BE458801A - - Google Patents
Info
- Publication number
- BE458801A BE458801A BE458801DA BE458801A BE 458801 A BE458801 A BE 458801A BE 458801D A BE458801D A BE 458801DA BE 458801 A BE458801 A BE 458801A
- Authority
- BE
- Belgium
- Prior art keywords
- acid
- amide
- acetic acid
- hydroxy
- phenoxy
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 36
- -1 amino- Chemical class 0.000 claims description 26
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 8
- 230000001034 aminogenic effect Effects 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229960004275 glycolic acid Drugs 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 7
- 229940124530 sulfonamide Drugs 0.000 description 7
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 150000003456 sulfonamides Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical class CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- QWKKYJLAUWFPDB-UHFFFAOYSA-N 4-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QWKKYJLAUWFPDB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 235000013832 Valeriana officinalis Nutrition 0.000 description 3
- 244000126014 Valeriana officinalis Species 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000565 sulfonamide group Chemical group 0.000 description 3
- 235000016788 valerian Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 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 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- HGTBAIVLETUVCG-UHFFFAOYSA-N (methylthio)acetic acid Chemical compound CSCC(O)=O HGTBAIVLETUVCG-UHFFFAOYSA-N 0.000 description 1
- ULRHANCBHWLRPM-UHFFFAOYSA-N 2-(2,5-dimethylphenoxy)acetamide Chemical compound CC1=CC=C(C)C(OCC(N)=O)=C1 ULRHANCBHWLRPM-UHFFFAOYSA-N 0.000 description 1
- GOVBTAZVUFGTFB-UHFFFAOYSA-N 2-(3-methylphenoxy)acetamide Chemical compound CC1=CC=CC(OCC(N)=O)=C1 GOVBTAZVUFGTFB-UHFFFAOYSA-N 0.000 description 1
- VZECTCSEONQIPP-UHFFFAOYSA-N 2-(3-methylphenoxy)acetic acid Chemical compound CC1=CC=CC(OCC(O)=O)=C1 VZECTCSEONQIPP-UHFFFAOYSA-N 0.000 description 1
- DTVFPSLQRRXKQW-UHFFFAOYSA-N 2-(4-pentylphenoxy)acetic acid Chemical compound CCCCCC1=CC=C(OCC(O)=O)C=C1 DTVFPSLQRRXKQW-UHFFFAOYSA-N 0.000 description 1
- DMJDGSYFXJOVEB-UHFFFAOYSA-N 2-(cyclohexen-1-yl)-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CCCCC1 DMJDGSYFXJOVEB-UHFFFAOYSA-N 0.000 description 1
- LIRSBWNZCJMZND-UHFFFAOYSA-N 2-(cyclopentylmethoxy)acetic acid Chemical compound OC(=O)COCC1CCCC1 LIRSBWNZCJMZND-UHFFFAOYSA-N 0.000 description 1
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 1
- AWLVTQRRKPBQEQ-UHFFFAOYSA-N 2-benzylsulfanylacetic acid Chemical compound OC(=O)CSCC1=CC=CC=C1 AWLVTQRRKPBQEQ-UHFFFAOYSA-N 0.000 description 1
- UJPXNCODVPXBRK-UHFFFAOYSA-N 2-cycloheptyl-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1CCCCCC1 UJPXNCODVPXBRK-UHFFFAOYSA-N 0.000 description 1
- QOLYWZBRASBMKV-UHFFFAOYSA-N 2-cyclohexyl-2-ethoxyacetic acid Chemical compound CCOC(C(O)=O)C1CCCCC1 QOLYWZBRASBMKV-UHFFFAOYSA-N 0.000 description 1
- WHZPPIIMQBJUHW-UHFFFAOYSA-N 2-cyclopentyl-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1CCCC1 WHZPPIIMQBJUHW-UHFFFAOYSA-N 0.000 description 1
- NIZGLRRRDIMCNI-UHFFFAOYSA-N 2-cyclopentyl-2-phenoxyacetic acid Chemical compound C1CCCC1C(C(=O)O)OC1=CC=CC=C1 NIZGLRRRDIMCNI-UHFFFAOYSA-N 0.000 description 1
- JLLRJAYEZDANQR-UHFFFAOYSA-N 2-cyclopentyl-2-sulfanylacetic acid Chemical compound OC(=O)C(S)C1CCCC1 JLLRJAYEZDANQR-UHFFFAOYSA-N 0.000 description 1
- OAAKFAXUEYTMHF-UHFFFAOYSA-N 2-ethoxyacetamide Chemical compound CCOCC(N)=O OAAKFAXUEYTMHF-UHFFFAOYSA-N 0.000 description 1
- KBGVKUVSFWHFPS-UHFFFAOYSA-N 2-ethoxyoctanoic acid Chemical compound CCCCCCC(C(O)=O)OCC KBGVKUVSFWHFPS-UHFFFAOYSA-N 0.000 description 1
- VJIKFWJCVWFZIN-UHFFFAOYSA-N 2-ethylsulfanylacetic acid Chemical compound CCSCC(O)=O VJIKFWJCVWFZIN-UHFFFAOYSA-N 0.000 description 1
- YMAXCKYGIGCLPM-UHFFFAOYSA-N 2-heptoxyacetic acid Chemical compound CCCCCCCOCC(O)=O YMAXCKYGIGCLPM-UHFFFAOYSA-N 0.000 description 1
- HJOGHUABHYACMH-UHFFFAOYSA-N 2-hexoxyacetic acid Chemical compound CCCCCCOCC(O)=O HJOGHUABHYACMH-UHFFFAOYSA-N 0.000 description 1
- PVAQRTBQTOOWOQ-UHFFFAOYSA-N 2-hydroxy-3-(3-methylphenyl)propanoic acid Chemical compound CC1=CC=CC(CC(O)C(O)=O)=C1 PVAQRTBQTOOWOQ-UHFFFAOYSA-N 0.000 description 1
- RYMIVJFDSJKWSI-UHFFFAOYSA-N 2-hydroxy-5-phenylpent-4-enoic acid Chemical compound OC(=O)C(O)CC=CC1=CC=CC=C1 RYMIVJFDSJKWSI-UHFFFAOYSA-N 0.000 description 1
- MTEZLAATISORQK-UHFFFAOYSA-N 2-methoxyacetamide Chemical compound COCC(N)=O MTEZLAATISORQK-UHFFFAOYSA-N 0.000 description 1
- JKUNYOVTULTVIA-UHFFFAOYSA-N 2-methyl-2-phenoxypropanamide Chemical compound NC(=O)C(C)(C)OC1=CC=CC=C1 JKUNYOVTULTVIA-UHFFFAOYSA-N 0.000 description 1
- HPSBYYHIHGQARI-UHFFFAOYSA-N 2-octoxyacetic acid Chemical compound CCCCCCCCOCC(O)=O HPSBYYHIHGQARI-UHFFFAOYSA-N 0.000 description 1
- YIKIRNROKVZLML-UHFFFAOYSA-N 2-pentoxyacetic acid Chemical compound CCCCCOCC(O)=O YIKIRNROKVZLML-UHFFFAOYSA-N 0.000 description 1
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 1
- VKHMCMHMKVAQEK-UHFFFAOYSA-N 2-phenyl-2-sulfanylacetamide Chemical compound NC(=O)C(S)C1=CC=CC=C1 VKHMCMHMKVAQEK-UHFFFAOYSA-N 0.000 description 1
- WOMBHFDZBLZRLM-UHFFFAOYSA-N 2-propan-2-yloxyacetamide Chemical compound CC(C)OCC(N)=O WOMBHFDZBLZRLM-UHFFFAOYSA-N 0.000 description 1
- OAIRTVZAAFZBMR-UHFFFAOYSA-N 2-propan-2-yloxyacetic acid Chemical compound CC(C)OCC(O)=O OAIRTVZAAFZBMR-UHFFFAOYSA-N 0.000 description 1
- SGUYGLMQEOSQTH-UHFFFAOYSA-N 2-propoxyacetic acid Chemical compound CCCOCC(O)=O SGUYGLMQEOSQTH-UHFFFAOYSA-N 0.000 description 1
- QXDUMOMMZMHKOH-UHFFFAOYSA-N 2-sulfanylpentanamide Chemical compound CCCC(S)C(N)=O QXDUMOMMZMHKOH-UHFFFAOYSA-N 0.000 description 1
- IMGGANUNCHXAQF-UHFFFAOYSA-N 2-sulfanylpentanoic acid Chemical compound CCCC(S)C(O)=O IMGGANUNCHXAQF-UHFFFAOYSA-N 0.000 description 1
- WGVNJQHQQWPGJL-UHFFFAOYSA-N 3-ethoxypropanamide Chemical compound CCOCCC(N)=O WGVNJQHQQWPGJL-UHFFFAOYSA-N 0.000 description 1
- OLRAVBOBAFNKHF-UHFFFAOYSA-N 3-methyl-2-phenoxybutanamide Chemical compound CC(C)C(C(N)=O)OC1=CC=CC=C1 OLRAVBOBAFNKHF-UHFFFAOYSA-N 0.000 description 1
- JUJFUNIPPVHBID-UHFFFAOYSA-N 3-phenoxypropanamide Chemical compound NC(=O)CCOC1=CC=CC=C1 JUJFUNIPPVHBID-UHFFFAOYSA-N 0.000 description 1
- JNVSNCYKZKYJFM-UHFFFAOYSA-N 3-phenyl-2-propoxypropanoic acid Chemical compound CCCOC(C(O)=O)CC1=CC=CC=C1 JNVSNCYKZKYJFM-UHFFFAOYSA-N 0.000 description 1
- FFAKQPMACMIZAF-UHFFFAOYSA-N 3-propan-2-yloxypropanamide Chemical compound CC(C)OCCC(N)=O FFAKQPMACMIZAF-UHFFFAOYSA-N 0.000 description 1
- PAGQDRJLHDGJDP-UHFFFAOYSA-N 6-phenoxyhexanamide Chemical compound NC(=O)CCCCCOC1=CC=CC=C1 PAGQDRJLHDGJDP-UHFFFAOYSA-N 0.000 description 1
- 101150034533 ATIC gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical compound COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- GNHQSAUHXKRQMC-UHFFFAOYSA-N benzene;chlorine Chemical compound [Cl].C1=CC=CC=C1 GNHQSAUHXKRQMC-UHFFFAOYSA-N 0.000 description 1
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- FHSWXOCOMAVQKE-UHFFFAOYSA-N phenylazanium;acetate Chemical compound CC([O-])=O.[NH3+]C1=CC=CC=C1 FHSWXOCOMAVQKE-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- WEZYFYMYMKUAHY-UHFFFAOYSA-N tert-butyl 2,4-dibenzylpiperazine-1-carboxylate Chemical compound C1C(CC=2C=CC=CC=2)N(C(=O)OC(C)(C)C)CCN1CC1=CC=CC=C1 WEZYFYMYMKUAHY-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE458801A true BE458801A (enrdf_load_html_response) |
Family
ID=112019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE458801D BE458801A (enrdf_load_html_response) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE458801A (enrdf_load_html_response) |
-
0
- BE BE458801D patent/BE458801A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0245156B1 (fr) | Nouveau procédé de préparation de fibrates | |
| HU183085B (en) | Process for preparing new phenoxy-alkyl-carboxylic acid derivatives and pharmaceutical compositions containing thereof | |
| BE531090A (fr) | Procédé pour la production de dérivés substitués du 1-3-4-thiadiazol | |
| BE458801A (enrdf_load_html_response) | ||
| EP0177414A1 (fr) | Composés triaminobenzéniques iodés, leur procédé de préparation et leur application dans des produits de contraste | |
| EP0357467B1 (fr) | Nouveaux composés triiodobenzéniques non ioniques iodés et produits de contraste les contenant | |
| CA1280443C (fr) | Composes polyfluoroalkylthio-methyliques, leurs procedes de preparation et leurs applications comme agents tensio-actifs ou precurseurs de ces derniers | |
| FR2695125A1 (fr) | Nouveaux composés poly-iodés, procédé de préparation, produit de contraste les contenant. | |
| EP0497678A1 (fr) | Diaryl-2,5, oxadiazoles-1,3,4, hydroxyesters, hydroxyacide et acétoxyacide, leur procédé de synthèse | |
| WO1988008417A1 (fr) | Composes diamino benzeniques iodes, leur procede de preparation et produits de contraste les contenant | |
| FR2578539A1 (fr) | Nouveaux benzamides de l'acide 2,4,6-trimethoxybenzoique, leur procede de preparation et leur utilisation | |
| CH653325A5 (en) | Process for synthesis of 1-(4-isopropylthiophenyl)-2-(n-octylamino)propanol, of its esters and of its salts | |
| CH516523A (fr) | Procédé de préparation des dérivés des acides a-aminés N-disubstitués par benzoylation | |
| CA1186326A (fr) | Derives d'acrylamides hydroxyles et leur preparation | |
| BE504403A (enrdf_load_html_response) | ||
| BE468368A (enrdf_load_html_response) | ||
| BE445333A (enrdf_load_html_response) | ||
| BE684910A (enrdf_load_html_response) | ||
| BE481598A (enrdf_load_html_response) | ||
| BE451559A (enrdf_load_html_response) | ||
| BE446264A (enrdf_load_html_response) | ||
| BE568697A (enrdf_load_html_response) | ||
| BE474163A (enrdf_load_html_response) | ||
| BE833266A (fr) | Procede de preparation d'acides 2-arylpropioniques et acides obtenus | |
| FR2725203A1 (fr) | Procede de synthese de disulfures dissymetriques et nouveaux disulfures dissymetriques benzyliques obtenus par ce procede |