CA1092147A - Alkyne compounds and process for their preparation - Google Patents
Alkyne compounds and process for their preparationInfo
- Publication number
- CA1092147A CA1092147A CA255,001A CA255001A CA1092147A CA 1092147 A CA1092147 A CA 1092147A CA 255001 A CA255001 A CA 255001A CA 1092147 A CA1092147 A CA 1092147A
- Authority
- CA
- Canada
- Prior art keywords
- yne
- phenyl
- compounds
- hydroxybut
- fluorobiphenylyl
- 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.)
- Expired
Links
- -1 Alkyne compounds Chemical class 0.000 title claims abstract description 61
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000001475 halogen functional group Chemical group 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 12
- 239000002184 metal Substances 0.000 abstract description 12
- 150000003839 salts Chemical class 0.000 abstract description 12
- 230000000694 effects Effects 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 20
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 15
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052744 lithium Inorganic materials 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- 235000019270 ammonium chloride Nutrition 0.000 description 8
- 150000001728 carbonyl compounds Chemical class 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 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 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 150000001342 alkaline earth metals Chemical group 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-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
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 239000003814 drug 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
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- RUYZJEIKQYLEGZ-UHFFFAOYSA-N 1-fluoro-4-phenylbenzene Chemical group C1=CC(F)=CC=C1C1=CC=CC=C1 RUYZJEIKQYLEGZ-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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
- 150000007513 acids Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 150000001247 metal acetylides Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 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
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 238000003747 Grignard reaction Methods 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000000476 acetylides Chemical class 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 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
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- XRGPFNGLRSIPSA-UHFFFAOYSA-N butyn-2-one Chemical group CC(=O)C#C XRGPFNGLRSIPSA-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 description 2
- 229910001641 magnesium iodide Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- SLERPCVQDVNSAK-UHFFFAOYSA-N silver;ethyne Chemical compound [Ag+].[C-]#C SLERPCVQDVNSAK-UHFFFAOYSA-N 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229940001593 sodium carbonate Drugs 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003797 solvolysis reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- SKRCVISDQNTPEQ-UHFFFAOYSA-N 1-(2-phenylphenyl)prop-2-yn-1-ol Chemical compound C#CC(O)C1=CC=CC=C1C1=CC=CC=C1 SKRCVISDQNTPEQ-UHFFFAOYSA-N 0.000 description 1
- GMPGAPATPBXNSX-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-nitrobenzene Chemical group C1=CC([N+](=O)[O-])=CC=C1C1=CC=C(F)C=C1 GMPGAPATPBXNSX-UHFFFAOYSA-N 0.000 description 1
- CHTRECBHXDOVHT-UHFFFAOYSA-N 1-(4-phenoxyphenyl)prop-2-yn-1-ol Chemical compound C1=CC(C(C#C)O)=CC=C1OC1=CC=CC=C1 CHTRECBHXDOVHT-UHFFFAOYSA-N 0.000 description 1
- MFDZKTBSOXWUJR-UHFFFAOYSA-N 1-(4-phenoxyphenyl)prop-2-ynyl acetate Chemical compound C1=CC(C(C#C)OC(=O)C)=CC=C1OC1=CC=CC=C1 MFDZKTBSOXWUJR-UHFFFAOYSA-N 0.000 description 1
- NCYVSMYXAJHDTQ-UHFFFAOYSA-N 1-[4-(2,4-difluorophenoxy)phenyl]-1-phenylprop-2-yn-1-ol Chemical compound C=1C=C(OC=2C(=CC(F)=CC=2)F)C=CC=1C(C#C)(O)C1=CC=CC=C1 NCYVSMYXAJHDTQ-UHFFFAOYSA-N 0.000 description 1
- JRTQLJZRPDMFQF-UHFFFAOYSA-N 1-[4-(2,4-difluorophenoxy)phenyl]prop-2-ynyl acetate Chemical compound C1=CC(C(C#C)OC(=O)C)=CC=C1OC1=CC=C(F)C=C1F JRTQLJZRPDMFQF-UHFFFAOYSA-N 0.000 description 1
- IUYJUWBXTNVNRL-UHFFFAOYSA-N 1-[4-(2-chlorophenoxy)phenyl]prop-2-yn-1-ol Chemical compound C1=CC(C(C#C)O)=CC=C1OC1=CC=CC=C1Cl IUYJUWBXTNVNRL-UHFFFAOYSA-N 0.000 description 1
- GUJUITZNCPVHAZ-UHFFFAOYSA-N 1-[4-(2-fluorophenoxy)phenyl]prop-2-yn-1-ol Chemical compound C1=CC(C(C#C)O)=CC=C1OC1=CC=CC=C1F GUJUITZNCPVHAZ-UHFFFAOYSA-N 0.000 description 1
- FHPVILTUOAHLMC-UHFFFAOYSA-N 1-[4-(4-bromophenoxy)phenyl]-1-phenylprop-2-yn-1-ol Chemical compound C=1C=C(OC=2C=CC(Br)=CC=2)C=CC=1C(C#C)(O)C1=CC=CC=C1 FHPVILTUOAHLMC-UHFFFAOYSA-N 0.000 description 1
- ZLCKVNCXEAADBN-UHFFFAOYSA-N 1-[4-(4-fluorophenoxy)phenyl]prop-2-yn-1-ol Chemical compound C1=CC(C(C#C)O)=CC=C1OC1=CC=C(F)C=C1 ZLCKVNCXEAADBN-UHFFFAOYSA-N 0.000 description 1
- IXKDCGKNNLHMHN-UHFFFAOYSA-N 1-[4-(4-fluorophenoxy)phenyl]prop-2-ynyl acetate Chemical compound C1=CC(C(C#C)OC(=O)C)=CC=C1OC1=CC=C(F)C=C1 IXKDCGKNNLHMHN-UHFFFAOYSA-N 0.000 description 1
- LGJJGWHKUXUJNR-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)phenyl]ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=C(F)C=C1 LGJJGWHKUXUJNR-UHFFFAOYSA-N 0.000 description 1
- NLZZFQFUPLKATG-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)phenyl]propan-1-one Chemical group C1=CC(C(=O)CC)=CC=C1C1=CC=C(F)C=C1 NLZZFQFUPLKATG-UHFFFAOYSA-N 0.000 description 1
- PGPNJCAMHOJTEF-UHFFFAOYSA-N 1-chloro-4-phenoxybenzene Chemical compound C1=CC(Cl)=CC=C1OC1=CC=CC=C1 PGPNJCAMHOJTEF-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- HAYAZOLCFXUCGS-UHFFFAOYSA-N 1-fluoro-4-(4-iodophenyl)benzene Chemical group C1=CC(F)=CC=C1C1=CC=C(I)C=C1 HAYAZOLCFXUCGS-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- QCMCRCPECQCQGP-UHFFFAOYSA-N 2-(4-phenoxyphenyl)but-3-yn-2-yl 2,2-dimethylpropanoate Chemical compound C1=CC(C(C)(C#C)OC(=O)C(C)(C)C)=CC=C1OC1=CC=CC=C1 QCMCRCPECQCQGP-UHFFFAOYSA-N 0.000 description 1
- QYUGQBZIRIALGK-UHFFFAOYSA-N 2-(4-phenoxyphenyl)but-3-yn-2-yl acetate Chemical compound C1=CC(C(C)(C#C)OC(=O)C)=CC=C1OC1=CC=CC=C1 QYUGQBZIRIALGK-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- SAZGHNRMNIJRBB-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenyl]but-3-yn-2-yl acetate Chemical compound C1=CC(C(C)(C#C)OC(=O)C)=CC=C1OC1=CC=C(Cl)C=C1Cl SAZGHNRMNIJRBB-UHFFFAOYSA-N 0.000 description 1
- LGBPUVJBNMQBBB-UHFFFAOYSA-N 2-[4-(2-chlorophenoxy)phenyl]but-3-yn-2-ol Chemical compound C1=CC(C(O)(C#C)C)=CC=C1OC1=CC=CC=C1Cl LGBPUVJBNMQBBB-UHFFFAOYSA-N 0.000 description 1
- UYFGZOKZPKCPQW-UHFFFAOYSA-N 2-[4-(2-fluorophenoxy)phenyl]but-3-yn-2-ol Chemical compound C1=CC(C(O)(C#C)C)=CC=C1OC1=CC=CC=C1F UYFGZOKZPKCPQW-UHFFFAOYSA-N 0.000 description 1
- SBOLVEKDKQKNOY-UHFFFAOYSA-N 2-[4-(3-fluorophenoxy)phenyl]but-3-yn-2-ol Chemical compound C1=CC(C(O)(C#C)C)=CC=C1OC1=CC=CC(F)=C1 SBOLVEKDKQKNOY-UHFFFAOYSA-N 0.000 description 1
- QTBXVLSQYORLDU-UHFFFAOYSA-N 2-[4-(4-bromophenoxy)phenyl]but-3-yn-2-yl acetate Chemical compound C1=CC(C(C)(C#C)OC(=O)C)=CC=C1OC1=CC=C(Br)C=C1 QTBXVLSQYORLDU-UHFFFAOYSA-N 0.000 description 1
- FUQXQGPLKZUXEG-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]but-3-yn-2-ol Chemical compound C1=CC(C(O)(C#C)C)=CC=C1OC1=CC=C(F)C=C1 FUQXQGPLKZUXEG-UHFFFAOYSA-N 0.000 description 1
- WPNNSTXNGTVEEW-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]but-3-yn-2-yl butanoate Chemical compound C1=CC(C(C)(C#C)OC(=O)CCC)=CC=C1OC1=CC=C(F)C=C1 WPNNSTXNGTVEEW-UHFFFAOYSA-N 0.000 description 1
- YCVAEKVJBAYMNC-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]but-3-yn-2-yl formate Chemical compound C1=CC(C(OC=O)(C#C)C)=CC=C1OC1=CC=C(F)C=C1 YCVAEKVJBAYMNC-UHFFFAOYSA-N 0.000 description 1
- BFLSGRJEBWHPNL-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]but-3-yn-2-yl hexanoate Chemical compound C1=CC(C(C)(C#C)OC(=O)CCCCC)=CC=C1OC1=CC=C(F)C=C1 BFLSGRJEBWHPNL-UHFFFAOYSA-N 0.000 description 1
- YHEAKWMNQXKAEO-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]but-3-yn-2-yl propanoate Chemical compound C1=CC(C(C)(C#C)OC(=O)CC)=CC=C1OC1=CC=C(F)C=C1 YHEAKWMNQXKAEO-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- NZPLUKSGSIIPMX-UHFFFAOYSA-N 3-(4-phenoxyphenyl)hex-1-yn-3-ol Chemical compound C1=CC(C(O)(C#C)CCC)=CC=C1OC1=CC=CC=C1 NZPLUKSGSIIPMX-UHFFFAOYSA-N 0.000 description 1
- YFCZOSRWHSRMCF-UHFFFAOYSA-N 3-(4-phenoxyphenyl)hex-1-yn-3-yl acetate Chemical compound C1=CC(C(OC(C)=O)(C#C)CCC)=CC=C1OC1=CC=CC=C1 YFCZOSRWHSRMCF-UHFFFAOYSA-N 0.000 description 1
- ZQCHMLGYSMEHJU-UHFFFAOYSA-N 3-(4-phenoxyphenyl)pent-1-yn-3-yl acetate Chemical compound C1=CC(C(OC(C)=O)(C#C)CC)=CC=C1OC1=CC=CC=C1 ZQCHMLGYSMEHJU-UHFFFAOYSA-N 0.000 description 1
- MEOATMVFLUHVTF-UHFFFAOYSA-N 3-[4-(2-chlorophenoxy)phenyl]hept-1-yn-3-ol Chemical compound C1=CC(C(O)(C#C)CCCC)=CC=C1OC1=CC=CC=C1Cl MEOATMVFLUHVTF-UHFFFAOYSA-N 0.000 description 1
- HPHWLSQJRGVOHF-UHFFFAOYSA-N 3-[4-(2-chlorophenoxy)phenyl]pent-1-yn-3-ol Chemical compound C1=CC(C(O)(C#C)CC)=CC=C1OC1=CC=CC=C1Cl HPHWLSQJRGVOHF-UHFFFAOYSA-N 0.000 description 1
- XQYHJXHZHVUVPM-UHFFFAOYSA-N 3-[4-(2-fluorophenoxy)phenyl]hex-1-yn-3-ol Chemical compound C1=CC(C(O)(C#C)CCC)=CC=C1OC1=CC=CC=C1F XQYHJXHZHVUVPM-UHFFFAOYSA-N 0.000 description 1
- PQJROFZNSCORDN-UHFFFAOYSA-N 3-[4-(4-bromophenoxy)phenyl]hept-1-yn-3-ol Chemical compound C1=CC(C(O)(C#C)CCCC)=CC=C1OC1=CC=C(Br)C=C1 PQJROFZNSCORDN-UHFFFAOYSA-N 0.000 description 1
- IANNTTAALHXFDQ-UHFFFAOYSA-N 3-[4-(4-chlorophenoxy)phenyl]pent-1-yn-3-ol Chemical compound C1=CC(C(O)(C#C)CC)=CC=C1OC1=CC=C(Cl)C=C1 IANNTTAALHXFDQ-UHFFFAOYSA-N 0.000 description 1
- TVLZTZOTDILDOJ-UHFFFAOYSA-N 3-[4-(4-fluorophenoxy)phenyl]hept-1-yn-3-yl 2,2-dimethylpropanoate Chemical compound C1=CC(C(OC(=O)C(C)(C)C)(C#C)CCCC)=CC=C1OC1=CC=C(F)C=C1 TVLZTZOTDILDOJ-UHFFFAOYSA-N 0.000 description 1
- OBUCZUIYYKCYSI-UHFFFAOYSA-N 3-[4-(4-fluorophenoxy)phenyl]hex-1-yn-3-yl 2,2-dimethylpropanoate Chemical compound C1=CC(C(OC(=O)C(C)(C)C)(C#C)CCC)=CC=C1OC1=CC=C(F)C=C1 OBUCZUIYYKCYSI-UHFFFAOYSA-N 0.000 description 1
- PWJFRZMEPDOAER-UHFFFAOYSA-N 3-[4-(4-fluorophenoxy)phenyl]pent-1-yn-3-yl 2,2-dimethylpropanoate Chemical compound C1=CC(C(OC(=O)C(C)(C)C)(C#C)CC)=CC=C1OC1=CC=C(F)C=C1 PWJFRZMEPDOAER-UHFFFAOYSA-N 0.000 description 1
- LIUNUDYRPVZGSK-UHFFFAOYSA-N 3-[4-(4-fluorophenoxy)phenyl]pent-1-yn-3-yl acetate Chemical compound C1=CC(C(OC(C)=O)(C#C)CC)=CC=C1OC1=CC=C(F)C=C1 LIUNUDYRPVZGSK-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 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 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- DBAMUTGXJAWDEA-UHFFFAOYSA-N Butynol Chemical compound CCC#CO DBAMUTGXJAWDEA-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 229910021055 KNH2 Inorganic materials 0.000 description 1
- 229910013698 LiNH2 Inorganic materials 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 229910018954 NaNH2 Inorganic materials 0.000 description 1
- RGPDEAGGEXEMMM-UHFFFAOYSA-N Nefopam Chemical compound C12=CC=CC=C2CN(C)CCOC1C1=CC=CC=C1 RGPDEAGGEXEMMM-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- IINBBTLFYFUBOD-UHFFFAOYSA-N [1-(4-phenoxyphenyl)-1-phenylprop-2-ynyl] acetate Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(C#C)(OC(=O)C)C1=CC=CC=C1 IINBBTLFYFUBOD-UHFFFAOYSA-N 0.000 description 1
- GTIVJAZWOQMRGD-UHFFFAOYSA-N [1-[4-(4-fluorophenoxy)phenyl]-1-phenylprop-2-ynyl] 2,2-dimethylpropanoate Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1C(C#C)(OC(=O)C(C)(C)C)C1=CC=CC=C1 GTIVJAZWOQMRGD-UHFFFAOYSA-N 0.000 description 1
- ARTCPSGFPTVHKL-UHFFFAOYSA-N [1-[4-(4-fluorophenoxy)phenyl]-1-phenylprop-2-ynyl] acetate Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1C(C#C)(OC(=O)C)C1=CC=CC=C1 ARTCPSGFPTVHKL-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 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
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KZXVOMYVNQPCKX-UHFFFAOYSA-N ethyne;mercury(1+) Chemical compound [Hg+].[C-]#C KZXVOMYVNQPCKX-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- LTFTWJYRQNTCHI-UHFFFAOYSA-N hex-1-yn-3-ol Chemical compound CCCC(O)C#C LTFTWJYRQNTCHI-UHFFFAOYSA-N 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 150000002561 ketenes Chemical class 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- OYICOGPBEIHJEO-UHFFFAOYSA-L magnesium;acetylene;dibromide Chemical compound [Mg+2].[Br-].[Br-].C#C OYICOGPBEIHJEO-UHFFFAOYSA-L 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate 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
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 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
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 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
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000002560 therapeutic procedure 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
- 229910052905 tridymite Inorganic materials 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2527352 | 1975-06-19 | ||
| DE19752527352 DE2527352A1 (de) | 1975-06-19 | 1975-06-19 | Alkin-derivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1092147A true CA1092147A (en) | 1980-12-23 |
Family
ID=5949449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA255,001A Expired CA1092147A (en) | 1975-06-19 | 1976-06-16 | Alkyne compounds and process for their preparation |
Country Status (22)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2756031A1 (de) * | 1977-12-15 | 1979-06-28 | Bayer Ag | 1-halogen-1-propin-3-ole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE2964800D1 (en) * | 1978-06-27 | 1983-03-24 | Ciba Geigy Ag | Alpha-prop-1-ynyl-3-phenoxybenzyl alcohols, their preparation and use as intermediate products in the preparation of pesticides |
| US5229426A (en) * | 1988-09-15 | 1993-07-20 | Ciba-Geigy Corporation | Ethers useful for controlling pests |
| ES2054081T3 (es) * | 1988-09-15 | 1994-08-01 | Ciba Geigy Ag | Nuevos eteres. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1307360A (en) * | 1969-05-16 | 1973-02-21 | Bdh Pharmaceuticals Ltd | Substituted 17alpha-penta-1,3-diynyl steroids |
| BE792079A (fr) * | 1971-12-01 | 1973-05-29 | Sandoz Sa | Nouveaux composes insatures, leur preparation et leur application commemedicaments |
| US3879449A (en) * | 1974-03-04 | 1975-04-22 | Sandoz Ag | 1-Phenyl-4-hydroxy-1-buten-3-ones and esters thereof |
-
1975
- 1975-06-19 DE DE19752527352 patent/DE2527352A1/de not_active Withdrawn
-
1976
- 1976-06-15 FR FR7618099A patent/FR2314709A1/fr active Granted
- 1976-06-16 CA CA255,001A patent/CA1092147A/en not_active Expired
- 1976-06-17 LU LU75182A patent/LU75182A1/xx unknown
- 1976-06-17 DK DK272376A patent/DK272376A/da not_active Application Discontinuation
- 1976-06-17 HU HU76ME1991A patent/HU176563B/hu unknown
- 1976-06-17 IL IL49828A patent/IL49828A/xx unknown
- 1976-06-18 JP JP51072700A patent/JPS523028A/ja active Pending
- 1976-06-18 AT AT446276A patent/AT354427B/de not_active IP Right Cessation
- 1976-06-18 GB GB25479/76A patent/GB1498377A/en not_active Expired
- 1976-06-18 NL NL7606646A patent/NL7606646A/xx not_active Application Discontinuation
- 1976-06-18 SE SE7607021A patent/SE7607021L/ not_active Application Discontinuation
- 1976-06-18 IE IE1318/76A patent/IE43121B1/en unknown
- 1976-06-18 CS CS764028A patent/CS199204B2/cs unknown
- 1976-06-18 BE BE168051A patent/BE843104A/xx unknown
- 1976-06-18 ZA ZA763626A patent/ZA763626B/xx unknown
- 1976-06-18 AU AU15029/76A patent/AU499802B2/en not_active Expired
- 1976-06-18 US US05/697,579 patent/US4115456A/en not_active Expired - Lifetime
- 1976-06-18 ES ES448989A patent/ES448989A1/es not_active Expired
-
1979
- 1979-03-12 IT IT7948303A patent/IT7948303A0/it unknown
-
1980
- 1980-05-08 HK HK246/80A patent/HK24680A/xx unknown
-
1981
- 1981-12-30 MY MY57/81A patent/MY8100057A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU75182A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-01-18 |
| HK24680A (en) | 1980-05-16 |
| IL49828A (en) | 1981-06-29 |
| MY8100057A (en) | 1981-12-31 |
| FR2314709A1 (fr) | 1977-01-14 |
| BE843104A (nl) | 1976-12-20 |
| FR2314709B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-09-28 |
| JPS523028A (en) | 1977-01-11 |
| IL49828A0 (en) | 1976-08-31 |
| GB1498377A (en) | 1978-01-18 |
| ATA446276A (de) | 1979-06-15 |
| AU1502976A (en) | 1977-12-22 |
| IE43121L (en) | 1976-12-19 |
| US4115456A (en) | 1978-09-19 |
| AT354427B (de) | 1979-01-10 |
| SE7607021L (sv) | 1976-12-20 |
| ES448989A1 (es) | 1977-07-01 |
| DK272376A (da) | 1976-12-20 |
| IE43121B1 (en) | 1980-12-17 |
| IT7948303A0 (it) | 1979-03-12 |
| AU499802B2 (en) | 1979-05-03 |
| HU176563B (en) | 1981-03-28 |
| CS199204B2 (en) | 1980-07-31 |
| NL7606646A (nl) | 1976-12-21 |
| ZA763626B (en) | 1977-05-25 |
| DE2527352A1 (de) | 1976-12-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Logue et al. | Cuprous trimethylsilylacetylide. Preparation and reaction with acid chlorides | |
| US4073936A (en) | Hypolipidemic allene carboxylic esters | |
| US4052446A (en) | 11,16-substituted prostaglandins | |
| US4081476A (en) | 1-Aryl-1-lower alkyl-1-buten-3-ols and ester derivatives | |
| CA1092147A (en) | Alkyne compounds and process for their preparation | |
| Hauser et al. | Aldol Condensation of Esters with Ketones or Aldehydes to Form β-Hydroxy Esters by Lithium Amide. Comparison with the Reformatsky Reaction1 | |
| CA1123442A (en) | Fluorinated polyenes | |
| US4196215A (en) | Alkyne compounds and method of use | |
| CA1045131A (en) | Derivatives of 9-hydroxy-13-trans-prostenoic acid | |
| US3969415A (en) | 1-(2-Naphthyl)-2,3-butadien-1-ols | |
| US4055597A (en) | 10-Aza-11,12-secoprostaglandins | |
| US3876690A (en) | 1-alkoxy-9-keto-prostenoic acid derivatives | |
| JPS594434B2 (ja) | チアプロスタグランジンユウドウタイオヨビソノセイゾウホウホウ | |
| IL41305A (en) | Method for preparing prosta-glandins of the a,e,f and 11-deoxy-e series and certain novel 15-deoxoprostaglandins | |
| NO136092B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| US4088536A (en) | Method for preparing prostaglandins | |
| JPS606653A (ja) | 抗高コレステロ−ル血症活性を有する５−チアアルカン酸誘導体 | |
| US3932467A (en) | Process for the production of 2β-formyl 3α-protected hydroxy-5-oxocyclopentane-1α-heptanoic acids and esters corresponding | |
| US3847994A (en) | 2,2-dimethyl-5-(aryloxy)-valeraldehydes | |
| EP0101004B1 (en) | Process for preparing 4-oxo-4, 5, 6, 7-tetrahydroindole derivative | |
| US4537906A (en) | Substituted phenylalkenoic acids and esters | |
| US4197407A (en) | Prostenoic acids and esters | |
| US4151294A (en) | Alkynols and process for their preparation | |
| US3102133A (en) | 1-[5-(6-methoxy-2-naphthyl)-2-oxycyclopentyl]-2-propanone derivatives | |
| US3980795A (en) | Pyrazolidinones and a process for their preparation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |