program product for designing combinatorial arrays
US7039621B2 (en)	2000-03-22	2006-05-02	Johnson & Johnson Pharmaceutical Research & Development, L.L.C.	System, method, and computer program product for representing object relationships in a multidimensional space
AU2001249805A1 (en)	2000-04-03	2001-10-15	3-Dimensional Pharmaceuticals, Inc.	Method, system, and computer program product for representing object relationships in a multidimensional space
CA2419600A1 (en) *	2000-08-22	2002-02-28	3-Dimensional Pharmaceuticals, Inc.	Method, system, and computer program product for determining properties of combinatorial library products from features of library building blocks
US6678619B2 (en) *	2000-09-20	2004-01-13	Victor S. Lobanov	Method, system, and computer program product for encoding and building products of a virtual combinatorial library
WO2002061419A1 (en) *	2001-01-29	2002-08-08	3-Dimensional Pharmaceuticals, Inc.	Method, system, and computer program product for analyzing combinatorial libraries
WO2002083606A1 (en) *	2001-04-17	2002-10-24	University Of Alberta	A linker system for the synthesis and screening of combinatorial libraries of polyamine derivatives on water compatible supports
US7119145B2 (en) *	2002-01-25	2006-10-10	Phenomenex, Inc.	Surface graft modified resins and formation thereof
US6926823B2 (en) *	2002-06-03	2005-08-09	Varian, Inc.	Polymer with superior polar retention for sample pretreatment
ATE501164T1 (de) *	2003-07-04	2011-03-15	Lonza Ag	Verbessertes verfahren für festphasensynthese
EP1630600A3 (en) *	2004-07-29	2006-03-22	Rohm and Haas Electronic Materials, L.L.C.	Hot melt composition and method involving forming a masking pattern
WO2006060803A2 (en) *	2004-12-03	2006-06-08	Polnox Corporation	One pot process for making polymeric antioxidants
US8742028B2 (en) *	2009-05-06	2014-06-03	Mallinckrodt Llc	Solid support for Fmoc-solid phase synthesis of peptide acids
TW202446781A (zh)	2011-12-28	2024-12-01	日商中外製藥股份有限公司	胜肽化合物之製造方法
EP3071544B1 (en)	2013-11-22	2022-07-06	Polnox Corporation	Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same
EP4166664A1 (en)	2015-03-13	2023-04-19	Chugai Seiyaku Kabushiki Kaisha	Modified aminoacyl-trna synthetase and use thereof
JP7187323B2 (ja)	2017-01-31	2022-12-12	中外製薬株式会社	無細胞翻訳系におけるペプチドの合成方法
WO2018160879A2 (en)	2017-03-01	2018-09-07	Polnox Corporation	Macromolecular corrosion (mcin) inhibitors: structures, methods of making and using the same
KR20250007021A (ko)	2017-06-09	2025-01-13	추가이 세이야쿠 가부시키가이샤	N-치환 아미노산을 포함하는 펩타이드의 합성 방법
WO2019117274A1 (ja) *	2017-12-15	2019-06-20	中外製薬株式会社	ペプチドの製造方法、及び塩基の処理方法
EP3878836B1 (en)	2018-11-07	2025-07-23	Chugai Seiyaku Kabushiki Kaisha	O-substituted serine derivative production method
WO2020111238A1 (ja)	2018-11-30	2020-06-04	中外製薬株式会社	ペプチド化合物、またはアミド化合物の脱保護法および固相反応における脱樹脂方法、並びにペプチド化合物の製造方法
EP3939962A4 (en)	2019-03-15	2022-12-28	Chugai Seiyaku Kabushiki Kaisha	PROCESS FOR PREPARING AN AROMATIC AMINO ACID DERIVATIVE
BR112022007535A2 (pt)	2019-11-07	2022-07-12	Chugai Pharmaceutical Co Ltd	Composto peptídico cíclico tendo ação inibitória de kras
CN119912618B (zh) *	2023-10-31	2025-11-18	北京索特莱克科技发展有限公司	提锂树脂的结构、制备和应用

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE141977C (pt) *
GB1406611A (en) *	1971-08-17	1975-09-17	Leo Ab	Pharmaceutically active secondary phosphoric acid esters
DD141977A3 (de) *	1975-07-11	1980-06-04	Jens Fischer	Verfahren zur herstellung wasserunloeslicher enzym-polystyrol-komplexe
US4301045A (en) *	1977-05-02	1981-11-17	Armour Pharmaceutical Company	Synthesis of peptides
US4507230A (en) *	1982-05-12	1985-03-26	Research Corporation	Peptide synthesis reagents and method of use
US4569967A (en) *	1983-10-24	1986-02-11	The Salk Institute For Biological Studies	Synthesis of N-substituted peptide amides
US4623484A (en) *	1984-05-24	1986-11-18	Research Corporation	Process for peptide synthesis
GB2169901A (en) *	1984-12-11	1986-07-23	Lkb Biochrom Ltd	method for a solid phase synthesis of a linear combination of amino acid residues.
US4731412A (en) *	1984-12-28	1988-03-15	The Salk Institute Biotechnology/Industrial Associates, Inc.	Process and composition for amino-terminal, α-aspartyl and α-glutamyl dipeptide esters
US4716147A (en) *	1986-03-27	1987-12-29	Monsanto Company	Synthetic airial peptides
CA1329124C (en) *	1987-02-02	1994-05-03	Jerald C. Sadoff	Conjugate malaria vaccine
US4859736A (en) *	1987-03-30	1989-08-22	Ciba-Geigy Corporation	Synthetic polystyrene resin and its use in solid phase peptide synthesis

1988
- 1988-03-21 US US07/171,049 patent/US4859736A/en not_active Expired - Lifetime
- 1988-03-22 EP EP88810187A patent/EP0285562B1/de not_active Expired - Lifetime
- 1988-03-22 DE DE8888810187T patent/DE3880541D1/de not_active Expired - Lifetime
- 1988-03-22 ES ES88810187T patent/ES2054863T3/es not_active Expired - Lifetime
- 1988-03-22 AT AT88810187T patent/ATE88726T1/de not_active IP Right Cessation
- 1988-03-28 JP JP63072147A patent/JP2513775B2/ja not_active Expired - Lifetime
- 1988-03-28 PT PT87105A patent/PT87105B/pt not_active IP Right Cessation
- 1988-03-28 MX MX1091788A patent/MX10917A/es unknown
- 1988-03-28 DD DD88331994A patent/DD284031A5/de not_active IP Right Cessation
- 1988-03-28 CA CA000562701A patent/CA1318462C/en not_active Expired - Lifetime
- 1988-03-28 FI FI881451A patent/FI90780C/fi not_active IP Right Cessation
- 1988-03-28 DD DD88314098A patent/DD274033A5/de not_active IP Right Cessation
- 1988-03-28 IL IL85884A patent/IL85884A/xx not_active IP Right Cessation
- 1988-03-28 DD DD88331996A patent/DD296087A5/de not_active IP Right Cessation
- 1988-03-29 HU HU881569A patent/HU208155B/hu unknown
- 1988-03-29 IE IE94088A patent/IE61485B1/en not_active IP Right Cessation
- 1988-03-29 AU AU13814/88A patent/AU615181B2/en not_active Expired
- 1988-03-29 DK DK198801730A patent/DK175042B1/da not_active IP Right Cessation
- 1988-03-29 YU YU00625/88A patent/YU62588A/xx unknown
- 1988-03-30 KR KR1019880003482A patent/KR950013679B1/ko not_active Expired - Lifetime
1989
- 1989-05-17 US US07/353,311 patent/US5004781A/en not_active Expired - Lifetime
1991
- 1991-06-20 US US07/719,090 patent/US5093530A/en not_active Expired - Lifetime
1993
- 1993-05-28 GR GR920403072T patent/GR3007996T3/el unknown

Also Published As

Publication number	Publication date
DK173088A (da)	1988-10-01
DD296087A5 (de)	1991-11-21
FI881451A7 (fi)	1988-10-01
JPS63260946A (ja)	1988-10-27
HU208155B (en)	1993-08-30
US5004781A (en)	1991-04-02
DK173088D0 (da)	1988-03-29
IE880940L (en)	1988-09-30
DK175042B1 (da)	2004-05-10
AU1381488A (en)	1988-09-29
FI90780B (fi)	1993-12-15
KR880011210A (ko)	1988-10-27
YU62588A (en)	1990-10-31
EP0285562B1 (de)	1993-04-28
AU615181B2 (en)	1991-09-26
EP0285562A3 (en)	1990-01-10
HUT46713A (en)	1988-11-28
ES2054863T3 (es)	1994-08-16
PT87105A (pt)	1988-04-01
FI881451A0 (fi)	1988-03-28
PT87105B (pt)	1992-07-31
KR950013679B1 (ko)	1995-11-13
MX10917A (es)	1993-12-01
JP2513775B2 (ja)	1996-07-03
IL85884A (en)	1992-01-15
US5093530A (en)	1992-03-03
DD274033A5 (de)	1989-12-06
IE61485B1 (en)	1994-11-02
CA1318462C (en)	1993-05-25
EP0285562A2 (de)	1988-10-05
DE3880541D1 (de)	1993-06-03
GR3007996T3 (pt)	1993-08-31
FI90780C (fi)	1994-03-25
US4859736A (en)	1989-08-22
ATE88726T1 (de)	1993-05-15

Legal Events

Date	Code	Title	Description
1996-05-23	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD284031A5 (de)	1990-10-31	Verfahren zur herstellung eines kunstharzes
DE2616399C2 (de)	1986-03-27	Desamino-1,7-dicarbacalcitonine und Verfahren zu ihrer Herstellung
JP2001505872A (ja)	2001-05-08	α―ヒドロキシ酸リンカーを含むペプチドプロドラッグ
US6897289B1 (en)	2005-05-24	Peptide synthesis procedure in solid phase
EP0292729B1 (de)	1992-04-22	Neue Festphasen-Peptidsynthesemethoden
EP0394194B1 (de)	1993-08-18	Geschützte Aminosäuren und Verfahren zu ihrer Herstellung
DE69218193T2 (de)	1997-10-16	Verfahren zur Synthese von Peptiden, Derivate von Aminosäuren zur Verwendung bei dem obengenannten Verfahren und Methoden zu deren Herstellung.
DE69604759T2 (de)	2000-06-21	N alpha-2-(4-nitrophenylsulfonyl)ethoxycarbonyl-aminosäuren
DE3586940T2 (de)	1993-09-30	Polypeptid und dessen Verfahren zur Herstellung.
US4389342A (en)	1983-06-21	Synthetic hormone-like peptides and method for their synthesis
CH628323A5 (de)	1982-02-26	Verfahren zur herstellung von cholecystokinin-pancreozymin-octapeptidamid-sulfatester.
DE69017704T2 (de)	1995-07-20	Hexapeptide mit sulphat-ester-gruppen.
EP0443598B1 (de)	1995-05-17	Die Blutgerinnung inhibierende Peptide, Verfahren zu ihrer Herstellung und ihre Verwendung
JPH01197465A (ja)	1989-08-09	新規アルギニン誘導体、その製法及びペプチド合成における使用法
DE4404168A1 (de)	1995-08-17	Hirudinderivate und Verfahren zu deren Herstellung
DE2327634A1 (de)	1974-01-24	Nonapeptide und verfahren zu deren herstellung
US5502164A (en)	1996-03-26	Peptide compounds having therapeutic activity
DE2106139A1 (de)	1971-08-19	Die Herstellung von Peptiden
CH620671A5 (en)	1980-12-15	Process for the preparation of a peptide
DD299291A5 (de)	1992-04-09	Geschuetzte aminosaeuren und verfahren zu ihrer herstellung
JPS60226899A (ja)	1985-11-12	コノトキシン類縁体
CH498805A (de)	1970-11-15	Verfahren zur Herstellung von Cystinrest-haltigen Peptiden
DE2810860A1 (de)	1979-09-27	Verfahren zum aufbau von peptidketten
WO1996007671A1 (de)	1996-03-14	Racemisierungsfreie herstellung von n-aminosäure-derivaten und dipeptiden
DE3221818A1 (de)	1983-12-15	3,5-di-tert.-butylbenzyloxycarbonylderivate, verfahren zu ihrer herstellung und ihre verwendung