JP2011506466A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 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 1
- 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 1
- 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 1
- PUEDSWKAOHTFDD-UHFFFAOYSA-N 6-[1-[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]ethyl]-1-methyl-3h-indol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(C(C)C=2C=C3N(C)C(=O)CC3=CC=2)CC1 PUEDSWKAOHTFDD-UHFFFAOYSA-N 0.000 claims 1
- KDMYWUDMXFRDAA-UHFFFAOYSA-N 6-[3-(methoxymethyl)-1-[(3-methyl-2-oxo-1,3-benzoxazol-5-yl)methyl]pyrrolidine-3-carbonyl]-7,8-dihydro-5h-1,6-naphthyridine-3-carbonitrile Chemical compound C1CC2=NC=C(C#N)C=C2CN1C(=O)C1(COC)CN(CC=2C=C3N(C)C(=O)OC3=CC=2)CC1 KDMYWUDMXFRDAA-UHFFFAOYSA-N 0.000 claims 1
- XBICIUXGZNQOOH-UHFFFAOYSA-N 6-[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]-1-methyl-7,8-dihydro-6h-cyclopenta[e][1,3]benzoxazol-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(C2C3=C(C=4N(C)C(=O)OC=4C=C3)CC2)CC1 XBICIUXGZNQOOH-UHFFFAOYSA-N 0.000 claims 1
- MQRYXWFYGALVHE-XMMPIXPASA-N 6-[[(3r)-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-XMMPIXPASA-N 0.000 claims 1
- 241000721454 Pemphigus Species 0.000 claims 1
- VEOMTPBCTASTBP-UHFFFAOYSA-N [1-(4-hydroxy-4-pyrimidin-5-ylcyclohexyl)-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=CN=CN=C1 VEOMTPBCTASTBP-UHFFFAOYSA-N 0.000 claims 1
- LJJFNVXBPXYBDE-UHFFFAOYSA-N [3-(methoxymethyl)-1-(4-pyrimidin-5-ylcyclohexyl)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=CN=CN=C1 LJJFNVXBPXYBDE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000004060 metabolic process Effects 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 10
- 238000000034 method Methods 0.000 description 3
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- 208000006673 asthma Diseases 0.000 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- NQTKKLPVDZGIDL-UHFFFAOYSA-N 7-[1-[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]ethyl]-1-methylquinoxalin-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(C(C)C=2C=C3N(C)C(=O)C=NC3=CC=2)CC1 NQTKKLPVDZGIDL-UHFFFAOYSA-N 0.000 description 1
- ACQIEOAKFTWLGQ-UHFFFAOYSA-N COCC1(CN=C2CCN(CC2=C1)C(=O)C3CNCC3C4(CCCCC4OC)C5=CN=CC=C5)C(F)(F)F Chemical compound COCC1(CN=C2CCN(CC2=C1)C(=O)C3CNCC3C4(CCCCC4OC)C5=CN=CC=C5)C(F)(F)F ACQIEOAKFTWLGQ-UHFFFAOYSA-N 0.000 description 1
- 102000009410 Chemokine receptor Human genes 0.000 description 1
- 108050000299 Chemokine receptor Proteins 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 201000009273 Endometriosis Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000011200 Kawasaki disease Diseases 0.000 description 1
- 206010027260 Meningitis viral Diseases 0.000 description 1
- 208000009525 Myocarditis Diseases 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 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 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 208000001725 mucocutaneous lymph node syndrome Diseases 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 201000010044 viral meningitis Diseases 0.000 description 1
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 JP2011506466A (ja) | 2011-03-03 |
| JP2011506466A5 true JP2011506466A5 (https=) | 2012-02-02 |
Family
ID=40352365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010538152A Pending JP2011506466A (ja) | 2007-12-11 | 2008-12-11 | 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 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8569282B2 (https=) |
| EP (1) | EP2280766A1 (https=) |
| JP (1) | JP2011506466A (https=) |
| KR (1) | KR20100102646A (https=) |
| CN (1) | CN101925383A (https=) |
| AU (1) | AU2008335135A1 (https=) |
| BR (1) | BRPI0820701A2 (https=) |
| CA (1) | CA2708364A1 (https=) |
| RU (1) | RU2010128543A (https=) |
| WO (1) | WO2009076512A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2685266C (en) | 2007-04-27 | 2014-01-28 | Purdue Pharma L.P. | Trpv1 antagonists and uses thereof for the treatment of prevention of pain, ui and ulcer, ibd, or ibs in an animal |
| BRPI0820701A2 (pt) | 2007-12-11 | 2015-06-16 | Cytopathfinder Inc | Composto de carboxamida e seu uso como agonistas do receptor de quimiocina |
| TW201105649A (en) * | 2009-04-16 | 2011-02-16 | Janssen Pharmaceutica Nv | 4-azetidinyl-1-heteroaryl-cyclohexane antagonists of CCR2 |
| EP2419419B1 (en) * | 2009-04-17 | 2014-12-03 | Janssen Pharmaceutica NV | 4-azetidinyl-1-phenyl-cyclohexane antagonists of ccr2 |
| CN102459226B (zh) * | 2009-04-17 | 2014-09-17 | 詹森药业有限公司 | Ccr2的4-氮杂环丁烷基-1-杂原子连接的-环己烷拮抗剂 |
| PE20141531A1 (es) | 2011-06-22 | 2014-10-23 | Purdue Pharma Lp | Antagonistas de trpv1 que incluyen sustituyentes dihidroxi y sus usos |
| 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 |
| CN120081844A (zh) | 2022-01-21 | 2025-06-03 | 新特拉有限公司 | Parp1抑制剂及其用途 |
| AU2023235233A1 (en) | 2022-03-14 | 2024-09-12 | Slap Pharmaceuticals Llc | Multicyclic compounds |
| AU2023259236B2 (en) | 2022-04-28 | 2025-01-09 | Xinthera, Inc. | Tricyclic parp1 inhibitors and uses thereof |
| 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 |
| WO2025131049A1 (en) * | 2023-12-21 | 2025-06-26 | Ignis Therapeutics (Suzhou) Limited | Dihydro-pyrrolo-pyridine derivatives and uses thereof |
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 (https=) | 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 |
| US5102915A (en) | 1990-03-22 | 1992-04-07 | Merrell Dow Pharmaceuticals Inc. | Cyclopropyl squalene derivatives and their use as inhibitors of cholesterol synthesis |
| US5051534A (en) | 1990-03-22 | 1991-09-24 | Merrell Dow Pharmaceuticals Inc. | Novel cyclopropyl squalene derivatives and their use as inhibitors of cholesterol synthesis |
| US5011859A (en) | 1990-03-30 | 1991-04-30 | Merrell Dow Pharmaceuticals Inc. | Di- and tetra-fluoro analogs of squalene as inhibitors of squalene epoxidase |
| US5064864A (en) | 1990-03-30 | 1991-11-12 | 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 |
| ZA915659B (en) | 1990-07-25 | 1992-05-27 | Merrell Dow Pharma | Novel piperidyl ethers and thioethers as inhibitors of cholesterol biosynthesis |
| 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 |
| MX9703518A (es) | 1994-11-16 | 1997-08-30 | Synaptic Pharma Corp | Dihidropirimidinas y usos de las mismas. |
| US6268369B1 (en) | 1994-11-16 | 2001-07-31 | Synaptic Pharmaceutical Corporation | 5-(heterocyclic alkyl)-6-aryl-dihydropyrimidines |
| US5510379A (en) | 1994-12-19 | 1996-04-23 | Warner-Lambert Company | Sulfonate ACAT inhibitors |
| US5688960A (en) | 1995-05-02 | 1997-11-18 | Schering Corporation | Substituted oximes, hydrazones and olefins useful as neurokinin antagonists |
| US5696267A (en) | 1995-05-02 | 1997-12-09 | Schering Corporation | Substituted oximes, hydrazones and olefins as neurokinin antagonists |
| US6369116B1 (en) | 1995-06-02 | 2002-04-09 | Oculex Pharmaceuticals, Inc. | Composition and method for treating glaucoma |
| DK0832069T3 (da) | 1995-06-07 | 2003-04-22 | Pfizer | Biphenyl-2-carboxylsyre-tetrahydroisoquinolin-6-ylamidderivater, deres fremstilling og deres anvendelse som inhibitorer af sekretion af mikrosomalt triglyceridoverførselsprotein og/eller apolipoprotein B (Apo B) |
| 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 |
| 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 |
| EA001539B1 (ru) | 1996-11-27 | 2001-04-23 | Пфайзер Инк. | Амиды, ингибирующие секрецию аполипопротеина в (аро в) и/или микросомного протеина переноса триглицеридов (мтр) |
| 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 |
| JP2001513369A (ja) | 1997-08-11 | 2001-09-04 | アラーガン・セイルズ・インコーポレイテッド | 改善された生物適合性を有する無菌の生物侵食性の移植デバイスおよび方法 |
| 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 |
| DE60009287T2 (de) | 1999-06-03 | 2005-02-17 | Yamanouchi Pharmaceutical 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 |
| ATE250604T1 (de) | 1999-10-27 | 2003-10-15 | Millennium Pharm Inc | Pyridyl enthaltende spirocyclische verbindungen als inhibitoren der fibrinogen-abhängigen blutplättchen aggregation |
| US6258833B1 (en) | 1999-12-23 | 2001-07-10 | Icos Corporation | Cyclic AMP-specific phosphodiesterase inhibitors |
| JP2004506687A (ja) | 2000-08-23 | 2004-03-04 | メルク エンド カムパニー インコーポレーテッド | メラノコルチン受容体作働薬としての置換ピペリジン類 |
| US6620438B2 (en) | 2001-03-08 | 2003-09-16 | Boehringer Ingelheim Pharma Kg | Pharmaceutical compositions based on anticholinergics and NK1-receptor antagonists |
| US20020137764A1 (en) | 2000-10-31 | 2002-09-26 | Karin Drechsel | Inhalable formulation of a solution containing a tiotropium salt |
| US7776315B2 (en) | 2000-10-31 | 2010-08-17 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmaceutical compositions based on anticholinergics and additional active ingredients |
| US6608054B2 (en) | 2001-03-20 | 2003-08-19 | Boehringer Ingelheim Pharma Kg | Pharmaceutical compositions based on anticholinergics and endothelin antagonists |
| EP1339438B1 (en) | 2000-11-29 | 2005-10-19 | Allergan Inc. | Preventing transplant rejection in the eye |
| MXPA03008356A (es) | 2001-03-13 | 2003-12-11 | Schering Corp | Compuestos del tipo no imidazol como antagonistas de histamina h3. |
| GB0118238D0 (en) | 2001-07-26 | 2001-09-19 | Smithkline Beecham Plc | Medicaments |
| BR0213611A (pt) | 2001-10-02 | 2005-12-20 | Acadia Pharm Inc | Composto, composição farmacêutica, seus usos, método para aumentar a atividade de um receptor colinérgico, métodos para tratamento ou prevenção de distúrbio mental, dor, pressão intraocular aumentada e progressão ou formação de placas amilóides |
| US7105505B2 (en) | 2002-04-18 | 2006-09-12 | Schering Corporation | Benzimidazole derivatives useful as histamine H3 antagonists |
| US7220735B2 (en) | 2002-04-18 | 2007-05-22 | Schering Corporation | Benzimidazolone 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 |
| WO2004014377A1 (en) | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | 4-hydroxyquinoline derivatives as matrix metalloproteinase inhibitors |
| WO2004024720A1 (en) | 2002-09-11 | 2004-03-25 | Merck & Co., Inc. | Piperazine urea derivatives as melanocortin-4 receptor agonists |
| WO2004033427A1 (en) | 2002-10-11 | 2004-04-22 | Astrazeneca Ab | 1,4-disubstituted piperidine derivatives and their use as 11-betahsd1 inhibitors |
| PL1633724T3 (pl) * | 2003-03-12 | 2011-10-31 | Kudos Pharm Ltd | Pochodne ftalazynonu |
| CN1826334A (zh) * | 2003-03-18 | 2006-08-30 | 麦克公司 | 趋化因子受体活性的四氢吡喃基环戊基杂环酰胺调节剂 |
| EP1468999A1 (en) | 2003-03-20 | 2004-10-20 | MyoContract Ltd. | Substituted piperidine and piperazine derivatives as melanocortin-4 receptor modulators |
| CN1764458A (zh) | 2003-03-26 | 2006-04-26 | 麦克公司 | 作为黑皮质素－4受体激动剂的双环哌啶衍生物 |
| 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 |
| AU2004275488A1 (en) | 2003-09-26 | 2005-04-07 | Actelion Pharmaceuticals Ltd | Pyridine derivatives and use thereof as urotensin II antagonists |
| GB0325745D0 (en) | 2003-11-05 | 2003-12-10 | Astrazeneca Ab | Chemical compounds |
| JP2007522219A (ja) * | 2004-02-12 | 2007-08-09 | メルク エンド カムパニー インコーポレーテッド | ケモカイン受容体活性のアミノ複素環式調節物質 |
| BRPI0509660A (pt) | 2004-04-09 | 2007-10-09 | Millennium Pharm Inc | compostos de beta-carbolina de utilidade no tratamento de doenças inflamatórias |
| 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 |
| CA2565599C (en) | 2004-05-18 | 2012-07-31 | Schering Corporation | Substituted 2-quinolyl-oxazoles useful as pde4 inhibitors |
| US7115601B2 (en) | 2004-05-18 | 2006-10-03 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| WO2005121090A1 (en) | 2004-06-02 | 2005-12-22 | Abbott Laboratories | Substituted piperidines that have antiangiogenic activity |
| EP1778646A1 (en) | 2004-08-11 | 2007-05-02 | Janssen Pharmaceutica N.V. | Mercaptoimidazoles as ccr2 receptor antagonists |
| CN101065374A (zh) | 2004-09-28 | 2007-10-31 | 詹森药业有限公司 | 取代的二哌啶化学引诱物细胞因子受体2拮抗剂 |
| EP1802623A1 (en) | 2004-10-12 | 2007-07-04 | Novo Nordisk A/S | 11beta-hydroxysteroid dehydrogenase type 1 active spiro compounds |
| FR2876692B1 (fr) * | 2004-10-19 | 2007-02-23 | Sanofi Aventis Sa | Derives de 2-amido-4-phenylthiazole, leur preparation et leur application en therapeutique |
| MX2007006214A (es) | 2004-11-24 | 2008-04-16 | Therakine Ltd | Un implante para suministro de farmaco intraocular. |
| ES2434467T3 (es) | 2005-05-13 | 2013-12-16 | Lexicon Pharmaceuticals, Inc. | Compuestos multicíclicos y métodos para su uso |
| US7425633B2 (en) * | 2005-08-26 | 2008-09-16 | National Health Research Institutes | Pyrrolidine compounds |
| WO2007053499A2 (en) * | 2005-11-01 | 2007-05-10 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of ccr2 |
| AR063275A1 (es) | 2006-10-12 | 2009-01-14 | Epix Delaware Inc | Compuestos de carboxamida, una composicion farmaceutica que los comprende y su uso en la preparacion de un medicamento para el tratamiento de enfermedades mediadas por la activacion de ccr2. |
| US20100184749A1 (en) | 2006-10-12 | 2010-07-22 | EPIX Delaware ,Inc. | Benzothiadiazine compounds and their use |
| WO2009076404A1 (en) | 2007-12-10 | 2009-06-18 | Epix Delaware, Inc. | Carboxamide compounds and their use as antagonists of the chemokine ccr2 receptor |
| BRPI0820701A2 (pt) | 2007-12-11 | 2015-06-16 | Cytopathfinder Inc | Composto de carboxamida e seu uso como agonistas do receptor de quimiocina |
| WO2010129843A1 (en) | 2009-05-08 | 2010-11-11 | Cytopathfinder, Inc. | Dihydronaphthyridinyl and related compounds for use in treating ophthalmological disorders |
-
2008
- 2008-12-11 BR BRPI0820701-1A patent/BRPI0820701A2/pt not_active IP Right Cessation
- 2008-12-11 US US12/747,109 patent/US8569282B2/en not_active Expired - Fee Related
- 2008-12-11 CN CN2008801255852A patent/CN101925383A/zh active Pending
- 2008-12-11 KR KR1020107015232A patent/KR20100102646A/ko not_active Ceased
- 2008-12-11 RU RU2010128543/04A patent/RU2010128543A/ru not_active Application Discontinuation
- 2008-12-11 WO PCT/US2008/086388 patent/WO2009076512A1/en not_active Ceased
- 2008-12-11 AU AU2008335135A patent/AU2008335135A1/en not_active Abandoned
- 2008-12-11 CA CA2708364A patent/CA2708364A1/en not_active Abandoned
- 2008-12-11 JP JP2010538152A patent/JP2011506466A/ja active Pending
- 2008-12-11 EP EP08858495A patent/EP2280766A1/en not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2011506466A5 (https=) | ||
| RU2010128543A (ru) | Карбоксамидные соединения и их применение в качестве агонистов хемокиновых рецепторов | |
| KR101954044B1 (ko) | 피리돈 및 아자-피리돈 화합물 및 사용 방법 | |
| JP6117235B2 (ja) | Ｐｉ３ｋの活性または機能の阻害剤の使用 | |
| AU2009210517B2 (en) | Pyrido [4, 3-D] pyrimidinone derivatives as kinase inhibitors | |
| JP2025535046A (ja) | Ｋｒａｓ ｇ１２ｃ変異タンパク質の複素環阻害剤及びその使用 | |
| DK2096919T3 (en) | SUBSTITUTED 2,3-DIHYDROIMIDAZO [1,2-C] QUINAZOLINE DERIVATIVES USED FOR TREATING HYPERPROLIFERATIVE DISORDERS AND DISEASES ASSOCIATED WITH ANGIOGENESIS | |
| JP6435323B2 (ja) | 炎症性障害の治療のための新規化合物及びその医薬組成物 | |
| JP5903499B2 (ja) | ジヒドロ−ベンゾ−オキサジンおよびジヒドロ−ピリド−オキサジン誘導体 | |
| JP2025535045A (ja) | Ｋｒａｓ ｇ１２ｃ変異タンパク質の複素環阻害剤及びその使用 | |
| RU2020112759A (ru) | Гетероциклические соединения в качестве ингибиторов PAD | |
| RU2008141761A (ru) | ИНГИБИТОРЫ с-МЕТ ПРОТЕИНКИНАЗЫ | |
| JP2013508404A5 (https=) | ||
| ES2902365T3 (es) | Compuestos de furanopirimidina sustituidos como inhibidores de PDE1 | |
| JP2020531498A5 (https=) | ||
| EA025520B1 (ru) | N-(ГЕТЕРО)АРИЛПИРРОЛИДИНОВЫЕ ПРОИЗВОДНЫЕ ПИРАЗОЛ-4-ИЛ-ПИРРОЛО[2,3-d]ПИРИМИДИНОВ И ПИРРОЛ-3-ИЛ-ПИРРОЛО[2,3-d]ПИРИМИДИНОВ В КАЧЕСТВЕ ИНГИБИТОРОВ ЯНУС-КИНАЗЫ | |
| JP2019516757A (ja) | Ｃｂｐ／ｅｐ３００の複素環式インヒビターおよびがんの処置におけるそれらの使用 | |
| EP3224258A1 (en) | 4,5,6,7-tetrahydro-1 h-pyrazolo[4,3-c]pyridin-3-amine compounds as cbp and/or ep300 inhibitors | |
| JP2016500073A5 (https=) | ||
| JP2011500774A5 (https=) | ||
| KR20150002573A (ko) | 벤조티아졸-6-일 아세트산 유도체 및 ｈｉｖ 감염을 치료하기 위한 이의 용도 | |
| JP2012532931A5 (https=) | ||
| JP2015522002A5 (https=) | ||
| AU2005295734A1 (en) | Methods of treating vascular injuries | |
| JP2009538896A5 (https=) |