BE718930A - - Google Patents
Info
- Publication number
- BE718930A BE718930A BE718930DA BE718930A BE 718930 A BE718930 A BE 718930A BE 718930D A BE718930D A BE 718930DA BE 718930 A BE718930 A BE 718930A
- Authority
- BE
- Belgium
- Prior art keywords
- acid
- sep
- acids
- water
- alkynyloxy
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 73
- -1 alkaline earth metal salts Chemical class 0.000 claims description 22
- 150000002148 esters Chemical group 0.000 claims description 22
- 150000007513 acids Chemical class 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000002825 nitriles Chemical group 0.000 claims description 4
- 230000000202 analgesic effect Effects 0.000 claims description 3
- 230000002921 anti-spasmodic effect Effects 0.000 claims description 3
- 239000002221 antipyretic Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 239000000730 antalgic agent Substances 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 229940125716 antipyretic agent Drugs 0.000 claims description 2
- 229940124575 antispasmodic agent Drugs 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 229960003424 phenylacetic acid Drugs 0.000 claims description 2
- 239000003279 phenylacetic acid Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 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 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 239000003208 petroleum Substances 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 6
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 6
- 235000019260 propionic acid Nutrition 0.000 description 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 5
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 3
- OPHQAMYQOAWJMB-UHFFFAOYSA-N 2-(3-fluoro-4-prop-2-ynoxyphenyl)acetic acid Chemical compound FC=1C=C(C=CC1OCC#C)CC(=O)O OPHQAMYQOAWJMB-UHFFFAOYSA-N 0.000 description 2
- SRTOIOQWTYYNHA-UHFFFAOYSA-N 2-(3-methoxy-4-prop-2-ynoxyphenyl)acetic acid Chemical compound COC=1C=C(C=CC1OCC#C)CC(=O)O SRTOIOQWTYYNHA-UHFFFAOYSA-N 0.000 description 2
- FCENRTYJKHQXDA-UHFFFAOYSA-N 2-(4-but-2-enoxy-3-methylphenyl)acetic acid Chemical compound CC=1C=C(C=CC1OCC=CC)CC(=O)O FCENRTYJKHQXDA-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 2
- 229960004126 codeine Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- RJFNIPYOSIFCPK-UHFFFAOYSA-N methyl 2-(4-but-2-enoxy-3-chlorophenyl)acetate Chemical compound ClC=1C=C(C=CC1OCC=CC)CC(=O)OC RJFNIPYOSIFCPK-UHFFFAOYSA-N 0.000 description 2
- UBFCYPQWMPUWJN-UHFFFAOYSA-N methyl 2-(4-hydroxy-3-methylphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C(C)=C1 UBFCYPQWMPUWJN-UHFFFAOYSA-N 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- MFLIPOHXYUHIEX-UHFFFAOYSA-N (3-chloro-4-hydroxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC=C(O)C(Cl)=C1 MFLIPOHXYUHIEX-UHFFFAOYSA-N 0.000 description 1
- OTPJLWRFALCRKE-UHFFFAOYSA-N 2-(3-bromo-4-butoxyphenyl)acetic acid Chemical compound BrC=1C=C(C=CC1OCCCC)CC(=O)O OTPJLWRFALCRKE-UHFFFAOYSA-N 0.000 description 1
- NDZOXVZZEHNMBM-UHFFFAOYSA-N 2-(3-bromo-5-methyl-4-prop-2-ynoxyphenyl)acetic acid Chemical compound BrC=1C=C(C=C(C1OCC#C)C)CC(=O)O NDZOXVZZEHNMBM-UHFFFAOYSA-N 0.000 description 1
- KUSQTFMNHGRCGS-UHFFFAOYSA-N 2-(3-chloro-4-hydroxy-5-methoxyphenyl)acetic acid Chemical compound COC1=CC(CC(O)=O)=CC(Cl)=C1O KUSQTFMNHGRCGS-UHFFFAOYSA-N 0.000 description 1
- IXOZYKLWAXYIQY-UHFFFAOYSA-N 2-(3-chloro-5-methyl-4-propoxyphenyl)acetic acid Chemical compound ClC=1C=C(C=C(C=1OCCC)C)CC(=O)O IXOZYKLWAXYIQY-UHFFFAOYSA-N 0.000 description 1
- BMUQWAMTNOZCTI-UHFFFAOYSA-N 2-(3-ethoxy-4-prop-2-ynoxyphenyl)acetic acid Chemical compound C(C)OC=1C=C(C=CC1OCC#C)CC(=O)O BMUQWAMTNOZCTI-UHFFFAOYSA-N 0.000 description 1
- BQZLSVNHKXYJFC-UHFFFAOYSA-N 2-(3-ethoxy-4-propoxyphenyl)acetic acid Chemical compound CCCOC1=CC=C(CC(O)=O)C=C1OCC BQZLSVNHKXYJFC-UHFFFAOYSA-N 0.000 description 1
- ZDXXAKPNPDJSPW-UHFFFAOYSA-N 2-(3-ethyl-4-prop-2-ynoxyphenyl)acetic acid Chemical compound C(C)C=1C=C(C=CC1OCC#C)CC(=O)O ZDXXAKPNPDJSPW-UHFFFAOYSA-N 0.000 description 1
- YEAUYVGUXSZCFI-UHFFFAOYSA-N 2-(3-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(F)=C1 YEAUYVGUXSZCFI-UHFFFAOYSA-N 0.000 description 1
- SGQLGSKBIIHNBL-UHFFFAOYSA-N 2-(3-methoxy-4-propoxyphenyl)acetic acid Chemical compound CCCOC1=CC=C(CC(O)=O)C=C1OC SGQLGSKBIIHNBL-UHFFFAOYSA-N 0.000 description 1
- HEOFMMMLMMHHMC-UHFFFAOYSA-N 2-(3-methyl-4-prop-2-ynoxyphenyl)acetic acid Chemical compound CC=1C=C(C=CC1OCC#C)CC(=O)O HEOFMMMLMMHHMC-UHFFFAOYSA-N 0.000 description 1
- QWFIWIRMLLQNTR-UHFFFAOYSA-N 2-(3-methyl-4-propoxyphenyl)acetic acid Chemical compound CCCOC1=CC=C(CC(O)=O)C=C1C QWFIWIRMLLQNTR-UHFFFAOYSA-N 0.000 description 1
- NPNVIYWKTFQYTK-UHFFFAOYSA-N 2-(4-but-2-enoxy-3-fluorophenyl)acetic acid Chemical compound C(C=CC)OC1=C(C=C(C=C1)CC(=O)O)F NPNVIYWKTFQYTK-UHFFFAOYSA-N 0.000 description 1
- MZLNABBWFZTCQC-UHFFFAOYSA-N 2-(4-but-2-enoxy-3-methylphenyl)acetonitrile Chemical compound C(C=CC)OC1=C(C=C(C=C1)CC#N)C MZLNABBWFZTCQC-UHFFFAOYSA-N 0.000 description 1
- LXZKVRZDXPACMC-UHFFFAOYSA-N 2-(4-butoxy-3-chlorophenyl)acetic acid Chemical compound CCCCOC1=CC=C(CC(O)=O)C=C1Cl LXZKVRZDXPACMC-UHFFFAOYSA-N 0.000 description 1
- ITYJZZRDOPPGLD-UHFFFAOYSA-N 2-(4-butoxy-3-fluorophenyl)acetic acid Chemical compound C(CCC)OC1=C(C=C(C=C1)CC(=O)O)F ITYJZZRDOPPGLD-UHFFFAOYSA-N 0.000 description 1
- UBKXYZQLVZQFHT-UHFFFAOYSA-N 2-(4-butoxy-3-propan-2-ylphenyl)acetic acid Chemical compound C(CCC)OC1=C(C=C(C=C1)CC(=O)O)C(C)C UBKXYZQLVZQFHT-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FNQLIALENPPSNF-UHFFFAOYSA-N C#CCOC(C(Cl)=CC(CC(O)=O)=C1)=C1Cl Chemical compound C#CCOC(C(Cl)=CC(CC(O)=O)=C1)=C1Cl FNQLIALENPPSNF-UHFFFAOYSA-N 0.000 description 1
- MHMHCDFFQUCWKZ-UHFFFAOYSA-N C(C=CC)OC1=C(C=C(C=C1C)CC(=O)O)C Chemical compound C(C=CC)OC1=C(C=C(C=C1C)CC(=O)O)C MHMHCDFFQUCWKZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000000114 Pain Threshold Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 206010000269 abscess Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- ARHWPKZXBHOEEE-UHFFFAOYSA-N alclofenac Chemical compound OC(=O)CC1=CC=C(OCC=C)C(Cl)=C1 ARHWPKZXBHOEEE-UHFFFAOYSA-N 0.000 description 1
- 229960005142 alclofenac Drugs 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
- 229960004193 dextropropoxyphene Drugs 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- FOQCNUUYQWIJPZ-UHFFFAOYSA-N ethyl 2-(3-chloro-4-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C(Cl)=C1 FOQCNUUYQWIJPZ-UHFFFAOYSA-N 0.000 description 1
- 229940073505 ethyl vanillin Drugs 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- KNGPFDQTMHMXDW-UHFFFAOYSA-N methyl 2-(3,5-dichloro-4-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC(Cl)=C(O)C(Cl)=C1 KNGPFDQTMHMXDW-UHFFFAOYSA-N 0.000 description 1
- NJBLWVGKHUOHDG-UHFFFAOYSA-N methyl 2-(3-bromo-4-hydroxy-5-methylphenyl)acetate Chemical compound COC(=O)CC1=CC(C)=C(O)C(Br)=C1 NJBLWVGKHUOHDG-UHFFFAOYSA-N 0.000 description 1
- IPJKZFGPBHAHHW-UHFFFAOYSA-N methyl 2-(3-ethyl-4-hydroxyphenyl)acetate Chemical compound C(C)C=1C=C(C=CC1O)CC(=O)OC IPJKZFGPBHAHHW-UHFFFAOYSA-N 0.000 description 1
- AXONPFSLAZILIE-UHFFFAOYSA-N methyl 2-(3-fluoro-4-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C(F)=C1 AXONPFSLAZILIE-UHFFFAOYSA-N 0.000 description 1
- UCJBJPOAPYTDOA-UHFFFAOYSA-N methyl 2-(4-hydroxy-3,5-dimethylphenyl)acetate Chemical compound COC(=O)CC1=CC(C)=C(O)C(C)=C1 UCJBJPOAPYTDOA-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 229940072358 xylocaine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
- C07D489/04—Salts; Organic complexes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE61764 | 1968-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE718930A true BE718930A (en)) | 1969-02-03 |
Family
ID=3841086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE718930D BE718930A (en)) | 1968-08-01 | 1968-08-01 |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE718930A (en)) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2365555A1 (de) * | 1972-07-11 | 1975-07-10 | Sumitomo Chemical Co | Substituierte essigsaeuren und verfahren zu ihrer herstellung |
| DE2335347C3 (de) | 1972-07-11 | 1977-04-07 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | Substituierte Essigsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Pestizide |
-
1968
- 1968-08-01 BE BE718930D patent/BE718930A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2365555A1 (de) * | 1972-07-11 | 1975-07-10 | Sumitomo Chemical Co | Substituierte essigsaeuren und verfahren zu ihrer herstellung |
| DE2335347C3 (de) | 1972-07-11 | 1977-04-07 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | Substituierte Essigsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Pestizide |
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