DE2623447A1 - N-substituierte 2-methoxy-benzolsulfonamide, verfahren zu ihrer herstellung und sie enthaltende arzneimittel - Google Patents
N-substituierte 2-methoxy-benzolsulfonamide, verfahren zu ihrer herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE2623447A1 DE2623447A1 DE19762623447 DE2623447A DE2623447A1 DE 2623447 A1 DE2623447 A1 DE 2623447A1 DE 19762623447 DE19762623447 DE 19762623447 DE 2623447 A DE2623447 A DE 2623447A DE 2623447 A1 DE2623447 A1 DE 2623447A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- amino
- general formula
- chloro
- nitro
- 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.)
- Withdrawn
Links
- -1 N-SUBSTITUTED 2-METHOXY-BENZOLSULPHONAMIDE Chemical class 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title description 13
- 229940126601 medicinal product Drugs 0.000 title description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 19
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- GYOBZOBUOMDRRN-UHFFFAOYSA-N 2-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=CC=C1S(Cl)(=O)=O GYOBZOBUOMDRRN-UHFFFAOYSA-N 0.000 claims description 9
- 239000012954 diazonium Substances 0.000 claims description 9
- 150000001989 diazonium salts Chemical class 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 claims description 6
- 150000004982 aromatic amines Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- POKAEVPBUOLQIY-UHFFFAOYSA-N 5-chloro-2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=C(Cl)C=C1N POKAEVPBUOLQIY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000008331 benzenesulfonamides Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 claims description 3
- CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical compound COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 claims description 3
- VQYGQLLWJKBXFD-UHFFFAOYSA-N 4-amino-5-chloro-n-[3-(diethylamino)propyl]-2-methoxybenzenesulfonamide Chemical compound CCN(CC)CCCNS(=O)(=O)C1=CC(Cl)=C(N)C=C1OC VQYGQLLWJKBXFD-UHFFFAOYSA-N 0.000 claims description 3
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical group COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 claims description 3
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 claims description 2
- JMUCXULQKPWSTJ-UHFFFAOYSA-N 3-piperidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCCC1 JMUCXULQKPWSTJ-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 238000006193 diazotization reaction Methods 0.000 claims description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 claims description 2
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 claims description 2
- GADIREFQKKSFKX-UHFFFAOYSA-N n-propylmorpholin-4-amine Chemical compound CCCNN1CCOCC1 GADIREFQKKSFKX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- KFKOUEORGRALRU-UHFFFAOYSA-N 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-methoxybenzenesulfonamide Chemical compound CCN(CC)CCNS(=O)(=O)C1=CC(Cl)=C(N)C=C1OC KFKOUEORGRALRU-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 14
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000003474 anti-emetic effect Effects 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229940124530 sulfonamide Drugs 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 150000003456 sulfonamides Chemical class 0.000 description 6
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 5
- 206010047700 Vomiting Diseases 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003589 local anesthetic agent Substances 0.000 description 5
- 229940075930 picrate Drugs 0.000 description 5
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 230000001773 anti-convulsant effect Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000001376 precipitating effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 230000008673 vomiting Effects 0.000 description 4
- NPWOQOWGIUVRAU-UHFFFAOYSA-N 3-amino-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1N NPWOQOWGIUVRAU-UHFFFAOYSA-N 0.000 description 3
- OSAYFGJUEOYRHY-UHFFFAOYSA-N 4-chloro-1-methoxy-2-nitrobenzene Chemical compound COC1=CC=C(Cl)C=C1[N+]([O-])=O OSAYFGJUEOYRHY-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002111 antiemetic agent Substances 0.000 description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 3
- 229960004046 apomorphine Drugs 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 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 2
- YRGAYAGBVIXNAQ-UHFFFAOYSA-N 1-chloro-4-methoxybenzene Chemical compound COC1=CC=C(Cl)C=C1 YRGAYAGBVIXNAQ-UHFFFAOYSA-N 0.000 description 2
- QECYXMKYZQXEHM-UHFFFAOYSA-N 2-methoxy-4-nitrobenzenesulfonyl chloride Chemical compound COC1=CC([N+]([O-])=O)=CC=C1S(Cl)(=O)=O QECYXMKYZQXEHM-UHFFFAOYSA-N 0.000 description 2
- NWSIFTLPLKCTSX-UHFFFAOYSA-N 4-chloro-2-nitrophenol Chemical compound OC1=CC=C(Cl)C=C1[N+]([O-])=O NWSIFTLPLKCTSX-UHFFFAOYSA-N 0.000 description 2
- JESBYSXPKUMFRV-UHFFFAOYSA-N 4-methoxy-3-nitrobenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1[N+]([O-])=O JESBYSXPKUMFRV-UHFFFAOYSA-N 0.000 description 2
- PWYNJONRUFAOFG-UHFFFAOYSA-N 4-methoxy-3-nitrobenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1[N+]([O-])=O PWYNJONRUFAOFG-UHFFFAOYSA-N 0.000 description 2
- JEOMQYSORAVXEZ-UHFFFAOYSA-N 5-chloro-2-methoxy-4-nitrobenzenesulfonyl chloride Chemical compound COC1=CC([N+]([O-])=O)=C(Cl)C=C1S(Cl)(=O)=O JEOMQYSORAVXEZ-UHFFFAOYSA-N 0.000 description 2
- FCJGLIMDVOTBLO-UHFFFAOYSA-N 5-chloro-2-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(Cl)C=C1S(Cl)(=O)=O FCJGLIMDVOTBLO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- 102100026197 C-type lectin domain family 2 member D Human genes 0.000 description 2
- 101000912615 Homo sapiens C-type lectin domain family 2 member D Proteins 0.000 description 2
- ABDMQSFNJPYOLA-UHFFFAOYSA-N NS(=O)(=O)[N+]([O-])=O Chemical compound NS(=O)(=O)[N+]([O-])=O ABDMQSFNJPYOLA-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
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- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 229940125683 antiemetic agent Drugs 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
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- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 229960005015 local anesthetics Drugs 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- KQGNEXQCCNUZMT-UHFFFAOYSA-N n-(5-chloro-2-methoxy-4-nitrophenyl)acetamide Chemical compound COC1=CC([N+]([O-])=O)=C(Cl)C=C1NC(C)=O KQGNEXQCCNUZMT-UHFFFAOYSA-N 0.000 description 2
- WKZLKZPMUWYXTK-UHFFFAOYSA-N n-(5-chloro-2-methoxyphenyl)acetamide Chemical compound COC1=CC=C(Cl)C=C1NC(C)=O WKZLKZPMUWYXTK-UHFFFAOYSA-N 0.000 description 2
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- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 238000005406 washing Methods 0.000 description 2
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- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- TYEWCFOXOODIQX-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]benzenesulfonamide Chemical compound CCN(CC)CCNS(=O)(=O)C1=CC=CC=C1 TYEWCFOXOODIQX-UHFFFAOYSA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
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- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
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- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BPSUJSDZHLTNJR-UHFFFAOYSA-N sulfamide;hydrochloride Chemical compound Cl.NS(N)(=O)=O BPSUJSDZHLTNJR-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 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
- C07D295/12—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 singly or doubly bound nitrogen atoms
- C07D295/125—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7517973A FR2313918A1 (fr) | 1975-06-09 | 1975-06-09 | Methoxy-2 benzenesulfonamides n-substitues, procede pour les preparer et medicaments les contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2623447A1 true DE2623447A1 (de) | 1977-01-13 |
Family
ID=9156225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762623447 Withdrawn DE2623447A1 (de) | 1975-06-09 | 1976-05-25 | N-substituierte 2-methoxy-benzolsulfonamide, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4132786A (OSRAM) |
| JP (2) | JPS6049630B2 (OSRAM) |
| AT (1) | AT358555B (OSRAM) |
| BE (1) | BE842753A (OSRAM) |
| CA (1) | CA1083573A (OSRAM) |
| CH (1) | CH616917A5 (OSRAM) |
| DE (1) | DE2623447A1 (OSRAM) |
| DK (1) | DK146592C (OSRAM) |
| ES (1) | ES448646A1 (OSRAM) |
| FR (1) | FR2313918A1 (OSRAM) |
| GB (1) | GB1545628A (OSRAM) |
| NL (1) | NL7606172A (OSRAM) |
| SE (1) | SE430248B (OSRAM) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0021580A1 (en) * | 1979-05-16 | 1981-01-07 | BEECHAM - WUELFING GmbH & Co. KG | Sulphonamide derivatives, a process for their preparation and their use as medicines |
| EP0021592A1 (en) * | 1979-05-23 | 1981-01-07 | BEECHAM - WUELFING GmbH & Co. KG | Phenylsulphonamide derivatives, a process for their preparation and their use as medicines |
| EP0260901A1 (en) * | 1986-09-18 | 1988-03-23 | American Home Products Corporation | Benzenesulphonamides useful as anti-arrythmic agents |
| EP0306453A3 (en) * | 1987-09-04 | 1990-04-18 | Ciba-Geigy Ag | Process for the preparation of 2-(2-chloroethoxy)-benzosulfon amide |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2504528A1 (fr) * | 1981-04-23 | 1982-10-29 | Choay Sa | Dialcoxy (2,4) benzenesulfonamides n-substitues |
| US4714700A (en) * | 1982-04-20 | 1987-12-22 | Choay S.A. | N-substituted 2,4-dialkoxy benzenesulfonamides and pharmaceutical compositions |
| US4483864A (en) * | 1983-02-04 | 1984-11-20 | University Of Iowa Research Foundation | Non-classical topical treatment for glaucoma |
| GB2160201B (en) * | 1984-06-14 | 1988-05-11 | Wyeth John & Brother Ltd | Quinazoline and cinnoline derivatives |
| US4629738A (en) * | 1984-06-25 | 1986-12-16 | University Of Iowa Research Foundation | Non-classical topical treatment for glaucoma |
| US4731369A (en) * | 1985-11-06 | 1988-03-15 | Merck & Co. Inc. | Amides and esters of 2-(N-(hydroxypiperidinoalkyl) and (hydroxypyrrolidinoalkyl)-aminosulfonyl)-6-nitrobenzoic acids useful as adjuncts to radiation therapy |
| US5391757A (en) * | 1987-08-17 | 1995-02-21 | American Cyanamid Company | Benzenesulfonyl carboxamide compounds intermediate compounds and methods of preparation thereof and use of said compounds and intermediate compounds as herbicidal agents |
| US4883914A (en) * | 1987-08-17 | 1989-11-28 | American Cyanamid Company | Benzenesulfonyl carboxamide compounds useful as herbicidal agents |
| US5120854A (en) * | 1987-08-17 | 1992-06-09 | American Cyanamid Company | Benzenesulfonyl carboxamide compounds and intermediate compounds |
| US4992094A (en) * | 1987-08-17 | 1991-02-12 | American Cyanamid Company | Phenylsulfonyl 2-imidazolin-5-one compounds |
| US5252539A (en) * | 1987-08-17 | 1993-10-12 | American Cyanamid Company | Benzenesulfonyl carboxamide compounds intermediate compounds and method of preparation thereof and use of said compounds and intermediate compounds as herbicidal agents |
| US5338883A (en) * | 1987-08-17 | 1994-08-16 | American Cyanamid Company | Benzenesulfonyl carboxamide compounds intermediate compounds and methods of preparation thereof and use of said compounds and intermediate compounds as herbicidal agents |
| JP2556722B2 (ja) * | 1988-02-18 | 1996-11-20 | 興和株式会社 | 新規なスルホンアミド化合物 |
| JP2000504677A (ja) * | 1996-02-09 | 2000-04-18 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ５ｈｔ７レセプター・アンタゴニスト用のスルホンアミド誘導体 |
| GB9803536D0 (en) * | 1998-02-19 | 1998-04-15 | Black James Foundation | Histamine H,receptor ligands |
| US20100048713A1 (en) * | 2006-01-06 | 2010-02-25 | Aarhus Universitet | Compounds acting on the serotonin transporter |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1145182B (de) * | 1957-06-17 | 1963-03-14 | Du Pont | Verfahren zur Herstellung von 4-Alkoxymetanilamiden und deren Salzen |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3139381A (en) * | 1957-02-07 | 1964-06-30 | Merck & Co Inc | Process of effecting diuresis with nitro disulfamylaniline compounds |
| US3060206A (en) * | 1960-09-27 | 1962-10-23 | Merck & Co Inc | 2, 4-disulfamyl-5-alkoxy-aniline |
| US3580949A (en) * | 1965-03-19 | 1971-05-25 | Hoffmann La Roche | N,n'-bis-(aminoalkyl)-benzyl-amines |
| US3840569A (en) * | 1972-11-13 | 1974-10-08 | Lilly Co Eli | N1-aryloxy(arylthio)dinitro-sulfanilamides |
| CH590830A5 (OSRAM) * | 1973-02-20 | 1977-08-31 | Hoechst Ag |
-
1975
- 1975-06-09 FR FR7517973A patent/FR2313918A1/fr active Granted
-
1976
- 1976-05-25 DE DE19762623447 patent/DE2623447A1/de not_active Withdrawn
- 1976-06-01 AT AT401976A patent/AT358555B/de not_active IP Right Cessation
- 1976-06-03 CA CA253,973A patent/CA1083573A/en not_active Expired
- 1976-06-07 JP JP51065723A patent/JPS6049630B2/ja not_active Expired
- 1976-06-08 CH CH717976A patent/CH616917A5/fr not_active IP Right Cessation
- 1976-06-08 DK DK252376A patent/DK146592C/da active
- 1976-06-08 SE SE7606440A patent/SE430248B/xx not_active IP Right Cessation
- 1976-06-08 NL NL7606172A patent/NL7606172A/xx not_active Application Discontinuation
- 1976-06-08 GB GB23701/76A patent/GB1545628A/en not_active Expired
- 1976-06-08 US US05/693,896 patent/US4132786A/en not_active Expired - Lifetime
- 1976-06-08 ES ES448646A patent/ES448646A1/es not_active Expired
- 1976-06-09 BE BE167761A patent/BE842753A/xx not_active IP Right Cessation
-
1985
- 1985-04-30 JP JP60091304A patent/JPS60243060A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1145182B (de) * | 1957-06-17 | 1963-03-14 | Du Pont | Verfahren zur Herstellung von 4-Alkoxymetanilamiden und deren Salzen |
Non-Patent Citations (2)
| Title |
|---|
| Eur.J.Med.Chem.Chimica Therapeutica, S.424 * |
| HOUBEN-WEYL: Methoden der organischen Chemie, 4.Aufl., Bd.IX, S.579-580 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0021580A1 (en) * | 1979-05-16 | 1981-01-07 | BEECHAM - WUELFING GmbH & Co. KG | Sulphonamide derivatives, a process for their preparation and their use as medicines |
| EP0021592A1 (en) * | 1979-05-23 | 1981-01-07 | BEECHAM - WUELFING GmbH & Co. KG | Phenylsulphonamide derivatives, a process for their preparation and their use as medicines |
| EP0260901A1 (en) * | 1986-09-18 | 1988-03-23 | American Home Products Corporation | Benzenesulphonamides useful as anti-arrythmic agents |
| EP0306453A3 (en) * | 1987-09-04 | 1990-04-18 | Ciba-Geigy Ag | Process for the preparation of 2-(2-chloroethoxy)-benzosulfon amide |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6049630B2 (ja) | 1985-11-02 |
| ATA401976A (de) | 1980-02-15 |
| CA1083573A (en) | 1980-08-12 |
| JPS60243060A (ja) | 1985-12-03 |
| FR2313918A1 (fr) | 1977-01-07 |
| CH616917A5 (OSRAM) | 1980-04-30 |
| BE842753A (fr) | 1976-12-09 |
| DK252376A (da) | 1976-12-10 |
| JPS5231044A (en) | 1977-03-09 |
| ES448646A1 (es) | 1977-07-01 |
| GB1545628A (en) | 1979-05-10 |
| SE7606440L (sv) | 1976-12-10 |
| SE430248B (sv) | 1983-10-31 |
| AT358555B (de) | 1980-09-25 |
| DK146592B (da) | 1983-11-14 |
| NL7606172A (nl) | 1976-12-13 |
| US4132786A (en) | 1979-01-02 |
| DK146592C (da) | 1984-06-12 |
| FR2313918B1 (OSRAM) | 1978-10-06 |
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Legal Events
| Date | Code | Title | Description |
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| 8110 | Request for examination paragraph 44 | ||
| 8139 | Disposal/non-payment of the annual fee |