CA1082191A - Process for the preparation of sulfamylbenzoic acids - Google Patents
Process for the preparation of sulfamylbenzoic acidsInfo
- Publication number
- CA1082191A CA1082191A CA251,343A CA251343A CA1082191A CA 1082191 A CA1082191 A CA 1082191A CA 251343 A CA251343 A CA 251343A CA 1082191 A CA1082191 A CA 1082191A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- acid
- methyl ester
- defined above
- acid methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims abstract description 96
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 150000007513 acids Chemical class 0.000 title abstract description 12
- 125000006239 protecting group Chemical group 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 45
- -1 amino, phenyl-thio Chemical group 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 20
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910010277 boron hydride Inorganic materials 0.000 claims description 13
- 239000002841 Lewis acid Substances 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 150000007517 lewis acids Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- KDNIOKSLVIGAAN-UHFFFAOYSA-N 2-sulfamoylbenzoic acid Chemical class NS(=O)(=O)C1=CC=CC=C1C(O)=O KDNIOKSLVIGAAN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 79
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 73
- 239000000243 solution Substances 0.000 description 73
- 150000004702 methyl esters Chemical class 0.000 description 64
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
- 235000013350 formula milk Nutrition 0.000 description 50
- 238000002844 melting Methods 0.000 description 49
- 230000008018 melting Effects 0.000 description 49
- 229910001868 water Inorganic materials 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000013078 crystal Substances 0.000 description 26
- 229940022682 acetone Drugs 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000007868 Raney catalyst Substances 0.000 description 10
- 229910000564 Raney nickel Inorganic materials 0.000 description 10
- 239000012279 sodium borohydride Substances 0.000 description 10
- 229910000033 sodium borohydride Inorganic materials 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 229910015900 BF3 Inorganic materials 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000005711 Benzoic acid Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229960004365 benzoic acid Drugs 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000006396 nitration reaction Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QQDJVXQOPBLBIG-UHFFFAOYSA-N 3-(cyclopropylmethylamino)-4-(4-nitrophenoxy)-5-sulfamoylbenzoic acid Chemical compound C=1C=C([N+]([O-])=O)C=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1NCC1CC1 QQDJVXQOPBLBIG-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 208000036366 Sensation of pressure Diseases 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000001376 precipitating effect Effects 0.000 description 4
- NAETXYOXMDYNLE-UHFFFAOYSA-N 3-sulfamoylbenzoic acid Chemical class NS(=O)(=O)C1=CC=CC(C(O)=O)=C1 NAETXYOXMDYNLE-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 230000000802 nitrating effect Effects 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003860 tertiary carboxamides Chemical class 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 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
- VSOOBQALJVLTBH-UHFFFAOYSA-N 2-aminosulfonyl-benzoic acid methyl ester Chemical compound COC(=O)C1=CC=CC=C1S(N)(=O)=O VSOOBQALJVLTBH-UHFFFAOYSA-N 0.000 description 2
- NWYUVKPGSQYOQU-UHFFFAOYSA-N 3-(cyclobutylmethylamino)-4-phenylsulfanyl-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1SC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1NCC1CCC1 NWYUVKPGSQYOQU-UHFFFAOYSA-N 0.000 description 2
- XIQFXPIMKODPRV-UHFFFAOYSA-N 3-(cyclopropylmethylamino)-4-(4-hydroxyphenoxy)-5-sulfamoylbenzoic acid Chemical compound C=1C=C(O)C=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1NCC1CC1 XIQFXPIMKODPRV-UHFFFAOYSA-N 0.000 description 2
- FHIIAYKDWXYOBF-UHFFFAOYSA-N 3-(cyclopropylmethylamino)-4-(4-methylphenoxy)-5-sulfamoylbenzoic acid Chemical compound C1=CC(C)=CC=C1OC(C(=CC(=C1)C(O)=O)S(N)(=O)=O)=C1NCC1CC1 FHIIAYKDWXYOBF-UHFFFAOYSA-N 0.000 description 2
- MKOFSDUQCWFPIG-UHFFFAOYSA-N 3-(cyclopropylmethylamino)-4-phenoxy-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1NCC1CC1 MKOFSDUQCWFPIG-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- JFWMYCVMQSLLOO-UHFFFAOYSA-N cyclobutanecarbonyl chloride Chemical compound ClC(=O)C1CCC1 JFWMYCVMQSLLOO-UHFFFAOYSA-N 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 229940030606 diuretics Drugs 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- CXNFUAIWZFIMAK-UHFFFAOYSA-N methyl 2-(aminomethylideneamino)sulfonylbenzoate Chemical compound COC(C1=C(C=CC=C1)S(=O)(=O)N=CN)=O CXNFUAIWZFIMAK-UHFFFAOYSA-N 0.000 description 2
- JOSXWVDKEHFFRY-UHFFFAOYSA-N methyl 2-(methylideneamino)sulfonylbenzoate Chemical compound COC(C1=C(C=CC=C1)S(=O)(=O)N=C)=O JOSXWVDKEHFFRY-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 230000000894 saliuretic effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 1
- XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- ZZTYSYZHDBRDFC-UHFFFAOYSA-N 2-(dimethylaminomethylideneamino)sulfonylbenzoic acid Chemical compound CN(C)C=NS(=O)(=O)C1=C(C(=O)O)C=CC=C1 ZZTYSYZHDBRDFC-UHFFFAOYSA-N 0.000 description 1
- RMAINTGPKFNBDP-UHFFFAOYSA-N 2-methylphenol Chemical compound [CH2]C1=CC=CC=C1O RMAINTGPKFNBDP-UHFFFAOYSA-N 0.000 description 1
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-di-methylphenol Natural products CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 1
- VSSZKXRAUHZJFV-UHFFFAOYSA-N 3,5-dimethylphenol Chemical compound CC1=CC(C)=CC(O)=C1.CC1=CC(C)=CC(O)=C1 VSSZKXRAUHZJFV-UHFFFAOYSA-N 0.000 description 1
- PUIUOPTWELLSSI-UHFFFAOYSA-N 3-(2-phenylethylamino)-4-phenylsulfanyl-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1SC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1NCCC1=CC=CC=C1 PUIUOPTWELLSSI-UHFFFAOYSA-N 0.000 description 1
- DXLANCVSXGODDB-UHFFFAOYSA-N 3-(benzylamino)-4-phenylsulfanyl-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1SC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1NCC1=CC=CC=C1 DXLANCVSXGODDB-UHFFFAOYSA-N 0.000 description 1
- LUOGKJOANZHULY-UHFFFAOYSA-N 3-(cyclobutylmethylamino)-4-phenoxy-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1NCC1CCC1 LUOGKJOANZHULY-UHFFFAOYSA-N 0.000 description 1
- OTTOMYXKDJTLCM-UHFFFAOYSA-N 3-(cyclopropylmethylamino)-4-(2,4-dimethylphenoxy)-5-sulfamoylbenzoic acid Chemical compound CC1=CC(C)=CC=C1OC(C(=CC(=C1)C(O)=O)S(N)(=O)=O)=C1NCC1CC1 OTTOMYXKDJTLCM-UHFFFAOYSA-N 0.000 description 1
- NTVNIWUGYCYASO-UHFFFAOYSA-N 3-(cyclopropylmethylamino)-4-(4-methoxyphenoxy)-5-sulfamoylbenzoic acid Chemical compound C1=CC(OC)=CC=C1OC(C(=CC(=C1)C(O)=O)S(N)(=O)=O)=C1NCC1CC1 NTVNIWUGYCYASO-UHFFFAOYSA-N 0.000 description 1
- JKFVFLHUFDGWBY-UHFFFAOYSA-N 3-(cyclopropylmethylamino)-4-[4-(ethylamino)phenoxy]-5-sulfamoylbenzoic acid Chemical compound C1=CC(NCC)=CC=C1OC(C(=CC(=C1)C(O)=O)S(N)(=O)=O)=C1NCC1CC1 JKFVFLHUFDGWBY-UHFFFAOYSA-N 0.000 description 1
- ISTCGIYVZKGRGT-UHFFFAOYSA-N 3-(cyclopropylmethylamino)-4-phenylsulfanyl-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1SC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1NCC1CC1 ISTCGIYVZKGRGT-UHFFFAOYSA-N 0.000 description 1
- KQDOWULTFRAYRS-UHFFFAOYSA-N 3-(furan-2-ylmethylamino)-4-phenoxy-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1NCC1=CC=CO1 KQDOWULTFRAYRS-UHFFFAOYSA-N 0.000 description 1
- QYYMPVUVIYDMSE-UHFFFAOYSA-N 3-(furan-2-ylmethylamino)-4-phenylsulfanyl-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1SC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1NCC1=CC=CO1 QYYMPVUVIYDMSE-UHFFFAOYSA-N 0.000 description 1
- UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 description 1
- CBVUJBHCGUGMJN-UHFFFAOYSA-N 3-butyl-4-phenoxy-5-sulfamoylbenzoic acid Chemical compound C(CCC)C=1C=C(C(=O)O)C=C(C=1OC1=CC=CC=C1)S(N)(=O)=O CBVUJBHCGUGMJN-UHFFFAOYSA-N 0.000 description 1
- OQVCXNXXIOORAC-UHFFFAOYSA-N 4-(2,4-dimethylphenoxy)-3-(2-phenylethylamino)-5-sulfamoylbenzoic acid Chemical compound C1(=CC=CC=C1)CCNC=1C=C(C(=O)O)C=C(C1OC1=C(C=C(C=C1)C)C)S(N)(=O)=O OQVCXNXXIOORAC-UHFFFAOYSA-N 0.000 description 1
- NUOUYZJKFXNRFJ-UHFFFAOYSA-N 4-(4-aminophenoxy)-3-(2-phenylethylamino)-5-sulfamoylbenzoic acid Chemical compound C1(=CC=CC=C1)CCNC=1C=C(C(=O)O)C=C(C=1OC1=CC=C(C=C1)N)S(N)(=O)=O NUOUYZJKFXNRFJ-UHFFFAOYSA-N 0.000 description 1
- HXERBGRAMZRRBL-UHFFFAOYSA-N 4-(4-aminophenoxy)-3-(cyclopropylmethylamino)-5-sulfamoylbenzoic acid Chemical compound C1=CC(N)=CC=C1OC(C(=CC(=C1)C(O)=O)S(N)(=O)=O)=C1NCC1CC1 HXERBGRAMZRRBL-UHFFFAOYSA-N 0.000 description 1
- ALJCKWWVDBTCGK-UHFFFAOYSA-N 4-(4-chlorophenoxy)-3-(2-phenylethylamino)-5-sulfamoylbenzoic acid Chemical compound C1(=CC=CC=C1)CCNC=1C=C(C(=O)O)C=C(C1OC1=CC=C(C=C1)Cl)S(N)(=O)=O ALJCKWWVDBTCGK-UHFFFAOYSA-N 0.000 description 1
- PJXNGXJSJHMQFE-UHFFFAOYSA-N 4-(4-methoxyphenoxy)-3-(2-phenylethylamino)-5-sulfamoylbenzoic acid Chemical compound C1(=CC=CC=C1)CCNC=1C=C(C(=O)O)C=C(C=1OC1=CC=C(C=C1)OC)S(N)(=O)=O PJXNGXJSJHMQFE-UHFFFAOYSA-N 0.000 description 1
- DEEPYSWNWNPDQV-UHFFFAOYSA-N 4-(4-methylphenoxy)-3-(2-phenylethylamino)-5-sulfamoylbenzoic acid Chemical compound C1(=CC=CC=C1)CCNC=1C=C(C(=O)O)C=C(C=1OC1=CC=C(C=C1)C)S(N)(=O)=O DEEPYSWNWNPDQV-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- LGGIPTBAOFNXDV-UHFFFAOYSA-N 4-[4-(ethylamino)phenoxy]-3-(2-phenylethylamino)-5-sulfamoylbenzoic acid Chemical compound C1(=CC=CC=C1)CCNC=1C=C(C(=O)O)C=C(C1OC1=CC=C(C=C1)NCC)S(N)(=O)=O LGGIPTBAOFNXDV-UHFFFAOYSA-N 0.000 description 1
- HLOODOZAHCJKBE-UHFFFAOYSA-N 4-chloro-2-(dimethylaminomethylideneamino)sulfonyl-3-nitrobenzoic acid Chemical compound [N+](=O)([O-])C=1C(=C(C(=O)O)C=CC=1Cl)S(=O)(=O)N=CN(C)C HLOODOZAHCJKBE-UHFFFAOYSA-N 0.000 description 1
- FHQAWINGVCDTTG-UHFFFAOYSA-N 4-chloro-3-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=CC=C1Cl FHQAWINGVCDTTG-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 1
- ZVEWFTICTSQBDM-UHFFFAOYSA-N 4-methylphenol Chemical compound [CH2]C1=CC=C(O)C=C1 ZVEWFTICTSQBDM-UHFFFAOYSA-N 0.000 description 1
- RGXMLGOOOUDRJY-UHFFFAOYSA-N 4-phenoxy-3-(2-phenylethylamino)-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1NCCC1=CC=CC=C1 RGXMLGOOOUDRJY-UHFFFAOYSA-N 0.000 description 1
- FPVUWZFFEGYCGB-UHFFFAOYSA-N 5-methyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CC1=NN=C(S)S1 FPVUWZFFEGYCGB-UHFFFAOYSA-N 0.000 description 1
- 101100372602 Arabidopsis thaliana VDAC3 gene Proteins 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 101100229907 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) GPP2 gene Proteins 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical class [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- MAEIEVLCKWDQJH-UHFFFAOYSA-N bumetanide Chemical compound CCCCNC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 MAEIEVLCKWDQJH-UHFFFAOYSA-N 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- YBERTMQAGHYOFM-UHFFFAOYSA-N methyl 2-(dimethylaminomethylideneamino)sulfonylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)N=CN(C)C YBERTMQAGHYOFM-UHFFFAOYSA-N 0.000 description 1
- KXIDZTLANKUQPQ-UHFFFAOYSA-N methyl 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoate Chemical compound CCCCNC1=CC(C(=O)OC)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 KXIDZTLANKUQPQ-UHFFFAOYSA-N 0.000 description 1
- QBPGIJAQYJIXDS-UHFFFAOYSA-N methyl 3-(cyclopropylmethylamino)-4-(4-methylphenoxy)-5-sulfamoylbenzoate Chemical compound COC(C1=CC(=C(C(=C1)S(N)(=O)=O)OC1=CC=C(C=C1)C)NCC1CC1)=O QBPGIJAQYJIXDS-UHFFFAOYSA-N 0.000 description 1
- MEPRRLRSOIESKI-UHFFFAOYSA-N methyl 6-sulfonylcyclohexa-2,4-diene-1-carboxylate Chemical compound COC(=O)C1C=CC=CC1=S(=O)=O MEPRRLRSOIESKI-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N para-hydroxytoluene Natural products CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- WPZAAASEHYSQIQ-UHFFFAOYSA-M phenyl(pyridin-1-ium-1-yl)methanone;chloride Chemical compound [Cl-].C=1C=CC=C[N+]=1C(=O)C1=CC=CC=C1 WPZAAASEHYSQIQ-UHFFFAOYSA-M 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- HMSLXWQWEJXFFR-UHFFFAOYSA-M potassium;4-chlorophenolate Chemical compound [K+].[O-]C1=CC=C(Cl)C=C1 HMSLXWQWEJXFFR-UHFFFAOYSA-M 0.000 description 1
- OALPPYUMFWGHEK-UHFFFAOYSA-M potassium;benzenethiolate Chemical compound [K+].[S-]C1=CC=CC=C1 OALPPYUMFWGHEK-UHFFFAOYSA-M 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- FENGEGUDMXHOBU-UHFFFAOYSA-M sodium;4-fluorophenolate Chemical compound [Na+].[O-]C1=CC=C(F)C=C1 FENGEGUDMXHOBU-UHFFFAOYSA-M 0.000 description 1
- OCNITZXQILVVNT-UHFFFAOYSA-M sodium;4-phenylmethoxyphenolate Chemical compound [Na+].C1=CC([O-])=CC=C1OCC1=CC=CC=C1 OCNITZXQILVVNT-UHFFFAOYSA-M 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2518999.5 | 1975-04-29 | ||
| DE19752518999 DE2518999A1 (de) | 1975-04-29 | 1975-04-29 | Verfahren zur herstellung von sulfamylbenzoesaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1082191A true CA1082191A (en) | 1980-07-22 |
Family
ID=5945286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA251,343A Expired CA1082191A (en) | 1975-04-29 | 1976-04-28 | Process for the preparation of sulfamylbenzoic acids |
Country Status (10)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5375199A (en) * | 1976-12-15 | 1978-07-04 | Toda Kogyo Corp | Method of making acicular alphaa feooh particulates |
| ES482591A1 (es) * | 1978-07-20 | 1980-04-01 | Basf Ag | Procedimiento para la obtencion de n-arilsulfonilpirroles. |
| DE102005002130A1 (de) * | 2005-01-17 | 2006-07-27 | Sanofi-Aventis Deutschland Gmbh | Substituierte N-Aminomethylensulfonamide, ihre Herstellung und Verwendung als Arzneimittel |
| CN116041228B (zh) * | 2022-05-16 | 2024-03-12 | 沈阳希贝康医药科技有限公司 | 一种布美他尼的合成方法 |
-
1975
- 1975-04-29 DE DE19752518999 patent/DE2518999A1/de not_active Withdrawn
-
1976
- 1976-04-23 NL NL7604356A patent/NL7604356A/xx not_active Application Discontinuation
- 1976-04-27 FI FI761156A patent/FI761156A7/fi not_active Application Discontinuation
- 1976-04-28 HU HU76HO00001899A patent/HU172482B/hu unknown
- 1976-04-28 CA CA251,343A patent/CA1082191A/en not_active Expired
- 1976-04-28 JP JP51049307A patent/JPS51131849A/ja active Pending
- 1976-04-28 NO NO761468A patent/NO143154C/no unknown
- 1976-04-28 AT AT309976A patent/AT345268B/de not_active IP Right Cessation
- 1976-04-28 DK DK189876A patent/DK189876A/da not_active Application Discontinuation
- 1976-04-29 SE SE7604940A patent/SE7604940L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51131849A (en) | 1976-11-16 |
| DE2518999A1 (de) | 1976-11-18 |
| ATA309976A (de) | 1978-01-15 |
| HU172482B (hu) | 1978-09-28 |
| DK189876A (da) | 1976-10-30 |
| NO143154C (no) | 1980-12-29 |
| FI761156A7 (enrdf_load_html_response) | 1976-10-30 |
| NO761468L (enrdf_load_html_response) | 1976-11-01 |
| AT345268B (de) | 1978-09-11 |
| NO143154B (no) | 1980-09-15 |
| SE7604940L (sv) | 1976-10-30 |
| NL7604356A (nl) | 1976-11-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |