DK167614B1 - Quinolinderivater - Google Patents

Quinolinderivater Download PDF

Info

Publication number: DK167614B1
Authority: DK; Denmark
Prior art keywords: compounds; cyclooxygenase; quinoline; ear; lipoxygenase
Prior art date: 1985-10-03

Application number

DK462986A

Other languages

Danish (da)

English (en)

Other versions

DK462986D0 (da

DK462986A (da

Inventor

Iii Anthony Frank Kreft

Kenneth Lewis Kees

John Henry Musser

James Jacob Bicksler

Thomas Woolford Pattison

Original Assignee

American Home Prod

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.)

1985-10-03

Filing date

1986-09-29

Publication date

1993-11-29

1986-09-29 Application filed by American Home Prod filed Critical American Home Prod

1986-09-29 Publication of DK462986D0 publication Critical patent/DK462986D0/da

1987-04-04 Publication of DK462986A publication Critical patent/DK462986A/da

1993-11-29 Application granted granted Critical

1993-11-29 Publication of DK167614B1 publication Critical patent/DK167614B1/da

Links

SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 45
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 3
150000003248 quinolines Chemical class 0.000 claims description 3
IWFLDTGSELGSJS-UHFFFAOYSA-N 2-[(6-bromonaphthalen-2-yl)oxymethyl]quinoline Chemical compound C1=CC=CC2=NC(COC3=CC4=CC=C(C=C4C=C3)Br)=CC=C21 IWFLDTGSELGSJS-UHFFFAOYSA-N 0.000 claims description 2
NZLDBNPKNBCGEN-UHFFFAOYSA-N 2-(naphthalen-1-yloxymethyl)quinoline Chemical group C1=CC=CC2=NC(COC=3C4=CC=CC=C4C=CC=3)=CC=C21 NZLDBNPKNBCGEN-UHFFFAOYSA-N 0.000 claims 1
IQJFDLVLYVJZJD-UHFFFAOYSA-N 2-[(1-bromonaphthalen-2-yl)oxymethyl]quinoline Chemical compound C1=CC2=CC=CC=C2C(Br)=C1OCC1=CC=C(C=CC=C2)C2=N1 IQJFDLVLYVJZJD-UHFFFAOYSA-N 0.000 claims 1
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 39
229940114079 arachidonic acid Drugs 0.000 description 20
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 19
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 19
235000021342 arachidonic acid Nutrition 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
230000000694 effects Effects 0.000 description 15
239000000047 product Substances 0.000 description 15
150000002617 leukotrienes Chemical class 0.000 description 13
238000000034 method Methods 0.000 description 13
102000003820 Lipoxygenases Human genes 0.000 description 12
108090000128 Lipoxygenases Proteins 0.000 description 12
206010061218 Inflammation Diseases 0.000 description 11
230000004054 inflammatory process Effects 0.000 description 11
239000013078 crystal Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
239000003814 drug Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
206010030113 Oedema Diseases 0.000 description 7
229940079593 drug Drugs 0.000 description 7
230000002401 inhibitory effect Effects 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
229960002986 dinoprostone Drugs 0.000 description 6
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 6
KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
KGIJOOYOSFUGPC-CABOLEKPSA-N 5-HETE Natural products CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](O)CCCC(O)=O KGIJOOYOSFUGPC-CABOLEKPSA-N 0.000 description 5
KGIJOOYOSFUGPC-MSFIICATSA-N 5-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC=CCC=CCC=C\C=C\[C@@H](O)CCCC(O)=O KGIJOOYOSFUGPC-MSFIICATSA-N 0.000 description 5
230000004968 inflammatory condition Effects 0.000 description 5
210000000265 leukocyte Anatomy 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
240000001307 Myosotis scorpioides Species 0.000 description 4
208000006673 asthma Diseases 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
230000004060 metabolic process Effects 0.000 description 4
150000003180 prostaglandins Chemical class 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
150000003595 thromboxanes Chemical class 0.000 description 4
206010015150 Erythema Diseases 0.000 description 3
239000012981 Hank's balanced salt solution Substances 0.000 description 3
206010020751 Hypersensitivity Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
208000002193 Pain Diseases 0.000 description 3
241000700159 Rattus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
206010045240 Type I hypersensitivity Diseases 0.000 description 3
201000009961 allergic asthma Diseases 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
238000003556 assay Methods 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
210000000224 granular leucocyte Anatomy 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
230000002757 inflammatory effect Effects 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
229940094443 oxytocics prostaglandins Drugs 0.000 description 3
230000002265 prevention Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
206010002198 Anaphylactic reaction Diseases 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
229920002527 Glycogen Polymers 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
208000004454 Hyperalgesia Diseases 0.000 description 2
208000035154 Hyperesthesia Diseases 0.000 description 2
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
206010039085 Rhinitis allergic Diseases 0.000 description 2
201000010105 allergic rhinitis Diseases 0.000 description 2
230000036783 anaphylactic response Effects 0.000 description 2
208000003455 anaphylaxis Diseases 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
239000000043 antiallergic agent Substances 0.000 description 2
238000000376 autoradiography Methods 0.000 description 2
239000002585 base Substances 0.000 description 2
229950011260 betanaphthol Drugs 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
230000008859 change Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000008602 contraction Effects 0.000 description 2
238000011161 development Methods 0.000 description 2
229960001123 epoprostenol Drugs 0.000 description 2
231100000321 erythema Toxicity 0.000 description 2
210000000416 exudates and transudate Anatomy 0.000 description 2
229940096919 glycogen Drugs 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000005012 migration Effects 0.000 description 2
238000013508 migration Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000002599 prostaglandin synthase inhibitor Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
FQJZPYXGPYJJIH-UHFFFAOYSA-N 1-bromonaphthalen-2-ol Chemical compound C1=CC=CC2=C(Br)C(O)=CC=C21 FQJZPYXGPYJJIH-UHFFFAOYSA-N 0.000 description 1
ZNHVWPKMFKADKW-UHFFFAOYSA-N 12-HETE Chemical compound CCCCCC=CCC(O)C=CC=CCC=CCCCC(O)=O ZNHVWPKMFKADKW-UHFFFAOYSA-N 0.000 description 1
ZNHVWPKMFKADKW-ZYBDYUKJSA-N 12-HETE Natural products CCCCC\C=C/C[C@@H](O)\C=C\C=C/C\C=C/CCCC(O)=O ZNHVWPKMFKADKW-ZYBDYUKJSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
IKSFWXPXJNONAB-UHFFFAOYSA-N 2-[(2-fluorophenoxy)methyl]quinoline Chemical compound FC1=CC=CC=C1OCC1=CC=C(C=CC=C2)C2=N1 IKSFWXPXJNONAB-UHFFFAOYSA-N 0.000 description 1
JHIUTASCUYWDBV-UHFFFAOYSA-N 2-[(3-chlorophenoxy)methyl]quinoline Chemical compound ClC1=CC=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 JHIUTASCUYWDBV-UHFFFAOYSA-N 0.000 description 1
PUMQRQPUVSBCOT-UHFFFAOYSA-N 2-[(3-fluorophenoxy)methyl]quinoline Chemical compound FC1=CC=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 PUMQRQPUVSBCOT-UHFFFAOYSA-N 0.000 description 1
SLEFEGOGGSCFQY-UHFFFAOYSA-N 2-[(4-bromophenoxy)methyl]quinoline Chemical compound C1=CC(Br)=CC=C1OCC1=CC=C(C=CC=C2)C2=N1 SLEFEGOGGSCFQY-UHFFFAOYSA-N 0.000 description 1
HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
SJTBRFHBXDZMPS-UHFFFAOYSA-N 3-fluorophenol Chemical compound OC1=CC=CC(F)=C1 SJTBRFHBXDZMPS-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
XIQOEUKCZOPJAJ-UHFFFAOYSA-N 5,12-dihydroxyicosa-2,4,6,8-tetraenoic acid Chemical compound CCCCCCCCC(O)CCC=CC=CC(O)=CC=CC(O)=O XIQOEUKCZOPJAJ-UHFFFAOYSA-N 0.000 description 1
102000007081 Arachidonate Lipoxygenases Human genes 0.000 description 1
108010047815 Arachidonate Lipoxygenases Proteins 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
101800004538 Bradykinin Proteins 0.000 description 1
208000009079 Bronchial Spasm Diseases 0.000 description 1
208000014181 Bronchial disease Diseases 0.000 description 1
206010006482 Bronchospasm Diseases 0.000 description 1
206010006811 Bursitis Diseases 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
206010010744 Conjunctivitis allergic Diseases 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
206010012442 Dermatitis contact Diseases 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
102100035792 Kininogen-1 Human genes 0.000 description 1
239000004201 L-cysteine Substances 0.000 description 1
235000013878 L-cysteine Nutrition 0.000 description 1
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 1
239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
SGUKUZOVHSFKPH-UHFFFAOYSA-N PGG2 Natural products C1C2OOC1C(C=CC(OO)CCCCC)C2CC=CCCCC(O)=O SGUKUZOVHSFKPH-UHFFFAOYSA-N 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
206010070834 Sensitisation Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000000491 Tendinopathy Diseases 0.000 description 1
206010043255 Tendonitis Diseases 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
206010046851 Uveitis Diseases 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
230000004931 aggregating effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
208000002205 allergic conjunctivitis Diseases 0.000 description 1
208000002029 allergic contact dermatitis Diseases 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
208000030961 allergic reaction Diseases 0.000 description 1
208000028004 allergic respiratory disease Diseases 0.000 description 1
230000007815 allergy Effects 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
238000000540 analysis of variance Methods 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000003435 antirheumatic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
208000024998 atopic conjunctivitis Diseases 0.000 description 1
230000003416 augmentation Effects 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
239000003710 calcium ionophore Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000003399 chemotactic effect Effects 0.000 description 1
239000005482 chemotactic factor Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
230000000857 drug effect Effects 0.000 description 1
238000002651 drug therapy Methods 0.000 description 1
230000001206 effect on leukocytes Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
CJAONIOAQZUHPN-KKLWWLSJSA-N ethyl 12-[[2-[(2r,3r)-3-[2-[(12-ethoxy-12-oxododecyl)-methylamino]-2-oxoethoxy]butan-2-yl]oxyacetyl]-methylamino]dodecanoate Chemical compound CCOC(=O)CCCCCCCCCCCN(C)C(=O)CO[C@H](C)[C@@H](C)OCC(=O)N(C)CCCCCCCCCCCC(=O)OCC CJAONIOAQZUHPN-KKLWWLSJSA-N 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
230000028709 inflammatory response Effects 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
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 1
239000000314 lubricant Substances 0.000 description 1
230000002132 lysosomal effect Effects 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
229910001425 magnesium ion Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
210000000929 nociceptor Anatomy 0.000 description 1
230000000414 obstructive effect Effects 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
239000008188 pellet Substances 0.000 description 1
PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
SGUKUZOVHSFKPH-YNNPMVKQSA-N prostaglandin G2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](OO)CCCCC)[C@H]2C\C=C/CCCC(O)=O SGUKUZOVHSFKPH-YNNPMVKQSA-N 0.000 description 1
YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
201000004415 tendinitis Diseases 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- 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
- 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
- C07D215/16—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 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DK462986A 1985-10-03 1986-09-29 Quinolinderivater DK167614B1 (da)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US78414385A	1985-10-03	1985-10-03
US78414385		1985-10-03
US90561986		1986-09-12
US06/905,619 US4732978A (en)	1985-10-03	1986-09-12	Novel substituted naphthyloxymethyl quinoline derivatives as anti-inflammatory and antiallergy agents

Publications (3)

Publication Number	Publication Date
DK462986D0 DK462986D0 (da)	1986-09-29
DK462986A DK462986A (da)	1987-04-04
DK167614B1 true DK167614B1 (da)	1993-11-29

Family

ID=27120230

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK462986A DK167614B1 (da)	1985-10-03	1986-09-29	Quinolinderivater

Country Status (13)

Country	Link
US (1)	US4732978A (pt)
EP (1)	EP0223368B1 (pt)
KR (1)	KR890004129B1 (pt)
AU (1)	AU583153B2 (pt)
CA (1)	CA1267146A (pt)
DE (1)	DE3667786D1 (pt)
DK (1)	DK167614B1 (pt)
ES (1)	ES2012451B3 (pt)
GB (1)	GB2181135B (pt)
GR (1)	GR3000343T3 (pt)
HU (1)	HU196592B (pt)
IE (1)	IE58801B1 (pt)
PT (1)	PT83451B (pt)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NO174506B (no) *	1984-10-30	1994-02-07	Usv Pharma Corp	Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser
US4904786A (en) *	1986-01-27	1990-02-27	American Home Products Corporation	Quinoline compounds as antiallergic and antiinflammatory agents
DE3632329A1 (de) *	1986-09-24	1988-03-31	Bayer Ag	Substituierte phenylsulfonamide
DK196688A (da) *	1987-04-28	1988-10-29	Fujisawa Pharmaceutical Co	Bicykliske forbindelser og fremgangsmaade til fremstilling deraf
US4960892A (en) *	1988-06-10	1990-10-02	American Home Products Corporation	Naphthalenepropionic acid derivatives as anti-inflammatory/anti-allergic agents
US4920131A (en) *	1987-11-03	1990-04-24	Rorer Pharmaceutical Corp.	Quinoline derivatives and use thereof as antagonists of leukotriene D4
US5104882A (en) *	1987-11-25	1992-04-14	Merck Frosst Canada, Inc.	Diarylstrylquinoline diacids and pharmaceutical compositions thereof
US5204358A (en) *	1987-11-25	1993-04-20	Merck Frosst Canada, Inc.	Hetaryl styryl quinolines as leukotriene inhibitors
NZ233752A (en) *	1989-05-24	1993-05-26	Merck Frosst Canada Inc	Substituted quinoline derivatives, preparation and pharmaceutical compositions thereof
JPH03173874A (ja) *	1989-09-29	1991-07-29	Mitsubishi Kasei Corp	新規複素環化合物
DE3935139A1 (de) *	1989-10-21	1991-04-25	Bayer Ag	Substituierte (chinolin-2-yl-methoxy)phenyl-thioharnstoffe
ES2061406B1 (es) *	1993-05-07	1995-06-01	Uriach & Cia Sa J	Nuevos derivados de la 2-(quinolina) con actividad farmacologica.
GB9312853D0 (en) *	1993-06-22	1993-08-04	Euro Celtique Sa	Chemical compounds
US5591776A (en) *	1994-06-24	1997-01-07	Euro-Celtique, S.A.	Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV
US5922751A (en) *	1994-06-24	1999-07-13	Euro-Celtique, S.A.	Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same
US6372770B1 (en)	1994-10-12	2002-04-16	Euro-Celtique, S.A.	Benzoxazoles
DE69531623T2 (de) *	1994-10-12	2004-06-17	Euroceltique S.A.	Neue benzoxazole
EP0799040B1 (en) *	1994-12-13	2003-08-20	Euroceltique S.A.	Trisubstituted thioxanthines
US6025361A (en) *	1994-12-13	2000-02-15	Euro-Celtique, S.A.	Trisubstituted thioxanthines
WO1996018399A1 (en) *	1994-12-13	1996-06-20	Euro-Celtique, S.A.	Aryl thioxanthines
EP0725063A1 (de) *	1995-02-01	1996-08-07	Ciba-Geigy Ag	Chinolin-Derivate
US6166041A (en) *	1995-10-11	2000-12-26	Euro-Celtique, S.A.	2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma
US6075016A (en) *	1996-04-10	2000-06-13	Euro-Celtique S.A.	6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US31624A (en) *		1861-03-05		Tatting-frame
GB800713A (en) *	1955-04-27	1958-09-03	Boots Pure Drug Co Ltd	Sulphur-containing benzoxazole derivatives and compositions containing them
USRE31624E (en)	1979-11-26	1984-07-03	Forsyth Dental Infirmary For Children	Method of treating inflammation
US4563526A (en) *	1980-09-19	1986-01-07	Forsyth Dental Infirmary For Children	Substituted 2-(arylmethoxy) phenol compounds for the treatment of inflammation
NO174506B (no) *	1984-10-30	1994-02-07	Usv Pharma Corp	Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser
US4631287A (en) *	1985-04-16	1986-12-23	Usv Pharmaceutical Corp.	Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments
US4661499A (en) *	1985-06-18	1987-04-28	Merck Frosst Canada, Inc.	2-[(substituted)-phenoxymethyl]quinolines

1986
- 1986-09-12 US US06/905,619 patent/US4732978A/en not_active Expired - Lifetime
- 1986-09-29 PT PT83451A patent/PT83451B/pt not_active IP Right Cessation
- 1986-09-29 DK DK462986A patent/DK167614B1/da not_active IP Right Cessation
- 1986-10-01 CA CA000519538A patent/CA1267146A/en not_active Expired - Fee Related
- 1986-10-01 ES ES86307552T patent/ES2012451B3/es not_active Expired - Lifetime
- 1986-10-01 DE DE8686307552T patent/DE3667786D1/de not_active Expired - Fee Related
- 1986-10-01 EP EP86307552A patent/EP0223368B1/en not_active Expired
- 1986-10-01 GB GB8623616A patent/GB2181135B/en not_active Expired
- 1986-10-01 AU AU63414/86A patent/AU583153B2/en not_active Ceased
- 1986-10-02 HU HU864160A patent/HU196592B/hu not_active IP Right Cessation
- 1986-10-02 KR KR1019860008270A patent/KR890004129B1/ko not_active Expired
- 1986-10-02 IE IE261686A patent/IE58801B1/en not_active IP Right Cessation
1990
- 1990-02-06 GR GR90400067T patent/GR3000343T3/el unknown

Also Published As

Publication number	Publication date
IE862616L (en)	1987-04-04
GR3000343T3 (en)	1991-06-07
ES2012451B3 (es)	1990-04-01
PT83451A (pt)	1986-10-01
IE58801B1 (en)	1993-11-17
KR890004129B1 (ko)	1989-10-21
GB8623616D0 (en)	1986-11-05
KR870003991A (ko)	1987-05-06
HU196592B (en)	1988-12-28
DK462986D0 (da)	1986-09-29
PT83451B (pt)	1988-07-29
DK462986A (da)	1987-04-04
HUT42447A (en)	1987-07-28
GB2181135A (en)	1987-04-15
US4732978A (en)	1988-03-22
DE3667786D1 (de)	1990-02-01
CA1267146A (en)	1990-03-27
GB2181135B (en)	1989-09-13
EP0223368B1 (en)	1989-12-27
AU583153B2 (en)	1989-04-20
AU6341486A (en)	1987-04-09
EP0223368A1 (en)	1987-05-27

Publication	Publication Date	Title
DK167614B1 (da)	1993-11-29	Quinolinderivater
US4769461A (en)	1988-09-06	Quinolinyl benzene hydroxamic acids as anti-inflammatory/antiallergic agents
US4826990A (en)	1989-05-02	2-aryl substituted heterocyclic compounds as antiallergic and antiinflammatory agents
US5103014A (en)	1992-04-07	Certain 3,3'-[[[(2-phenyl-4-thiazolyl)methoxy]phenyl]methylene]dithiobis-propanoic acid derivatives
US4661596A (en)	1987-04-28	Quinolinyl (or pyridinyl) methoxy substituted naphthalene compounds as antiallergic agents
US4876346A (en)	1989-10-24	Quinoline compounds
US4675405A (en)	1987-06-23	Quinoline compounds as antiallergic and antithrombotic agents
NO861306L (no)	1986-10-06	Fremgangsmaate ved fremstilling av terapeutisk virksomme hydroxamatforbindelser.
DK168523B1 (da)	1994-04-11	N-substituerede 2-aminothiazoler, fremgangsmåde til deres fremstilling og præparater, der indeholder dem
US4895953A (en)	1990-01-23	2-Aryl substituted heterocyclic compounds as antiallergic and antiinflammatory agents
US4642347A (en)	1987-02-10	3(2-quinolinylalkoxy)phenols
US4594425A (en)	1986-06-10	Heterocyclic compounds as antiallergic agents
US4788304A (en)	1988-11-29	Phospholipase A2 inhibitors
US4933365A (en)	1990-06-12	Phospholipase A2 inhibitors
US4681940A (en)	1987-07-21	5-[3-[[2-quinolyl]methoxy]phenyl]-1,3-oxazoles
US4904786A (en)	1990-02-27	Quinoline compounds as antiallergic and antiinflammatory agents
US4942236A (en)	1990-07-17	2-aryl substituted pyridyl-containing phenyl sulfonamido compounds as antiallergic and antiinflammatory agents
EP0309541B1 (en)	1992-01-02	Sulfonylcarboxamides
US4870210A (en)	1989-09-26	Aminoguanidine derivative as anti-inflammatory agents
US4581457A (en)	1986-04-08	Heterocyclic sulfonamides
US4754043A (en)	1988-06-28	Oxazole and thiazole naphthalenes as antiallergic agents
NO169648B (no)	1992-04-13	Analogifremgangsmaate for fremstilling av terapeutisk aktive arakidonsyre-derivater
US4550172A (en)	1985-10-29	Novel heterocyclic compounds as antiallergic agents
US4554355A (en)	1985-11-19	Heterocyclic compounds as antiallergic agents
US4528392A (en)	1985-07-09	Aromatic compounds as antiallergic agents

Legal Events

Date	Code	Title	Description
1993-11-29	B1	Patent granted (law 1993)
1996-05-20	PBP	Patent lapsed