CA2948436A1 - Novel compounds useful as s100-inhibitors - Google Patents
Novel compounds useful as s100-inhibitors Download PDFInfo
- Publication number
- CA2948436A1 CA2948436A1 CA2948436A CA2948436A CA2948436A1 CA 2948436 A1 CA2948436 A1 CA 2948436A1 CA 2948436 A CA2948436 A CA 2948436A CA 2948436 A CA2948436 A CA 2948436A CA 2948436 A1 CA2948436 A1 CA 2948436A1
- Authority
- CA
- Canada
- Prior art keywords
- oxo
- tetraen
- dodeca
- trifluoromethyl
- triazatricyclo
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 319
- 239000003112 inhibitor Substances 0.000 title abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 41
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 39
- 201000011510 cancer Diseases 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 161
- 229910052757 nitrogen Inorganic materials 0.000 claims description 148
- 238000000034 method Methods 0.000 claims description 147
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 126
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 124
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 115
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 108
- -1 3-methoxypropyl Chemical group 0.000 claims description 106
- 229910052736 halogen Inorganic materials 0.000 claims description 100
- 150000002367 halogens Chemical class 0.000 claims description 99
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 88
- 125000000623 heterocyclic group Chemical group 0.000 claims description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 49
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 125000002947 alkylene group Chemical group 0.000 claims description 41
- 125000005842 heteroatom Chemical group 0.000 claims description 35
- ZOUTYVWHWSUKPL-NOZJJQNGSA-N C[C@H](CS)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(O)=O Chemical compound C[C@H](CS)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(O)=O ZOUTYVWHWSUKPL-NOZJJQNGSA-N 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 23
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 20
- 125000004122 cyclic group Chemical group 0.000 claims description 19
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 18
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- YJRDHMUPONVWTE-UHFFFAOYSA-N 5-methoxy-2-(4-phenoxyanilino)benzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 YJRDHMUPONVWTE-UHFFFAOYSA-N 0.000 claims description 9
- VALZSZJVEFACEZ-UHFFFAOYSA-N azetidine-3-carboxamide Chemical compound NC(=O)C1CNC1 VALZSZJVEFACEZ-UHFFFAOYSA-N 0.000 claims description 9
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 8
- DGOYLVBDCVINQZ-UHFFFAOYSA-N oxane-4-carboxamide Chemical compound NC(=O)C1CCOCC1 DGOYLVBDCVINQZ-UHFFFAOYSA-N 0.000 claims description 8
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 7
- 239000011570 nicotinamide Substances 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
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- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 4
- 102200078752 rs201827340 Human genes 0.000 claims description 4
- PTUCPHGSAFOJAU-MGONOCMRSA-N (4s)-5-amino-4-[[(2s)-2-[[(2s)-2-[[(4-bromophenyl)-hydroxyphosphoryl]methyl]-3-[3-[4-(3-chlorophenyl)phenyl]-1,2-oxazol-5-yl]propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoic acid Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N)CP(O)(=O)C=1C=CC(Br)=CC=1)C(ON=1)=CC=1C(C=C1)=CC=C1C1=CC=CC(Cl)=C1 PTUCPHGSAFOJAU-MGONOCMRSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- UUVCRNTVNKTNRK-UHFFFAOYSA-N pyridine-2,6-dicarboxamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=N1 UUVCRNTVNKTNRK-UHFFFAOYSA-N 0.000 claims description 2
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims 1
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- 230000003993 interaction Effects 0.000 abstract description 11
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- 102000015279 Basigin Human genes 0.000 abstract description 2
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- 101000669447 Homo sapiens Toll-like receptor 4 Proteins 0.000 abstract 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 252
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 250
- 239000011541 reaction mixture Substances 0.000 description 241
- 239000000243 solution Substances 0.000 description 200
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 198
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 183
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 168
- 238000006243 chemical reaction Methods 0.000 description 165
- 239000007787 solid Substances 0.000 description 146
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 126
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 126
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- 239000012043 crude product Substances 0.000 description 110
- 229910052739 hydrogen Inorganic materials 0.000 description 92
- 239000000377 silicon dioxide Substances 0.000 description 87
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 86
- 238000002360 preparation method Methods 0.000 description 79
- 239000012267 brine Substances 0.000 description 73
- 239000012074 organic phase Substances 0.000 description 73
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 73
- 239000003480 eluent Substances 0.000 description 66
- 229940086542 triethylamine Drugs 0.000 description 66
- 238000004587 chromatography analysis Methods 0.000 description 64
- 238000004007 reversed phase HPLC Methods 0.000 description 58
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 48
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- HAADRTMPUSJNOI-UHFFFAOYSA-N 5,6-dichloro-1h-benzimidazol-2-amine Chemical compound ClC1=C(Cl)C=C2NC(N)=NC2=C1 HAADRTMPUSJNOI-UHFFFAOYSA-N 0.000 description 47
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 47
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 44
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- XGLLQDIWQRQROJ-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-oxopropanoate Chemical compound COC(=O)C(=O)C(F)(F)F XGLLQDIWQRQROJ-UHFFFAOYSA-N 0.000 description 35
- FRZNJFWQVYAVCE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)phenyl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C=CC(OCCN3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 FRZNJFWQVYAVCE-UHFFFAOYSA-N 0.000 description 33
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- 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]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
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- Biomedical Technology (AREA)
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- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
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| EP14169757.3 | 2014-05-23 | ||
| EP14169757 | 2014-05-23 | ||
| PCT/EP2015/061468 WO2015177367A1 (en) | 2014-05-23 | 2015-05-22 | Novel compounds useful as s100-inhibitors |
Publications (1)
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| CA2948436A1 true CA2948436A1 (en) | 2015-11-26 |
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| EP (1) | EP2991990B1 (OSRAM) |
| JP (1) | JP6580074B2 (OSRAM) |
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| CN (1) | CN106414448B (OSRAM) |
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| MX (1) | MX2016014483A (OSRAM) |
| WO (1) | WO2015177367A1 (OSRAM) |
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| WO2019208290A1 (ja) | 2018-04-27 | 2019-10-31 | 国立大学法人 岡山大学 | 抗ｓ１００ａ８／ａ９抗体とその用途 |
| US11197908B2 (en) | 2018-07-17 | 2021-12-14 | The Board Of Trustees Of The University Of Arkansas | Peptoids and methods for attenuating inflammatory response |
| CN114555119A (zh) | 2019-10-30 | 2022-05-27 | 国立大学法人冈山大学 | 炎症性肺疾病的预防和/或治疗剂 |
| WO2023209141A1 (en) | 2022-04-29 | 2023-11-02 | Westfälische Wilhelms-Universität Münster | Benzo[d]imidazo[1,2-a]imidazoles and their use in diagnosis |
| WO2025132458A1 (en) | 2023-12-18 | 2025-06-26 | Chiesi Farmaceutici S.P.A. | Pyridazinyl amino derivatives as alk5 inhibitors |
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| US6248755B1 (en) | 1999-04-06 | 2001-06-19 | Merck & Co., Inc. | Pyrrolidine modulators of chemokine receptor activity |
| AR029489A1 (es) | 2000-03-10 | 2003-07-02 | Euro Celtique Sa | Piridinas, pirimidinas, pirazinas, triazinas sustituidas por arilo, composiciones farmaceuticas y el uso de las mismas para la manufactura de un medicamento |
| US7361678B2 (en) * | 2002-03-05 | 2008-04-22 | Transtech Pharma, Inc. | Azole derivatives and fused bicyclic azole derivatives as therapeutic agents |
| DE60125373T2 (de) | 2000-07-26 | 2007-10-18 | Smithkline Beecham P.L.C., Brentford | Aminopiperidin chinoline und ihre azaisosteren analoga mit antibakterieller wirkung |
| AU2002245590B2 (en) * | 2001-03-05 | 2006-06-29 | Transtech Pharma, Inc. | Benzimidazole derivatives as therapeutic agents |
| GB0117506D0 (en) | 2001-07-18 | 2001-09-12 | Bayer Ag | Imidazopyridinones |
| SE0104331D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Novel compounds |
| US20060111416A1 (en) | 2004-11-24 | 2006-05-25 | Lane Charlotte A L | Octahydropyrrolo[3,4-C]pyrrole derivatives |
| US8088767B2 (en) | 2006-09-28 | 2012-01-03 | Exelixis, Inc. | JAK-2 modulators and methods of use |
| US7919498B2 (en) | 2007-03-23 | 2011-04-05 | Amgen Inc. | Substituted pyrazolo[3,4-d]pyrimidines as PI3K inhibitors |
| EP1986009A1 (en) * | 2007-04-26 | 2008-10-29 | Active Biotech AB | Screening method |
| CA2689980A1 (en) | 2007-06-13 | 2008-12-24 | Glaxosmithkline Llc | Farnesoid x receptor agonists |
| WO2009093747A1 (en) * | 2008-01-22 | 2009-07-30 | Takeda Pharmaceutical Company Limited | Tricyclic compounds having corticotropin-releasing factor antagonistic activity and pharmaceutical compositions containing them |
| TW201004941A (en) | 2008-07-16 | 2010-02-01 | Wyeth Corp | Alpha7 nicotinic acetylcholine receptor inhibitors |
| WO2010101949A1 (en) | 2009-03-02 | 2010-09-10 | Sirtris Pharmaceuticals, Inc. | 8-substituted quinolines and related analogs as sirtuin modulators |
| ES2552514T3 (es) | 2011-11-03 | 2015-11-30 | Hoffmann-La Roche Ag | Compuestos bicíclicos de piperazina |
| GB201321728D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
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- 2015-05-22 MX MX2016014483A patent/MX2016014483A/es unknown
- 2015-05-22 BR BR112016024749A patent/BR112016024749A2/pt not_active IP Right Cessation
- 2015-05-22 WO PCT/EP2015/061468 patent/WO2015177367A1/en not_active Ceased
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- 2015-05-22 KR KR1020167035803A patent/KR20170005868A/ko not_active Withdrawn
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- 2015-05-22 JP JP2016568812A patent/JP6580074B2/ja not_active Expired - Fee Related
- 2015-05-22 CN CN201580026356.5A patent/CN106414448B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR20170005868A (ko) | 2017-01-16 |
| US20170204098A1 (en) | 2017-07-20 |
| AU2015261775B2 (en) | 2019-07-11 |
| CN106414448B (zh) | 2019-04-19 |
| EP2991990A1 (en) | 2016-03-09 |
| AU2015261775A1 (en) | 2016-12-08 |
| BR112016024749A2 (pt) | 2017-08-15 |
| EA030604B1 (ru) | 2018-08-31 |
| WO2015177367A1 (en) | 2015-11-26 |
| EA201692405A1 (ru) | 2017-06-30 |
| CN106414448A (zh) | 2017-02-15 |
| MX2016014483A (es) | 2017-01-23 |
| EP2991990B1 (en) | 2017-02-01 |
| JP6580074B2 (ja) | 2019-09-25 |
| JP2017516772A (ja) | 2017-06-22 |
| US9771372B2 (en) | 2017-09-26 |
| HK1221463A1 (en) | 2017-06-02 |
| ES2620751T3 (es) | 2017-06-29 |
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| FZDE | Discontinued |
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| FZDE | Discontinued |
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