AP333A - Phenyl-substituted pyridyl aliphatic compounds for treating leukotriene-related diseases. - Google Patents

Phenyl-substituted pyridyl aliphatic compounds for treating leukotriene-related diseases. Download PDF

Info

Publication number: AP333A
Authority: AP; ARIPO
Prior art keywords: methoxyphenyl; carboxyethenyl; phenyl; thia; ethyl
Prior art date: 1991-09-19

Application number

APAP/P/1992/000428A

Other languages

English (en)

Other versions

AP9200428A0 (en

Inventor

Pamela Anne Chambers

Robert A Daines

Dalia R Jakas

William D Kingsbury

Israel Pendrak (Nmi)

Original Assignee

Smithkline Beecham Corp

Priority date (The priority date 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 date listed.)

1991-09-19

Filing date

1992-09-17

Publication date

1994-04-25

1992-09-17 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

1992-10-31 Publication of AP9200428A0 publication Critical patent/AP9200428A0/xx

1994-04-25 Application granted granted Critical

1994-04-25 Publication of AP333A publication Critical patent/AP333A/en

Links

-1 Phenyl-substituted pyridyl aliphatic compounds Chemical class 0.000 title claims description 51
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 14
201000010099 disease Diseases 0.000 title description 13
150000002617 leukotrienes Chemical class 0.000 title description 12
239000002253 acid Substances 0.000 claims abstract description 91
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 153
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 117
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 112
150000001875 compounds Chemical class 0.000 claims description 93
125000001931 aliphatic group Chemical group 0.000 claims description 91
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 74
229910003002 lithium salt Inorganic materials 0.000 claims description 73
159000000002 lithium salts Chemical class 0.000 claims description 73
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 71
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 56
125000004076 pyridyl group Chemical group 0.000 claims description 56
SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 claims description 55
239000005711 Benzoic acid Substances 0.000 claims description 50
235000010233 benzoic acid Nutrition 0.000 claims description 50
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 45
238000000034 method Methods 0.000 claims description 35
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 33
125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 33
125000003545 alkoxy group Chemical group 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 25
150000001204 N-oxides Chemical class 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
125000001153 fluoro group Chemical group F* 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 11
150000003254 radicals Chemical class 0.000 claims description 11
150000001408 amides Chemical group 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
201000004681 Psoriasis Diseases 0.000 claims description 7
SOKBUAQWSPPGGI-UHFFFAOYSA-N trifluoromethanesulfonamide Chemical compound NS(=O)(=O)C(F)(F)F.NS(=O)(=O)C(F)(F)F SOKBUAQWSPPGGI-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000002431 hydrogen Chemical group 0.000 claims description 5
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 5
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000004953 trihalomethyl group Chemical group 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
229940124530 sulfonamide Drugs 0.000 claims description 3
150000003456 sulfonamides Chemical group 0.000 claims description 3
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 3
150000003536 tetrazoles Chemical class 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
125000005605 benzo group Chemical group 0.000 claims 1
229960003424 phenylacetic acid Drugs 0.000 claims 1
239000003279 phenylacetic acid Substances 0.000 claims 1
150000001412 amines Chemical class 0.000 abstract description 6
150000007513 acids Chemical class 0.000 abstract description 2
239000003199 leukotriene receptor blocking agent Substances 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 224
238000006243 chemical reaction Methods 0.000 description 162
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 146
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 139
150000001336 alkenes Chemical class 0.000 description 129
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 128
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 125
125000003118 aryl group Chemical group 0.000 description 109
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 96
235000019439 ethyl acetate Nutrition 0.000 description 95
238000005481 NMR spectroscopy Methods 0.000 description 93
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 84
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 84
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 70
239000000377 silicon dioxide Substances 0.000 description 69
239000007787 solid Substances 0.000 description 69
239000000243 solution Substances 0.000 description 68
239000012300 argon atmosphere Substances 0.000 description 62
239000000047 product Substances 0.000 description 61
125000001743 benzylic group Chemical group 0.000 description 60
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 55
239000012267 brine Substances 0.000 description 54
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 54
239000002904 solvent Substances 0.000 description 52
238000000746 purification Methods 0.000 description 48
238000003818 flash chromatography Methods 0.000 description 47
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 42
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 42
229910052943 magnesium sulfate Inorganic materials 0.000 description 42
238000001816 cooling Methods 0.000 description 40
239000000203 mixture Substances 0.000 description 40
235000019341 magnesium sulphate Nutrition 0.000 description 39
150000004702 methyl esters Chemical class 0.000 description 37
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 35
229960004365 benzoic acid Drugs 0.000 description 34
229940093499 ethyl acetate Drugs 0.000 description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 33
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
238000004458 analytical method Methods 0.000 description 28
210000004027 cell Anatomy 0.000 description 27
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
239000003921 oil Substances 0.000 description 22
235000019198 oils Nutrition 0.000 description 22
238000003820 Medium-pressure liquid chromatography Methods 0.000 description 20
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 20
238000004108 freeze drying Methods 0.000 description 20
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 19
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
239000011734 sodium Substances 0.000 description 17
229910052708 sodium Inorganic materials 0.000 description 17
229940050390 benzoate Drugs 0.000 description 16
229910002092 carbon dioxide Inorganic materials 0.000 description 16
239000000284 extract Substances 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
238000007792 addition Methods 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
239000012298 atmosphere Substances 0.000 description 13
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
229910052786 argon Inorganic materials 0.000 description 11
239000012230 colorless oil Substances 0.000 description 11
239000004615 ingredient Substances 0.000 description 11
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
150000001299 aldehydes Chemical class 0.000 description 10
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
239000012044 organic layer Substances 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 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
239000000872 buffer Substances 0.000 description 9
238000009472 formulation Methods 0.000 description 9
238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 9
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 8
239000007832 Na2SO4 Substances 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
239000000543 intermediate Substances 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
238000003756 stirring Methods 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 8
NAPXLSHLNWJHJH-CSKARUKUSA-N (e)-4-[6-(hydroxymethyl)-3-[8-(4-methoxyphenyl)octoxy]pyridin-2-yl]but-3-enoic acid Chemical compound C1=CC(OC)=CC=C1CCCCCCCCOC1=CC=C(CO)N=C1\C=C\CC(O)=O NAPXLSHLNWJHJH-CSKARUKUSA-N 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
239000005557 antagonist Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 6
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
YFHXZQPUBCBNIP-UHFFFAOYSA-N fura-2 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=3OC(=CC=3C=2)C=2OC(=CN=2)C(O)=O)N(CC(O)=O)CC(O)=O)=C1 YFHXZQPUBCBNIP-UHFFFAOYSA-N 0.000 description 6
239000007788 liquid Substances 0.000 description 6
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
239000007800 oxidant agent Substances 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
239000003826 tablet Substances 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
230000027455 binding Effects 0.000 description 5
239000012043 crude product Substances 0.000 description 5
YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 5
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
239000008187 granular material Substances 0.000 description 5
229910052744 lithium Inorganic materials 0.000 description 5
238000002156 mixing Methods 0.000 description 5
235000019271 petrolatum Nutrition 0.000 description 5
235000015320 potassium carbonate Nutrition 0.000 description 5
230000008569 process Effects 0.000 description 5
150000003462 sulfoxides Chemical class 0.000 description 5
150000003568 thioethers Chemical class 0.000 description 5
RDQQJPSVWVFAJK-UHFFFAOYSA-N 3-hydroxy-6-methylpyridine-2-carbaldehyde Chemical compound CC1=CC=C(O)C(C=O)=N1 RDQQJPSVWVFAJK-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
CLMVSPFUPYYSAI-UHFFFAOYSA-N 8-(4-methoxyphenyl)octan-1-ol Chemical compound COC1=CC=C(CCCCCCCCO)C=C1 CLMVSPFUPYYSAI-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
102000018697 Membrane Proteins Human genes 0.000 description 4
108010052285 Membrane Proteins Proteins 0.000 description 4
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
239000003937 drug carrier Substances 0.000 description 4
239000002024 ethyl acetate extract Substances 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 4
239000002480 mineral oil Substances 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
ATCNYMVVGBLQMQ-UHFFFAOYSA-N oct-7-yn-1-ol Chemical compound OCCCCCCC#C ATCNYMVVGBLQMQ-UHFFFAOYSA-N 0.000 description 4
239000002674 ointment Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000008024 pharmaceutical diluent Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
150000003457 sulfones Chemical class 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000011282 treatment Methods 0.000 description 4
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
229920002554 vinyl polymer Polymers 0.000 description 4
SYSZENVIJHPFNL-UHFFFAOYSA-N (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform B (protein) Chemical compound COC1=CC=C(I)C=C1 SYSZENVIJHPFNL-UHFFFAOYSA-N 0.000 description 3
XASXKSQAAHFMNH-UEIGIMKUSA-N (e)-4-[6-(chloromethyl)-3-dodecoxypyridin-2-yl]but-3-enoic acid;hydrochloride Chemical compound Cl.CCCCCCCCCCCCOC1=CC=C(CCl)N=C1\C=C\CC(O)=O XASXKSQAAHFMNH-UEIGIMKUSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 3
229940018563 3-aminophenol Drugs 0.000 description 3
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Pulmonology (AREA)
Immunology (AREA)
Dermatology (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Thiazole And Isothizaole Compounds (AREA)
Discharge Lamps And Accessories Thereof (AREA)
Cathode-Ray Tubes And Fluorescent Screens For Display (AREA)

APAP/P/1992/000428A 1991-09-19 1992-09-17 Phenyl-substituted pyridyl aliphatic compounds for treating leukotriene-related diseases. AP333A (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US76271091A	1991-09-19	1991-09-19
US79093191A	1991-11-12	1991-11-12
US80959391A	1991-12-18	1991-12-18
US93286992A	1992-08-20	1992-08-20
CN93103596A CN1092409A (zh)	1991-09-19	1993-03-19	用于治疗白三烯有关的疾病的化合物

Publications (2)

Publication Number	Publication Date
AP9200428A0 AP9200428A0 (en)	1992-10-31
AP333A true AP333A (en)	1994-04-25

Family

ID=36809157

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1992/000428A AP333A (en)	1991-09-19	1992-09-17	Phenyl-substituted pyridyl aliphatic compounds for treating leukotriene-related diseases.

Country Status (12)

Country	Link
EP (1)	EP0604529A1 (fr)
JP (1)	JPH06510786A (fr)
CN (1)	CN1092409A (fr)
AP (1)	AP333A (fr)
AU (1)	AU2573592A (fr)
CA (1)	CA2119467A1 (fr)
IL (1)	IL103205A0 (fr)
MA (1)	MA22649A1 (fr)
MX (1)	MX9205358A (fr)
NZ (1)	NZ244371A (fr)
PT (1)	PT100881A (fr)
WO (1)	WO1993006085A1 (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ254473A (en) *	1992-06-30	1996-11-26	Smithkline Beecham Corp	Preparation of phenylthiomethylpyridinylalkenoates
GB9313145D0 (en) *	1993-06-25	1993-08-11	Smithkline Beecham Plc	Process
IL115420A0 (en)	1994-09-26	1995-12-31	Zeneca Ltd	Aminoheterocyclic derivatives
DK0812194T3 (da) *	1995-03-02	2000-12-18	Smithkline Beecham Corp	Fremgangsmåde til behandling af atopisk dermatitis og kontaktdermatitis
GB9508137D0 (en) *	1995-04-21	1995-06-07	Smithkline Beecham Plc	Formulation
GB9602166D0 (en)	1996-02-02	1996-04-03	Zeneca Ltd	Aminoheterocyclic derivatives
US6313127B1 (en)	1996-02-02	2001-11-06	Zeneca Limited	Heterocyclic compounds useful as pharmaceutical agents
US5929096A (en) *	1996-02-29	1999-07-27	Smithkline Beecham Corporation	Method for treating atopic dermatitis and contact dermatitis
CN1228087A (zh) *	1996-08-14	1999-09-08	曾尼卡有限公司	取代的嘧啶衍生物和它们的药物用途
AU4557397A (en) *	1996-09-26	1998-04-17	Novartis Ag	Aryl-substituted acrylamides with leukotriene b4 (ltb-4) receptor antagonist activity
UA56197C2 (uk)	1996-11-08	2003-05-15	Зенека Лімітед	Гетероциклічні похідні
JP2001511798A (ja)	1997-02-13	2001-08-14	ゼネカ・リミテッド	オキシド−スクアレンシクラーゼ抑制剤として有用な複素環化合物
DE69815509T2 (de)	1997-02-13	2004-05-13	Astrazeneca Ab	Heterozyklische verbindungen die als oxido-squalen-zyklase-inhibitoren anwendung finden
GB9715895D0 (en)	1997-07-29	1997-10-01	Zeneca Ltd	Heterocyclic compounds
GB9902989D0 (en)	1999-02-11	1999-03-31	Zeneca Ltd	Heterocyclic derivatives

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4056619A (en) *	1975-09-08	1977-11-01	Warner-Lambert Company	1-Substituted-2-(2-pyridinyl)ethanone N-oxides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5004743A (en) *	1987-11-25	1991-04-02	Merck Frosst Canada, Inc.	Pyridyl styrene dialkanoic acids as anti-leukotriene agents
JPH07116150B2 (ja) *	1990-06-07	1995-12-13	スミスクライン・ビーチャム・コーポレイション	安息香酸誘導体

1992
- 1992-09-01 JP JP5506069A patent/JPH06510786A/ja active Pending
- 1992-09-01 AU AU25735/92A patent/AU2573592A/en not_active Abandoned
- 1992-09-01 WO PCT/US1992/007466 patent/WO1993006085A1/fr not_active Ceased
- 1992-09-01 CA CA002119467A patent/CA2119467A1/fr not_active Abandoned
- 1992-09-01 EP EP92920043A patent/EP0604529A1/fr not_active Withdrawn
- 1992-09-08 MA MA22940A patent/MA22649A1/fr unknown
- 1992-09-17 AP APAP/P/1992/000428A patent/AP333A/en active
- 1992-09-17 NZ NZ244371A patent/NZ244371A/en unknown
- 1992-09-17 IL IL103205A patent/IL103205A0/xx unknown
- 1992-09-18 PT PT100881A patent/PT100881A/pt not_active Application Discontinuation
- 1992-09-21 MX MX9205358A patent/MX9205358A/es unknown
1993
- 1993-03-19 CN CN93103596A patent/CN1092409A/zh active Pending

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4056619A (en) *	1975-09-08	1977-11-01	Warner-Lambert Company	1-Substituted-2-(2-pyridinyl)ethanone N-oxides

Also Published As

Publication number	Publication date
IL103205A0 (en)	1993-02-21
AU2573592A (en)	1993-04-27
MX9205358A (es)	1993-07-01
EP0604529A1 (fr)	1994-07-06
MA22649A1 (fr)	1993-04-01
AP9200428A0 (en)	1992-10-31
CA2119467A1 (fr)	1993-04-01
JPH06510786A (ja)	1994-12-01
PT100881A (pt)	1993-10-29
CN1092409A (zh)	1994-09-21
WO1993006085A1 (fr)	1993-04-01
NZ244371A (en)	1995-11-27

Publication	Publication Date	Title
AP333A (en)	1994-04-25	Phenyl-substituted pyridyl aliphatic compounds for treating leukotriene-related diseases.
AU655428B2 (en)	1994-12-22	Benzoic acid derivatives
IE911912A1 (en)	1991-12-18	Pyridyl-benzoic acid derivatives for treating¹leukotriene-related diseases
EP0649412B1 (fr)	2003-01-15	Composes pharmaceutiques a base de pyridine
US5631262A (en)	1997-05-20	Pyridine compounds for treating leukotriene-related diseases
WO1996031476A1 (fr)	1996-10-10	Hydroxyethers aromatiques
WO1991018883A1 (fr)	1991-12-12	Derives d'acide pyridyle-benzoique a liaison amide utilises dans le traitement de maladies associees aux leucotrienes
JPH08175994A (ja)	1996-07-09	脂質代謝改善剤
WO1991018879A1 (fr)	1991-12-12	Derives d'acide phtalamique utilises dans le traitement de maladies associees aux leucotrienes
JPH07309837A (ja)	1995-11-28	ピリジン誘導体、その製造法および剤
WO1993011768A1 (fr)	1993-06-24	Composes a base de pyridyle destines au traitement du psoriasis
WO1993022285A1 (fr)	1993-11-11	Antagonistes de leucotrienes
WO1993010780A1 (fr)	1993-06-10	Composes de pyridine heterocyclique substituee et leurs utilisations
EP0733044A1 (fr)	1996-09-25	Composes
SI9200314A (sl)	1993-06-30	Spojine za zdravuanje bolezni, ki so v zvezi z levkotrieni