CA2480756A1 - Heteroaryl compounds which inhibit leukocyte adhesion mediated by alpha-4 integrins - Google Patents
Heteroaryl compounds which inhibit leukocyte adhesion mediated by alpha-4 integrins Download PDFInfo
- Publication number
- CA2480756A1 CA2480756A1 CA002480756A CA2480756A CA2480756A1 CA 2480756 A1 CA2480756 A1 CA 2480756A1 CA 002480756 A CA002480756 A CA 002480756A CA 2480756 A CA2480756 A CA 2480756A CA 2480756 A1 CA2480756 A1 CA 2480756A1
- Authority
- CA
- Canada
- Prior art keywords
- diethylamino
- ylamino
- propionic acid
- dimethylcarbamoyloxyphenyl
- pyrimidin
- 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.)
- Abandoned
Links
- 108010044426 integrins Proteins 0.000 title claims abstract description 37
- 102000006495 integrins Human genes 0.000 title claims abstract description 37
- 230000001404 mediated effect Effects 0.000 title claims abstract description 22
- 230000023404 leukocyte cell-cell adhesion Effects 0.000 title abstract description 10
- 101001002508 Homo sapiens Immunoglobulin-binding protein 1 Proteins 0.000 title 1
- 102100021042 Immunoglobulin-binding protein 1 Human genes 0.000 title 1
- 125000001072 heteroaryl group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 10
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 72
- -1 4-chlorobenzenesulfonyl Chemical group 0.000 claims description 51
- 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 49
- 238000000034 method Methods 0.000 claims description 41
- 235000019260 propionic acid Nutrition 0.000 claims description 36
- 201000010099 disease Diseases 0.000 claims description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 239000003937 drug carrier Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
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- XGZSKLPECGWKPZ-UHFFFAOYSA-N 2-[[2-(diethylamino)-5-[(3,4-difluorophenyl)sulfonyl-propan-2-ylamino]pyrimidin-4-yl]amino]-3-[4-(dimethylcarbamoyloxy)phenyl]propanoic acid Chemical compound C=1C=C(OC(=O)N(C)C)C=CC=1CC(C(O)=O)NC1=NC(N(CC)CC)=NC=C1N(C(C)C)S(=O)(=O)C1=CC=C(F)C(F)=C1 XGZSKLPECGWKPZ-UHFFFAOYSA-N 0.000 claims description 2
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- MAZNQIVGHXAJRX-UHFFFAOYSA-N 2-[[5-[2-(3,5-dichlorophenyl)sulfonylethylamino]-2-(diethylamino)pyrimidin-4-yl]amino]-3-[4-(dimethylcarbamoyloxy)phenyl]propanoic acid Chemical compound C=1C=C(OC(=O)N(C)C)C=CC=1CC(C(O)=O)NC1=NC(N(CC)CC)=NC=C1NCCS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 MAZNQIVGHXAJRX-UHFFFAOYSA-N 0.000 claims description 2
- IKXAHYJACJXEFL-UHFFFAOYSA-N 2-[[5-[butyl-(4-fluorophenyl)sulfonylamino]-2-(diethylamino)pyrimidin-4-yl]amino]-3-[4-(dimethylcarbamoyloxy)phenyl]propanoic acid Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)N(CCCC)C1=CN=C(N(CC)CC)N=C1NC(C(O)=O)CC1=CC=C(OC(=O)N(C)C)C=C1 IKXAHYJACJXEFL-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
-
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
Landscapes
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38324402P | 2002-05-24 | 2002-05-24 | |
| US60/383,244 | 2002-05-24 | ||
| PCT/US2003/017150 WO2003099231A2 (en) | 2002-05-24 | 2003-05-27 | Heteroaryl compounds which inhibit leukocyte adhesion mediated by alpha-4 integrins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2480756A1 true CA2480756A1 (en) | 2003-12-04 |
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Family Applications (1)
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| CA002480756A Abandoned CA2480756A1 (en) | 2002-05-24 | 2003-05-27 | Heteroaryl compounds which inhibit leukocyte adhesion mediated by alpha-4 integrins |
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| AT (1) | ATE464298T1 (enExample) |
| AU (1) | AU2003237302B8 (enExample) |
| BR (1) | BR0309619A (enExample) |
| CA (1) | CA2480756A1 (enExample) |
| DE (1) | DE60332109D1 (enExample) |
| EA (1) | EA008180B1 (enExample) |
| IL (1) | IL164323A (enExample) |
| MX (1) | MXPA04011657A (enExample) |
| NO (1) | NO20045276L (enExample) |
| NZ (1) | NZ535723A (enExample) |
| TW (1) | TW200307671A (enExample) |
| WO (1) | WO2003099231A2 (enExample) |
| ZA (1) | ZA200407944B (enExample) |
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| ATE455106T1 (de) * | 1999-01-22 | 2010-01-15 | Elan Pharm Inc | Acyl derivate zur behandlung von krankheiten die in zusammenhang mit vla-4 stehen |
| TW200509930A (en) * | 2003-06-25 | 2005-03-16 | Elan Pharm Inc | Methods and compositions for treating rheumatoid arthritis |
| EP1725542A1 (en) * | 2004-03-10 | 2006-11-29 | Merck & Co., Inc. | Vla-4 antagonists |
| MX2007000228A (es) * | 2004-07-08 | 2007-03-30 | Elan Pharm Inc | Antagonistas de vla-4 multivalentes que comprenden porsiones de polietilenglicol. |
| WO2006023396A2 (en) * | 2004-08-16 | 2006-03-02 | Merck & Co., Inc. | Vla-4 antagonists |
| AU2006297180A1 (en) | 2005-09-29 | 2007-04-12 | Elan Pharmaceuticals, Inc. | Carbamate compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| WO2007041270A1 (en) * | 2005-09-29 | 2007-04-12 | Elan Pharmaceuticals, Inc. | Pyrimidinyl amide compounds which inhibit leukocyte adhesion mediated by vla-4 |
| EP1996559A1 (en) | 2006-02-27 | 2008-12-03 | Elan Pharmaceuticals Inc. | Pyrimidinyl sulfonamide compounds which inhibit leukocyte adhesion mediated by vla-4 |
| HUE047230T2 (hu) * | 2006-02-28 | 2020-04-28 | Biogen Ma Inc | Gyulladásos és autoimmun betegségek natalizumabbal való kezelésének módszerei |
| WO2007100763A2 (en) * | 2006-02-28 | 2007-09-07 | Elan Pharmaceuticals, Inc. | Methods of treating inflammatory and autoimmune diseases with alpha-4 inhibitory compounds |
| EP4582099A3 (en) * | 2006-03-03 | 2025-10-01 | Biogen MA Inc. | Methods of treating inflammatory and autoimmune diseases with natalizumab |
| CA2708262A1 (en) | 2007-12-07 | 2009-06-18 | Elan Pharmaceuticals, Inc. | Methods and compositions for treating liquid tumors |
| CA2760151A1 (en) * | 2009-04-27 | 2010-11-04 | Elan Pharmaceuticals, Inc. | Pyridinone antagonists of alpha-4 integrins |
| EP4152004B9 (en) | 2010-01-11 | 2025-04-09 | Biogen MA Inc. | Assay for jc virus antibodies |
| US11287423B2 (en) | 2010-01-11 | 2022-03-29 | Biogen Ma Inc. | Assay for JC virus antibodies |
| US8343706B2 (en) | 2010-01-25 | 2013-01-01 | International Business Machines Corporation | Fluorine-free fused ring heteroaromatic photoacid generators and resist compositions containing the same |
| LT3575792T (lt) | 2011-05-31 | 2023-03-10 | Biogen Ma Inc. | Pdl rizikos vertinimo būdas |
| WO2014193804A1 (en) | 2013-05-28 | 2014-12-04 | Biogen Idec Ma Inc. | Method of assessing risk of pml |
| WO2019246455A1 (en) | 2018-06-20 | 2019-12-26 | Progenity, Inc. | Treatment of a disease of the gastrointestinal tract with an integrin inhibitor |
| ES3003232T3 (en) | 2018-10-30 | 2025-03-10 | Gilead Sciences Inc | Compounds for inhibition of alpha4beta7 integrin |
| ES2987796T3 (es) | 2018-10-30 | 2024-11-18 | Gilead Sciences Inc | Derivados de N-benzoil-fenilalanina como inhibidores de la integrina alfa4beta7 para el tratamiento de enfermedades inflamatorias |
| CN112969687B (zh) | 2018-10-30 | 2024-08-23 | 吉利德科学公司 | 作为α4β7整合素抑制剂的喹啉衍生物 |
| CA3114240C (en) | 2018-10-30 | 2023-09-05 | Gilead Sciences, Inc. | Imidazopyridine derivatives as alpha4beta7 integrin inhibitors |
| CN111197057B (zh) * | 2018-11-19 | 2024-04-19 | 中国科学院分子细胞科学卓越创新中心 | 调控免疫细胞迁移的组合物和方法 |
| CN114222730B (zh) | 2019-08-14 | 2024-09-10 | 吉利德科学公司 | 用于抑制α4β7整合素的化合物 |
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-
2003
- 2003-05-26 TW TW092114184A patent/TW200307671A/zh unknown
- 2003-05-27 AU AU2003237302A patent/AU2003237302B8/en not_active Ceased
- 2003-05-27 WO PCT/US2003/017150 patent/WO2003099231A2/en not_active Ceased
- 2003-05-27 EP EP03736768A patent/EP1507533B1/en not_active Expired - Lifetime
- 2003-05-27 EA EA200401561A patent/EA008180B1/ru not_active IP Right Cessation
- 2003-05-27 AT AT03736768T patent/ATE464298T1/de not_active IP Right Cessation
- 2003-05-27 JP JP2004506758A patent/JP4413135B2/ja not_active Expired - Fee Related
- 2003-05-27 CN CNB038112582A patent/CN1311829C/zh not_active Expired - Fee Related
- 2003-05-27 DE DE60332109T patent/DE60332109D1/de not_active Expired - Lifetime
- 2003-05-27 MX MXPA04011657A patent/MXPA04011657A/es active IP Right Grant
- 2003-05-27 US US10/494,788 patent/US7335663B2/en not_active Expired - Fee Related
- 2003-05-27 US US10/447,208 patent/US7008949B2/en not_active Expired - Fee Related
- 2003-05-27 CA CA002480756A patent/CA2480756A1/en not_active Abandoned
- 2003-05-27 BR BR0309619-0A patent/BR0309619A/pt not_active IP Right Cessation
- 2003-05-27 NZ NZ535723A patent/NZ535723A/en unknown
-
2004
- 2004-09-28 IL IL164323A patent/IL164323A/en not_active IP Right Cessation
- 2004-10-01 ZA ZA200407944A patent/ZA200407944B/en unknown
- 2004-12-01 NO NO20045276A patent/NO20045276L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL164323A0 (en) | 2005-12-18 |
| MXPA04011657A (es) | 2005-08-18 |
| US7008949B2 (en) | 2006-03-07 |
| US20050130999A1 (en) | 2005-06-16 |
| ATE464298T1 (de) | 2010-04-15 |
| CN1652789A (zh) | 2005-08-10 |
| AU2003237302A1 (en) | 2003-12-12 |
| AU2003237302B2 (en) | 2008-03-06 |
| EA200401561A1 (ru) | 2005-06-30 |
| EP1507533B1 (en) | 2010-04-14 |
| US7335663B2 (en) | 2008-02-26 |
| EP1507533A2 (en) | 2005-02-23 |
| NZ535723A (en) | 2005-08-26 |
| EA008180B1 (ru) | 2007-04-27 |
| AU2003237302B8 (en) | 2008-04-03 |
| DE60332109D1 (de) | 2010-05-27 |
| TW200307671A (en) | 2003-12-16 |
| CN1311829C (zh) | 2007-04-25 |
| US20040142954A1 (en) | 2004-07-22 |
| JP4413135B2 (ja) | 2010-02-10 |
| WO2003099231A3 (en) | 2004-01-22 |
| NO20045276L (no) | 2004-12-01 |
| BR0309619A (pt) | 2005-06-28 |
| JP2005529155A (ja) | 2005-09-29 |
| IL164323A (en) | 2010-02-17 |
| ZA200407944B (en) | 2006-07-26 |
| EP1507533A4 (en) | 2007-05-23 |
| WO2003099231A2 (en) | 2003-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |