JP2007509985A5 - - Google Patents
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- JP2007509985A5 JP2007509985A5 JP2006538401A JP2006538401A JP2007509985A5 JP 2007509985 A5 JP2007509985 A5 JP 2007509985A5 JP 2006538401 A JP2006538401 A JP 2006538401A JP 2006538401 A JP2006538401 A JP 2006538401A JP 2007509985 A5 JP2007509985 A5 JP 2007509985A5
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- JP
- Japan
- Prior art keywords
- amine
- compound
- trifluoromethyl
- alkyl
- salt
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 47
- -1 amino, aminocarbonyl Chemical group 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 34
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical group 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
- 208000002193 Pain Diseases 0.000 claims 11
- 108010062740 TRPV Cation Channels Proteins 0.000 claims 11
- 102000011040 TRPV Cation Channels Human genes 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 150000002431 hydrogen Chemical group 0.000 claims 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 6
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 230000004044 response Effects 0.000 claims 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 206010061218 Inflammation Diseases 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 150000005215 alkyl ethers Chemical class 0.000 claims 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 230000004054 inflammatory process Effects 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 208000004296 neuralgia Diseases 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 3
- 229910052791 calcium Inorganic materials 0.000 claims 3
- 239000011575 calcium Substances 0.000 claims 3
- 229960002504 capsaicin Drugs 0.000 claims 3
- 235000017663 capsaicin Nutrition 0.000 claims 3
- 210000004027 cell Anatomy 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 208000033808 peripheral neuropathy Diseases 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010029240 Neuritis Diseases 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 230000005540 biological transmission Effects 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- CKQXIFCAJCCLIX-UHFFFAOYSA-N 1,6-naphthyridine-4-carboxylic acid Chemical compound C1=NC=C2C(C(=O)O)=CC=NC2=C1 CKQXIFCAJCCLIX-UHFFFAOYSA-N 0.000 claims 1
- ZQGIIWRWGYVTDD-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-[(2-ethoxynaphthalen-1-yl)methyl]-n-[(1-ethylbenzimidazol-2-yl)methyl]methanamine Chemical compound CCOC1=CC=C2C=CC=CC2=C1CN(CC=1N(C2=CC=CC=C2N=1)CC)CC1=CC=C(Cl)C=C1Cl ZQGIIWRWGYVTDD-UHFFFAOYSA-N 0.000 claims 1
- LGHGTYLPJGWRAG-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-[(2-ethoxynaphthalen-1-yl)methyl]-n-[(1-pentylbenzimidazol-2-yl)methyl]methanamine Chemical compound N=1C2=CC=CC=C2N(CCCCC)C=1CN(CC=1C2=CC=CC=C2C=CC=1OCC)CC1=CC=C(Cl)C=C1Cl LGHGTYLPJGWRAG-UHFFFAOYSA-N 0.000 claims 1
- UPVCTFCMCJTAJN-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-[(2-ethoxynaphthalen-1-yl)methyl]-n-[(5-fluoro-1-propylbenzimidazol-2-yl)methyl]methanamine Chemical compound N=1C2=CC(F)=CC=C2N(CCC)C=1CN(CC=1C2=CC=CC=C2C=CC=1OCC)CC1=CC=C(Cl)C=C1Cl UPVCTFCMCJTAJN-UHFFFAOYSA-N 0.000 claims 1
- SOIVVERMMKARJC-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-n-[(2-ethoxynaphthalen-1-yl)methyl]-n-[(6-fluoro-1-propylbenzimidazol-2-yl)methyl]methanamine Chemical compound N=1C2=CC=C(F)C=C2N(CCC)C=1CN(CC=1C2=CC=CC=C2C=CC=1OCC)CC1=CC=C(Cl)C=C1Cl SOIVVERMMKARJC-UHFFFAOYSA-N 0.000 claims 1
- HDNAOVUZXFNSCZ-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-[(3-methoxyphenyl)methyl]-1,6-naphthyridine-4-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2C3=CN=CC=C3N=C(C=2)C=2C=C(Cl)C=CC=2)=C1 HDNAOVUZXFNSCZ-UHFFFAOYSA-N 0.000 claims 1
- VSZAVNCUXDQZQE-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-[(3-methoxyphenyl)methyl]pyridine-4-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2C=C(N=CC=2)C=2C=C(Cl)C=CC=2)=C1 VSZAVNCUXDQZQE-UHFFFAOYSA-N 0.000 claims 1
- YSOHFFXSRTZDBS-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-[[3-(difluoromethoxy)phenyl]methyl]-1,6-naphthyridine-4-carboxamide Chemical compound FC(F)OC1=CC=CC(CNC(=O)C=2C3=CN=CC=C3N=C(C=2)C=2C=C(Cl)C=CC=2)=C1 YSOHFFXSRTZDBS-UHFFFAOYSA-N 0.000 claims 1
- HNOOCWMFLUSLIP-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-[[3-(trifluoromethyl)phenyl]methyl]-1,6-naphthyridine-4-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)C=2C3=CN=CC=C3N=C(C=2)C=2C=C(Cl)C=CC=2)=C1 HNOOCWMFLUSLIP-UHFFFAOYSA-N 0.000 claims 1
- VTODTQZUBPVDJW-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[(3-methoxyphenyl)methyl]-1,6-naphthyridine-4-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2C3=CN=CC=C3N=C(C=2)C=2C=CC(Cl)=CC=2)=C1 VTODTQZUBPVDJW-UHFFFAOYSA-N 0.000 claims 1
- LNCUARNQAVSXEO-UHFFFAOYSA-N 2-(trifluoromethyl)-n-[7-(trifluoromethyl)-1,8-naphthyridin-4-yl]-1,3-thiazol-5-amine Chemical compound S1C(C(F)(F)F)=NC=C1NC1=CC=NC2=NC(C(F)(F)F)=CC=C12 LNCUARNQAVSXEO-UHFFFAOYSA-N 0.000 claims 1
- TWWBMWBPAJAFEF-UHFFFAOYSA-N 2-[(2,6-dimethylmorpholin-4-yl)methyl]-7-fluoro-n-[5-(trifluoromethyl)thiophen-2-yl]quinazolin-4-amine Chemical compound C1C(C)OC(C)CN1CC1=NC(NC=2SC(=CC=2)C(F)(F)F)=C(C=CC(F)=C2)C2=N1 TWWBMWBPAJAFEF-UHFFFAOYSA-N 0.000 claims 1
- LUFFFDDTPAINSO-UHFFFAOYSA-N 2-[2-fluoro-5-(trifluoromethyl)phenyl]-n-[(3-methoxyphenyl)methyl]-1,6-naphthyridine-4-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2C3=CN=CC=C3N=C(C=2)C=2C(=CC=C(C=2)C(F)(F)F)F)=C1 LUFFFDDTPAINSO-UHFFFAOYSA-N 0.000 claims 1
- VPROKSPKSKMAFC-OKILXGFUSA-N 2-[[(2s,6r)-2,6-dimethylmorpholin-4-yl]methyl]-7-(trifluoromethyl)-n-[4-(trifluoromethyl)phenyl]quinazolin-4-amine Chemical compound C1[C@@H](C)O[C@@H](C)CN1CC1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=C(C=CC(=C2)C(F)(F)F)C2=N1 VPROKSPKSKMAFC-OKILXGFUSA-N 0.000 claims 1
- QDHMHDKQNHLHHW-BETUJISGSA-N 2-[[(2s,6r)-2,6-dimethylmorpholin-4-yl]methyl]-7-(trifluoromethyl)-n-[6-(trifluoromethyl)pyridin-3-yl]quinazolin-4-amine Chemical compound C1[C@@H](C)O[C@@H](C)CN1CC1=NC(NC=2C=NC(=CC=2)C(F)(F)F)=C(C=CC(=C2)C(F)(F)F)C2=N1 QDHMHDKQNHLHHW-BETUJISGSA-N 0.000 claims 1
- RTEDXCPJCCALRX-UHFFFAOYSA-N 3-(7-bromopyrido[3,2-d]pyrimidin-4-yl)-4-tert-butyl-1,2-oxazole Chemical compound BrC1=CC=2N=CN=C(C=2N=C1)C1=NOC=C1C(C)(C)C RTEDXCPJCCALRX-UHFFFAOYSA-N 0.000 claims 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- UXUPRWYQSYWRIU-UHFFFAOYSA-N 5-(trifluoromethyl)-n-[7-(trifluoromethyl)quinazolin-4-yl]-1,2-thiazol-3-amine Chemical compound S1C(C(F)(F)F)=CC(NC=2C3=CC=C(C=C3N=CN=2)C(F)(F)F)=N1 UXUPRWYQSYWRIU-UHFFFAOYSA-N 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- QKNMVKKNDPUTBZ-UHFFFAOYSA-N 6-iodo-n-[4-(trifluoromethyl)phenyl]quinazolin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC=NC2=CC=C(I)C=C12 QKNMVKKNDPUTBZ-UHFFFAOYSA-N 0.000 claims 1
- KRUIIAIQWJJSDN-UHFFFAOYSA-N 7-(trifluoromethyl)-n-[4-(trifluoromethyl)phenyl]quinazolin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC=NC2=CC(C(F)(F)F)=CC=C12 KRUIIAIQWJJSDN-UHFFFAOYSA-N 0.000 claims 1
- GUZQYQMDVHTURG-UHFFFAOYSA-N 7-bromo-n-(3-methyl-4-propan-2-ylphenyl)pyrido[3,2-d]pyrimidin-4-amine Chemical compound C1=C(C)C(C(C)C)=CC=C1NC1=NC=NC2=CC(Br)=CN=C12 GUZQYQMDVHTURG-UHFFFAOYSA-N 0.000 claims 1
- FBXDMGNGVJSIEW-CALCHBBNSA-N 7-bromo-n-(4-tert-butylphenyl)-2-[[(2r,6s)-2,6-dimethylmorpholin-4-yl]methyl]quinazolin-4-amine Chemical compound C1[C@@H](C)O[C@@H](C)CN1CC1=NC(NC=2C=CC(=CC=2)C(C)(C)C)=C(C=CC(Br)=C2)C2=N1 FBXDMGNGVJSIEW-CALCHBBNSA-N 0.000 claims 1
- LGCVURLFWMTENV-UHFFFAOYSA-N 7-bromo-n-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]quinazolin-4-amine Chemical compound C1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC1=NC=NC2=CC(Br)=CC=C12 LGCVURLFWMTENV-UHFFFAOYSA-N 0.000 claims 1
- IFRRXVRHUIOTDX-UHFFFAOYSA-N 7-bromo-n-[4-(trifluoromethyl)phenyl]pyrido[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC=NC2=CC(Br)=CN=C12 IFRRXVRHUIOTDX-UHFFFAOYSA-N 0.000 claims 1
- ANISHZIMIBZQDK-UHFFFAOYSA-N 7-bromo-n-[4-(trifluoromethyl)phenyl]quinazolin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC=NC2=CC(Br)=CC=C12 ANISHZIMIBZQDK-UHFFFAOYSA-N 0.000 claims 1
- ODHMDLBWKDYTNZ-UHFFFAOYSA-N 7-bromo-n-[5-(trifluoromethyl)pyridin-2-yl]quinazolin-4-amine Chemical compound N1=CC(C(F)(F)F)=CC=C1NC1=NC=NC2=CC(Br)=CC=C12 ODHMDLBWKDYTNZ-UHFFFAOYSA-N 0.000 claims 1
- UGPMZGOAWMFREG-UHFFFAOYSA-N 7-chloro-2-(methoxymethyl)-n-[5-(trifluoromethyl)thiophen-2-yl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C=12C=CC(Cl)=NC2=NC(COC)=NC=1NC1=CC=C(C(F)(F)F)S1 UGPMZGOAWMFREG-UHFFFAOYSA-N 0.000 claims 1
- IPWPIHQSXCENPC-UHFFFAOYSA-N 7-chloro-2-methyl-n-[5-(trifluoromethyl)thiophen-2-yl]-1,8-naphthyridin-4-amine Chemical compound C=12C=CC(Cl)=NC2=NC(C)=CC=1NC1=CC=C(C(F)(F)F)S1 IPWPIHQSXCENPC-UHFFFAOYSA-N 0.000 claims 1
- NGFTYWGHSOYMIX-UHFFFAOYSA-N 7-chloro-n-[4-(trifluoromethyl)phenyl]quinazolin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC=NC2=CC(Cl)=CC=C12 NGFTYWGHSOYMIX-UHFFFAOYSA-N 0.000 claims 1
- OPRHFCJZJHATDF-UHFFFAOYSA-N 7-chloro-n-[5-(trifluoromethyl)thiophen-2-yl]-1,8-naphthyridin-4-amine Chemical compound S1C(C(F)(F)F)=CC=C1NC1=CC=NC2=NC(Cl)=CC=C12 OPRHFCJZJHATDF-UHFFFAOYSA-N 0.000 claims 1
- NTBKUIBYPDJFGQ-UHFFFAOYSA-N 7-chloro-n-[5-(trifluoromethyl)thiophen-2-yl]quinazolin-4-amine Chemical compound S1C(C(F)(F)F)=CC=C1NC1=NC=NC2=CC(Cl)=CC=C12 NTBKUIBYPDJFGQ-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 208000008035 Back Pain Diseases 0.000 claims 1
- 206010006482 Bronchospasm Diseases 0.000 claims 1
- 206010006784 Burning sensation Diseases 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 235000002566 Capsicum Nutrition 0.000 claims 1
- 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 claims 1
- 206010011224 Cough Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 208000031361 Hiccup Diseases 0.000 claims 1
- 206010020853 Hypertonic bladder Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000007914 Labor Pain Diseases 0.000 claims 1
- 208000035945 Labour pain Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims 1
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims 1
- 239000006002 Pepper Substances 0.000 claims 1
- 208000004983 Phantom Limb Diseases 0.000 claims 1
- 206010056238 Phantom pain Diseases 0.000 claims 1
- 235000016761 Piper aduncum Nutrition 0.000 claims 1
- 235000017804 Piper guineense Nutrition 0.000 claims 1
- 244000203593 Piper nigrum Species 0.000 claims 1
- 235000008184 Piper nigrum Nutrition 0.000 claims 1
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims 1
- 206010036790 Productive cough Diseases 0.000 claims 1
- 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 238000003915 air pollution Methods 0.000 claims 1
- 238000002266 amputation Methods 0.000 claims 1
- 230000002146 bilateral effect Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 230000007885 bronchoconstriction Effects 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 238000011109 contamination Methods 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 238000001514 detection method Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 201000006549 dyspepsia Diseases 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 230000000968 intestinal effect Effects 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 238000000670 ligand binding assay Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- RLDLCFVFAHWZKS-CALCHBBNSA-N n-(4-tert-butylphenyl)-2-[[(2s,6r)-2,6-dimethylmorpholin-4-yl]methyl]-7-(trifluoromethyl)quinazolin-4-amine Chemical compound C1[C@@H](C)O[C@@H](C)CN1CC1=NC(NC=2C=CC(=CC=2)C(C)(C)C)=C(C=CC(=C2)C(F)(F)F)C2=N1 RLDLCFVFAHWZKS-CALCHBBNSA-N 0.000 claims 1
- SKDPCTZAJURWKT-UHFFFAOYSA-N n-(4-tert-butylphenyl)-7-chloroquinazolin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC=NC2=CC(Cl)=CC=C12 SKDPCTZAJURWKT-UHFFFAOYSA-N 0.000 claims 1
- WGPQGSHPNGFRLO-UHFFFAOYSA-N n-(4-tert-butylphenyl)quinazolin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC=NC2=CC=CC=C12 WGPQGSHPNGFRLO-UHFFFAOYSA-N 0.000 claims 1
- JQEVLWMZLHMXTQ-UHFFFAOYSA-N n-(7-chloro-1,8-naphthyridin-4-yl)-2-methyl-1,3-thiazol-5-amine Chemical compound S1C(C)=NC=C1NC1=CC=NC2=NC(Cl)=CC=C12 JQEVLWMZLHMXTQ-UHFFFAOYSA-N 0.000 claims 1
- DIZFFTNLVYDUSF-UHFFFAOYSA-N n-(7-chloro-2-methyl-1,8-naphthyridin-4-yl)-2-(trifluoromethyl)-1,3-thiazol-5-amine Chemical compound C=12C=CC(Cl)=NC2=NC(C)=CC=1NC1=CN=C(C(F)(F)F)S1 DIZFFTNLVYDUSF-UHFFFAOYSA-N 0.000 claims 1
- MASSHYHYZKKCFY-UHFFFAOYSA-N n-(7-chloroquinazolin-4-yl)-5-(trifluoromethyl)-1,2-thiazol-3-amine Chemical compound S1C(C(F)(F)F)=CC(NC=2C3=CC=C(Cl)C=C3N=CN=2)=N1 MASSHYHYZKKCFY-UHFFFAOYSA-N 0.000 claims 1
- CEORTBLYXBSJQM-UHFFFAOYSA-N n-(7-fluoropyrido[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)-1,3-thiazol-5-amine Chemical compound N=1C=NC2=NC(F)=CC=C2C=1NC1=CN=C(C(F)(F)F)S1 CEORTBLYXBSJQM-UHFFFAOYSA-N 0.000 claims 1
- MNTILPFFUTUEGQ-UHFFFAOYSA-N n-[(1-cyclopentyl-5-fluorobenzimidazol-2-yl)methyl]-1-(2,4-dichlorophenyl)-n-[(2-ethoxynaphthalen-1-yl)methyl]methanamine Chemical compound CCOC1=CC=C2C=CC=CC2=C1CN(CC=1C(=CC(Cl)=CC=1)Cl)CC1=NC2=CC(F)=CC=C2N1C1CCCC1 MNTILPFFUTUEGQ-UHFFFAOYSA-N 0.000 claims 1
- MTVVXDQJKONPQJ-UHFFFAOYSA-N n-[(1-cyclopentylbenzimidazol-2-yl)methyl]-1-(2,4-dichlorophenyl)-n-[(2-ethoxynaphthalen-1-yl)methyl]methanamine Chemical compound CCOC1=CC=C2C=CC=CC2=C1CN(CC=1C(=CC(Cl)=CC=1)Cl)CC1=NC2=CC=CC=C2N1C1CCCC1 MTVVXDQJKONPQJ-UHFFFAOYSA-N 0.000 claims 1
- QYLQLNUNMVRQHA-UHFFFAOYSA-N n-[(3-fluorophenyl)methyl]-2-[3-(trifluoromethyl)phenyl]-1,6-naphthyridine-4-carboxamide Chemical compound FC1=CC=CC(CNC(=O)C=2C3=CN=CC=C3N=C(C=2)C=2C=C(C=CC=2)C(F)(F)F)=C1 QYLQLNUNMVRQHA-UHFFFAOYSA-N 0.000 claims 1
- UEYNCDPRXJRPQQ-UHFFFAOYSA-N n-[(6-chloro-1-propylbenzimidazol-2-yl)methyl]-1-(2,4-dichlorophenyl)-n-[(2-ethoxynaphthalen-1-yl)methyl]methanamine Chemical compound N=1C2=CC=C(Cl)C=C2N(CCC)C=1CN(CC=1C2=CC=CC=C2C=CC=1OCC)CC1=CC=C(Cl)C=C1Cl UEYNCDPRXJRPQQ-UHFFFAOYSA-N 0.000 claims 1
- FOSGJLYYBSRESD-UHFFFAOYSA-N n-[(7-chloro-1-propylbenzimidazol-2-yl)methyl]-1-(2,4-dichlorophenyl)-n-[(2-ethoxynaphthalen-1-yl)methyl]methanamine Chemical compound N=1C2=CC=CC(Cl)=C2N(CCC)C=1CN(CC=1C2=CC=CC=C2C=CC=1OCC)CC1=CC=C(Cl)C=C1Cl FOSGJLYYBSRESD-UHFFFAOYSA-N 0.000 claims 1
- UUTVGADTZHNXOU-UHFFFAOYSA-N n-[2-[(2,6-dimethylmorpholin-4-yl)methyl]-7-fluoroquinazolin-4-yl]-2-(trifluoromethyl)-1,3-thiazol-5-amine Chemical compound C1C(C)OC(C)CN1CC1=NC(NC=2SC(=NC=2)C(F)(F)F)=C(C=CC(F)=C2)C2=N1 UUTVGADTZHNXOU-UHFFFAOYSA-N 0.000 claims 1
- TVBBAECERWQUKW-UHFFFAOYSA-N n-[2-methyl-7-(trifluoromethyl)quinazolin-4-yl]-2-(trifluoromethyl)-1,3-thiazol-5-amine Chemical compound C=12C=CC(C(F)(F)F)=CC2=NC(C)=NC=1NC1=CN=C(C(F)(F)F)S1 TVBBAECERWQUKW-UHFFFAOYSA-N 0.000 claims 1
- JVHDBTRYJQIFJR-UHFFFAOYSA-N n-[7-chloro-2-(methoxymethyl)pteridin-4-yl]-2-(trifluoromethyl)-1,3-thiazol-5-amine Chemical compound C=12N=CC(Cl)=NC2=NC(COC)=NC=1NC1=CN=C(C(F)(F)F)S1 JVHDBTRYJQIFJR-UHFFFAOYSA-N 0.000 claims 1
- YCKBIQDTYTXHPG-UHFFFAOYSA-N n-[7-chloro-2-(methoxymethyl)pyrido[2,3-d]pyrimidin-4-yl]-2-(trifluoromethyl)-1,3-thiazol-5-amine Chemical compound C=12C=CC(Cl)=NC2=NC(COC)=NC=1NC1=CN=C(C(F)(F)F)S1 YCKBIQDTYTXHPG-UHFFFAOYSA-N 0.000 claims 1
- UGIJGLWYPSLKMH-UHFFFAOYSA-N n-[7-chloro-2-(methoxymethyl)pyrido[3,2-d]pyrimidin-4-yl]-2-(trifluoromethyl)-1,3-thiazol-5-amine Chemical compound C=12N=CC(Cl)=CC2=NC(COC)=NC=1NC1=CN=C(C(F)(F)F)S1 UGIJGLWYPSLKMH-UHFFFAOYSA-N 0.000 claims 1
- PNWFPYFWFSBXFM-UHFFFAOYSA-N n-[7-fluoro-2-(morpholin-4-ylmethyl)quinolin-4-yl]-2-(trifluoromethyl)-1,3-thiazol-5-amine Chemical compound C=1C(CN2CCOCC2)=NC2=CC(F)=CC=C2C=1NC1=CN=C(C(F)(F)F)S1 PNWFPYFWFSBXFM-UHFFFAOYSA-N 0.000 claims 1
- JVBGJAYPLMLZPQ-UHFFFAOYSA-N n-benzyl-2-(3-chlorophenyl)-1,6-naphthyridine-4-carboxamide Chemical compound ClC1=CC=CC(C=2N=C3C=CN=CC3=C(C(=O)NCC=3C=CC=CC=3)C=2)=C1 JVBGJAYPLMLZPQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 210000002569 neuron Anatomy 0.000 claims 1
- 201000009985 neuronitis Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 208000020629 overactive bladder Diseases 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 claims 1
- 230000035479 physiological effects, processes and functions Effects 0.000 claims 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
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- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
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- 238000001356 surgical procedure Methods 0.000 claims 1
- 239000003491 tear gas Substances 0.000 claims 1
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- 231100000331 toxic Toxicity 0.000 claims 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 206010044652 trigeminal neuralgia Diseases 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
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| US51624603P | 2003-10-31 | 2003-10-31 | |
| PCT/US2004/036295 WO2005042498A2 (en) | 2003-10-31 | 2004-10-28 | 4-amino (aza) quinoline derivatives as capsaicin receptor agonists |
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| JP (1) | JP2007509985A (https=) |
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| AU (1) | AU2004285052A1 (https=) |
| CA (1) | CA2540342A1 (https=) |
| WO (1) | WO2005042498A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2509233A1 (en) * | 2002-12-13 | 2004-07-01 | Neurogen Corporation | 2-substituted quinazolin-4-ylamine analogues as capsaicin receptor modulators |
| JP2007532570A (ja) * | 2004-04-08 | 2007-11-15 | ニューロジェン・コーポレーション | 置換シンノリン−４−イルアミン類 |
| EP1979348B1 (en) * | 2005-12-21 | 2012-01-18 | Abbott Laboratories | Anti-viral compounds |
| US7915411B2 (en) | 2005-12-21 | 2011-03-29 | Abbott Laboratories | Anti-viral compounds |
| US9757476B2 (en) * | 2006-06-08 | 2017-09-12 | Warsaw Orthopedic, Inc. | Compositions and methods for diagnosis of axial pain with or without radiculopathy |
| US20090227579A1 (en) * | 2006-06-23 | 2009-09-10 | Astrazeneca Ab | Pteridine Derivatives and their Use as Cathespin Inhibitors |
| US7943666B2 (en) * | 2006-07-24 | 2011-05-17 | Trinity Laboratories, Inc. | Esters of capsaicin for treating pain |
| JP2010501593A (ja) * | 2006-08-24 | 2010-01-21 | セレネックス， インコーポレイテッド | イソキノリン、キナゾリンおよびフタラジン誘導体 |
| US7645767B2 (en) | 2006-08-31 | 2010-01-12 | Trinity Laboratories, Inc. | Pharmaceutical compositions for treating chronic pain and pain associated with neuropathy |
| CA2672856C (en) * | 2006-12-15 | 2016-02-02 | Janssen Pharmaceutica N.V. | Benzimidazole trpv1 inhibitors |
| US8236950B2 (en) | 2006-12-20 | 2012-08-07 | Abbott Laboratories | Anti-viral compounds |
| EP2520561B1 (en) | 2007-06-08 | 2016-02-10 | MannKind Corporation | IRE-1A Inhibitors |
| BRPI0821209A2 (pt) * | 2007-12-19 | 2019-09-24 | Amgen Inc | composto, composição farmacêutica, métodos de tratar câncer, para reduzir o tamanho de tumor, para tratar distúrbios, e para reduzir metástase em um tumor. |
| US9415036B2 (en) * | 2008-02-15 | 2016-08-16 | Bone Therapeutics | Pharmaceutical composition for use in the treatment or prevention of osteoarticular diseases |
| PT2252290T (pt) | 2008-02-15 | 2018-02-14 | Bone Therapeutics Sa | Composição farmacêutica para utilização no tratamento e/ou prevenção de doenças osteoarticulares |
| US8389533B2 (en) * | 2008-04-07 | 2013-03-05 | Amgen Inc. | Gem-disubstituted and spirocyclic amino pyridines/pyrimidines as cell cycle inhibitors |
| JP5693452B2 (ja) | 2008-08-04 | 2015-04-01 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | 特定のキヌレニン−３−モノオキシゲナーゼインヒビター、医薬組成物およびそれらの使用方法 |
| AR075633A1 (es) | 2009-02-27 | 2011-04-20 | Ambit Biosciences Corp | Compuestos moduladores de jak quinasa y sus metodos de uso |
| EP2427056A4 (en) * | 2009-05-07 | 2012-08-22 | Univ Cincinnati | METHODS FOR PREVENTING ISCHEMIC LESION BY STIMULATION OF PERIPHERAL NICE PERIPHERAL |
| MX2012008346A (es) | 2010-01-25 | 2012-11-12 | Chdi Foundation Inc | Determinados inhibidores de cinurenina-3-monooxigenasa, composiciones farmceuticas y metodos de uso de los mismos. |
| WO2012030948A1 (en) | 2010-09-01 | 2012-03-08 | Ambit Biosciences Corporation | Quinazoline compounds and methods of use thereof |
| WO2012060845A1 (en) * | 2010-11-05 | 2012-05-10 | University Of Cincinnati | Methods of preventing ischemic injury using peripheral nociceptive stimulation |
| CN102091061B (zh) * | 2010-11-12 | 2012-07-04 | 河北医科大学 | 1,2-二苯乙烯衍生物在制药中的应用 |
| MX2013010163A (es) | 2011-03-09 | 2013-10-30 | Merck Patent Gmbh | Derivados de pirido[2,3-b] pirazina y sus usos terapeuticos. |
| CN103703000B (zh) | 2011-03-23 | 2015-11-25 | 安姆根有限公司 | Cdk4/6和flt3的稠合三环双重抑制剂 |
| MX2014002459A (es) | 2011-08-30 | 2014-04-10 | Chdi Foundation Inc | Inhibidores de quinurenina-3-monooxigenasa, composiciones farmaceuticas y metodos de uso de los mismos. |
| SI2750677T1 (sl) | 2011-08-30 | 2017-10-30 | Chdi Foundation, Inc. | Inhibitorji kinurenin-3-monooksigenaze, farmacevtski sestavki in postopki njihove uporabe |
| EP2948450A4 (en) * | 2013-01-28 | 2016-11-09 | Viamet Pharmaceuticals Inc | METALLOENZYMINHIBITORVERBINDUNGEN |
| US10092528B2 (en) | 2013-03-13 | 2018-10-09 | Altria Client Services Llc | Application of encapsulated capsaicin and analogues thereof for controlling calorie intake |
| CN106715421A (zh) | 2014-07-17 | 2017-05-24 | Chdi基金会股份有限公司 | 用于治疗hiv相关病症的方法和组合物 |
| CN107427506A (zh) | 2014-10-14 | 2017-12-01 | 拉霍拉敏感及免疫学研究所 | 低分子量蛋白酪氨酸磷酸酶的抑制剂及其用途 |
| WO2018204176A1 (en) * | 2017-05-01 | 2018-11-08 | Sanford Burnham Prebys Medical Discovery Institute | Inhibitors of low molecular weight protein tyrosine phosphatase (lmptp) and uses thereof |
| US12048693B2 (en) | 2018-01-05 | 2024-07-30 | Centre National De La Recherche Scientifique | Substituted halo-quinoline derivatives, method of preparation and applications thereof |
| CN108863949B (zh) * | 2018-07-09 | 2021-01-15 | 湖南博隽生物医药有限公司 | 一种用于治疗慢性炎性痛的辣椒素受体拮抗剂及合成方法 |
| US12486234B2 (en) | 2019-04-24 | 2025-12-02 | Children's Medical Center Corporation | PAPD5 inhibitors and methods of use thereof |
| US20250032476A1 (en) * | 2021-11-05 | 2025-01-30 | The Regents Of The University Of California | Alpha-2a adrenergic receptor modulators and uses thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5538325A (en) * | 1978-09-11 | 1980-03-17 | Sankyo Co Ltd | 4-anilinoquinazoline derivative and its preparation |
| US5034393A (en) * | 1989-07-27 | 1991-07-23 | Dowelanco | Fungicidal use of pyridopyrimidine, pteridine, pyrimidopyrimidine, pyrimidopyridazine, and pyrimido-1,2,4-triazine derivatives |
| GB9922171D0 (en) * | 1999-09-21 | 1999-11-17 | Zeneca Ltd | Chemical compounds |
| KR20020032608A (ko) * | 1999-09-21 | 2002-05-03 | 다비드 에 질레스 | 퀴나졸린 화합물 및 이를 함유하는 제약 조성물 |
| ATE394102T1 (de) * | 2000-06-28 | 2008-05-15 | Astrazeneca Ab | Substituierte chinazolin-derivate und deren verwendung als aurora-2-kinase inhibitoren |
| CN1627944A (zh) * | 2002-01-17 | 2005-06-15 | 神经能质公司 | 取代的喹唑啉－4－基胺类似物作为辣椒辣素调节剂 |
-
2004
- 2004-10-28 CN CNA2004800367091A patent/CN1890223A/zh active Pending
- 2004-10-28 EP EP04796879A patent/EP1678149A2/en not_active Withdrawn
- 2004-10-28 AU AU2004285052A patent/AU2004285052A1/en not_active Abandoned
- 2004-10-28 CA CA002540342A patent/CA2540342A1/en not_active Abandoned
- 2004-10-28 WO PCT/US2004/036295 patent/WO2005042498A2/en not_active Ceased
- 2004-10-28 JP JP2006538401A patent/JP2007509985A/ja not_active Withdrawn
-
2006
- 2006-04-26 US US11/412,526 patent/US20060194805A1/en not_active Abandoned
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