CA2023194A1 - Peptides having bradykinin antagonist action - Google Patents
Peptides having bradykinin antagonist actionInfo
- Publication number
- CA2023194A1 CA2023194A1 CA002023194A CA2023194A CA2023194A1 CA 2023194 A1 CA2023194 A1 CA 2023194A1 CA 002023194 A CA002023194 A CA 002023194A CA 2023194 A CA2023194 A CA 2023194A CA 2023194 A1 CA2023194 A1 CA 2023194A1
- Authority
- CA
- Canada
- Prior art keywords
- peptides
- amino acid
- bradykinin
- stands
- direct bond
- 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.)
- Granted
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title abstract 4
- 102000004196 processed proteins & peptides Human genes 0.000 title abstract 4
- UYRCOTSOPWOSJK-JXTBTVDRSA-N bradykinin antagonist Chemical compound C1C2=CC=CC=C2CC1[C@@H](NC(=O)C(CO)NC(=O)C(NC(=O)CNC(=O)[C@H]1N(C[C@H](O)C1)C(=O)C1N(CCC1)C(=O)C(CCCNC(N)=N)NC(=O)[C@@H](CCCNC(N)=N)NC(=N)CCCCCCC(=N)N[C@H](CCCNC(N)=N)C(=O)NC(CCCNC(N)=N)C(=O)N1C(CCC1)C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)NCC(=O)NC(C1CC2=CC=CC=C2C1)C(=O)NC(CO)C(=O)N[C@H](C1CC2=CC=CC=C2C1)C(=O)N1C2CCCCC2CC1C(=O)NC(CCCNC(N)=N)C(O)=O)C1CC2=CC=CC=C2C1)C(=O)N1C2CCCCC2CC1C(=O)NC(CCCNC(=N)N)C(O)=O UYRCOTSOPWOSJK-JXTBTVDRSA-N 0.000 title abstract 3
- 239000003152 bradykinin antagonist Substances 0.000 title abstract 3
- 150000001413 amino acids Chemical class 0.000 abstract 4
- 101800004538 Bradykinin Proteins 0.000 abstract 1
- 102400000967 Bradykinin Human genes 0.000 abstract 1
- 101710097732 Bradykinin-related peptides Proteins 0.000 abstract 1
- 108010016626 Dipeptides Proteins 0.000 abstract 1
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- -1 aromatic amino acid Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000001575 pathological effect Effects 0.000 abstract 1
- 238000010647 peptide synthesis reaction Methods 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 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
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- 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
- C07K7/18—Kallidins; Bradykinins; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Peptides having bradykinin antagonist action Peptides of the formula I
A-B-C-E-F-K-(D)-Phe-G-M-F'-I (I) in which A stands for hydrogen, alkyl, alkanoyl, alkoxy-carbonyl, alkylsulfonyl, cycloalkyl, aryl, aryloyl, arylsulfonyl, heteroaryl or an amino acid which may optionally be substituted, B is a basic amino acid, C
denotes a dipeptide or tripeptide, E stands for the radical of an aromatic amino acid, F independently of one another denotes an amino acid which is optionally sub-stituted in the side chain or a direct bond, G is an amino acid, F' is as defined far F, -NH-(CH2)2-3 or may optionally denote a direct bond, T is -OH, -NH2 or -NHC2H5 and K denotes a radical -NH- (CH2)1-4 -CO- or stands for a direct bond, have bradykinin antagonist action. Their therapeutic utility includes all pathological states which are mediated, caused or supported by bradykinin and bradykinin-related peptides. The peptides of the formula I are prepared by known methods of peptide synthesis.
A-B-C-E-F-K-(D)-Phe-G-M-F'-I (I) in which A stands for hydrogen, alkyl, alkanoyl, alkoxy-carbonyl, alkylsulfonyl, cycloalkyl, aryl, aryloyl, arylsulfonyl, heteroaryl or an amino acid which may optionally be substituted, B is a basic amino acid, C
denotes a dipeptide or tripeptide, E stands for the radical of an aromatic amino acid, F independently of one another denotes an amino acid which is optionally sub-stituted in the side chain or a direct bond, G is an amino acid, F' is as defined far F, -NH-(CH2)2-3 or may optionally denote a direct bond, T is -OH, -NH2 or -NHC2H5 and K denotes a radical -NH- (CH2)1-4 -CO- or stands for a direct bond, have bradykinin antagonist action. Their therapeutic utility includes all pathological states which are mediated, caused or supported by bradykinin and bradykinin-related peptides. The peptides of the formula I are prepared by known methods of peptide synthesis.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3926822A DE3926822A1 (en) | 1989-08-14 | 1989-08-14 | PEPTIDES WITH BRADYKININ ANTAGONISTIC EFFECT |
| DEP3926822.5 | 1989-08-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2023194A1 true CA2023194A1 (en) | 1991-02-15 |
| CA2023194C CA2023194C (en) | 2001-09-11 |
Family
ID=6387091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002023194A Expired - Lifetime CA2023194C (en) | 1989-08-14 | 1990-08-13 | Peptides having bradykinin antagonist action |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0413277B1 (en) |
| JP (1) | JP2997519B2 (en) |
| KR (1) | KR0173976B1 (en) |
| CN (1) | CN1034577C (en) |
| AT (1) | ATE114320T1 (en) |
| AU (1) | AU638735B2 (en) |
| CA (1) | CA2023194C (en) |
| CY (1) | CY2029A (en) |
| CZ (1) | CZ284783B6 (en) |
| DD (1) | DD297169A5 (en) |
| DE (2) | DE3926822A1 (en) |
| DK (1) | DK0413277T3 (en) |
| ES (1) | ES2065445T3 (en) |
| FI (1) | FI102759B1 (en) |
| HU (1) | HU208324B (en) |
| IE (1) | IE65356B1 (en) |
| IL (1) | IL95357A (en) |
| LT (1) | LT3868B (en) |
| NO (1) | NO178433C (en) |
| NZ (1) | NZ234861A (en) |
| PT (1) | PT94982B (en) |
| RU (1) | RU2081880C1 (en) |
| SK (1) | SK280787B6 (en) |
| ZA (1) | ZA906381B (en) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4013270A1 (en) * | 1990-04-26 | 1991-10-31 | Hoechst Ag | PEPTIDES WITH BRADYKININ ANTAGONISTIC EFFECT |
| WO1992017201A1 (en) * | 1991-04-01 | 1992-10-15 | Cortech, Inc. | Bradykinin antagonists |
| US6770741B1 (en) | 1991-04-19 | 2004-08-03 | Scios Inc. | Bradykinin antagonist peptides |
| ATE169823T1 (en) * | 1991-04-19 | 1998-09-15 | Scios Nova Inc | BRADYKININ TYPICAL PEPTIDES |
| CA2106762C (en) * | 1991-04-19 | 2000-10-10 | Donald J. Kyle | Bradykinin antagonist peptides |
| US5380875A (en) * | 1991-06-06 | 1995-01-10 | Hitachi Chemical Company, Ltd. | Hydroxyproline derivatives and preparative process therefor |
| WO1993011789A1 (en) | 1991-12-12 | 1993-06-24 | Scios Nova Inc. | Modified position (7) bradykinin antagonist peptides |
| TW199863B (en) * | 1991-12-21 | 1993-02-11 | Hoechst Ag | |
| TW258739B (en) * | 1992-04-04 | 1995-10-01 | Hoechst Ag | |
| US5541286A (en) * | 1992-10-08 | 1996-07-30 | Scios Nova Inc. | Bradykinin antagonist pseudopeptide derivatives of olefinic aminoalkanoic acids |
| US5521158A (en) * | 1992-10-08 | 1996-05-28 | Scios Nova Inc. | Pseudopeptide bradykinin receptor antagonists |
| US5610142A (en) * | 1992-10-08 | 1997-03-11 | Scios Inc. | Bradykinin antagonist pseudopeptide derivatives of substituted 4-keto-1,3,8-triazaspiro[4.5]decan-3-alkanoic acids |
| US5686565A (en) * | 1992-10-08 | 1997-11-11 | Scios Inc. | Bradykinin antagonist pseudopeptide derivatives of aminoalkanoic acids and related olefins |
| WO1994019372A1 (en) * | 1993-02-17 | 1994-09-01 | Scios Nova Inc. | Cyclic bradykinin antagonist peptides |
| US5817756A (en) * | 1993-09-09 | 1998-10-06 | Scios Inc. | Pseudo- and non-peptide bradykinin receptor antagonists |
| FR2739553B1 (en) * | 1995-10-06 | 1998-01-02 | Oreal | USE OF BRADYKININE ANTAGONISTS TO STIMULATE OR INDUCE HAIR GROWTH AND / OR STOP THE HAIR LOSS |
| DE19612067A1 (en) * | 1996-03-27 | 1997-10-02 | Hoechst Ag | Use of bradykinin antagonists for the manufacture of medicaments for the treatment of chronic fibrogenetic liver diseases and acute liver diseases |
| FR2756566B1 (en) * | 1996-12-04 | 1999-01-08 | Fournier Ind & Sante | BRADYKININ B2 RECEPTOR AGONIST PEPTIDES, METHOD OF PREPARATION AND USE IN THERAPEUTICS |
| ES2382383T3 (en) * | 2004-06-17 | 2012-06-07 | Infinity Discovery, Inc. | Compounds and procedures to inhibit the interaction of Bcl proteins with binding components |
| KR101707887B1 (en) * | 2016-11-22 | 2017-02-17 | 홍인석 | manufacturing apparatus of packaging paper that attach fragrance sheet and the manufacturing method |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4693993A (en) | 1985-06-13 | 1987-09-15 | Stewart John M | Bradykinin antagonist peptides |
| DE3618218A1 (en) | 1986-05-30 | 1987-12-03 | Hoechst Ag | AMINO ACID OOBT ESTER, METHOD FOR THE PRODUCTION AND USE THEREOF |
| DE3635670A1 (en) | 1986-10-21 | 1988-04-28 | Hoechst Ag | SYNTHESIS OF PEPTIDE-AMINOALKYLAMIDES AND PEPTIDYHYDRAZIDES BY MEANS OF THE SOLID PHASE METHOD |
| US4923963A (en) * | 1987-09-02 | 1990-05-08 | Nova Technology Limited Partnership | Bradykinin antagonist peptides |
| JPH02501224A (en) * | 1987-09-02 | 1990-04-26 | スチュワート、ジョン エム | Bradykinin antagonist peptide |
-
1989
- 1989-08-14 DE DE3926822A patent/DE3926822A1/en not_active Withdrawn
-
1990
- 1990-08-10 FI FI903971A patent/FI102759B1/en active IP Right Grant
- 1990-08-10 NZ NZ234861A patent/NZ234861A/en unknown
- 1990-08-11 ES ES90115455T patent/ES2065445T3/en not_active Expired - Lifetime
- 1990-08-11 EP EP90115455A patent/EP0413277B1/en not_active Expired - Lifetime
- 1990-08-11 DE DE59007747T patent/DE59007747D1/en not_active Expired - Lifetime
- 1990-08-11 AT AT90115455T patent/ATE114320T1/en not_active IP Right Cessation
- 1990-08-11 DK DK90115455.9T patent/DK0413277T3/en active
- 1990-08-13 ZA ZA906381A patent/ZA906381B/en unknown
- 1990-08-13 IL IL9535790A patent/IL95357A/en unknown
- 1990-08-13 CN CN90106915A patent/CN1034577C/en not_active Expired - Lifetime
- 1990-08-13 CZ CS903979A patent/CZ284783B6/en not_active IP Right Cessation
- 1990-08-13 CA CA002023194A patent/CA2023194C/en not_active Expired - Lifetime
- 1990-08-13 NO NO903545A patent/NO178433C/en not_active IP Right Cessation
- 1990-08-13 DD DD90343416A patent/DD297169A5/en not_active IP Right Cessation
- 1990-08-13 KR KR1019900012424A patent/KR0173976B1/en not_active Expired - Fee Related
- 1990-08-13 JP JP2211764A patent/JP2997519B2/en not_active Expired - Lifetime
- 1990-08-13 SK SK3979-90A patent/SK280787B6/en not_active IP Right Cessation
- 1990-08-13 AU AU60924/90A patent/AU638735B2/en not_active Expired
- 1990-08-13 HU HU904989A patent/HU208324B/en unknown
- 1990-08-13 IE IE292390A patent/IE65356B1/en not_active IP Right Cessation
- 1990-08-13 PT PT94982A patent/PT94982B/en not_active IP Right Cessation
-
1992
- 1992-01-28 RU SU925010606A patent/RU2081880C1/en active
-
1993
- 1993-11-12 LT LTIP1466A patent/LT3868B/en not_active IP Right Cessation
-
1998
- 1998-02-20 CY CY202998A patent/CY2029A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2023194A1 (en) | Peptides having bradykinin antagonist action | |
| AU3943189A (en) | Peptides having bradykinin antagonist action | |
| CA2041268A1 (en) | Peptides with a bradykinin-antagonistic action |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |