CA2707789A1 - Phenyl acetic acid derivatives as inflammation modulators - Google Patents
Phenyl acetic acid derivatives as inflammation modulators Download PDFInfo
- Publication number
- CA2707789A1 CA2707789A1 CA2707789A CA2707789A CA2707789A1 CA 2707789 A1 CA2707789 A1 CA 2707789A1 CA 2707789 A CA2707789 A CA 2707789A CA 2707789 A CA2707789 A CA 2707789A CA 2707789 A1 CA2707789 A1 CA 2707789A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- alkyl
- chloro
- acid
- 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
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title description 4
- 206010061218 Inflammation Diseases 0.000 title description 3
- 230000004054 inflammatory process Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 187
- -1 alky I Chemical group 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 62
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 34
- 230000008569 process Effects 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 208000006673 asthma Diseases 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 229910052723 transition metal Inorganic materials 0.000 claims description 21
- 150000003624 transition metals Chemical class 0.000 claims description 21
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 19
- 239000003446 ligand Substances 0.000 claims description 17
- 230000007704 transition Effects 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 12
- 230000010512 thermal transition Effects 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 7
- 201000004624 Dermatitis Diseases 0.000 claims description 7
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 6
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
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- 229910001511 metal iodide Chemical class 0.000 claims description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 4
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 3
- AXXLAOYVJJFFKW-UHFFFAOYSA-N B1CCCCCCCC1C1CCCCCCCC1 Chemical compound B1CCCCCCCC1C1CCCCCCCC1 AXXLAOYVJJFFKW-UHFFFAOYSA-N 0.000 claims description 2
- XGJJEPKJCFKYKE-UHFFFAOYSA-N ditert-butyl-[2-tert-butyl-6-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane Chemical group CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC(C(C)(C)C)=C1P(C(C)(C)C)C(C)(C)C XGJJEPKJCFKYKE-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
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- 229910002666 PdCl2 Inorganic materials 0.000 claims 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 2
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- 238000006243 chemical reaction Methods 0.000 description 33
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
- DKSKRBVXRDGYAS-UHFFFAOYSA-N 2-[4-[4-(butylcarbamoyl)-2-[(2,4-dichlorophenyl)sulfonylamino]phenoxy]-3-methoxyphenyl]acetic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1S(=O)(=O)NC1=CC(C(=O)NCCCC)=CC=C1OC1=CC=C(CC(O)=O)C=C1OC DKSKRBVXRDGYAS-UHFFFAOYSA-N 0.000 description 24
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- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- 125000001424 substituent group Chemical group 0.000 description 19
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- YLGRTLMDMVAFNI-UHFFFAOYSA-N tributyl(prop-2-enyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)CC=C YLGRTLMDMVAFNI-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000004385 trihaloalkyl group Chemical group 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 229960003223 tripelennamine Drugs 0.000 description 1
- 229960001128 triprolidine Drugs 0.000 description 1
- CBEQULMOCCWAQT-WOJGMQOQSA-N triprolidine Chemical compound C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C/CN1CCCC1 CBEQULMOCCWAQT-WOJGMQOQSA-N 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
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- 231100000397 ulcer Toxicity 0.000 description 1
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- 210000003932 urinary bladder Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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- 229940124549 vasodilator Drugs 0.000 description 1
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- 229960003048 vinblastine Drugs 0.000 description 1
- 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
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- 229940087652 vioxx Drugs 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- 235000019160 vitamin B3 Nutrition 0.000 description 1
- 239000011708 vitamin B3 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
- 239000011726 vitamin B6 Substances 0.000 description 1
- 150000003704 vitamin D3 derivatives Chemical class 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical class OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Otolaryngology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US843307P | 2007-12-19 | 2007-12-19 | |
| US61/008,433 | 2007-12-19 | ||
| PCT/US2008/013833 WO2009085177A1 (en) | 2007-12-19 | 2008-12-18 | Phenyl acetic acid derivatives as inflammation modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2707789A1 true CA2707789A1 (en) | 2009-07-09 |
Family
ID=40564868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2707789A Abandoned CA2707789A1 (en) | 2007-12-19 | 2008-12-18 | Phenyl acetic acid derivatives as inflammation modulators |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8183293B2 (https=) |
| EP (1) | EP2231595B1 (https=) |
| JP (1) | JP5437267B2 (https=) |
| KR (1) | KR20100102668A (https=) |
| CN (1) | CN101903338A (https=) |
| AR (1) | AR071279A1 (https=) |
| AU (1) | AU2008343924B2 (https=) |
| BR (1) | BRPI0821197A2 (https=) |
| CA (1) | CA2707789A1 (https=) |
| CL (1) | CL2008003832A1 (https=) |
| CO (1) | CO6321234A2 (https=) |
| CR (1) | CR11572A (https=) |
| EA (1) | EA201001029A1 (https=) |
| ES (1) | ES2471919T3 (https=) |
| IL (1) | IL206069A0 (https=) |
| MA (1) | MA32013B1 (https=) |
| PE (1) | PE20091526A1 (https=) |
| TN (1) | TN2010000223A1 (https=) |
| TW (1) | TW200940051A (https=) |
| WO (1) | WO2009085177A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| EP2790696A1 (en) | 2011-12-16 | 2014-10-22 | Atopix Therapeutics Limited | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
| US9974759B2 (en) * | 2013-05-31 | 2018-05-22 | Indiana University Research And Technology Corporation | Beta 2 adrenoceptor antagonists for treating orthostatic hypotension |
| ES2991300T3 (es) * | 2015-02-13 | 2024-12-03 | Inserm Institut Nat De La Sante Et De Larecherche Medicale | Antagonistas de PTGDR-1 y/o PTGDR-2 para prevenir y/o tratar lupus eritematoso sistémico |
| AR107928A1 (es) | 2016-03-22 | 2018-06-28 | Merck Sharp & Dohme | Moduladores alostéricos de receptores de acetilcolina nicotínicos |
| ES2733477T3 (es) * | 2017-07-04 | 2019-11-29 | Fis Fabbrica Italiana Sintetici Spa | Procedimiento eficaz para la preparación de sitagliptina a través de una preparación muy eficaz del intermedio ácido 2,4,5-trifluorofenilacético |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB8704158D0 (en) | 1987-02-23 | 1987-04-01 | Wellcome Found | Substituted hydantoin compounds |
| US5849780A (en) | 1992-01-30 | 1998-12-15 | Sanofi | 1-benzenesulfonyl-1-1,3-dihydroindol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| JP3894949B2 (ja) | 1993-06-30 | 2007-03-22 | ザ、ウェルカム、ファンデーション、リミテッド | 抗アテローム性動脈硬化症ジアリール化合物 |
| US5545669A (en) | 1994-06-02 | 1996-08-13 | Adams; Jerry L. | Anti-inflammatory compounds |
| WO1996019455A1 (en) | 1994-12-20 | 1996-06-27 | F. Hoffmann-La Roche Ag | Aryl- and hetaryl-sulfonamide derivatives, their preparation and their use as endothelin antagonists |
| US6008234A (en) | 1996-09-12 | 1999-12-28 | Berlex Laboratories, Inc. | Benzamidine derivatives substituted by cyclic amino acid and cyclic hydroxy acid derivatives and their use as anti-coagulants |
| ATE228513T1 (de) | 1996-09-12 | 2002-12-15 | Schering Ag | Durch cyclische aminosäuren oder cyclische hydroxysäuren substituierte benzamidinderivate und deren verwendung als antikoagulantien |
| TW523506B (en) | 1996-12-18 | 2003-03-11 | Ono Pharmaceutical Co | Sulfonamide or carbamide derivatives and drugs containing the same as active ingredients |
| JPH11202458A (ja) | 1998-01-16 | 1999-07-30 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
| US5929250A (en) | 1997-01-23 | 1999-07-27 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| AU3665199A (en) | 1998-04-29 | 1999-11-16 | Vertex Pharmaceuticals Incorporated | Inhibitors of impdh enzyme |
| AR023659A1 (es) | 1998-09-18 | 2002-09-04 | Vertex Pharma | Un compuesto inhibidor de p38, una composicion farmaceutica que lo comprende y el uso de dicha composicion en el tratamiento y prevencion de estados patologicos |
| US6248739B1 (en) | 1999-01-08 | 2001-06-19 | Pharmacia & Upjohn Company | Quinolinecarboxamides as antiviral agents |
| EA004229B1 (ru) | 1999-03-01 | 2004-02-26 | Пфайзер Продактс Инк. | Оксаминовые кислоты и их производные в качестве лигандов тиреоидных рецепторов |
| US7105564B1 (en) | 1999-03-10 | 2006-09-12 | Shionogi & Co., Ltd. | Pharmaceutical composition comprising a dual antagonist against PGD2/TXA2 receptors having a [2.2.1] or [3.1.1] bicyclic skeleton |
| JP3486408B2 (ja) | 1999-08-23 | 2004-01-13 | 株式会社ビー・エム・エル | 物質のヒトプロスタグランジンｄ２受容体に対する性質の同定方法 |
| US6531291B1 (en) | 1999-11-10 | 2003-03-11 | The Trustees Of Columbia University In The City Of New York | Antimicrobial activity of gemfibrozil and related compounds and derivatives and metabolites thereof |
| US20020072530A1 (en) | 2000-02-01 | 2002-06-13 | Bing-Yan Zhu | Indole and benzimidazole inhibitors of factor Xa |
| US20010047027A1 (en) | 2000-04-12 | 2001-11-29 | Marc Labelle | Prostaglandin D2 receptor antagonists |
| US7084136B2 (en) | 2000-06-02 | 2006-08-01 | Shionogi & Co., Ltd. | Drug composition antagonistic to both PGD2/TXA2 receptors |
| US6878522B2 (en) | 2000-07-07 | 2005-04-12 | Baiyong Li | Methods for the identification of compounds useful for the treatment of disease states mediated by prostaglandin D2 |
| AU2002229611A1 (en) | 2000-12-08 | 2002-06-18 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Use of active compounds capable of modulating the intracellular pathway triggered by the dp receptor in langerhans cells |
| WO2002051805A1 (de) | 2000-12-27 | 2002-07-04 | Bayer Aktiengesellschaft | Indol-derivate |
| JP4279561B2 (ja) | 2001-05-23 | 2009-06-17 | メルク フロスト カナダ リミテツド | プロスタグランジンＤ２受容体拮抗薬としてのジヒドロピロロ［１，２−ａ］インドールおよびテトラヒドロピリド［１，２−ａ］−インドール誘導体 |
| MXPA04001253A (es) | 2001-08-09 | 2004-06-03 | Ono Pharmaceutical Co | Derivados de acidos carboxilicos y agente farmaceutico que comprende los mismos como ingrediente activo. |
| SE0200356D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| SE0200411D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| ATE516277T1 (de) | 2002-03-19 | 2011-07-15 | Ono Pharmaceutical Co | Carbonsäureverbindungen und arzneimittel, die diese verbindungen als wirkstoffe enthalten |
| AU2003231513A1 (en) | 2002-05-16 | 2003-12-02 | Shionogi And Co., Ltd. | Pgd2 receptor antagonist |
| EP2423190A1 (en) | 2002-05-16 | 2012-02-29 | Shionogi&Co., Ltd. | Compounds Exhibiting PGD 2 Receptor Antagonism |
| GB2388540A (en) | 2002-05-17 | 2003-11-19 | Bayer Ag | New use of Ramatroban |
| SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Astrazeneca Ab | Novel compounds |
| TW200307542A (en) | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
| GB0224557D0 (en) | 2002-10-22 | 2002-11-27 | Glaxo Group Ltd | Novel compounds |
| ZA200505523B (en) | 2002-12-20 | 2006-09-27 | Amgen Inc | Asthma and allergic inflammation modulators |
| US20070082907A1 (en) | 2003-11-25 | 2007-04-12 | Eli Lilly And Company | Peroxisome proliferator activated receptor modulators |
| US8148572B2 (en) * | 2005-10-06 | 2012-04-03 | Astrazeneca Ab | Compounds |
| US20080167377A1 (en) * | 2006-12-15 | 2008-07-10 | Alessandra Gaiba | Novel compounds |
| US7960567B2 (en) | 2007-05-02 | 2011-06-14 | Amgen Inc. | Compounds and methods useful for treating asthma and allergic inflammation |
| KR20120038544A (ko) | 2009-07-31 | 2012-04-23 | 판미라 파마슈티칼스, 엘엘씨 | Ｄｐ2 수용체 길항제의 안과용 약학 조성물 |
| CN102596193A (zh) | 2009-07-31 | 2012-07-18 | 潘米拉制药公司 | Dp2受体拮抗的皮肤调配物 |
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2008
- 2008-12-18 ES ES08867490.8T patent/ES2471919T3/es active Active
- 2008-12-18 KR KR1020107015813A patent/KR20100102668A/ko not_active Withdrawn
- 2008-12-18 EP EP08867490.8A patent/EP2231595B1/en active Active
- 2008-12-18 US US12/317,066 patent/US8183293B2/en active Active
- 2008-12-18 CN CN2008801215268A patent/CN101903338A/zh active Pending
- 2008-12-18 JP JP2010539482A patent/JP5437267B2/ja not_active Expired - Fee Related
- 2008-12-18 BR BRPI0821197-3A patent/BRPI0821197A2/pt not_active IP Right Cessation
- 2008-12-18 WO PCT/US2008/013833 patent/WO2009085177A1/en not_active Ceased
- 2008-12-18 EA EA201001029A patent/EA201001029A1/ru unknown
- 2008-12-18 AU AU2008343924A patent/AU2008343924B2/en not_active Ceased
- 2008-12-18 CA CA2707789A patent/CA2707789A1/en not_active Abandoned
- 2008-12-19 TW TW097149926A patent/TW200940051A/zh unknown
- 2008-12-19 CL CL2008003832A patent/CL2008003832A1/es unknown
- 2008-12-19 PE PE2008002152A patent/PE20091526A1/es not_active Application Discontinuation
- 2008-12-19 AR ARP080105608A patent/AR071279A1/es not_active Application Discontinuation
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2010
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- 2010-05-30 IL IL206069A patent/IL206069A0/en unknown
- 2010-07-14 MA MA33012A patent/MA32013B1/fr unknown
- 2010-07-19 CR CR11572A patent/CR11572A/es not_active Application Discontinuation
- 2010-07-19 CO CO10087808A patent/CO6321234A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US8183293B2 (en) | 2012-05-22 |
| AU2008343924A1 (en) | 2009-07-09 |
| BRPI0821197A2 (pt) | 2015-06-16 |
| US20090275659A1 (en) | 2009-11-05 |
| TN2010000223A1 (en) | 2011-11-11 |
| CL2008003832A1 (es) | 2010-03-26 |
| PE20091526A1 (es) | 2009-11-01 |
| ES2471919T3 (es) | 2014-06-27 |
| JP2011507847A (ja) | 2011-03-10 |
| EP2231595B1 (en) | 2014-04-23 |
| CO6321234A2 (es) | 2011-09-20 |
| KR20100102668A (ko) | 2010-09-24 |
| CR11572A (es) | 2010-08-13 |
| TW200940051A (en) | 2009-10-01 |
| AR071279A1 (es) | 2010-06-09 |
| AU2008343924B2 (en) | 2013-01-17 |
| WO2009085177A1 (en) | 2009-07-09 |
| CN101903338A (zh) | 2010-12-01 |
| AU2008343924A2 (en) | 2011-02-17 |
| EA201001029A1 (ru) | 2011-06-30 |
| EP2231595A1 (en) | 2010-09-29 |
| IL206069A0 (en) | 2010-11-30 |
| JP5437267B2 (ja) | 2014-03-12 |
| MA32013B1 (fr) | 2011-01-03 |
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