AU2014365741A1 - Fluoromethyl-substituted pyrrole carboxamides as CaV2.2 calcium channel blockers - Google Patents
Fluoromethyl-substituted pyrrole carboxamides as CaV2.2 calcium channel blockers Download PDFInfo
- Publication number
- AU2014365741A1 AU2014365741A1 AU2014365741A AU2014365741A AU2014365741A1 AU 2014365741 A1 AU2014365741 A1 AU 2014365741A1 AU 2014365741 A AU2014365741 A AU 2014365741A AU 2014365741 A AU2014365741 A AU 2014365741A AU 2014365741 A1 AU2014365741 A1 AU 2014365741A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- methyl
- benzyl
- trifluoromethyl
- pyrrole
- 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
- -1 Fluoromethyl-substituted pyrrole carboxamides Chemical class 0.000 title claims description 263
- 229940127291 Calcium channel antagonist Drugs 0.000 title abstract description 4
- 239000000480 calcium channel blocker Substances 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- 208000002193 Pain Diseases 0.000 claims abstract description 100
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 41
- 238000011282 treatment Methods 0.000 claims abstract description 26
- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical group NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 claims abstract description 23
- 208000035475 disorder Diseases 0.000 claims abstract description 21
- 238000011321 prophylaxis Methods 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 118
- 125000000623 heterocyclic group Chemical group 0.000 claims description 105
- 125000001424 substituent group Chemical group 0.000 claims description 105
- 229910052731 fluorine Inorganic materials 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 125000001072 heteroaryl group Chemical group 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 43
- 229910052799 carbon Inorganic materials 0.000 claims description 37
- 125000005842 heteroatom Chemical group 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 208000000094 Chronic Pain Diseases 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 206010019233 Headaches Diseases 0.000 claims description 14
- 206010065390 Inflammatory pain Diseases 0.000 claims description 14
- 208000005298 acute pain Diseases 0.000 claims description 14
- 231100000869 headache Toxicity 0.000 claims description 14
- 208000009935 visceral pain Diseases 0.000 claims description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 208000019022 Mood disease Diseases 0.000 claims description 10
- 206010015037 epilepsy Diseases 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000002971 oxazolyl group Chemical group 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 125000000335 thiazolyl group Chemical group 0.000 claims description 10
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 claims description 8
- 201000000980 schizophrenia Diseases 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- CWNUAXVTSZEDEA-UHFFFAOYSA-N 1-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound NC(=O)C1=CC=CN1C(F)(F)F CWNUAXVTSZEDEA-UHFFFAOYSA-N 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- BJQICQNQDVXHKB-UHFFFAOYSA-N 1-benzyl-3-(3,5-dimethyl-1,2-oxazol-4-yl)-N-(2,2-dimethylpropyl)-N,4-dimethyl-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C=1C(=NOC1C)C)C(=O)N(C)CC(C)(C)C BJQICQNQDVXHKB-UHFFFAOYSA-N 0.000 claims description 4
- BYZAOFKDUTVYCJ-UHFFFAOYSA-N 1-benzyl-3-(5-chloropyrimidin-2-yl)-N-[2,2-dimethyl-3-(methylamino)-3-oxopropyl]-N,4-dimethyl-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NC=C(C=N1)Cl)C(=O)N(CC(C)(C(NC)=O)C)C BYZAOFKDUTVYCJ-UHFFFAOYSA-N 0.000 claims description 4
- KMAGTEYCXRNREN-UHFFFAOYSA-N CC=1C(=C(NC1C(F)(F)F)C(=O)N)C Chemical compound CC=1C(=C(NC1C(F)(F)F)C(=O)N)C KMAGTEYCXRNREN-UHFFFAOYSA-N 0.000 claims description 4
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- IKRDSBJAKWZUQS-UHFFFAOYSA-N 5-[1-benzyl-4-methyl-2-(morpholine-4-carbonyl)-5-(trifluoromethyl)pyrrol-3-yl]-4-methylpyridine-2-carbonitrile Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C=1C(=CC(=NC1)C#N)C)C(=O)N1CCOCC1 IKRDSBJAKWZUQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- QLWOFWHIBSEYDN-UHFFFAOYSA-N 1-benzyl-3-(5-chloro-3-methylsulfinylpyridin-2-yl)-N,4-dimethyl-N-propan-2-yl-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NC=C(C=C1S(=O)C)Cl)C(=O)N(C)C(C)C QLWOFWHIBSEYDN-UHFFFAOYSA-N 0.000 claims description 2
- VESUZQYSCSZQLQ-UHFFFAOYSA-N 1-benzyl-3-(5-cyclopropylpyrazin-2-yl)-N,4-dimethyl-N-propan-2-yl-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NC=C(N=C1)C1CC1)C(=O)N(C)C(C)C VESUZQYSCSZQLQ-UHFFFAOYSA-N 0.000 claims description 2
- OJKRPFXFNXFKOT-UHFFFAOYSA-N 1-benzyl-3-(5-cyclopropylpyrimidin-2-yl)-N,4-dimethyl-N-propan-2-yl-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NC=C(C=N1)C1CC1)C(=O)N(C)C(C)C OJKRPFXFNXFKOT-UHFFFAOYSA-N 0.000 claims description 2
- FFUHUOINMUFWCZ-UHFFFAOYSA-N 1-benzyl-3-(6-cyano-4-methylpyridin-3-yl)-N-(2,2-dimethylpropyl)-N,4-dimethyl-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C=1C=NC(=CC1C)C#N)C(=O)N(CC(C)(C)C)C FFUHUOINMUFWCZ-UHFFFAOYSA-N 0.000 claims description 2
- ISMLVSABQSQVDO-UHFFFAOYSA-N 1-benzyl-N,4-dimethyl-3-(1-methylpyrazol-3-yl)-N-propan-2-yl-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NN(C=C1)C)C(=O)N(C)C(C)C ISMLVSABQSQVDO-UHFFFAOYSA-N 0.000 claims description 2
- MYYZMVYCACIHKX-UHFFFAOYSA-N 1-benzyl-N,4-dimethyl-3-(5-methylsulfinylpyridin-2-yl)-N-propan-2-yl-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NC=C(C=C1)S(=O)C)C(=O)N(C)C(C)C MYYZMVYCACIHKX-UHFFFAOYSA-N 0.000 claims description 2
- IMXUEBQMABCOQO-UHFFFAOYSA-N [1-benzyl-3-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]-4-methyl-5-(trifluoromethyl)pyrrol-2-yl]-morpholin-4-ylmethanone Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NC=C(C=C1F)C(F)(F)F)C(=O)N1CCOCC1 IMXUEBQMABCOQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 claims 3
- LVMSDWHDUVWPLS-UHFFFAOYSA-N 1-benzyl-3-(5-chloropyridin-2-yl)-4-methyl-N-propan-2-yl-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NC=C(C=C1)Cl)C(=O)NC(C)C LVMSDWHDUVWPLS-UHFFFAOYSA-N 0.000 claims 1
- SHMUAVGHCHPHHT-UHFFFAOYSA-N 1-benzyl-3-(5-chloropyrimidin-2-yl)-4-methyl-N-propan-2-yl-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NC=C(C=N1)Cl)C(=O)NC(C)C SHMUAVGHCHPHHT-UHFFFAOYSA-N 0.000 claims 1
- FVJSWVQGOYEBNB-UHFFFAOYSA-N 1-benzyl-3-(5-chloropyrimidin-2-yl)-N,4-dimethyl-N-propan-2-yl-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NC=C(C=N1)Cl)C(=O)N(C)C(C)C FVJSWVQGOYEBNB-UHFFFAOYSA-N 0.000 claims 1
- JFDHRYQSSBSFCB-UHFFFAOYSA-N 1-benzyl-N-(2,2-dimethylpropyl)-3-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]-N,4-dimethyl-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NC=C(C=C1F)C(F)(F)F)C(=O)N(C)CC(C)(C)C JFDHRYQSSBSFCB-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
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- 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
- A61P25/28—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]
-
- 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]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D417/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13005933 | 2013-12-19 | ||
| EP13005933.0 | 2013-12-19 | ||
| PCT/EP2014/003430 WO2015090600A1 (en) | 2013-12-19 | 2014-12-18 | Fluoromethyl-substituted pyrrole carboxamides as cav2.2 calcium channel blockers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2014365741A1 true AU2014365741A1 (en) | 2016-05-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2014365741A Abandoned AU2014365741A1 (en) | 2013-12-19 | 2014-12-18 | Fluoromethyl-substituted pyrrole carboxamides as CaV2.2 calcium channel blockers |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9562036B2 (enExample) |
| EP (1) | EP3083612A1 (enExample) |
| JP (1) | JP2016540820A (enExample) |
| AR (1) | AR098845A1 (enExample) |
| AU (1) | AU2014365741A1 (enExample) |
| CA (1) | CA2934327A1 (enExample) |
| MX (1) | MX2016007956A (enExample) |
| TW (1) | TW201609691A (enExample) |
| WO (1) | WO2015090600A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2934324A1 (en) * | 2013-12-19 | 2015-06-25 | Grunenthal Gmbh | Fluoromethyl-substituted pyrrole carboxamides iii |
| WO2015090599A1 (en) | 2013-12-19 | 2015-06-25 | Grünenthal GmbH | Fluoromethyl-substituted pyrrole carboxamides iv |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4477463A (en) * | 1982-05-10 | 1984-10-16 | E. I. Du Pont De Nemours And Company | Antiinflammatory and/or analgesic 1-alkyl-4,5-diaryl-2-fluoroalkyl-1H-pyrroles |
| DE102006027229A1 (de) * | 2006-06-09 | 2007-12-20 | Grünenthal GmbH | 1,3-Disubstituierte 4-Methyl-1H-pyrrol-2-carbonsäureamide und ihre Verwendung zur Herstellung von Arzneimitteln |
| WO2012004604A1 (en) * | 2010-07-09 | 2012-01-12 | Convergence Pharmaceuticals Limited | Tetrazole compounds as calcium channel blockers |
| KR20140049026A (ko) * | 2011-07-26 | 2014-04-24 | 그뤼넨탈 게엠베하 | 바닐로이드 수용체 리간드로서의 치환된 헤테로방향족 피라졸―함유 카복스아미드 및 우레아 유도체 |
| TW201416348A (zh) * | 2012-08-29 | 2014-05-01 | Gruenenthal Chemie | 以氟甲基取代之吡咯甲醯胺 |
| CA2934324A1 (en) | 2013-12-19 | 2015-06-25 | Grunenthal Gmbh | Fluoromethyl-substituted pyrrole carboxamides iii |
| WO2015090599A1 (en) | 2013-12-19 | 2015-06-25 | Grünenthal GmbH | Fluoromethyl-substituted pyrrole carboxamides iv |
-
2014
- 2014-12-18 JP JP2016541134A patent/JP2016540820A/ja active Pending
- 2014-12-18 AU AU2014365741A patent/AU2014365741A1/en not_active Abandoned
- 2014-12-18 EP EP14821512.2A patent/EP3083612A1/en not_active Withdrawn
- 2014-12-18 CA CA2934327A patent/CA2934327A1/en not_active Abandoned
- 2014-12-18 MX MX2016007956A patent/MX2016007956A/es unknown
- 2014-12-18 WO PCT/EP2014/003430 patent/WO2015090600A1/en not_active Ceased
- 2014-12-19 AR ARP140104776A patent/AR098845A1/es unknown
- 2014-12-19 TW TW103144423A patent/TW201609691A/zh unknown
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2016
- 2016-06-17 US US15/185,124 patent/US9562036B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US9562036B2 (en) | 2017-02-07 |
| US20160289214A1 (en) | 2016-10-06 |
| EP3083612A1 (en) | 2016-10-26 |
| CA2934327A1 (en) | 2015-06-25 |
| AR098845A1 (es) | 2016-06-15 |
| TW201609691A (zh) | 2016-03-16 |
| MX2016007956A (es) | 2016-09-09 |
| JP2016540820A (ja) | 2016-12-28 |
| WO2015090600A1 (en) | 2015-06-25 |
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