IE45905B1 - Substituted furan and thiophen alkyl ketones - Google Patents
Substituted furan and thiophen alkyl ketonesInfo
- Publication number
- IE45905B1 IE45905B1 IE2306/77A IE230677A IE45905B1 IE 45905 B1 IE45905 B1 IE 45905B1 IE 2306/77 A IE2306/77 A IE 2306/77A IE 230677 A IE230677 A IE 230677A IE 45905 B1 IE45905 B1 IE 45905B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- methyl
- carbon atoms
- composition
- ketone
- Prior art date
Links
- -1 thiophen alkyl ketones Chemical class 0.000 title description 40
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title description 18
- 150000002240 furans Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000005864 Sulphur Chemical group 0.000 claims description 6
- LVBMQDHWDJBTTC-UHFFFAOYSA-N 1-(2-tetradecan-5-yloxyfuran-3-yl)ethanone Chemical compound CCCCC(CCCCCCCCC)OC=1OC=CC1C(=O)C LVBMQDHWDJBTTC-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 4
- SJGJABAAGGZYSW-UHFFFAOYSA-N 1-(2-dodecan-5-yloxyfuran-3-yl)ethanone Chemical compound CCCCC(CCCCCCC)OC=1OC=CC1C(=O)C SJGJABAAGGZYSW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 230000002128 anti-rhinoviral effect Effects 0.000 abstract description 8
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 239000011593 sulfur Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 241000700605 Viruses Species 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229930192474 thiophene Natural products 0.000 description 9
- 241000709661 Enterovirus Species 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
- 229920002261 Corn starch Polymers 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 206010061494 Rhinovirus infection Diseases 0.000 description 7
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 7
- 239000008120 corn starch Substances 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 6
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical class OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 238000004113 cell culture Methods 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- CZRCFAOMWRAFIC-UHFFFAOYSA-N 5-(tetradecyloxy)-2-furoic acid Chemical compound CCCCCCCCCCCCCCOC1=CC=C(C(O)=O)O1 CZRCFAOMWRAFIC-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000008101 lactose Substances 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
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 150000003577 thiophenes Chemical class 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OUFCBWUQONVGEV-UHFFFAOYSA-N 2-tetradecan-5-yloxy-3h-thiophene-2-carboxylic acid Chemical compound CCCCCCCCCC(CCCC)OC1(C(O)=O)CC=CS1 OUFCBWUQONVGEV-UHFFFAOYSA-N 0.000 description 3
- YVTQHZDUDUCGRD-UHFFFAOYSA-N 5-bromofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)O1 YVTQHZDUDUCGRD-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000019483 Peanut oil Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000010255 intramuscular injection Methods 0.000 description 3
- 239000007927 intramuscular injection Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000000312 peanut oil Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000008159 sesame oil Substances 0.000 description 3
- 235000011803 sesame oil Nutrition 0.000 description 3
- 239000007892 solid unit dosage form Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical class OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 3
- NYQPXXUHOOHJNZ-UHFFFAOYSA-N 1-(2-tetradecan-5-yloxythiophen-3-yl)pentan-1-one Chemical compound CCCCC(CCCCCCCCC)OC=1SC=CC1C(=O)CCCC NYQPXXUHOOHJNZ-UHFFFAOYSA-N 0.000 description 2
- WJWYHVZQOBEAJD-UHFFFAOYSA-N 1-(2-tetradecan-5-ylsulfanylthiophen-3-yl)ethanone Chemical compound CCCCC(CCCCCCCCC)SC=1SC=CC1C(=O)C WJWYHVZQOBEAJD-UHFFFAOYSA-N 0.000 description 2
- IGXWEUNEYDVFAS-KHPPLWFESA-N 1-[5-[(z)-octadec-9-enoxy]furan-2-yl]ethanone Chemical compound CCCCCCCC\C=C/CCCCCCCCOC1=CC=C(C(C)=O)O1 IGXWEUNEYDVFAS-KHPPLWFESA-N 0.000 description 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 2
- DOJYADCDQKSTCS-UHFFFAOYSA-N 2-tetradecan-5-ylsulfanyl-3h-thiophene-2-carboxylic acid Chemical compound CCCCCCCCCC(CCCC)SC1(C(O)=O)CC=CS1 DOJYADCDQKSTCS-UHFFFAOYSA-N 0.000 description 2
- NMSLUAZZTFUUFZ-UHFFFAOYSA-N 2h-thiophen-5-one Chemical compound O=C1SCC=C1 NMSLUAZZTFUUFZ-UHFFFAOYSA-N 0.000 description 2
- VIAGKGWEEIQNFP-KTKRTIGZSA-N 5-[(z)-octadec-9-enoxy]furan-2-carboxylic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCOC1=CC=C(C(O)=O)O1 VIAGKGWEEIQNFP-KTKRTIGZSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 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 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000003524 antilipemic agent Substances 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- GUTQMBQKTSGBPQ-UHFFFAOYSA-N dithiophen-2-ylmethanone Chemical compound C=1C=CSC=1C(=O)C1=CC=CS1 GUTQMBQKTSGBPQ-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000007928 imidazolide derivatives Chemical class 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 210000003928 nasal cavity Anatomy 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- ZRPBDWAWDGMIDV-UHFFFAOYSA-N 1-(2-decan-3-ylsulfanylthiophen-3-yl)ethanone Chemical compound CCC(CCCCCCC)SC=1SC=CC=1C(=O)C ZRPBDWAWDGMIDV-UHFFFAOYSA-N 0.000 description 1
- BYXKRMOHQGEZAV-UHFFFAOYSA-N 1-(2-decan-4-ylsulfanylfuran-3-yl)butan-1-one Chemical compound CCCC(CCCCCC)SC=1OC=CC1C(=O)CCC BYXKRMOHQGEZAV-UHFFFAOYSA-N 0.000 description 1
- ROWUCQXWFBWDPW-UHFFFAOYSA-N 1-(2-decan-4-ylsulfanylthiophen-3-yl)butan-1-one Chemical compound CCCC(CCCCCC)SC=1SC=CC1C(=O)CCC ROWUCQXWFBWDPW-UHFFFAOYSA-N 0.000 description 1
- KEXXPVAIJFIFTN-UHFFFAOYSA-N 1-(2-dodecan-5-ylfuran-3-yl)propan-1-one Chemical compound CCCCC(CCCCCCC)C=1OC=CC1C(=O)CC KEXXPVAIJFIFTN-UHFFFAOYSA-N 0.000 description 1
- XWYLXTHQZABJKN-UHFFFAOYSA-N 1-(2-dodecan-5-yloxyfuran-3-yl)propan-1-one Chemical compound CCCCC(CCCCCCC)OC=1OC=CC1C(=O)CC XWYLXTHQZABJKN-UHFFFAOYSA-N 0.000 description 1
- XSWHHWHOPRADBY-UHFFFAOYSA-N 1-(2-dodecan-5-yloxythiophen-3-yl)propan-1-one Chemical compound CCCCC(CCCCCCC)OC=1SC=CC1C(=O)CC XSWHHWHOPRADBY-UHFFFAOYSA-N 0.000 description 1
- MNHUDLXNDAMULW-UHFFFAOYSA-N 1-(2-dodecan-5-ylsulfanylthiophen-3-yl)propan-1-one Chemical compound CCCCC(CCCCCCC)SC=1SC=CC1C(=O)CC MNHUDLXNDAMULW-UHFFFAOYSA-N 0.000 description 1
- INOSKVQHORWDEU-UHFFFAOYSA-N 1-(2-heptadecan-4-ylsulfanylthiophen-3-yl)-2,2-dimethylpropan-1-one Chemical compound CCCC(CCCCCCCCCCCCC)SC=1SC=CC1C(=O)C(C)(C)C INOSKVQHORWDEU-UHFFFAOYSA-N 0.000 description 1
- UCVFOXRKAPJBQX-UHFFFAOYSA-N 1-(2-octadecan-5-ylsulfanylthiophen-3-yl)ethanone Chemical compound CCCCC(CCCCCCCCCCCCC)SC=1SC=CC1C(=O)C UCVFOXRKAPJBQX-UHFFFAOYSA-N 0.000 description 1
- FFQVKEUYDGBYIH-UHFFFAOYSA-N 1-(2-pentadecan-5-yloxythiophen-3-yl)butan-1-one Chemical compound CCCCC(CCCCCCCCCC)OC=1SC=CC=1C(=O)CCC FFQVKEUYDGBYIH-UHFFFAOYSA-N 0.000 description 1
- WNMXUCLXPZACSR-UHFFFAOYSA-N 1-(2-tetradecan-5-ylfuran-3-yl)ethanone Chemical compound CCCCC(CCCCCCCCC)C=1OC=CC1C(=O)C WNMXUCLXPZACSR-UHFFFAOYSA-N 0.000 description 1
- DHOBZPRQSYKPGH-UHFFFAOYSA-N 1-(2-tetradecan-5-ylsulfanylfuran-3-yl)ethanone Chemical compound CCCCC(CCCCCCCCC)SC=1OC=CC1C(=O)C DHOBZPRQSYKPGH-UHFFFAOYSA-N 0.000 description 1
- MEBSTXDJDQIQTA-UHFFFAOYSA-N 1-(2-tridecan-3-ylthiophen-3-yl)pentan-1-one Chemical compound CCC(CCCCCCCCCC)C=1SC=CC1C(=O)CCCC MEBSTXDJDQIQTA-UHFFFAOYSA-N 0.000 description 1
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- LWLPYZUDBNFNAH-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CCC[CH2-] LWLPYZUDBNFNAH-UHFFFAOYSA-M 0.000 description 1
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- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
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- GEKDEMKPCKTKEC-UHFFFAOYSA-N tetradecane-1-thiol Chemical compound CCCCCCCCCCCCCCS GEKDEMKPCKTKEC-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- WHLUQAYNVOGZST-UHFFFAOYSA-N tifenamil Chemical class C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 WHLUQAYNVOGZST-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- 239000011592 zinc chloride Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/58—One oxygen atom, e.g. butenolide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75113976A | 1976-12-20 | 1976-12-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE45905L IE45905L (en) | 1978-06-20 |
| IE45905B1 true IE45905B1 (en) | 1982-12-29 |
Family
ID=25020661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2306/77A IE45905B1 (en) | 1976-12-20 | 1977-11-14 | Substituted furan and thiophen alkyl ketones |
Country Status (15)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0213066U (enrdf_load_stackoverflow) * | 1988-07-12 | 1990-01-26 | ||
| US4977185A (en) * | 1988-12-21 | 1990-12-11 | Merrell Dow Pharmaceuticals | Antiretroviral aryloxy substituted furan ketones |
| AU621434B2 (en) * | 1988-12-21 | 1992-03-12 | Merrell Dow Pharmaceuticals Inc. | Antiretroviral furan ketones |
| US4980371A (en) * | 1988-12-21 | 1990-12-25 | Merrell Dow Pharmaceuticals | Antiretroviral furan ketones |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2746973A (en) * | 1955-05-27 | 1956-05-22 | Du Pont | 5-alkylmercapto-2-heterocyclic aldehydes and ketones |
| US4000164A (en) * | 1973-04-02 | 1976-12-28 | Richardson-Merrell Inc. | Hypolipidemic agents |
-
1977
- 1977-11-07 CA CA290,375A patent/CA1104574A/en not_active Expired
- 1977-11-14 IE IE2306/77A patent/IE45905B1/en not_active IP Right Cessation
- 1977-11-15 NZ NZ185688A patent/NZ185688A/xx unknown
- 1977-11-15 ZA ZA00776821A patent/ZA776821B/xx unknown
- 1977-11-15 IL IL53386A patent/IL53386A0/xx unknown
- 1977-11-23 AU AU30867/77A patent/AU512654B2/en not_active Expired
- 1977-12-09 JP JP14733277A patent/JPS5377055A/ja active Granted
- 1977-12-14 DE DE19772755750 patent/DE2755750A1/de not_active Ceased
- 1977-12-14 SE SE7714210A patent/SE436878B/sv not_active IP Right Cessation
- 1977-12-14 NL NL7713825A patent/NL7713825A/xx not_active Application Discontinuation
- 1977-12-15 GB GB52182/77A patent/GB1539636A/en not_active Expired
- 1977-12-15 ES ES465093A patent/ES465093A1/es not_active Expired
- 1977-12-19 DK DK564977A patent/DK564977A/da not_active Application Discontinuation
- 1977-12-19 FR FR7738319A patent/FR2374319A1/fr active Granted
- 1977-12-20 BE BE183631A patent/BE862066A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES465093A1 (es) | 1978-12-01 |
| FR2374319A1 (fr) | 1978-07-13 |
| IL53386A0 (en) | 1978-01-31 |
| FR2374319B1 (enrdf_load_stackoverflow) | 1980-10-17 |
| ZA776821B (en) | 1978-09-27 |
| DE2755750A1 (de) | 1978-06-22 |
| AU3086777A (en) | 1979-05-31 |
| SE7714210L (sv) | 1978-06-21 |
| AU512654B2 (en) | 1980-10-23 |
| DK564977A (da) | 1978-06-21 |
| SE436878B (sv) | 1985-01-28 |
| JPS5377055A (en) | 1978-07-08 |
| NZ185688A (en) | 1980-09-12 |
| CA1104574A (en) | 1981-07-07 |
| GB1539636A (en) | 1979-01-31 |
| JPS622565B2 (enrdf_load_stackoverflow) | 1987-01-20 |
| IE45905L (en) | 1978-06-20 |
| BE862066A (fr) | 1978-04-14 |
| NL7713825A (nl) | 1978-06-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |