NO302482B1 - Polyaspartamid-derivater, konjugater av disse samt anvendelse av derivatene og konjugatene - Google Patents

Polyaspartamid-derivater, konjugater av disse samt anvendelse av derivatene og konjugatene Download PDF

Info

Publication number: NO302482B1
Authority: NO; Norway
Prior art keywords: acid; residue; aspartamide; bile; derivatives
Prior art date: 1991-12-20

Application number

NO924921A

Other languages

English (en)

Norwegian (no)

Other versions

NO924921L (no

NO924921D0 (no

Inventor

Volker Krone

Axel Walch

Stefan Muellner

Ernold Granzer

Original Assignee

Hoechst Ag

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.)

1991-12-20

Filing date

1992-12-18

Publication date

1998-03-09

1992-12-18 Application filed by Hoechst Ag filed Critical Hoechst Ag

1992-12-18 Publication of NO924921D0 publication Critical patent/NO924921D0/no

1993-06-21 Publication of NO924921L publication Critical patent/NO924921L/no

1998-03-09 Publication of NO302482B1 publication Critical patent/NO302482B1/no

Links

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RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 1
229960001091 chenodeoxycholic acid Drugs 0.000 description 1
201000001883 cholelithiasis Diseases 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
230000000112 colonic effect Effects 0.000 description 1
230000008602 contraction Effects 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
QLACLEPYLWLNTD-UHFFFAOYSA-N dihydrocinnamic acid Natural products COc1ccc(CCC(O)=O)c(O)c1OC QLACLEPYLWLNTD-UHFFFAOYSA-N 0.000 description 1
239000001177 diphosphate Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
230000005284 excitation Effects 0.000 description 1
229940125753 fibrate Drugs 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000001917 fluorescence detection Methods 0.000 description 1
235000019264 food flavour enhancer Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
210000000232 gallbladder Anatomy 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
229960002743 glutamine Drugs 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
229960003136 leucine Drugs 0.000 description 1
229960004488 linolenic acid Drugs 0.000 description 1
KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 description 1
210000001758 mesenteric vein Anatomy 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000021313 oleic acid Nutrition 0.000 description 1
229940116369 pancreatic lipase Drugs 0.000 description 1
230000009057 passive transport Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
229960003912 probucol Drugs 0.000 description 1
229960002429 proline Drugs 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000009467 reduction Effects 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
229960001153 serine Drugs 0.000 description 1
FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229960002898 threonine Drugs 0.000 description 1
229960004799 tryptophan Drugs 0.000 description 1
229960004441 tyrosine Drugs 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
229960004295 valine Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
- A61K47/645—Polycationic or polyanionic oligopeptides, polypeptides or polyamino acids, e.g. polylysine, polyarginine, polyglutamic acid or peptide TAT
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/10—Alpha-amino-carboxylic acids
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/36—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino acids, polyamines and polycarboxylic acids
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1092—Polysuccinimides

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Polymers & Plastics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Epidemiology (AREA)
Molecular Biology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Obesity (AREA)
General Chemical & Material Sciences (AREA)
Diabetes (AREA)
Hematology (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Polyamides (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Mobile Radio Communication Systems (AREA)
Transceivers (AREA)
Peptides Or Proteins (AREA)
Polyesters Or Polycarbonates (AREA)
Detergent Compositions (AREA)

NO924921A 1991-12-20 1992-12-18 Polyaspartamid-derivater, konjugater av disse samt anvendelse av derivatene og konjugatene NO302482B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4142147		1991-12-20

Publications (3)

Publication Number	Publication Date
NO924921D0 NO924921D0 (no)	1992-12-18
NO924921L NO924921L (no)	1993-06-21
NO302482B1 true NO302482B1 (no)	1998-03-09

Family

ID=6447596

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO924921A NO302482B1 (no)	1991-12-20	1992-12-18	Polyaspartamid-derivater, konjugater av disse samt anvendelse av derivatene og konjugatene

Country Status (11)

Country	Link
US (2)	US5714138A (fi)
EP (1)	EP0548794B1 (fi)
JP (1)	JPH0665372A (fi)
AT (1)	ATE180968T1 (fi)
CA (1)	CA2085782A1 (fi)
DE (1)	DE59209709D1 (fi)
DK (1)	DK0548794T3 (fi)
ES (1)	ES2134787T3 (fi)
FI (1)	FI925734L (fi)
GR (1)	GR3030882T3 (fi)
NO (1)	NO302482B1 (fi)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI925734L (fi) *	1991-12-20	1993-06-21	Hoechst Ag	Polyaspartamidderivat som adsorptionsmedel foer gallsyra, polyaspartamidderivat innehaollande gallsyror och foerfarande foer framstaellning av dessa samt anvaendning av dessa som laekemedel
DE69413590D1 (de) *	1993-04-23	1998-11-05	Rhone Poulenc Chimie	Polyanhydroasparaginsäure und seine bioabbaubaren Hydrolyseprodukte
US6262277B1 (en)	1994-09-13	2001-07-17	G.D. Searle And Company	Intermediates and processes for the preparation of benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
US6642268B2 (en)	1994-09-13	2003-11-04	G.D. Searle & Co.	Combination therapy employing ileal bile acid transport inhibiting benzothipines and HMG Co-A reductase inhibitors
US6268392B1 (en)	1994-09-13	2001-07-31	G. D. Searle & Co.	Combination therapy employing ileal bile acid transport inhibiting benzothiepines and HMG Co-A reductase inhibitors
US6107494A (en) *	1994-09-13	2000-08-22	G.D. Searle And Company	Substituted 5-aryl-benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
US5994391A (en) *	1994-09-13	1999-11-30	G.D. Searle And Company	Benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
WO2000038722A1 (en)	1998-12-23	2000-07-06	G.D. Searle & Co.	COMBINATIONS OF CHOLESTERYL ESTER TRANSFER PROTEIN INHIBITORS AND HMG CoA REDUCTASE INHIBITORS FOR CARDIOVASCULAR INDICATIONS
ATE241386T1 (de)	1998-12-23	2003-06-15	Searle Llc	Kombinationen von ileumgallensäuretransports inhibitoren und cholesteryl ester transfer protein inhibitoren
EP1140189B1 (en)	1998-12-23	2003-05-14	G.D. Searle LLC.	Combinations of ileal bile acid transport inhibitors and fibric acid derivatives for cardiovascular indications
ATE242007T1 (de)	1998-12-23	2003-06-15	Searle Llc	Kombinationen von cholesteryl ester transfer protein inhibitoren und nicotinsäure derivaten für kardiovaskuläre indikationen
AU2157500A (en)	1998-12-23	2000-07-31	G.D. Searle Llc	Combinations of cholesteryl ester transfer protein inhibitors and bile acid sequestering agents for cardiovascular indications
AU776664B2 (en)	1998-12-23	2004-09-16	G.D. Searle Llc	Combinations of cholesteryl ester transfer protein inhibitors and fibric acid derivatives for cardiovascular indications
DK1140190T3 (da)	1998-12-23	2002-12-23	Searle Llc	Kombinationer af ileumgaldesyretransport-inhibitorer og galdesyre-sekvestreringsmidler til cardiovaskulære indikatorer
AU2001240115A1 (en)	2000-03-10	2001-09-24	Pharmacia Corporation	Method for the preparation of tetrahydrobenzothiepines
CN1538985A (zh) *	2001-08-03	2004-10-20		用于洗涤剂组合物中的聚天冬氨酸衍生物
MXPA04003524A (es)	2001-11-02	2004-07-23	Searle Llc	Compuestos de benzotiepina monofluorados y difluorados novedosos como inhibidores de transporte de acido biliar co-dependiente de sodio apical (asbt) y captacion de taurocolato.
MXPA04006255A (es)	2002-01-17	2004-09-27	Pharmacia Corp	Compuestos novedosos de alquil/aril hidroxi o ceto tiepina como inhibidores del transporte del acido biliar codependiente del sodio apical y la captacion de taurocolato.
FR2837710B1 (fr) *	2002-03-26	2005-07-08	Innovations Pharma Ag	Composition topique a base de resines echangeuses d'ions, notamment pour le traitement des erythemes
CN108264639B (zh) *	2017-12-20	2020-08-07	湖北工业大学	一种温度pH双重响应性肉桂酸-聚天冬酰胺扼合物及其水相交联方法

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB747901A (en) *	1953-07-01	1956-04-18	Courtaulds Ltd	Improvements in and relating to the treatment of synthetic polypeptides
GB1024393A (en) *	1963-03-30	1966-03-30	Asahi Chemical Ind	Process for polymerizing n-carboxy-ª-amino acid anhydrides
GB1202765A (en) *	1967-07-20	1970-08-19	Kyowa Hakko Kogyo Kk	PROCESS FOR THE POLYMERIZATION OF alpha-AMINO ACID-N-CARBOXY ANHYDRIDES
US3846380A (en) *	1972-10-31	1974-11-05	M Teranishi	Polyamino acid derivatives and compositions containing same
GB1506217A (en) *	1975-08-26	1978-04-05	Taiho Pharmaceutical Co Ltd	Oral antilipemic composition
US4363797A (en) *	1977-09-14	1982-12-14	Societe Anonyme Dite: L'oreal	Polyaspartic acid derivatives, their preparation and their use in cosmetic composition
FR2424293A1 (fr) *	1978-04-27	1979-11-23	Oreal	Nouveau procede de preparation de l'acide polydehydroaspartique
JPS6086124A (ja) *	1983-10-17	1985-05-15	Nitto Boseki Co Ltd	規則性ポリアミノ酸樹脂の製造方法
DE3626672A1 (de) *	1986-08-07	1988-02-11	Bayer Ag	Polyasparaginamidsaeure
DE3700128A1 (de) *	1987-01-03	1988-07-14	Hoechst Ag	Biologisch abbaubare poly- (hydroxyalkyl)- aminodicarbonsaeure-derivate, verfahren zu ihrer herstellung und verwendung derselben fuer depotzubereitungen mit kontrollierter wirkstoffabgabe
US5516758A (en) *	1989-03-23	1996-05-14	Berlex Laboratories, Inc.	Polyamides bearing functionalized side chains useful as water soluble hypolipidemic agents
JP2909500B2 (ja) *	1989-03-23	1999-06-23	ベルレックス、ラボラトリーズ、レンコーポレイテッド	水溶性抗高脂質血症剤として有用な官能化側鎖を有するポリアミド
DE4002736A1 (de) *	1990-01-31	1991-08-01	Hoechst Ag	Biologisch abbaubare polymere, verfahren zu ihrer herstellung und verwendung derselben fuer depotzubereitungen mit kontrollierter wirkstoffabgabe
US5190982A (en) *	1990-04-26	1993-03-02	Hoechst Aktiengesellschaft	Ultrasonic contrast agents, processes for their preparation and the use thereof as diagnostic and therapeutic agents
CA2040996A1 (en) *	1990-05-02	1991-11-03	Robert L. Albright	Composition and method for controlling cholesterol
US5057597A (en) *	1990-07-03	1991-10-15	Koskan Larry P	Process for the manufacture of anhydro polyamino acids and polyamino acids
FI925734L (fi) *	1991-12-20	1993-06-21	Hoechst Ag	Polyaspartamidderivat som adsorptionsmedel foer gallsyra, polyaspartamidderivat innehaollande gallsyror och foerfarande foer framstaellning av dessa samt anvaendning av dessa som laekemedel

1992
- 1992-12-17 FI FI925734A patent/FI925734L/fi unknown
- 1992-12-17 ES ES92121461T patent/ES2134787T3/es not_active Expired - Lifetime
- 1992-12-17 DE DE59209709T patent/DE59209709D1/de not_active Expired - Fee Related
- 1992-12-17 EP EP92121461A patent/EP0548794B1/de not_active Expired - Lifetime
- 1992-12-17 AT AT92121461T patent/ATE180968T1/de not_active IP Right Cessation
- 1992-12-17 DK DK92121461T patent/DK0548794T3/da active
- 1992-12-18 CA CA002085782A patent/CA2085782A1/en not_active Abandoned
- 1992-12-18 NO NO924921A patent/NO302482B1/no not_active IP Right Cessation
- 1992-12-18 JP JP4337736A patent/JPH0665372A/ja active Pending
1993
- 1993-12-10 US US08/164,767 patent/US5714138A/en not_active Expired - Fee Related
1997
- 1997-10-22 US US08/956,122 patent/US6036948A/en not_active Expired - Fee Related
1999
- 1999-07-30 GR GR990401963T patent/GR3030882T3/el unknown

Also Published As

Publication number	Publication date
DE59209709D1 (de)	1999-07-15
US5714138A (en)	1998-02-03
FI925734A0 (fi)	1992-12-17
EP0548794A2 (de)	1993-06-30
EP0548794B1 (de)	1999-06-09
GR3030882T3 (en)	1999-11-30
JPH0665372A (ja)	1994-03-08
DK0548794T3 (da)	1999-12-06
CA2085782A1 (en)	1993-06-21
US6036948A (en)	2000-03-14
ATE180968T1 (de)	1999-06-15
NO924921L (no)	1993-06-21
NO924921D0 (no)	1992-12-18
EP0548794A3 (en)	1994-11-23
ES2134787T3 (es)	1999-10-16
FI925734L (fi)	1993-06-21

Publication	Publication Date	Title
NO302482B1 (no)	1998-03-09	Polyaspartamid-derivater, konjugater av disse samt anvendelse av derivatene og konjugatene
AU624215B2 (en)	1992-06-04	Alkylated polyethylenimine derivatives, process for their preparation, their use as pharmaceuticals and pharmaceutical preparations
CA2085831C (en)	2006-05-30	Polymers and oligomers of bile acid derivatives, process for their preparation and their use as pharmaceuticals
KR100314496B1 (ko)	2001-11-22	항혈전성이 있는 헤파린 유도체, 그의 제조방법 및 용도
Lee et al.	1999	Modification of chitosan to improve its hypocholesterolemic capacity
Maeda et al.	1988	H+-induced release of contents of phosphatidylcholine vesicles bearing surface-bound polyelectrolyte chains
JP2000517356A (ja)	2000-12-26	併発胆汁酸吸着作用を有する高分子量胆汁酸吸収阻害剤
JPH06157671A (ja)	1994-06-07	架橋、窒素含有ビニルコポリマー、その製造方法およびこれらの化合物の用途
Ventura et al.	1997	Improvement of water solubility and dissolution rate of ursodeoxycholic acid and chenodeoxycholic acid by complexation with natural and modified β-cyclodextrins
JPH069686A (ja)	1994-01-18	胆汁酸を濃縮するためのアルキル化ポリエチレンイミン誘導体の使用
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