CA2185394A1 - Biotinderivate - Google Patents
BiotinderivateInfo
- Publication number
- CA2185394A1 CA2185394A1 CA002185394A CA2185394A CA2185394A1 CA 2185394 A1 CA2185394 A1 CA 2185394A1 CA 002185394 A CA002185394 A CA 002185394A CA 2185394 A CA2185394 A CA 2185394A CA 2185394 A1 CA2185394 A1 CA 2185394A1
- Authority
- CA
- Canada
- Prior art keywords
- gly
- asp
- arg
- absent
- biotin
- 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
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 208000035475 disorder Diseases 0.000 abstract 2
- 206010003210 Arteriosclerosis Diseases 0.000 abstract 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 208000007536 Thrombosis Diseases 0.000 abstract 1
- 230000002491 angiogenic effect Effects 0.000 abstract 1
- 208000011775 arteriosclerosis disease Diseases 0.000 abstract 1
- 229960002685 biotin Drugs 0.000 abstract 1
- 235000020958 biotin Nutrition 0.000 abstract 1
- 239000011616 biotin Substances 0.000 abstract 1
- 150000001615 biotins Chemical class 0.000 abstract 1
- 208000029078 coronary artery disease Diseases 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 102000006495 integrins Human genes 0.000 abstract 1
- 108010044426 integrins Proteins 0.000 abstract 1
- 208000010125 myocardial infarction Diseases 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 238000011282 treatment Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/78—Connective tissue peptides, e.g. collagen, elastin, laminin, fibronectin, vitronectin or cold insoluble globulin [CIG]
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
- B01D15/3804—Affinity chromatography
-
- 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
- C07K1/14—Extraction; Separation; Purification
- C07K1/16—Extraction; Separation; Purification by chromatography
- C07K1/22—Affinity chromatography or related techniques based upon selective absorption processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/705—Receptors; Cell surface antigens; Cell surface determinants
- C07K14/70546—Integrin superfamily
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/745—Blood coagulation or fibrinolysis factors
- C07K14/75—Fibrinogen
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Hematology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Toxicology (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Cell Biology (AREA)
- Analytical Chemistry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Microbiology (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
Abstract
Biotin compounds of the formula I (see formula I) is which Q is absent, -NH-(CH2)n-CO or -NH-(CH2)n-NH- and R1 is X-Arg-Gly-Asp-Y, A-Cys(R2)-B-U or cyclo-(Arg-Gly-Asp-Z), where Z is bonded in the side chain to Q or, if Q is absent, to biotin, and A, B, U, X, Y, Z and n have the meanings stated is Claim 1, and their salts can be used as integrin inhibitors, in particular for the prophylaxis and treatment of disorders of the circulation, for thrombosis, myocardial infarct, coronary heart diseases, arteriosclerosis, angiogenic disorders and is tumour therapy.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19534016.7 | 1995-09-14 | ||
| DE19534016A DE19534016A1 (en) | 1995-09-14 | 1995-09-14 | Biotin derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2185394A1 true CA2185394A1 (en) | 1997-03-15 |
| CA2185394C CA2185394C (en) | 2007-05-01 |
Family
ID=7772112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002185394A Expired - Fee Related CA2185394C (en) | 1995-09-14 | 1996-09-12 | Biotinderivate |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP0771818B1 (en) |
| JP (1) | JP4127325B2 (en) |
| KR (1) | KR970015597A (en) |
| CN (1) | CN1168738C (en) |
| AT (1) | ATE215558T1 (en) |
| AU (1) | AU719307B2 (en) |
| BR (1) | BR9603741A (en) |
| CA (1) | CA2185394C (en) |
| CZ (1) | CZ291506B6 (en) |
| DE (2) | DE19534016A1 (en) |
| DK (1) | DK0771818T3 (en) |
| ES (1) | ES2174007T3 (en) |
| HU (1) | HUP9602223A3 (en) |
| MX (1) | MX9604019A (en) |
| NO (1) | NO314694B1 (en) |
| PL (1) | PL316069A1 (en) |
| PT (1) | PT771818E (en) |
| RU (1) | RU2171807C2 (en) |
| SI (1) | SI0771818T1 (en) |
| SK (1) | SK283129B6 (en) |
| TW (1) | TW517063B (en) |
| UA (1) | UA41981C2 (en) |
| ZA (1) | ZA967765B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000038717A2 (en) | 1998-12-23 | 2000-07-06 | G.D. Searle & Co. | Use of a matrix metalloproteinase inhibitor and radiation as a combined treatment of neoplasia |
| US20010053766A1 (en) * | 2000-02-11 | 2001-12-20 | Janardan Kumar | Method of treating disorders of the eye |
| KR100778633B1 (en) * | 2007-04-13 | 2007-11-28 | 성균관대학교산학협력단 | Glp-1 derivative linked biotin and biotin-polyethylene glycol, method for the preparation thereof and pharmaceutical composition comprising the same |
| JP5647972B2 (en) * | 2008-04-08 | 2015-01-07 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Compositions containing cyclic peptides and methods of use |
| CN108956790A (en) * | 2017-05-18 | 2018-12-07 | 中国人民解放军第二军医大学第二附属医院 | Application of one group of amino acid tags object in acute kidney injury diagnostic kit |
| CN113827591B (en) * | 2021-11-09 | 2023-06-09 | 上海市肺科医院 | Application of biotin in preparation of medicines for treating sepsis |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5315076B2 (en) * | 1973-09-27 | 1978-05-22 | ||
| JP2945680B2 (en) * | 1988-09-09 | 1999-09-06 | 旭硝子株式会社 | Peptide derivatives and their uses |
| US5087561A (en) * | 1990-06-28 | 1992-02-11 | Merck & Co., Inc. | Humoral hypercalcemic factor antagonists modified at position 13 by biotin |
| DE4310643A1 (en) * | 1993-04-01 | 1994-10-06 | Merck Patent Gmbh | Cyclic adhesion inhibitors |
| US5462939A (en) * | 1993-05-07 | 1995-10-31 | Sterling Winthrop Inc. | Peptidic ketones as interleukin-1β-converting enzyme inhibitors |
| DE4336758A1 (en) * | 1993-10-28 | 1995-05-04 | Merck Patent Gmbh | Linear Adhesion Inhibitors |
-
1995
- 1995-09-14 DE DE19534016A patent/DE19534016A1/en not_active Withdrawn
-
1996
- 1996-07-17 TW TW085108686A patent/TW517063B/en not_active IP Right Cessation
- 1996-08-13 HU HU9602223A patent/HUP9602223A3/en unknown
- 1996-09-09 CZ CZ19962629A patent/CZ291506B6/en not_active IP Right Cessation
- 1996-09-09 AU AU65518/96A patent/AU719307B2/en not_active Ceased
- 1996-09-10 EP EP96114454A patent/EP0771818B1/en not_active Expired - Lifetime
- 1996-09-10 SI SI9630482T patent/SI0771818T1/en unknown
- 1996-09-10 DE DE59608995T patent/DE59608995D1/en not_active Expired - Lifetime
- 1996-09-10 DK DK96114454T patent/DK0771818T3/en active
- 1996-09-10 SK SK1156-96A patent/SK283129B6/en unknown
- 1996-09-10 ES ES96114454T patent/ES2174007T3/en not_active Expired - Lifetime
- 1996-09-10 AT AT96114454T patent/ATE215558T1/en active
- 1996-09-10 PT PT96114454T patent/PT771818E/en unknown
- 1996-09-11 MX MX9604019A patent/MX9604019A/en not_active IP Right Cessation
- 1996-09-12 CN CNB961125985A patent/CN1168738C/en not_active Expired - Fee Related
- 1996-09-12 BR BR9603741A patent/BR9603741A/en active Search and Examination
- 1996-09-12 CA CA002185394A patent/CA2185394C/en not_active Expired - Fee Related
- 1996-09-13 RU RU96118231/04A patent/RU2171807C2/en not_active IP Right Cessation
- 1996-09-13 JP JP26372696A patent/JP4127325B2/en not_active Expired - Fee Related
- 1996-09-13 PL PL96316069A patent/PL316069A1/en unknown
- 1996-09-13 NO NO19963851A patent/NO314694B1/en unknown
- 1996-09-13 ZA ZA967765A patent/ZA967765B/en unknown
- 1996-09-13 KR KR1019960039768A patent/KR970015597A/en not_active Application Discontinuation
- 1996-09-13 UA UA96093556A patent/UA41981C2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| UA41981C2 (en) | 2001-10-15 |
| EP0771818A3 (en) | 1997-07-02 |
| JPH09124692A (en) | 1997-05-13 |
| CA2185394C (en) | 2007-05-01 |
| AU6551896A (en) | 1997-03-20 |
| DE59608995D1 (en) | 2002-05-08 |
| EP0771818A2 (en) | 1997-05-07 |
| SK283129B6 (en) | 2003-02-04 |
| CN1168738C (en) | 2004-09-29 |
| SI0771818T1 (en) | 2002-10-31 |
| BR9603741A (en) | 1998-06-02 |
| CZ262996A3 (en) | 1998-02-18 |
| PT771818E (en) | 2002-09-30 |
| CZ291506B6 (en) | 2003-03-12 |
| RU2171807C2 (en) | 2001-08-10 |
| HU9602223D0 (en) | 1996-10-28 |
| HUP9602223A3 (en) | 1998-03-02 |
| HUP9602223A2 (en) | 1997-06-30 |
| NO963851L (en) | 1997-03-17 |
| KR970015597A (en) | 1997-04-28 |
| SK115696A3 (en) | 1997-05-07 |
| ATE215558T1 (en) | 2002-04-15 |
| DE19534016A1 (en) | 1997-03-20 |
| JP4127325B2 (en) | 2008-07-30 |
| ZA967765B (en) | 1997-03-26 |
| AU719307B2 (en) | 2000-05-04 |
| NO963851D0 (en) | 1996-09-13 |
| DK0771818T3 (en) | 2002-07-29 |
| TW517063B (en) | 2003-01-11 |
| EP0771818B1 (en) | 2002-04-03 |
| CN1153784A (en) | 1997-07-09 |
| NO314694B1 (en) | 2003-05-05 |
| PL316069A1 (en) | 1997-03-17 |
| MX9604019A (en) | 1997-03-29 |
| ES2174007T3 (en) | 2002-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150914 |