CH619205A5 - - Google Patents
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- Publication number
- CH619205A5 CH619205A5 CH1592575A CH1592575A CH619205A5 CH 619205 A5 CH619205 A5 CH 619205A5 CH 1592575 A CH1592575 A CH 1592575A CH 1592575 A CH1592575 A CH 1592575A CH 619205 A5 CH619205 A5 CH 619205A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- chloro
- general formula
- radical
- carbon atoms
- Prior art date
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- -1 benzyl halide Chemical class 0.000 claims description 9
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- IYTUKSIOQKTZEG-UHFFFAOYSA-N 3-chloro-4-hydroxyphenylacetic acid Natural products OC(=O)CC1=CC=C(O)C(Cl)=C1 IYTUKSIOQKTZEG-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 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 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 150000001414 amino alcohols Chemical class 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 17
- 239000011541 reaction mixture Substances 0.000 description 15
- 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 14
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 7
- DFHBBMJTBBLQSA-UHFFFAOYSA-N 2-(3-chloro-4-phenylmethoxyphenyl)acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1OCC1=CC=CC=C1 DFHBBMJTBBLQSA-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 150000003946 cyclohexylamines Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229920002866 paraformaldehyde Polymers 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- RPNSUIRLAUJMRP-UHFFFAOYSA-N 2-[3-chloro-4-[(3-chloro-4-methoxyphenyl)methoxy]phenyl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC=C1COC1=CC=C(CC(O)=O)C=C1Cl RPNSUIRLAUJMRP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229960003424 phenylacetic acid Drugs 0.000 description 4
- 239000003279 phenylacetic acid Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- IELPPEZSLSKWCP-UHFFFAOYSA-N 1-(chloromethyl)-4-(2-methylpropoxy)benzene Chemical compound CC(C)COC1=CC=C(CCl)C=C1 IELPPEZSLSKWCP-UHFFFAOYSA-N 0.000 description 3
- QGRPVMLBTFGQDQ-UHFFFAOYSA-N 1-chloro-2-methoxybenzene Chemical compound COC1=CC=CC=C1Cl QGRPVMLBTFGQDQ-UHFFFAOYSA-N 0.000 description 3
- JAXSPAXDDROBLQ-UHFFFAOYSA-N 2-chloro-4-(chloromethyl)-1-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1Cl JAXSPAXDDROBLQ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- RVQOLTBRWHPYTM-UHFFFAOYSA-N 1-(chloromethyl)-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=C(CCl)C=C1 RVQOLTBRWHPYTM-UHFFFAOYSA-N 0.000 description 2
- DUBCVXSYZVTCOC-UHFFFAOYSA-N 1-(chloromethyl)-4-ethylbenzene Chemical compound CCC1=CC=C(CCl)C=C1 DUBCVXSYZVTCOC-UHFFFAOYSA-N 0.000 description 2
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 2
- VFYLEHMWKPEVTA-UHFFFAOYSA-N 1-(chloromethyl)-4-prop-2-enoxybenzene Chemical compound ClCC1=CC=C(OCC=C)C=C1 VFYLEHMWKPEVTA-UHFFFAOYSA-N 0.000 description 2
- CYAKWEQUWJAHLW-UHFFFAOYSA-N 1-(chloromethyl)-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(CCl)C=C1 CYAKWEQUWJAHLW-UHFFFAOYSA-N 0.000 description 2
- MNWIWTZKCATVSP-UHFFFAOYSA-N 1-(chloromethyl)-4-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=C(CCl)C=C1 MNWIWTZKCATVSP-UHFFFAOYSA-N 0.000 description 2
- CDNWEVUZHGBTIV-UHFFFAOYSA-N 2-(3-chloro-4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1Cl CDNWEVUZHGBTIV-UHFFFAOYSA-N 0.000 description 2
- YFJWKNWYIKMVQA-UHFFFAOYSA-N 2-[3-chloro-4-[(4-ethylphenyl)methoxy]phenyl]acetic acid Chemical compound C1=CC(CC)=CC=C1COC1=CC=C(CC(O)=O)C=C1Cl YFJWKNWYIKMVQA-UHFFFAOYSA-N 0.000 description 2
- BZYPVAZBDUBWHE-UHFFFAOYSA-N 2-[3-chloro-4-[(4-methoxyphenyl)methoxy]phenyl]acetic acid Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(CC(O)=O)C=C1Cl BZYPVAZBDUBWHE-UHFFFAOYSA-N 0.000 description 2
- OHGZSCXLSSWMKH-UHFFFAOYSA-N 2-[3-chloro-4-[(4-propan-2-yloxyphenyl)methoxy]phenyl]acetic acid Chemical compound C1=CC(OC(C)C)=CC=C1COC1=CC=C(CC(O)=O)C=C1Cl OHGZSCXLSSWMKH-UHFFFAOYSA-N 0.000 description 2
- HYPWEHDKOKVLRO-UHFFFAOYSA-N 2-[3-chloro-4-[(4-propan-2-ylphenyl)methoxy]phenyl]acetic acid Chemical compound C1=CC(C(C)C)=CC=C1COC1=CC=C(CC(O)=O)C=C1Cl HYPWEHDKOKVLRO-UHFFFAOYSA-N 0.000 description 2
- JPEXNRYOPURVQP-UHFFFAOYSA-N 2-[3-chloro-4-[[4-(2-methylpropoxy)phenyl]methoxy]phenyl]acetic acid Chemical compound C1=CC(OCC(C)C)=CC=C1COC1=CC=C(CC(O)=O)C=C1Cl JPEXNRYOPURVQP-UHFFFAOYSA-N 0.000 description 2
- XZECPLIMOPAQFE-UHFFFAOYSA-N 2-chloro-4-(chloromethyl)-1-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=C(CCl)C=C1Cl XZECPLIMOPAQFE-UHFFFAOYSA-N 0.000 description 2
- BHEHNICAPZVKRH-UHFFFAOYSA-N 4-(chloromethyl)-1-methoxy-2-methylbenzene Chemical compound COC1=CC=C(CCl)C=C1C BHEHNICAPZVKRH-UHFFFAOYSA-N 0.000 description 2
- NPSBMLMDVCSISR-UHFFFAOYSA-N 4-(chloromethyl)-2-methyl-1-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=C(CCl)C=C1C NPSBMLMDVCSISR-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- HJTAZXHBEBIQQX-UHFFFAOYSA-N 1,5-bis(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1CCl HJTAZXHBEBIQQX-UHFFFAOYSA-N 0.000 description 1
- UJVKKWVLMCDZDA-UHFFFAOYSA-N 1-chloro-2-(2-methylpropoxy)benzene Chemical compound CC(C)COC1=CC=CC=C1Cl UJVKKWVLMCDZDA-UHFFFAOYSA-N 0.000 description 1
- NQQZRGSSVFDPLC-UHFFFAOYSA-N 1-chloro-2-prop-2-enoxybenzene Chemical compound ClC1=CC=CC=C1OCC=C NQQZRGSSVFDPLC-UHFFFAOYSA-N 0.000 description 1
- YRGAYAGBVIXNAQ-UHFFFAOYSA-N 1-chloro-4-methoxybenzene Chemical compound COC1=CC=C(Cl)C=C1 YRGAYAGBVIXNAQ-UHFFFAOYSA-N 0.000 description 1
- ONNCZAPKYZWFHQ-UHFFFAOYSA-N 1-methyl-2-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=CC=C1C ONNCZAPKYZWFHQ-UHFFFAOYSA-N 0.000 description 1
- NVXSKDSPYQWBEF-UHFFFAOYSA-N 2-(3-chloro-4-phenylmethoxyphenyl)acetyl chloride Chemical compound ClC=1C=C(C=CC=1OCC1=CC=CC=C1)CC(=O)Cl NVXSKDSPYQWBEF-UHFFFAOYSA-N 0.000 description 1
- QYKCULKXKOEAQF-UHFFFAOYSA-N 2-[3-chloro-4-[(3-chloro-4-propan-2-yloxyphenyl)methoxy]phenyl]acetic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1COC1=CC=C(CC(O)=O)C=C1Cl QYKCULKXKOEAQF-UHFFFAOYSA-N 0.000 description 1
- VYPMPOZHKQERPC-UHFFFAOYSA-N 2-[3-chloro-4-[(3-methyl-4-propan-2-yloxyphenyl)methoxy]phenyl]acetic acid Chemical compound C1=C(C)C(OC(C)C)=CC=C1COC1=CC=C(CC(O)=O)C=C1Cl VYPMPOZHKQERPC-UHFFFAOYSA-N 0.000 description 1
- SRPQARZJSFDFLV-UHFFFAOYSA-N 2-[3-chloro-4-[(4-methoxy-3-methylphenyl)methoxy]phenyl]acetic acid Chemical compound C1=C(C)C(OC)=CC=C1COC1=CC=C(CC(O)=O)C=C1Cl SRPQARZJSFDFLV-UHFFFAOYSA-N 0.000 description 1
- DGGTZSYAMNWDGI-UHFFFAOYSA-N 2-[3-chloro-4-[[3-chloro-4-(2-methylpropoxy)phenyl]methoxy]phenyl]acetic acid Chemical compound C1=C(Cl)C(OCC(C)C)=CC=C1COC1=CC=C(CC(O)=O)C=C1Cl DGGTZSYAMNWDGI-UHFFFAOYSA-N 0.000 description 1
- LNGNTTDTWJWVTL-UHFFFAOYSA-N 2-[3-chloro-4-[[4-(2-methylpropyl)phenyl]methoxy]phenyl]acetic acid Chemical compound C1=CC(CC(C)C)=CC=C1COC1=CC=C(CC(O)=O)C=C1Cl LNGNTTDTWJWVTL-UHFFFAOYSA-N 0.000 description 1
- IMQHYLURBWYPOM-UHFFFAOYSA-N 2-chloro-4-(chloromethyl)-1-(2-methylpropoxy)benzene Chemical compound CC(C)COC1=CC=C(CCl)C=C1Cl IMQHYLURBWYPOM-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 1
- ONNUYWHIJSKABC-UHFFFAOYSA-N 2-methylpropoxybenzene Chemical compound CC(C)COC1=CC=CC=C1 ONNUYWHIJSKABC-UHFFFAOYSA-N 0.000 description 1
- ZGAJGFUIIQGVFQ-UHFFFAOYSA-N 2-methylpropyl 2-(3-chloro-4-phenylmethoxyphenyl)acetate Chemical compound ClC1=CC(CC(=O)OCC(C)C)=CC=C1OCC1=CC=CC=C1 ZGAJGFUIIQGVFQ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 241000700159 Rattus Species 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
- YVBSAPDHRXHFHV-UHFFFAOYSA-N [chloro(methoxy)methyl]benzene Chemical compound COC(Cl)C1=CC=CC=C1 YVBSAPDHRXHFHV-UHFFFAOYSA-N 0.000 description 1
- MNZMECMQTYGSOI-UHFFFAOYSA-N acetic acid;hydron;bromide Chemical compound Br.CC(O)=O MNZMECMQTYGSOI-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 1
- RQNWIZPPADIBDY-AKLPVKDBSA-N arsenic-78 Chemical compound [78As] RQNWIZPPADIBDY-AKLPVKDBSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 150000005524 benzylchlorides Chemical class 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- ZYNMJJNWXVKJJV-UHFFFAOYSA-N propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=CC=C1 ZYNMJJNWXVKJJV-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS8681A CS175831B1 (nl) | 1974-12-17 | 1974-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH619205A5 true CH619205A5 (nl) | 1980-09-15 |
Family
ID=5437722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1592575A CH619205A5 (nl) | 1974-12-17 | 1975-12-08 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4221919A (nl) |
| JP (1) | JPS5186442A (nl) |
| AT (1) | AT341506B (nl) |
| BE (1) | BE836679A (nl) |
| CA (1) | CA1074330A (nl) |
| CH (1) | CH619205A5 (nl) |
| CS (1) | CS175831B1 (nl) |
| DE (1) | DE2556474C2 (nl) |
| DK (1) | DK143552C (nl) |
| FI (1) | FI60195C (nl) |
| FR (1) | FR2294689A1 (nl) |
| GB (1) | GB1487149A (nl) |
| NL (1) | NL7514725A (nl) |
| SE (1) | SE427108B (nl) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8400239D0 (sv) * | 1984-01-19 | 1984-01-19 | Pharmacia Ab | Nya arylettiksyraderivat |
| US6638977B1 (en) | 1999-11-19 | 2003-10-28 | Corvas International, Inc. | Plasminogen activator inhibitor antagonists |
| AU1624801A (en) | 1999-11-19 | 2001-05-30 | Corvas International, Inc. | Plasminogen activator inhibitor antagonists related applications |
| GB0214149D0 (en) * | 2002-06-19 | 2002-07-31 | Glaxo Group Ltd | Chemical compounds |
| BRPI0407506A (pt) | 2003-02-13 | 2006-02-14 | Wellstat Therapeutics Corp | compostos para o tratamento de distúrbios metabólicos, seu uso e composição farmacêutica compreendendo os mesmos |
| US20050130987A1 (en) * | 2003-10-14 | 2005-06-16 | Wyeth | Methods of treating vasomotor symptoms |
| US7491723B2 (en) | 2003-10-14 | 2009-02-17 | Wyeth | Alkanol and cycloalkanol-amine derivatives and methods of their use |
| US7550485B2 (en) | 2003-10-14 | 2009-06-23 | Wyeth | Substituted N-heterocycle derivatives and methods of their use |
| US7524846B2 (en) | 2003-10-14 | 2009-04-28 | Wyeth | Arylalkyl- and cycloalkylalkyl-piperazine derivatives and methods of their use |
| US7365076B2 (en) | 2003-10-14 | 2008-04-29 | Wyeth | Substituted aryl cycloalkanol derivatives and methods of their use |
| US7402698B2 (en) | 2003-10-14 | 2008-07-22 | Wyeth | Secondary amino-and cycloamino-cycloalkanol derivatives and methods of their use |
| US7531543B2 (en) | 2003-10-14 | 2009-05-12 | Wyeth | Phenylpiperazine cycloalkanol derivatives and methods of their use |
| US7419980B2 (en) | 2003-10-14 | 2008-09-02 | Wyeth | Fused-aryl and heteroaryl derivatives and methods of their use |
| US7517899B2 (en) * | 2004-03-30 | 2009-04-14 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| US7414052B2 (en) | 2004-03-30 | 2008-08-19 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| UA95613C2 (ru) * | 2005-11-09 | 2011-08-25 | Уеллстат Терепьютикс Корпорейшн | Соединения для лечения расстройсв метаболизма |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1459084A (en) * | 1973-05-24 | 1976-12-22 | Boots Co Ltd | Preparation of arylalkanoic acid |
-
1974
- 1974-12-17 CS CS8681A patent/CS175831B1/cs unknown
-
1975
- 1975-12-08 CH CH1592575A patent/CH619205A5/de not_active IP Right Cessation
- 1975-12-12 GB GB50958/75A patent/GB1487149A/en not_active Expired
- 1975-12-15 DE DE2556474A patent/DE2556474C2/de not_active Expired
- 1975-12-16 SE SE7514212A patent/SE427108B/xx unknown
- 1975-12-16 FI FI753551A patent/FI60195C/fi not_active IP Right Cessation
- 1975-12-16 BE BE162774A patent/BE836679A/xx not_active IP Right Cessation
- 1975-12-16 AT AT953075A patent/AT341506B/de not_active IP Right Cessation
- 1975-12-17 DK DK573475A patent/DK143552C/da not_active IP Right Cessation
- 1975-12-17 FR FR7538606A patent/FR2294689A1/fr active Granted
- 1975-12-17 NL NL7514725A patent/NL7514725A/nl not_active Application Discontinuation
- 1975-12-17 CA CA242,207A patent/CA1074330A/en not_active Expired
- 1975-12-17 JP JP50149660A patent/JPS5186442A/ja active Pending
-
1979
- 1979-04-24 US US06/033,147 patent/US4221919A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2294689B1 (nl) | 1978-12-01 |
| DK573475A (da) | 1976-06-18 |
| DK143552B (da) | 1981-09-07 |
| BE836679A (fr) | 1976-04-16 |
| JPS5186442A (nl) | 1976-07-29 |
| GB1487149A (en) | 1977-09-28 |
| DE2556474C2 (de) | 1984-08-09 |
| FR2294689A1 (fr) | 1976-07-16 |
| CA1074330A (en) | 1980-03-25 |
| DE2556474A1 (de) | 1976-07-01 |
| CS175831B1 (nl) | 1977-05-31 |
| FI753551A (nl) | 1976-06-18 |
| NL7514725A (nl) | 1976-06-21 |
| AT341506B (de) | 1978-02-10 |
| SE427108B (sv) | 1983-03-07 |
| DK143552C (da) | 1982-02-08 |
| ATA953075A (de) | 1977-06-15 |
| US4221919A (en) | 1980-09-09 |
| FI60195B (fi) | 1981-08-31 |
| SE7514212L (sv) | 1976-06-18 |
| FI60195C (fi) | 1981-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |