DK168534B1 - Quinolinderivat og farmaceutisk præparat indeholdende et sådant derivat - Google Patents

Quinolinderivat og farmaceutisk præparat indeholdende et sådant derivat Download PDF

Info

Publication number: DK168534B1
Authority: DK; Denmark
Prior art keywords: cooh; phenyl; acid; chloroquinolin; added
Prior art date: 1986-02-14

Application number

DK072287A

Other languages

Danish (da)

English (en)

Other versions

DK72287A (da

DK72287D0 (da

Inventor

Robert N Young

Robert Zamboni

Serge Leger

Original Assignee

Merck Frosst Canada Inc

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.)

1986-02-14

Filing date

1987-02-13

Publication date

1994-04-18

1987-02-13 Application filed by Merck Frosst Canada Inc filed Critical Merck Frosst Canada Inc

1987-02-13 Publication of DK72287D0 publication Critical patent/DK72287D0/da

1987-08-15 Publication of DK72287A publication Critical patent/DK72287A/da

1994-04-18 Application granted granted Critical

1994-04-18 Publication of DK168534B1 publication Critical patent/DK168534B1/da

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 11
125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
-1 R4 = H Chemical class 0.000 claims abstract description 54
150000003839 salts Chemical class 0.000 claims abstract description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000002367 halogens Chemical class 0.000 claims abstract description 10
150000003536 tetrazoles Chemical class 0.000 claims abstract description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 5
150000001875 compounds Chemical class 0.000 claims description 146
239000002253 acid Substances 0.000 claims description 42
239000004480 active ingredient Substances 0.000 claims description 15
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 12
150000002617 leukotrienes Chemical class 0.000 claims description 10
239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 7
239000005557 antagonist Substances 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
229940082988 antihypertensives serotonin antagonists Drugs 0.000 claims description 3
239000003420 antiserotonin agent Substances 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
150000003248 quinolines Chemical class 0.000 claims description 3
GFLLPUKOZOHDNV-UHFFFAOYSA-N 3-[(3-amino-3-oxopropyl)sulfanyl-[3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl]methyl]sulfanylpropanoic acid Chemical compound NC(=O)CCSC(SCCC(O)=O)C1=CC=CC(C=CC=2N=C3C=C(Cl)C=CC3=CC=2)=C1 GFLLPUKOZOHDNV-UHFFFAOYSA-N 0.000 claims description 2
NIXBZRJGJRDATK-UHFFFAOYSA-N 3-[[3-[2-(7-chloroquinolin-2-yl)ethyl]phenyl]-[3-(dimethylamino)-3-oxopropyl]sulfanylmethyl]sulfanylpropanoic acid Chemical compound CN(C)C(=O)CCSC(SCCC(O)=O)C1=CC=CC(CCC=2N=C3C=C(Cl)C=CC3=CC=2)=C1 NIXBZRJGJRDATK-UHFFFAOYSA-N 0.000 claims description 2
230000003042 antagnostic effect Effects 0.000 claims description 2
239000000730 antalgic agent Substances 0.000 claims description 2
230000002093 peripheral effect Effects 0.000 claims description 2
239000002089 prostaglandin antagonist Substances 0.000 claims description 2
239000002599 prostaglandin synthase inhibitor Substances 0.000 claims description 2
229940044551 receptor antagonist Drugs 0.000 claims description 2
239000002464 receptor antagonist Substances 0.000 claims description 2
239000000739 antihistaminic agent Substances 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
159000000000 sodium salts Chemical class 0.000 claims 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 18
125000004432 carbon atom Chemical group C* 0.000 abstract description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 5
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 3
125000003342 alkenyl group Chemical group 0.000 abstract 3
125000005842 heteroatom Chemical group 0.000 abstract 3
101150047265 COR2 gene Proteins 0.000 abstract 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 abstract 2
125000000304 alkynyl group Chemical group 0.000 abstract 2
101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 abstract 1
125000002015 acyclic group Chemical group 0.000 abstract 1
125000002252 acyl group Chemical group 0.000 abstract 1
150000001413 amino acids Chemical class 0.000 abstract 1
125000002618 bicyclic heterocycle group Chemical group 0.000 abstract 1
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 abstract 1
125000000623 heterocyclic group Chemical group 0.000 abstract 1
125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
125000002950 monocyclic group Chemical group 0.000 abstract 1
150000003254 radicals Chemical class 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 191
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 105
239000000243 solution Substances 0.000 description 91
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
235000019439 ethyl acetate Nutrition 0.000 description 71
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
239000011541 reaction mixture Substances 0.000 description 63
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
238000002360 preparation method Methods 0.000 description 55
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 52
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
239000000203 mixture Substances 0.000 description 47
238000003818 flash chromatography Methods 0.000 description 40
238000000034 method Methods 0.000 description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
229910052938 sodium sulfate Inorganic materials 0.000 description 26
235000011152 sodium sulphate Nutrition 0.000 description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000000725 suspension Substances 0.000 description 24
235000019441 ethanol Nutrition 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
239000012267 brine Substances 0.000 description 15
239000012044 organic layer Substances 0.000 description 15
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
238000000746 purification Methods 0.000 description 14
239000007787 solid Substances 0.000 description 14
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 12
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 10
239000005695 Ammonium acetate Substances 0.000 description 10
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
150000001299 aldehydes Chemical class 0.000 description 10
235000019257 ammonium acetate Nutrition 0.000 description 10
229940043376 ammonium acetate Drugs 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
239000000872 buffer Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000011734 sodium Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
230000000694 effects Effects 0.000 description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 8
239000003921 oil Substances 0.000 description 8
SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical class C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000003826 tablet Substances 0.000 description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
WQZQFYRSYLXBGP-UHFFFAOYSA-N 7-chloro-2-methylquinoline Chemical compound C1=CC(Cl)=CC2=NC(C)=CC=C21 WQZQFYRSYLXBGP-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical class O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 description 7
239000002775 capsule Substances 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
230000006378 damage Effects 0.000 description 7
150000005690 diesters Chemical class 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
238000000605 extraction Methods 0.000 description 7
239000007788 liquid Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
239000000843 powder Substances 0.000 description 7
ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 description 6
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
230000001120 cytoprotective effect Effects 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
WJOPLBNTJYROCF-UHFFFAOYSA-N 2-(bromomethyl)-7-chloroquinoline Chemical compound C1=CC(CBr)=NC2=CC(Cl)=CC=C21 WJOPLBNTJYROCF-UHFFFAOYSA-N 0.000 description 5
150000001242 acetic acid derivatives Chemical class 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
230000003266 anti-allergic effect Effects 0.000 description 5
230000037396 body weight Effects 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 description 5
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 5
150000003573 thiols Chemical class 0.000 description 5
IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
230000001088 anti-asthma Effects 0.000 description 4
230000003110 anti-inflammatory effect Effects 0.000 description 4
239000000924 antiasthmatic agent Substances 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
201000010099 disease Diseases 0.000 description 4
239000000284 extract Substances 0.000 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 description 4
239000012442 inert solvent Substances 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
PLFQAMVLWPQPLL-UHFFFAOYSA-N methyl 3-[[3-(dimethylamino)-3-oxopropyl]sulfanyl-(3-formylphenyl)methyl]sulfanylpropanoate Chemical compound COC(=O)CCSC(SCCC(=O)N(C)C)C1=CC=CC(C=O)=C1 PLFQAMVLWPQPLL-UHFFFAOYSA-N 0.000 description 4
RIADZCKVSOACHV-UHFFFAOYSA-N methyl 3-[[3-(dimethylamino)-3-oxopropyl]sulfanyl-[3-(hydroxymethyl)phenyl]methyl]sulfanylpropanoate Chemical compound COC(=O)CCSC(SCCC(=O)N(C)C)C1=CC=CC(CO)=C1 RIADZCKVSOACHV-UHFFFAOYSA-N 0.000 description 4
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000047 product Substances 0.000 description 4
150000005599 propionic acid derivatives Chemical class 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
MUHKOIACOCBEND-UHFFFAOYSA-N 3-[[tert-butyl(diphenyl)silyl]oxymethyl]benzaldehyde Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)OCC1=CC=CC(C=O)=C1 MUHKOIACOCBEND-UHFFFAOYSA-N 0.000 description 3
XJNCVVVHUWTVCB-UHFFFAOYSA-N 3-methylsulfanylbenzaldehyde Chemical compound CSC1=CC=CC(C=O)=C1 XJNCVVVHUWTVCB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
MOMWFXLCFJOAFX-UHFFFAOYSA-N OOOOOOOO Chemical compound OOOOOOOO MOMWFXLCFJOAFX-UHFFFAOYSA-N 0.000 description 3
208000027418 Wounds and injury Diseases 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
208000010668 atopic eczema Diseases 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
208000014674 injury Diseases 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
UXBJXJHRVOEYPA-UHFFFAOYSA-N n,n-dimethyl-3-sulfanylpropanamide Chemical compound CN(C)C(=O)CCS UXBJXJHRVOEYPA-UHFFFAOYSA-N 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
RLGKSXCGHMXELQ-ZRDIBKRKSA-N trans-2-styrylquinoline Chemical class C=1C=C2C=CC=CC2=NC=1\C=C\C1=CC=CC=C1 RLGKSXCGHMXELQ-ZRDIBKRKSA-N 0.000 description 3
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 2
NKYFJZAKUPSUSH-UHFFFAOYSA-N 1-bromo-3-methylsulfanylbenzene Chemical compound CSC1=CC=CC(Br)=C1 NKYFJZAKUPSUSH-UHFFFAOYSA-N 0.000 description 2
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JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
201000006370 kidney failure Diseases 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
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 1
229910052744 lithium Inorganic materials 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
229960003646 lysine Drugs 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
150000002696 manganese Chemical class 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
LKJDBNVYDOBYMF-UHFFFAOYSA-N methyl 3-[[3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-[3-(dimethylamino)-3-oxopropyl]sulfanylmethyl]sulfanylpropanoate Chemical compound COC(=O)CCSC(SCCC(=O)N(C)C)C1=CC=CC(C=CC=2N=C3C=C(Cl)C=CC3=CC=2)=C1 LKJDBNVYDOBYMF-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 1
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000007932 molded tablet Substances 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
IFYDWYVPVAMGRO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)NCCCN(C)C IFYDWYVPVAMGRO-UHFFFAOYSA-N 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
230000000414 obstructive effect Effects 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
229960000381 omeprazole Drugs 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000037361 pathway Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
VMXUWOKSQNHOCA-UKTHLTGXSA-N ranitidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-UKTHLTGXSA-N 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
FKWYVTBQNKHOIW-UHFFFAOYSA-N s-(1h-pyrazol-5-yl)thiohydroxylamine Chemical class NSC=1C=CNN=1 FKWYVTBQNKHOIW-UHFFFAOYSA-N 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
238000005245 sintering Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
XNAYQOBPAXEYLI-LQKFMROPSA-M sodium;3-[(r)-[3-[(e)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-[3-(dimethylamino)-3-oxopropyl]sulfanylmethyl]sulfanylpropanoate Chemical compound [Na+].CN(C)C(=O)CCS[C@H](SCCC([O-])=O)C1=CC=CC(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)=C1 XNAYQOBPAXEYLI-LQKFMROPSA-M 0.000 description 1
239000007921 spray Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000002602 strong irritant Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
229960000351 terfenadine Drugs 0.000 description 1
MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229960004559 theobromine Drugs 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
150000003555 thioacetals Chemical class 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
JKVRTUCVPZTEQZ-UHFFFAOYSA-N tributyltin azide Chemical compound CCCC[Sn](CCCC)(CCCC)N=[N+]=[N-] JKVRTUCVPZTEQZ-UHFFFAOYSA-N 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
230000007306 turnover Effects 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical class [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1
229960003414 zomepirac Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D215/16—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
- C07D215/18—Halogen atoms or nitro radicals
- 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
- C07D215/36—Sulfur 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pulmonology (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DK072287A 1986-02-14 1987-02-13 Quinolinderivat og farmaceutisk præparat indeholdende et sådant derivat DK168534B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA501932		1986-02-14
CA501932		1986-02-14

Publications (3)

Publication Number	Publication Date
DK72287D0 DK72287D0 (da)	1987-02-13
DK72287A DK72287A (da)	1987-08-15
DK168534B1 true DK168534B1 (da)	1994-04-18

Family

ID=4132478

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK072287A DK168534B1 (da)	1986-02-14	1987-02-13	Quinolinderivat og farmaceutisk præparat indeholdende et sådant derivat

Country Status (14)

Country	Link
EP (1)	EP0233763B1 (de)
JP (1)	JPH0686432B2 (de)
KR (1)	KR870007920A (de)
AT (1)	ATE60584T1 (de)
AU (1)	AU595286B2 (de)
DE (1)	DE3767730D1 (de)
DK (1)	DK168534B1 (de)
ES (1)	ES2031498T3 (de)
GR (1)	GR3001474T3 (de)
IE (1)	IE59889B1 (de)
IL (1)	IL81569A (de)
NZ (1)	NZ219249A (de)
PT (1)	PT84287B (de)
ZA (1)	ZA871064B (de)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0271287A3 (de) *	1986-12-11	1990-06-13	Merck Frosst Canada Inc.	Chinolindicarbonsäuren und ihre Amide
US4920132A (en) *	1987-11-03	1990-04-24	Rorer Pharmaceutical Corp.	Quinoline derivatives and use thereof as antagonists of leukotriene D4
US4920130A (en) *	1987-11-02	1990-04-24	Rorer Pharamceutical Corp.	Quinoline derivatives and use thereof as antagonists of leukotriene D4
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
IL88433A0 (en) *	1987-11-25	1989-06-30	Merck Frosst Canada Inc	Diarylstyrylquinoline diacids and pharmaceutical compositions containing them
US5004743A (en) *	1987-11-25	1991-04-02	Merck Frosst Canada, Inc.	Pyridyl styrene dialkanoic acids as anti-leukotriene agents
AU617386B2 (en) *	1987-12-01	1991-11-28	Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)	Substituted quinolines
GB8728051D0 (en) *	1987-12-01	1988-01-06	Leo Pharm Prod Ltd	Chemical compounds
US4883878A (en) *	1988-02-08	1989-11-28	Merck & Co. Inc.	Process for unsymmetrical dithioacetals and dithioketals
EP0349062A1 (de) *	1988-06-27	1990-01-03	Merck Frosst Canada Inc.	Chinolinetheralkansäuren
US5070022A (en) *	1988-12-22	1991-12-03	Merck & Co., Inc.	Enzymic process for preparing leukotriene antagonists
NZ233752A (en) *	1989-05-24	1993-05-26	Merck Frosst Canada Inc	Substituted quinoline derivatives, preparation and pharmaceutical compositions thereof
US4996214A (en) *	1990-06-28	1991-02-26	Smithkline Beecham Corporation	Quinolinyl substituted phenyl/thioalkanoic acid substituted propionic acids and leucotriene antagonist use thereof
US5428033A (en)	1990-10-12	1995-06-27	Merck Frosst Canada, Inc.	Saturated hydroxyalkylquinoline acids as leukotriene antagonists
US5856322A (en) *	1990-10-12	1999-01-05	Merck Frosst Canada, Inc.	Unsaturated hydroxyalkylquinoline acids as leukotriene antagonists
CA2053209C (en) *	1990-10-12	1998-12-08	Michel L. Belley	Unsaturated hydroxyalkylquinoline acids as leukotriene antagonists
US5266568A (en) *	1990-10-12	1993-11-30	Merck Frosst Canada, Inc.	Hydroxyalkylquinoline ether acids as leukotriene antagonists
ATE128969T1 (de) *	1990-10-12	1995-10-15	Merck Frosst Canada Inc	Hydroxyalkylchinolin äther säure als leukotrien- antagoniste.
IE920499A1 (en) *	1991-02-21	1992-08-26	Merck Frosst Canada Inc	Quinoline-containing ketoacids as leukotriene antagonists
US5212180A (en) *	1991-02-21	1993-05-18	Merck Frosst Canada, Inc.	Quinoline-containing ketoacids as leukotriene antagonists
US5276044A (en) *	1991-08-14	1994-01-04	Allergan, Inc.	Leukotriene receptor antagonist and antihistamine complex pharmaceutical compositions
US5270324A (en) *	1992-04-10	1993-12-14	Merck Frosst Canada, Inc.	Fluorinated hydroxyalkylquinoline acids as leukotriene antagonists
AU4413893A (en) *	1992-06-22	1994-01-24	Merck Frosst Canada Inc.	Fluorinated quinoline indoles as inhibitors of the biosynthesis of leukotrienes
US5964261A (en) *	1996-05-29	1999-10-12	Baxter International Inc.	Implantation assembly
WO2001047889A1 (en) *	1999-12-28	2001-07-05	Ube Industries, Ltd.	Tricyclic compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE56702B1 (en) *	1982-12-01	1991-11-06	Usv Pharma Corp	Antiinflammatory antiallergic compounds
US4625034A (en) *	1985-02-04	1986-11-25	Usv Pharmaceutical Corp.	1,2-Dihydro; 1,2,3,4-tetrahydro; 5,8 dihydro; and 5,6,7,8-tetrahydroquinoline derivatives
DK282986A (da) *	1985-06-18	1987-02-24	Merck Frosst Canada Inc	Substitueret quinolin og farmaceutisk praeparat indeholdende en saadan forbindelse

1987
- 1987-02-09 IE IE33487A patent/IE59889B1/en not_active IP Right Cessation
- 1987-02-12 AU AU68717/87A patent/AU595286B2/en not_active Ceased
- 1987-02-12 NZ NZ219249A patent/NZ219249A/xx unknown
- 1987-02-13 ES ES198787301256T patent/ES2031498T3/es not_active Expired - Lifetime
- 1987-02-13 IL IL81569A patent/IL81569A/xx not_active IP Right Cessation
- 1987-02-13 DK DK072287A patent/DK168534B1/da not_active IP Right Cessation
- 1987-02-13 EP EP87301256A patent/EP0233763B1/de not_active Expired - Lifetime
- 1987-02-13 ZA ZA871064A patent/ZA871064B/xx unknown
- 1987-02-13 DE DE8787301256T patent/DE3767730D1/de not_active Expired - Lifetime
- 1987-02-13 AT AT87301256T patent/ATE60584T1/de not_active IP Right Cessation
- 1987-02-13 PT PT84287A patent/PT84287B/pt not_active IP Right Cessation
- 1987-02-13 KR KR870001190A patent/KR870007920A/ko not_active Ceased
- 1987-02-14 JP JP62032282A patent/JPH0686432B2/ja not_active Expired - Fee Related
1991
- 1991-02-13 GR GR91400190T patent/GR3001474T3/el unknown

Also Published As

Publication number	Publication date
IE870334L (en)	1987-08-14
IL81569A0 (en)	1987-09-16
EP0233763A3 (en)	1988-10-19
DK72287A (da)	1987-08-15
IL81569A (en)	1991-11-21
IE59889B1 (en)	1994-04-20
ZA871064B (en)	1987-10-28
NZ219249A (en)	1990-07-26
EP0233763B1 (de)	1991-01-30
ATE60584T1 (de)	1991-02-15
DK72287D0 (da)	1987-02-13
PT84287B (pt)	1989-09-14
EP0233763A2 (de)	1987-08-26
GR3001474T3 (en)	1992-10-08
PT84287A (en)	1987-03-01
DE3767730D1 (de)	1991-03-07
AU6871787A (en)	1987-08-20
ES2031498T3 (es)	1992-12-16
JPH0686432B2 (ja)	1994-11-02
JPS62258363A (ja)	1987-11-10
AU595286B2 (en)	1990-03-29
KR870007920A (ko)	1987-09-22

Legal Events

Date	Code	Title	Description
1994-04-18	B1	Patent granted (law 1993)
2004-09-27	PBP	Patent lapsed	Country of ref document: DK

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