CA2594777A1 - Indoles useful in the treatment of inflamation - Google Patents
Indoles useful in the treatment of inflamation Download PDFInfo
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- CA2594777A1 CA2594777A1 CA002594777A CA2594777A CA2594777A1 CA 2594777 A1 CA2594777 A1 CA 2594777A1 CA 002594777 A CA002594777 A CA 002594777A CA 2594777 A CA2594777 A CA 2594777A CA 2594777 A1 CA2594777 A1 CA 2594777A1
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- 238000011282 treatment Methods 0.000 title claims abstract description 31
- 150000002475 indoles Chemical class 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 760
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 230000000694 effects Effects 0.000 claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
- 206010061218 Inflammation Diseases 0.000 claims abstract description 20
- 230000004054 inflammatory process Effects 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 17
- 102000042256 MAPEG family Human genes 0.000 claims abstract description 13
- 108091077604 MAPEG family Proteins 0.000 claims abstract description 13
- 230000005764 inhibitory process Effects 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 223
- 239000000203 mixture Substances 0.000 claims description 127
- -1 -N3 Chemical group 0.000 claims description 95
- 125000001424 substituent group Chemical group 0.000 claims description 95
- 238000000034 method Methods 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 125000005843 halogen group Chemical group 0.000 claims description 71
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 50
- 230000008569 process Effects 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- 238000002360 preparation method Methods 0.000 claims description 39
- 125000002947 alkylene group Chemical group 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 30
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- 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 29
- 125000004429 atom Chemical group 0.000 claims description 25
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 25
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 25
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- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 230000007062 hydrolysis Effects 0.000 claims description 20
- 238000006460 hydrolysis reaction Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 102100033076 Prostaglandin E synthase Human genes 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 101710096361 Prostaglandin E synthase Proteins 0.000 claims description 16
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- 125000001041 indolyl group Chemical group 0.000 claims description 16
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 15
- 125000001246 bromo group Chemical group Br* 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 14
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000010511 deprotection reaction Methods 0.000 claims description 11
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 10
- 239000002671 adjuvant Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 229940124597 therapeutic agent Drugs 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 125000004450 alkenylene group Chemical group 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000002346 iodo group Chemical group I* 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000006850 spacer group Chemical group 0.000 claims description 8
- 229910052727 yttrium Inorganic materials 0.000 claims description 8
- 239000011701 zinc Substances 0.000 claims description 8
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 7
- GWNVDXQDILPJIG-SHSCPDMUSA-N Leukotriene C4 Natural products CCCCCC=C/CC=C/C=C/C=C/C(SCC(NC(=O)CCC(N)C(=O)O)C(=O)NCC(=O)O)C(O)CCCC(=O)O GWNVDXQDILPJIG-SHSCPDMUSA-N 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 7
- 238000005886 esterification reaction Methods 0.000 claims description 7
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 7
- GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 claims description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 238000005809 transesterification reaction Methods 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 201000004624 Dermatitis Diseases 0.000 claims description 5
- 239000007818 Grignard reagent Substances 0.000 claims description 5
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- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 150000004795 grignard reagents Chemical class 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
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- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 102000004023 5-Lipoxygenase-Activating Proteins Human genes 0.000 claims description 4
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- 150000001340 alkali metals Chemical group 0.000 claims description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
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- 230000020477 pH reduction Effects 0.000 claims description 4
- WQNVSQDMXNPYNW-UHFFFAOYSA-N 1,1,2,2-tetraethoxyethene Chemical compound CCOC(OCC)=C(OCC)OCC WQNVSQDMXNPYNW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- SZBNZTGCAMLMJY-UHFFFAOYSA-N 3,4-dimethoxycyclobut-3-ene-1,2-dione Chemical compound COC1=C(OC)C(=O)C1=O SZBNZTGCAMLMJY-UHFFFAOYSA-N 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
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- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- VMVZGGPZNHFGKS-UHFFFAOYSA-N ethyl n-(oxomethylidene)carbamate Chemical compound CCOC(=O)N=C=O VMVZGGPZNHFGKS-UHFFFAOYSA-N 0.000 claims description 3
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- VMVNZNXAVJHNDJ-UHFFFAOYSA-N methyl 2,2,2-trifluoroacetate Chemical compound COC(=O)C(F)(F)F VMVNZNXAVJHNDJ-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
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- IZISMXMXCLUHGI-UHFFFAOYSA-N n-(4-chlorophenyl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=C(Cl)C=C1 IZISMXMXCLUHGI-UHFFFAOYSA-N 0.000 description 1
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- 102000005962 receptors Human genes 0.000 description 1
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- 102220315634 rs1196125127 Human genes 0.000 description 1
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- UAWABSHMGXMCRK-UHFFFAOYSA-L samarium(ii) iodide Chemical compound I[Sm]I UAWABSHMGXMCRK-UHFFFAOYSA-L 0.000 description 1
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- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
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- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (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)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Virology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64452005P | 2005-01-19 | 2005-01-19 | |
| US64452505P | 2005-01-19 | 2005-01-19 | |
| US60/644,525 | 2005-01-19 | ||
| US60/644,520 | 2005-01-19 | ||
| PCT/GB2005/004982 WO2006077367A1 (en) | 2005-01-19 | 2005-12-22 | Indoles useful in the treatment of inflamation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2594777A1 true CA2594777A1 (en) | 2006-07-27 |
Family
ID=36010890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002594777A Abandoned CA2594777A1 (en) | 2005-01-19 | 2005-12-22 | Indoles useful in the treatment of inflamation |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20100197687A1 (https=) |
| EP (1) | EP1841736A1 (https=) |
| JP (1) | JP2008527030A (https=) |
| AR (1) | AR053111A1 (https=) |
| CA (1) | CA2594777A1 (https=) |
| TW (1) | TW200637818A (https=) |
| WO (1) | WO2006077367A1 (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0519774A2 (pt) | 2005-01-19 | 2009-02-10 | Biolipox Ab | composto ou um sal farmaceuticamente aceitÁvel do mesmo, formulaÇço farmacÊutica, uso de um composto ou um sal farmaceuticamente aceitÁvel do mesmo, mÉtodo de tratamento de uma doenÇa em que inibiÇço da atividade de um membro da famÍlia mapeg É desejada e/ou necessÁria, produto combinado, e, processo para a preparaÇço de um composto |
| US8399666B2 (en) | 2005-11-04 | 2013-03-19 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein (FLAP) inhibitors |
| GB2431927B (en) | 2005-11-04 | 2010-03-17 | Amira Pharmaceuticals Inc | 5-Lipoxygenase-activating protein (FLAP) inhibitors |
| US7977359B2 (en) | 2005-11-04 | 2011-07-12 | Amira Pharmaceuticals, Inc. | 5-lipdxygenase-activating protein (FLAP) inhibitors |
| WO2008009924A2 (en) * | 2006-07-18 | 2008-01-24 | Biolipox Ab | Indoles useful in the treatment of inflammation |
| MX2009011210A (es) * | 2007-04-16 | 2009-10-30 | Abbott Lab | Inhibidores de mcl1 de indol 7-no sustituido. |
| TW200920369A (en) | 2007-10-26 | 2009-05-16 | Amira Pharmaceuticals Inc | 5-lipoxygenase activating protein (flap) inhibitor |
| JP5791500B2 (ja) | 2008-05-23 | 2015-10-07 | パンミラ ファーマシューティカルズ，エルエルシー． | ５−リポキシゲナーゼ活性化タンパク質阻害剤 |
| US8546431B2 (en) | 2008-10-01 | 2013-10-01 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein (FLAP) inhibitors |
| US20120029016A1 (en) | 2008-12-30 | 2012-02-02 | Biolipox Ab | Indoles Useful in the Treatment of Inflammation |
| US8481731B2 (en) | 2009-06-24 | 2013-07-09 | Boehringer Ingelheim International Gmbh | Compounds, pharmaceutical composition and methods relating thereto |
| EA201200046A1 (ru) | 2009-06-24 | 2012-08-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Новые соединения, фармацевтическая композиция и связанные с ними способы |
| JP2012211085A (ja) * | 2009-08-12 | 2012-11-01 | Kyowa Hakko Kirin Co Ltd | ヘッジホッグシグナル阻害剤 |
| GB201006846D0 (en) | 2010-04-23 | 2010-06-09 | Glaxo Group Ltd | Novel compounds |
| WO2014081756A1 (en) * | 2012-11-20 | 2014-05-30 | Biogen Idec Ma Inc. | S1p and/or atx modulating agents |
| CA2894536C (en) | 2012-12-18 | 2020-07-28 | Vertex Pharmaceuticals Incorporated | Mannose derivatives for treating bacterial infections |
| MX2015012472A (es) | 2013-03-12 | 2016-02-10 | Vertex Pharma | Derivados de manosa para el tratamiento de infecciones bacterianas. |
| US10080748B2 (en) | 2014-02-04 | 2018-09-25 | Bioscience Pharma Partners, Llc | Use of flap inhibitors to reduce neuroinflammation mediated injury in the central nervous system |
| CN104974187A (zh) * | 2014-04-10 | 2015-10-14 | 吉林省博创药业有限公司 | 菲罗啉类衍生物及其制备方法和应用 |
| DK3240785T3 (da) | 2014-12-29 | 2021-09-27 | Us Health | Småmolekylede hæmmere af laktasedehydrogenase og fremgangsmåder til brug deraf |
| CN104628621A (zh) * | 2015-01-22 | 2015-05-20 | 湖南华腾制药有限公司 | 一种氟取代吲哚衍生物的制备方法 |
| CN105777610B (zh) * | 2015-10-16 | 2018-10-09 | 浙江沙星科技有限公司 | 一种制备4-氯-2-(三氟乙酰基)苯胺盐酸盐水合物的方法 |
| AU2017275657B2 (en) | 2016-06-02 | 2021-08-19 | Novartis Ag | Potassium channel modulators |
| PL3571193T3 (pl) | 2017-01-23 | 2022-04-25 | Cadent Therapeutics, Inc. | Modulatory kanału potasowego |
| US11690824B2 (en) | 2018-04-10 | 2023-07-04 | The General Hospital Corporation | Antibacterial compounds |
| JP7542538B2 (ja) | 2018-09-18 | 2024-08-30 | ニカング セラピューティクス， インコーポレイテッド | Ｓｒｃホモロジー－２ホスファターゼ阻害剤としての縮合三環式環誘導体 |
| EP3870291A1 (en) | 2018-10-22 | 2021-09-01 | Cadent Therapeutics, Inc. | Crystalline forms of potassium channel modulators |
| CN110563673A (zh) * | 2019-07-23 | 2019-12-13 | 武汉药明康德新药开发有限公司 | 一种(5-(4-(二氟甲氧基)-3-异丙氧基苯基)呋喃-3-基)甲醇的制备方法 |
| WO2025175249A1 (en) | 2024-02-14 | 2025-08-21 | Olema Pharmaceuticals, Inc. | Estrogen receptor modulators and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5081138A (en) * | 1986-12-17 | 1992-01-14 | Merck Frosst Canada, Inc. | 3-hetero-substituted-n-benzyl-indoles and prevention of leucotriene synthesis therewith |
| US4960786A (en) * | 1989-04-24 | 1990-10-02 | Merrell Dow Pharmaceuticals Inc. | Excitatory amino acid antagonists |
| US5081145A (en) * | 1990-02-01 | 1992-01-14 | Merck Frosst Canada, Inc. | Indole-2-alkanoic acids compositions of and anti allergic use thereof |
| US5374615A (en) * | 1990-10-31 | 1994-12-20 | E. R. Squibb & Sons, Inc. | Indole- and benzimidazole-substituted imidazole and benzimidazole derivatives |
| US5189054A (en) * | 1990-11-02 | 1993-02-23 | Merrell Dow Pharmaceuticals Inc. | 3-amidoindolyl derivatives and pharmaceutical compositions thereof |
| US5294722A (en) * | 1992-04-16 | 1994-03-15 | E. R. Squibb & Sons, Inc. | Process for the preparation of imidazoles useful in angiotensin II antagonism |
| US5236916A (en) * | 1992-05-26 | 1993-08-17 | E. R. Squibb & Sons, Inc. | Oxadiazinone substituted indole and benzimidazole derivatives |
| TW229140B (https=) * | 1992-06-05 | 1994-09-01 | Shell Internat Res Schappej B V | |
| JPH10510510A (ja) * | 1994-06-09 | 1998-10-13 | スミスクライン・ビーチャム・コーポレイション | エンドセリン受容体拮抗物質 |
| US6630496B1 (en) * | 1996-08-26 | 2003-10-07 | Genetics Institute Llc | Inhibitors of phospholipase enzymes |
| GB9716657D0 (en) * | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| GB9716656D0 (en) * | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| HU227568B1 (en) * | 1997-12-24 | 2011-08-29 | Sanofi Aventis Deutschland | Indole derivatives, as inhibitors os factor xa |
| GB9803228D0 (en) * | 1998-02-17 | 1998-04-08 | Zeneca Ltd | Chemical compounds |
| EP1062216A1 (en) * | 1998-02-25 | 2000-12-27 | Genetics Institute, Inc. | Inhibitors of phospholipase a2 |
| US6828344B1 (en) * | 1998-02-25 | 2004-12-07 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| US6916841B2 (en) * | 1998-02-25 | 2005-07-12 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| US6500853B1 (en) * | 1998-02-28 | 2002-12-31 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| GB9902455D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902452D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902453D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| JP2001069477A (ja) * | 1999-08-31 | 2001-03-16 | Sony Corp | 番組提供システム及び番組提供方法 |
| US6353007B1 (en) * | 2000-07-13 | 2002-03-05 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 1-(4-aminophenyl)indoles and their use as anti-inflammatory agents |
| PL366068A1 (en) * | 2000-10-10 | 2005-01-24 | Smithkline Beecham Corporation | Substituted indoles, pharmaceutical compositions containing such indoles and their use as ppar-gamma binding agents |
| GB0217920D0 (en) * | 2002-04-23 | 2002-09-11 | Aventis Pharm Prod Inc | Interleukin-4 Gene Expression inhibitors |
| SE0302035D0 (sv) * | 2003-07-09 | 2003-07-09 | Biolipox Ab | New compound |
| MXPA06014535A (es) * | 2004-06-18 | 2007-06-05 | Biolipox Ab | Indoles utiles en el tratamiento de la inflamacion. |
| DE602005014233D1 (de) * | 2004-06-18 | 2009-06-10 | Biolipox Ab | Zur behandlung von entzündungen geeignete indole |
| RU2007101703A (ru) * | 2004-06-18 | 2008-07-27 | Биолипокс Аб (Se) | Индолы, полезные при лечении воспаления |
| BRPI0519774A2 (pt) * | 2005-01-19 | 2009-02-10 | Biolipox Ab | composto ou um sal farmaceuticamente aceitÁvel do mesmo, formulaÇço farmacÊutica, uso de um composto ou um sal farmaceuticamente aceitÁvel do mesmo, mÉtodo de tratamento de uma doenÇa em que inibiÇço da atividade de um membro da famÍlia mapeg É desejada e/ou necessÁria, produto combinado, e, processo para a preparaÇço de um composto |
| US20090069384A1 (en) * | 2005-01-19 | 2009-03-12 | Biolipox Ab | Thienopyrroles useful in the treatment of inflammation |
| US20080249091A1 (en) * | 2005-01-19 | 2008-10-09 | Benjamin Pelcman | Indoles Useful in the Treatment of Inflammation |
| EP1841766A1 (en) * | 2005-01-19 | 2007-10-10 | Biolipox AB | Pyrrolopyridines useful in the treatment of inflammation |
| JP2008527028A (ja) * | 2005-01-19 | 2008-07-24 | バイオリポックス エービー | 炎症の治療に有用なインドール類 |
-
2005
- 2005-12-22 JP JP2007551728A patent/JP2008527030A/ja not_active Withdrawn
- 2005-12-22 US US11/795,632 patent/US20100197687A1/en not_active Abandoned
- 2005-12-22 WO PCT/GB2005/004982 patent/WO2006077367A1/en not_active Ceased
- 2005-12-22 EP EP05823723A patent/EP1841736A1/en not_active Withdrawn
- 2005-12-22 CA CA002594777A patent/CA2594777A1/en not_active Abandoned
- 2005-12-28 AR ARP050105596A patent/AR053111A1/es not_active Application Discontinuation
- 2005-12-28 TW TW094146943A patent/TW200637818A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR053111A1 (es) | 2007-04-25 |
| EP1841736A1 (en) | 2007-10-10 |
| US20100197687A1 (en) | 2010-08-05 |
| JP2008527030A (ja) | 2008-07-24 |
| WO2006077367A1 (en) | 2006-07-27 |
| TW200637818A (en) | 2006-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |