ES2369320T3

ES2369320T3 - Compuestos de ftalazina y pirido(3,4-d)piridazina como antagonistas del receptor h1.

Compuestos de ftalazina y pirido(3,4-d)piridazina como antagonistas del receptor h1. Download PDF

Info

Publication number: ES2369320T3
Authority: ES; Spain
Prior art keywords: methyl; chlorophenyl; formula; pyrrolidinyl; compounds
Prior art date: 2007-10-11
Legal status : Active

Application number

ES08805231T

Other languages

English (en)

Spanish (es)

Inventor

Paul Martin Gore

Brian Edgar Looker

Panayiotis Alexandrou Procopiou

Sadie Vile

Current Assignee

Glaxo Group Ltd

Original Assignee

Glaxo Group Ltd

Priority date

2007-10-11

Filing date

2008-10-10

Publication date

2011-11-29

2008-10-10 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2011-11-29 Application granted granted Critical

2011-11-29 Publication of ES2369320T3 publication Critical patent/ES2369320T3/es

Status Active legal-status Critical Current

2028-10-10 Anticipated expiration legal-status Critical

Links

150000001875 compounds Chemical class 0.000 title claims description 277
239000005557 antagonist Substances 0.000 title description 35
239000000203 mixture Substances 0.000 claims description 145
150000003839 salts Chemical class 0.000 claims description 87
-1 (2R) -2 - {[4 - [(4-Chlorophenyl) methyl] -1-oxo-2 (1H) -phthalazinyl] methyl} -1-pyrrolidinyl Chemical group 0.000 claims description 66
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 39
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
238000011282 treatment Methods 0.000 claims description 18
206010039085 Rhinitis allergic Diseases 0.000 claims description 15
201000010105 allergic rhinitis Diseases 0.000 claims description 15
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
125000002947 alkylene group Chemical group 0.000 claims description 14
229920006395 saturated elastomer Polymers 0.000 claims description 13
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
239000000546 pharmaceutical excipient Substances 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
230000002757 inflammatory effect Effects 0.000 claims description 10
208000027866 inflammatory disease Diseases 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
208000026935 allergic disease Diseases 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
229940124597 therapeutic agent Drugs 0.000 claims description 6
238000002560 therapeutic procedure Methods 0.000 claims description 6
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 5
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
YXICCMIPIPEESR-AVKWCDSFSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(3-ethylsulfonylbutyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)C(C)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YXICCMIPIPEESR-AVKWCDSFSA-N 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
BWXFQDIMVOEZDG-OAQYLSRUSA-N 1-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]-3-propylurea Chemical compound CCCNC(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 BWXFQDIMVOEZDG-OAQYLSRUSA-N 0.000 claims description 2
NWHGDNXYTGVRTK-HXUWFJFHSA-N 1-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxopyrido[3,4-d]pyridazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]-3-propylurea Chemical compound CCCNC(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 NWHGDNXYTGVRTK-HXUWFJFHSA-N 0.000 claims description 2
TWRLBTGKEAFDGO-LJQANCHMSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(2-ethylsulfonylethyl)pyrrolidin-2-yl]methyl]pyrido[3,4-d]pyridazin-1-one Chemical compound CCS(=O)(=O)CCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 TWRLBTGKEAFDGO-LJQANCHMSA-N 0.000 claims description 2
OVMCRVJLHVRHKE-HSZRJFAPSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(2-piperidin-1-ylsulfonylethyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C[C@@H]1N(CCS(=O)(=O)N2CCCCC2)CCC1 OVMCRVJLHVRHKE-HSZRJFAPSA-N 0.000 claims description 2
DLHRVVJGYOTOOA-OAQYLSRUSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(3-ethylsulfonylpropyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)CCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 DLHRVVJGYOTOOA-OAQYLSRUSA-N 0.000 claims description 2
JETJHTYYZHIZRJ-HXUWFJFHSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(3-ethylsulfonylpropyl)pyrrolidin-2-yl]methyl]pyrido[3,4-d]pyridazin-1-one Chemical compound CCS(=O)(=O)CCCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 JETJHTYYZHIZRJ-HXUWFJFHSA-N 0.000 claims description 2
YXICCMIPIPEESR-DENIHFKCSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[(3r)-3-ethylsulfonylbutyl]pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)[C@H](C)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YXICCMIPIPEESR-DENIHFKCSA-N 0.000 claims description 2
YXICCMIPIPEESR-SIKLNZKXSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[(3s)-3-ethylsulfonylbutyl]pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)[C@@H](C)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YXICCMIPIPEESR-SIKLNZKXSA-N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
VTQRKNRZSDZHPN-HXUWFJFHSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 VTQRKNRZSDZHPN-HXUWFJFHSA-N 0.000 claims description 2
GYMAPFWCCWESFD-OAQYLSRUSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 GYMAPFWCCWESFD-OAQYLSRUSA-N 0.000 claims description 2
DKXBWIVPDBHHPD-OAQYLSRUSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 DKXBWIVPDBHHPD-OAQYLSRUSA-N 0.000 claims description 2
YOJGSGWWEUHPBC-JOCHJYFZSA-N n-[4-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]butyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NCCCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YOJGSGWWEUHPBC-JOCHJYFZSA-N 0.000 claims description 2
IJORANMSJMQSAY-HXUWFJFHSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(2-ethylsulfonylethyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 IJORANMSJMQSAY-HXUWFJFHSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 195
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 189
239000002904 solvent Substances 0.000 description 80
239000000243 solution Substances 0.000 description 65
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 50
239000000543 intermediate Substances 0.000 description 48
238000000034 method Methods 0.000 description 46
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 43
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 38
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238000006243 chemical reaction Methods 0.000 description 36
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 35
210000004027 cell Anatomy 0.000 description 35
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
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FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 27
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
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239000000725 suspension Substances 0.000 description 25
239000002585 base Substances 0.000 description 23
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238000004128 high performance liquid chromatography Methods 0.000 description 19
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
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239000000047 product Substances 0.000 description 12
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 12
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IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
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239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 10
DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 10
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QQYIEGRYADBWBV-MRXNPFEDSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C[C@@H]1NCCC1 QQYIEGRYADBWBV-MRXNPFEDSA-N 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
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239000000556 agonist Substances 0.000 description 9
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238000013421 nuclear magnetic resonance imaging Methods 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
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238000003556 assay Methods 0.000 description 8
VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 8
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
239000003921 oil Substances 0.000 description 8
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NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
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239000012453 solvate Substances 0.000 description 7
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