CA2850925C - (4-phenylimidazol-2-yl) ethylamine derivatives useful as sodium channel modulators - Google Patents
(4-phenylimidazol-2-yl) ethylamine derivatives useful as sodium channel modulators Download PDFInfo
- Publication number
- CA2850925C CA2850925C CA2850925A CA2850925A CA2850925C CA 2850925 C CA2850925 C CA 2850925C CA 2850925 A CA2850925 A CA 2850925A CA 2850925 A CA2850925 A CA 2850925A CA 2850925 C CA2850925 C CA 2850925C
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- Prior art keywords
- compound
- formula
- oxetan
- pain
- imidazol
- Prior art date
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- 108010052164 Sodium Channels Proteins 0.000 title description 12
- 102000018674 Sodium Channels Human genes 0.000 title description 12
- FZBCVZJBMHTMGF-UHFFFAOYSA-N n-ethyl-5-phenyl-1h-imidazol-2-amine Chemical class N1C(NCC)=NC(C=2C=CC=CC=2)=C1 FZBCVZJBMHTMGF-UHFFFAOYSA-N 0.000 title description 2
- 208000002193 Pain Diseases 0.000 claims abstract description 76
- 239000000203 mixture Substances 0.000 claims abstract description 69
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- 239000003814 drug Substances 0.000 claims abstract description 21
- 238000011282 treatment Methods 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 234
- -1 -OH Chemical group 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- OJEOJUQOECNDND-UHFFFAOYSA-N oxetan-3-amine Chemical compound NC1COC1 OJEOJUQOECNDND-UHFFFAOYSA-N 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 208000000094 Chronic Pain Diseases 0.000 claims description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000011200 topical administration Methods 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- VCHWGGQXHIBEEA-VIFPVBQESA-N 3-[(1r)-1-[5-[4-(trifluoromethoxy)phenyl]-1h-imidazol-2-yl]ethyl]oxetan-3-amine Chemical compound C=1NC([C@H](C)C2(N)COC2)=NC=1C1=CC=C(OC(F)(F)F)C=C1 VCHWGGQXHIBEEA-VIFPVBQESA-N 0.000 claims 1
- ONVPCYBBFGHZSZ-LBPRGKRZSA-N 3-[(1r)-1-[5-[4-(trifluoromethoxy)phenyl]-1h-imidazol-2-yl]propyl]oxetan-3-amine Chemical compound C=1NC([C@H](CC)C2(N)COC2)=NC=1C1=CC=C(OC(F)(F)F)C=C1 ONVPCYBBFGHZSZ-LBPRGKRZSA-N 0.000 claims 1
- WEAFAWYVJKPGDN-VIFPVBQESA-N 3-[(1r)-1-[5-[4-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]ethyl]oxetan-3-amine Chemical compound C=1NC([C@H](C)C2(N)COC2)=NC=1C1=CC=C(C(F)(F)F)C=C1 WEAFAWYVJKPGDN-VIFPVBQESA-N 0.000 claims 1
- VCHWGGQXHIBEEA-SECBINFHSA-N 3-[(1s)-1-[5-[4-(trifluoromethoxy)phenyl]-1h-imidazol-2-yl]ethyl]oxetan-3-amine Chemical compound C=1NC([C@@H](C)C2(N)COC2)=NC=1C1=CC=C(OC(F)(F)F)C=C1 VCHWGGQXHIBEEA-SECBINFHSA-N 0.000 claims 1
- WEAFAWYVJKPGDN-SECBINFHSA-N 3-[(1s)-1-[5-[4-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]ethyl]oxetan-3-amine Chemical compound C=1NC([C@@H](C)C2(N)COC2)=NC=1C1=CC=C(C(F)(F)F)C=C1 WEAFAWYVJKPGDN-SECBINFHSA-N 0.000 claims 1
- VCHWGGQXHIBEEA-UHFFFAOYSA-N 3-[1-[5-[4-(trifluoromethoxy)phenyl]-1h-imidazol-2-yl]ethyl]oxetan-3-amine Chemical compound C1OCC1(N)C(C)C(NC=1)=NC=1C1=CC=C(OC(F)(F)F)C=C1 VCHWGGQXHIBEEA-UHFFFAOYSA-N 0.000 claims 1
- ONVPCYBBFGHZSZ-UHFFFAOYSA-N 3-[1-[5-[4-(trifluoromethoxy)phenyl]-1h-imidazol-2-yl]propyl]oxetan-3-amine Chemical compound C1OCC1(N)C(CC)C(NC=1)=NC=1C1=CC=C(OC(F)(F)F)C=C1 ONVPCYBBFGHZSZ-UHFFFAOYSA-N 0.000 claims 1
- WEAFAWYVJKPGDN-UHFFFAOYSA-N 3-[1-[5-[4-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]ethyl]oxetan-3-amine Chemical compound C1OCC1(N)C(C)C(NC=1)=NC=1C1=CC=C(C(F)(F)F)C=C1 WEAFAWYVJKPGDN-UHFFFAOYSA-N 0.000 claims 1
- KOFTYPLPHYCLEM-UHFFFAOYSA-N 3-[[5-(4-chloro-3-methylphenyl)-1h-imidazol-2-yl]methyl]oxetan-3-amine Chemical compound C1=C(Cl)C(C)=CC(C=2N=C(CC3(N)COC3)NC=2)=C1 KOFTYPLPHYCLEM-UHFFFAOYSA-N 0.000 claims 1
- HIPVLIIHJJHFJK-UHFFFAOYSA-N 3-[[5-[4-(difluoromethoxy)phenyl]-1h-imidazol-2-yl]methyl]oxetan-3-amine Chemical compound N=1C(C=2C=CC(OC(F)F)=CC=2)=CNC=1CC1(N)COC1 HIPVLIIHJJHFJK-UHFFFAOYSA-N 0.000 claims 1
- ARCAJTAMUQLDKI-UHFFFAOYSA-N 3-[[5-[4-(trifluoromethoxy)phenyl]-1h-imidazol-2-yl]methyl]oxan-3-amine Chemical compound N=1C(C=2C=CC(OC(F)(F)F)=CC=2)=CNC=1CC1(N)CCCOC1 ARCAJTAMUQLDKI-UHFFFAOYSA-N 0.000 claims 1
- QMSYRAZMYGWQJB-UHFFFAOYSA-N 3-[[5-[4-(trifluoromethoxy)phenyl]-1h-imidazol-2-yl]methyl]oxetan-3-amine Chemical compound N=1C(C=2C=CC(OC(F)(F)F)=CC=2)=CNC=1CC1(N)COC1 QMSYRAZMYGWQJB-UHFFFAOYSA-N 0.000 claims 1
- JBKQPDYDZFNNCB-UHFFFAOYSA-N 3-[[5-[4-(trifluoromethoxy)phenyl]-1h-imidazol-2-yl]methyl]oxolan-3-amine Chemical compound N=1C(C=2C=CC(OC(F)(F)F)=CC=2)=CNC=1CC1(N)CCOC1 JBKQPDYDZFNNCB-UHFFFAOYSA-N 0.000 claims 1
- FBZXNMLGHZYHND-UHFFFAOYSA-N 3-[[5-[4-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]methyl]oxetan-3-amine Chemical compound N=1C(C=2C=CC(=CC=2)C(F)(F)F)=CNC=1CC1(N)COC1 FBZXNMLGHZYHND-UHFFFAOYSA-N 0.000 claims 1
- AMAJNGRPSHOPRB-UHFFFAOYSA-N 4-[[5-[4-(trifluoromethoxy)phenyl]-1h-imidazol-2-yl]methyl]oxan-4-amine Chemical compound N=1C(C=2C=CC(OC(F)(F)F)=CC=2)=CNC=1CC1(N)CCOCC1 AMAJNGRPSHOPRB-UHFFFAOYSA-N 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 116
- 238000000034 method Methods 0.000 abstract description 108
- 101000654356 Homo sapiens Sodium channel protein type 10 subunit alpha Proteins 0.000 abstract description 35
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- 230000008569 process Effects 0.000 abstract description 16
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- 150000002460 imidazoles Chemical class 0.000 abstract description 11
- 239000000543 intermediate Substances 0.000 abstract description 11
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 abstract description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
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- 238000006243 chemical reaction Methods 0.000 description 69
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161551628P | 2011-10-26 | 2011-10-26 | |
| US61/551,628 | 2011-10-26 | ||
| PCT/IB2012/055610 WO2013061205A2 (en) | 2011-10-26 | 2012-10-15 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2850925A1 CA2850925A1 (en) | 2013-05-02 |
| CA2850925C true CA2850925C (en) | 2017-01-10 |
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2012
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- 2012-10-15 EA EA201490864A patent/EA023375B1/ru not_active IP Right Cessation
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- 2012-10-15 EP EP12794777.8A patent/EP2771335A2/en not_active Withdrawn
- 2012-10-15 AU AU2012328034A patent/AU2012328034B2/en not_active Ceased
- 2012-10-15 BR BR112014009102A patent/BR112014009102A2/pt active Search and Examination
- 2012-10-15 UA UAA201404440A patent/UA109220C2/uk unknown
- 2012-10-15 CN CN201280052591.6A patent/CN103906746B/zh not_active Expired - Fee Related
- 2012-10-15 US US14/351,893 patent/US9079878B2/en not_active Expired - Fee Related
- 2012-10-15 WO PCT/IB2012/055610 patent/WO2013061205A2/en not_active Ceased
- 2012-10-15 KR KR1020147010826A patent/KR101586966B1/ko not_active Expired - Fee Related
- 2012-10-15 SG SG11201401032YA patent/SG11201401032YA/en unknown
- 2012-10-15 CA CA2850925A patent/CA2850925C/en not_active Expired - Fee Related
- 2012-10-15 PE PE2014000605A patent/PE20141682A1/es not_active Application Discontinuation
- 2012-10-15 MD MDA20140037A patent/MD20140037A2/ro not_active Application Discontinuation
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- 2014-03-27 ZA ZA2014/02281A patent/ZA201402281B/en unknown
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