TW201609691A - 氟甲基取代之吡咯羧醯胺之二 - Google Patents
氟甲基取代之吡咯羧醯胺之二 Download PDFInfo
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- TW201609691A TW201609691A TW103144423A TW103144423A TW201609691A TW 201609691 A TW201609691 A TW 201609691A TW 103144423 A TW103144423 A TW 103144423A TW 103144423 A TW103144423 A TW 103144423A TW 201609691 A TW201609691 A TW 201609691A
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- Prior art keywords
- alkyl
- group
- trifluoromethyl
- benzyl
- dimethyl
- Prior art date
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- -1 Fluoromethyl-substituted pyrrole carboxamides Chemical class 0.000 title claims description 282
- 150000001875 compounds Chemical class 0.000 claims abstract description 108
- 208000002193 Pain Diseases 0.000 claims abstract description 88
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 51
- 238000011282 treatment Methods 0.000 claims abstract description 26
- 208000035475 disorder Diseases 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
- 125000001424 substituent group Chemical group 0.000 claims description 135
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 85
- 229910052799 carbon Inorganic materials 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 65
- 125000001072 heteroaryl group Chemical group 0.000 claims description 56
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 53
- 125000000623 heterocyclic group Chemical group 0.000 claims description 52
- 239000000126 substance Substances 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 41
- 125000005842 heteroatom Chemical group 0.000 claims description 37
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 18
- 230000002265 prevention Effects 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 208000000094 Chronic Pain Diseases 0.000 claims description 15
- 206010019233 Headaches Diseases 0.000 claims description 15
- 231100000869 headache Toxicity 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 206010065390 Inflammatory pain Diseases 0.000 claims description 14
- 208000005298 acute pain Diseases 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 14
- 208000009935 visceral pain Diseases 0.000 claims description 14
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- 230000004770 neurodegeneration Effects 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002971 oxazolyl group Chemical group 0.000 claims description 10
- 125000000335 thiazolyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 239000012453 solvate Substances 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
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 201000000980 schizophrenia Diseases 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-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
- IZPBSCOLEPSWMK-UHFFFAOYSA-N [1-benzyl-3-(2-methoxypyrimidin-5-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)C=1C=NC(=NC1)OC)C(=O)N1CCOCC1 IZPBSCOLEPSWMK-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- DNWDTTAYJAOYOG-UHFFFAOYSA-N [1-benzyl-4-methyl-3-pyrimidin-5-yl-5-(trifluoromethyl)pyrrol-2-yl]-morpholin-4-ylmethanone Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C=1C=NC=NC1)C(=O)N1CCOCC1 DNWDTTAYJAOYOG-UHFFFAOYSA-N 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 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 4
- FQGNCMINDWWCHY-UHFFFAOYSA-N [1-benzyl-3-(5-chloropyrimidin-2-yl)-4-methyl-5-(trifluoromethyl)pyrrol-2-yl]-(2,2-dimethylmorpholin-4-yl)methanone Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NC=C(C=N1)Cl)C(=O)N1CC(OCC1)(C)C FQGNCMINDWWCHY-UHFFFAOYSA-N 0.000 claims description 4
- FJGMWFCFOBKOBB-UHFFFAOYSA-N [1-benzyl-3-(5-fluoropyridin-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=C1)F)C(=O)N1CCOCC1 FJGMWFCFOBKOBB-UHFFFAOYSA-N 0.000 claims description 4
- MRFQSTRKVVEFEL-UHFFFAOYSA-N [1-benzyl-3-(5-fluoropyrimidin-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=N1)F)C(=O)N1CCOCC1 MRFQSTRKVVEFEL-UHFFFAOYSA-N 0.000 claims description 4
- IPVGMYQLMCXWMD-UHFFFAOYSA-N [1-benzyl-3-(6-methoxy-4-methylpyridin-3-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)C=1C=NC(=CC1C)OC)C(=O)N1CCOCC1 IPVGMYQLMCXWMD-UHFFFAOYSA-N 0.000 claims description 4
- FFEWMQKOSIHYGC-UHFFFAOYSA-N [1-benzyl-4-methyl-3-pyrazin-2-yl-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=CN=C1)C(=O)N1CCOCC1 FFEWMQKOSIHYGC-UHFFFAOYSA-N 0.000 claims description 4
- BLPNLIICUSCLSZ-UHFFFAOYSA-N [1-benzyl-4-methyl-3-pyridazin-4-yl-5-(trifluoromethyl)pyrrol-2-yl]-morpholin-4-ylmethanone Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=CN=NC=C1)C(=O)N1CCOCC1 BLPNLIICUSCLSZ-UHFFFAOYSA-N 0.000 claims description 4
- KVGCOAUYRVZHJB-UHFFFAOYSA-N [1-benzyl-4-methyl-3-pyrimidin-2-yl-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=CC=N1)C(=O)N1CCOCC1 KVGCOAUYRVZHJB-UHFFFAOYSA-N 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
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- KUMCDNRWDGNMJY-UHFFFAOYSA-N 1-benzyl-N,4-dimethyl-3-(1-methylimidazol-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)C=1N(C=CN1)C)C(=O)N(C)C(C)C KUMCDNRWDGNMJY-UHFFFAOYSA-N 0.000 claims description 3
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 3
- PFUOFQZBSBRGSK-UHFFFAOYSA-N [1-benzyl-3-(3,5-dimethyl-1,2-oxazol-4-yl)-4-methyl-5-(trifluoromethyl)pyrrol-2-yl]-morpholin-4-ylmethanone Chemical compound CC1=NOC(C)=C1C1=C(C(=O)N2CCOCC2)N(CC=2C=CC=CC=2)C(C(F)(F)F)=C1C PFUOFQZBSBRGSK-UHFFFAOYSA-N 0.000 claims description 3
- RHJAQQOPSKUIRQ-UHFFFAOYSA-N [1-benzyl-3-(5-methoxypyrazin-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(N=C1)OC)C(=O)N1CCOCC1 RHJAQQOPSKUIRQ-UHFFFAOYSA-N 0.000 claims description 3
- UJEHAUXOCZMSEW-UHFFFAOYSA-N [1-benzyl-3-(6-chloropyridazin-3-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)C=1N=NC(=CC1)Cl)C(=O)N1CCOCC1 UJEHAUXOCZMSEW-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
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
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- 208000006011 Stroke Diseases 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
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- XORMLNFMYJOPMK-UHFFFAOYSA-N [1-benzyl-3-(5-chloropyridin-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=C1)Cl)C(=O)N1CCOCC1 XORMLNFMYJOPMK-UHFFFAOYSA-N 0.000 claims 2
- VQVHBCJEAPEWGY-UHFFFAOYSA-N [1-benzyl-3-(5-chloropyrimidin-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=N1)Cl)C(=O)N1CCOCC1 VQVHBCJEAPEWGY-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract description 26
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- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical group NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 abstract description 2
- 238000011321 prophylaxis Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 199
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- 239000011541 reaction mixture Substances 0.000 description 84
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- 239000011734 sodium Substances 0.000 description 52
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- 239000012044 organic layer Substances 0.000 description 44
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- 210000004027 cell Anatomy 0.000 description 19
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 18
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
- 108091006146 Channels Proteins 0.000 description 17
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- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13005933 | 2013-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201609691A true TW201609691A (zh) | 2016-03-16 |
Family
ID=49882759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW103144423A TW201609691A (zh) | 2013-12-19 | 2014-12-19 | 氟甲基取代之吡咯羧醯胺之二 |
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 |
|---|---|---|---|---|
| JP2016540823A (ja) | 2013-12-19 | 2016-12-28 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | フルオロ置換ピロールカルボキサミドiv |
| AU2014365744A1 (en) * | 2013-12-19 | 2016-05-26 | Grunenthal Gmbh | Fluoromethyl-substituted pyrrole carboxamides III |
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 |
| JP5815029B2 (ja) * | 2010-07-09 | 2015-11-17 | クオンベルゲンセ プハルマセウトイカルス リミテッド | カルシウムチャネル遮断薬としてのテトラゾール化合物 |
| CN103842357A (zh) * | 2011-07-26 | 2014-06-04 | 格吕伦塔尔有限公司 | 作为类香草素受体配体的被取代的、含有杂芳环吡唑的羧酰胺和脲衍生物 |
| TW201416348A (zh) * | 2012-08-29 | 2014-05-01 | Gruenenthal Chemie | 以氟甲基取代之吡咯甲醯胺 |
| JP2016540823A (ja) | 2013-12-19 | 2016-12-28 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | フルオロ置換ピロールカルボキサミドiv |
| AU2014365744A1 (en) | 2013-12-19 | 2016-05-26 | Grunenthal Gmbh | Fluoromethyl-substituted pyrrole carboxamides III |
-
2014
- 2014-12-18 CA CA2934327A patent/CA2934327A1/en not_active Abandoned
- 2014-12-18 WO PCT/EP2014/003430 patent/WO2015090600A1/en not_active Ceased
- 2014-12-18 JP JP2016541134A patent/JP2016540820A/ja active Pending
- 2014-12-18 AU AU2014365741A patent/AU2014365741A1/en not_active Abandoned
- 2014-12-18 MX MX2016007956A patent/MX2016007956A/es unknown
- 2014-12-18 EP EP14821512.2A patent/EP3083612A1/en not_active Withdrawn
- 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 |
|---|---|
| EP3083612A1 (en) | 2016-10-26 |
| WO2015090600A1 (en) | 2015-06-25 |
| JP2016540820A (ja) | 2016-12-28 |
| CA2934327A1 (en) | 2015-06-25 |
| US20160289214A1 (en) | 2016-10-06 |
| AR098845A1 (es) | 2016-06-15 |
| AU2014365741A1 (en) | 2016-05-26 |
| MX2016007956A (es) | 2016-09-09 |
| US9562036B2 (en) | 2017-02-07 |
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