ZA200302256B - Biphenyl derivatives and the use thereof as integrin inhibitors. - Google Patents
Biphenyl derivatives and the use thereof as integrin inhibitors. Download PDFInfo
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- ZA200302256B ZA200302256B ZA200302256A ZA200302256A ZA200302256B ZA 200302256 B ZA200302256 B ZA 200302256B ZA 200302256 A ZA200302256 A ZA 200302256A ZA 200302256 A ZA200302256 A ZA 200302256A ZA 200302256 B ZA200302256 B ZA 200302256B
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- South Africa
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- 108010044426 integrins Proteins 0.000 title claims description 26
- 102000006495 integrins Human genes 0.000 title claims description 26
- 239000003112 inhibitor Substances 0.000 title claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 111
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000006239 protecting group Chemical group 0.000 claims description 26
- 239000007790 solid phase Substances 0.000 claims description 22
- 239000012453 solvate Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 235000019260 propionic acid Nutrition 0.000 claims description 15
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 11
- 230000008878 coupling Effects 0.000 claims description 10
- 238000010168 coupling process Methods 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
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- 125000000524 functional group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
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- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
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- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
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- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 2
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- 208000029078 coronary artery disease Diseases 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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- -1 1l-ethylpropyl Chemical group 0.000 description 59
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 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 description 7
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- 239000005557 antagonist Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- RZQATTRHGWEOLS-UHFFFAOYSA-N 4-(1h-benzimidazol-2-ylamino)butanoic acid Chemical compound C1=CC=C2NC(NCCCC(=O)O)=NC2=C1 RZQATTRHGWEOLS-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 4
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Classifications
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- 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
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- 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
- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Vascular Medicine (AREA)
- Surgery (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10041423A DE10041423A1 (de) | 2000-08-23 | 2000-08-23 | Biphenylderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200302256B true ZA200302256B (en) | 2004-07-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200302256A ZA200302256B (en) | 2000-08-23 | 2003-03-20 | Biphenyl derivatives and the use thereof as integrin inhibitors. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20040010023A1 (no) |
| EP (1) | EP1311489A1 (no) |
| JP (1) | JP2004524264A (no) |
| KR (1) | KR20030022418A (no) |
| CN (1) | CN1447799A (no) |
| AU (1) | AU2001277561A1 (no) |
| BR (1) | BR0113374A (no) |
| CA (1) | CA2420208A1 (no) |
| CZ (1) | CZ2003671A3 (no) |
| DE (1) | DE10041423A1 (no) |
| HU (1) | HUP0301784A3 (no) |
| MX (1) | MXPA03001557A (no) |
| NO (1) | NO20030813D0 (no) |
| PL (1) | PL359668A1 (no) |
| SK (1) | SK2962003A3 (no) |
| WO (1) | WO2002016328A1 (no) |
| ZA (1) | ZA200302256B (no) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10112771A1 (de) | 2001-03-16 | 2002-09-26 | Merck Patent Gmbh | Inhibitoren des Integrins alpha¶v¶beta¶6¶ |
| DE10127041A1 (de) * | 2001-06-02 | 2002-12-05 | Merck Patent Gmbh | Integrinantagonisten |
| CN1964740A (zh) | 2004-04-02 | 2007-05-16 | 加利福尼亚大学董事会 | 治疗和预防与αVβ5整联蛋白有关的疾病的方法和组合物 |
| BR112012001463A2 (pt) | 2009-07-24 | 2016-03-15 | Univ California | métodos e composições para tratar e prevenir doença associada à integrina alfavbeta5 |
| RU2769702C2 (ru) | 2017-02-28 | 2022-04-05 | Морфик Терапьютик, Инк. | Ингибиторы интегрина avb6 |
| MA47692A (fr) | 2017-02-28 | 2020-01-08 | Morphic Therapeutic Inc | Inhibiteurs de l'intégrine (alpha-v) (bêta-6) |
| WO2019200202A1 (en) | 2018-04-12 | 2019-10-17 | Morphic Therapeutic, Inc. | Antagonists of human integrin (alpha4)(beta7) |
| MX2021002181A (es) | 2018-08-29 | 2021-07-15 | Morphic Therapeutic Inc | Inhibicion de la integrina alfa v beta 6. |
| CA3154269A1 (en) | 2019-10-16 | 2021-04-22 | Matthew G. Bursavich | Inhibiting human integrin .alpha.4.beta.7 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0880511A4 (en) * | 1996-01-16 | 1999-06-16 | Merck & Co Inc | INTEGRIN RECEPTOR ANTAGONISTS |
| AU751950B2 (en) * | 1997-11-24 | 2002-09-05 | Merck & Co., Inc. | Substituted beta-alanine derivatives as cell adhesion inhibitors |
| CN1146541C (zh) * | 1999-02-20 | 2004-04-21 | 默克专利股份有限公司 | β-丙氨酸衍生物 |
-
2000
- 2000-08-23 DE DE10041423A patent/DE10041423A1/de not_active Withdrawn
-
2001
- 2001-08-02 BR BR0113374-8A patent/BR0113374A/pt not_active Application Discontinuation
- 2001-08-02 CA CA002420208A patent/CA2420208A1/en not_active Abandoned
- 2001-08-02 CN CN01814416A patent/CN1447799A/zh active Pending
- 2001-08-02 US US10/362,234 patent/US20040010023A1/en not_active Abandoned
- 2001-08-02 AU AU2001277561A patent/AU2001277561A1/en not_active Abandoned
- 2001-08-02 WO PCT/EP2001/008970 patent/WO2002016328A1/de not_active Application Discontinuation
- 2001-08-02 PL PL01359668A patent/PL359668A1/xx unknown
- 2001-08-02 JP JP2002521429A patent/JP2004524264A/ja active Pending
- 2001-08-02 HU HU0301784A patent/HUP0301784A3/hu unknown
- 2001-08-02 EP EP01955384A patent/EP1311489A1/de not_active Withdrawn
- 2001-08-02 MX MXPA03001557A patent/MXPA03001557A/es unknown
- 2001-08-02 KR KR10-2003-7002577A patent/KR20030022418A/ko not_active Application Discontinuation
- 2001-08-02 CZ CZ2003671A patent/CZ2003671A3/cs unknown
- 2001-08-02 SK SK296-2003A patent/SK2962003A3/sk unknown
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2003
- 2003-02-21 NO NO20030813A patent/NO20030813D0/no unknown
- 2003-03-20 ZA ZA200302256A patent/ZA200302256B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1447799A (zh) | 2003-10-08 |
| DE10041423A1 (de) | 2002-03-07 |
| US20040010023A1 (en) | 2004-01-15 |
| MXPA03001557A (es) | 2003-06-06 |
| NO20030813L (no) | 2003-02-21 |
| CA2420208A1 (en) | 2003-02-21 |
| EP1311489A1 (de) | 2003-05-21 |
| PL359668A1 (en) | 2004-08-23 |
| HUP0301784A2 (hu) | 2003-12-29 |
| AU2001277561A1 (en) | 2002-03-04 |
| NO20030813D0 (no) | 2003-02-21 |
| SK2962003A3 (en) | 2003-06-03 |
| CZ2003671A3 (cs) | 2003-06-18 |
| KR20030022418A (ko) | 2003-03-15 |
| JP2004524264A (ja) | 2004-08-12 |
| WO2002016328A1 (de) | 2002-02-28 |
| BR0113374A (pt) | 2003-07-08 |
| HUP0301784A3 (en) | 2004-03-29 |
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