DK170332B1 - Farmakologisk aktive substituerede benzamider, fremgangsmåde til fremstilling deraf og et farmaceutisk præparat heraf - Google Patents
Farmakologisk aktive substituerede benzamider, fremgangsmåde til fremstilling deraf og et farmaceutisk præparat heraf Download PDFInfo
- Publication number
- DK170332B1 DK170332B1 DK291385A DK291385A DK170332B1 DK 170332 B1 DK170332 B1 DK 170332B1 DK 291385 A DK291385 A DK 291385A DK 291385 A DK291385 A DK 291385A DK 170332 B1 DK170332 B1 DK 170332B1
- Authority
- DK
- Denmark
- Prior art keywords
- amino
- chloro
- ethyl
- diethylamino
- compound
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 25
- 150000003936 benzamides Chemical class 0.000 title claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 7
- 229940054066 benzamide antipsychotics Drugs 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims description 147
- 239000000460 chlorine Substances 0.000 claims description 109
- -1 oxo-substituted oxazolidinyl Chemical group 0.000 claims description 79
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 55
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 206010047700 Vomiting Diseases 0.000 claims description 25
- 239000002111 antiemetic agent Substances 0.000 claims description 24
- 229910021529 ammonia Inorganic materials 0.000 claims description 21
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 19
- 239000012312 sodium hydride Substances 0.000 claims description 19
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 230000003474 anti-emetic effect Effects 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 230000030135 gastric motility Effects 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 230000001771 impaired effect Effects 0.000 claims description 3
- 229960000649 oxyphenbutazone Drugs 0.000 claims description 3
- CNDQSXOVEQXJOE-UHFFFAOYSA-N oxyphenbutazone hydrate Chemical compound O.O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 CNDQSXOVEQXJOE-UHFFFAOYSA-N 0.000 claims description 3
- 125000005544 phthalimido group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 claims description 2
- XWXSUOFPQBJJNG-UHFFFAOYSA-N 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-(2,2-dimethoxyethoxy)benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OCC(OC)OC XWXSUOFPQBJJNG-UHFFFAOYSA-N 0.000 claims description 2
- GATCOSFCYSJURA-UHFFFAOYSA-N 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-(2-hydroxypropoxy)benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OCC(C)O GATCOSFCYSJURA-UHFFFAOYSA-N 0.000 claims description 2
- ZVPMWLYIHMIYJK-UHFFFAOYSA-N 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-(2-methoxyethoxymethoxy)benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OCOCCOC ZVPMWLYIHMIYJK-UHFFFAOYSA-N 0.000 claims description 2
- WQDSYTGTSMCTOH-UHFFFAOYSA-N 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-(2-methylsulfinylethoxy)benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OCCS(C)=O WQDSYTGTSMCTOH-UHFFFAOYSA-N 0.000 claims description 2
- DNUXEPOFXIMCGB-UHFFFAOYSA-N 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-[2-(methylamino)-2-oxoethoxy]benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OCC(=O)NC DNUXEPOFXIMCGB-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- JYSBWWBKJZCBFN-UHFFFAOYSA-N 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-(2-hydroxyethoxy)benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OCCO JYSBWWBKJZCBFN-UHFFFAOYSA-N 0.000 claims 1
- NZOKUUUJIFFZKA-UHFFFAOYSA-N 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-(oxolan-2-ylmethoxy)benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OCC1OCCC1 NZOKUUUJIFFZKA-UHFFFAOYSA-N 0.000 claims 1
- SBQNXJKQGLWJLB-UHFFFAOYSA-N 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-[2-(2-methoxyethoxy)ethoxy]benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OCCOCCOC SBQNXJKQGLWJLB-UHFFFAOYSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 219
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 141
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- 239000000203 mixture Substances 0.000 description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 80
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- 229910001868 water Inorganic materials 0.000 description 75
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
- 238000004458 analytical method Methods 0.000 description 67
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- 239000000243 solution Substances 0.000 description 64
- 239000007787 solid Substances 0.000 description 49
- 239000002904 solvent Substances 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 33
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 30
- HPSMMIJTHMWCGC-UHFFFAOYSA-N 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-hydroxybenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1O HPSMMIJTHMWCGC-UHFFFAOYSA-N 0.000 description 29
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
- 239000000725 suspension Substances 0.000 description 27
- 238000012360 testing method Methods 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 24
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 21
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- 239000003921 oil Substances 0.000 description 16
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 229940125683 antiemetic agent Drugs 0.000 description 12
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 12
- 229960004046 apomorphine Drugs 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000284 extract Substances 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 230000002640 gastrokinetic effect Effects 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 239000003210 dopamine receptor blocking agent Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 229960000581 salicylamide Drugs 0.000 description 8
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 7
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- ZGNIYAPHJAPRMA-UHFFFAOYSA-N chlorine azide Chemical compound ClN=[N+]=[N-] ZGNIYAPHJAPRMA-UHFFFAOYSA-N 0.000 description 7
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 7
- 229960004316 cisplatin Drugs 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- 239000002246 antineoplastic agent Substances 0.000 description 6
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- 230000008025 crystallization Effects 0.000 description 6
- 229940127089 cytotoxic agent Drugs 0.000 description 6
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 6
- 230000003291 dopaminomimetic effect Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 229960004503 metoclopramide Drugs 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
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- 230000008485 antagonism Effects 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
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- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 5
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- JXIGWAINVIWPQD-UHFFFAOYSA-N 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-hydroxybenzamide;hydrochloride Chemical compound Cl.CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1O JXIGWAINVIWPQD-UHFFFAOYSA-N 0.000 description 3
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- 241000700199 Cavia porcellus Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- 239000004480 active ingredient Substances 0.000 description 3
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- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 239000002895 emetic Substances 0.000 description 3
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
- C07D233/20—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 substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62574284A | 1984-06-28 | 1984-06-28 | |
| US62574284 | 1984-06-28 | ||
| US06/729,513 US4808624A (en) | 1984-06-28 | 1985-05-06 | Pharmacologically active substituted benzamides |
| US72951385 | 1985-05-06 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK291385D0 DK291385D0 (da) | 1985-06-27 |
| DK291385A DK291385A (da) | 1985-12-29 |
| DK170332B1 true DK170332B1 (da) | 1995-08-07 |
Family
ID=27090001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK291385A DK170332B1 (da) | 1984-06-28 | 1985-06-27 | Farmakologisk aktive substituerede benzamider, fremgangsmåde til fremstilling deraf og et farmaceutisk præparat heraf |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4808624A (de) |
| KR (1) | KR920000270B1 (de) |
| AR (1) | AR244677A1 (de) |
| AT (1) | AT394363B (de) |
| AU (1) | AU592759B2 (de) |
| BE (1) | BE902760A (de) |
| CH (1) | CH663954A5 (de) |
| CY (1) | CY1597A (de) |
| DE (1) | DE3523076C2 (de) |
| DK (1) | DK170332B1 (de) |
| ES (5) | ES8609218A1 (de) |
| FI (1) | FI83768C (de) |
| FR (1) | FR2566773B1 (de) |
| GB (1) | GB2160871B (de) |
| GR (1) | GR851576B (de) |
| HK (1) | HK50991A (de) |
| HU (1) | HU195475B (de) |
| IE (1) | IE58705B1 (de) |
| IL (1) | IL75621A (de) |
| IT (1) | IT1200657B (de) |
| LU (1) | LU85978A1 (de) |
| MY (1) | MY102080A (de) |
| NL (1) | NL8501856A (de) |
| NO (1) | NO169485C (de) |
| NZ (1) | NZ212499A (de) |
| PT (1) | PT80731B (de) |
| SE (1) | SE502926C2 (de) |
| SG (1) | SG41691G (de) |
| YU (1) | YU45726B (de) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH653670A5 (de) * | 1983-03-03 | 1986-01-15 | Hoffmann La Roche | Benzamid-derivate. |
| US4820715A (en) * | 1984-06-28 | 1989-04-11 | Bristol-Myers Company | Anti-emetic quinuclidinyl benzamides |
| US4772630A (en) * | 1984-11-23 | 1988-09-20 | Ciba-Geigy Corp. | Benzamides and their salts |
| FI871447A (fi) * | 1986-04-07 | 1987-10-08 | Bristol Myers Co | Stabila injicerbara antivomitiva kompositioner. |
| US4882356A (en) * | 1987-03-10 | 1989-11-21 | Nassar Munir N | Stable injectable antiemetic compositions |
| US4772459A (en) * | 1986-09-09 | 1988-09-20 | Erbamont, Inc. | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein |
| FR2618149B1 (fr) * | 1987-07-16 | 1989-09-22 | Synthelabo | Derives de n-aminoalkyl n-phenyl arylamides, leur preparation et leur application en therapeutique |
| GB8718346D0 (en) * | 1987-08-03 | 1987-09-09 | Fordonal Sa | Substituted benzamides |
| GB8718345D0 (en) * | 1987-08-03 | 1987-09-09 | Fordonal Sa | N-substituted benzamides |
| IT1216120B (it) * | 1988-03-17 | 1990-02-22 | Poli Ind Chimica Spa | Derivati n_cicloalchilaminoetilbenzamidici, loro preparazione e composizioni farmaceutiche che li contengono. |
| US5374637A (en) * | 1989-03-22 | 1994-12-20 | Janssen Pharmaceutica N.V. | N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives |
| US5126343A (en) * | 1989-09-11 | 1992-06-30 | G. D. Searle & Co. | N-azabicyclo [3.3.0]octane amides of aromatic acids |
| GB9005014D0 (en) * | 1990-03-06 | 1990-05-02 | Janssen Pharmaceutica Nv | N.(4.piperidinyl)(dihydrobenzofuran or dihydro.2h.benzopyran)carboxamide derivatives |
| US5395832A (en) * | 1991-02-15 | 1995-03-07 | Hokuriku Seiyaku Co., Ltd. | Benzamide derivatives |
| CA2074061A1 (en) * | 1991-08-26 | 1993-02-27 | Ivo Monkovic | Benzamide multidrug resistance reversing agents |
| US5723103A (en) * | 1994-12-09 | 1998-03-03 | Vanderbilt University | Substituted benzamides and radioligand analogs and methods of use |
| JP3933244B2 (ja) * | 1997-04-04 | 2007-06-20 | 株式会社資生堂 | アルキレンジアミン誘導体及び抗潰瘍剤、抗菌剤 |
| EP2253316B1 (de) | 2009-05-20 | 2013-08-14 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Serotonin-5-HT3-Rezeptorantagonisten zur Verwendung bei der Behandlung oder Prävention einer Innenohr-Pathologie mit Vestibularisdefiziten |
| KR101779991B1 (ko) | 2009-05-20 | 2017-09-19 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 병소성 전정 질환을 치료하기 위한 세로토닌 5-ｈｔ3 수용체 길항제의 용도 |
| KR101641836B1 (ko) | 2015-06-25 | 2016-07-22 | (주)유경 | 세균방지를 위한 복수형 우유냉각장치 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1139272A (fr) * | 1954-06-29 | 1957-06-27 | Thomae Gmbh Dr K | Perfectionnements apportés aux procédés pour fabriquer des dérivés de l'acide benzoïque |
| DE1078581B (de) * | 1958-03-15 | 1960-03-31 | Riedel De Haeen Ag | Verfahren zur Herstellung von 1, 3-Dioxolanyl-(4)-methylaethern von o-Vanillinsaeureamiden |
| FR1526M (fr) * | 1961-07-25 | 1962-10-15 | Ile De France | Nouveaux médicaments antiémétiques. |
| NL281394A (de) * | 1961-07-25 | |||
| FR1525M (fr) * | 1961-07-25 | 1962-11-16 | Ile De France | Médicaments antiémétiques nouveaux. |
| FR1407055A (fr) * | 1963-03-05 | 1965-07-30 | Ile De France | Nouveau procédé de préparation de benzamides substitués |
| GB1019781A (de) * | 1963-03-05 | |||
| GB1047028A (en) * | 1963-11-15 | 1966-11-02 | Rech S Et D Applic Scient Et M | Improvements in or relating to 5-acetamido-salicylamide derivatives |
| ES336000A1 (es) * | 1966-01-22 | 1968-04-01 | Ile De France | Nuevo procedimiento de preparacion de 2-alcoxi-5-halogeno- benzamidas n-aminoalquil sustituidas. |
| CH505850A (de) * | 1968-03-21 | 1971-04-15 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Benzoxazepinonen |
| US3891671A (en) * | 1968-08-01 | 1975-06-24 | Ile De France | N-(2-pyrrolidyl or piperidyl alkyl)-4-hydroxy benzamides |
| CA988534A (en) * | 1969-02-26 | 1976-05-04 | John Krapcho | Benzamide derivatives and processes for their manufacture |
| FR2313935A1 (fr) * | 1975-06-10 | 1977-01-07 | Ile De France | Nouveaux benzamides substitues, leurs derives et leur procede de preparation |
| US3963745A (en) * | 1972-04-03 | 1976-06-15 | A. H. Robins Company, Incorporated | Method for controlling emesis with N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides |
| US3966957A (en) * | 1972-04-03 | 1976-06-29 | A. H. Robins Company, Incorporated | Method for controlling emesis with N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides |
| FR2277815A1 (fr) * | 1972-06-20 | 1976-02-06 | Ile De France | Nouveau procede de preparation du n(diethylaminoethyl) 2-methoxy 4-amino 5-chlorobenzamide |
| FR2281353A1 (fr) * | 1972-06-22 | 1976-03-05 | Ile De France | Nouveau procede de preparation du n(diethylaminoethyl) 2-methoxy 4-amino 5-chlorobenzamide |
| JPS4969627A (de) * | 1972-10-31 | 1974-07-05 | ||
| JPS5035125A (de) * | 1973-07-24 | 1975-04-03 | ||
| FR2243933B1 (de) * | 1973-09-17 | 1978-06-30 | Ile De France | |
| JPS5126840A (en) * | 1974-08-26 | 1976-03-05 | Ile De France | Nn jiarukiruaminoarukiru 22 arukokishi 44 chikan 55 harobenzuamido no seizoho |
| GB1574418A (en) * | 1976-11-16 | 1980-09-03 | Anphar Sa | Piperidine derivatives |
| DE2721643A1 (de) * | 1977-05-13 | 1978-11-23 | Heumann Ludwig & Co Gmbh | Verfahren zur herstellung von eckige klammer auf n,n-dialkylamino-alkyl eckige klammer zu -2-alkoxy-5-sulfamoylbenzamiden |
| US4207327A (en) * | 1977-08-19 | 1980-06-10 | A. H. Robins Company, Inc. | N-(4-Pyrazolidinyl)benzamides and their amino precursors |
| CA1183847A (en) * | 1981-10-01 | 1985-03-12 | Georges Van Daele | N-(3-hydroxy-4-piperidinyl)benzamide derivatives |
-
1985
- 1985-05-06 US US06/729,513 patent/US4808624A/en not_active Expired - Fee Related
- 1985-06-20 YU YU107085A patent/YU45726B/sh unknown
- 1985-06-20 NZ NZ212499A patent/NZ212499A/xx unknown
- 1985-06-25 ES ES544527A patent/ES8609218A1/es not_active Expired
- 1985-06-25 IL IL75621A patent/IL75621A/xx not_active IP Right Cessation
- 1985-06-25 FI FI852512A patent/FI83768C/fi not_active IP Right Cessation
- 1985-06-26 CH CH2710/85A patent/CH663954A5/de not_active IP Right Cessation
- 1985-06-26 AR AR85300807A patent/AR244677A1/es active
- 1985-06-26 NO NO852561A patent/NO169485C/no unknown
- 1985-06-27 FR FR858509816A patent/FR2566773B1/fr not_active Expired
- 1985-06-27 DE DE3523076A patent/DE3523076C2/de not_active Expired - Fee Related
- 1985-06-27 BE BE0/215265A patent/BE902760A/fr not_active IP Right Cessation
- 1985-06-27 IE IE162385A patent/IE58705B1/en not_active IP Right Cessation
- 1985-06-27 LU LU85978A patent/LU85978A1/fr unknown
- 1985-06-27 NL NL8501856A patent/NL8501856A/nl not_active Application Discontinuation
- 1985-06-27 KR KR1019850004574A patent/KR920000270B1/ko not_active IP Right Cessation
- 1985-06-27 HU HU852515A patent/HU195475B/hu not_active IP Right Cessation
- 1985-06-27 DK DK291385A patent/DK170332B1/da not_active IP Right Cessation
- 1985-06-27 GR GR851576A patent/GR851576B/el unknown
- 1985-06-27 SE SE8503207A patent/SE502926C2/sv not_active IP Right Cessation
- 1985-06-27 IT IT21325/85A patent/IT1200657B/it active
- 1985-06-27 GB GB08516320A patent/GB2160871B/en not_active Expired
- 1985-06-27 PT PT80731A patent/PT80731B/pt not_active IP Right Cessation
- 1985-06-27 AU AU44242/85A patent/AU592759B2/en not_active Ceased
- 1985-06-28 AT AT0193185A patent/AT394363B/de not_active IP Right Cessation
-
1986
- 1986-01-29 ES ES551393A patent/ES8705852A1/es not_active Expired
- 1986-09-16 ES ES557076A patent/ES8801190A1/es not_active Expired
-
1987
- 1987-01-30 ES ES557365A patent/ES8801192A1/es not_active Expired
- 1987-01-30 ES ES557364A patent/ES8801191A1/es not_active Expired
- 1987-09-29 MY MYPI87002214A patent/MY102080A/en unknown
-
1991
- 1991-06-03 SG SG416/91A patent/SG41691G/en unknown
- 1991-07-04 HK HK509/91A patent/HK50991A/xx unknown
-
1992
- 1992-04-03 CY CY1597A patent/CY1597A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |