CA2045073A1 - Composition et traitement a base de peptides biologiquement actifs et d'antibiotiques qui inhibent l'adn-gyrase - Google Patents

Composition et traitement a base de peptides biologiquement actifs et d'antibiotiques qui inhibent l'adn-gyrase

Info

Publication number: CA2045073A1
Authority: CA; Canada
Prior art keywords: peptide; amino acid; basic; hydrophobic; antibiotic
Prior art date: 1990-06-27
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.): Abandoned

Application number

CA002045073A

Other languages

English (en)

Inventor

Barry Berkowitz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Magainin Pharmaceuticals Inc

Original Assignee

Individual

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.)

1990-06-27

Filing date

1991-06-20

Publication date

1991-12-28

1991-06-20 Application filed by Individual filed Critical Individual

1991-12-28 Publication of CA2045073A1 publication Critical patent/CA2045073A1/fr

Status Abandoned legal-status Critical Current

Links

108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 159
239000000203 mixture Substances 0.000 title claims abstract description 46
239000003242 anti bacterial agent Substances 0.000 title claims abstract description 15
102000004196 processed proteins & peptides Human genes 0.000 title claims description 27
229940088710 antibiotic agent Drugs 0.000 title description 5
108010054814 DNA Gyrase Proteins 0.000 claims abstract description 56
230000003115 biocidal effect Effects 0.000 claims abstract description 47
102000004169 proteins and genes Human genes 0.000 claims abstract description 43
108090000623 proteins and genes Proteins 0.000 claims abstract description 43
241000894006 Bacteria Species 0.000 claims abstract description 5
150000001413 amino acids Chemical class 0.000 claims description 119
230000002209 hydrophobic effect Effects 0.000 claims description 64
230000007935 neutral effect Effects 0.000 claims description 29
108060003100 Magainin Proteins 0.000 claims description 24
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 21
KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 claims description 15
229920001184 polypeptide Polymers 0.000 claims description 14
108020004414 DNA Proteins 0.000 claims description 12
229960003405 ciprofloxacin Drugs 0.000 claims description 10
150000002500 ions Chemical class 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
239000003306 quinoline derived antiinfective agent Substances 0.000 claims description 9
101800004819 PGLa Proteins 0.000 claims description 8
108050004290 Cecropin Proteins 0.000 claims description 7
229960000321 oxolinic acid Drugs 0.000 claims description 6
229960000210 nalidixic acid Drugs 0.000 claims description 5
MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical group C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
101500009721 Xenopus laevis Magainin-2 Proteins 0.000 claims description 2
MGIUUAHJVPPFEV-ABXDCCGRSA-N magainin ii Chemical group C([C@H](NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(O)=O)C1=CC=CC=C1 MGIUUAHJVPPFEV-ABXDCCGRSA-N 0.000 claims description 2
235000001014 amino acid Nutrition 0.000 claims 74
235000018102 proteins Nutrition 0.000 claims 10
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 4
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical group OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 4
235000003704 aspartic acid Nutrition 0.000 claims 4
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Chemical group OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 4
229960004621 cinoxacin Drugs 0.000 claims 4
VDUWPHTZYNWKRN-UHFFFAOYSA-N cinoxacin Chemical group C1=C2N(CC)N=C(C(O)=O)C(=O)C2=CC2=C1OCO2 VDUWPHTZYNWKRN-UHFFFAOYSA-N 0.000 claims 4
235000013922 glutamic acid Nutrition 0.000 claims 4
239000004220 glutamic acid Substances 0.000 claims 4
125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
229910052749 magnesium Inorganic materials 0.000 claims 1
239000011777 magnesium Substances 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 31
239000002253 acid Substances 0.000 description 26
150000007513 acids Chemical class 0.000 description 12
OBMZMSLWNNWEJA-XNCRXQDQSA-N C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 Chemical compound C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 OBMZMSLWNNWEJA-XNCRXQDQSA-N 0.000 description 9
101710176384 Peptide 1 Proteins 0.000 description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
VZQHRKZCAZCACO-PYJNHQTQSA-N (2s)-2-[[(2s)-2-[2-[[(2s)-2-[[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]propanoyl]amino]prop-2-enoylamino]-3-methylbutanoyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C(C)C)NC(=O)C(=C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCCNC(N)=N VZQHRKZCAZCACO-PYJNHQTQSA-N 0.000 description 6
239000002674 ointment Substances 0.000 description 5
SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
239000000463 material Substances 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
108020000946 Bacterial DNA Proteins 0.000 description 2
108010002069 Defensins Proteins 0.000 description 2
102000000541 Defensins Human genes 0.000 description 2
241000521257 Hydrops Species 0.000 description 2
102000004310 Ion Channels Human genes 0.000 description 2
241001024304 Mino Species 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
102000004503 Perforin Human genes 0.000 description 2
108010056995 Perforin Proteins 0.000 description 2
108010011559 alanylphenylalanine Proteins 0.000 description 2
230000000845 anti-microbial effect Effects 0.000 description 2
239000004599 antimicrobial Substances 0.000 description 2
238000003556 assay Methods 0.000 description 2
108010032816 bactericidal permeability increasing protein Proteins 0.000 description 2
102000052586 bactericidal permeability increasing protein Human genes 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000002555 ionophore Substances 0.000 description 2
230000000236 ionophoric effect Effects 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
244000005700 microbiome Species 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
239000001974 tryptic soy broth Substances 0.000 description 2
108010050327 trypticase-soy broth Proteins 0.000 description 2
PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 description 1
QKDHBVNJCZBTMR-LLVKDONJSA-N (R)-temafloxacin Chemical compound C1CN[C@H](C)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1F QKDHBVNJCZBTMR-LLVKDONJSA-N 0.000 description 1
GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 1
OMNVYXHOSHNURL-WPRPVWTQSA-N Ala-Phe Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 OMNVYXHOSHNURL-WPRPVWTQSA-N 0.000 description 1
YCRAFFCYWOUEOF-DLOVCJGASA-N Ala-Phe-Ser Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)C)CC1=CC=CC=C1 YCRAFFCYWOUEOF-DLOVCJGASA-N 0.000 description 1
101000600602 Aspergillus flavus (strain ATCC MYA-384 / AF70) Endopolygalacturonase A Proteins 0.000 description 1
101000600608 Aspergillus flavus (strain ATCC MYA-384 / AF70) Endopolygalacturonase B Proteins 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
101710112752 Cytotoxin Proteins 0.000 description 1
101100321992 Drosophila melanogaster ABCD gene Proteins 0.000 description 1
101100396994 Drosophila melanogaster Inos gene Proteins 0.000 description 1
101100285518 Drosophila melanogaster how gene Proteins 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
101000951145 Homo sapiens Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial Proteins 0.000 description 1
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
239000004183 Monensin A Substances 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
KHGNFPUMBJSZSM-UHFFFAOYSA-N Perforine Natural products COC1=C2CCC(O)C(CCC(C)(C)O)(OC)C2=NC2=C1C=CO2 KHGNFPUMBJSZSM-UHFFFAOYSA-N 0.000 description 1
208000037062 Polyps Diseases 0.000 description 1
101710093543 Probable non-specific lipid-transfer protein Proteins 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
101800001693 R-peptide Proteins 0.000 description 1
101001126848 Rhizobium radiobacter Polygalacturonase Proteins 0.000 description 1
SBMNPABNWKXNBJ-BQBZGAKWSA-N Ser-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CO SBMNPABNWKXNBJ-BQBZGAKWSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
102100038014 Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial Human genes 0.000 description 1
102000018568 alpha-Defensin Human genes 0.000 description 1
108050007802 alpha-defensin Proteins 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000000601 blood cell Anatomy 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940088516 cipro Drugs 0.000 description 1
231100000599 cytotoxic agent Toxicity 0.000 description 1
239000002619 cytotoxin Substances 0.000 description 1
-1 enoxac~l Chemical compound 0.000 description 1
210000003979 eosinophil Anatomy 0.000 description 1
239000000945 filler Substances 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
108091005128 magainin I Proteins 0.000 description 1
OFIZOVDANLLTQD-ZVNXOKPXSA-N magainin i Chemical compound C([C@H](NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(O)=O)C1=CC=CC=C1 OFIZOVDANLLTQD-ZVNXOKPXSA-N 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229960001699 ofloxacin Drugs 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
239000006072 paste Substances 0.000 description 1
229960004236 pefloxacin Drugs 0.000 description 1
FHFYDNQZQSQIAI-UHFFFAOYSA-N pefloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 FHFYDNQZQSQIAI-UHFFFAOYSA-N 0.000 description 1
229930192851 perforin Natural products 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
230000010076 replication Effects 0.000 description 1
230000003362 replicative effect Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960004576 temafloxacin Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Gastroenterology & Hepatology (AREA)
Epidemiology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Immunology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Organic Chemistry (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Zoology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002045073A 1990-06-27 1991-06-20 Composition et traitement a base de peptides biologiquement actifs et d'antibiotiques qui inhibent l'adn-gyrase Abandoned CA2045073A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US54535690A	1990-06-27	1990-06-27
US545,356		1990-06-27

Publications (1)

Publication Number	Publication Date
CA2045073A1 true CA2045073A1 (fr)	1991-12-28

Family

ID=24175898

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002045073A Abandoned CA2045073A1 (fr)	1990-06-27	1991-06-20	Composition et traitement a base de peptides biologiquement actifs et d'antibiotiques qui inhibent l'adn-gyrase

Country Status (4)

Country	Link
EP (1)	EP0559647A1 (fr)
JP (1)	JPH05507718A (fr)
CA (1)	CA2045073A1 (fr)
WO (1)	WO1992000090A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6348445B1 (en)	1992-06-01	2002-02-19	Magainin Pharmaceuticals, Inc.	Biologically active peptides with reduced toxicity in animals and a method for preparing same
US5654274A (en) *	1992-06-01	1997-08-05	Magainin Pharmaceuticals, Inc.	Biologically active peptides having N-terminal substitutions
US5733872A (en) *	1993-03-12	1998-03-31	Xoma Corporation	Biologically active peptides from functional domains of bactericidal/permeability-increasing protein and uses thereof

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE436645C (sv) *	1976-04-29	1996-07-22	Bonnierfoeretagen Ab	Antigeniskt aktiv polypeptid, som kan användas vid cancerdiagnosticering och vid framställning av antikroppar
US4659692A (en) *	1982-11-19	1987-04-21	The Regents Of The University Of California	Cationic oligopeptides having microbicidal activity
DE3324534A1 (de) *	1983-07-07	1985-01-17	Ciba-Geigy Ag, Basel	Modifizierte protease-inhibitoren, verfahren zu ihrer herstellung und daraus bereitete pharmazeutische mittel
US4617149A (en) *	1983-09-21	1986-10-14	Eli Lilly And Company	Growth hormone release factor analogs
DE3438296A1 (de) *	1984-04-18	1985-11-07	Hoechst Ag, 6230 Frankfurt	Neue polypeptide mit blutgerinnungshemmender wirkung, verfahren zu deren herstellung bzw. gewinnung, deren verwendung und diese enthaltende mittel
EP0209061B1 (fr) *	1985-07-17	1994-01-12	Hoechst Aktiengesellschaft	Peptides à activité anticoagulante, leur procédé de préparation, d'obtention, leur application et les agents les contenant
EP0362209B1 (fr) *	1987-03-04	1994-06-08	THE UNITED STATES OF AMERICA as represented by the Secretary United States Department of Commerce	Composes bioactifs synthetiques nouveaux et procede d'obtention d'effets bioactifs

1991
- 1991-06-20 WO PCT/US1991/004453 patent/WO1992000090A1/fr not_active Ceased
- 1991-06-20 CA CA002045073A patent/CA2045073A1/fr not_active Abandoned
- 1991-06-20 JP JP91511793A patent/JPH05507718A/ja active Pending
- 1991-06-20 EP EP91912701A patent/EP0559647A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
WO1992000090A1 (fr)	1992-01-09
EP0559647A1 (fr)	1993-09-15
JPH05507718A (ja)	1993-11-04
EP0559647A4 (fr)	1993-07-15

Legal Events

Date	Code	Title	Description
1993-01-29	EEER	Examination request
1995-12-20	FZDE	Dead

Publication	Publication Date	Title
US5221664A (en)	1993-06-22	Composition and treatment with biologically active peptides and toxic cations
Lundy et al.	2020	Natural antimicrobials in the dental pulp
CA2086111A1 (fr)	1992-11-11	Compositions a base de peptides bioactifs et utilisations
US5792831A (en)	1998-08-11	Analogues of magainin peptides containing D-amino acids
US5208220A (en)	1993-05-04	Composition and treatment with biologically active peptides and antibiotics which inhibit DNA gyrase
US5217956A (en)	1993-06-08	Composition and treatment with biologically active peptides and certain anions
CA2107674A1 (fr)	1992-10-09	Nouvelles compositions peptidiques et leur utilisation
US5225399A (en)	1993-07-06	Antimicrobial amphiphilic peptides
CA2125494A1 (fr)	1993-06-24	Traitement a l'aide d'une composition a base de peptides et d'agents de chelation biologiquement actifs
EP0590044A4 (en)	1996-06-12	Composition and treatment with biologically active peptides having c-terminal substitutions
EP0441832B1 (fr)	1994-06-15	Composition et traitement a l'aide et peptides a activite biologique et certains anions
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