KR20100102646A - 카르복스아미드 화합물 및 케모카인 수용체 길항제로서의 이의 용도 - Google Patents
카르복스아미드 화합물 및 케모카인 수용체 길항제로서의 이의 용도 Download PDFInfo
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- KR20100102646A KR20100102646A KR1020107015232A KR20107015232A KR20100102646A KR 20100102646 A KR20100102646 A KR 20100102646A KR 1020107015232 A KR1020107015232 A KR 1020107015232A KR 20107015232 A KR20107015232 A KR 20107015232A KR 20100102646 A KR20100102646 A KR 20100102646A
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- KR
- South Korea
- Prior art keywords
- trifluoromethyl
- alkyl
- methyl
- carbonyl
- tetrahydro
- 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.)
- Ceased
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- -1 Carboxamide compounds Chemical class 0.000 title claims description 118
- 239000002556 chemokine receptor agonist Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 321
- 238000011282 treatment Methods 0.000 claims abstract description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 156
- 238000000034 method Methods 0.000 claims description 119
- 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
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000005843 halogen group Chemical group 0.000 claims description 45
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- 201000010099 disease Diseases 0.000 claims description 37
- 239000003814 drug Substances 0.000 claims description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 201000001320 Atherosclerosis Diseases 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000003161 (C1-C6) alkylene group Chemical group 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 208000002193 Pain Diseases 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 206010025135 lupus erythematosus Diseases 0.000 claims description 11
- 201000006417 multiple sclerosis Diseases 0.000 claims description 11
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 11
- 201000004681 Psoriasis Diseases 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 230000036407 pain Effects 0.000 claims description 10
- 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 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 201000004624 Dermatitis Diseases 0.000 claims description 8
- 206010052779 Transplant rejections Diseases 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 6
- 208000009329 Graft vs Host Disease 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
- 206010047115 Vasculitis Diseases 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 208000024908 graft versus host disease Diseases 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
- 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
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 5
- 208000008589 Obesity Diseases 0.000 claims description 5
- 230000001684 chronic effect Effects 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 230000036961 partial effect Effects 0.000 claims description 5
- 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 4
- XZOXQUIEYCYENT-UHFFFAOYSA-N 5-[[3-(cyclopropylmethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-3-methyl-1,3-benzothiazol-2-one Chemical compound C=1C=C2SC(=O)N(C)C2=CC=1CN(C1)CCC1(C(=O)N1CC2=CC(=CN=C2CC1)C(F)(F)F)CC1CC1 XZOXQUIEYCYENT-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 4
- SMGCPEBUGLUKSJ-UHFFFAOYSA-N [3-(methoxymethyl)-1-[4-(6-methoxypyridin-3-yl)cyclohexyl]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(OC)N=C1 SMGCPEBUGLUKSJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 208000010247 contact dermatitis 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 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 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
- KYDUDOKAGFWMCQ-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-benzoxazol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(CC(C)C)CCN(CC=2C=C3OC(=O)N(C)C3=CC=2)CC1 KYDUDOKAGFWMCQ-UHFFFAOYSA-N 0.000 claims description 3
- FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical compound O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 claims description 3
- XQYUYQDUPFWDFK-UHFFFAOYSA-N 5-[[3-(cyclopropylmethyl)-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 C=1C=C2OC(=O)N(C)C2=CC=1CN(C1)CCC1(C(=O)N1CC2=CC(=CN=C2CC1)C(F)(F)F)CC1CC1 XQYUYQDUPFWDFK-UHFFFAOYSA-N 0.000 claims description 3
- 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 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
- MUYBWGUUSUXSGK-UHFFFAOYSA-N 5-[[3-(hydroxymethyl)-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(CO)(C1)CCN1CC1=CC=C(OC(N2C)=O)C2=C1 MUYBWGUUSUXSGK-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
- FTRAKWZYZZKAGK-UHFFFAOYSA-N 5-[[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-3-methyl-1,3-benzothiazol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(CC=2C=C3N(C)C(=O)SC3=CC=2)CC1 FTRAKWZYZZKAGK-UHFFFAOYSA-N 0.000 claims description 3
- JKEOMFGBWCCTCB-UHFFFAOYSA-N 5-[[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=C3N(C)C(=O)OC3=CC=2)CC1 JKEOMFGBWCCTCB-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
- FISBGIQSOYEZGM-UHFFFAOYSA-N 6-[[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-3,5-dimethyl-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)C)CC1 FISBGIQSOYEZGM-UHFFFAOYSA-N 0.000 claims description 3
- KAHPAFVECYYWPH-UHFFFAOYSA-N 6-chloro-5-[[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=3OC(=O)N(C)C=3C=2)Cl)CC1 KAHPAFVECYYWPH-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
- DVJYNRLKAIQAGV-AREMUKBSSA-N 7-[[(3r)-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-AREMUKBSSA-N 0.000 claims description 3
- VUVWEEIPHLEDKR-UHFFFAOYSA-N 7-[[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=1C=C2C=CC(=O)N(C)C2=CC=1CN(C1)CCC1(C(=O)N1CC2=CC(=CN=C2CC1)C(F)(F)F)CC1CC1 VUVWEEIPHLEDKR-UHFFFAOYSA-N 0.000 claims description 3
- FVLARIBCAOKFPC-UHFFFAOYSA-N 7-[[3-(cyclopropylmethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1h-quinolin-2-one Chemical compound C1C2=CC(C(F)(F)F)=CN=C2CCN1C(=O)C1(CN(CC=2C=C3NC(=O)C=CC3=CC=2)CC1)CC1CC1 FVLARIBCAOKFPC-UHFFFAOYSA-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
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 3
- KSGFGNPWKSGEIX-UHFFFAOYSA-N [1-[4-hydroxy-4-(6-methoxypyridin-3-yl)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)CCC1(O)C1=CC=C(OC)N=C1 KSGFGNPWKSGEIX-UHFFFAOYSA-N 0.000 claims description 3
- XUAUUMXAZGNEDU-UHFFFAOYSA-N [3-(cyclopropylmethyl)-1-(1h-indazol-5-ylmethyl)pyrrolidin-3-yl]-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridin-6-yl]methanone Chemical compound C1C2=CC(C(F)(F)F)=CN=C2CCN1C(=O)C1(CN(CC=2C=C3C=NNC3=CC=2)CC1)CC1CC1 XUAUUMXAZGNEDU-UHFFFAOYSA-N 0.000 claims description 3
- WCUDZOJOQRBGIP-UHFFFAOYSA-N [3-(cyclopropylmethyl)-1-(oxan-4-ylmethyl)pyrrolidin-3-yl]-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridin-6-yl]methanone Chemical compound C1C2=CC(C(F)(F)F)=CN=C2CCN1C(=O)C1(CN(CC2CCOCC2)CC1)CC1CC1 WCUDZOJOQRBGIP-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
- 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 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 3
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Classifications
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Landscapes
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Applications Claiming Priority (4)
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| US1281907P | 2007-12-11 | 2007-12-11 | |
| US61/012,819 | 2007-12-11 | ||
| US3667508P | 2008-03-14 | 2008-03-14 | |
| US61/036,675 | 2008-03-14 |
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| KR20100102646A true KR20100102646A (ko) | 2010-09-24 |
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| US8269015B2 (en) * | 2009-04-16 | 2012-09-18 | Janssen Pharmaceutica N.V. | 4-azetidinyl-1-heteroaryl-cyclohexane antagonists of CCR2 |
| WO2010121046A1 (en) * | 2009-04-17 | 2010-10-21 | Janssen Pharmaceutica Nv | 4-azetidinyl-1-phenyl-cyclohexane antagonists of ccr2 |
| AU2010236336B2 (en) * | 2009-04-17 | 2015-01-15 | Janssen Pharmaceutica Nv | 4-azetidinyl-1-heteroatom linked-cyclohexane antagonists of CCR2 |
| JP5699251B2 (ja) | 2011-06-22 | 2015-04-08 | パーデュー、ファーマ、リミテッド、パートナーシップ | ジヒドロキシ置換基を包含するｔｒｐｖ１アンタゴニストおよびその使用 |
| 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 |
| KR102867210B1 (ko) * | 2021-10-01 | 2025-10-14 | 신테라, 인크. | 아제티딘 및 피롤리딘 parp1 저해제, 및 이의 용도 |
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| AU2023235233A1 (en) | 2022-03-14 | 2024-09-12 | Slap Pharmaceuticals Llc | Multicyclic compounds |
| LT4355749T (lt) | 2022-04-28 | 2025-08-25 | Xinthera, Inc. | Tricikliniai parp1 inhibitoriai ir jų panaudojimo būdai |
| WO2025055965A1 (zh) * | 2023-09-13 | 2025-03-20 | 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 |
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Family Cites Families (111)
| Publication number | Priority date | Publication date | Assignee | Title |
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- 2008-12-11 US US12/747,109 patent/US8569282B2/en not_active Expired - Fee Related
- 2008-12-11 EP EP08858495A patent/EP2280766A1/en not_active Withdrawn
- 2008-12-11 RU RU2010128543/04A patent/RU2010128543A/ru not_active Application Discontinuation
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- 2008-12-11 AU AU2008335135A patent/AU2008335135A1/en not_active Abandoned
- 2008-12-11 JP JP2010538152A patent/JP2011506466A/ja active Pending
- 2008-12-11 CA CA2708364A patent/CA2708364A1/en not_active Abandoned
- 2008-12-11 WO PCT/US2008/086388 patent/WO2009076512A1/en not_active Ceased
- 2008-12-11 KR KR1020107015232A patent/KR20100102646A/ko not_active Ceased
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| CA2708364A1 (en) | 2009-06-18 |
| US8569282B2 (en) | 2013-10-29 |
| JP2011506466A (ja) | 2011-03-03 |
| CN101925383A (zh) | 2010-12-22 |
| EP2280766A1 (en) | 2011-02-09 |
| BRPI0820701A2 (pt) | 2015-06-16 |
| WO2009076512A1 (en) | 2009-06-18 |
| RU2010128543A (ru) | 2012-01-20 |
| US20100324035A1 (en) | 2010-12-23 |
| AU2008335135A1 (en) | 2009-06-18 |
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