DE2032470A1 - Verfahren zur Herstellung von alpha beta Poly (asparaginsäure) hydroxyalkyl amiden und ihre therapeutische Verwendung - Google Patents
Verfahren zur Herstellung von alpha beta Poly (asparaginsäure) hydroxyalkyl amiden und ihre therapeutische VerwendungInfo
- Publication number
- DE2032470A1 DE2032470A1 DE19702032470 DE2032470A DE2032470A1 DE 2032470 A1 DE2032470 A1 DE 2032470A1 DE 19702032470 DE19702032470 DE 19702032470 DE 2032470 A DE2032470 A DE 2032470A DE 2032470 A1 DE2032470 A1 DE 2032470A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- formula
- reaction
- anhydropolyaspartic
- solvent
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 33
- 229920000805 Polyaspartic acid Polymers 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 7
- 230000001225 therapeutic effect Effects 0.000 title description 2
- -1 hydroxyalkyl amides Chemical class 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 150000001414 amino alcohols Chemical class 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 239000007822 coupling agent Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 4
- 235000003704 aspartic acid Nutrition 0.000 claims description 4
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 238000001990 intravenous administration Methods 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000006731 degradation reaction Methods 0.000 claims description 2
- 238000005194 fractionation Methods 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 231100000053 low toxicity Toxicity 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 238000005897 peptide coupling reaction Methods 0.000 claims description 2
- 238000012719 thermal polymerization Methods 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 1
- 206010044541 Traumatic shock Diseases 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 229920002307 Dextran Polymers 0.000 description 4
- 208000032843 Hemorrhage Diseases 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 230000000740 bleeding effect Effects 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-UHFFFAOYSA-N Aspartic acid Chemical compound OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010021138 Hypovolaemic shock Diseases 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- 208000005374 Poisoning Diseases 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000001698 pyrogenic effect Effects 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 206010040560 shock Diseases 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000032456 Hemorrhagic Shock Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010049771 Shock haemorrhagic Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- AZHSSKPUVBVXLK-UHFFFAOYSA-N ethane-1,1-diol Chemical compound CC(O)O AZHSSKPUVBVXLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000000108 ultra-filtration Methods 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
- 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
- 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
- C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
-
- 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
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Polyamides (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT4667/69A IT1045109B (it) | 1969-07-03 | 1969-07-03 | Foli idrossi etil asparagina e metodo per la sua produzione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2032470A1 true DE2032470A1 (de) | 1971-01-14 |
Family
ID=11112821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702032470 Pending DE2032470A1 (de) | 1969-07-03 | 1970-07-01 | Verfahren zur Herstellung von alpha beta Poly (asparaginsäure) hydroxyalkyl amiden und ihre therapeutische Verwendung |
Country Status (11)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0439846A1 (de) * | 1990-01-31 | 1991-08-07 | Hoechst Aktiengesellschaft | Biologisch abbaubare Polymere, Verfahren zu ihrer Herstellung und Verwendung derselben für Depotzubereitungen mit kontrollierter Wirkstoffabgabe |
| EP0389079A3 (en) * | 1989-03-23 | 1991-08-07 | Berlex Laboratories, Inc. | Polyamides bearing functionalized side chains useful as water soluble hypolipidemic agents |
| EP0519119A1 (en) * | 1991-06-18 | 1992-12-23 | Berlex Laboratories, Inc. | Polyamides bearing functionalized side chains useful as water soluble hypolipidemic agents |
| FR2725723A1 (fr) * | 1994-10-12 | 1996-04-19 | Rhone Poulenc Chimie | Procede de preparation de polycondensats d'aminoacides et de leurs hydrolysats polypeptidiques biodegradables et leur utilisation dans les compositions detergentes |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2424293A1 (fr) * | 1978-04-27 | 1979-11-23 | Oreal | Nouveau procede de preparation de l'acide polydehydroaspartique |
| FR2457306A1 (fr) | 1979-05-25 | 1980-12-19 | Oreal | Nouveaux produits colorants, leur preparation et leur utilisation dans des compositions colorantes |
| US4526888A (en) * | 1983-04-29 | 1985-07-02 | Bristol-Myers Company | Nephrotoxicity inhibitors for aminoglycoside antibiotics |
| CS252559B1 (en) * | 1985-03-22 | 1987-09-17 | Frantisek Rypacek | Polymer stabilizer of emulsion type water in oil |
| US5371177A (en) * | 1992-07-10 | 1994-12-06 | Rohm And Haas Company | Process for preparing polysuccinimides from maleamic acid |
| ES2161747T3 (es) * | 1993-11-24 | 2001-12-16 | Rhodia Chimie Sa | Procedimiento de preparacion de poliimidas o de sus hidrolizados polipeptidicos biodegradables. |
| FR2712892B1 (fr) * | 1993-11-24 | 1995-12-22 | Rhone Poulenc Chimie | Procédé de préparation de polyimides ou de leurs hydrolysats biodégradables. |
| JPH09165447A (ja) | 1995-12-15 | 1997-06-24 | Mitsubishi Chem Corp | ポリアスパラギン酸共重合体及びその製造方法 |
| JP3978363B2 (ja) | 2001-04-23 | 2007-09-19 | ユニ・チャーム株式会社 | パンツ型の使い捨て着用物品 |
| JP2004216082A (ja) | 2003-01-10 | 2004-08-05 | Uni Charm Corp | パンツ型の使い捨て着用物品 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2866783A (en) * | 1956-07-05 | 1958-12-30 | Bovarnick Max | Glutamic and aspartic acid polypeptide polymers as plasma volume extenders |
-
1969
- 1969-07-03 IT IT4667/69A patent/IT1045109B/it active
-
1970
- 1970-06-25 ZA ZA704382A patent/ZA704382B/xx unknown
- 1970-06-26 GB GB3106570A patent/GB1319103A/en not_active Expired
- 1970-06-30 CH CH987970A patent/CH569733A5/xx not_active IP Right Cessation
- 1970-07-01 DE DE19702032470 patent/DE2032470A1/de active Pending
- 1970-07-02 JP JP45057357A patent/JPS4820638B1/ja active Pending
- 1970-07-02 DK DK345370A patent/DK132708C/da active
- 1970-07-02 BE BE752909D patent/BE752909A/xx unknown
- 1970-07-03 FR FR7024831A patent/FR2059475B1/fr not_active Expired
- 1970-07-03 SE SE09311/70A patent/SE364702B/xx unknown
- 1970-07-03 NL NL7009874A patent/NL7009874A/xx unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0389079A3 (en) * | 1989-03-23 | 1991-08-07 | Berlex Laboratories, Inc. | Polyamides bearing functionalized side chains useful as water soluble hypolipidemic agents |
| EP0439846A1 (de) * | 1990-01-31 | 1991-08-07 | Hoechst Aktiengesellschaft | Biologisch abbaubare Polymere, Verfahren zu ihrer Herstellung und Verwendung derselben für Depotzubereitungen mit kontrollierter Wirkstoffabgabe |
| EP0519119A1 (en) * | 1991-06-18 | 1992-12-23 | Berlex Laboratories, Inc. | Polyamides bearing functionalized side chains useful as water soluble hypolipidemic agents |
| FR2725723A1 (fr) * | 1994-10-12 | 1996-04-19 | Rhone Poulenc Chimie | Procede de preparation de polycondensats d'aminoacides et de leurs hydrolysats polypeptidiques biodegradables et leur utilisation dans les compositions detergentes |
| US5688903A (en) * | 1994-10-12 | 1997-11-18 | Rhone-Poulenc Chimie | Process for the preparation of polycondensates of amino acids and the biodegradable polypeptide hydrolysates thereof, and their use in detergent compositions |
| US5824765A (en) * | 1994-10-12 | 1998-10-20 | Rhone-Poulenc Chimie | Preparation of polycondensates of amino acids and the biodegradable polypeptide hydrolysates thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2059475B1 (enrdf_load_stackoverflow) | 1975-04-18 |
| DK132708B (da) | 1976-01-26 |
| BE752909A (fr) | 1970-12-16 |
| IT1045109B (it) | 1980-05-10 |
| ZA704382B (en) | 1971-03-31 |
| NL7009874A (enrdf_load_stackoverflow) | 1971-01-05 |
| GB1319103A (en) | 1973-06-06 |
| CH569733A5 (enrdf_load_stackoverflow) | 1975-11-28 |
| DK132708C (da) | 1976-07-05 |
| FR2059475A1 (enrdf_load_stackoverflow) | 1971-06-04 |
| JPS4820638B1 (enrdf_load_stackoverflow) | 1973-06-22 |
| SE364702B (enrdf_load_stackoverflow) | 1974-03-04 |
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