JP2011506466A - カルボキサミド化合物ならびにケモカイン受容体アゴニストとしてのそれらの使用 - Google Patents
カルボキサミド化合物ならびにケモカイン受容体アゴニストとしてのそれらの使用 Download PDFInfo
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- JP2011506466A JP2011506466A JP2010538152A JP2010538152A JP2011506466A JP 2011506466 A JP2011506466 A JP 2011506466A JP 2010538152 A JP2010538152 A JP 2010538152A JP 2010538152 A JP2010538152 A JP 2010538152A JP 2011506466 A JP2011506466 A JP 2011506466A
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- Japan
- Prior art keywords
- trifluoromethyl
- alkyl
- methyl
- pyrrolidin
- naphthyridin
- 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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- -1 Carboxamide compounds Chemical class 0.000 title claims description 105
- 239000002556 chemokine receptor agonist Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 297
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 49
- 201000010099 disease Diseases 0.000 claims abstract description 41
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 19
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 206010052779 Transplant rejections Diseases 0.000 claims abstract description 10
- 206010025135 lupus erythematosus Diseases 0.000 claims abstract description 10
- 208000009329 Graft vs Host Disease Diseases 0.000 claims abstract description 6
- 208000024908 graft versus host disease Diseases 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 161
- 238000000034 method Methods 0.000 claims description 118
- 125000003545 alkoxy group Chemical group 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 125000005843 halogen group Chemical group 0.000 claims description 47
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 239000003814 drug Substances 0.000 claims description 41
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
- 125000000304 alkynyl group Chemical group 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 15
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- UOTRVDWAHQBYSJ-UHFFFAOYSA-N 3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbaldehyde Chemical compound C1CN(C=O)CC2=CC(C(F)(F)F)=CN=C21 UOTRVDWAHQBYSJ-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 11
- 201000006417 multiple sclerosis Diseases 0.000 claims description 11
- 208000002193 Pain Diseases 0.000 claims description 10
- 201000004681 Psoriasis Diseases 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 201000004624 Dermatitis Diseases 0.000 claims description 7
- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 230000001684 chronic effect Effects 0.000 claims description 6
- 208000006454 hepatitis Diseases 0.000 claims description 6
- 231100000283 hepatitis Toxicity 0.000 claims description 6
- 210000000056 organ Anatomy 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 201000000306 sarcoidosis Diseases 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 206010012442 Dermatitis contact Diseases 0.000 claims description 5
- 206010047115 Vasculitis Diseases 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 201000001981 dermatomyositis Diseases 0.000 claims description 5
- 230000036961 partial effect Effects 0.000 claims description 5
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- VPGDDKHSBNUUEU-UHFFFAOYSA-N [3-(cyclopropylmethyl)-1-[4-hydroxy-4-(6-methoxypyridin-3-yl)cyclohexyl]pyrrolidin-3-yl]-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridin-6-yl]methanone Chemical compound C1=NC(OC)=CC=C1C1(O)CCC(N2CC(CC3CC3)(CC2)C(=O)N2CC3=CC(=CN=C3CC2)C(F)(F)F)CC1 VPGDDKHSBNUUEU-UHFFFAOYSA-N 0.000 claims description 4
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
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- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 4
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- SSOYENULCYRPAJ-UHFFFAOYSA-N 1-methyl-6-[[3-(3-methylbutyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]quinolin-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(CCC(C)C)CN(CC=2C=C3C=CC(=O)N(C)C3=CC=2)CC1 SSOYENULCYRPAJ-UHFFFAOYSA-N 0.000 claims description 3
- MCOGDABTARIBNK-UHFFFAOYSA-N 3-ethyl-6-[[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1,3-benzoxazol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C(COC)(C1)CCN1CC1=CC=C2N(CC)C(=O)OC2=C1 MCOGDABTARIBNK-UHFFFAOYSA-N 0.000 claims description 3
- ARJJRCWUUHZROE-UHFFFAOYSA-N 3-methyl-6-[[4-(2-methylpropyl)-4-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]piperidin-1-yl]methyl]-1,3-benzothiazol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(CC(C)C)CCN(CC=2C=C3SC(=O)N(C)C3=CC=2)CC1 ARJJRCWUUHZROE-UHFFFAOYSA-N 0.000 claims description 3
- BBCOGOZIEGWDSI-UHFFFAOYSA-N 5-[[3-(ethoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-3-methyl-1,3-benzoxazol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COCC)CN(CC=2C=C3N(C)C(=O)OC3=CC=2)CC1 BBCOGOZIEGWDSI-UHFFFAOYSA-N 0.000 claims description 3
- HZOYWQOTYROKEB-UHFFFAOYSA-N 5-[[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1,3-dimethylbenzimidazol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(CC=2C=C3N(C)C(=O)N(C)C3=CC=2)CC1 HZOYWQOTYROKEB-UHFFFAOYSA-N 0.000 claims description 3
- HSMJAYLNJMUKPQ-UHFFFAOYSA-N 5-bromo-6-[[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-3-methyl-1,3-benzoxazol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(CC=2C(=CC=3N(C)C(=O)OC=3C=2)Br)CC1 HSMJAYLNJMUKPQ-UHFFFAOYSA-N 0.000 claims description 3
- LGAFJIJPKCFJMJ-UHFFFAOYSA-N 6-[1-[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]ethyl]-4-methyl-1,4-benzoxazin-3-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(C(C)C=2C=C3N(C)C(=O)COC3=CC=2)CC1 LGAFJIJPKCFJMJ-UHFFFAOYSA-N 0.000 claims description 3
- MQRYXWFYGALVHE-DEOSSOPVSA-N 6-[[(3s)-3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-3-methyl-1,3-benzoxazol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)[C@]1(COC)CN(CC=2C=C3OC(=O)N(C)C3=CC=2)CC1 MQRYXWFYGALVHE-DEOSSOPVSA-N 0.000 claims description 3
- OQDPSJOSZREQPJ-UHFFFAOYSA-N 6-[[3-(cyclobutylmethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1-methylquinolin-2-one Chemical compound C1=C2C=CC(=O)N(C)C2=CC=C1CN(C1)CCC1(C(=O)N1CC2=CC(=CN=C2CC1)C(F)(F)F)CC1CCC1 OQDPSJOSZREQPJ-UHFFFAOYSA-N 0.000 claims description 3
- PIQVXZKFAQSKCR-UHFFFAOYSA-N 6-[[3-(cyclopropylmethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1-methylquinolin-2-one Chemical compound C1=C2C=CC(=O)N(C)C2=CC=C1CN(C1)CCC1(C(=O)N1CC2=CC(=CN=C2CC1)C(F)(F)F)CC1CC1 PIQVXZKFAQSKCR-UHFFFAOYSA-N 0.000 claims description 3
- OJWKSQPOCNEAPC-UHFFFAOYSA-N 6-[[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-4-methyl-1,4-benzoxazin-3-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(CC=2C=C3N(C)C(=O)COC3=CC=2)CC1 OJWKSQPOCNEAPC-UHFFFAOYSA-N 0.000 claims description 3
- QAYVYYSKSWMXHC-UHFFFAOYSA-N 6-chloro-7-[[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1-methylquinolin-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(CC=2C(=CC=3C=CC(=O)N(C)C=3C=2)Cl)CC1 QAYVYYSKSWMXHC-UHFFFAOYSA-N 0.000 claims description 3
- VUVWEEIPHLEDKR-NDEPHWFRSA-N 7-[[(3r)-3-(cyclopropylmethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1-methylquinolin-2-one Chemical compound C([C@]1(CCN(C1)CC=1C=C2N(C(C=CC2=CC=1)=O)C)C(=O)N1CC2=CC(=CN=C2CC1)C(F)(F)F)C1CC1 VUVWEEIPHLEDKR-NDEPHWFRSA-N 0.000 claims description 3
- VUVWEEIPHLEDKR-MUUNZHRXSA-N 7-[[(3s)-3-(cyclopropylmethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1-methylquinolin-2-one Chemical compound C([C@@]1(CCN(C1)CC=1C=C2N(C(C=CC2=CC=1)=O)C)C(=O)N1CC2=CC(=CN=C2CC1)C(F)(F)F)C1CC1 VUVWEEIPHLEDKR-MUUNZHRXSA-N 0.000 claims description 3
- DVJYNRLKAIQAGV-SANMLTNESA-N 7-[[(3s)-3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1-methylquinolin-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)[C@]1(COC)CN(CC=2C=C3N(C)C(=O)C=CC3=CC=2)CC1 DVJYNRLKAIQAGV-SANMLTNESA-N 0.000 claims description 3
- DVJYNRLKAIQAGV-UHFFFAOYSA-N 7-[[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1-methylquinolin-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(CC=2C=C3N(C)C(=O)C=CC3=CC=2)CC1 DVJYNRLKAIQAGV-UHFFFAOYSA-N 0.000 claims description 3
- LGKXVKJQRSAWHU-UHFFFAOYSA-N [1-[4-(4-fluorophenyl)cyclohexyl]-3-(methoxymethyl)pyrrolidin-3-yl]-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridin-6-yl]methanone Chemical compound C1C(COC)(C(=O)N2CC3=CC(=CN=C3CC2)C(F)(F)F)CCN1C(CC1)CCC1C1=CC=C(F)C=C1 LGKXVKJQRSAWHU-UHFFFAOYSA-N 0.000 claims description 3
- ISTJMLJJSJJKIJ-UHFFFAOYSA-N [3-(cyclopropylmethyl)-1-[(2,2-dimethyloxan-4-yl)methyl]pyrrolidin-3-yl]-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridin-6-yl]methanone Chemical compound C1COC(C)(C)CC1CN1CC(CC2CC2)(C(=O)N2CC3=CC(=CN=C3CC2)C(F)(F)F)CC1 ISTJMLJJSJJKIJ-UHFFFAOYSA-N 0.000 claims description 3
- OYALIWAZSPYDLP-UHFFFAOYSA-N [3-(cyclopropylmethyl)-1-[(4-hydroxy-3-methoxyphenyl)methyl]pyrrolidin-3-yl]-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridin-6-yl]methanone Chemical compound C1=C(O)C(OC)=CC(CN2CC(CC3CC3)(CC2)C(=O)N2CC3=CC(=CN=C3CC2)C(F)(F)F)=C1 OYALIWAZSPYDLP-UHFFFAOYSA-N 0.000 claims description 3
- CIAUEEMOFGNWIP-UHFFFAOYSA-N [3-(cyclopropylmethyl)-1-[(5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)methyl]pyrrolidin-3-yl]-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridin-6-yl]methanone Chemical compound COC1=CC=2CC(C)OC=2C=C1CN(C1)CCC1(C(=O)N1CC2=CC(=CN=C2CC1)C(F)(F)F)CC1CC1 CIAUEEMOFGNWIP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
- 125000004419 alkynylene group Chemical group 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- NPJCOYIDFDZMOG-UHFFFAOYSA-N 1-methyl-7-[[4-(2-methylpropyl)-4-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]piperidin-1-yl]methyl]quinolin-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(CC(C)C)CCN(CC=2C=C3N(C)C(=O)C=CC3=CC=2)CC1 NPJCOYIDFDZMOG-UHFFFAOYSA-N 0.000 claims description 2
- CKLRTGAHPHXPHJ-UHFFFAOYSA-N 2-[1-[(3-methyl-2-oxo-1,3-benzoxazol-5-yl)methyl]-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-3-yl]acetonitrile Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C(CC#N)(C1)CCN1CC1=CC=C(OC(N2C)=O)C2=C1 CKLRTGAHPHXPHJ-UHFFFAOYSA-N 0.000 claims description 2
- DSKGYYQAONVBIQ-UHFFFAOYSA-N 3-methyl-5-[[3-(2-methylpropyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1,3-benzoxazol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(CC(C)C)CN(CC=2C=C3N(C)C(=O)OC3=CC=2)CC1 DSKGYYQAONVBIQ-UHFFFAOYSA-N 0.000 claims description 2
- JGGYDCZSDBBBRD-UHFFFAOYSA-N 5-[2-[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]propan-2-yl]-3-methyl-1,3-benzoxazol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(C(C)(C)C=2C=C3N(C)C(=O)OC3=CC=2)CC1 JGGYDCZSDBBBRD-UHFFFAOYSA-N 0.000 claims description 2
- GVSZOQGJDKGPGZ-UHFFFAOYSA-N 5-[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]-3-methyl-6,7-dihydro-5h-cyclopenta[f][1,3]benzoxazol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(C2C3=CC=4N(C)C(=O)OC=4C=C3CC2)CC1 GVSZOQGJDKGPGZ-UHFFFAOYSA-N 0.000 claims description 2
- QZGNXUYSPSJETI-UHFFFAOYSA-N 5-[[3-(cyclopropylmethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-3h-1,3-benzothiazol-2-one Chemical compound C1C2=CC(C(F)(F)F)=CN=C2CCN1C(=O)C1(CN(CC=2C=C3NC(=O)SC3=CC=2)CC1)CC1CC1 QZGNXUYSPSJETI-UHFFFAOYSA-N 0.000 claims description 2
- GMBBPAFILXICGE-UHFFFAOYSA-N 5-[[3-(methoxymethyl)-3-[3-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-b]pyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-3-methyl-1,3-benzoxazol-2-one Chemical compound C1C2=CC(C(F)(F)F)=CN=C2CN1C(=O)C1(COC)CN(CC=2C=C3N(C)C(=O)OC3=CC=2)CC1 GMBBPAFILXICGE-UHFFFAOYSA-N 0.000 claims description 2
- LYUCMMACNKQXBC-UHFFFAOYSA-N 5-[[3-(methoxymethyl)-3-[7-(trifluoromethyl)-3,4-dihydro-1h-isoquinoline-2-carbonyl]pyrrolidin-1-yl]methyl]-3-methyl-1,3-benzoxazol-2-one Chemical compound C1CC2=CC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(CC=2C=C3N(C)C(=O)OC3=CC=2)CC1 LYUCMMACNKQXBC-UHFFFAOYSA-N 0.000 claims description 2
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Diabetes (AREA)
- Cardiology (AREA)
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- Emergency Medicine (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1281907P | 2007-12-11 | 2007-12-11 | |
| US3667508P | 2008-03-14 | 2008-03-14 | |
| PCT/US2008/086388 WO2009076512A1 (en) | 2007-12-11 | 2008-12-11 | Carboxamidξ compounds and their use as chemokine receptor agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011506466A true JP2011506466A (ja) | 2011-03-03 |
| JP2011506466A5 JP2011506466A5 (enExample) | 2012-02-02 |
Family
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| EP2142529B1 (en) | 2007-04-27 | 2013-12-25 | Purdue Pharma LP | Trpv1 antagonists and uses thereof |
| AU2008335135A1 (en) | 2007-12-11 | 2009-06-18 | Cytopathfinder, Inc. | Carboxamide compounds and their use as chemokine receptor agonists |
| NZ595431A (en) * | 2009-04-16 | 2013-12-20 | Janssen Pharmaceutica Nv | 4-azetidinyl-1-heteroaryl-cyclohexane antagonists of ccr2 |
| ES2528625T3 (es) * | 2009-04-17 | 2015-02-11 | Janssen Pharmaceutica Nv | Antagonistas de 4-azetidinil-1-fenil-ciclohexano de CCR2 |
| CA2758929A1 (en) * | 2009-04-17 | 2010-10-21 | Janssen Pharmaceutica Nv | 4-azetidinyl-1-heteroatom linked-cyclohexane antagonists of ccr2 |
| RS55701B1 (sr) | 2011-06-22 | 2017-07-31 | Purdue Pharma Lp | Trpv1 antagonisti koji uključuju dihidroksi supstituent i njihove upotrebe |
| GB201115633D0 (en) * | 2011-09-09 | 2011-10-26 | Univ Liverpool | Compositions of efavirenz |
| JO3407B1 (ar) * | 2012-05-31 | 2019-10-20 | Eisai R&D Man Co Ltd | مركبات رباعي هيدرو بيرازولو بيريميدين |
| TWI876212B (zh) * | 2021-10-01 | 2025-03-11 | 美商辛瑟拉股份有限公司 | 吖丁啶及吡咯啶parp1抑制劑及其用途 |
| CN120081844A (zh) | 2022-01-21 | 2025-06-03 | 新特拉有限公司 | Parp1抑制剂及其用途 |
| US20250214980A1 (en) | 2022-03-14 | 2025-07-03 | Slap Pharmaceuticals Llc | Multicyclic compounds |
| PT4497438T (pt) | 2022-04-28 | 2025-10-31 | Xinthera Inc C/O Gilead Sciences Inc | Inibidores tricíclicos da parp1 e suas utilizações |
| CN121969618A (zh) * | 2023-09-13 | 2026-05-01 | 中国药科大学 | 氮杂环丁烷衍生物、其制备方法及其医药用途 |
| WO2025131049A1 (en) * | 2023-12-21 | 2025-06-26 | Ignis Therapeutics (Suzhou) Limited | Dihydro-pyrrolo-pyridine derivatives and uses thereof |
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| JPN6013035158; ＴＡＢＵＣＨＩ， Ｓ． ｅｔ ａｌ．: 'Ｎｏｖｅｌ ｐｏｔｅｎｔ ａｎｔａｇｏｎｉｓｔｓ ｏｆ ｈｕｍａｎ ｎｅｕｒｏｐｅｐｔｉｄｅ Ｙ Ｙ５ ｒｅｃｅｐｔｏｒ． Ｐａｒｔ １： ２-ｏｘｏｂｅｎｚｏｔｈｉａｚｏｌｉｎ-３-ａｃｅｔｉｃ ａ' Ｂｉｏｏｒｇａｎｉｃ ＆ Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍｉｓｔｒｙ Ｌｅｔｔｅｒｓ Ｖｏｌ．１２， Ｎｏ．８, 2002, ｐ．１１７１-１１７５ * |
| JPN6014021476; 化学大辞典１ 縮刷版 , 1963, ｐ．３７７ 「アルキル」, 共立出版株式会社 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009076512A1 (en) | 2009-06-18 |
| US8569282B2 (en) | 2013-10-29 |
| CN101925383A (zh) | 2010-12-22 |
| CA2708364A1 (en) | 2009-06-18 |
| AU2008335135A1 (en) | 2009-06-18 |
| KR20100102646A (ko) | 2010-09-24 |
| EP2280766A1 (en) | 2011-02-09 |
| BRPI0820701A2 (pt) | 2015-06-16 |
| RU2010128543A (ru) | 2012-01-20 |
| US20100324035A1 (en) | 2010-12-23 |
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