CA2521625A1 - Heterocyclic cyclopentyl tetrahydroisoquinoline and tetrahydropyridopyridine modulators of chemokine receptor activity - Google Patents
Heterocyclic cyclopentyl tetrahydroisoquinoline and tetrahydropyridopyridine modulators of chemokine receptor activity Download PDFInfo
- Publication number
- CA2521625A1 CA2521625A1 CA002521625A CA2521625A CA2521625A1 CA 2521625 A1 CA2521625 A1 CA 2521625A1 CA 002521625 A CA002521625 A CA 002521625A CA 2521625 A CA2521625 A CA 2521625A CA 2521625 A1 CA2521625 A1 CA 2521625A1
- Authority
- CA
- Canada
- Prior art keywords
- 6alkyl
- mmol
- substituents
- substituted
- 3alkyl
- 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.)
- Abandoned
Links
- 102000009410 Chemokine receptor Human genes 0.000 title claims abstract description 44
- 108050000299 Chemokine receptor Proteins 0.000 title claims abstract description 44
- 230000000694 effects Effects 0.000 title claims abstract description 20
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 33
- GARMUJFIZOPCTN-UHFFFAOYSA-N 1-cyclopentyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CCCC1C1C2=CC=CC=C2CCN1 GARMUJFIZOPCTN-UHFFFAOYSA-N 0.000 title description 2
- OALXTMWCXNPUKJ-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,5-naphthyridine Chemical compound C1=CN=C2CCCNC2=C1 OALXTMWCXNPUKJ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 194
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 134
- -1 -O-C1-6alkyl Chemical group 0.000 claims description 98
- 125000001424 substituent group Chemical group 0.000 claims description 87
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 62
- 125000005843 halogen group Chemical group 0.000 claims description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 125000001153 fluoro group Chemical group F* 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 230000002757 inflammatory effect Effects 0.000 claims description 14
- 229910052727 yttrium Inorganic materials 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 6
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 6
- 230000004957 immunoregulator effect Effects 0.000 claims description 6
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 3
- SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical compound C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 claims description 3
- KVRZARWOKBNZMM-UHFFFAOYSA-N 1,3-dihydro-2-benzothiophene Chemical compound C1=CC=C2CSCC2=C1 KVRZARWOKBNZMM-UHFFFAOYSA-N 0.000 claims description 2
- YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical compound C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- SIBFFZUQMOJJOI-UHFFFAOYSA-N 6h-cyclopenta[d][1,2]oxazol-3-one Chemical compound C1C=CC2=C1ON=C2O SIBFFZUQMOJJOI-UHFFFAOYSA-N 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- 102100031151 C-C chemokine receptor type 2 Human genes 0.000 abstract description 14
- 101710149815 C-C chemokine receptor type 2 Proteins 0.000 abstract description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 459
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 239
- 239000000203 mixture Substances 0.000 description 236
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 232
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 196
- 239000000243 solution Substances 0.000 description 184
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 139
- 239000000047 product Substances 0.000 description 138
- 239000000543 intermediate Substances 0.000 description 133
- 206010012812 Diffuse cutaneous mastocytosis Diseases 0.000 description 112
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 101
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 99
- 235000019439 ethyl acetate Nutrition 0.000 description 88
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 86
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 80
- 239000011541 reaction mixture Substances 0.000 description 80
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
- 238000006243 chemical reaction Methods 0.000 description 70
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 69
- 239000007787 solid Substances 0.000 description 58
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 53
- 238000005481 NMR spectroscopy Methods 0.000 description 52
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
- 235000019441 ethanol Nutrition 0.000 description 50
- 239000010410 layer Substances 0.000 description 47
- 239000012043 crude product Substances 0.000 description 46
- 238000012746 preparative thin layer chromatography Methods 0.000 description 45
- 239000012044 organic layer Substances 0.000 description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- 101150041968 CDC13 gene Proteins 0.000 description 42
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 42
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 42
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 42
- 239000012267 brine Substances 0.000 description 39
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
- 229910017974 NH40H Inorganic materials 0.000 description 38
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 36
- 229920006395 saturated elastomer Polymers 0.000 description 36
- 230000002829 reductive effect Effects 0.000 description 35
- 239000002904 solvent Substances 0.000 description 34
- 238000005160 1H NMR spectroscopy Methods 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
- 239000000741 silica gel Substances 0.000 description 27
- 229910002027 silica gel Inorganic materials 0.000 description 27
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 27
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 25
- 150000002148 esters Chemical class 0.000 description 25
- 238000003818 flash chromatography Methods 0.000 description 25
- 150000001412 amines Chemical group 0.000 description 24
- 238000000746 purification Methods 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 23
- 239000002808 molecular sieve Substances 0.000 description 23
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 23
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 23
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 22
- 210000004027 cell Anatomy 0.000 description 22
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 22
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000000725 suspension Substances 0.000 description 21
- 229940086542 triethylamine Drugs 0.000 description 21
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 19
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
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- 102100021943 C-C motif chemokine 2 Human genes 0.000 description 14
- 101710155857 C-C motif chemokine 2 Proteins 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 14
- UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 14
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- 150000003840 hydrochlorides Chemical class 0.000 description 12
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 12
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- 238000004809 thin layer chromatography Methods 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US46367303P | 2003-04-17 | 2003-04-17 | |
US60/463,673 | 2003-04-17 | ||
PCT/US2004/011463 WO2004094371A2 (en) | 2003-04-17 | 2004-04-14 | Heterocyclic cyclopentyl tetrahydroisoquinoline and tetrahydropyridopyridine modulators of chemokine receptor activity |
Publications (1)
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CA2521625A1 true CA2521625A1 (en) | 2004-11-04 |
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Family Applications (1)
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CA002521625A Abandoned CA2521625A1 (en) | 2003-04-17 | 2004-04-14 | Heterocyclic cyclopentyl tetrahydroisoquinoline and tetrahydropyridopyridine modulators of chemokine receptor activity |
Country Status (6)
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EP (1) | EP1622916A4 (ja) |
JP (1) | JP2006523704A (ja) |
CN (1) | CN100384856C (ja) |
AU (1) | AU2004232939A1 (ja) |
CA (1) | CA2521625A1 (ja) |
WO (1) | WO2004094371A2 (ja) |
Families Citing this family (22)
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WO2004094371A2 (en) * | 2003-04-17 | 2004-11-04 | Merck & Co., Inc. | Heterocyclic cyclopentyl tetrahydroisoquinoline and tetrahydropyridopyridine modulators of chemokine receptor activity |
US7598243B2 (en) | 2003-04-17 | 2009-10-06 | Merck & Co., Inc. | Heterocyclic cyclopentyl tetrahydroisoquinoline and tetrahydropyridopyridine modulators of chemokine receptor activity |
TWI350168B (en) | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
WO2007053498A1 (en) | 2005-11-01 | 2007-05-10 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of ccr2 |
US8067415B2 (en) | 2005-11-01 | 2011-11-29 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of CCR2 |
EP2010506B1 (en) | 2006-04-20 | 2010-08-04 | F. Hoffmann-La Roche AG | Diazepan derivatives modulators of chemokine receptors |
JP5497429B2 (ja) | 2007-03-07 | 2014-05-21 | 武田薬品工業株式会社 | ベンゾオキサゼピン誘導体およびその用途 |
PL2464645T3 (pl) | 2009-07-27 | 2017-12-29 | Gilead Sciences, Inc. | Skondensowane heterocykliczne związki jako modulatory kanałów jonowych |
AR080374A1 (es) | 2010-03-05 | 2012-04-04 | Sanofi Aventis | Procedimiento para la preparcion de 2-(ciclohexilmetil)-n-(2-((2s)-1-metilpirrolidin-2-il) etil)- 1,2,3,4-tetrahidroisoquinolin-7- sulfonamida |
CN103096977B (zh) | 2010-07-02 | 2017-02-15 | 吉利德科学公司 | 作为离子通道调节剂的稠杂环化合物 |
MX361350B (es) | 2011-05-10 | 2018-12-04 | Gilead Sciences Inc | Compuestos heterocíclicos fusionados como moduladores del canal de sodio. |
TW201837023A (zh) | 2011-07-01 | 2018-10-16 | 美商基利科學股份有限公司 | 作為離子通道調節劑之稠合雜環化合物 |
NO3175985T3 (ja) | 2011-07-01 | 2018-04-28 | ||
AU2016263579B2 (en) | 2015-05-21 | 2020-12-03 | Chemocentryx, Inc. | CCR2 modulators |
CN109937204B (zh) | 2016-08-01 | 2022-11-25 | 阿普廷伊克斯股份有限公司 | 螺-内酰胺nmda受体调节剂及其用途 |
AU2017306136B2 (en) | 2016-08-01 | 2021-10-21 | Aptinyx Inc. | Spiro-lactam NMDA receptor modulators and uses thereof |
CN109843889B (zh) | 2016-08-01 | 2022-03-15 | 阿普廷伊克斯股份有限公司 | 螺-内酰胺nmda调节剂和使用其的方法 |
AU2018335486B2 (en) | 2017-09-25 | 2024-07-04 | Chemocentryx, Inc. | Combination therapy using a Chemokine Receptor 2 (CCR2) antagonist and a PD-1/PD-L1 inhibitor |
MA50423A (fr) | 2018-01-08 | 2020-08-26 | Chemocentryx Inc | Procédés de traitement de tumeurs solides au moyen d'antagonistes du ccr2 |
US20190269664A1 (en) | 2018-01-08 | 2019-09-05 | Chemocentryx, Inc. | Methods of treating solid tumors with ccr2 antagonists |
AU2019215058A1 (en) * | 2018-01-31 | 2020-09-17 | Aptinyx Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
CN111056955B (zh) * | 2019-12-16 | 2021-05-25 | 中国科学院大连化学物理研究所 | 一种环己烯制备己二胺的方法 |
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EP1501803B1 (en) * | 2002-04-29 | 2008-08-13 | Merck & Co., Inc. | Tetrahydropyranyl cyclopentyl tetrahydroisoquinoline modulators of chemokine receptor activity |
WO2004094371A2 (en) * | 2003-04-17 | 2004-11-04 | Merck & Co., Inc. | Heterocyclic cyclopentyl tetrahydroisoquinoline and tetrahydropyridopyridine modulators of chemokine receptor activity |
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