FI57934C - Foerfarande foer framstaellning av terapeutiskt anvaendbara sulfamoylfenylimidazolidiner - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara sulfamoylfenylimidazolidiner Download PDFInfo
- Publication number
- FI57934C FI57934C FI3561/73A FI356173A FI57934C FI 57934 C FI57934 C FI 57934C FI 3561/73 A FI3561/73 A FI 3561/73A FI 356173 A FI356173 A FI 356173A FI 57934 C FI57934 C FI 57934C
- Authority
- FI
- Finland
- Prior art keywords
- chloro
- phenyl
- sulfamoyl
- found
- requires
- Prior art date
Links
- TZRYKIKPCVXXMN-UHFFFAOYSA-N 1-phenylimidazolidine-2-sulfonamide Chemical compound S(N)(=O)(=O)C1N(CCN1)C1=CC=CC=C1 TZRYKIKPCVXXMN-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 32
- -1 pyrocarbonate ester Chemical class 0.000 claims description 32
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 239000000047 product Substances 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- 239000000203 mixture Substances 0.000 description 43
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 22
- 229930040373 Paraformaldehyde Natural products 0.000 description 17
- 229920002866 paraformaldehyde Polymers 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 5
- 229960002036 phenytoin Drugs 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 229940091173 hydantoin Drugs 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101100063435 Caenorhabditis elegans din-1 gene Proteins 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 101100441092 Danio rerio crlf3 gene Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 208000034308 Grand mal convulsion Diseases 0.000 description 2
- JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
- 206010034759 Petit mal epilepsy Diseases 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- IARPZHLEAKMUCD-UHFFFAOYSA-N [2-(2-chloro-4-sulfamoylanilino)-2-oxoethyl]-phenylcarbamic acid Chemical compound ClC1=CC(S(=O)(=O)N)=CC=C1NC(=O)CN(C(O)=O)C1=CC=CC=C1 IARPZHLEAKMUCD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000006358 imidation reaction Methods 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- PRFJDJAOBGAIPS-UHFFFAOYSA-N n-phenyl-2-sulfamoylacetamide Chemical compound NS(=O)(=O)CC(=O)NC1=CC=CC=C1 PRFJDJAOBGAIPS-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 229960005152 pentetrazol Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FQMFBLVJDKPMNZ-UHFFFAOYSA-N 2-(4-chloroanilino)-N-(2-sulfamoylphenyl)acetamide Chemical compound ClC1=CC=C(NCC(=O)NC2=C(C=CC=C2)S(N)(=O)=O)C=C1 FQMFBLVJDKPMNZ-UHFFFAOYSA-N 0.000 description 1
- YOCIJWAHRAJQFT-UHFFFAOYSA-N 2-bromo-2-methylpropanoyl bromide Chemical compound CC(C)(Br)C(Br)=O YOCIJWAHRAJQFT-UHFFFAOYSA-N 0.000 description 1
- CLUZBEDAQBTAHF-UHFFFAOYSA-N 2-bromo-n-(2-chloro-4-sulfamoylphenyl)propanamide Chemical compound CC(Br)C(=O)NC1=CC=C(S(N)(=O)=O)C=C1Cl CLUZBEDAQBTAHF-UHFFFAOYSA-N 0.000 description 1
- AZURFBCEYQYATI-UHFFFAOYSA-N 2-chloro-n-(4-nitrophenyl)acetamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)CCl)C=C1 AZURFBCEYQYATI-UHFFFAOYSA-N 0.000 description 1
- RLFIWYGMZQJEFO-UHFFFAOYSA-N 2-chloro-n-cyclohexylacetamide Chemical compound ClCC(=O)NC1CCCCC1 RLFIWYGMZQJEFO-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- HLPIHRDZBHXTFJ-UHFFFAOYSA-N 2-ethylfuran Chemical compound CCC1=CC=CO1 HLPIHRDZBHXTFJ-UHFFFAOYSA-N 0.000 description 1
- LJGMIOMVROODJU-UHFFFAOYSA-N 2-phenyl-1H-imidazole-5-sulfonamide Chemical compound NS(=O)(=O)C=1N=C(NC1)C1=CC=CC=C1 LJGMIOMVROODJU-UHFFFAOYSA-N 0.000 description 1
- LDQZXOBSWYSJSI-UHFFFAOYSA-N 3-chloro-4-(3-cyclohexyl-5-oxoimidazolidin-1-yl)benzenesulfonamide Chemical compound ClC1=CC(S(=O)(=O)N)=CC=C1N1C(=O)CN(C2CCCCC2)C1 LDQZXOBSWYSJSI-UHFFFAOYSA-N 0.000 description 1
- NJWPBUCTYQFQRT-UHFFFAOYSA-N 3-chloro-4-(4-methyl-5-oxo-3-phenylimidazolidin-1-yl)benzenesulfonamide Chemical compound O=C1C(C)N(C=2C=CC=CC=2)CN1C1=CC=C(S(N)(=O)=O)C=C1Cl NJWPBUCTYQFQRT-UHFFFAOYSA-N 0.000 description 1
- JWGLQMPCGXNYSR-UHFFFAOYSA-N 3-chloro-4-[3-(3-chlorophenyl)-5-oxoimidazolidin-1-yl]benzenesulfonamide Chemical compound ClC1=CC(S(=O)(=O)N)=CC=C1N1C(=O)CN(C=2C=C(Cl)C=CC=2)C1 JWGLQMPCGXNYSR-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 101100274575 Caenorhabditis elegans clh-3 gene Proteins 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 235000010624 Medicago sativa Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-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
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000700647 Variola virus Species 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical compound O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 125000001835 p-methoxyanilino group Chemical group [H]N(*)C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5343772A GB1408010A (en) | 1972-11-20 | 1972-11-20 | Sulphamoylphenyl-imidazolidinones |
| GB5343772 | 1972-11-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI57934B FI57934B (fi) | 1980-07-31 |
| FI57934C true FI57934C (fi) | 1980-11-10 |
Family
ID=10467808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3561/73A FI57934C (fi) | 1972-11-20 | 1973-11-19 | Foerfarande foer framstaellning av terapeutiskt anvaendbara sulfamoylfenylimidazolidiner |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3963706A (de) |
| JP (1) | JPS541312B2 (de) |
| AR (1) | AR211379Q (de) |
| AT (1) | AT330766B (de) |
| AU (1) | AU470359B2 (de) |
| BE (1) | BE807490A (de) |
| CA (1) | CA1021783A (de) |
| CH (3) | CH605808A5 (de) |
| DE (1) | DE2357591C3 (de) |
| DK (1) | DK138645B (de) |
| ES (1) | ES420661A1 (de) |
| FI (1) | FI57934C (de) |
| FR (1) | FR2206947B1 (de) |
| GB (1) | GB1408010A (de) |
| HU (1) | HU170143B (de) |
| IE (1) | IE39319B1 (de) |
| IL (1) | IL43652A (de) |
| NL (1) | NL7315807A (de) |
| PL (1) | PL97758B1 (de) |
| SE (1) | SE417960B (de) |
| ZA (1) | ZA738824B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100519525C (zh) * | 1999-12-06 | 2009-07-29 | 葛兰素集团有限公司 | 芳香砜类及其医疗用途 |
| JP2003515558A (ja) | 1999-12-06 | 2003-05-07 | ロード アイランド ホスピタル， ア ライフスパン パートナー | 腫瘍を治療するためのメチロール含有化合物の使用 |
| YU52403A (sh) * | 2000-12-26 | 2006-03-03 | Dr.Reddy's Research Foundation | Heterociklična jedinjenja koja imaju antibakterijsko dejstvo, postupak za njihovo dobijanje i farmaceutske smeše koje ih sadrže |
| US7160912B2 (en) | 2000-12-26 | 2007-01-09 | Dr.Reddy's Laboratories Ltd. | Heterocyclic compounds having antibacterial activity: process for their preparation and pharmaceutical compositions containing them |
| EP1450814B1 (de) | 2001-10-01 | 2016-11-30 | Geistlich Pharma AG | Verfahren zur hemmung von metastasen |
| US20070004712A1 (en) * | 2001-12-21 | 2007-01-04 | Dr. Reddy's Laboratories Ltd. | Salts of novel heterocyclic compounds having antibacterial activity |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1472625A (de) * | 1965-03-31 | 1967-05-24 |
-
1972
- 1972-11-20 GB GB5343772A patent/GB1408010A/en not_active Expired
-
1973
- 1973-06-19 IL IL43652A patent/IL43652A/en unknown
- 1973-11-19 NL NL7315807A patent/NL7315807A/xx not_active Application Discontinuation
- 1973-11-19 SE SE7315644A patent/SE417960B/xx unknown
- 1973-11-19 CA CA186,100A patent/CA1021783A/en not_active Expired
- 1973-11-19 JP JP12927973A patent/JPS541312B2/ja not_active Expired
- 1973-11-19 IE IE2094/73A patent/IE39319B1/xx unknown
- 1973-11-19 CH CH1621173A patent/CH605808A5/xx not_active IP Right Cessation
- 1973-11-19 BE BE137896A patent/BE807490A/xx unknown
- 1973-11-19 AR AR251062A patent/AR211379Q/es unknown
- 1973-11-19 US US05/416,854 patent/US3963706A/en not_active Expired - Lifetime
- 1973-11-19 ES ES420661A patent/ES420661A1/es not_active Expired
- 1973-11-19 AU AU62660/73A patent/AU470359B2/en not_active Expired
- 1973-11-19 DK DK622673AA patent/DK138645B/da not_active IP Right Cessation
- 1973-11-19 FR FR7341140A patent/FR2206947B1/fr not_active Expired
- 1973-11-19 PL PL1973166622A patent/PL97758B1/pl unknown
- 1973-11-19 FI FI3561/73A patent/FI57934C/fi active
- 1973-11-19 CH CH1393177A patent/CH603594A5/xx not_active IP Right Cessation
- 1973-11-19 CH CH1601476A patent/CH605802A5/xx not_active IP Right Cessation
- 1973-11-19 ZA ZA738824A patent/ZA738824B/xx unknown
- 1973-11-19 HU HUGE946A patent/HU170143B/hu unknown
- 1973-11-19 AT AT968773A patent/AT330766B/de not_active IP Right Cessation
- 1973-11-19 DE DE2357591A patent/DE2357591C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1408010A (en) | 1975-10-01 |
| BE807490A (fr) | 1974-05-20 |
| CH603594A5 (de) | 1978-08-31 |
| US3963706A (en) | 1976-06-15 |
| DE2357591A1 (de) | 1974-05-22 |
| AT330766B (de) | 1976-07-26 |
| FI57934B (fi) | 1980-07-31 |
| DK138645B (da) | 1978-10-09 |
| FR2206947A1 (de) | 1974-06-14 |
| FR2206947B1 (de) | 1977-10-28 |
| AU470359B2 (en) | 1975-05-22 |
| IL43652A0 (en) | 1974-03-14 |
| DE2357591B2 (de) | 1979-07-05 |
| AR211379Q (es) | 1977-12-15 |
| CH605802A5 (de) | 1978-10-13 |
| IE39319B1 (en) | 1978-09-13 |
| CH605808A5 (de) | 1978-10-13 |
| ES420661A1 (es) | 1976-04-01 |
| SE417960B (sv) | 1981-04-27 |
| AU6266073A (en) | 1975-05-22 |
| CA1021783A (en) | 1977-11-29 |
| HU170143B (de) | 1977-04-28 |
| IL43652A (en) | 1977-10-31 |
| DK138645C (de) | 1979-03-19 |
| IE39319L (en) | 1974-05-20 |
| JPS541312B2 (de) | 1979-01-23 |
| PL97758B1 (pl) | 1978-03-30 |
| NL7315807A (de) | 1974-05-22 |
| JPS4993362A (de) | 1974-09-05 |
| DE2357591C3 (de) | 1980-02-28 |
| ATA968773A (de) | 1975-10-15 |
| ZA738824B (en) | 1974-09-25 |
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