TW200831493A

TW200831493A - Compounds

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Info

Publication number: TW200831493A
Authority: TW; Taiwan
Prior art keywords: methyl; compound; group; alkyl; doc
Prior art date: 2006-12-20

Application number

TW096148520A

Other languages

English (en)

Chinese (zh)

Inventor

Paul Martin Gore

Michael Joachim Kranz

Brian Edgar Looker

Sadie Vile

Original Assignee

Glaxo Group Ltd

Priority date

2006-12-20

Filing date

2007-12-18

Publication date

2008-08-01

2007-12-18 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2008-08-01 Publication of TW200831493A publication Critical patent/TW200831493A/zh

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 329
150000003839 salts Chemical class 0.000 claims abstract description 99
238000000034 method Methods 0.000 claims abstract description 89
238000011282 treatment Methods 0.000 claims abstract description 18
206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 14
201000010105 allergic rhinitis Diseases 0.000 claims abstract description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 291
-1 dimethylmethyl Chemical group 0.000 claims description 151
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 119
125000000217 alkyl group Chemical group 0.000 claims description 96
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 81
125000001424 substituent group Chemical group 0.000 claims description 54
239000002585 base Substances 0.000 claims description 38
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
229910052736 halogen Inorganic materials 0.000 claims description 34
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 27
125000001041 indolyl group Chemical group 0.000 claims description 27
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 22
125000003118 aryl group Chemical group 0.000 claims description 21
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
125000000753 cycloalkyl group Chemical group 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 15
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 14
230000002757 inflammatory effect Effects 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
208000026935 allergic disease Diseases 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 10
125000000068 chlorophenyl group Chemical group 0.000 claims description 9
239000012458 free base Substances 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
208000027866 inflammatory disease Diseases 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000002877 alkyl aryl group Chemical group 0.000 claims description 7
230000002265 prevention Effects 0.000 claims description 6
125000003373 pyrazinyl group Chemical group 0.000 claims description 6
238000002560 therapeutic procedure Methods 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 5
229910052805 deuterium Inorganic materials 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
150000002923 oximes Chemical class 0.000 claims description 5
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 3
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
229910052707 ruthenium Inorganic materials 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
ZAJYRMCZVGRVKJ-UHFFFAOYSA-N 1-methoxybutan-1-amine Chemical compound CCCC(N)OC ZAJYRMCZVGRVKJ-UHFFFAOYSA-N 0.000 claims 1
ODTCWJCBBOSHSH-UHFFFAOYSA-N n-methoxybutan-1-amine Chemical compound CCCCNOC ODTCWJCBBOSHSH-UHFFFAOYSA-N 0.000 claims 1
150000003892 tartrate salts Chemical class 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 147
238000002360 preparation method Methods 0.000 abstract description 26
201000010099 disease Diseases 0.000 abstract description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 14
230000008569 process Effects 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 373
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 144
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 141
239000000543 intermediate Substances 0.000 description 110
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 108
239000002904 solvent Substances 0.000 description 99
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 91
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 88
235000019439 ethyl acetate Nutrition 0.000 description 70
239000000243 solution Substances 0.000 description 70
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 64
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 63
206010057190 Respiratory tract infections Diseases 0.000 description 55
229940086542 triethylamine Drugs 0.000 description 48
229910052757 nitrogen Inorganic materials 0.000 description 47
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
239000011541 reaction mixture Substances 0.000 description 44
239000002253 acid Substances 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
210000004027 cell Anatomy 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 34
229960001340 histamine Drugs 0.000 description 32
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 31
239000005557 antagonist Substances 0.000 description 30
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 29
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 28
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
239000000047 product Substances 0.000 description 24
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 22
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
125000002098 pyridazinyl group Chemical group 0.000 description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
102000005962 receptors Human genes 0.000 description 20
108020003175 receptors Proteins 0.000 description 20
150000001412 amines Chemical class 0.000 description 19
239000007789 gas Substances 0.000 description 19
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 19
239000000725 suspension Substances 0.000 description 19
230000001143 conditioned effect Effects 0.000 description 18
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 18
210000004369 blood Anatomy 0.000 description 16
239000008280 blood Substances 0.000 description 16
239000007787 solid Substances 0.000 description 16
238000005481 NMR spectroscopy Methods 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 15
238000004128 high performance liquid chromatography Methods 0.000 description 14
229910000027 potassium carbonate Inorganic materials 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
239000000843 powder Substances 0.000 description 13
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 12
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 12
206010036790 Productive cough Diseases 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 12
208000024794 sputum Diseases 0.000 description 12
210000003802 sputum Anatomy 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
239000000872 buffer Substances 0.000 description 11
239000012530 fluid Substances 0.000 description 11
238000010438 heat treatment Methods 0.000 description 11
239000003755 preservative agent Substances 0.000 description 11
235000019260 propionic acid Nutrition 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
239000003981 vehicle Substances 0.000 description 11
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 10
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 10
229910021529 ammonia Inorganic materials 0.000 description 10
235000011114 ammonium hydroxide Nutrition 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
210000004556 brain Anatomy 0.000 description 10
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 10
239000003112 inhibitor Substances 0.000 description 10
239000010410 layer Substances 0.000 description 10
239000002609 medium Substances 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 10
239000000523 sample Substances 0.000 description 10
239000000126 substance Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 10
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 10
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 9
102000003834 Histamine H1 Receptors Human genes 0.000 description 9
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
235000019253 formic acid Nutrition 0.000 description 9
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 9
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 9
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125000006239 protecting group Chemical group 0.000 description 9
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 8
229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 8
239000012190 activator Substances 0.000 description 8
239000000443 aerosol Substances 0.000 description 8
238000003556 assay Methods 0.000 description 8
125000001309 chloro group Chemical group Cl* 0.000 description 8
230000000694 effects Effects 0.000 description 8
125000001153 fluoro group Chemical group F* 0.000 description 8
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
239000007788 liquid Substances 0.000 description 8
239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 8
239000012453 solvate Substances 0.000 description 8
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 8
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
102000004384 Histamine H3 receptors Human genes 0.000 description 7
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229910052801 chlorine Inorganic materials 0.000 description 7
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238000010511 deprotection reaction Methods 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 7
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102100039705 Beta-2 adrenergic receptor Human genes 0.000 description 6
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OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
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101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 6
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239000000048 adrenergic agonist Substances 0.000 description 6
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
108010014499 beta-2 Adrenergic Receptors Proteins 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
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238000001938 differential scanning calorimetry curve Methods 0.000 description 6
229960002714 fluticasone Drugs 0.000 description 6
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239000006260 foam Substances 0.000 description 6
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210000003928 nasal cavity Anatomy 0.000 description 6
238000000634 powder X-ray diffraction Methods 0.000 description 6
125000004076 pyridyl group Chemical group 0.000 description 6
125000000719 pyrrolidinyl group Chemical group 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
229940124597 therapeutic agent Drugs 0.000 description 6
210000001519 tissue Anatomy 0.000 description 6
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206010061218 Inflammation Diseases 0.000 description 5
102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 5
108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 5
238000005804 alkylation reaction Methods 0.000 description 5
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