DE2626018A1 - Alkinole und verfahren zu ihrer herstellung - Google Patents
Alkinole und verfahren zu ihrer herstellungInfo
- Publication number
- DE2626018A1 DE2626018A1 DE19762626018 DE2626018A DE2626018A1 DE 2626018 A1 DE2626018 A1 DE 2626018A1 DE 19762626018 DE19762626018 DE 19762626018 DE 2626018 A DE2626018 A DE 2626018A DE 2626018 A1 DE2626018 A1 DE 2626018A1
- Authority
- DE
- Germany
- Prior art keywords
- biphenylyl
- alkyl
- formula
- pentyn
- chloro
- Prior art date
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- -1 biphenylyl Chemical group 0.000 claims description 83
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- DBAMUTGXJAWDEA-UHFFFAOYSA-N Butynol Chemical compound CCC#CO DBAMUTGXJAWDEA-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- PKLBWWOBNVIGHG-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenyl]-6-(oxan-2-yloxy)hex-3-yn-2-ol Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1C(O)(C)C#CCCOC1CCCCO1 PKLBWWOBNVIGHG-UHFFFAOYSA-N 0.000 claims description 2
- ZCFWYVSGEYZAAR-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenyl]oct-3-yn-2-ol Chemical compound C1=CC(C(C)(O)C#CCCCC)=CC=C1OC1=CC=C(Cl)C=C1 ZCFWYVSGEYZAAR-UHFFFAOYSA-N 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 2
- YBLVYZVUUYEIJN-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)phenyl]oct-3-yn-2-ol Chemical compound C1=CC(C(C)(O)C#CCCCC)=CC=C1C1=CC=C(Cl)C=C1 YBLVYZVUUYEIJN-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 20
- 150000003254 radicals Chemical class 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000011065 in-situ storage Methods 0.000 description 7
- 150000001247 metal acetylides Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 150000001340 alkali metals Chemical class 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- GKPOMITUDGXOSB-UHFFFAOYSA-N but-3-yn-2-ol Chemical compound CC(O)C#C GKPOMITUDGXOSB-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 150000001728 carbonyl compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 235000019645 odor Nutrition 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000003797 solvolysis reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 125000004423 acyloxy group Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000000475 acetylene derivatives Chemical class 0.000 description 2
- 150000000476 acetylides Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- MJBPUQUGJNAPAZ-AWEZNQCLSA-N butin Chemical compound C1([C@@H]2CC(=O)C3=CC=C(C=C3O2)O)=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-AWEZNQCLSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- LTFTWJYRQNTCHI-UHFFFAOYSA-N hex-1-yn-3-ol Chemical compound CCCC(O)C#C LTFTWJYRQNTCHI-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RXOUXIOIRBYIAZ-UHFFFAOYSA-N 1-[4-(2-chlorophenoxy)phenyl]-3-methylpent-1-yn-3-ol Chemical compound C1=CC(C#CC(C)(O)CC)=CC=C1OC1=CC=CC=C1Cl RXOUXIOIRBYIAZ-UHFFFAOYSA-N 0.000 description 1
- QPUGATPNTOEXMQ-UHFFFAOYSA-N 1-[4-(2-chlorophenyl)phenyl]-4-methylpent-1-yn-3-ol Chemical compound C1=CC(C#CC(O)C(C)C)=CC=C1C1=CC=CC=C1Cl QPUGATPNTOEXMQ-UHFFFAOYSA-N 0.000 description 1
- AWCBVUVVOGXTOT-UHFFFAOYSA-N 1-[4-(3-chlorophenyl)phenyl]pent-1-yn-3-ol Chemical compound C1=CC(C#CC(O)CC)=CC=C1C1=CC=CC(Cl)=C1 AWCBVUVVOGXTOT-UHFFFAOYSA-N 0.000 description 1
- UURRYRSSBWAQHM-UHFFFAOYSA-N 1-[4-(4-chlorophenoxy)phenyl]pent-1-yn-3-ol Chemical compound C1=CC(C#CC(O)CC)=CC=C1OC1=CC=C(Cl)C=C1 UURRYRSSBWAQHM-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical group CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- RUYZJEIKQYLEGZ-UHFFFAOYSA-N 1-fluoro-4-phenylbenzene Chemical group C1=CC(F)=CC=C1C1=CC=CC=C1 RUYZJEIKQYLEGZ-UHFFFAOYSA-N 0.000 description 1
- QPBYBLZYMNWGMO-UHFFFAOYSA-N 2,2,3-trimethyloxirane Chemical compound CC1OC1(C)C QPBYBLZYMNWGMO-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- NARZHDFUDNYHFV-UHFFFAOYSA-N 2-[4-(2-chlorophenoxy)phenyl]-6-(oxan-2-yloxy)hex-3-yn-2-ol Chemical compound C=1C=C(OC=2C(=CC=CC=2)Cl)C=CC=1C(O)(C)C#CCCOC1CCCCO1 NARZHDFUDNYHFV-UHFFFAOYSA-N 0.000 description 1
- YFFKSVCNUKGSSU-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenyl]-8-(oxan-2-yloxy)oct-3-yn-2-ol Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1C(O)(C)C#CCCCCOC1CCCCO1 YFFKSVCNUKGSSU-UHFFFAOYSA-N 0.000 description 1
- DJNNTGDINYBHMO-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenyl]hex-3-yn-2-ol Chemical compound C1=CC(C(C)(O)C#CCC)=CC=C1OC1=CC=C(Cl)C=C1 DJNNTGDINYBHMO-UHFFFAOYSA-N 0.000 description 1
- SQCHDLVYDWIBMB-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)phenyl]oct-3-yn-2-ol Chemical compound C1=CC(C(C)(O)C#CCCCC)=CC=C1C1=CC=C(F)C=C1 SQCHDLVYDWIBMB-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ODOQQMMVLQTKIZ-UHFFFAOYSA-N 3-[4-(2-chlorophenoxy)phenyl]prop-2-yn-1-ol Chemical compound C1=CC(C#CCO)=CC=C1OC1=CC=CC=C1Cl ODOQQMMVLQTKIZ-UHFFFAOYSA-N 0.000 description 1
- MXIWLTSFHUAECA-UHFFFAOYSA-N 3-[4-(3-chlorophenyl)phenyl]prop-2-yn-1-ol Chemical compound C1=CC(C#CCO)=CC=C1C1=CC=CC(Cl)=C1 MXIWLTSFHUAECA-UHFFFAOYSA-N 0.000 description 1
- LTMBOLFAAHIRLX-UHFFFAOYSA-N 3-[4-(4-bromophenoxy)phenyl]prop-2-yn-1-ol Chemical compound C1=CC(C#CCO)=CC=C1OC1=CC=C(Br)C=C1 LTMBOLFAAHIRLX-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 1
- XDOPNIVXURPUJZ-UHFFFAOYSA-N 3-methylpent-4-yn-2-ol Chemical compound CC(O)C(C)C#C XDOPNIVXURPUJZ-UHFFFAOYSA-N 0.000 description 1
- IBANJNLNXZIOFR-UHFFFAOYSA-N 4-[4-(2-bromophenoxy)phenyl]-2-methylbut-3-yn-2-ol Chemical compound C1=CC(C#CC(C)(O)C)=CC=C1OC1=CC=CC=C1Br IBANJNLNXZIOFR-UHFFFAOYSA-N 0.000 description 1
- RHCMKKMSNCQHRN-UHFFFAOYSA-N 4-[4-(3-chlorophenyl)phenyl]-2-methylbut-3-yn-2-ol Chemical compound C1=CC(C#CC(C)(O)C)=CC=C1C1=CC=CC(Cl)=C1 RHCMKKMSNCQHRN-UHFFFAOYSA-N 0.000 description 1
- BGFBBLYZKUSDSF-UHFFFAOYSA-N 4-[4-(3-chlorophenyl)phenyl]but-3-yn-2-ol Chemical compound C1=CC(C#CC(O)C)=CC=C1C1=CC=CC(Cl)=C1 BGFBBLYZKUSDSF-UHFFFAOYSA-N 0.000 description 1
- GKAJHUKWBFNPSN-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)phenyl]-2-methylbut-3-yn-2-ol Chemical compound C1=CC(C#CC(C)(O)C)=CC=C1C1=CC=C(F)C=C1 GKAJHUKWBFNPSN-UHFFFAOYSA-N 0.000 description 1
- URWFOWRQOXUULT-UHFFFAOYSA-N 5-[4-(2-fluorophenoxy)phenyl]hex-3-yne-1,5-diol Chemical compound C1=CC(C(O)(C#CCCO)C)=CC=C1OC1=CC=CC=C1F URWFOWRQOXUULT-UHFFFAOYSA-N 0.000 description 1
- FEBFWFOLGZXVBN-UHFFFAOYSA-N 5-[4-(4-bromophenoxy)phenyl]-2,3-dimethylpent-4-yn-2-ol Chemical compound C1=CC(C#CC(C)C(C)(C)O)=CC=C1OC1=CC=C(Br)C=C1 FEBFWFOLGZXVBN-UHFFFAOYSA-N 0.000 description 1
- MKCYFYZKQAZSQN-UHFFFAOYSA-N 5-[4-(4-bromophenoxy)phenyl]hex-3-yne-1,5-diol Chemical compound C1=CC(C(O)(C#CCCO)C)=CC=C1OC1=CC=C(Br)C=C1 MKCYFYZKQAZSQN-UHFFFAOYSA-N 0.000 description 1
- DDQSIKVVYUZWHL-UHFFFAOYSA-N 5-[4-(4-chlorophenoxy)phenyl]-2,3-dimethylpent-4-yn-2-ol Chemical compound C1=CC(C#CC(C)C(C)(C)O)=CC=C1OC1=CC=C(Cl)C=C1 DDQSIKVVYUZWHL-UHFFFAOYSA-N 0.000 description 1
- KWOAHRVSNUOFRM-UHFFFAOYSA-N 5-[4-(4-chlorophenoxy)phenyl]hex-3-yne-1,5-diol Chemical compound C1=CC(C(O)(C#CCCO)C)=CC=C1OC1=CC=C(Cl)C=C1 KWOAHRVSNUOFRM-UHFFFAOYSA-N 0.000 description 1
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- ZZEWIGYZYLOSHX-UHFFFAOYSA-N 5-[4-(4-fluorophenoxy)phenyl]-2,3-dimethylpent-4-yn-2-ol Chemical compound C1=CC(C#CC(C)C(C)(C)O)=CC=C1OC1=CC=C(F)C=C1 ZZEWIGYZYLOSHX-UHFFFAOYSA-N 0.000 description 1
- OEZKDNHFDMVGKX-UHFFFAOYSA-N 7-[4-(4-chlorophenoxy)phenyl]oct-5-yne-1,7-diol Chemical compound C1=CC(C(O)(C#CCCCCO)C)=CC=C1OC1=CC=C(Cl)C=C1 OEZKDNHFDMVGKX-UHFFFAOYSA-N 0.000 description 1
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- 241000416162 Astragalus gummifer Species 0.000 description 1
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- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
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- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
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- 125000003710 aryl alkyl group Chemical group 0.000 description 1
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- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
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- 230000037213 diet Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- LYXYBSYXGARUEA-UHFFFAOYSA-N hept-1-yn-4-ol Chemical compound CCCC(O)CC#C LYXYBSYXGARUEA-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
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- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- DFGLEWKNMRPOGC-UHFFFAOYSA-N lithium;2-[4-(4-fluorophenyl)phenyl]oct-3-yn-2-olate Chemical compound [Li+].C1=CC(C(C)([O-])C#CCCCC)=CC=C1C1=CC=C(F)C=C1 DFGLEWKNMRPOGC-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical class [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
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- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
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- 230000003204 osmotic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- LBSKEFWQPNVWTP-UHFFFAOYSA-N pent-1-yn-3-ol Chemical compound CCC(O)C#C LBSKEFWQPNVWTP-UHFFFAOYSA-N 0.000 description 1
- JTHLRRZARWSHBE-UHFFFAOYSA-N pent-4-yn-2-ol Chemical compound CC(O)CC#C JTHLRRZARWSHBE-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- FWLKYEAOOIPJRL-UHFFFAOYSA-N prop-1-yn-1-ol Chemical compound CC#CO FWLKYEAOOIPJRL-UHFFFAOYSA-N 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Obesity (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (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)
- Pyrane Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762626018 DE2626018A1 (de) | 1976-06-10 | 1976-06-10 | Alkinole und verfahren zu ihrer herstellung |
| AU25499/77A AU510322B2 (en) | 1976-06-10 | 1977-05-25 | Alkynols |
| GB23432/77A GB1538417A (en) | 1976-06-10 | 1977-06-02 | Alkynols |
| IL52274A IL52274A (en) | 1976-06-10 | 1977-06-07 | 4 halophenyl(or halophenoxy)phenyl alkyonols and preparatiion thereof and pharmaceutical compositions containing them |
| FR7717519A FR2354309A1 (fr) | 1976-06-10 | 1977-06-08 | Nouveaux alcynols, leur procede de preparation et leurs applications en tant que medicaments |
| IT49756/77A IT1078469B (it) | 1976-06-10 | 1977-06-08 | Procedimento per la produzione di alchinoli |
| AT406877A AT360971B (de) | 1976-06-10 | 1977-06-08 | Verfahren zur herstellung neuer alkinole |
| JP6876777A JPS52151138A (en) | 1976-06-10 | 1977-06-09 | Alkynols and process for producing the same |
| CA280,164A CA1084516A (en) | 1976-06-10 | 1977-06-09 | Alkynols and process for their preparation |
| ZA00773484A ZA773484B (en) | 1976-06-10 | 1977-06-09 | Alkynols and preparation thereof |
| US05/805,045 US4151294A (en) | 1976-06-10 | 1977-06-09 | Alkynols and process for their preparation |
| SE7706724A SE7706724L (sv) | 1976-06-10 | 1977-06-09 | Alkinoler och forfarande for framstellning derav |
| ES459654A ES459654A1 (es) | 1976-06-10 | 1977-06-10 | Procedimiento para la obtencion de alquinoles. |
| NL7706401A NL7706401A (nl) | 1976-06-10 | 1977-06-10 | Alkynolen en werkwijzen om deze te bereiden. |
| BE178348A BE855575A (nl) | 1976-06-10 | 1977-06-10 | Alkynolen en werkwijzen om deze te bereiden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762626018 DE2626018A1 (de) | 1976-06-10 | 1976-06-10 | Alkinole und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2626018A1 true DE2626018A1 (de) | 1977-12-22 |
Family
ID=5980233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762626018 Withdrawn DE2626018A1 (de) | 1976-06-10 | 1976-06-10 | Alkinole und verfahren zu ihrer herstellung |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4151294A (enExample) |
| JP (1) | JPS52151138A (enExample) |
| AT (1) | AT360971B (enExample) |
| AU (1) | AU510322B2 (enExample) |
| BE (1) | BE855575A (enExample) |
| CA (1) | CA1084516A (enExample) |
| DE (1) | DE2626018A1 (enExample) |
| ES (1) | ES459654A1 (enExample) |
| FR (1) | FR2354309A1 (enExample) |
| GB (1) | GB1538417A (enExample) |
| IL (1) | IL52274A (enExample) |
| IT (1) | IT1078469B (enExample) |
| NL (1) | NL7706401A (enExample) |
| SE (1) | SE7706724L (enExample) |
| ZA (1) | ZA773484B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008333A1 (de) * | 1978-06-27 | 1980-03-05 | Ciba-Geigy Ag | Alpha-Prop-1-inyl-3-phenoxybenzylalkohole, ihre Herstellung und Verwendung als Zwischenprodukte zur Herstellung von Schädlingsbekämpfungsmitteln |
| US4528114A (en) * | 1981-12-18 | 1985-07-09 | Hoffmann-La Roche Inc. | Acetylenes |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5155196A (en) * | 1987-06-01 | 1992-10-13 | The Dow Chemical Company | Polymer resulting from the cure of a preformed chromene-containing mixture |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969415A (en) * | 1971-12-01 | 1976-07-13 | Sandoz, Inc. | 1-(2-Naphthyl)-2,3-butadien-1-ols |
| US3929902A (en) * | 1972-01-19 | 1975-12-30 | Sandoz Ag | 1-Phenyl-2, 3-butadien-1-ols |
| US3888933A (en) * | 1973-12-28 | 1975-06-10 | Sandoz Ag | 4-hydroxyethyl-biphenylyl-butadienols |
| US3879449A (en) * | 1974-03-04 | 1975-04-22 | Sandoz Ag | 1-Phenyl-4-hydroxy-1-buten-3-ones and esters thereof |
| US3939278A (en) * | 1974-07-05 | 1976-02-17 | Eli Lilly And Company | Phenoxyphenyl-acetylenes and thio analogues thereof as antithrombotic agents |
| DE2519719A1 (de) * | 1975-05-02 | 1976-11-18 | Merck Patent Gmbh | Phenylalkanole und verfahren zu ihrer herstellung |
| DE2528958A1 (de) * | 1975-06-28 | 1977-01-13 | Merck Patent Gmbh | Araliphatische dihalogenverbindungen und verfahren zu ihrer herstellung |
-
1976
- 1976-06-10 DE DE19762626018 patent/DE2626018A1/de not_active Withdrawn
-
1977
- 1977-05-25 AU AU25499/77A patent/AU510322B2/en not_active Expired
- 1977-06-02 GB GB23432/77A patent/GB1538417A/en not_active Expired
- 1977-06-07 IL IL52274A patent/IL52274A/xx unknown
- 1977-06-08 FR FR7717519A patent/FR2354309A1/fr active Granted
- 1977-06-08 IT IT49756/77A patent/IT1078469B/it active
- 1977-06-08 AT AT406877A patent/AT360971B/de not_active IP Right Cessation
- 1977-06-09 US US05/805,045 patent/US4151294A/en not_active Expired - Lifetime
- 1977-06-09 ZA ZA00773484A patent/ZA773484B/xx unknown
- 1977-06-09 JP JP6876777A patent/JPS52151138A/ja active Pending
- 1977-06-09 CA CA280,164A patent/CA1084516A/en not_active Expired
- 1977-06-09 SE SE7706724A patent/SE7706724L/xx unknown
- 1977-06-10 NL NL7706401A patent/NL7706401A/xx not_active Application Discontinuation
- 1977-06-10 ES ES459654A patent/ES459654A1/es not_active Expired
- 1977-06-10 BE BE178348A patent/BE855575A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008333A1 (de) * | 1978-06-27 | 1980-03-05 | Ciba-Geigy Ag | Alpha-Prop-1-inyl-3-phenoxybenzylalkohole, ihre Herstellung und Verwendung als Zwischenprodukte zur Herstellung von Schädlingsbekämpfungsmitteln |
| US4528114A (en) * | 1981-12-18 | 1985-07-09 | Hoffmann-La Roche Inc. | Acetylenes |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1084516A (en) | 1980-08-26 |
| FR2354309A1 (fr) | 1978-01-06 |
| AT360971B (de) | 1981-02-10 |
| IL52274A0 (en) | 1977-08-31 |
| JPS52151138A (en) | 1977-12-15 |
| US4151294A (en) | 1979-04-24 |
| AU510322B2 (en) | 1980-06-19 |
| ATA406877A (de) | 1980-07-15 |
| IL52274A (en) | 1980-02-29 |
| BE855575A (nl) | 1977-12-12 |
| NL7706401A (nl) | 1977-12-13 |
| AU2549977A (en) | 1978-11-30 |
| FR2354309B1 (enExample) | 1981-01-09 |
| IT1078469B (it) | 1985-05-08 |
| GB1538417A (en) | 1979-01-17 |
| ES459654A1 (es) | 1978-12-01 |
| SE7706724L (sv) | 1977-12-11 |
| ZA773484B (en) | 1978-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |