NO833024L - Benzamid-derivater - Google Patents
Benzamid-derivaterInfo
- Publication number
- NO833024L NO833024L NO833024A NO833024A NO833024L NO 833024 L NO833024 L NO 833024L NO 833024 A NO833024 A NO 833024A NO 833024 A NO833024 A NO 833024A NO 833024 L NO833024 L NO 833024L
- Authority
- NO
- Norway
- Prior art keywords
- group
- benzamide
- general formula
- imidazol
- integer
- Prior art date
Links
- 150000003936 benzamides Chemical class 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 67
- 239000007858 starting material Substances 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 27
- -1 hydroxy, mercapto, amino Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000007787 solid Substances 0.000 description 65
- 239000000243 solution Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 14
- UYEGPRQCGATDAO-UHFFFAOYSA-N 2-amino-n-(3-imidazol-1-ylpropyl)benzamide Chemical compound NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 UYEGPRQCGATDAO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 210000004369 blood Anatomy 0.000 description 10
- 239000008280 blood Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241000416162 Astragalus gummifer Species 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229920001615 Tragacanth Polymers 0.000 description 9
- 230000037396 body weight Effects 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 235000010487 tragacanth Nutrition 0.000 description 9
- 239000000196 tragacanth Substances 0.000 description 9
- 229940116362 tragacanth Drugs 0.000 description 9
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 235000021395 porridge Nutrition 0.000 description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 206010012601 diabetes mellitus Diseases 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- AKSHYZIVQLGDII-UHFFFAOYSA-N 2-amino-5-chloro-n-(3-imidazol-1-ylpropyl)benzamide Chemical compound NC1=CC=C(Cl)C=C1C(=O)NCCCN1C=NC=C1 AKSHYZIVQLGDII-UHFFFAOYSA-N 0.000 description 6
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- RSISPWUDHVHDMZ-UHFFFAOYSA-N 2-[(4-chlorophenyl)sulfonylamino]-n-(3-imidazol-1-ylpropyl)benzamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 RSISPWUDHVHDMZ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000008247 solid mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 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 description 3
- QRVDOXHBQHMGIR-UHFFFAOYSA-N 2-amino-n-(2-imidazol-1-ylethyl)benzamide Chemical compound NC1=CC=CC=C1C(=O)NCCN1C=NC=C1 QRVDOXHBQHMGIR-UHFFFAOYSA-N 0.000 description 3
- PWJGGGHELBBRHU-UHFFFAOYSA-N 2-amino-n-[3-(2-methylimidazol-1-yl)propyl]benzamide Chemical compound CC1=NC=CN1CCCNC(=O)C1=CC=CC=C1N PWJGGGHELBBRHU-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004366 Glucose oxidase Substances 0.000 description 3
- 108010015776 Glucose oxidase Proteins 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229940116332 glucose oxidase Drugs 0.000 description 3
- 235000019420 glucose oxidase Nutrition 0.000 description 3
- 230000002218 hypoglycaemic effect Effects 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- XUVPADLCGIQEFF-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-[(4-nitrophenyl)sulfonylamino]benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 XUVPADLCGIQEFF-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 2
- HPXPKDCKBXZIMU-UHFFFAOYSA-N 2-[(4-aminophenyl)sulfonylamino]-n-(3-imidazol-1-ylpropyl)benzamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 HPXPKDCKBXZIMU-UHFFFAOYSA-N 0.000 description 2
- BGMCIDHGUNPPMB-UHFFFAOYSA-N 2-amino-n-(3-imidazol-1-ylbutyl)benzamide Chemical compound C1=CN=CN1C(C)CCNC(=O)C1=CC=CC=C1N BGMCIDHGUNPPMB-UHFFFAOYSA-N 0.000 description 2
- ZFGQAWGLVBLWMS-UHFFFAOYSA-N 2-amino-n-(4-imidazol-1-ylbutyl)benzamide Chemical compound NC1=CC=CC=C1C(=O)NCCCCN1C=NC=C1 ZFGQAWGLVBLWMS-UHFFFAOYSA-N 0.000 description 2
- HQCNOZDDENMOJU-UHFFFAOYSA-N 2-amino-n-[3-(4-methylimidazol-1-yl)propyl]benzamide Chemical compound C1=NC(C)=CN1CCCNC(=O)C1=CC=CC=C1N HQCNOZDDENMOJU-UHFFFAOYSA-N 0.000 description 2
- BTRCVKADYDVSLI-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(S(Cl)(=O)=O)=C1 BTRCVKADYDVSLI-UHFFFAOYSA-N 0.000 description 2
- ONCAZCNPWWQQMW-UHFFFAOYSA-N 3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC(S(Cl)(=O)=O)=C1 ONCAZCNPWWQQMW-UHFFFAOYSA-N 0.000 description 2
- OINWZUJVEXUHCC-UHFFFAOYSA-N 3-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC(S(Cl)(=O)=O)=C1 OINWZUJVEXUHCC-UHFFFAOYSA-N 0.000 description 2
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000012754 cardiac puncture Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- LPUSDWXDDBLMDS-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-[[3-(trifluoromethyl)phenyl]sulfonylamino]benzamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)NC=2C(=CC=CC=2)C(=O)NCCCN2C=NC=C2)=C1 LPUSDWXDDBLMDS-UHFFFAOYSA-N 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- JDAJYNHGBUXIKS-UHFFFAOYSA-N 2,3,4-trichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C(Cl)=C1Cl JDAJYNHGBUXIKS-UHFFFAOYSA-N 0.000 description 1
- PQODWTNHDKDHIW-UHFFFAOYSA-N 2,3-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC(S(Cl)(=O)=O)=C1Cl PQODWTNHDKDHIW-UHFFFAOYSA-N 0.000 description 1
- WNVVRCKTQSCPAC-UHFFFAOYSA-N 2,4,5-trichlorobenzenesulfonyl chloride Chemical compound ClC1=CC(Cl)=C(S(Cl)(=O)=O)C=C1Cl WNVVRCKTQSCPAC-UHFFFAOYSA-N 0.000 description 1
- FDTPBIKNYWQLAE-UHFFFAOYSA-N 2,4-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C(Cl)=C1 FDTPBIKNYWQLAE-UHFFFAOYSA-N 0.000 description 1
- FJSAJUXIHJIAMD-UHFFFAOYSA-N 2,4-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C(F)=C1 FJSAJUXIHJIAMD-UHFFFAOYSA-N 0.000 description 1
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- 230000037213 diet Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
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- MRNJSMNKWNPSDN-UHFFFAOYSA-N ethyl 4-chlorosulfonylbenzoate Chemical compound CCOC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 MRNJSMNKWNPSDN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 230000001125 hyperlipoproteinemic effect Effects 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- GRFFKMQXXAVNMM-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-(methylamino)benzamide Chemical compound CNC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 GRFFKMQXXAVNMM-UHFFFAOYSA-N 0.000 description 1
- XVEVNDQJHFFAFM-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-[(2,3,4-trichlorophenyl)sulfonylamino]benzamide Chemical compound ClC1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 XVEVNDQJHFFAFM-UHFFFAOYSA-N 0.000 description 1
- NDUHEIRGXWLVBQ-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-[(2,4,5-trichlorophenyl)sulfonylamino]benzamide Chemical compound C1=C(Cl)C(Cl)=CC(Cl)=C1S(=O)(=O)NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 NDUHEIRGXWLVBQ-UHFFFAOYSA-N 0.000 description 1
- RBIFHKQYBPHZED-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-[(2-methylphenyl)sulfonylamino]benzamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 RBIFHKQYBPHZED-UHFFFAOYSA-N 0.000 description 1
- NSYNKGOMJBCIPW-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-[(2-nitrophenyl)sulfonylamino]benzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 NSYNKGOMJBCIPW-UHFFFAOYSA-N 0.000 description 1
- JLNIJWARNPYQDY-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-[(3-nitrophenyl)sulfonylamino]benzamide Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)NC=2C(=CC=CC=2)C(=O)NCCCN2C=NC=C2)=C1 JLNIJWARNPYQDY-UHFFFAOYSA-N 0.000 description 1
- BTCANVPQQHIFHW-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-[(4-methoxyphenyl)sulfonylamino]benzamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 BTCANVPQQHIFHW-UHFFFAOYSA-N 0.000 description 1
- CABPJJLXQXXVDC-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-[(4-octylphenyl)sulfonylamino]benzamide Chemical compound C1=CC(CCCCCCCC)=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 CABPJJLXQXXVDC-UHFFFAOYSA-N 0.000 description 1
- KFMMLTAIJWNREO-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-[(4-propan-2-ylphenyl)sulfonylamino]benzamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 KFMMLTAIJWNREO-UHFFFAOYSA-N 0.000 description 1
- RTEFFPAPKVIDTJ-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-[[2-(trifluoromethyl)phenyl]sulfonylamino]benzamide Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 RTEFFPAPKVIDTJ-UHFFFAOYSA-N 0.000 description 1
- RNZWGMCSFKDKJK-UHFFFAOYSA-N n-[3-(4-methylimidazol-1-yl)propyl]-2-[(4-nitrophenyl)sulfonylamino]benzamide Chemical compound C1=NC(C)=CN1CCCNC(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 RNZWGMCSFKDKJK-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- C07D233/54—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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8224296 | 1982-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO833024L true NO833024L (no) | 1984-02-24 |
Family
ID=10532494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO833024A NO833024L (no) | 1982-08-24 | 1983-08-22 | Benzamid-derivater |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4507315A (de) |
| JP (1) | JPS5955873A (de) |
| KR (1) | KR840005717A (de) |
| AT (1) | ATA301083A (de) |
| AU (1) | AU1818083A (de) |
| BE (1) | BE897580A (de) |
| CA (1) | CA1195993A (de) |
| CS (1) | CS240973B2 (de) |
| DE (1) | DE3330403A1 (de) |
| DK (1) | DK386783A (de) |
| ES (2) | ES525099A0 (de) |
| FI (1) | FI832989A (de) |
| FR (1) | FR2532310B1 (de) |
| GB (1) | GB2126225B (de) |
| GR (1) | GR78673B (de) |
| IL (1) | IL69544A0 (de) |
| IT (1) | IT1169775B (de) |
| LU (1) | LU84974A1 (de) |
| NL (1) | NL8302947A (de) |
| NO (1) | NO833024L (de) |
| PT (1) | PT77219B (de) |
| SE (1) | SE8304545L (de) |
| ZA (1) | ZA836191B (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0625144B2 (ja) * | 1986-02-24 | 1994-04-06 | 四国化成工業株式会社 | 新規イミダゾール化合物及び該化合物の合成方法 |
| US4916145A (en) * | 1987-07-10 | 1990-04-10 | Hoffmann-La Roche Inc. | Substituted n-[(pyridyl)alkyl]aryl-carboxamide |
| US4886629A (en) * | 1988-06-06 | 1989-12-12 | Allied-Signal Inc. | Process for the preparation of fluorinated benzene sulfonyl fluorides |
| CA2057324A1 (en) * | 1990-12-18 | 1992-06-19 | Lora Louise Fitch | Benzamide and sulfonamide hypoglycemic agents |
| US6503935B1 (en) | 1998-08-07 | 2003-01-07 | Abbott Laboratories | Imidazoles and related compounds as α1A agonists |
| EP1196385A1 (de) * | 1999-07-06 | 2002-04-17 | Vertex Pharmaceuticals Incorporated | Beta-aminosäure derivate zur behandlung von neurologischen krankheiten |
| DE10121003A1 (de) * | 2001-04-28 | 2002-12-19 | Aventis Pharma Gmbh | Anthranilsäureamide, Verfahren zur Herstellung, ihrer Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| US7297816B2 (en) | 2004-09-24 | 2007-11-20 | Janssen Pharmaceutica N.V. | Sulfonamide compounds |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3349124A (en) * | 1957-05-20 | 1967-10-24 | Pfizer & Co C | Oral antidiabetic agent |
| BE756062A (fr) * | 1969-09-11 | 1971-03-11 | Boehringer Sohn Ingelheim | Derives de 1,1,1-trichlorethane leurs procedes de fabrication et leur utilisation en tant que substances biocides |
| DE2500157C2 (de) * | 1975-01-03 | 1983-09-15 | Hoechst Ag, 6230 Frankfurt | N-Acyl-4-(2-aminoäthyl)-benzoesäuren, deren Salze und Ester, Verfahren zu deren Herstellung und deren Verwendung |
| DK148576A (da) * | 1975-04-18 | 1976-10-19 | Boehringer Mannheim Gmbh | Fenylalkankarbonsyrederivater og fremgangsmade til deres fremstilling |
| DE2517229A1 (de) * | 1975-04-18 | 1976-10-28 | Boehringer Mannheim Gmbh | Phenylalkylcarbonsaeure-derivate und verfahren zu ihrer herstellung |
| US4317915A (en) * | 1976-08-23 | 1982-03-02 | Hoffmann-La Roche Inc. | Novel thiophene derivatives |
| NZ186175A (en) * | 1977-01-27 | 1980-03-05 | Shionogi & Co | Meta-sulphonamidobenzamide derivatives |
| US4245120A (en) * | 1977-09-27 | 1981-01-13 | American Cyanamid Company | 4-(Monoalkylamino)benzene polycarboxylic acids |
| LU79008A1 (de) * | 1978-02-03 | 1979-09-06 | Byk Gulden Lomberg Chem Fab | W-(n-alkyl-n-benzoyl-amino)-phenylalkansaeuren,ihre verwendung und herstellung sowie sie enthaltende arzneimittel |
-
1983
- 1983-08-18 PT PT77219A patent/PT77219B/pt unknown
- 1983-08-22 GB GB08322539A patent/GB2126225B/en not_active Expired
- 1983-08-22 GR GR72271A patent/GR78673B/el unknown
- 1983-08-22 JP JP58151746A patent/JPS5955873A/ja active Pending
- 1983-08-22 KR KR1019830003923A patent/KR840005717A/ko not_active Application Discontinuation
- 1983-08-22 SE SE8304545A patent/SE8304545L/xx not_active Application Discontinuation
- 1983-08-22 CS CS836124A patent/CS240973B2/cs unknown
- 1983-08-22 ZA ZA836191A patent/ZA836191B/xx unknown
- 1983-08-22 AU AU18180/83A patent/AU1818083A/en not_active Abandoned
- 1983-08-22 NO NO833024A patent/NO833024L/no unknown
- 1983-08-22 FI FI832989A patent/FI832989A/fi not_active Application Discontinuation
- 1983-08-22 IL IL69544A patent/IL69544A0/xx unknown
- 1983-08-22 US US06/525,503 patent/US4507315A/en not_active Expired - Fee Related
- 1983-08-23 LU LU84974A patent/LU84974A1/fr unknown
- 1983-08-23 AT AT833010A patent/ATA301083A/de not_active Application Discontinuation
- 1983-08-23 CA CA000435172A patent/CA1195993A/en not_active Expired
- 1983-08-23 FR FR8313590A patent/FR2532310B1/fr not_active Expired
- 1983-08-23 DK DK386783A patent/DK386783A/da unknown
- 1983-08-23 DE DE19833330403 patent/DE3330403A1/de not_active Withdrawn
- 1983-08-23 BE BE0/211394A patent/BE897580A/fr not_active IP Right Cessation
- 1983-08-23 ES ES525099A patent/ES525099A0/es active Granted
- 1983-08-23 NL NL8302947A patent/NL8302947A/nl not_active Application Discontinuation
- 1983-08-24 IT IT22629/83A patent/IT1169775B/it active
- 1983-12-13 ES ES528012A patent/ES528012A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FI832989A0 (fi) | 1983-08-22 |
| ZA836191B (en) | 1984-04-25 |
| GB8322539D0 (en) | 1983-09-21 |
| FI832989A (fi) | 1984-02-25 |
| IT8322629A0 (it) | 1983-08-24 |
| BE897580A (fr) | 1984-02-23 |
| GB2126225A (en) | 1984-03-21 |
| CA1195993A (en) | 1985-10-29 |
| GR78673B (de) | 1984-09-27 |
| ES8505935A1 (es) | 1985-06-16 |
| IT1169775B (it) | 1987-06-03 |
| NL8302947A (nl) | 1984-03-16 |
| LU84974A1 (fr) | 1984-03-23 |
| FR2532310B1 (fr) | 1986-01-10 |
| ES528012A0 (es) | 1985-06-16 |
| DK386783A (da) | 1984-02-25 |
| PT77219A (fr) | 1983-09-01 |
| SE8304545D0 (sv) | 1983-08-22 |
| FR2532310A1 (fr) | 1984-03-02 |
| CS240973B2 (en) | 1986-03-13 |
| ES8502691A1 (es) | 1985-01-16 |
| AU1818083A (en) | 1984-03-01 |
| US4507315A (en) | 1985-03-26 |
| DK386783D0 (da) | 1983-08-23 |
| ATA301083A (de) | 1985-11-15 |
| ES525099A0 (es) | 1985-01-16 |
| KR840005717A (ko) | 1984-11-16 |
| JPS5955873A (ja) | 1984-03-31 |
| PT77219B (fr) | 1986-02-04 |
| CS612483A2 (en) | 1985-06-13 |
| IL69544A0 (en) | 1983-11-30 |
| SE8304545L (sv) | 1984-02-25 |
| GB2126225B (en) | 1985-10-09 |
| DE3330403A1 (de) | 1984-03-01 |
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