CA1337196C - Derives de substitution en 2 d'acides quinoleinedioiques - Google Patents

Derives de substitution en 2 d'acides quinoleinedioiques

Info

Publication number: CA1337196C
Authority: CA; Canada
Prior art keywords: cooh; phenyl; chloroquinolin; compound; ch2o
Prior art date: 1986-02-14
Legal status (The legal status 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 status listed.): Expired - Fee Related

Application number

CA 529092

Other languages

English (en)

Inventor

Robert N. Young

Robert Zamboni

Serge Leger

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Merck Frosst Canada and Co

Original Assignee

Merck Frosst Canada and Co

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

1987-02-05

Publication date

1995-10-03

1987-02-05 Application filed by Merck Frosst Canada and Co filed Critical Merck Frosst Canada and Co

1995-10-03 Application granted granted Critical

1995-10-03 Publication of CA1337196C publication Critical patent/CA1337196C/fr

2012-10-03 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

-1 2-substituted quinoline dioic acids Chemical class 0.000 title claims description 23
150000001875 compounds Chemical class 0.000 claims abstract description 165
150000002617 leukotrienes Chemical class 0.000 claims abstract description 13
230000015572 biosynthetic process Effects 0.000 claims abstract description 9
239000005557 antagonist Substances 0.000 claims abstract description 7
239000002253 acid Substances 0.000 claims description 56
239000000203 mixture Substances 0.000 claims description 53
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
241000124008 Mammalia Species 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 19
239000004480 active ingredient Substances 0.000 claims description 18
229910052760 oxygen Inorganic materials 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 14
239000008194 pharmaceutical composition Substances 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
229910020008 S(O) Inorganic materials 0.000 claims description 10
239000003937 drug carrier Substances 0.000 claims description 10
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 claims description 9
150000003536 tetrazoles Chemical class 0.000 claims description 9
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 8
239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 8
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 8
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 claims description 8
208000027866 inflammatory disease Diseases 0.000 claims description 7
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
230000001939 inductive effect Effects 0.000 claims description 6
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 claims description 6
150000003254 radicals Chemical class 0.000 claims description 6
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
229960000905 indomethacin Drugs 0.000 claims description 4
150000001413 amino acids Chemical class 0.000 claims description 3
229940082988 antihypertensives serotonin antagonists Drugs 0.000 claims description 3
239000003420 antiserotonin agent Substances 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
125000002015 acyclic group Chemical group 0.000 claims description 2
239000000730 antalgic agent Substances 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
229930195733 hydrocarbon Natural products 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
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 claims description 2
XNAYQOBPAXEYLI-UHFFFAOYSA-M sodium;3-[[3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-[3-(dimethylamino)-3-oxopropyl]sulfanylmethyl]sulfanylpropanoate Chemical compound [Na+].CN(C)C(=O)CCSC(SCCC([O-])=O)C1=CC=CC(C=CC=2N=C3C=C(Cl)C=CC3=CC=2)=C1 XNAYQOBPAXEYLI-UHFFFAOYSA-M 0.000 claims 6
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 5
238000003786 synthesis reaction Methods 0.000 claims 5
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
229940125715 antihistaminic agent Drugs 0.000 claims 1
239000000739 antihistaminic agent Substances 0.000 claims 1
229940077716 histamine h2 receptor antagonists for peptic ulcer and gord Drugs 0.000 claims 1
159000000000 sodium salts Chemical class 0.000 claims 1
230000001120 cytoprotective effect Effects 0.000 abstract description 8
230000003266 anti-allergic effect Effects 0.000 abstract description 6
239000003795 chemical substances by application Substances 0.000 abstract description 6
230000001088 anti-asthma Effects 0.000 abstract description 5
230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
239000000924 antiasthmatic agent Substances 0.000 abstract description 5
239000003112 inhibitor Substances 0.000 abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 188
VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 98
239000000243 solution Substances 0.000 description 91
235000019439 ethyl acetate Nutrition 0.000 description 70
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
229940093499 ethyl acetate Drugs 0.000 description 47
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
238000006243 chemical reaction Methods 0.000 description 41
238000003818 flash chromatography Methods 0.000 description 40
238000000034 method Methods 0.000 description 40
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 34
239000011541 reaction mixture Substances 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
229910052938 sodium sulfate Inorganic materials 0.000 description 30
235000011152 sodium sulphate Nutrition 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000000725 suspension Substances 0.000 description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 20
235000019441 ethanol Nutrition 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000012267 brine Substances 0.000 description 15
239000012044 organic layer Substances 0.000 description 15
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 14
238000000746 purification Methods 0.000 description 14
239000007787 solid Substances 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
239000011701 zinc Substances 0.000 description 11
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
235000019257 ammonium acetate Nutrition 0.000 description 10
229940043376 ammonium acetate Drugs 0.000 description 10
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical class C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 10
239000000377 silicon dioxide Substances 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
150000001299 aldehydes Chemical class 0.000 description 9
239000000872 buffer Substances 0.000 description 9
239000003826 tablet Substances 0.000 description 9
WQZQFYRSYLXBGP-UHFFFAOYSA-N 7-chloro-2-methylquinoline Chemical compound C1=CC(Cl)=CC2=NC(C)=CC=C21 WQZQFYRSYLXBGP-UHFFFAOYSA-N 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
239000003921 oil Substances 0.000 description 8
238000010992 reflux Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000003756 stirring Methods 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
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 7
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
150000005690 diesters Chemical class 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
238000000605 extraction Methods 0.000 description 7
235000019256 formaldehyde Nutrition 0.000 description 7
239000007788 liquid Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
239000007832 Na2SO4 Substances 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
230000006378 damage Effects 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000000843 powder Substances 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
125000000217 alkyl group Chemical group 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
230000037396 body weight Effects 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000001914 filtration Methods 0.000 description 5
LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 description 5
229910000027 potassium carbonate Inorganic materials 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
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 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
241000282414 Homo sapiens Species 0.000 description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000003556 assay Methods 0.000 description 4
239000011575 calcium Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000004615 ingredient 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
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 4
CELCCNILIIJXNW-UHFFFAOYSA-N methyl 3-[[3-[[tert-butyl(diphenyl)silyl]oxymethyl]phenyl]-[3-(dimethylamino)-3-oxopropyl]sulfanylmethyl]sulfanylpropanoate Chemical compound COC(=O)CCSC(SCCC(=O)N(C)C)C1=CC=CC(CO[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C(C)(C)C)=C1 CELCCNILIIJXNW-UHFFFAOYSA-N 0.000 description 4
UXBJXJHRVOEYPA-UHFFFAOYSA-N n,n-dimethyl-3-sulfanylpropanamide Chemical compound CN(C)C(=O)CCS UXBJXJHRVOEYPA-UHFFFAOYSA-N 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
239000000047 product Substances 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 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
229910015900 BF3 Inorganic materials 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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
239000004471 Glycine Substances 0.000 description 3
241000282412 Homo Species 0.000 description 3
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
239000004472 Lysine Substances 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
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Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA 529092 1986-02-14 1987-02-05 Derives de substitution en 2 d'acides quinoleinedioiques Expired - Fee Related CA1337196C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US82967986A	1986-02-14	1986-02-14
US829,679		1986-02-14

Publications (1)

Publication Number	Publication Date
CA1337196C true CA1337196C (fr)	1995-10-03

Family

ID=25255221

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 529092 Expired - Fee Related CA1337196C (fr)	1986-02-14	1987-02-05	Derives de substitution en 2 d'acides quinoleinedioiques

Country Status (1)

Country	Link
CA (1)	CA1337196C (fr)

1987
- 1987-02-05 CA CA 529092 patent/CA1337196C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
2004-10-04	MKLA	Lapsed

Publication	Publication Date	Title
EP0233763B1 (fr)	1991-01-30	Acides quinoléine-2-dioiques
US4851409A (en)	1989-07-25	2-substituted quinoline dioic acids and pharmaceutical compositions
JP2501385B2 (ja)	1996-05-29	ロイコトリエン拮抗剤としての不飽和ヒドロキシアルキルキノリン酸
CA1338352C (fr)	1996-05-28	Derives de substitution en 2 de quinoleines
CA1324143C (fr)	1993-11-09	Acides quinolinedioiques et leurs amides
EP0399818B1 (fr)	1995-08-16	Diacides dérivés de diarylstyrylquinoléine
US5270324A (en)	1993-12-14	Fluorinated hydroxyalkylquinoline acids as leukotriene antagonists
US5565473A (en)	1996-10-15	Unsaturated hydroxyalkylquinoline acids as leukotriene antagonists
JP2538155B2 (ja)	1996-09-25	ロイコトリエン拮抗剤としての飽和ヒドロキシアルキルキノリン酸類
JPH02138259A (ja)	1990-05-28	ジアリールスチリルキノリンジアシド類
JPH07121941B2 (ja)	1995-12-25	ロイコトリエンｄ▲下４▼拮抗剤としてのキノリニル―ベンゾヘテロ二環式誘導体
US5856322A (en)	1999-01-05	Unsaturated hydroxyalkylquinoline acids as leukotriene antagonists
CA1298838C (fr)	1992-04-14	Quinolines substituees en 2
US5104882A (en)	1992-04-14	Diarylstrylquinoline diacids and pharmaceutical compositions thereof
JP2538154B2 (ja)	1996-09-25	ロイコトリエン拮抗剤としてのヒドロキシアルキルキノリンエ―テル酸
CA1337196C (fr)	1995-10-03	Derives de substitution en 2 d'acides quinoleinedioiques
US5204358A (en)	1993-04-20	Hetaryl styryl quinolines as leukotriene inhibitors
US5428171A (en)	1995-06-27	2-substituted quinoline dioic acids
US5155130A (en)	1992-10-13	Certain benzopyran and benzothiopyran derivatives