SE463819B - Pyridylmetoxianilinderivat, foerfarande foer framstaellning av dessa och en farmaceutisk komposition - Google Patents

Pyridylmetoxianilinderivat, foerfarande foer framstaellning av dessa och en farmaceutisk komposition

Info

Publication number: SE463819B
Authority: SE; Sweden
Prior art keywords: pyridylmethoxy; compound; formula; aniline; quinolylmethoxy
Prior art date: 1985-03-08

Application number

SE8600913A

Other languages

English (en)

Swedish (sv)

Other versions

SE8600913L (sv

SE8600913D0 (sv

Inventor

O B T Nielsen

I Ahnfelt-Roenne

Original Assignee

Leo Pharm Prod Ltd

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.)

1985-03-08

Filing date

1986-02-28

Publication date

1991-01-28

1985-03-08 Priority claimed from GB858506094A external-priority patent/GB8506094D0/en

1985-10-11 Priority claimed from GB858525153A external-priority patent/GB8525153D0/en

1986-02-28 Application filed by Leo Pharm Prod Ltd filed Critical Leo Pharm Prod Ltd

1986-02-28 Publication of SE8600913D0 publication Critical patent/SE8600913D0/xx

1986-09-09 Publication of SE8600913L publication Critical patent/SE8600913L/xx

1991-01-28 Publication of SE463819B publication Critical patent/SE463819B/sv

Links

238000000034 method Methods 0.000 title claims description 61
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 230
150000001875 compounds Chemical class 0.000 claims description 188
239000000203 mixture Substances 0.000 claims description 88
239000000047 product Substances 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 20
-1 cyano, nitro, amino, carboxy, hydroxy Chemical group 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
239000007788 liquid Substances 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 12
239000007787 solid Substances 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 8
239000004615 ingredient Substances 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
230000009467 reduction Effects 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
230000029936 alkylation Effects 0.000 claims description 5
238000005804 alkylation reaction Methods 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
238000009835 boiling Methods 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
235000011054 acetic acid Nutrition 0.000 claims description 4
150000001728 carbonyl compounds Chemical class 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 4
229960000905 indomethacin Drugs 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
229960002009 naproxen Drugs 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
239000011976 maleic acid Substances 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
CMWTZPSULFXXJA-VIFPVBQESA-M naproxen(1-) Chemical compound C1=C([C@H](C)C([O-])=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-M 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 claims description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
RTAPDZBZLSXHQQ-UHFFFAOYSA-N 8-methyl-3,7-dihydropurine-2,6-dione Chemical class N1C(=O)NC(=O)C2=C1N=C(C)N2 RTAPDZBZLSXHQQ-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
239000000464 adrenergic agent Substances 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000005526 alkyl sulfate group Chemical group 0.000 claims description 2
239000003529 anticholesteremic agent Substances 0.000 claims description 2
229940127226 anticholesterol agent Drugs 0.000 claims description 2
229940125715 antihistaminic agent Drugs 0.000 claims description 2
239000000739 antihistaminic agent Substances 0.000 claims description 2
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
239000000812 cholinergic antagonist Substances 0.000 claims description 2
239000000470 constituent Substances 0.000 claims description 2
LPEPZBJOKDYZAD-UHFFFAOYSA-M flufenamate Chemical compound [O-]C(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-M 0.000 claims description 2
229940067594 flufenamate Drugs 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
239000003862 glucocorticoid Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
229940071870 hydroiodic acid Drugs 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
229940098779 methanesulfonic acid Drugs 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
229960001639 penicillamine Drugs 0.000 claims description 2
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
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 claims description 2
239000000376 reactant Substances 0.000 claims description 2
NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 claims description 2
229960001940 sulfasalazine Drugs 0.000 claims description 2
229940037128 systemic glucocorticoids Drugs 0.000 claims description 2
150000003751 zinc Chemical class 0.000 claims description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
SQVNITZYWXMWOG-UHFFFAOYSA-N 2-cyclohexyl-1-(2-methylquinolin-4-yl)-3-(1,3-thiazol-2-yl)guanidine Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=NC1CCCCC1)NC1=NC=CS1 SQVNITZYWXMWOG-UHFFFAOYSA-N 0.000 claims 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
235000015165 citric acid Nutrition 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
239000012467 final product Substances 0.000 claims 1
150000002343 gold Chemical class 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
239000002243 precursor Substances 0.000 claims 1
150000003873 salicylate salts Chemical class 0.000 claims 1
229920006395 saturated elastomer Polymers 0.000 claims 1
239000011975 tartaric acid Substances 0.000 claims 1
235000002906 tartaric acid Nutrition 0.000 claims 1
229950006828 timegadine Drugs 0.000 claims 1
238000002844 melting Methods 0.000 description 64
230000008018 melting Effects 0.000 description 64
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
239000004480 active ingredient Substances 0.000 description 39
239000000243 solution Substances 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 24
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 22
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000013543 active substance Substances 0.000 description 16
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
150000002617 leukotrienes Chemical class 0.000 description 15
239000007921 spray Substances 0.000 description 14
ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 13
238000000921 elemental analysis Methods 0.000 description 13
238000002329 infrared spectrum Methods 0.000 description 13
239000000843 powder Substances 0.000 description 13
238000004809 thin layer chromatography Methods 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 12
229960001340 histamine Drugs 0.000 description 12
239000002245 particle Substances 0.000 description 12
239000003380 propellant Substances 0.000 description 12
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 11
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 10
210000003630 histaminocyte Anatomy 0.000 description 10
WDETYCRYUBGKCE-UHFFFAOYSA-N 2-(chloromethyl)quinolin-1-ium;chloride Chemical compound Cl.C1=CC=CC2=NC(CCl)=CC=C21 WDETYCRYUBGKCE-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
230000000694 effects Effects 0.000 description 9
238000001914 filtration Methods 0.000 description 9
239000000463 material Substances 0.000 description 9
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 8
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 8
FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
238000001816 cooling Methods 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
239000003085 diluting agent Substances 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 7
YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
ADVGKWPZRIDURE-UHFFFAOYSA-N 2'-Hydroxyacetanilide Chemical compound CC(=O)NC1=CC=CC=C1O ADVGKWPZRIDURE-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
241000700159 Rattus Species 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
229960001413 acetanilide Drugs 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
150000004683 dihydrates Chemical class 0.000 description 6
239000008187 granular material Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000003826 tablet Substances 0.000 description 6
238000011282 treatment Methods 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
206010020751 Hypersensitivity Diseases 0.000 description 5
208000006673 asthma Diseases 0.000 description 5
230000037396 body weight Effects 0.000 description 5
239000000872 buffer Substances 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
230000008602 contraction Effects 0.000 description 5
229960001760 dimethyl sulfoxide Drugs 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
210000003405 ileum Anatomy 0.000 description 5
238000002156 mixing Methods 0.000 description 5
230000002285 radioactive effect Effects 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 4
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
UZGLOGCJCWBBIV-UHFFFAOYSA-N 3-(chloromethyl)pyridin-1-ium;chloride Chemical compound Cl.ClCC1=CC=CN=C1 UZGLOGCJCWBBIV-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
108010058846 Ovalbumin Proteins 0.000 description 4
239000003963 antioxidant agent Substances 0.000 description 4
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239000007864 aqueous solution Substances 0.000 description 4
229940114079 arachidonic acid Drugs 0.000 description 4
235000021342 arachidonic acid Nutrition 0.000 description 4
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 4
108700003601 dimethylglycine Proteins 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
239000008101 lactose Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
230000001404 mediated effect Effects 0.000 description 4
QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 description 4
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
229940078490 n,n-dimethylglycine Drugs 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
229940092253 ovalbumin Drugs 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
150000003180 prostaglandins Chemical class 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000008215 water for injection Substances 0.000 description 4
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239000002555 ionophore Substances 0.000 description 1
230000000236 ionophoric effect Effects 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
238000002372 labelling Methods 0.000 description 1
239000010410 layer Substances 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
239000003199 leukotriene receptor blocking agent Substances 0.000 description 1
239000000865 liniment Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
229960000582 mepyramine Drugs 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
239000003595 mist Substances 0.000 description 1
238000009481 moist granulation Methods 0.000 description 1
239000007932 molded tablet Substances 0.000 description 1
210000000214 mouth Anatomy 0.000 description 1
MEFNZZZUMPJHST-UHFFFAOYSA-N n-(2,3-dichloro-4-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(O)C(Cl)=C1Cl MEFNZZZUMPJHST-UHFFFAOYSA-N 0.000 description 1
CDGZSMOCDYNULJ-UHFFFAOYSA-N n-(2-chloro-4-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(O)C=C1Cl CDGZSMOCDYNULJ-UHFFFAOYSA-N 0.000 description 1
GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000002997 ophthalmic solution Substances 0.000 description 1
229940054534 ophthalmic solution Drugs 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
230000035699 permeability Effects 0.000 description 1
238000005502 peroxidation Methods 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
230000000770 proinflammatory effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
150000003815 prostacyclins Chemical class 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
150000003902 salicylic acid esters Chemical class 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
IWOLVLSIZCEOHM-UHFFFAOYSA-M silver;dibenzyl phosphate Chemical compound [Ag+].C=1C=CC=CC=1COP(=O)([O-])OCC1=CC=CC=C1 IWOLVLSIZCEOHM-UHFFFAOYSA-M 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1

Classifications

- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- C07D213/34—Sulfur atoms to which a second hetero atom is attached
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Quinoline Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

SE8600913A 1985-03-08 1986-02-28 Pyridylmetoxianilinderivat, foerfarande foer framstaellning av dessa och en farmaceutisk komposition SE463819B (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB858506094A GB8506094D0 (en)	1985-03-08	1985-03-08	Chemical products
GB858525153A GB8525153D0 (en)	1985-10-11	1985-10-11	Chemical compounds

Publications (3)

Publication Number	Publication Date
SE8600913D0 SE8600913D0 (sv)	1986-02-28
SE8600913L SE8600913L (sv)	1986-09-09
SE463819B true SE463819B (sv)	1991-01-28

Family

ID=26288945

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8600913A SE463819B (sv)	1985-03-08	1986-02-28	Pyridylmetoxianilinderivat, foerfarande foer framstaellning av dessa och en farmaceutisk komposition

Country Status (18)

Country	Link
US (2)	US4826987A (pt)
JP (1)	JPH0764813B2 (pt)
AU (1)	AU585586B2 (pt)
BE (1)	BE904368A (pt)
CA (1)	CA1276640C (pt)
DE (1)	DE3607382A1 (pt)
DK (1)	DK166582B1 (pt)
ES (1)	ES8802610A1 (pt)
FR (1)	FR2578540B1 (pt)
GB (1)	GB2173788B (pt)
GR (1)	GR860628B (pt)
IE (1)	IE58870B1 (pt)
IT (1)	IT1221079B (pt)
LU (1)	LU86349A1 (pt)
NL (1)	NL8600596A (pt)
NZ (1)	NZ215347A (pt)
PT (1)	PT82147B (pt)
SE (1)	SE463819B (pt)

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EP0219308B1 (en) *	1985-10-16	1991-10-23	Merck Frosst Canada Inc.	2-substituted quinolines
DK196688A (da) *	1987-04-28	1988-10-29	Fujisawa Pharmaceutical Co	Bicykliske forbindelser og fremgangsmaade til fremstilling deraf
US4826990A (en) *	1987-09-30	1989-05-02	American Home Products Corporation	2-aryl substituted heterocyclic compounds as antiallergic and antiinflammatory agents
GB8728051D0 (en) *	1987-12-01	1988-01-06	Leo Pharm Prod Ltd	Chemical compounds
US4889935A (en) *	1987-12-18	1989-12-26	American Home Products Corporation	Aminoguanidine derivatives
WO1990012006A1 (en) *	1989-04-07	1990-10-18	Pfizer Inc.	Substituted 1-[3-(heteroarylmethoxy)phenyl]alkanols and related compounds in the treatment of asthma, arthritis and related diseases
DE3927369A1 (de) *	1989-08-19	1991-02-21	Bayer Ag	Substituierte n-(chinolin-2-yl-methoxy)benzyl-sulfonyl-harnstoffe
DE3935139A1 (de) *	1989-10-21	1991-04-25	Bayer Ag	Substituierte (chinolin-2-yl-methoxy)phenyl-thioharnstoffe
US5021576A (en) *	1989-10-27	1991-06-04	American Home Products Corporation	2-Anilino phenylacetic acid derivatives
US5324747A (en) *	1992-07-15	1994-06-28	Hoffmann-La Roche Inc.	N-substituted anilines, inhibitors of phospholipases A2
US5840318A (en) *	1993-05-11	1998-11-24	Immunom Technologies, Inc.	Methods and compositions for modulating immune systems of animals
US7189834B2 (en) *	1993-05-11	2007-03-13	Marshall William E	Oligoribonucleotides alert the immune system of animals to the imminence of microbial infection
US5508408A (en) *	1993-09-10	1996-04-16	Ciba-Geigy Corporation	Quinoline compound
US5795900A (en) *	1995-10-03	1998-08-18	Abbott Laboratories	Symmetrical bis-heteroaryl-methoxy-phenylalkyl carboxylates as inhibitors of leukotriene biosynthesis
US5668150A (en) *	1996-07-26	1997-09-16	Abbott Laboratories	Non-symmetrical bis-heteroarylmethoxyphenylalkyl carboxylates as inhibitors of leukotriene biosynthesis
EP1051181B1 (en) *	1997-12-31	2004-03-17	The University Of Kansas	Water soluble prodrugs of tertiary amine containing drugs and methods of making thereof
HN2001000008A (es)	2000-01-21	2003-12-11	Inc Agouron Pharmaceuticals	Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo
GB2431927B (en) *	2005-11-04	2010-03-17	Amira Pharmaceuticals Inc	5-Lipoxygenase-activating protein (FLAP) inhibitors
US8399666B2 (en) *	2005-11-04	2013-03-19	Panmira Pharmaceuticals, Llc	5-lipoxygenase-activating protein (FLAP) inhibitors
US7977359B2 (en) *	2005-11-04	2011-07-12	Amira Pharmaceuticals, Inc.	5-lipdxygenase-activating protein (FLAP) inhibitors
TW200920369A (en) *	2007-10-26	2009-05-16	Amira Pharmaceuticals Inc	5-lipoxygenase activating protein (flap) inhibitor
MX2010012814A (es) *	2008-05-23	2010-12-20	Amira Pharmaceuticals Inc	Inhibidor de proteina activadora de 5-lipoxigenasa.
US8546431B2 (en)	2008-10-01	2013-10-01	Panmira Pharmaceuticals, Llc	5-lipoxygenase-activating protein (FLAP) inhibitors
TW201215607A (en)	2010-07-02	2012-04-16	Lundbeck & Co As H	Aryl-and heteroarylamid derivatives as PDE10A enzyme inhibitor

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US31624A (en) *		1861-03-05		Tatting-frame
US2761865A (en) *	1954-07-07	1956-09-04	Hoffmann La Roche	Pyridylalkyl sulfones
US4003906A (en) *	1974-01-22	1977-01-18	The Dow Chemical Company	Substituted pyridinyl methylthio or (methylsulfonyl)benzeneamines
GB2069493B (en) *	1980-02-20	1984-02-29	Wyeth John & Brother Ltd	Pyridine derivatives
GB2069492B (en) *	1980-02-20	1984-02-29	Wyeth John & Brother Ltd	Sulphur compounds
US4567184A (en) *	1982-12-01	1986-01-28	Usv Pharmaceutical Corporation	Certain aryl or hetero-aryl derivatives of 1-hydroxy-pentane or 1-hydroxy-hexane which are useful for treating inflammation and allergies
IE56702B1 (en) *	1982-12-01	1991-11-06	Usv Pharma Corp	Antiinflammatory antiallergic compounds
JPS5988835U (ja) *	1982-12-06	1984-06-15	ホシデン株式会社	スイツチ
US4486593A (en) *	1983-01-19	1984-12-04	The Upjohn Company	2-,3-, or 4-Pyridinylmethylamino arylic acids as thromboxane A2 synthetase and 5-lipoxygenase inhibitors
US4563463A (en) *	1983-03-18	1986-01-07	Usv Pharmaceutical Corp.	2-Oxo-1,3-oxazolo[4,5-h] quinolines useful as anti-allergy agents
US4554355A (en) *	1984-07-19	1985-11-19	American Home Products Corporation	Heterocyclic compounds as antiallergic agents
US5109009A (en) *	1985-03-08	1992-04-28	Leo Pharmaceutical Products Ltd.	Quinoline and pyridine compounds and inhibition of 5-lipoxygenases therewith

1986
- 1986-02-10 IE IE37086A patent/IE58870B1/en not_active IP Right Cessation
- 1986-02-20 GB GB08604183A patent/GB2173788B/en not_active Expired
- 1986-02-28 US US06/834,542 patent/US4826987A/en not_active Expired - Fee Related
- 1986-02-28 SE SE8600913A patent/SE463819B/sv not_active IP Right Cessation
- 1986-03-03 NZ NZ215347A patent/NZ215347A/xx unknown
- 1986-03-04 DK DK096986A patent/DK166582B1/da not_active IP Right Cessation
- 1986-03-06 IT IT67183/86A patent/IT1221079B/it active
- 1986-03-06 PT PT82147A patent/PT82147B/pt not_active IP Right Cessation
- 1986-03-06 CA CA000503464A patent/CA1276640C/en not_active Expired - Lifetime
- 1986-03-06 GR GR860628A patent/GR860628B/el unknown
- 1986-03-06 DE DE19863607382 patent/DE3607382A1/de not_active Ceased
- 1986-03-07 NL NL8600596A patent/NL8600596A/nl not_active Application Discontinuation
- 1986-03-07 LU LU86349A patent/LU86349A1/fr unknown
- 1986-03-07 FR FR868603268A patent/FR2578540B1/fr not_active Expired - Lifetime
- 1986-03-07 AU AU54444/86A patent/AU585586B2/en not_active Ceased
- 1986-03-07 ES ES552805A patent/ES8802610A1/es not_active Expired
- 1986-03-07 BE BE0/216378A patent/BE904368A/fr not_active IP Right Cessation
- 1986-03-08 JP JP61051286A patent/JPH0764813B2/ja not_active Expired - Lifetime
1990
- 1990-12-31 US US07/633,390 patent/US5157039A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US4826987A (en)	1989-05-02
DK166582B1 (da)	1993-06-14
SE8600913L (sv)	1986-09-09
JPS61207374A (ja)	1986-09-13
JPH0764813B2 (ja)	1995-07-12
GB2173788A (en)	1986-10-22
SE8600913D0 (sv)	1986-02-28
IE860370L (en)	1986-09-08
AU585586B2 (en)	1989-06-22
GB8604183D0 (en)	1986-03-26
NZ215347A (en)	1990-02-26
IE58870B1 (en)	1993-11-17
PT82147B (pt)	1988-07-29
GB2173788B (en)	1988-08-10
DK96986D0 (da)	1986-03-04
DK96986A (da)	1986-09-09
ES552805A0 (es)	1988-09-16
AU5444486A (en)	1986-09-18
FR2578540A1 (fr)	1986-09-12
BE904368A (fr)	1986-09-08
FR2578540B1 (fr)	1990-11-16
GR860628B (en)	1986-06-26
IT8667183A0 (it)	1986-03-06
ES8802610A1 (es)	1988-09-16
US5157039A (en)	1992-10-20
LU86349A1 (fr)	1987-04-02
NL8600596A (nl)	1986-10-01
PT82147A (en)	1986-04-01
CA1276640C (en)	1990-11-20
DE3607382A1 (de)	1986-09-11
IT1221079B (it)	1990-06-21

Publication	Publication Date	Title
SE463819B (sv)	1991-01-28	Pyridylmetoxianilinderivat, foerfarande foer framstaellning av dessa och en farmaceutisk komposition
US5110819A (en)	1992-05-05	Substituted quinolines and medicinal use thereof
EP0091795A1 (en)	1983-10-19	Olefinic benzimidazoles
US5109009A (en)	1992-04-28	Quinoline and pyridine compounds and inhibition of 5-lipoxygenases therewith
US20030096826A1 (en)	2003-05-22	Arylsulfonamide ethers, and methods of use thereof
US7230020B2 (en)	2007-06-12	11β-hydroxysteroid dehydrogenase inhibitors
AU617386B2 (en)	1991-11-28	Substituted quinolines
US5576438A (en)	1996-11-19	Isoserine derivatives and their use as leukotriene antagonists
US5234932A (en)	1993-08-10	Substituted quinolines and leucotriene antagonism treatment therewith
CZ284006B6 (cs)	1998-07-15	Chinolinové sloučeniny, způsob jejich přípravy a farmaceutické přípravky tyto sloučeniny obsahující
EP0034462A2 (en)	1981-08-26	Imidodisulfamide derivatives, their preparation and use in pharmaceutical compositions
DK170576B1 (da)	1995-10-30	Substituerede quinoliner, deres fremstilling og farmaceutiske præparater indeholdende samme
AU686820B2 (en)	1998-02-12	Quinoline derivatives as leukotriene antagonists

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