ZA200305550B - Urea and urethane derivatives as integrin inhibitors. - Google Patents
Urea and urethane derivatives as integrin inhibitors. Download PDFInfo
- Publication number
- ZA200305550B ZA200305550B ZA200305550A ZA200305550A ZA200305550B ZA 200305550 B ZA200305550 B ZA 200305550B ZA 200305550 A ZA200305550 A ZA 200305550A ZA 200305550 A ZA200305550 A ZA 200305550A ZA 200305550 B ZA200305550 B ZA 200305550B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- ylamino
- pyridin
- compounds
- propionic acid
- Prior art date
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- 102000006495 integrins Human genes 0.000 title claims description 21
- 108010044426 integrins Proteins 0.000 title claims description 21
- 239000003112 inhibitor Substances 0.000 title claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 3
- 239000004202 carbamide Substances 0.000 title description 3
- 150000003673 urethanes Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 87
- -1 biphenylyl Chemical group 0.000 claims description 68
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 48
- 235000019260 propionic acid Nutrition 0.000 claims description 24
- 125000006239 protecting group Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000012453 solvate Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 239000007790 solid phase Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 238000005859 coupling reaction Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 2
- 150000001499 aryl bromides Chemical class 0.000 claims description 2
- 150000007514 bases Chemical class 0.000 claims description 2
- 125000005620 boronic acid group Chemical class 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
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- 201000003068 rheumatic fever Diseases 0.000 claims description 2
- TVTVJTVBDTYBIZ-UHFFFAOYSA-N 3-[4-(4-methylphenyl)phenyl]-3-[[2-[2-(pyridin-2-ylamino)ethoxycarbonylamino]acetyl]amino]propanoic acid Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(CC(O)=O)NC(=O)CNC(=O)OCCNC=2N=CC=CC=2)C=C1 TVTVJTVBDTYBIZ-UHFFFAOYSA-N 0.000 claims 1
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- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 description 15
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 210000004881 tumor cell Anatomy 0.000 description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
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- 125000002252 acyl group Chemical group 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
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- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 4
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 4
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 3
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 125000003435 aroyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Oncology (AREA)
- Physical Education & Sports Medicine (AREA)
- Communicable Diseases (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Dermatology (AREA)
- Vascular Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Surgery (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Virology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10063173A DE10063173A1 (de) | 2000-12-18 | 2000-12-18 | Harnstoff- und Urethanderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200305550B true ZA200305550B (en) | 2004-10-18 |
Family
ID=7667710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200305550A ZA200305550B (en) | 2000-12-18 | 2003-07-17 | Urea and urethane derivatives as integrin inhibitors. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7135587B2 (da) |
| EP (1) | EP1343764B1 (da) |
| JP (1) | JP4216071B2 (da) |
| KR (1) | KR20030063432A (da) |
| CN (1) | CN1481364A (da) |
| AR (1) | AR035608A1 (da) |
| AT (1) | ATE274497T1 (da) |
| AU (1) | AU2002217078A1 (da) |
| BR (1) | BR0116202A (da) |
| CA (1) | CA2431974C (da) |
| CZ (1) | CZ20031775A3 (da) |
| DE (2) | DE10063173A1 (da) |
| DK (1) | DK1343764T3 (da) |
| ES (1) | ES2227063T3 (da) |
| HU (1) | HUP0302753A3 (da) |
| MX (1) | MXPA03005431A (da) |
| NO (1) | NO20032754L (da) |
| PL (1) | PL361745A1 (da) |
| PT (1) | PT1343764E (da) |
| RU (1) | RU2003121015A (da) |
| SK (1) | SK8182003A3 (da) |
| WO (1) | WO2002050039A1 (da) |
| ZA (1) | ZA200305550B (da) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10204789A1 (de) * | 2002-02-06 | 2003-08-14 | Merck Patent Gmbh | Inhibitoren des Integrins alpha¶v¶beta6 |
| EA011853B1 (ru) | 2002-03-13 | 2009-06-30 | Байоджен Айдек Ма Инк. | АНТИТЕЛА ПРОТИВ αβ |
| DK1667668T3 (da) * | 2003-10-01 | 2008-09-15 | Merck Patent Gmbh | Alfabeta3 og altabeta6-integrinantagonister som antifibrotiske midler |
| CN102875681A (zh) | 2005-07-08 | 2013-01-16 | 拜奥根Idec马萨诸塞公司 | 抗-αvβ6抗体及其用途 |
| WO2008008315A2 (en) | 2006-07-10 | 2008-01-17 | Biogen Idec Ma Inc. | Compositions and methods for inhibiting growth of smad4-deficient cancers |
| JP2010506944A (ja) * | 2006-10-19 | 2010-03-04 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | インテグリンαＶβ６のアンタゴニストを用いる慢性喘息の処置および予防 |
| AT509266B1 (de) * | 2009-12-28 | 2014-07-15 | Tech Universität Wien | Substituierte pyridine und pyrimidine |
| CN102353728B (zh) * | 2011-06-29 | 2013-03-27 | 中国食品发酵工业研究院 | 一种黄酒生产过程质量控制快速检测方法 |
| US10035860B2 (en) | 2013-03-15 | 2018-07-31 | Biogen Ma Inc. | Anti-alpha V beta 6 antibodies and uses thereof |
| WO2014144466A1 (en) | 2013-03-15 | 2014-09-18 | Biogen Idec Ma Inc. | Anti-alpha v beta 6 antibodies and uses thereof |
| PE20181496A1 (es) * | 2015-10-23 | 2018-09-18 | Vifor Int Ag | Inhibidores de ferroportina novedosos |
| JOP20180036A1 (ar) | 2017-04-18 | 2019-01-30 | Vifor Int Ag | أملاح لمثبطات فروبورتين جديدة |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6306840B1 (en) | 1995-01-23 | 2001-10-23 | Biogen, Inc. | Cell adhesion inhibitors |
| JP4753403B2 (ja) * | 1998-04-16 | 2011-08-24 | エンサイシブ・フアーマシユーテイカルズ，インコーポレイテツド | インテグリンのそのレセプターへの結合を阻害する化合物 |
| GB9909409D0 (en) * | 1999-04-24 | 1999-06-23 | Zeneca Ltd | Chemical compounds |
| DE19939980A1 (de) * | 1999-08-24 | 2001-03-01 | Merck Patent Gmbh | Inhibitoren des Integrins alphavbeta¶3¶ |
-
2000
- 2000-12-18 DE DE10063173A patent/DE10063173A1/de not_active Withdrawn
-
2001
- 2001-11-30 SK SK818-2003A patent/SK8182003A3/sk unknown
- 2001-11-30 BR BR0116202-0A patent/BR0116202A/pt not_active Application Discontinuation
- 2001-11-30 WO PCT/EP2001/014039 patent/WO2002050039A1/en not_active Application Discontinuation
- 2001-11-30 MX MXPA03005431A patent/MXPA03005431A/es unknown
- 2001-11-30 EP EP01271360A patent/EP1343764B1/en not_active Expired - Lifetime
- 2001-11-30 DE DE60105192T patent/DE60105192T2/de not_active Expired - Lifetime
- 2001-11-30 HU HU0302753A patent/HUP0302753A3/hu unknown
- 2001-11-30 AU AU2002217078A patent/AU2002217078A1/en not_active Abandoned
- 2001-11-30 DK DK01271360T patent/DK1343764T3/da active
- 2001-11-30 ES ES01271360T patent/ES2227063T3/es not_active Expired - Lifetime
- 2001-11-30 CZ CZ20031775A patent/CZ20031775A3/cs unknown
- 2001-11-30 CN CNA01820791XA patent/CN1481364A/zh active Pending
- 2001-11-30 PT PT01271360T patent/PT1343764E/pt unknown
- 2001-11-30 PL PL01361745A patent/PL361745A1/xx unknown
- 2001-11-30 AT AT01271360T patent/ATE274497T1/de not_active IP Right Cessation
- 2001-11-30 US US10/450,855 patent/US7135587B2/en not_active Expired - Fee Related
- 2001-11-30 KR KR10-2003-7008122A patent/KR20030063432A/ko not_active Application Discontinuation
- 2001-11-30 RU RU2003121015/04A patent/RU2003121015A/ru not_active Application Discontinuation
- 2001-11-30 CA CA2431974A patent/CA2431974C/en not_active Expired - Fee Related
- 2001-11-30 JP JP2002551536A patent/JP4216071B2/ja not_active Expired - Fee Related
- 2001-12-14 AR ARP010105796A patent/AR035608A1/es unknown
-
2003
- 2003-06-17 NO NO20032754A patent/NO20032754L/no unknown
- 2003-07-17 ZA ZA200305550A patent/ZA200305550B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0302753A3 (en) | 2005-03-29 |
| MXPA03005431A (es) | 2003-09-10 |
| DE60105192D1 (de) | 2004-09-30 |
| CA2431974C (en) | 2010-08-17 |
| NO20032754D0 (no) | 2003-06-17 |
| HUP0302753A2 (hu) | 2003-12-29 |
| JP4216071B2 (ja) | 2009-01-28 |
| JP2004516282A (ja) | 2004-06-03 |
| PL361745A1 (en) | 2004-10-04 |
| ATE274497T1 (de) | 2004-09-15 |
| CN1481364A (zh) | 2004-03-10 |
| DE10063173A1 (de) | 2002-06-20 |
| AR035608A1 (es) | 2004-06-16 |
| DK1343764T3 (da) | 2004-12-06 |
| CA2431974A1 (en) | 2002-06-27 |
| DE60105192T2 (de) | 2005-09-08 |
| EP1343764B1 (en) | 2004-08-25 |
| WO2002050039A1 (en) | 2002-06-27 |
| BR0116202A (pt) | 2003-12-23 |
| AU2002217078A1 (en) | 2002-07-01 |
| SK8182003A3 (en) | 2003-10-07 |
| KR20030063432A (ko) | 2003-07-28 |
| EP1343764A1 (en) | 2003-09-17 |
| PT1343764E (pt) | 2005-01-31 |
| CZ20031775A3 (cs) | 2003-09-17 |
| RU2003121015A (ru) | 2005-02-10 |
| US7135587B2 (en) | 2006-11-14 |
| ES2227063T3 (es) | 2005-04-01 |
| NO20032754L (no) | 2003-06-17 |
| US20040063644A1 (en) | 2004-04-01 |
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