NO865233L - Aromatiske tioetere. - Google Patents
Aromatiske tioetere.Info
- Publication number
- NO865233L NO865233L NO865233A NO865233A NO865233L NO 865233 L NO865233 L NO 865233L NO 865233 A NO865233 A NO 865233A NO 865233 A NO865233 A NO 865233A NO 865233 L NO865233 L NO 865233L
- Authority
- NO
- Norway
- Prior art keywords
- trans
- cis
- formula
- methyl ester
- hydrogen
- Prior art date
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
- 239000001257 hydrogen Substances 0.000 claims abstract description 44
- -1 X represents NH Inorganic materials 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
- 230000036961 partial effect Effects 0.000 claims abstract description 20
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 16
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000005977 Ethylene Substances 0.000 claims abstract description 6
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 192
- 238000000034 method Methods 0.000 claims description 23
- 239000013543 active substance Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 150000002617 leukotrienes Chemical class 0.000 claims description 15
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 230000035876 healing Effects 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 102000015439 Phospholipases Human genes 0.000 claims description 3
- 108010064785 Phospholipases Proteins 0.000 claims description 3
- 230000002009 allergenic effect Effects 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 208000024891 symptom Diseases 0.000 claims description 3
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 claims 1
- 230000008602 contraction Effects 0.000 abstract description 6
- 208000006673 asthma Diseases 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- 210000002460 smooth muscle Anatomy 0.000 abstract description 3
- 150000003568 thioethers Chemical class 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 230000000172 allergic effect Effects 0.000 abstract 1
- 239000005557 antagonist Substances 0.000 abstract 1
- 208000010668 atopic eczema Diseases 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 98
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 96
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 88
- 239000000243 solution Substances 0.000 description 88
- 239000000203 mixture Substances 0.000 description 69
- 150000004702 methyl esters Chemical class 0.000 description 55
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 238000002844 melting Methods 0.000 description 41
- 230000008018 melting Effects 0.000 description 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
- 239000000741 silica gel Substances 0.000 description 40
- 229910002027 silica gel Inorganic materials 0.000 description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 239000000460 chlorine Substances 0.000 description 38
- 239000007858 starting material Substances 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000012230 colorless oil Substances 0.000 description 25
- MXOMLDWEYREFGE-UHFFFAOYSA-N methyl 4-oxo-7-sulfanylchromene-2-carboxylate Chemical compound C1=C(S)C=C2OC(C(=O)OC)=CC(=O)C2=C1 MXOMLDWEYREFGE-UHFFFAOYSA-N 0.000 description 25
- 239000007787 solid Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 238000004587 chromatography analysis Methods 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 11
- 150000002924 oxiranes Chemical class 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- OMEKDSOPAQTUMQ-UHFFFAOYSA-N methyl 2-methoxy-7-sulfanylquinoline-3-carboxylate Chemical compound C1=C(S)C=C2N=C(OC)C(C(=O)OC)=CC2=C1 OMEKDSOPAQTUMQ-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- 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 8
- 238000009835 boiling Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 7
- 239000008363 phosphate buffer Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- UZHPFPZUOUVGSW-UHFFFAOYSA-N 1-bromo-2-nonylbenzene Chemical compound CCCCCCCCCC1=CC=CC=C1Br UZHPFPZUOUVGSW-UHFFFAOYSA-N 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000000443 aerosol Substances 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 159000000001 potassium salts Chemical class 0.000 description 5
- 239000003380 propellant Substances 0.000 description 5
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 5
- HDQDUBPEBVXIBJ-VOTSOKGWSA-N (e)-hept-1-en-1-ol Chemical compound CCCCC\C=C\O HDQDUBPEBVXIBJ-VOTSOKGWSA-N 0.000 description 4
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 4
- CQCAYWAIRTVXIY-UHFFFAOYSA-N 2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC=O)C1=CC=CC=C1 CQCAYWAIRTVXIY-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 238000011097 chromatography purification Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- IKAWSKLBMOKONC-UHFFFAOYSA-M (2-nonylphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].CCCCCCCCCC1=CC=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IKAWSKLBMOKONC-UHFFFAOYSA-M 0.000 description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- ZXHBYZZFRUXRBZ-UHFFFAOYSA-N 1-(bromomethyl)-2-nonylbenzene Chemical compound CCCCCCCCCC1=CC=CC=C1CBr ZXHBYZZFRUXRBZ-UHFFFAOYSA-N 0.000 description 3
- DATZZDBUDVRTBB-FOWTUZBSSA-N 1-[(e)-hex-1-enyl]-2-nonylbenzene Chemical compound CCCCCCCCCC1=CC=CC=C1\C=C\CCCC DATZZDBUDVRTBB-FOWTUZBSSA-N 0.000 description 3
- RDQBRQLAQPYNTD-UHFFFAOYSA-N 2-nonylbenzaldehyde Chemical compound CCCCCCCCCC1=CC=CC=C1C=O RDQBRQLAQPYNTD-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000003266 anti-allergic effect Effects 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 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
- 238000004821 distillation Methods 0.000 description 3
- 239000006196 drop Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 3
- GGFYMBPIQJXVRJ-QHHAFSJGSA-N (e)-3-[3-(trifluoromethyl)phenyl]prop-1-en-1-ol Chemical compound O\C=C\CC1=CC=CC(C(F)(F)F)=C1 GGFYMBPIQJXVRJ-QHHAFSJGSA-N 0.000 description 2
- LXQASESBXFPJNN-HWKANZROSA-N (e)-6,6,6-trifluorohex-1-en-1-ol Chemical compound O\C=C\CCCC(F)(F)F LXQASESBXFPJNN-HWKANZROSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UTUJNFLIMLQDNW-UHFFFAOYSA-N 1-(2-nonylphenyl)hexan-1-ol Chemical compound CCCCCCCCCC1=CC=CC=C1C(O)CCCCC UTUJNFLIMLQDNW-UHFFFAOYSA-N 0.000 description 2
- AKTUFAQIBBPMPY-LFIBNONCSA-N 1-[(e)-4-chlorobut-1-enyl]-2-nonylbenzene Chemical compound CCCCCCCCCC1=CC=CC=C1\C=C\CCCl AKTUFAQIBBPMPY-LFIBNONCSA-N 0.000 description 2
- PTFMGWWPGNHIEA-LFIBNONCSA-N 1-[(e)-6-fluorohex-1-enyl]-2-nonylbenzene Chemical compound CCCCCCCCCC1=CC=CC=C1\C=C\CCCCF PTFMGWWPGNHIEA-LFIBNONCSA-N 0.000 description 2
- MCHQFNGACWWUEN-UHFFFAOYSA-N 1-bromo-3-nonylbenzene Chemical compound CCCCCCCCCC1=CC=CC(Br)=C1 MCHQFNGACWWUEN-UHFFFAOYSA-N 0.000 description 2
- BDVSKSFRBFPOTO-UHFFFAOYSA-N 1-hex-1-enyl-4-nonylbenzene Chemical compound CCCCCCCCCC1=CC=C(C=CCCCC)C=C1 BDVSKSFRBFPOTO-UHFFFAOYSA-N 0.000 description 2
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/19—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 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 in position 2
-
- 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
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH551385 | 1985-12-23 | ||
| CH132186 | 1986-04-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO865233D0 NO865233D0 (no) | 1986-12-22 |
| NO865233L true NO865233L (no) | 1987-06-24 |
Family
ID=25687324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO865233A NO865233L (no) | 1985-12-23 | 1986-12-22 | Aromatiske tioetere. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4785004A (fr) |
| EP (1) | EP0228045B1 (fr) |
| KR (1) | KR870005986A (fr) |
| AT (1) | ATE62223T1 (fr) |
| AU (1) | AU6681786A (fr) |
| CA (1) | CA1274522A (fr) |
| DE (1) | DE3678545D1 (fr) |
| DK (1) | DK624286A (fr) |
| ES (1) | ES2044834T3 (fr) |
| FI (1) | FI865241A (fr) |
| GR (1) | GR3001727T3 (fr) |
| HU (1) | HUT46658A (fr) |
| IL (1) | IL81056A0 (fr) |
| NO (1) | NO865233L (fr) |
| NZ (1) | NZ218762A (fr) |
| PT (1) | PT83992B (fr) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5017583A (en) * | 1983-04-21 | 1991-05-21 | Merck Frosst Canada, Inc. | Leukotriene antagonists |
| GB8523776D0 (en) * | 1985-09-26 | 1985-10-30 | Scras | Catechol derivatives |
| GB8709546D0 (en) * | 1987-04-22 | 1987-05-28 | Lilly Industries Ltd | Pharmaceutical use of organic compounds |
| GB8709547D0 (en) * | 1987-04-22 | 1987-05-28 | Lilly Industries Ltd | Organic compounds |
| DE3724735A1 (de) * | 1987-07-25 | 1989-02-02 | Hoechst Ag | Leukotrienantagonisten, verfahren zu ihrer herstellung, ihre anwendung zur behandlung von krankheiten, sowie vorprodukte |
| DE3724669A1 (de) * | 1987-07-25 | 1989-02-02 | Hoechst Ag | Leukotrienantagonisten, verfahren zu ihrer herstellung und ihre anwendung zur behandlung von krankheiten |
| GB8725260D0 (en) * | 1987-10-28 | 1987-12-02 | Lilly Industries Ltd | Organic compounds |
| GB8807016D0 (en) * | 1988-03-24 | 1988-04-27 | Lilly Industries Ltd | Organic compounds & their pharmaceutical use |
| FI94342C (fi) * | 1988-03-29 | 1995-08-25 | Ciba Geigy Ag | Menetelmä uusien alkanofenonien valmistamiseksi |
| US5149717A (en) * | 1988-03-29 | 1992-09-22 | Ciba-Geigy Corporation | Alkanophenones useful for treating allergies |
| IL93765A (en) * | 1989-04-11 | 1995-08-31 | Basf Ag | Oxirane Phenyl Esters and fungicides containing them |
| EP0419411A3 (en) * | 1989-09-19 | 1991-09-04 | Ciba-Geigy Ag | Additional alkanophenones |
| EP0419410A3 (en) * | 1989-09-19 | 1991-08-14 | Ciba-Geigy Ag | Alkanophenones |
| GB9015892D0 (en) * | 1990-07-19 | 1990-09-05 | Tioxide Group Services Ltd | Compositions |
| EP3133067A1 (fr) | 2015-08-21 | 2017-02-22 | Merck Patent GmbH | Composés de dispositifs optiquement actifs |
| EP3133066A1 (fr) | 2015-08-21 | 2017-02-22 | Merck Patent GmbH | Composés hydrophiles pour dispositifs optiquement actifs |
| EP3133065A1 (fr) | 2015-08-21 | 2017-02-22 | Merck Patent GmbH | Composés de dispositifs optiquement actifs |
| EP3363786A1 (fr) | 2017-02-15 | 2018-08-22 | Merck Patent GmbH | Composés de dispositifs optiquement actifs |
| EP3363793A1 (fr) | 2017-02-15 | 2018-08-22 | Merck Patent GmbH | Composés hydrophobes pour dispositifs optiquement actifs |
| US20210355113A1 (en) | 2018-07-23 | 2021-11-18 | Bristol-Myers Squibb Company | Inhibitors of indoleamine 2,3-dioxygenase and methods of their use |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0123543B1 (fr) * | 1983-04-21 | 1988-02-03 | Merck Frosst Canada Inc. | Antagonistes du leucotriène, leur préparation, leur utilisation et compositions les contenant |
| US4609744A (en) * | 1983-04-21 | 1986-09-02 | Merck Frosst Canada Inc. | 4-oxo-benzopyran carboxylic acids |
| GB8320943D0 (en) * | 1983-08-03 | 1983-09-07 | Lilly Industries Ltd | Organic compounds |
| IL75620A (en) * | 1984-06-28 | 1989-05-15 | Ciba Geigy | Aliphatic thioethers of alkanoic acid derivatives,their manufacture and pharmaceutical compositions containing them |
-
1986
- 1986-12-15 US US06/941,676 patent/US4785004A/en not_active Expired - Fee Related
- 1986-12-19 CA CA000525826A patent/CA1274522A/fr not_active Expired - Lifetime
- 1986-12-19 ES ES86117740T patent/ES2044834T3/es not_active Expired - Lifetime
- 1986-12-19 EP EP86117740A patent/EP0228045B1/fr not_active Expired - Lifetime
- 1986-12-19 FI FI865241A patent/FI865241A/fi not_active IP Right Cessation
- 1986-12-19 AT AT86117740T patent/ATE62223T1/de not_active IP Right Cessation
- 1986-12-19 DE DE8686117740T patent/DE3678545D1/de not_active Expired - Lifetime
- 1986-12-22 AU AU66817/86A patent/AU6681786A/en not_active Abandoned
- 1986-12-22 IL IL81056A patent/IL81056A0/xx unknown
- 1986-12-22 HU HU865384A patent/HUT46658A/hu unknown
- 1986-12-22 NZ NZ218762A patent/NZ218762A/xx unknown
- 1986-12-22 DK DK624286A patent/DK624286A/da not_active Application Discontinuation
- 1986-12-22 PT PT83992A patent/PT83992B/pt not_active IP Right Cessation
- 1986-12-22 NO NO865233A patent/NO865233L/no unknown
- 1986-12-23 KR KR860011119A patent/KR870005986A/ko not_active Application Discontinuation
-
1991
- 1991-04-04 GR GR90401112T patent/GR3001727T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO865233D0 (no) | 1986-12-22 |
| FI865241A (fi) | 1987-06-24 |
| EP0228045B1 (fr) | 1991-04-03 |
| KR870005986A (ko) | 1987-07-08 |
| DK624286D0 (da) | 1986-12-22 |
| GR3001727T3 (en) | 1992-11-23 |
| HUT46658A (en) | 1988-11-28 |
| EP0228045A2 (fr) | 1987-07-08 |
| NZ218762A (en) | 1989-01-27 |
| FI865241A0 (fi) | 1986-12-19 |
| EP0228045A3 (en) | 1988-09-07 |
| ES2044834T3 (es) | 1994-01-16 |
| DE3678545D1 (en) | 1991-05-08 |
| US4785004A (en) | 1988-11-15 |
| ATE62223T1 (de) | 1991-04-15 |
| IL81056A0 (en) | 1987-03-31 |
| CA1274522A (fr) | 1990-09-25 |
| DK624286A (da) | 1987-06-24 |
| AU6681786A (en) | 1987-06-25 |
| PT83992A (de) | 1987-01-01 |
| PT83992B (pt) | 1989-07-31 |
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