CH625217A5 - - Google Patents

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Info

Publication number: CH625217A5
Authority: CH; Switzerland
Prior art keywords: pyrrolyl; formula; salt; sulfamoyl; benzoic acid
Prior art date: 1976-12-24

Application number

CH880680A

Other languages

German (de)

English (en)

Inventor

Ernst Dr Habicht

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.)

1976-12-24

Filing date

1980-11-27

Publication date

1981-09-15

1980-11-27 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1981-09-15 Publication of CH625217A5 publication Critical patent/CH625217A5/de

Links

WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 18
-1 1-pyrrolyl radical Chemical class 0.000 claims description 17
239000005711 Benzoic acid Substances 0.000 claims description 15
235000010233 benzoic acid Nutrition 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
238000000034 method Methods 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
150000002431 hydrogen Chemical group 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
229910052717 sulfur Chemical group 0.000 claims description 4
239000011593 sulfur Chemical group 0.000 claims description 4
241000251730 Chondrichthyes Species 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
150000005840 aryl radicals Chemical class 0.000 claims description 3
239000003446 ligand Substances 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
125000005059 halophenyl group Chemical group 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
102100033479 RAF proto-oncogene serine/threonine-protein kinase Human genes 0.000 claims 1
101710141955 RAF proto-oncogene serine/threonine-protein kinase Proteins 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000000047 product Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
XPWNKJUPBKTKSI-UHFFFAOYSA-N 3-amino-4-chloro-5-sulfamoylbenzoic acid Chemical compound NC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1Cl XPWNKJUPBKTKSI-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000003792 electrolyte Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000155 melt Substances 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 1
AIBXPICJORBEKA-UHFFFAOYSA-N 3-amino-4-bromo-5-sulfamoylbenzoic acid Chemical compound S(N)(=O)(=O)C=1C=C(C(=O)O)C=C(C=1Br)N AIBXPICJORBEKA-UHFFFAOYSA-N 0.000 description 1
UPSPCBVICASHAW-UHFFFAOYSA-N 4-phenoxy-3-pyrrol-1-yl-5-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=CC(N2C=CC=C2)=C1OC1=CC=CC=C1 UPSPCBVICASHAW-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
208000004880 Polyuria Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
VRMWOQSSFPYAQD-UHFFFAOYSA-N [K].NC(N)=O Chemical compound [K].NC(N)=O VRMWOQSSFPYAQD-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000012445 acidic reagent Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000004849 alkoxymethyl group Chemical group 0.000 description 1
125000005036 alkoxyphenyl group Chemical group 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940127088 antihypertensive drug Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
229960002896 clonidine Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
VQKLRVZQQYVIJW-UHFFFAOYSA-N dihydralazine Chemical compound C1=CC=C2C(NN)=NN=C(NN)C2=C1 VQKLRVZQQYVIJW-UHFFFAOYSA-N 0.000 description 1
229960002877 dihydralazine Drugs 0.000 description 1
230000035619 diuresis Effects 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 1
229960003602 guanethidine Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
206010038464 renal hypertension Diseases 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
230000000894 saliuretic effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 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
241000894007 species Species 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrrole Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH880680A 1976-12-24 1980-11-27 CH625217A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1630976A CH628622A5 (de)	1976-12-24	1976-12-24	Verfahren zur herstellung von neuen in 4-stellung substituierten 3-sulfamoylbenzoesaeuren.

Publications (1)

Publication Number	Publication Date
CH625217A5 true CH625217A5 (fr)	1981-09-15

Family

ID=4416194

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
CH1630976A CH628622A5 (de)	1976-12-24	1976-12-24	Verfahren zur herstellung von neuen in 4-stellung substituierten 3-sulfamoylbenzoesaeuren.
CH880580A CH625216A5 (fr)	1976-12-24	1980-11-27
CH880680A CH625217A5 (fr)	1976-12-24	1980-11-27
CH880480A CH625215A5 (fr)	1976-12-24	1980-11-27

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
CH1630976A CH628622A5 (de)	1976-12-24	1976-12-24	Verfahren zur herstellung von neuen in 4-stellung substituierten 3-sulfamoylbenzoesaeuren.
CH880580A CH625216A5 (fr)	1976-12-24	1980-11-27

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH880480A CH625215A5 (fr)	1976-12-24	1980-11-27

Country Status (23)

Country	Link
US (1)	US4176190A (fr)
JP (1)	JPS5379858A (fr)
AT (1)	AT362350B (fr)
AU (1)	AU515286B2 (fr)
BE (1)	BE862275A (fr)
CA (1)	CA1083160A (fr)
CH (4)	CH628622A5 (fr)
DD (1)	DD134641A5 (fr)
DE (1)	DE2756783A1 (fr)
DK (1)	DK575177A (fr)
ES (1)	ES465390A1 (fr)
FI (1)	FI773846A (fr)
FR (1)	FR2375211A1 (fr)
GB (1)	GB1592295A (fr)
HU (1)	HU177298B (fr)
IE (1)	IE46279B1 (fr)
IT (1)	IT1092247B (fr)
NL (1)	NL7713916A (fr)
NO (1)	NO774451L (fr)
NZ (1)	NZ186059A (fr)
PL (3)	PL110872B1 (fr)
SE (1)	SE7714656L (fr)
ZA (1)	ZA777629B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES465207A1 (es) *	1976-12-24	1978-11-16	Hoechst Ag	Procedimiento para la preparacion de derivados de acidos pi-rrolo-benzoicos.
DE2737195A1 (de) *	1977-08-18	1979-03-01	Hoechst Ag	Benzolsulfonamidderivate und verfahren zu ihrer herstellung
DE2966048D1 (en) *	1978-07-20	1983-09-15	Basf Ag	N-arylsulfonyl pyrroles, their preparation and medicaments containing them
DE2917997A1 (de) *	1979-05-04	1980-11-20	Hoechst Ag	Substituierte pyrrolidinyl-benzoesaeure- derivate und verfahren zu ihrer herstellung
CA1341128C (fr)	1989-06-27	2000-10-24	Borden Chemical, Inc.	Matrice de fibres optiques
US5908858A (en)	1996-04-05	1999-06-01	Sankyo Company, Limited	1,2-diphenylpyrrole derivatives, their preparation and their therapeutic uses
JP2010533205A (ja)	2007-07-12	2010-10-21	トラガラファーマシューティカルズ，インク．	癌、腫瘍、および腫瘍関連障害を治療するための方法および組成物

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3565920A (en) *	1966-12-29	1971-02-23	Ciba Geigy Corp	5-sulfamyl-anthranilic acids
US3534027A (en) *	1968-04-25	1970-10-13	Hoffmann La Roche	Pyrrolyl ethylamino sulfamoyl benzoic acids,esters and salts thereof
US3939267A (en) *	1972-10-13	1976-02-17	Ciba-Geigy Corporation	4-Ethers of 3-amino-5-sulfamoylbenzoic acids
DE2419970C3 (de) *	1974-04-25	1980-06-12	Hoechst Ag, 6000 Frankfurt	3-<l-Pyrrolidinyl)-4-phenoxy-5sulfamoylbenzoesäure und Verfahren zu ihrer Herstellung
US4093735A (en) *	1974-04-25	1978-06-06	Hoechst Aktiengesellschaft	5-Sulfamoylbenzoic acid derivatives carrying a heterocyclic substituent
GB1523631A (en) *	1975-07-08	1978-09-06	Leo Pharm Prod Ltd	Sulphonamide derivatives

1976
- 1976-12-24 CH CH1630976A patent/CH628622A5/de not_active IP Right Cessation
1977
- 1977-12-14 US US05/860,533 patent/US4176190A/en not_active Expired - Lifetime
- 1977-12-15 GB GB52249/77A patent/GB1592295A/en not_active Expired
- 1977-12-15 NL NL7713916A patent/NL7713916A/xx not_active Application Discontinuation
- 1977-12-19 FI FI773846A patent/FI773846A/fi not_active Application Discontinuation
- 1977-12-20 DE DE19772756783 patent/DE2756783A1/de not_active Withdrawn
- 1977-12-21 NZ NZ186059A patent/NZ186059A/xx unknown
- 1977-12-22 DD DD77202894A patent/DD134641A5/xx unknown
- 1977-12-22 DK DK575177A patent/DK575177A/da unknown
- 1977-12-22 HU HU77CI1789A patent/HU177298B/hu unknown
- 1977-12-22 AU AU31864/77A patent/AU515286B2/en not_active Expired
- 1977-12-22 PL PL1977203248A patent/PL110872B1/pl unknown
- 1977-12-22 IE IE2608/77A patent/IE46279B1/en unknown
- 1977-12-22 SE SE7714656A patent/SE7714656L/xx not_active Application Discontinuation
- 1977-12-22 FR FR7738857A patent/FR2375211A1/fr active Granted
- 1977-12-22 PL PL1977211757A patent/PL112696B1/pl unknown
- 1977-12-22 CA CA293,789A patent/CA1083160A/fr not_active Expired
- 1977-12-22 ZA ZA00777629A patent/ZA777629B/xx unknown
- 1977-12-22 PL PL1977211756A patent/PL110887B1/pl unknown
- 1977-12-22 IT IT52333/77A patent/IT1092247B/it active
- 1977-12-23 AT AT928177A patent/AT362350B/de not_active IP Right Cessation
- 1977-12-23 ES ES465390A patent/ES465390A1/es not_active Expired
- 1977-12-23 NO NO774451A patent/NO774451L/no unknown
- 1977-12-23 BE BE183803A patent/BE862275A/fr unknown
- 1977-12-24 JP JP15510677A patent/JPS5379858A/ja active Pending
1980
- 1980-11-27 CH CH880580A patent/CH625216A5/de not_active IP Right Cessation
- 1980-11-27 CH CH880680A patent/CH625217A5/de not_active IP Right Cessation
- 1980-11-27 CH CH880480A patent/CH625215A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ES465390A1 (es)	1978-09-16
CA1083160A (fr)	1980-08-05
BE862275A (fr)	1978-06-23
PL203248A1 (pl)	1978-12-04
NZ186059A (en)	1979-11-01
FI773846A (fi)	1978-06-25
PL112696B1 (en)	1980-10-31
GB1592295A (en)	1981-07-01
JPS5379858A (en)	1978-07-14
AT362350B (de)	1981-05-11
AU3186477A (en)	1979-06-28
US4176190A (en)	1979-11-27
FR2375211A1 (fr)	1978-07-21
IT1092247B (it)	1985-07-06
HU177298B (en)	1981-09-28
NO774451L (no)	1978-06-27
FR2375211B1 (fr)	1981-07-17
PL110872B1 (en)	1980-08-30
DE2756783A1 (de)	1978-06-29
IE46279L (en)	1978-06-24
CH628622A5 (de)	1982-03-15
NL7713916A (nl)	1978-06-27
CH625215A5 (fr)	1981-09-15
AU515286B2 (en)	1981-03-26
DD134641A5 (de)	1979-03-14
PL110887B1 (en)	1980-08-30
ZA777629B (en)	1978-10-25
SE7714656L (sv)	1978-06-25
CH625216A5 (fr)	1981-09-15
DK575177A (da)	1978-06-25
IE46279B1 (en)	1983-04-20
ATA928177A (de)	1980-10-15

Publication	Publication Date	Title
AT363096B (de)	1981-07-10	Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen
DE1668648C3 (de)	1974-02-21	3-Benzoylphenylessigsäurederivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2461861A1 (de)	1975-08-07	8-hydroxycarbostyril-derivate, verfahren zu ihrer herstellung und arzneimittel
DE3026201C2 (fr)	1990-11-08
DE2901181A1 (de)	1979-07-26	2-methoxy-4-amino-5-alkylsulfonylbenzamide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
CH381706A (de)	1964-09-15	Verfahren zur Herstellung von Sulfamylanthranilsäuren
DE2205815A1 (de)	1973-08-16	Piperazinderivate und verfahren zu ihrer herstellung
EP0000220A1 (fr)	1979-01-10	Dihydrouraciles, procédé pour leur préparation et médicaments les contenant
EP0105210B1 (fr)	1987-03-04	Dérivés de l'isoquinoléine, leur procédé de préparation compositions pharmaceutiques les contenant et leur utilisation
CH625217A5 (fr)	1981-09-15
DE2461802A1 (de)	1975-07-17	Pyrazinderivate
DE3216843C2 (de)	1986-10-23	3-Thiomethyl-pyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
US3479346A (en)	1969-11-18	N-acyl-n- (and n,n-bis-) ((1-piperidyl)-lower-alkyl)amines
DD145104B3 (de)	1990-07-18	Verfahren zur herstellung von polyalkoxyphenylpyrrolidone
AT372955B (de)	1983-12-12	Verfahren zur herstellung neuer benzopyranderivate
EP0018360B1 (fr)	1981-09-30	N-(5-méthoxybenzofuran-2-ylcarbonyl)-N'-benzylpipérazine et procédé pour sa préparation
DE1593728C3 (de)	1980-02-14	Substituierte Amidine und Verfahren zu ihrer Herstellung
DD151408A5 (de)	1981-10-21	Verfahren zur herstellung neuer pharmazeutisch aktiver phenylpiperazinderivate
DE3023717C2 (fr)	1991-03-21
DE3424586A1 (de)	1986-01-09	3-aminocarbonylmethoxy-5-phenyl-pyrazol-verbindungen sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0124630B1 (fr)	1987-01-28	Dérivés de pyrimidinothioalkyle pyridine, procédé pour leur préparation et médicaments contenant ces composés
AT391316B (de)	1990-09-25	Neue thienyloxy-alkylamin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CH616934A5 (en)	1980-04-30	Process for the preparation of chromone derivatives
DE1076691B (de)	1960-03-03	Verfahren zur Herstellung von Phenthiazinderivaten
CH637957A5 (de)	1983-08-31	Verfahren zur herstellung neuer pyridobenzodiazepinone und ihrer salze.

Legal Events

Date	Code	Title	Description
1983-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased