JP2003514920A - 抗血管新生活性を有するｎ−アルキル化ペプチド - Google Patents
抗血管新生活性を有するｎ−アルキル化ペプチドInfo
- Publication number
- JP2003514920A JP2003514920A JP2001540160A JP2001540160A JP2003514920A JP 2003514920 A JP2003514920 A JP 2003514920A JP 2001540160 A JP2001540160 A JP 2001540160A JP 2001540160 A JP2001540160 A JP 2001540160A JP 2003514920 A JP2003514920 A JP 2003514920A
- Authority
- JP
- Japan
- Prior art keywords
- ile
- alanyl
- sar
- gly
- arg
- 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.)
- Withdrawn
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title abstract description 346
- 102000004196 processed proteins & peptides Human genes 0.000 title description 21
- 230000001772 anti-angiogenic effect Effects 0.000 title description 7
- 238000000034 method Methods 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 23
- -1 N-methylprolyl Chemical group 0.000 claims description 483
- 150000001875 compounds Chemical class 0.000 claims description 104
- 150000001413 amino acids Chemical class 0.000 claims description 79
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 32
- 125000001288 lysyl group Chemical group 0.000 claims description 31
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 31
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 claims description 27
- 125000003901 ceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 claims description 24
- 125000000613 asparagine group Chemical group N[C@@H](CC(N)=O)C(=O)* 0.000 claims description 21
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 claims description 20
- 125000000405 phenylalanyl group Chemical group 0.000 claims description 20
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- 206010028980 Neoplasm Diseases 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
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- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 102000005962 receptors Human genes 0.000 claims description 16
- 108020003175 receptors Proteins 0.000 claims description 16
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- AHLPHDHHMVZTML-BYPYZUCNSA-N ornithyl group Chemical group N[C@@H](CCCN)C(=O)O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 15
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 claims description 15
- 125000000249 D-isoleucyl group Chemical group N[C@@H](C(=O)*)[C@@H](CC)C 0.000 claims description 14
- 125000003301 D-leucyl group Chemical group N[C@@H](C(=O)*)CC(C)C 0.000 claims description 14
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 14
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 13
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 12
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
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- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 11
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000000030 D-alanine group Chemical group [H]N([H])[C@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims description 11
- 125000000197 D-threonyl group Chemical group N[C@@H](C(=O)*)[C@H](C)O 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000003182 D-alloisoleucine group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])[C@](C([H])([H])[H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 10
- 125000000180 D-prolyl group Chemical group N1[C@@H](C(=O)*)CCC1 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229950003188 isovaleryl diethylamide Drugs 0.000 claims description 10
- 125000003625 D-valyl group Chemical group N[C@@H](C(=O)*)C(C)C 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 8
- 125000000028 D-cysteine group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C(S[H])([H])[H] 0.000 claims description 8
- 125000003442 D-glutaminyl group Chemical group N[C@@H](C(=O)*)CCC(=O)N 0.000 claims description 8
- 125000000240 D-tyrosyl group Chemical group N[C@@H](C(=O)*)CC1=CC=C(C=C1)O 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
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- 206010029113 Neovascularisation Diseases 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 6
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 238000001356 surgical procedure Methods 0.000 claims description 6
- 125000001203 alloisoleucine group Chemical group 0.000 claims description 5
- 125000000539 amino acid group Chemical group 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
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- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims description 5
- OGQDIIKRQRZXJH-UHFFFAOYSA-N protriptyline hydrochloride Chemical group [Cl-].C1=CC2=CC=CC=C2C(CCC[NH2+]C)C2=CC=CC=C21 OGQDIIKRQRZXJH-UHFFFAOYSA-N 0.000 claims description 5
- QKNFFJHHPCWXTH-GSVOUGTGSA-N (2r)-2-(methylamino)propanamide Chemical compound CN[C@H](C)C(N)=O QKNFFJHHPCWXTH-GSVOUGTGSA-N 0.000 claims description 4
- RKGFWMYLTBPZGL-YUMQZZPRSA-N (2s)-2-amino-1-[(2s)-2-amino-4-methylsulfanylbutanoyl]sulfinyl-4-methylsulfanylbutan-1-one Chemical compound CSCC[C@H](N)C(=O)S(=O)C(=O)[C@@H](N)CCSC RKGFWMYLTBPZGL-YUMQZZPRSA-N 0.000 claims description 4
- RZTMKPNHKUTQSB-YUMQZZPRSA-N (2s)-2-amino-1-[(2s)-2-amino-4-methylsulfanylbutanoyl]sulfonyl-4-methylsulfanylbutan-1-one Chemical compound CSCC[C@H](N)C(=O)S(=O)(=O)C(=O)[C@@H](N)CCSC RZTMKPNHKUTQSB-YUMQZZPRSA-N 0.000 claims description 4
- WAMWSIDTKSNDCU-ZETCQYMHSA-N (2s)-2-azaniumyl-2-cyclohexylacetate Chemical group OC(=O)[C@@H](N)C1CCCCC1 WAMWSIDTKSNDCU-ZETCQYMHSA-N 0.000 claims description 4
- JIZNFRPSBHXXMD-SCSAIBSYSA-N (4R)-1,4-diaminopentan-3-one Chemical compound C[C@@H](N)C(=O)CCN JIZNFRPSBHXXMD-SCSAIBSYSA-N 0.000 claims description 4
- JIZNFRPSBHXXMD-BYPYZUCNSA-N (4s)-1,4-diaminopentan-3-one Chemical compound C[C@H](N)C(=O)CCN JIZNFRPSBHXXMD-BYPYZUCNSA-N 0.000 claims description 4
- ODANWMOQWMHGCY-UHFFFAOYSA-N 1,4-diaminobutan-2-one Chemical compound NCCC(=O)CN ODANWMOQWMHGCY-UHFFFAOYSA-N 0.000 claims description 4
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- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 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
- C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
-
- 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
-
- 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]
-
- 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)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Ophthalmology & Optometry (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44709999A | 1999-11-22 | 1999-11-22 | |
| US09/447,099 | 1999-11-22 | ||
| US70264900A | 2000-10-31 | 2000-10-31 | |
| US09/702,649 | 2000-10-31 | ||
| PCT/US2000/032105 WO2001038397A1 (en) | 1999-11-22 | 2000-11-22 | N-alkylated peptides having antiangiogenic activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2003514920A true JP2003514920A (ja) | 2003-04-22 |
Family
ID=27034850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001540160A Withdrawn JP2003514920A (ja) | 1999-11-22 | 2000-11-22 | 抗血管新生活性を有するｎ−アルキル化ペプチド |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1242455A1 (es) |
| JP (1) | JP2003514920A (es) |
| AR (1) | AR026901A1 (es) |
| AU (1) | AU1791301A (es) |
| BR (1) | BR0010934A (es) |
| CA (1) | CA2386893A1 (es) |
| CO (1) | CO5261544A1 (es) |
| HK (1) | HK1050902A1 (es) |
| MX (1) | MXPA02005139A (es) |
| WO (1) | WO2001038397A1 (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020183242A1 (en) * | 2001-04-11 | 2002-12-05 | Jack Henkin | Peptide antiangiogenic drugs |
| US7122625B2 (en) | 2001-10-31 | 2006-10-17 | Abbott Laboratories | Hexa-, hepta-, and octapeptides having antiangiogenic activity |
| US7037897B2 (en) | 2001-10-31 | 2006-05-02 | Abbott Laboratories | TRI-, TETRA-, and penta-peptides having antiangiogenic activity |
| US7001984B2 (en) | 2001-10-31 | 2006-02-21 | Abbott Laboratories | Di-, tri-, and tetra-peptides having antiangiogenic activity |
| US7067490B2 (en) | 2001-10-31 | 2006-06-27 | Abbott Laboratories | Hepta-, Octa-and nonapeptides having antiangiogenic activity |
| US7169888B2 (en) | 2001-10-31 | 2007-01-30 | Abbott Laboratories | Tetra-, penta-, hexa- and heptapeptides having antiangiogenic activity |
| US20030125259A1 (en) | 2001-10-31 | 2003-07-03 | Fortuna Haviv | Octa- and nonapeptides having antiangiogenic activity |
| US20030119746A1 (en) * | 2001-10-31 | 2003-06-26 | Fortuna Haviv | Hepta-and octapeptides having antiangiogenic activity |
| US20030228365A1 (en) * | 2002-06-07 | 2003-12-11 | Fortuna Haviv | Pharmaceutical formulation |
| CA2598833A1 (en) | 2005-03-03 | 2006-09-08 | Curt W. Bradshaw | Anti-angiogenic compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU720632B2 (en) * | 1996-03-05 | 2000-06-08 | Trega Biosciences, Inc. | Selectively N-alkylated peptidomimetic combinatorial libraries and compounds therein |
| JP4426650B2 (ja) * | 1996-05-03 | 2010-03-03 | アボット・ラボラトリーズ | 新規な抗血管形成ペプチド、それをコードするポリヌクレオチド、および血管形成を阻害する方法 |
| PT918795E (pt) * | 1997-03-17 | 2005-02-28 | Abbott Lab | Droga antiangiogenica para tratar cancro artrite e retinopatia |
-
2000
- 2000-11-20 CO CO00088047A patent/CO5261544A1/es not_active Application Discontinuation
- 2000-11-22 JP JP2001540160A patent/JP2003514920A/ja not_active Withdrawn
- 2000-11-22 WO PCT/US2000/032105 patent/WO2001038397A1/en active Application Filing
- 2000-11-22 AR ARP000106173A patent/AR026901A1/es unknown
- 2000-11-22 MX MXPA02005139A patent/MXPA02005139A/es not_active Application Discontinuation
- 2000-11-22 AU AU17913/01A patent/AU1791301A/en not_active Abandoned
- 2000-11-22 CA CA002386893A patent/CA2386893A1/en not_active Abandoned
- 2000-11-22 EP EP00980685A patent/EP1242455A1/en active Pending
- 2000-11-22 BR BR0010934-7A patent/BR0010934A/pt not_active IP Right Cessation
-
2003
- 2003-02-17 HK HK03101124.4A patent/HK1050902A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU1791301A (en) | 2001-06-04 |
| MXPA02005139A (es) | 2004-08-23 |
| AR026901A1 (es) | 2003-03-05 |
| HK1050902A1 (zh) | 2003-07-11 |
| CA2386893A1 (en) | 2001-05-31 |
| CO5261544A1 (es) | 2003-03-31 |
| BR0010934A (pt) | 2002-12-17 |
| EP1242455A1 (en) | 2002-09-25 |
| WO2001038397A1 (en) | 2001-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A300 | Application deemed to be withdrawn because no request for examination was validly filed |
Free format text: JAPANESE INTERMEDIATE CODE: A300 Effective date: 20080205 |