RU2010128543A - Карбоксамидные соединения и их применение в качестве агонистов хемокиновых рецепторов - Google Patents
Карбоксамидные соединения и их применение в качестве агонистов хемокиновых рецепторов Download PDFInfo
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- RU2010128543A RU2010128543A RU2010128543/04A RU2010128543A RU2010128543A RU 2010128543 A RU2010128543 A RU 2010128543A RU 2010128543/04 A RU2010128543/04 A RU 2010128543/04A RU 2010128543 A RU2010128543 A RU 2010128543A RU 2010128543 A RU2010128543 A RU 2010128543A
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- Prior art keywords
- trifluoromethyl
- alkyl
- pyrrolidin
- methyl
- carbonyl
- Prior art date
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- -1 CARBOXAMIDE COMPOUNDS Chemical class 0.000 title claims 13
- 239000000018 receptor agonist Substances 0.000 title 1
- 229940044601 receptor agonist Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 60
- 150000001875 compounds Chemical class 0.000 claims abstract 40
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 28
- 229910052736 halogen Inorganic materials 0.000 claims abstract 26
- 150000002367 halogens Chemical group 0.000 claims abstract 26
- 125000003118 aryl group Chemical group 0.000 claims abstract 24
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 23
- 239000001257 hydrogen Substances 0.000 claims abstract 22
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 21
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 9
- 125000001424 substituent group Chemical group 0.000 claims abstract 9
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract 8
- 125000004475 heteroaralkyl group Chemical group 0.000 claims abstract 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 3
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004450 alkenylene group Chemical group 0.000 claims abstract 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract 2
- 125000004419 alkynylene group Chemical group 0.000 claims abstract 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract 2
- 125000000732 arylene group Chemical group 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims abstract 2
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract 2
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 239000011593 sulfur Substances 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 claims 4
- 201000001320 Atherosclerosis Diseases 0.000 claims 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims 4
- 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 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 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 2
- 206010012442 Dermatitis contact Diseases 0.000 claims 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 206010047115 Vasculitis Diseases 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 208000010247 contact dermatitis Diseases 0.000 claims 2
- 201000001981 dermatomyositis Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 208000006454 hepatitis Diseases 0.000 claims 2
- 231100000283 hepatitis Toxicity 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 2
- 206010025135 lupus erythematosus Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 201000000306 sarcoidosis Diseases 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- AICIYIDUYNFPRY-UHFFFAOYSA-N 1,3-dihydro-2H-imidazol-2-one Chemical compound O=C1NC=CN1 AICIYIDUYNFPRY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- CKLRTGAHPHXPHJ-UHFFFAOYSA-N 2-[1-[(3-methyl-2-oxo-1,3-benzoxazol-5-yl)methyl]-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-3-yl]acetonitrile Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C(CC#N)(C1)CCN1CC1=CC=C(OC(N2C)=O)C2=C1 CKLRTGAHPHXPHJ-UHFFFAOYSA-N 0.000 claims 1
- ALCYOSUIJKKPLE-UHFFFAOYSA-N 2-[3-(methoxymethyl)-1-[(3-methyl-2-oxo-1,3-benzoxazol-5-yl)methyl]pyrrolidine-3-carbonyl]-7-(trifluoromethyl)-3,4-dihydro-1h-isoquinoline-5-carbonitrile Chemical compound C1CC(C(=CC(=C2)C(F)(F)F)C#N)=C2CN1C(=O)C1(COC)CN(CC=2C=C3N(C)C(=O)OC3=CC=2)CC1 ALCYOSUIJKKPLE-UHFFFAOYSA-N 0.000 claims 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 claims 1
- CZWWCTHQXBMHDA-UHFFFAOYSA-N 3h-1,3-thiazol-2-one Chemical compound OC1=NC=CS1 CZWWCTHQXBMHDA-UHFFFAOYSA-N 0.000 claims 1
- PXLYWESPZIWCFD-UHFFFAOYSA-N 5-[1-[3-(cyclopropylmethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]ethyl]-1,3-dimethylbenzimidazol-2-one Chemical compound C=1C=C2N(C)C(=O)N(C)C2=CC=1C(C)N(C1)CCC1(C(=O)N1CC2=CC(=CN=C2CC1)C(F)(F)F)CC1CC1 PXLYWESPZIWCFD-UHFFFAOYSA-N 0.000 claims 1
- DLTOCWLUDPHWJE-UHFFFAOYSA-N 5-[1-[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]cyclopropyl]-3-methyl-1,3-benzoxazol-2-one Chemical compound C1C(COC)(C(=O)N2CC3=CC(=CN=C3CC2)C(F)(F)F)CCN1C1(C=2C=C3N(C)C(=O)OC3=CC=2)CC1 DLTOCWLUDPHWJE-UHFFFAOYSA-N 0.000 claims 1
- FMCYGTVHKAOLAM-UHFFFAOYSA-N 5-[1-[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]ethyl]-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=2C=C3N(C)C(=O)OC3=CC=2)CC1 FMCYGTVHKAOLAM-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 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 1
- 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 1
- 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 1
- 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 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 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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
- 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 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- RFELKOVAJJRWQW-UHFFFAOYSA-N 6-[[3-benzyl-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)CC1=CC=CC=C1 RFELKOVAJJRWQW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 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 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
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- 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 1
- ICDLQSHCPNHELF-UHFFFAOYSA-N 7-[[3-(methoxymethyl)-3-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridine-6-carbonyl]pyrrolidin-1-yl]methyl]-1-methylquinoxalin-2-one Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1C(=O)C1(COC)CN(CC=2C=C3N(C)C(=O)C=NC3=CC=2)CC1 ICDLQSHCPNHELF-UHFFFAOYSA-N 0.000 claims 1
- 229910014033 C-OH Inorganic materials 0.000 claims 1
- 229910014570 C—OH Inorganic materials 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000005141 Otitis Diseases 0.000 claims 1
- 206010034277 Pemphigoid Diseases 0.000 claims 1
- 241000157312 Rhinoderma Species 0.000 claims 1
- 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 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 claims 1
- DSVKFQLIERXNHL-UHFFFAOYSA-N [1-[4-(5-fluoropyridin-2-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)CCC1C1=CC=C(F)C=N1 DSVKFQLIERXNHL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- LEHJXILMAZFEBK-UHFFFAOYSA-N [3-(cyclopropylmethyl)-1-[(3-fluoro-4-hydroxyphenyl)methyl]pyrrolidin-3-yl]-[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridin-6-yl]methanone Chemical compound C1=C(F)C(O)=CC=C1CN1CC(CC2CC2)(C(=O)N2CC3=CC(=CN=C3CC2)C(F)(F)F)CC1 LEHJXILMAZFEBK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- DOGZDSFPEVVTTB-UHFFFAOYSA-N [3-(methoxymethyl)-1-(4-pyrimidin-2-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=NC=CC=N1 DOGZDSFPEVVTTB-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
- 125000002723 alicyclic group Chemical group 0.000 claims 1
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- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000019258 ear infection Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
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- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
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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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| 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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| JP (1) | JP2011506466A (enExample) |
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| CN (1) | CN101925383A (enExample) |
| AU (1) | AU2008335135A1 (enExample) |
| BR (1) | BRPI0820701A2 (enExample) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2677291C2 (ru) * | 2012-05-31 | 2019-01-16 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Соединения тетрагидропиразолопиримидина |
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| CN102459225B (zh) * | 2009-04-16 | 2014-08-20 | 詹森药业有限公司 | Ccr2的4-氮杂环丁烷基-1-杂芳基-环己烷拮抗剂 |
| 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 |
| EP2419419B1 (en) * | 2009-04-17 | 2014-12-03 | Janssen Pharmaceutica NV | 4-azetidinyl-1-phenyl-cyclohexane antagonists of ccr2 |
| CN103717594B (zh) | 2011-06-22 | 2016-12-14 | 普渡制药公司 | 包含二羟基取代基的trpv1拮抗剂及其用途 |
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| EP4620472A3 (en) | 2022-04-28 | 2025-10-01 | 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 |
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-
2008
- 2008-12-11 AU AU2008335135A patent/AU2008335135A1/en not_active Abandoned
- 2008-12-11 JP JP2010538152A patent/JP2011506466A/ja active Pending
- 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 CN CN2008801255852A patent/CN101925383A/zh active Pending
- 2008-12-11 CA CA2708364A patent/CA2708364A1/en not_active Abandoned
- 2008-12-11 BR BRPI0820701-1A patent/BRPI0820701A2/pt not_active IP Right Cessation
- 2008-12-11 RU RU2010128543/04A patent/RU2010128543A/ru not_active Application Discontinuation
- 2008-12-11 KR KR1020107015232A patent/KR20100102646A/ko not_active Ceased
- 2008-12-11 WO PCT/US2008/086388 patent/WO2009076512A1/en not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2677291C2 (ru) * | 2012-05-31 | 2019-01-16 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Соединения тетрагидропиразолопиримидина |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009076512A1 (en) | 2009-06-18 |
| US8569282B2 (en) | 2013-10-29 |
| US20100324035A1 (en) | 2010-12-23 |
| EP2280766A1 (en) | 2011-02-09 |
| JP2011506466A (ja) | 2011-03-03 |
| AU2008335135A1 (en) | 2009-06-18 |
| KR20100102646A (ko) | 2010-09-24 |
| CN101925383A (zh) | 2010-12-22 |
| BRPI0820701A2 (pt) | 2015-06-16 |
| CA2708364A1 (en) | 2009-06-18 |
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