NO774455L - Fremgangsmaate til fremstilling av pyrrolo-benzosyre-derivater - Google Patents
Fremgangsmaate til fremstilling av pyrrolo-benzosyre-derivaterInfo
- Publication number
- NO774455L NO774455L NO774455A NO774455A NO774455L NO 774455 L NO774455 L NO 774455L NO 774455 A NO774455 A NO 774455A NO 774455 A NO774455 A NO 774455A NO 774455 L NO774455 L NO 774455L
- Authority
- NO
- Norway
- Prior art keywords
- benzoic acid
- methyl ester
- acid methyl
- atoms
- alkyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 18
- -1 3,4-methylenedioxy group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 230000000054 salidiuretic effect Effects 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 239000000969 carrier Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
- 239000000047 product Substances 0.000 description 29
- 239000013078 crystal Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- 239000005457 ice water Substances 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 17
- 239000012362 glacial acetic acid Substances 0.000 description 17
- 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 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000004702 methyl esters Chemical class 0.000 description 11
- 229910001868 water Inorganic materials 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000007868 Raney catalyst Substances 0.000 description 10
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 10
- 229910000564 Raney nickel Inorganic materials 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 7
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000002828 nitro derivatives Chemical class 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000000565 sulfonamide group Chemical group 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- UJEWTUDSLQGTOA-UHFFFAOYSA-N Piretanide Chemical compound C=1C=CC=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1N1CCCC1 UJEWTUDSLQGTOA-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KDNIOKSLVIGAAN-UHFFFAOYSA-N 2-sulfamoylbenzoic acid Chemical class NS(=O)(=O)C1=CC=CC=C1C(O)=O KDNIOKSLVIGAAN-UHFFFAOYSA-N 0.000 description 1
- ASNXJGMTRPTJON-UHFFFAOYSA-N 4-(4-methylanilino)-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid Chemical compound C1=CC(C)=CC=C1NC1=C(N2CCCC2)C=C(C(O)=O)C=C1S(N)(=O)=O ASNXJGMTRPTJON-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229960002576 amiloride Drugs 0.000 description 1
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OFOQZXQXWSOPSZ-UHFFFAOYSA-N methyl 4-chloro-2-(dimethylamino)-5-(methylideneamino)sulfonyl-3-nitrobenzoate Chemical compound COC(C1=C(C(=C(C(=C1)S(=O)(=O)N=C)Cl)[N+](=O)[O-])N(C)C)=O OFOQZXQXWSOPSZ-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
- 210000003205 muscle Anatomy 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- XCWZSWBOSVVZGV-UHFFFAOYSA-N oxolane-2,5-diol Chemical class OC1CCC(O)O1 XCWZSWBOSVVZGV-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- RRAHCFJFWDVGGZ-UHFFFAOYSA-M potassium;4-methylphenolate Chemical compound [K+].CC1=CC=C([O-])C=C1 RRAHCFJFWDVGGZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- LEWPSSCATGWXEP-UHFFFAOYSA-M sodium;1,3-benzodioxol-5-olate Chemical compound [Na+].[O-]C1=CC=C2OCOC2=C1 LEWPSSCATGWXEP-UHFFFAOYSA-M 0.000 description 1
- IIHZUISTNNNXQQ-UHFFFAOYSA-M sodium;3-methoxyphenolate Chemical compound [Na+].COC1=CC=CC([O-])=C1 IIHZUISTNNNXQQ-UHFFFAOYSA-M 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
- MYMOTVMHKLYQCM-UHFFFAOYSA-M sodium;4-methoxyphenolate Chemical compound [Na+].COC1=CC=C([O-])C=C1 MYMOTVMHKLYQCM-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
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2658766A DE2658766C2 (de) | 1976-12-24 | 1976-12-24 | 3-N-Pyrrolo-5-sulfamoylbenzoesäure-Derivate und Verfahren zu ihrer Herstellung |
| DE19772718494 DE2718494A1 (de) | 1977-04-26 | 1977-04-26 | Verfahren zur herstellung von pyrrolo-benzoesaeure-derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO774455L true NO774455L (no) | 1978-06-27 |
Family
ID=25771305
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO774455A NO774455L (no) | 1976-12-24 | 1977-12-23 | Fremgangsmaate til fremstilling av pyrrolo-benzosyre-derivater |
| NO821761A NO821761L (no) | 1976-12-24 | 1982-05-27 | Pyrrolo-benzosyrederivater |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO821761A NO821761L (no) | 1976-12-24 | 1982-05-27 | Pyrrolo-benzosyrederivater |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4172142A (sv) |
| JP (1) | JPS5379859A (sv) |
| AT (1) | AT371806B (sv) |
| AU (1) | AU516399B2 (sv) |
| CA (1) | CA1093565A (sv) |
| CH (1) | CH632996A5 (sv) |
| DK (1) | DK162088C (sv) |
| ES (1) | ES465207A1 (sv) |
| FI (1) | FI773906A (sv) |
| FR (2) | FR2375210A1 (sv) |
| GB (2) | GB1589339A (sv) |
| GR (1) | GR71189B (sv) |
| HU (1) | HU177641B (sv) |
| IE (1) | IE46126B1 (sv) |
| IL (1) | IL53673A (sv) |
| IT (1) | IT1089319B (sv) |
| NL (1) | NL7714062A (sv) |
| NO (2) | NO774455L (sv) |
| NZ (1) | NZ186094A (sv) |
| PH (1) | PH14409A (sv) |
| PT (1) | PT67449B (sv) |
| SE (2) | SE425487B (sv) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2917997A1 (de) * | 1979-05-04 | 1980-11-20 | Hoechst Ag | Substituierte pyrrolidinyl-benzoesaeure- derivate und verfahren zu ihrer herstellung |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2419970C3 (de) * | 1974-04-25 | 1980-06-12 | Hoechst Ag, 6000 Frankfurt | 3-<l-Pyrrolidinyl)-4-phenoxy-5sulfamoylbenzoesäure und Verfahren zu ihrer Herstellung |
| CH628622A5 (de) * | 1976-12-24 | 1982-03-15 | Ciba Geigy Ag | Verfahren zur herstellung von neuen in 4-stellung substituierten 3-sulfamoylbenzoesaeuren. |
-
1977
- 1977-12-19 NL NL7714062A patent/NL7714062A/xx not_active Application Discontinuation
- 1977-12-19 ES ES465207A patent/ES465207A1/es not_active Expired
- 1977-12-20 FR FR7738494A patent/FR2375210A1/fr active Granted
- 1977-12-21 CH CH1580477A patent/CH632996A5/de not_active IP Right Cessation
- 1977-12-21 US US05/862,669 patent/US4172142A/en not_active Expired - Lifetime
- 1977-12-21 HU HU77HO2036A patent/HU177641B/hu unknown
- 1977-12-22 FI FI773906A patent/FI773906A/fi not_active Application Discontinuation
- 1977-12-22 SE SE7714648A patent/SE425487B/sv not_active IP Right Cessation
- 1977-12-22 IE IE2606/77A patent/IE46126B1/en not_active IP Right Cessation
- 1977-12-22 GR GR55041A patent/GR71189B/el unknown
- 1977-12-22 IT IT31162/77A patent/IT1089319B/it active
- 1977-12-22 IL IL53673A patent/IL53673A/xx unknown
- 1977-12-22 PH PH20590A patent/PH14409A/en unknown
- 1977-12-22 NZ NZ186094A patent/NZ186094A/xx unknown
- 1977-12-23 CA CA293,820A patent/CA1093565A/en not_active Expired
- 1977-12-23 PT PT67449A patent/PT67449B/pt unknown
- 1977-12-23 GB GB53706/77A patent/GB1589339A/en not_active Expired
- 1977-12-23 AU AU31956/77A patent/AU516399B2/en not_active Expired
- 1977-12-23 DK DK577477A patent/DK162088C/da active
- 1977-12-23 AT AT0928077A patent/AT371806B/de not_active IP Right Cessation
- 1977-12-23 GB GB23734/79A patent/GB1589340A/en not_active Expired
- 1977-12-23 NO NO774455A patent/NO774455L/no unknown
- 1977-12-24 JP JP15633377A patent/JPS5379859A/ja active Granted
-
1978
- 1978-07-10 FR FR7820499A patent/FR2383925A1/fr active Granted
-
1982
- 1982-05-04 SE SE8202788A patent/SE426240B/sv not_active IP Right Cessation
- 1982-05-27 NO NO821761A patent/NO821761L/no unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1064933A (en) | Benzoic acids, their derivatives and process for preparing them | |
| NO813066L (no) | Isokinolinderivater, fremgangsmaate til deres fremstilling, farmasoeytiske tilberedninger, innhold og deres anvendelse | |
| NO124724B (sv) | ||
| CA1208643A (en) | 1,5-diphenyl-pyrazolin-3-one compounds, process and intermediates for preparation thereof and pharmaceutical compositions containing them | |
| NO151387B (no) | Innstillingsinnretning for en elektronisk digitalindikator | |
| NO774455L (no) | Fremgangsmaate til fremstilling av pyrrolo-benzosyre-derivater | |
| US3454577A (en) | 4-(1,2,3,4,5,6,7,8 - octahydro - 1,8 - dioxo-9-acridanyl) - benzenesulfonamide and derivatives | |
| Werner et al. | Derivatives of Morphanthridine1 | |
| US4492710A (en) | Substituted pyrrolidinyl-benzoic acid derivatives and a process for their manufacture | |
| US4411907A (en) | Antiinflammatory 3H-naphtho(1,2-d)imidazoles | |
| DK169406B1 (da) | Hydroxyalkoxy-4-phenylpropylindolforbindelser, deres fremstilling samt lægemidler med indhold deraf | |
| US4960785A (en) | Indolinone derivatives | |
| US3992440A (en) | 4-Ethers of 3-amino-5-sulfamoylbenzoic acids | |
| NO744713L (sv) | ||
| US3982018A (en) | 4-Ethers of 3-amino-5-sulfamoylbenzoic acids | |
| GB1589396A (en) | 1,2,3,4-tetrahydro-9h-pyrrolo(3,4-b)quinolin-9-one and derivatives thereof | |
| US4845122A (en) | Anti-allergy treatment using 2-(substituted amino)-4,5-dihydro-4-oxo-3-furancarboxylic acids and derivatives thereof | |
| US3211745A (en) | Demvatives of j-cyclopropylamesfo- methyl-indole | |
| DE2718494A1 (de) | Verfahren zur herstellung von pyrrolo-benzoesaeure-derivaten | |
| US3536757A (en) | Substituted dioxocyclohexyl-p-toluenesulfonamides | |
| IE46127B1 (en) | Pyrrolo-benzoic acid derivatives and process for their preparation | |
| DK156432B (da) | 3-n-pyrrolo-5-sulfamoylbenzoesyre-derivater til anvendelse som mellemprodukter ved fremstilling af 3-n-pyrrolidino-5-sulfamoylbenzoesyre-derivater | |
| KR820000366B1 (ko) | 피롤로-벤조산 유도체의 제조 방법 | |
| US3431274A (en) | 1-phenylbenzimidazole-2-methanol | |
| US3927218A (en) | 3,4-Bisamino-5-sulfamoylbenzoic acids useful as diuretic agents |