CH504416A - Verfahren zur Herstellung von aromatischen Sulfamoylverbindungen - Google Patents

Verfahren zur Herstellung von aromatischen Sulfamoylverbindungen

Info

Publication number: CH504416A
Authority: CH; Switzerland
Prior art keywords: group; acid; radical; phenyl; alkyl
Prior art date: 1966-12-05

Application number

CH1621767A

Other languages

German (de)

English (en)

Inventor

Harvey Werner Lincoln

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1966-12-05

Filing date

1967-11-20

Publication date

1971-03-15

1967-11-20 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1967-11-20 Priority to CH1941069A priority Critical patent/CH504417A/de

1967-11-20 Priority to CH1940969A priority patent/CH529114A/de

1971-03-15 Publication of CH504416A publication Critical patent/CH504416A/de

Links

125000000217 alkyl group Chemical group 0.000 abstract description 49
125000003118 aryl group Chemical group 0.000 abstract description 23
125000001931 aliphatic group Chemical group 0.000 abstract description 22
150000003839 salts Chemical class 0.000 abstract description 21
125000002252 acyl group Chemical group 0.000 abstract description 10
125000003342 alkenyl group Chemical group 0.000 abstract description 9
239000002934 diuretic Substances 0.000 abstract description 9
150000002148 esters Chemical class 0.000 abstract description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 6
125000000392 cycloalkenyl group Chemical group 0.000 abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 abstract description 5
229910052801 chlorine Inorganic materials 0.000 abstract description 3
125000002947 alkylene group Chemical group 0.000 abstract description 2
125000000304 alkynyl group Chemical group 0.000 abstract description 2
229910052794 bromium Inorganic materials 0.000 abstract description 2
125000001072 heteroaryl group Chemical group 0.000 abstract 2
230000003216 chloruretic effect Effects 0.000 abstract 1
229940030606 diuretics Drugs 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 118
-1 aliphatic radical Chemical class 0.000 description 110
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 81
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
150000003254 radicals Chemical class 0.000 description 39
239000000243 solution Substances 0.000 description 38
239000002244 precipitate Substances 0.000 description 37
239000000203 mixture Substances 0.000 description 35
150000001875 compounds Chemical class 0.000 description 33
239000002253 acid Substances 0.000 description 30
239000000155 melt Substances 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
239000007858 starting material Substances 0.000 description 22
125000004432 carbon atom Chemical group C* 0.000 description 18
238000001953 recrystallisation Methods 0.000 description 17
229910052757 nitrogen Inorganic materials 0.000 description 14
238000001816 cooling Methods 0.000 description 13
239000012299 nitrogen atmosphere Substances 0.000 description 13
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 12
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
125000002950 monocyclic group Chemical group 0.000 description 11
125000005842 heteroatom Chemical group 0.000 description 10
238000000034 method Methods 0.000 description 10
150000007513 acids Chemical class 0.000 description 9
125000000623 heterocyclic group Chemical group 0.000 description 9
238000003756 stirring Methods 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
239000005711 Benzoic acid Substances 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
239000010410 layer Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
125000002619 bicyclic group Chemical group 0.000 description 6
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 6
230000000144 pharmacologic effect Effects 0.000 description 6
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
MPUNAIYDVXJQBJ-UHFFFAOYSA-N 2,4-dichloro-5-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC(S(Cl)(=O)=O)=C(Cl)C=C1Cl MPUNAIYDVXJQBJ-UHFFFAOYSA-N 0.000 description 5
KYLIGGHDGPWRPT-UHFFFAOYSA-N 4-chloro-2-[furan-2-ylmethyl(sulfamoyl)amino]-5-phenylbenzoic acid Chemical compound ClC=1C=C(C(C(=O)O)=CC1C1=CC=CC=C1)N(CC1=CC=CO1)S(N)(=O)=O KYLIGGHDGPWRPT-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000004414 alkyl thio group Chemical group 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
230000001882 diuretic effect Effects 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
230000001452 natriuretic effect Effects 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
238000012360 testing method Methods 0.000 description 4
125000003396 thiol group Chemical group [H]S* 0.000 description 4
ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4 dichlorobenzoic acid Natural products OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
150000001342 alkaline earth metals Chemical class 0.000 description 3
125000003282 alkyl amino group Chemical group 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
229940099112 cornstarch Drugs 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000007788 liquid Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
KTWCBPNVALETHA-UHFFFAOYSA-N 2,4-dichloro-5-(phenylsulfamoyl)benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(S(=O)(=O)NC=2C=CC=CC=2)=C1Cl KTWCBPNVALETHA-UHFFFAOYSA-N 0.000 description 2
HOFZUHZPCFZJAA-UHFFFAOYSA-N 2,4-dichloro-5-[(4-methylphenyl)sulfamoyl]benzoic acid Chemical compound ClC1=C(C(=O)O)C=C(C(=C1)Cl)S(NC1=CC=C(C=C1)C)(=O)=O HOFZUHZPCFZJAA-UHFFFAOYSA-N 0.000 description 2
JNCRMCPXCYMPHV-UHFFFAOYSA-N 2,4-dichloro-5-[methyl(phenyl)sulfamoyl]benzoic acid Chemical compound ClC1=C(C(=O)O)C=C(C(=C1)Cl)S(N(C1=CC=CC=C1)C)(=O)=O JNCRMCPXCYMPHV-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
VLWLOYMYJPTGLS-UHFFFAOYSA-N 4-chloro-2-(furan-2-ylmethylamino)-5-[(4-methoxyphenyl)sulfamoyl]benzoic acid Chemical compound C(C1=CC=CO1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NC1=CC=C(C=C1)OC)(=O)=O VLWLOYMYJPTGLS-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
NFNJUJDXCXINGF-UHFFFAOYSA-N Cl.ClC1=C(C(=O)O)C=C(C(=C1)Cl)S(NC1=CC=C(C=C1)N)(=O)=O Chemical compound Cl.ClC1=C(C(=O)O)C=C(C(=C1)Cl)S(NC1=CC=C(C=C1)N)(=O)=O NFNJUJDXCXINGF-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229930016911 cinnamic acid Natural products 0.000 description 2
235000013985 cinnamic acid Nutrition 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000284 extract Substances 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
239000008101 lactose Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
150000002829 nitrogen Chemical class 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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 2
239000002994 raw material Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
125000001302 tertiary amino group Chemical group 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
QAOJBHRZQQDFHA-UHFFFAOYSA-N 2,3-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1Cl QAOJBHRZQQDFHA-UHFFFAOYSA-N 0.000 description 1
HCAUYQLDJTWXAV-UHFFFAOYSA-N 2,4-dichloro-5-[(2-chlorophenyl)sulfamoyl]benzoic acid Chemical compound OC(=O)C1=C(Cl)C=C(Cl)C(=C1)S(=O)(=O)NC1=C(Cl)C=CC=C1 HCAUYQLDJTWXAV-UHFFFAOYSA-N 0.000 description 1
OTSLSIROCRGQKW-UHFFFAOYSA-N 2,4-dichloro-5-[(3-chlorophenyl)sulfamoyl]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(S(=O)(=O)NC=2C=C(Cl)C=CC=2)=C1Cl OTSLSIROCRGQKW-UHFFFAOYSA-N 0.000 description 1
DLTMPHWJUYBJGY-UHFFFAOYSA-N 2,4-dichloro-5-[(4-fluorophenyl)sulfamoyl]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(S(=O)(=O)NC=2C=CC(F)=CC=2)=C1Cl DLTMPHWJUYBJGY-UHFFFAOYSA-N 0.000 description 1
NRPBJEMEHKHKFB-UHFFFAOYSA-N 2,4-dichloro-5-[(4-methoxyphenyl)sulfamoyl]benzoic acid Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC(C(O)=O)=C(Cl)C=C1Cl NRPBJEMEHKHKFB-UHFFFAOYSA-N 0.000 description 1
UUDUWVNKUYFIRG-UHFFFAOYSA-N 2,4-dichloro-5-[(4-nitrophenyl)sulfamoyl]benzoic acid Chemical compound ClC1=C(C(=O)O)C=C(C(=C1)Cl)S(NC1=CC=C(C=C1)[N+](=O)[O-])(=O)=O UUDUWVNKUYFIRG-UHFFFAOYSA-N 0.000 description 1
ZJLFNHRJVKMUGJ-UHFFFAOYSA-N 2,4-dichloro-5-phenyl-3-sulfamoylbenzoic acid Chemical compound ClC1=C(C(=O)O)C=C(C(=C1S(N)(=O)=O)Cl)C1=CC=CC=C1 ZJLFNHRJVKMUGJ-UHFFFAOYSA-N 0.000 description 1
ATHAVGGRIPQSCR-UHFFFAOYSA-N 2,4-dichloro-n-phenyl-5-(phenylsulfamoyl)benzamide Chemical compound ClC1=CC(Cl)=C(S(=O)(=O)NC=2C=CC=CC=2)C=C1C(=O)NC1=CC=CC=C1 ATHAVGGRIPQSCR-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
VASMTGOLJFHPPK-UHFFFAOYSA-N 2-(benzylamino)-4-chloro-5-(phenylsulfamoyl)benzoic acid Chemical compound C(C1=CC=CC=C1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NC1=CC=CC=C1)(=O)=O VASMTGOLJFHPPK-UHFFFAOYSA-N 0.000 description 1
NOKJDOXMDYTQEZ-UHFFFAOYSA-N 2-[acetyl(benzyl)amino]-5-[acetyl(phenyl)sulfamoyl]-4-chlorobenzoic acid Chemical compound C(C)(=O)N(C=1C(C(=O)O)=CC(=C(C1)Cl)S(N(C1=CC=CC=C1)C(C)=O)(=O)=O)CC1=CC=CC=C1 NOKJDOXMDYTQEZ-UHFFFAOYSA-N 0.000 description 1
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/42—Halides thereof

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1621767A 1966-12-05 1967-11-20 Verfahren zur Herstellung von aromatischen Sulfamoylverbindungen CH504416A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH1941069A CH504417A (de)	1966-12-05	1967-11-20	Verfahren zur Herstellung von aromatischen Sulfamoylverbindungen
CH1940969A CH529114A (de)	1967-10-16	1967-11-20	Verfahren zur Herstellung von aromatischen Sulfamoylverbindungen

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US59898066A	1966-12-05	1966-12-05
US67533067A	1967-10-16	1967-10-16
DEF0054085		1967-11-21

Publications (1)

Publication Number	Publication Date
CH504416A true CH504416A (de)	1971-03-15

Family

ID=27210549

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1621767A CH504416A (de)	1966-12-05	1967-11-20	Verfahren zur Herstellung von aromatischen Sulfamoylverbindungen

Country Status (7)

Country	Link
AT (1)	AT290499B (fr)
BE (1)	BE707524A (fr)
CH (1)	CH504416A (fr)
DE (1)	DE1643279A1 (fr)
FR (3)	FR1575550A (fr)
GB (2)	GB1189719A (fr)
NL (1)	NL6716492A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2002072538A1 (fr) *	2001-03-14	2002-09-19	Aventis Pharma Deutschland Gmbh	Procede ameliore de production de derives de sulfonylcarboxamides

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6284923B1 (en) *	1997-08-22	2001-09-04	Tularik Inc	Substituted benzene compounds as antiproliferative and cholesterol lowering action
EP1090014B1 (fr)	1998-06-25	2003-09-03	Tularik Inc.	Phosphates d'arylsulfonanilide
US6153585A (en)	1998-07-20	2000-11-28	Tularik Inc.	Arylsulfonanilide derivatives
KR100642184B1 (ko)	1998-09-23	2006-11-10	암젠 인크	아릴술폰아닐리드 우레아
GB9824579D0 (en) *	1998-11-10	1999-01-06	Novartis Ag	Organic compounds
US6822001B2 (en)	2000-11-03	2004-11-23	Tularik Inc.	Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents
US20060281788A1 (en)	2005-06-10	2006-12-14	Baumann Christian A	Synergistic modulation of flt3 kinase using a flt3 inhibitor and a farnesyl transferase inhibitor
EP2016070B1 (fr)	2006-04-20	2016-01-13	Janssen Pharmaceutica N.V.	Inhibiteurs de la c-fms kinase
US8697716B2 (en)	2006-04-20	2014-04-15	Janssen Pharmaceutica Nv	Method of inhibiting C-KIT kinase
MX2008013533A (es)	2006-04-20	2009-01-15	Janssen Pharmaceutica Nv	Compuestos heterociclicos como inhibidores de c-fms cinasa.
JO3240B1 (ar)	2007-10-17	2018-03-08	Janssen Pharmaceutica Nv	c-fms مثبطات كيناز
CN107266405A (zh)	2012-08-07	2017-10-20	詹森药业有限公司	用于制备c‑fms激酶抑制剂的方法
CN104870454B (zh)	2012-08-07	2020-03-03	詹森药业有限公司	用于制备杂环酯衍生物的方法

1967
- 1967-11-20 CH CH1621767A patent/CH504416A/de not_active IP Right Cessation
- 1967-11-28 GB GB5408567D patent/GB1189719A/en not_active Expired
- 1967-11-28 GB GB3017469A patent/GB1189720A/en not_active Expired
- 1967-11-30 DE DE19671643279 patent/DE1643279A1/de active Pending
- 1967-12-04 BE BE707524D patent/BE707524A/xx unknown
- 1967-12-04 AT AT1095767A patent/AT290499B/de not_active IP Right Cessation
- 1967-12-04 FR FR1575550D patent/FR1575550A/fr not_active Expired
- 1967-12-04 NL NL6716492A patent/NL6716492A/xx unknown
1968
- 1968-02-29 FR FR141758A patent/FR7838M/fr not_active Expired
- 1968-02-29 FR FR141757A patent/FR7837M/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2002072538A1 (fr) *	2001-03-14	2002-09-19	Aventis Pharma Deutschland Gmbh	Procede ameliore de production de derives de sulfonylcarboxamides

Also Published As

Publication number	Publication date
FR7837M (fr)	1970-05-25
GB1189719A (en)	1970-04-29
FR7838M (fr)	1970-05-25
GB1189720A (en)	1970-04-29
AT290499B (de)	1971-06-11
DE1643279A1 (de)	1971-06-09
NL6716492A (fr)	1968-06-06
FR1575550A (fr)	1969-07-25
BE707524A (fr)	1968-06-04

Legal Events

Date	Code	Title	Description
1976-06-30	PL	Patent ceased

Publication	Publication Date	Title
DE3885889T2 (de)	1994-04-07	(r)5-pentylamino-5-oxopentanesäure-derivate mit anticholecystokininwirkung.
CH619209A5 (fr)	1980-09-15
DE2706977A1 (de)	1978-08-24	Benzoesaeuren und deren derivate sowie verfahren zu ihrer herstellung
DE1795699C3 (fr)	1975-12-18
DE1643279A1 (de)	1971-06-09	Aromatische Sulfamoylverbindungen
DE2941869C2 (fr)	1988-07-21
DD149217A5 (de)	1981-07-01	Verfahren zur herstellung von pyrimidonderivaten
DE1620442C3 (de)	1975-07-03	Verfahren zur Herstellung von 1-Acylindolverbindungen
DE2437487A1 (de)	1976-02-19	7-methoxy-6-thia-tetracycline und verfahren zu ihrer herstellung
EP0005559B1 (fr)	1981-11-04	Dérivés d'acide phénylaminothiophène-acétique, procédé pour leur préparation et médicaments les contenant
DE2321518C2 (de)	1986-07-31	Sulfamylbenzoesäuren und deren Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Mittel
EP0103142B1 (fr)	1987-04-22	Dérivés de thiéno(2,3-e)-1,2-thiazine
DE69102069T2 (de)	1994-09-01	5-aminosalicylsäurederivate zur therapie chronisch entzündlicher baucherkrankungen.
DE2021105A1 (de)	1970-11-05	Neue Sulfamylanthranilsaeuren
DE1919381B2 (de)	1974-05-16	Heterocyclische Verbindungen und Verfahren zu deren Herstellung
DE2526795A1 (de)	1976-01-08	Sulfonamide
CH644861A5 (en)	1984-08-31	Process for the preparation of 5-(2-furoyl)-, 5-(2-thenoyl)-, 5-(3-furoyl)- and 5-(3-thenoyl)-1,2-dihydro-3H-pyrrolo-[1,2-a]pyrrole-1-carboxylic acid derivatives
DE2054142A1 (de)	1971-06-03	Pyridinsulfonsauren
DE2734270C2 (fr)	1990-06-21
DE1493513C3 (de)	1975-09-11	Sulfamylanthranilsäuren, deren therapeutisch verwendbare Salze, Verfahren zu ihrer Herstellung und diese enthaltenden pharmazeutischen Präparate
CH529114A (de)	1972-10-15	Verfahren zur Herstellung von aromatischen Sulfamoylverbindungen
DE2434506A1 (de)	1975-02-13	Verfahren zur herstellung von neuen derivaten des imidazolidins
CH504417A (de)	1971-03-15	Verfahren zur Herstellung von aromatischen Sulfamoylverbindungen
DE2029991C3 (de)	1978-08-24	2-Hydroxy-5-aminobenzamide, Verfahren zu ihrer Herstellung und Arzneimittel, die diese Verbindungen enthalten
DE2319280A1 (de)	1974-11-07	1-substituierte pyrazolone-(5), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel

CH504416A - Verfahren zur Herstellung von aromatischen Sulfamoylverbindungen - Google Patents

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Priority Applications (2)

Applications Claiming Priority (3)

Publications (1)

Family

ID=27210549

Family Applications (1)

Country Status (7)

Cited By (1)

Families Citing this family (13)

Cited By (1)

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