JP2011506466A5 - - Google Patents
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- JP2011506466A5 JP2011506466A5 JP2010538152A JP2010538152A JP2011506466A5 JP 2011506466 A5 JP2011506466 A5 JP 2011506466A5 JP 2010538152 A JP2010538152 A JP 2010538152A JP 2010538152 A JP2010538152 A JP 2010538152A JP 2011506466 A5 JP2011506466 A5 JP 2011506466A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- alkyl
- methyl
- carbonyl
- pyrrolidin
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 112
- 150000001875 compounds Chemical class 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- -1 3- (cyclopropylmethyl) -1- (3-fluoro-4-hydroxybenzyl) pyrrolidin-3-yl Chemical group 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 17
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 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
- 201000001320 Atherosclerosis Diseases 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 7
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 208000006454 hepatitis Diseases 0.000 claims description 5
- 231100000283 hepatitis Toxicity 0.000 claims description 5
- 206010025135 lupus erythematosus Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 210000000056 organ Anatomy 0.000 claims description 5
- 201000000306 sarcoidosis Diseases 0.000 claims description 5
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
- 201000004624 Dermatitis Diseases 0.000 claims description 4
- 206010012442 Dermatitis contact Diseases 0.000 claims description 4
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 4
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 4
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 206010052779 Transplant rejections Diseases 0.000 claims description 4
- 206010047115 Vasculitis 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
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 208000010247 contact dermatitis Diseases 0.000 claims description 4
- 201000001981 dermatomyositis Diseases 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 208000024908 graft versus host disease Diseases 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 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 3
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000004122 cyclic 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
- 230000002265 prevention Effects 0.000 claims description 3
- 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 2
- 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
- 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
- VLPXLRNYTZAUQV-UHFFFAOYSA-N 3-methyl-5-[[3-propan-2-yl-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(C(C)C)CN(CC=2C=C3N(C)C(=O)OC3=CC=2)CC1 VLPXLRNYTZAUQV-UHFFFAOYSA-N 0.000 claims description 2
- WURIWQGPKUGNDP-UHFFFAOYSA-N 5-[[3-(3,4-dihydro-1h-isoquinoline-2-carbonyl)-3-(methoxymethyl)pyrrolidin-1-yl]methyl]-3-methyl-1,3-benzoxazol-2-one Chemical compound C1CC2=CC=CC=C2CN1C(=O)C1(COC)CN(CC=2C=C3N(C)C(=O)OC3=CC=2)CC1 WURIWQGPKUGNDP-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
- 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 2
- 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 2
- HYMXRSJFWFORFH-UHFFFAOYSA-N 6-[1-[3-(ethoxymethyl)-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(COCC)CN(C(C)C=2C=C3N(C)C(=O)COC3=CC=2)CC1 HYMXRSJFWFORFH-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- FADIXOKHZVMUMM-UHFFFAOYSA-N 6-[[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1-methyl-3h-indol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(CC=2C=C3N(C)C(=O)CC3=CC=2)CC1 FADIXOKHZVMUMM-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 229910014033 C-OH Inorganic materials 0.000 claims description 2
- BVRPLTMBPRZLRH-UHFFFAOYSA-N C1CC1CC2CCN(C2)CC3CCOCC3 Chemical compound C1CC1CC2CCN(C2)CC3CCOCC3 BVRPLTMBPRZLRH-UHFFFAOYSA-N 0.000 claims description 2
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- 229910014570 C—OH Inorganic materials 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- OOQHONFKITXICX-UHFFFAOYSA-N [1-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(2-methylpropyl)piperidin-4-yl]-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridin-6-yl]methanone Chemical compound C1=C(O)C(OC)=CC(CN2CCC(CC(C)C)(CC2)C(=O)N2CC3=CC(=CN=C3CC2)C(F)(F)F)=C1 OOQHONFKITXICX-UHFFFAOYSA-N 0.000 claims description 2
- NMPJMQVHGFJCHG-UHFFFAOYSA-N [1-[4-fluoro-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(F)C1=CC=C(OC)N=C1 NMPJMQVHGFJCHG-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 4
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Family Cites Families (111)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB860303A (en) | 1958-06-20 | 1961-02-01 | Ici Ltd | Pharmaceutical compositions comprising ª‡-aryloxy-aliphatic carboxylic acids and/or ª |
| US3383281A (en) | 1961-09-22 | 1968-05-14 | Merck & Co Inc | Method for binding bile acids in vivo |
| SE353319B (cg-RX-API-DMAC7.html) | 1964-08-15 | 1973-01-29 | Sumitomo Chemical Co | |
| US3674836A (en) | 1968-05-21 | 1972-07-04 | Parke Davis & Co | 2,2-dimethyl-{11 -aryloxy-alkanoic acids and salts and esters thereof |
| US4058552A (en) | 1969-01-31 | 1977-11-15 | Orchimed Sa | Esters of p-carbonylphenoxy-isobutyric acids |
| US3803237A (en) | 1969-11-03 | 1974-04-09 | Upjohn Co | Reaction products of polyethylenepolyamines and chlorohydrins or epoxy containing compounds |
| US3692895A (en) | 1970-09-08 | 1972-09-19 | Norman A Nelson | Method of reducing hypercholesteremia in humans employing a copolymer of polyethylenepolyamine and a bifunctional substance, such as epichlorohydria |
| DE2230383C3 (de) | 1971-10-01 | 1981-12-03 | Boehringer Mannheim Gmbh, 6800 Mannheim | Phenoxyalkylcarbonsäurederivate und Verfahren zur Herstellung derselben |
| DE2708913A1 (de) | 1976-03-04 | 1977-09-08 | Hoechst Ag | Benzoylpiperidyalkyl-indole und verwandte verbindungen |
| FR2350341A1 (fr) | 1976-05-07 | 1977-12-02 | Synthelabo | Nouveaux derives de piperidine et leur methode de preparation |
| GB2021108B (en) | 1978-05-18 | 1982-07-21 | Pfizer Ltd | 6,7 - di - 4 - amino - 2 - quinazolines |
| DK159079A (da) * | 1978-05-18 | 1979-11-19 | Pfizer | Fremgangsmaade til fremstilling af derivater af 4-amino-2-piperidinoquinazolin eller syreadditionssalte deraf |
| DE2928485A1 (de) | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
| US4452813A (en) | 1981-05-22 | 1984-06-05 | Taiho Pharmaceutical Company Limited | Sulfonate derivatives, process for preparing same and antilipemic compositions containing the derivative |
| CA1247547A (en) | 1983-06-22 | 1988-12-28 | Paul Hadvary | Leucine derivatives |
| US4847271A (en) | 1986-01-27 | 1989-07-11 | Merck & Co., Inc. | Antihypercholesterolemic β-lactones |
| US5041432A (en) | 1987-01-30 | 1991-08-20 | E. I. Du Pont De Nemours And Company | Steroid derivatives useful as hypocholesterolemics |
| US4716175A (en) | 1987-02-24 | 1987-12-29 | Warner-Lambert Company | Saturated fatty acid amides as inhibitors of acyl-CoA:cholesterol acyltransferase |
| US5015644A (en) | 1987-06-02 | 1991-05-14 | Warner-Lambert Company | Antihyperlipidemic and antiatherosclerotic urea and carbamate compounds |
| EP0306375A1 (fr) * | 1987-08-07 | 1989-03-08 | Synthelabo | Dérivés de[(pipéridinyl-4)méthyl]-2 tétrahydro-1,2,3,4 isoquinoléine, leur préparation et leur application en thérapeutique |
| WO1990005132A1 (fr) | 1988-11-11 | 1990-05-17 | Banyu Pharmaceutical Co., Ltd. | Derives d'allylamine substitues, procede de preparation et utilisation |
| US5064856A (en) | 1989-07-31 | 1991-11-12 | Merck & Co., Inc. | Novel hmg-coa synthase inhibitors |
| US5391571A (en) | 1989-11-15 | 1995-02-21 | American Home Products Corporation | Cholesterol ester hydrolase inhibitors |
| SE8904298D0 (sv) | 1989-12-21 | 1989-12-21 | Astra Ab | New compounds |
| US5051534A (en) | 1990-03-22 | 1991-09-24 | Merrell Dow Pharmaceuticals Inc. | Novel cyclopropyl squalene derivatives and their use as inhibitors of cholesterol synthesis |
| US5102915A (en) | 1990-03-22 | 1992-04-07 | Merrell Dow Pharmaceuticals Inc. | Cyclopropyl squalene derivatives and their use as inhibitors of cholesterol synthesis |
| US5064864A (en) | 1990-03-30 | 1991-11-12 | Merrell Dow Pharmaceuticals Inc. | Di- and tetra-fluoro analogs of squalene as inhibitors of squalene epoxidase |
| US5011859A (en) | 1990-03-30 | 1991-04-30 | Merrell Dow Pharmaceuticals Inc. | Di- and tetra-fluoro analogs of squalene as inhibitors of squalene epoxidase |
| US5120729A (en) | 1990-06-20 | 1992-06-09 | Merck & Co., Inc. | Beta-lactams as antihypercholesterolemics |
| NZ239022A (en) | 1990-07-25 | 1993-11-25 | Merrell Dow Pharma | Piperidyl ethers and thioethers; preparatory processes and pharmaceutical compositions |
| US5026554A (en) | 1990-09-13 | 1991-06-25 | Merck & Co., Inc. | Method of inhibiting fungal growth using squalene synthetase inhibitors |
| US5084461A (en) | 1991-03-27 | 1992-01-28 | Merrell Dow Pharmaceuticals Inc. | Azadecalin amides and thioamides as inhibitors of cholesterol biosynthesis |
| US5274143A (en) | 1991-07-23 | 1993-12-28 | Hoffmann-La Roche Inc. | Process for the preparation of (R)-3-hexyl-5,6-dihydro-4-hydroxy-6-undecyl-2H-pyran-2-one and (R)-5,6-dihydro-6-undecyl-2H-pyran-2,4(3H)-dione |
| WO1993011782A1 (en) | 1991-12-19 | 1993-06-24 | Southwest Foundation For Biomedical Research | Cetp inhibitor polypeptide, antibodies against the synthetic polypeptide and prophylactic and therapeutic anti-atherosclerosis treatments |
| CA2098167C (en) | 1992-06-24 | 2006-12-19 | Dorothea Isler | Foodstuffs and feedstuffs containing a lipase inhibitor |
| FR2697252B1 (fr) | 1992-10-28 | 1994-12-09 | Fournier Ind & Sante | Dérivés de 1,2,3,5,6,7,8,8a-octahydro-5,5,8a-triméthyl-(8abeta)-6-isoquinolineamine, leur procédé de préparation et leur utilisation en thérapeutique. |
| US5364867A (en) | 1992-11-30 | 1994-11-15 | Sterling Winthrop Inc. | 4-phenylpiperdine agents for treating cns disorders |
| US5635510A (en) | 1993-05-06 | 1997-06-03 | Merrell Pharmaceuticals Inc. | Substituted pyrrolidin-3-yl-alkyl-piperidines |
| US5824690A (en) | 1993-05-06 | 1998-10-20 | Hoechst Marion Roussel Inc. | Substituted pyrrolidin-3-yl-alkyl-piperidines |
| TW381025B (en) | 1993-08-05 | 2000-02-01 | Hoffmann La Roche | Pharmaceutical composition containing a glucosidase inhibitor and a lipase inhibitor |
| SE9400447D0 (sv) | 1994-02-11 | 1994-02-11 | Astra Ab | New compounds |
| US5576313A (en) | 1994-08-29 | 1996-11-19 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US5475109A (en) | 1994-10-17 | 1995-12-12 | Merck & Co., Inc. | Dioxobutanoic acid derivatives as inhibitors of influenza endonuclease |
| US6268369B1 (en) | 1994-11-16 | 2001-07-31 | Synaptic Pharmaceutical Corporation | 5-(heterocyclic alkyl)-6-aryl-dihydropyrimidines |
| WO1996014846A1 (en) | 1994-11-16 | 1996-05-23 | Synaptic Pharmaceutical Corporation | Dihydropyrimidines and uses thereof |
| US5510379A (en) | 1994-12-19 | 1996-04-23 | Warner-Lambert Company | Sulfonate ACAT inhibitors |
| US5696267A (en) | 1995-05-02 | 1997-12-09 | Schering Corporation | Substituted oximes, hydrazones and olefins as neurokinin antagonists |
| US5688960A (en) | 1995-05-02 | 1997-11-18 | Schering Corporation | Substituted oximes, hydrazones and olefins useful as neurokinin antagonists |
| US6369116B1 (en) | 1995-06-02 | 2002-04-09 | Oculex Pharmaceuticals, Inc. | Composition and method for treating glaucoma |
| FR2735129B1 (fr) | 1995-06-07 | 1997-07-11 | Adir | Nouveaux derives de l'indole, de l'indazole et du benzisoxazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| ATE233734T1 (de) | 1995-06-07 | 2003-03-15 | Pfizer | Biphenyl-2-carbonsäure-tetrahydro-isochinolin-6 yl amid derivate, deren hestellung und deren verwendung als inhibitoren des mikrosomalen triglycerid-transfer-proteins und/oder der apolipoprotein b (apo b) sekretion |
| US6228861B1 (en) | 1995-11-16 | 2001-05-08 | Synaptic Pharmaceutical Corporation | Dihydropyrimidines and uses thereof |
| US6245773B1 (en) | 1996-05-16 | 2001-06-12 | Synaptic Pharmaceutical Corporation | 5-(heterocyclic alkyl)-6-aryl-dihydropyrimidines |
| WO1998023593A1 (en) | 1996-11-27 | 1998-06-04 | Pfizer Inc. | Apo b-secretion/mtp inhibitory amides |
| US5977139A (en) | 1996-12-15 | 1999-11-02 | Hoechst Marion Roussel, Inc. | Carboxysubstituted cyclic carboxamide derivatives |
| US5861417A (en) | 1996-12-19 | 1999-01-19 | Hoechst Marion Roussel, Inc. | Heterocyclic substituted pyrrolidine amide derivatives |
| US6136827A (en) | 1997-07-25 | 2000-10-24 | Merck & Co., Inc. | Cyclic amine modulations of chemokine receptor activity |
| DE69827138T2 (de) | 1997-08-11 | 2006-02-23 | Allergan, Inc., Irvine | Steriles Retinoid enthaltendes biodegradierbares Implantat mit verbesserter Biokompatibilität und Verfahren zu dessen Herstellung |
| US6020347A (en) | 1997-11-18 | 2000-02-01 | Merck & Co., Inc. | 4-substituted-4-piperidine carboxamide derivatives |
| US6303620B1 (en) | 1998-05-11 | 2001-10-16 | Novo Nordisk A/S | Compounds with growth hormone releasing properties |
| US6316445B1 (en) | 1998-05-15 | 2001-11-13 | Aventis Pharmaceuticals Inc. | Carboxy substituted acylic carboxamide derivatives |
| GT199900147A (es) | 1998-09-17 | 1999-09-06 | 1, 2, 3, 4- tetrahidroquinolinas 2-sustituidas 4-amino sustituidas. | |
| US6133291A (en) | 1998-10-16 | 2000-10-17 | Schering Corporation | N-(imidazolylalkyl)substituted cyclic amines as histamine-H3 agonists or antagonists |
| ATE262518T1 (de) * | 1999-06-03 | 2004-04-15 | Yamanouchi Pharma Co Ltd | Neuartige isoquinolin-derivate oder salze davon |
| US6331313B1 (en) | 1999-10-22 | 2001-12-18 | Oculex Pharmaceticals, Inc. | Controlled-release biocompatible ocular drug delivery implant devices and methods |
| WO2001030780A2 (en) | 1999-10-27 | 2001-05-03 | Cor Therapeutics, Inc. | Pyridyl-containing spirocyclic compounds as inhibitors of fibrinogen-dependent platelet aggregation |
| US6258833B1 (en) | 1999-12-23 | 2001-07-10 | Icos Corporation | Cyclic AMP-specific phosphodiesterase inhibitors |
| WO2002015909A1 (en) | 2000-08-23 | 2002-02-28 | Merck & Co., Inc. | Substituted piperidines as melanocortin receptor agonists |
| US6608054B2 (en) | 2001-03-20 | 2003-08-19 | Boehringer Ingelheim Pharma Kg | Pharmaceutical compositions based on anticholinergics and endothelin antagonists |
| US20020137764A1 (en) | 2000-10-31 | 2002-09-26 | Karin Drechsel | Inhalable formulation of a solution containing a tiotropium salt |
| US6620438B2 (en) | 2001-03-08 | 2003-09-16 | Boehringer Ingelheim Pharma Kg | Pharmaceutical compositions based on anticholinergics and NK1-receptor antagonists |
| US7776315B2 (en) | 2000-10-31 | 2010-08-17 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmaceutical compositions based on anticholinergics and additional active ingredients |
| ES2250504T3 (es) | 2000-11-29 | 2006-04-16 | Allergan Inc. | Prevencion del rechazo de injerto en el ojo. |
| CA2440559C (en) | 2001-03-13 | 2010-09-21 | Schering Corporation | Novel non-imidazole compounds |
| GB0118238D0 (en) | 2001-07-26 | 2001-09-19 | Smithkline Beecham Plc | Medicaments |
| TWI310034B (en) | 2001-10-02 | 2009-05-21 | Acadia Pharmaceuticais Inc | Benzimidazolidinone derivatives as muscarinic agents |
| MXPA04010172A (es) | 2002-04-18 | 2005-02-03 | Schering Corp | 1-(4-piperidinil)benzimidazolonas como antagonistas de histamina h3). |
| US7105505B2 (en) | 2002-04-18 | 2006-09-12 | Schering Corporation | Benzimidazole derivatives useful as histamine H3 antagonists |
| TW200403058A (en) * | 2002-04-19 | 2004-03-01 | Bristol Myers Squibb Co | Heterocyclo inhibitors of potassium channel function |
| US7230008B2 (en) | 2002-04-29 | 2007-06-12 | Merck & Co, Inc. | Tetrahydropyranyl cyclopentyl tetrahydropyridopyridine modulators of chemokine receptor activity |
| CA2494048A1 (en) | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | 4-hydroxyquinoline derivatives as matrix metalloproteinase inhibitors |
| CA2498272A1 (en) | 2002-09-11 | 2004-03-25 | Merck & Co., Inc. | Piperazine urea derivatives as melanocortin-4 receptor agonists |
| MXPA05003632A (es) | 2002-10-11 | 2005-06-03 | Astrazeneca Ab | Derivados de piperidina 1, 4-disustituidos y su uso como inhibidores de 11-beta-hidroesteroide deshidrogenasa humana de tipo 1 (11betahsd1). |
| NZ542680A (en) * | 2003-03-12 | 2008-08-29 | Kudos Pharm Ltd | Phthalazinone derivatives |
| EP1606280A4 (en) * | 2003-03-18 | 2008-12-24 | Merck & Co Inc | TETRAHYDROPYRANYLCYCLOPENTYL HETEROCYLAMIDE MODULATORS OF CHEMOKIN RECEPTOR ACTIVITY |
| EP1468999A1 (en) | 2003-03-20 | 2004-10-20 | MyoContract Ltd. | Substituted piperidine and piperazine derivatives as melanocortin-4 receptor modulators |
| AU2004226452B2 (en) | 2003-03-26 | 2008-07-24 | Merck Sharp & Dohme Corp. | Bicyclic piperidine derivatives as melanocortin-4 receptor agonists |
| US7268133B2 (en) | 2003-04-23 | 2007-09-11 | Pfizer, Inc. Patent Department | Cannabinoid receptor ligands and uses thereof |
| US20040259887A1 (en) | 2003-06-18 | 2004-12-23 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| BRPI0414777A (pt) | 2003-09-26 | 2006-11-21 | Actelion Pharmaceuticals Ltd | compostos, composições farmacêuticas, uso de um ou mais compostos, e, método de tratar um paciente que sofre de um distúrbio |
| GB0325745D0 (en) | 2003-11-05 | 2003-12-10 | Astrazeneca Ab | Chemical compounds |
| EP1716134A4 (en) * | 2004-02-12 | 2007-10-17 | Merck & Co Inc | HETEROCYCLIC AMINO MODULATORS OF CHEMOKIN RECEPTOR ACTIVITY |
| US7951801B2 (en) | 2004-04-09 | 2011-05-31 | Millennium Pharmaceuticals, Inc. | Beta-carbolines useful for treating inflammatory disease |
| US20060182783A1 (en) | 2004-04-30 | 2006-08-17 | Allergan, Inc. | Sustained release intraocular drug delivery systems |
| US20070059336A1 (en) | 2004-04-30 | 2007-03-15 | Allergan, Inc. | Anti-angiogenic sustained release intraocular implants and related methods |
| US7115601B2 (en) | 2004-05-18 | 2006-10-03 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| RU2417993C9 (ru) | 2004-05-18 | 2011-10-10 | Шеринг Корпорейшн | Замещенные 2-хинолилоксазолы, пригодные в качестве ингибиторов фдэ4 |
| WO2005121090A1 (en) | 2004-06-02 | 2005-12-22 | Abbott Laboratories | Substituted piperidines that have antiangiogenic activity |
| CA2573066A1 (en) | 2004-08-11 | 2006-02-16 | Janssen Pharmaceutica N.V. | Mercaptoimidazoles as ccr2 receptor antagonists |
| BRPI0516166A (pt) | 2004-09-28 | 2008-08-26 | Janssen Pharmaceutica Nv | antagonista do ccr2 de dipiperidina substituìda |
| JP2008515956A (ja) | 2004-10-12 | 2008-05-15 | ノボ ノルディスク アクティーゼルスカブ | １１β−ヒドロキシステロイドデヒドロゲナーゼ１型活性スピロ化合物 |
| FR2876692B1 (fr) * | 2004-10-19 | 2007-02-23 | Sanofi Aventis Sa | Derives de 2-amido-4-phenylthiazole, leur preparation et leur application en therapeutique |
| BRPI0518582A2 (pt) | 2004-11-24 | 2008-11-25 | Therakine Corp | implante para liberaÇço de medicamento intra-ocular |
| WO2006124748A2 (en) | 2005-05-13 | 2006-11-23 | Lexicon Genetics Incorporated | Multicyclic compounds and methods of their use |
| US7425633B2 (en) * | 2005-08-26 | 2008-09-16 | National Health Research Institutes | Pyrrolidine compounds |
| US8067415B2 (en) * | 2005-11-01 | 2011-11-29 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of CCR2 |
| CL2007002958A1 (es) | 2006-10-12 | 2008-05-09 | Epix Delaware Inc | Compuestos derivados de heteroaril-carboxamida, antagonistas del receptor de quimioquina; composicion farmaceutica; y uso para el tratamiento o prevencion de enfermedades tales como rechazo de transplante de organos, artritis reumatoidea, lupus, entr |
| WO2008045558A2 (en) | 2006-10-12 | 2008-04-17 | Epix Delaware, Inc. | Benzothiadiazine compounds and their use |
| US20100331298A1 (en) | 2007-12-10 | 2010-12-30 | Cytopathfinder, Inc. | Carboxamide Compounds and Their Use |
| EP2280766A1 (en) | 2007-12-11 | 2011-02-09 | CytoPathfinder, Inc. | Carboxamide compounds and their use as chemokine receptor agonists |
| TW201105667A (en) | 2009-05-08 | 2011-02-16 | Cytopathfinder Inc | Dihydronaphthyridinyl and related compounds for use in treating ophthalmological disorders |
-
2008
- 2008-12-11 EP EP08858495A patent/EP2280766A1/en not_active Withdrawn
- 2008-12-11 KR KR1020107015232A patent/KR20100102646A/ko not_active Ceased
- 2008-12-11 WO PCT/US2008/086388 patent/WO2009076512A1/en not_active Ceased
- 2008-12-11 CA CA2708364A patent/CA2708364A1/en not_active Abandoned
- 2008-12-11 US US12/747,109 patent/US8569282B2/en not_active Expired - Fee Related
- 2008-12-11 RU RU2010128543/04A patent/RU2010128543A/ru not_active Application Discontinuation
- 2008-12-11 BR BRPI0820701-1A patent/BRPI0820701A2/pt not_active IP Right Cessation
- 2008-12-11 AU AU2008335135A patent/AU2008335135A1/en not_active Abandoned
- 2008-12-11 CN CN2008801255852A patent/CN101925383A/zh active Pending
- 2008-12-11 JP JP2010538152A patent/JP2011506466A/ja active Pending
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