NL8600596A - Geneeskrachtige verbindingen, werkwijzen ter bereiding daarvan alsmede deze verbindingen als actieve component bevattende preparaten. - Google Patents

Geneeskrachtige verbindingen, werkwijzen ter bereiding daarvan alsmede deze verbindingen als actieve component bevattende preparaten. Download PDF

Info

Publication number: NL8600596A
Authority: NL; Netherlands
Prior art keywords: formula; compound; pyridylmethoxy; aniline; title compound
Prior art date: 1985-03-08

Application number

NL8600596A

Other languages

English (en)

Dutch (nl)

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

1986-03-07

Publication date

1986-10-01

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

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

1986-03-07 Application filed by Leo Pharm Prod Ltd filed Critical Leo Pharm Prod Ltd

1986-10-01 Publication of NL8600596A publication Critical patent/NL8600596A/nl

Links

150000001875 compounds Chemical class 0.000 title claims description 224
238000000034 method Methods 0.000 title claims description 124
238000002360 preparation method Methods 0.000 title claims description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 258
239000000203 mixture Substances 0.000 claims description 96
-1 cyano, nitro, amino, carboxy, hydroxy Chemical group 0.000 claims description 39
238000006243 chemical reaction Methods 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
239000000047 product Substances 0.000 claims description 21
239000007788 liquid Substances 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
239000007787 solid Substances 0.000 claims description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000000463 material Substances 0.000 claims description 9
230000000694 effects Effects 0.000 claims description 7
238000011282 treatment Methods 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
230000037396 body weight Effects 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000002577 pseudohalo group Chemical group 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
206010020751 Hypersensitivity Diseases 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
238000009835 boiling Methods 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
230000009467 reduction Effects 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
230000029936 alkylation Effects 0.000 claims description 4
238000005804 alkylation reaction Methods 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
150000001728 carbonyl compounds Chemical class 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 4
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 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
201000004681 Psoriasis Diseases 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
206010047163 Vasospasm Diseases 0.000 claims description 3
208000026935 allergic disease Diseases 0.000 claims description 3
230000007815 allergy Effects 0.000 claims description 3
230000004968 inflammatory condition Effects 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
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 3
229910052717 sulfur Chemical group 0.000 claims description 3
239000011593 sulfur Chemical group 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
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 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
125000005526 alkyl sulfate group Chemical group 0.000 claims description 2
230000001387 anti-histamine Effects 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
239000003862 glucocorticoid Substances 0.000 claims description 2
150000002343 gold Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229960000905 indomethacin Drugs 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
229960001639 penicillamine Drugs 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
229960001940 sulfasalazine Drugs 0.000 claims description 2
229940037128 systemic glucocorticoids Drugs 0.000 claims description 2
229950006828 timegadine 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
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
230000003647 oxidation Effects 0.000 claims 2
238000007254 oxidation reaction Methods 0.000 claims 2
238000006722 reduction reaction Methods 0.000 claims 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 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 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
201000004624 Dermatitis Diseases 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
241001331845 Equus asinus x caballus Species 0.000 claims 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-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
235000011054 acetic acid Nutrition 0.000 claims 1
239000000464 adrenergic agent Substances 0.000 claims 1
229910010277 boron hydride Inorganic materials 0.000 claims 1
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 claims 1
235000015165 citric acid Nutrition 0.000 claims 1
206010009887 colitis Diseases 0.000 claims 1
235000019253 formic acid Nutrition 0.000 claims 1
150000007529 inorganic bases Chemical class 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
239000011976 maleic acid Substances 0.000 claims 1
229940098779 methanesulfonic acid Drugs 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
229940127557 pharmaceutical product Drugs 0.000 claims 1
235000019260 propionic acid Nutrition 0.000 claims 1
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 1
238000005932 reductive alkylation reaction Methods 0.000 claims 1
150000003873 salicylate salts Chemical class 0.000 claims 1
230000009291 secondary effect Effects 0.000 claims 1
239000011975 tartaric acid Substances 0.000 claims 1
235000002906 tartaric acid Nutrition 0.000 claims 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
229910052727 yttrium Inorganic materials 0.000 claims 1
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 58
238000002844 melting Methods 0.000 description 53
230000008018 melting Effects 0.000 description 53
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
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239000000243 solution Substances 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
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NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 22
150000002617 leukotrienes Chemical class 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 13
238000009472 formulation Methods 0.000 description 13
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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230000015572 biosynthetic process Effects 0.000 description 9
238000001914 filtration Methods 0.000 description 9
ADVGKWPZRIDURE-UHFFFAOYSA-N 2'-Hydroxyacetanilide Chemical compound CC(=O)NC1=CC=CC=C1O ADVGKWPZRIDURE-UHFFFAOYSA-N 0.000 description 8
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 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
230000005764 inhibitory process Effects 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
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000000725 suspension Substances 0.000 description 8
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 7
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
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PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000007233 immunological mechanism Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
210000004969 inflammatory cell Anatomy 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
239000002555 ionophore Substances 0.000 description 1
230000000236 ionophoric effect Effects 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
230000011268 leukocyte chemotaxis Effects 0.000 description 1
GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 description 1
239000003199 leukotriene receptor blocking agent Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000006210 lotion Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 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
230000004060 metabolic process Effects 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
238000000465 moulding Methods 0.000 description 1
210000000214 mouth Anatomy 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
210000000440 neutrophil Anatomy 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 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
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 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
WYMSBXTXOHUIGT-UHFFFAOYSA-N paraoxon Chemical compound CCOP(=O)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 WYMSBXTXOHUIGT-UHFFFAOYSA-N 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000001991 pathophysiological effect Effects 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
230000037361 pathway 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
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
230000000704 physical effect Effects 0.000 description 1
239000003058 plasma substitute Substances 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
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 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
230000002685 pulmonary effect Effects 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
230000000754 repressing effect Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
208000020029 respiratory tract infectious disease Diseases 0.000 description 1
230000004044 response Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
150000003902 salicylic acid esters Chemical class 0.000 description 1
150000003335 secondary amines Chemical group 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
238000007493 shaping process Methods 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
239000011734 sodium Substances 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
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 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
238000004611 spectroscopical analysis Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
238000004544 sputter deposition Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000006228 supernatant Substances 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
230000000699 topical effect Effects 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
235000012431 wafers Nutrition 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)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NL8600596A 1985-03-08 1986-03-07 Geneeskrachtige verbindingen, werkwijzen ter bereiding daarvan alsmede deze verbindingen als actieve component bevattende preparaten. NL8600596A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB858506094A GB8506094D0 (en)	1985-03-08	1985-03-08	Chemical products
GB8506094		1985-03-08
GB8525153		1985-10-11
GB858525153A GB8525153D0 (en)	1985-10-11	1985-10-11	Chemical compounds

Publications (1)

Publication Number	Publication Date
NL8600596A true NL8600596A (nl)	1986-10-01

Family

ID=26288945

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8600596A NL8600596A (nl)	1985-03-08	1986-03-07	Geneeskrachtige verbindingen, werkwijzen ter bereiding daarvan alsmede deze verbindingen als actieve component bevattende preparaten.

Country Status (18)

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

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3682160D1 (de) *	1985-10-16	1991-11-28	Merck Frosst Canada Inc	2-substituierte chinoline.
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
US5248685A (en) *	1989-04-07	1993-09-28	Pfizer Inc.	Substituted 1-[3-(heteroarylmethoxy)phenyl]alkanols and related compounds in the treatment of asthma
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
US5985856A (en) *	1997-12-31	1999-11-16	University Of Kansas	Water soluble prodrugs of secondary and 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
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
GB2431927B (en) *	2005-11-04	2010-03-17	Amira Pharmaceuticals Inc	5-Lipoxygenase-activating protein (FLAP) inhibitors
TW200920369A (en) *	2007-10-26	2009-05-16	Amira Pharmaceuticals Inc	5-lipoxygenase activating protein (flap) inhibitor
CN102137858B (zh) *	2008-05-23	2014-07-23	潘米拉制药有限责任公司	5-脂氧合酶-活化蛋白抑制剂
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

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
GB2069492B (en) *	1980-02-20	1984-02-29	Wyeth John & Brother Ltd	Sulphur compounds
GB2069493B (en) *	1980-02-20	1984-02-29	Wyeth John & Brother Ltd	Pyridine derivatives
IE56702B1 (en) *	1982-12-01	1991-11-06	Usv Pharma Corp	Antiinflammatory antiallergic 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
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 SE SE8600913A patent/SE463819B/sv not_active IP Right Cessation
- 1986-02-28 US US06/834,542 patent/US4826987A/en not_active Expired - Fee Related
- 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 GR GR860628A patent/GR860628B/el unknown
- 1986-03-06 PT PT82147A patent/PT82147B/pt not_active IP Right Cessation
- 1986-03-06 IT IT67183/86A patent/IT1221079B/it active
- 1986-03-06 DE DE19863607382 patent/DE3607382A1/de not_active Ceased
- 1986-03-06 CA CA000503464A patent/CA1276640C/fr not_active Expired - Lifetime
- 1986-03-07 FR FR868603268A patent/FR2578540B1/fr not_active Expired - Lifetime
- 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
- 1986-03-07 AU AU54444/86A patent/AU585586B2/en not_active Ceased
- 1986-03-07 NL NL8600596A patent/NL8600596A/nl not_active Application Discontinuation
- 1986-03-07 LU LU86349A patent/LU86349A1/fr unknown
- 1986-03-08 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
IT1221079B (it)	1990-06-21
DK96986A (da)	1986-09-09
NZ215347A (en)	1990-02-26
JPH0764813B2 (ja)	1995-07-12
ES552805A0 (es)	1988-09-16
CA1276640C (fr)	1990-11-20
AU5444486A (en)	1986-09-18
FR2578540A1 (fr)	1986-09-12
IE58870B1 (en)	1993-11-17
IT8667183A0 (it)	1986-03-06
US5157039A (en)	1992-10-20
AU585586B2 (en)	1989-06-22
PT82147A (en)	1986-04-01
BE904368A (fr)	1986-09-08
FR2578540B1 (fr)	1990-11-16
SE463819B (sv)	1991-01-28
DE3607382A1 (de)	1986-09-11
PT82147B (pt)	1988-07-29
SE8600913D0 (sv)	1986-02-28
DK96986D0 (da)	1986-03-04
ES8802610A1 (es)	1988-09-16
LU86349A1 (fr)	1987-04-02
SE8600913L (sv)	1986-09-09
GR860628B (en)	1986-06-26
DK166582B1 (da)	1993-06-14
JPS61207374A (ja)	1986-09-13
US4826987A (en)	1989-05-02
GB8604183D0 (en)	1986-03-26
IE860370L (en)	1986-09-08
GB2173788B (en)	1988-08-10
GB2173788A (en)	1986-10-22

Legal Events

Date	Code	Title
1988-01-04	BT	A notification was added to the application dossier and made available to the public
1992-11-02	BA	A request for search or an international-type search has been filed
1992-12-01	BB	A search report has been drawn up
1993-01-04	BC	A request for examination has been filed
1997-12-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US4826987A (en)	1989-05-02	Pyridyl and quinoline derivatives
EP0691966B1 (fr)	1998-09-09	Quinoleines comme inhibiteurs de la phosphodiesterase type iv
CA1336602C (fr)	1995-08-08	Quinolylmethoxyanilines substituees
AU646007B2 (en)	1994-02-03	3-substituted-1-(aryl or arylalkyl)-2(1h)-quinolinones
JPS62212334A (ja)	1987-09-18	高過敏性疾病の治療剤としてのアリ−ル及びヘテロアリ−ルエ−テル類
JPS63290821A (ja)	1988-11-28	抗不整脈剤
US5109009A (en)	1992-04-28	Quinoline and pyridine compounds and inhibition of 5-lipoxygenases therewith
NL8502012A (nl)	1986-02-03	Aminofenolverbindingen.
EP0219308A2 (fr)	1987-04-22	Quinoléines 2-substituées
AU617386B2 (en)	1991-11-28	Substituted quinolines
US5945433A (en)	1999-08-31	Quinoline derivatives containing a diol as leukotriene antagonists
CA2134565A1 (fr)	1994-02-17	Derives de l'isoserine et leur emploi comme antagonistes de la leucotriene
JPH05500060A (ja)	1993-01-14	置換キノリン類
CA2159603C (fr)	2006-07-25	Quinoleines en tant qu'inhibiteurs de la phosphodiesterase de type iv
DK170576B1 (da)	1995-10-30	Substituerede quinoliner, deres fremstilling og farmaceutiske præparater indeholdende samme
WO1997019925A9 (fr)	1998-04-23	Derives de la quinoleine contenant un diol comme antagonistes des leucotrienes
HUT76443A (en)	1997-09-29	Quinoline derivatives as leukotriene antagonists,pharmaceutical compositions containing them and process for producing them