NO128222B - - Google Patents
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- Publication number
- NO128222B NO128222B NO03370/68A NO337068A NO128222B NO 128222 B NO128222 B NO 128222B NO 03370/68 A NO03370/68 A NO 03370/68A NO 337068 A NO337068 A NO 337068A NO 128222 B NO128222 B NO 128222B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- water
- ether
- found
- calculated
- Prior art date
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- 239000002253 acid Substances 0.000 claims description 40
- -1 amine salts Chemical class 0.000 claims description 18
- 150000007513 acids Chemical class 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 229960003424 phenylacetic acid Drugs 0.000 claims description 4
- 239000003279 phenylacetic acid Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 102
- 229910052799 carbon Inorganic materials 0.000 description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000003208 petroleum Substances 0.000 description 28
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 6
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 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
- 239000007787 solid Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 4
- 230000001754 anti-pyretic effect Effects 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ARHWPKZXBHOEEE-UHFFFAOYSA-N alclofenac Chemical compound OC(=O)CC1=CC=C(OCC=C)C(Cl)=C1 ARHWPKZXBHOEEE-UHFFFAOYSA-N 0.000 description 3
- 229960005142 alclofenac Drugs 0.000 description 3
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 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
- QEJHPAGTOOIBFT-UHFFFAOYSA-N (3-chloro-4-propoxy-phenyl)-acetic acid Chemical compound CCCOC1=CC=C(CC(O)=O)C=C1Cl QEJHPAGTOOIBFT-UHFFFAOYSA-N 0.000 description 2
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 description 2
- IDIYIZMETAUIPJ-UHFFFAOYSA-N 2-(3-chloro-4-propan-2-yloxyphenyl)acetic acid Chemical compound CC(C)OC1=CC=C(CC(O)=O)C=C1Cl IDIYIZMETAUIPJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OFNAIAFXWJNHHF-UHFFFAOYSA-N 2-(4-but-2-enoxy-3-chlorophenyl)acetic acid Chemical compound ClC=1C=C(C=CC1OCC=CC)CC(=O)O OFNAIAFXWJNHHF-UHFFFAOYSA-N 0.000 description 2
- 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 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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical class OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 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
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 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 2
- 239000012043 crude product Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 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
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- GRTKFTAOURJJOZ-UHFFFAOYSA-N 2-(3,5-dimethyl-4-prop-2-ynoxyphenyl)acetic acid Chemical compound CC=1C=C(C=C(C1OCC#C)C)CC(=O)O GRTKFTAOURJJOZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LCFFDZNYXPHISM-UHFFFAOYSA-N 2-(3-fluoro-4-propoxyphenyl)acetic acid Chemical compound FC=1C=C(C=CC=1OCCC)CC(=O)O LCFFDZNYXPHISM-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
- 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
- GYBWDAKGSPTODN-UHFFFAOYSA-N 2-(4-methoxy-3-methylphenyl)acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1C GYBWDAKGSPTODN-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
- 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
- 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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 206010000269 abscess Diseases 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 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
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal 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
- ACBFEXJHCINJDS-UHFFFAOYSA-N methyl 2-(3-chloro-4-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C(Cl)=C1 ACBFEXJHCINJDS-UHFFFAOYSA-N 0.000 description 1
- BDHWZAVFXYMECL-UHFFFAOYSA-N methyl 2-(3-chloro-4-hydroxyphenyl)propanoate Chemical compound COC(=O)C(C)C1=CC=C(O)C(Cl)=C1 BDHWZAVFXYMECL-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
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940049953 phenylacetate 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 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 description 1
- 239000013585 weight reducing agent Substances 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE48911 | 1967-09-27 | ||
| BE61764 | 1968-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128222B true NO128222B (xx) | 1973-10-15 |
Family
ID=25647344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO03370/68A NO128222B (xx) | 1967-09-27 | 1968-08-29 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3824277A (xx) |
| AT (1) | AT284092B (xx) |
| CA (1) | CA965436B (xx) |
| CH (1) | CH486412A (xx) |
| DE (1) | DE1793264B2 (xx) |
| DK (1) | DK120159B (xx) |
| ES (1) | ES357584A1 (xx) |
| FR (2) | FR1577840A (xx) |
| GB (1) | GB1174535A (xx) |
| IE (1) | IE32439B1 (xx) |
| NL (1) | NL139457B (xx) |
| NO (1) | NO128222B (xx) |
| OA (1) | OA04038A (xx) |
| SE (1) | SE355567B (xx) |
| SU (1) | SU473354A3 (xx) |
| YU (1) | YU34110B (xx) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT338252B (de) * | 1974-01-14 | 1977-08-10 | Isf Spa | Verfahren zur herstellung der neuen 4-cyclopropylmethoxy-3-chlorphenylessigsaure sowie ihrer salze |
| ES447989A1 (es) * | 1976-05-10 | 1977-06-16 | Ferrer Int | Procedimiento de obtencion de un nuevo compuesto fenoxilado. |
| US4178460A (en) * | 1976-10-01 | 1979-12-11 | American Cyanamid Co. | 2-Haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)-phenylalkanoic acids |
| US4189499A (en) * | 1977-03-16 | 1980-02-19 | Biochefarm S.A. | Lysine 4-allyloxy-3-chlorophenylacetate and method of its preparation |
| GB2015102B (en) * | 1978-02-25 | 1982-09-22 | Girling Ltd | Fluid-pressure operated servo-motor assemblies |
| JP3051145B2 (ja) * | 1990-08-28 | 2000-06-12 | 住友製薬株式会社 | 新規なポリエチレングリコール誘導体修飾ペプチド |
| CN104341307B (zh) * | 2013-08-05 | 2016-12-28 | 北京京朋汇药业研究发展有限公司 | 苯乙酸衍生物及其抗肿瘤用途 |
-
1968
- 1968-08-16 IE IE1005/68A patent/IE32439B1/xx unknown
- 1968-08-23 DE DE19681793264 patent/DE1793264B2/de active Granted
- 1968-08-24 OA OA53358A patent/OA04038A/xx unknown
- 1968-08-26 ES ES357584A patent/ES357584A1/es not_active Expired
- 1968-08-28 GB GB41128/68A patent/GB1174535A/en not_active Expired
- 1968-08-28 AT AT837068A patent/AT284092B/de not_active IP Right Cessation
- 1968-08-29 NL NL686812301A patent/NL139457B/xx not_active IP Right Cessation
- 1968-08-29 DK DK415368AA patent/DK120159B/da not_active IP Right Cessation
- 1968-08-29 FR FR1577840D patent/FR1577840A/fr not_active Expired
- 1968-08-29 SE SE11623/68A patent/SE355567B/xx unknown
- 1968-08-29 YU YU2030/68A patent/YU34110B/xx unknown
- 1968-08-29 FR FR164435A patent/FR8161M/fr not_active Expired
- 1968-08-29 NO NO03370/68A patent/NO128222B/no unknown
- 1968-09-26 CH CH1439468A patent/CH486412A/fr not_active IP Right Cessation
- 1968-09-26 SU SU1275363A patent/SU473354A3/ru active
-
1970
- 1970-05-26 US US00040544A patent/US3824277A/en not_active Expired - Lifetime
-
1973
- 1973-12-28 CA CA189,095A patent/CA965436B/xx not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1793264C3 (xx) | 1973-10-04 |
| CH486412A (fr) | 1970-02-28 |
| NL139457B (nl) | 1973-08-15 |
| GB1174535A (en) | 1969-12-17 |
| YU203068A (en) | 1978-06-30 |
| NL6812301A (xx) | 1969-03-31 |
| SU473354A3 (ru) | 1975-06-05 |
| FR1577840A (xx) | 1969-08-08 |
| SE355567B (xx) | 1973-04-30 |
| US3824277A (en) | 1974-07-16 |
| OA04038A (fr) | 1979-09-30 |
| YU34110B (en) | 1978-12-31 |
| CA965436B (en) | 1975-04-01 |
| IE32439L (en) | 1969-03-27 |
| DE1793264B2 (de) | 1973-03-08 |
| IE32439B1 (en) | 1973-08-08 |
| DE1793264A1 (de) | 1972-03-16 |
| AT284092B (de) | 1970-08-25 |
| DK120159B (da) | 1971-04-19 |
| ES357584A1 (es) | 1970-03-16 |
| FR8161M (xx) | 1970-08-24 |
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