NO130549B - - Google Patents
Download PDFInfo
- Publication number
- NO130549B NO130549B NO02931/72*[A NO293172A NO130549B NO 130549 B NO130549 B NO 130549B NO 293172 A NO293172 A NO 293172A NO 130549 B NO130549 B NO 130549B
- Authority
- NO
- Norway
- Prior art keywords
- group
- chloro
- carboxy
- sulfamyl
- radical
- Prior art date
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 31
- -1 di-substituted carbamyl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 229910021529 ammonia Inorganic materials 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- OAZOBYBYAKXURF-UHFFFAOYSA-N 2-(sulfamoylamino)benzoic acid Chemical compound NS(=O)(=O)NC1=CC=CC=C1C(O)=O OAZOBYBYAKXURF-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 230000009435 amidation Effects 0.000 claims description 5
- 238000007112 amidation reaction Methods 0.000 claims description 5
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 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
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005910 alkyl carbonate group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 7
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 7
- CHQWLWFOYFRJDY-UHFFFAOYSA-N n-phenylheptanamide Chemical compound CCCCCCC(=O)NC1=CC=CC=C1 CHQWLWFOYFRJDY-UHFFFAOYSA-N 0.000 description 7
- QQLJBZFXGDHSRU-UHFFFAOYSA-N 2-amino-4-chloro-5-sulfamoylbenzoic acid Chemical compound NC1=CC(Cl)=C(S(N)(=O)=O)C=C1C(O)=O QQLJBZFXGDHSRU-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- AQHVWJACZZWZPW-UHFFFAOYSA-N n-(5-chloro-2-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1C AQHVWJACZZWZPW-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 5
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical class C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002934 diuretic Substances 0.000 description 5
- 230000001882 diuretic effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- DZOIWQLHRHWDLW-UHFFFAOYSA-N 2-amino-4-nitro-5-sulfamoylbenzoic acid Chemical compound C(=O)(O)C1=C(N)C=C(C(=C1)S(N)(=O)=O)[N+](=O)[O-] DZOIWQLHRHWDLW-UHFFFAOYSA-N 0.000 description 3
- YKSYVNJABNVTPC-UHFFFAOYSA-N 2-benzamido-4-chloro-5-sulfamoylbenzoic acid Chemical compound C(=O)(O)C1=C(NC(C2=CC=CC=C2)=O)C=C(C(=C1)S(N)(=O)=O)Cl YKSYVNJABNVTPC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YZVLDYQGTHLMDZ-UHFFFAOYSA-N 2-amino-4-chloro-5-sulfamoylbenzamide Chemical compound NC(=O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1N YZVLDYQGTHLMDZ-UHFFFAOYSA-N 0.000 description 2
- GWYDFPHNDNZJKB-UHFFFAOYSA-N 2-amino-4-methyl-5-sulfamoylbenzoic acid Chemical compound S(N)(=O)(=O)C1=C(C=C(N)C(=C1)C(=O)O)C GWYDFPHNDNZJKB-UHFFFAOYSA-N 0.000 description 2
- RLCMQWBYWOIEGD-UHFFFAOYSA-N 2-aminobenzoyl chloride Chemical compound NC1=CC=CC=C1C(Cl)=O RLCMQWBYWOIEGD-UHFFFAOYSA-N 0.000 description 2
- IGQGXIVCGKMRAM-UHFFFAOYSA-N 4-amino-3-methylbenzenesulfonamide Chemical compound CC1=CC(S(N)(=O)=O)=CC=C1N IGQGXIVCGKMRAM-UHFFFAOYSA-N 0.000 description 2
- LNWMQCKSOZMVIC-UHFFFAOYSA-N 4-chloro-2-(methylamino)-5-sulfamoylbenzoic acid Chemical compound CNC1=CC(Cl)=C(S(N)(=O)=O)C=C1C(O)=O LNWMQCKSOZMVIC-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- WRRDUYVTNRWZST-UHFFFAOYSA-N n-pentyl-n-phenylbutanamide Chemical compound CCCCCN(C(=O)CCC)C1=CC=CC=C1 WRRDUYVTNRWZST-UHFFFAOYSA-N 0.000 description 2
- 230000001452 natriuretic effect Effects 0.000 description 2
- 230000000894 saliuretic effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 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 1
- IPQWEJRKWJKATM-UHFFFAOYSA-N 2-(butanoylamino)-4-chloro-5-sulfamoylbenzoic acid Chemical compound C(=O)(O)C1=C(NC(CCC)=O)C=C(C(=C1)S(N)(=O)=O)Cl IPQWEJRKWJKATM-UHFFFAOYSA-N 0.000 description 1
- VMZJKMRYIXGYPX-UHFFFAOYSA-N 2-(carbamoylamino)-4-chloro-5-sulfamoylbenzoic acid Chemical compound NC(=O)NC1=CC(Cl)=C(S(N)(=O)=O)C=C1C(O)=O VMZJKMRYIXGYPX-UHFFFAOYSA-N 0.000 description 1
- UVECPLHQYFROMQ-UHFFFAOYSA-N 2-(ethylamino)-4-nitrobenzoic acid Chemical compound CCNC1=CC([N+]([O-])=O)=CC=C1C(O)=O UVECPLHQYFROMQ-UHFFFAOYSA-N 0.000 description 1
- YDRXTUWNXMAPGB-UHFFFAOYSA-N 2-(sulfamoylamino)benzamide Chemical compound NC(=O)C1=CC=CC=C1NS(N)(=O)=O YDRXTUWNXMAPGB-UHFFFAOYSA-N 0.000 description 1
- HHNWXQCVWVVVQZ-UHFFFAOYSA-N 2-amino-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(N)=C1 HHNWXQCVWVVVQZ-UHFFFAOYSA-N 0.000 description 1
- RPGKFFKUTVJVPY-UHFFFAOYSA-N 2-amino-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(N)=C1 RPGKFFKUTVJVPY-UHFFFAOYSA-N 0.000 description 1
- SSEZSHJJNNLTQI-UHFFFAOYSA-N 2-amino-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1N SSEZSHJJNNLTQI-UHFFFAOYSA-N 0.000 description 1
- WRSJGAYEESYXCR-UHFFFAOYSA-N 4-chloro-2-(dodecanoylamino)-5-sulfamoylbenzoic acid Chemical compound C(=O)(O)C1=C(NC(CCCCCCCCCCC)=O)C=C(C(=C1)S(N)(=O)=O)Cl WRSJGAYEESYXCR-UHFFFAOYSA-N 0.000 description 1
- AIKBBXVMNYCRDO-UHFFFAOYSA-N 4-chloro-2-(methylamino)benzoic acid Chemical compound CNC1=CC(Cl)=CC=C1C(O)=O AIKBBXVMNYCRDO-UHFFFAOYSA-N 0.000 description 1
- UEALKTCRMBVTFN-UHFFFAOYSA-N 4-nitroanthranilic acid Chemical compound NC1=CC([N+]([O-])=O)=CC=C1C(O)=O UEALKTCRMBVTFN-UHFFFAOYSA-N 0.000 description 1
- UBTDYGGPHDGMGS-UHFFFAOYSA-N 5-chloro-2-methyl-n-propylaniline Chemical compound CCCNC1=CC(Cl)=CC=C1C UBTDYGGPHDGMGS-UHFFFAOYSA-N 0.000 description 1
- KYMYXNHLTLXRFO-UHFFFAOYSA-N C(=O)(O)C1=C(N)C=C(C(=C1)Cl)S(N)(=O)=O Chemical compound C(=O)(O)C1=C(N)C=C(C(=C1)Cl)S(N)(=O)=O KYMYXNHLTLXRFO-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- PEVJJRDDXKCISU-UHFFFAOYSA-N P(Cl)(Cl)(Cl)(Cl)Cl.[P] Chemical compound P(Cl)(Cl)(Cl)(Cl)Cl.[P] PEVJJRDDXKCISU-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N Pseudoisatin Natural products C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B13/00—Dowels or other devices fastened in walls or the like by inserting them in holes made therein for that purpose
- F16B13/04—Dowels or other devices fastened in walls or the like by inserting them in holes made therein for that purpose with parts gripping in the hole or behind the reverse side of the wall after inserting from the front
- F16B13/06—Dowels or other devices fastened in walls or the like by inserting them in holes made therein for that purpose with parts gripping in the hole or behind the reverse side of the wall after inserting from the front combined with expanding sleeve
- F16B13/063—Dowels or other devices fastened in walls or the like by inserting them in holes made therein for that purpose with parts gripping in the hole or behind the reverse side of the wall after inserting from the front combined with expanding sleeve by the use of an expander
- F16B13/066—Dowels or other devices fastened in walls or the like by inserting them in holes made therein for that purpose with parts gripping in the hole or behind the reverse side of the wall after inserting from the front combined with expanding sleeve by the use of an expander fastened by extracting a separate expander-part, actuated by the screw, nail or the like
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B13/00—Dowels or other devices fastened in walls or the like by inserting them in holes made therein for that purpose
Landscapes
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Joining Of Building Structures In Genera (AREA)
- Dowels (AREA)
- Springs (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2141079 | 1971-08-17 | ||
| DE2145918 | 1971-09-14 | ||
| DE2162255 | 1971-12-15 | ||
| DE2164587 | 1971-12-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO130549B true NO130549B (ja) | 1974-09-23 |
| NO130549C NO130549C (ja) | 1975-01-08 |
Family
ID=27431307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2931/72A NO130549C (ja) | 1971-08-17 | 1972-08-16 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3837257A (ja) |
| JP (1) | JPS4831358A (ja) |
| AT (1) | AT315446B (ja) |
| BE (1) | BE786909A (ja) |
| CA (1) | CA958263A (ja) |
| CH (1) | CH544235A (ja) |
| CS (1) | CS161058B2 (ja) |
| DD (1) | DD98556A5 (ja) |
| DK (1) | DK133312C (ja) |
| FR (1) | FR2150119A5 (ja) |
| GB (1) | GB1376524A (ja) |
| IE (1) | IE36869B1 (ja) |
| IL (1) | IL39893A (ja) |
| IT (1) | IT964030B (ja) |
| NL (1) | NL157086B (ja) |
| NO (1) | NO130549C (ja) |
| PL (1) | PL82680B1 (ja) |
| RO (1) | RO61294A (ja) |
| SE (1) | SE382096B (ja) |
| YU (1) | YU34602B (ja) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3968721A (en) * | 1971-08-17 | 1976-07-13 | Artur Fischer | Expansion anchor with safety feature |
| DE2326713C3 (de) * | 1973-05-25 | 1975-11-13 | Artur 7241 Tumlingen Fischer | Befestigungselement zur Befestigung von Bauteilen an einer Wand o.dgl |
| US4065996A (en) * | 1973-06-09 | 1978-01-03 | Artur Fischer | Anchoring device for use in masonry and like structures |
| NL7402180A (nl) * | 1974-06-14 | 1975-08-20 | Maechtle Fritz | Spreidbare plug. |
| GB1504962A (en) * | 1975-02-14 | 1978-03-22 | Dom Holdings Ltd | Expanding bolt-like fastening means |
| GB2132730B (en) * | 1982-12-21 | 1987-02-18 | Noel Lecourt | Improvements relating to expansion bolts |
| AT378044B (de) * | 1983-10-05 | 1985-06-10 | Reimoser Fritz | Zum einsatz in ein loch bestimmter schraubanker |
| CN103161805A (zh) * | 2011-12-09 | 2013-06-19 | 贵州大奥博科技开发有限公司 | 一种膨胀螺栓的制作方法及弹簧式膨胀螺栓 |
| KR20160071424A (ko) * | 2013-10-16 | 2016-06-21 | 알리스 에코 에이알케이 코. 엘티디. | 전기 자동차의 배터리 접촉을 위한 확동 고정 확인 방법즘 |
| WO2021255857A1 (ja) * | 2020-06-17 | 2021-12-23 | イイファス株式会社 | 耐震アンカーおよびその施工方法ならびに締結構造体 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1395453A (en) * | 1921-11-01 | Fastening device | ||
| US570786A (en) * | 1896-11-03 | Expansion-bolt | ||
| US768283A (en) * | 1903-12-07 | 1904-08-23 | Jenkins Mfg Company | Expansion-bolt. |
| US1120409A (en) * | 1912-02-08 | 1914-12-08 | Booraem & Rohmer Patent Company | Expansion-bolt. |
| US1201496A (en) * | 1912-12-09 | 1916-10-17 | Ralph S Peirce | Anchor-bolt. |
| US1352200A (en) * | 1917-08-20 | 1920-09-07 | Orsbee Co Inc | Bolt-anchor |
| US1852297A (en) * | 1931-09-28 | 1932-04-05 | Rawlplug Company Inc | Bolt anchor |
| AT239505B (de) * | 1961-11-20 | 1965-04-12 | Werner Dipl Ing Rein | Expansionsdübel |
| US3202034A (en) * | 1963-01-18 | 1965-08-24 | John J Korenchan | Bolt anchorage with loosening preventing means |
| GB1095402A (ja) * | 1964-02-17 | |||
| AT249955B (de) * | 1964-04-10 | 1966-10-25 | Hubert Stadlbauer | Vorrichtung zum Austrocknen und Trockenhalten von Mauerwerk |
-
1972
- 1972-07-12 IL IL39893A patent/IL39893A/en unknown
- 1972-07-20 AT AT627072A patent/AT315446B/de not_active IP Right Cessation
- 1972-07-25 GB GB3475572A patent/GB1376524A/en not_active Expired
- 1972-07-27 YU YU1953/72A patent/YU34602B/xx unknown
- 1972-07-28 BE BE786909A patent/BE786909A/xx unknown
- 1972-08-05 CA CA149,443A patent/CA958263A/en not_active Expired
- 1972-08-11 SE SE7210486A patent/SE382096B/xx unknown
- 1972-08-11 CS CS5609A patent/CS161058B2/cs unknown
- 1972-08-11 IE IE1118/72A patent/IE36869B1/xx unknown
- 1972-08-15 DD DD165069A patent/DD98556A5/xx unknown
- 1972-08-15 US US00280885A patent/US3837257A/en not_active Expired - Lifetime
- 1972-08-15 PL PL1972157297A patent/PL82680B1/pl unknown
- 1972-08-15 DK DK402772A patent/DK133312C/da active
- 1972-08-16 FR FR7229263A patent/FR2150119A5/fr not_active Expired
- 1972-08-16 CH CH1211372A patent/CH544235A/de not_active IP Right Cessation
- 1972-08-16 NL NL7211205.A patent/NL157086B/xx unknown
- 1972-08-16 NO NO2931/72A patent/NO130549C/no unknown
- 1972-08-17 RO RO71980A patent/RO61294A/ro unknown
- 1972-08-17 JP JP47082445A patent/JPS4831358A/ja active Pending
- 1972-08-17 IT IT28240/72A patent/IT964030B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| NO130549C (ja) | 1975-01-08 |
| IL39893A0 (en) | 1972-09-28 |
| DD98556A5 (ja) | 1973-06-20 |
| RO61294A (ja) | 1976-12-15 |
| GB1376524A (en) | 1974-12-04 |
| DK133312C (da) | 1976-09-27 |
| PL82680B1 (ja) | 1975-10-31 |
| YU195372A (en) | 1979-04-30 |
| CA958263A (en) | 1974-11-26 |
| IL39893A (en) | 1974-11-29 |
| DK133312B (da) | 1976-04-26 |
| NL7211205A (ja) | 1973-02-20 |
| IE36869L (en) | 1973-02-17 |
| AT315446B (de) | 1974-05-27 |
| US3837257A (en) | 1974-09-24 |
| CS161058B2 (ja) | 1975-05-04 |
| NL157086B (nl) | 1978-06-15 |
| IE36869B1 (en) | 1977-03-16 |
| JPS4831358A (ja) | 1973-04-24 |
| AU4469372A (en) | 1973-05-24 |
| YU34602B (en) | 1979-10-31 |
| SE382096B (sv) | 1976-01-12 |
| BE786909A (fr) | 1972-11-16 |
| FR2150119A5 (ja) | 1973-03-30 |
| CH544235A (de) | 1973-11-15 |
| IT964030B (it) | 1974-01-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2910488A (en) | Aniline derivatives | |
| US4327222A (en) | 3,4-Diarylisoxazol-5-acetic acids and process for making same | |
| NO760003L (ja) | ||
| US3303199A (en) | Certain imidazolone derivatives and process for making same | |
| NO130549B (ja) | ||
| US4076709A (en) | Thienothiazines | |
| DK149230B (da) | Analogifremgangsmaade til fremstilling af 5-benzoyl-6-hydroxy-indan-1-carboxylsyrederivater eller farmaceutisk acceptable salte deraf | |
| US2489236A (en) | Synthesis of biotin and related compounds | |
| US2952680A (en) | Derivatives of x-quevazolone | |
| Gilman et al. | The Metalation of Phenothiazine1 | |
| DK175838B1 (da) | Fremgangsmåde til fremstilling af 2,6-dichlordiphenylamineddikesyrederivater | |
| US4127585A (en) | Isoxazol amides of 4-hydroxy-6H-thieno[2,3-b]thiopyran-5-carboxylic acid-7,7-dioxide | |
| US3839325A (en) | Synthesis of 4-sulfonamidophenyl hydrazines | |
| US4261997A (en) | 4-Alkyl-pyrazolo[5,1-b]-quinazolin-9(4H)-ones and anti-allergic compositions containing them | |
| US4007203A (en) | 4-(1-Pyrolidenyl)-2H-1-benzothiopyran-3-carboxanilide | |
| US4046778A (en) | Processes for the preparation of 4-hydroxy-2H-1-benzothiopyran-3-carboxamide 1,1-dioxides | |
| NO135785B (ja) | ||
| US4247555A (en) | 4,9-Dihydro-9-oxo-N-1H-tetrazol-5-yl-pyrazolo[5,1-b]-quinazoline-2-carboxamides and antiallergic compositions and methods using them | |
| US3833608A (en) | Indole-3-methanesulfonamides | |
| US2839529A (en) | Isothiazole compounds | |
| NO135092B (ja) | ||
| NO132234B (ja) | ||
| JPS5811878B2 (ja) | フロ （ ３ ２−ｂ ） インド−ルルイノ セイホウ | |
| US3983126A (en) | Aryloxy pyridine carboxylic-4-acids | |
| US3378592A (en) | Process for the production of 3, 4-dihydroxybenzyloxyaminehydrobromide |