NO132393B - - Google Patents
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- Publication number
- NO132393B NO132393B NO4829/70A NO482970A NO132393B NO 132393 B NO132393 B NO 132393B NO 4829/70 A NO4829/70 A NO 4829/70A NO 482970 A NO482970 A NO 482970A NO 132393 B NO132393 B NO 132393B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- butoxycarbonyl
- aminooxyacetic
- group
- aminooxy
- Prior art date
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims description 132
- -1 t-butoxycarbonyl group Chemical group 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 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
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 67
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
- 239000000243 solution Substances 0.000 description 63
- 238000004458 analytical method Methods 0.000 description 61
- 150000002168 ethanoic acid esters Chemical class 0.000 description 61
- 229910052757 nitrogen Inorganic materials 0.000 description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 29
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 22
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000012362 glacial acetic acid Substances 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 125000001589 carboacyl group Chemical group 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- QBXODCKYUZNZCY-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]oxyacetic acid Chemical compound CC(C)(C)OC(=O)NOCC(O)=O QBXODCKYUZNZCY-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- IWCNUQZFGIDXFW-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) 2-(phenylmethoxycarbonylaminooxy)acetate Chemical compound ClC1=C(C(=C(C(=C1OC(CONC(=O)OCC1=CC=CC=C1)=O)Cl)Cl)Cl)Cl IWCNUQZFGIDXFW-UHFFFAOYSA-N 0.000 description 6
- PGZITGQTBWPRJM-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]oxyacetate Chemical compound CC(C)(C)OC(=O)NOCC(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl PGZITGQTBWPRJM-UHFFFAOYSA-N 0.000 description 6
- WZQIHEBFGNASFQ-UHFFFAOYSA-N Cl.NOCC(=O)NC1=CC=CC=C1 Chemical compound Cl.NOCC(=O)NC1=CC=CC=C1 WZQIHEBFGNASFQ-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 4
- QCXLIWFAFQEMSZ-UHFFFAOYSA-N CCOC(C=C1)=CC=C1NC(CONC(OCC1=CC=CC=C1)=O)=O Chemical compound CCOC(C=C1)=CC=C1NC(CONC(OCC1=CC=CC=C1)=O)=O QCXLIWFAFQEMSZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000003931 anilides Chemical class 0.000 description 4
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 4
- DHJZFMMLUKUMDQ-UHFFFAOYSA-N 2-(phenylmethoxycarbonylaminooxy)acetic acid Chemical compound OC(=O)CONC(=O)OCC1=CC=CC=C1 DHJZFMMLUKUMDQ-UHFFFAOYSA-N 0.000 description 3
- AWCLSDFQZCGERZ-UHFFFAOYSA-N 2-aminooxy-n-(2-methoxyphenyl)acetamide;hydrochloride Chemical compound Cl.COC1=CC=CC=C1NC(=O)CON AWCLSDFQZCGERZ-UHFFFAOYSA-N 0.000 description 3
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 3
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 3
- YUNBHMYSHAIDRF-UHFFFAOYSA-N C1=CC=C(C=C1)COC(=O)NOCC(=O)NC2=CC=C(C=C2)Cl Chemical compound C1=CC=C(C=C1)COC(=O)NOCC(=O)NC2=CC=C(C=C2)Cl YUNBHMYSHAIDRF-UHFFFAOYSA-N 0.000 description 3
- LVLPDRQXKNDUTH-UHFFFAOYSA-N CC(C)(C)OC(NOCC(NC(C=C1)=CC=C1OC)=O)=O Chemical compound CC(C)(C)OC(NOCC(NC(C=C1)=CC=C1OC)=O)=O LVLPDRQXKNDUTH-UHFFFAOYSA-N 0.000 description 3
- BPRAKIFZEPMLMB-UHFFFAOYSA-N CCC(C=C1)=CC=C1NC(CONC(OC(C)(C)C)=O)=O Chemical compound CCC(C=C1)=CC=C1NC(CONC(OC(C)(C)C)=O)=O BPRAKIFZEPMLMB-UHFFFAOYSA-N 0.000 description 3
- ZLLOVUWGMUGFAF-UHFFFAOYSA-N CCOC(C=C1)=CC=C1NC(CONC(OC(C)(C)C)=O)=O Chemical compound CCOC(C=C1)=CC=C1NC(CONC(OC(C)(C)C)=O)=O ZLLOVUWGMUGFAF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MJRYMQXNUZLKQT-UHFFFAOYSA-N [O-][N+](C(C=C1)=CC=C1NC(CONC(OCC1=CC=CC=C1)=O)=O)=O Chemical compound [O-][N+](C(C=C1)=CC=C1NC(CONC(OCC1=CC=CC=C1)=O)=O)=O MJRYMQXNUZLKQT-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- TXVQDVIQDCCMGY-UHFFFAOYSA-N benzyl N-[2-(N-(2-aminooxyacetyl)anilino)-2-oxoethyl]carbamate Chemical compound C(C1=CC=CC=C1)OC(=O)NCC(=O)N(C1=CC=CC=C1)C(CON)=O TXVQDVIQDCCMGY-UHFFFAOYSA-N 0.000 description 3
- CSPIXHMXQMNKDB-UHFFFAOYSA-N benzyl N-[2-(benzylamino)-2-oxoethoxy]carbamate Chemical compound C(C1=CC=CC=C1)NC(CONC(=O)OCC1=CC=CC=C1)=O CSPIXHMXQMNKDB-UHFFFAOYSA-N 0.000 description 3
- DLQVVVMBWCRUKR-UHFFFAOYSA-N benzyl N-[2-[(4-chlorophenyl)methylamino]-2-oxoethoxy]carbamate Chemical compound ClC1=CC=C(CNC(CONC(=O)OCC2=CC=CC=C2)=O)C=C1 DLQVVVMBWCRUKR-UHFFFAOYSA-N 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- NQRKYASMKDDGHT-UHFFFAOYSA-N (aminooxy)acetic acid Chemical compound NOCC(O)=O NQRKYASMKDDGHT-UHFFFAOYSA-N 0.000 description 2
- SIGWOTBNRFNRQN-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]oxy-2-phenylacetic acid Chemical compound CC(C)(C)OC(=O)NOC(C(O)=O)C1=CC=CC=C1 SIGWOTBNRFNRQN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OVZGSUWTKMDHSO-UHFFFAOYSA-N 2-aminooxy-N-(4-chlorophenyl)acetamide hydrobromide Chemical compound Br.NOCC(=O)NC1=CC=C(C=C1)Cl OVZGSUWTKMDHSO-UHFFFAOYSA-N 0.000 description 2
- CBIRZHFNWRROLS-UHFFFAOYSA-N 2-aminooxy-N-benzylacetamide hydrobromide Chemical compound Br.C(C1=CC=CC=C1)NC(CON)=O CBIRZHFNWRROLS-UHFFFAOYSA-N 0.000 description 2
- OPJUWIFGTNMKNR-UHFFFAOYSA-N 2-aminooxy-N-cyclopentylacetamide hydrochloride Chemical compound Cl.C1(CCCC1)NC(CON)=O OPJUWIFGTNMKNR-UHFFFAOYSA-N 0.000 description 2
- DFBQNVIGEXKRAC-UHFFFAOYSA-N 2-aminooxy-N-phenylacetamide hydrobromide Chemical compound Br.NOCC(=O)NC1=CC=CC=C1 DFBQNVIGEXKRAC-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 2
- XUHBIQXEFLYOBL-UHFFFAOYSA-N Br.ClC1=CC=C(CNC(CON)=O)C=C1 Chemical compound Br.ClC1=CC=C(CNC(CON)=O)C=C1 XUHBIQXEFLYOBL-UHFFFAOYSA-N 0.000 description 2
- PUCVKGRJUUBSKR-UHFFFAOYSA-N Br.NOCC(=O)NC1=CC=C(C=C1)O Chemical compound Br.NOCC(=O)NC1=CC=C(C=C1)O PUCVKGRJUUBSKR-UHFFFAOYSA-N 0.000 description 2
- MEDMNHKWYGGGFF-UHFFFAOYSA-N C1=CC=C(C=C1)COC(=O)N(C2=CC=CC=C2)C(=O)CON Chemical compound C1=CC=C(C=C1)COC(=O)N(C2=CC=CC=C2)C(=O)CON MEDMNHKWYGGGFF-UHFFFAOYSA-N 0.000 description 2
- PCFDIGPVNYCHCO-UHFFFAOYSA-N C1=CC=C(C=C1)N(C(=O)CON)C(=O)N Chemical compound C1=CC=C(C=C1)N(C(=O)CON)C(=O)N PCFDIGPVNYCHCO-UHFFFAOYSA-N 0.000 description 2
- AZNGHDBAQBZVQC-UHFFFAOYSA-N CC(=O)N(C1=CC=CC=C1)C(=O)CON Chemical compound CC(=O)N(C1=CC=CC=C1)C(=O)CON AZNGHDBAQBZVQC-UHFFFAOYSA-N 0.000 description 2
- MBBWQFJPHQTGND-UHFFFAOYSA-N CC(C)(C)OC(N(C(CON)=O)C1=CC=CC=C1)=O Chemical compound CC(C)(C)OC(N(C(CON)=O)C1=CC=CC=C1)=O MBBWQFJPHQTGND-UHFFFAOYSA-N 0.000 description 2
- QMFVBMWRPDYRMJ-UHFFFAOYSA-N CC(C)(C)OC(NOCC(NC(C=C1)=CC=C1Cl)=O)=O Chemical compound CC(C)(C)OC(NOCC(NC(C=C1)=CC=C1Cl)=O)=O QMFVBMWRPDYRMJ-UHFFFAOYSA-N 0.000 description 2
- UFCUZTBXMQPPHW-UHFFFAOYSA-N CC(C)(C)OC(NOCC(NC(C=CC=C1)=C1OC)=O)=O Chemical compound CC(C)(C)OC(NOCC(NC(C=CC=C1)=C1OC)=O)=O UFCUZTBXMQPPHW-UHFFFAOYSA-N 0.000 description 2
- UASKMSLUXWDJKD-UHFFFAOYSA-N CC(C)(C)OC(NOCC(NC1=C(C)C=CC=C1C)=O)=O Chemical compound CC(C)(C)OC(NOCC(NC1=C(C)C=CC=C1C)=O)=O UASKMSLUXWDJKD-UHFFFAOYSA-N 0.000 description 2
- AQKWGNKNVINFMS-UHFFFAOYSA-N CC(C)(C)OC(NOCC(NC1=CC=CN=C1)=O)=O Chemical compound CC(C)(C)OC(NOCC(NC1=CC=CN=C1)=O)=O AQKWGNKNVINFMS-UHFFFAOYSA-N 0.000 description 2
- IOHIWEHUMYPITF-UHFFFAOYSA-N CC(C)(C)OC(NOCC(NC1CCCC1)=O)=O Chemical compound CC(C)(C)OC(NOCC(NC1CCCC1)=O)=O IOHIWEHUMYPITF-UHFFFAOYSA-N 0.000 description 2
- BRNVMKJFWVYRRL-UHFFFAOYSA-N COC(C=CC=C1)=C1NC(CONC(N)=O)=O Chemical compound COC(C=CC=C1)=C1NC(CONC(N)=O)=O BRNVMKJFWVYRRL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QGPFVPLMVAOLAM-UHFFFAOYSA-N Cl.Cl.N1=CC(=CC=C1)NC(CON)=O Chemical compound Cl.Cl.N1=CC(=CC=C1)NC(CON)=O QGPFVPLMVAOLAM-UHFFFAOYSA-N 0.000 description 2
- PIYKLEZKUSEHBM-UHFFFAOYSA-N Cl.NOCC(=O)NC1=CC=C(C=C1)CC Chemical compound Cl.NOCC(=O)NC1=CC=C(C=C1)CC PIYKLEZKUSEHBM-UHFFFAOYSA-N 0.000 description 2
- OYADWXRKQSOFHG-UHFFFAOYSA-N Cl.NOCC(=O)NC1=CC=C(C=C1)Cl Chemical compound Cl.NOCC(=O)NC1=CC=C(C=C1)Cl OYADWXRKQSOFHG-UHFFFAOYSA-N 0.000 description 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- RRYATXLRCBOQTJ-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) acetate Chemical compound CC(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl RRYATXLRCBOQTJ-UHFFFAOYSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
- KALHAAURVILEMZ-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]oxy-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)NOC(C(O)=O)CC1=CC=CC=C1 KALHAAURVILEMZ-UHFFFAOYSA-N 0.000 description 1
- WVLGQVKSDYRVST-UHFFFAOYSA-N 2-aminooxy-N-(4-ethylphenyl)propanamide hydrochloride Chemical compound Cl.CCC1=CC=C(NC(=O)C(C)ON)C=C1 WVLGQVKSDYRVST-UHFFFAOYSA-N 0.000 description 1
- KROYWLWPQXWNNI-UHFFFAOYSA-N 2-aminooxy-N-(4-nitrophenyl)acetamide hydrobromide Chemical compound Br.NOCC(=O)NC1=CC=C(C=C1)[N+](=O)[O-] KROYWLWPQXWNNI-UHFFFAOYSA-N 0.000 description 1
- UWGFBSKJHHYPHT-UHFFFAOYSA-N 2-aminooxy-n-phenylacetamide Chemical compound NOCC(=O)NC1=CC=CC=C1 UWGFBSKJHHYPHT-UHFFFAOYSA-N 0.000 description 1
- YRKXQWBUHCFMJE-UHFFFAOYSA-N 2-aminooxy-n-phenylpropanamide;hydrochloride Chemical compound Cl.NOC(C)C(=O)NC1=CC=CC=C1 YRKXQWBUHCFMJE-UHFFFAOYSA-N 0.000 description 1
- VTRGCUISDBTZIB-UHFFFAOYSA-N 2-aminooxyacetamide Chemical class NOCC(N)=O VTRGCUISDBTZIB-UHFFFAOYSA-N 0.000 description 1
- AHIBSEICBQMMDB-UHFFFAOYSA-N 2-aminooxypropanoic acid Chemical compound NOC(C)C(O)=O AHIBSEICBQMMDB-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- NKHQKBAKENXNBM-UHFFFAOYSA-N CCOC(C(C=C1)=CC=C1NC(CONC(OCC1=CC=CC=C1)=O)=O)=O Chemical compound CCOC(C(C=C1)=CC=C1NC(CONC(OCC1=CC=CC=C1)=O)=O)=O NKHQKBAKENXNBM-UHFFFAOYSA-N 0.000 description 1
- MOJYDEVUOPZEGX-UHFFFAOYSA-N Cl.NOCC(=O)NC1=CC(=CC=C1)Br Chemical compound Cl.NOCC(=O)NC1=CC(=CC=C1)Br MOJYDEVUOPZEGX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GGISZLOBBISXOZ-UHFFFAOYSA-N acetic acid;chloroform Chemical compound CC(O)=O.ClC(Cl)Cl GGISZLOBBISXOZ-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- IXCKOXLJNNFOCM-UHFFFAOYSA-N n,n,2-triethylaniline Chemical compound CCN(CC)C1=CC=CC=C1CC IXCKOXLJNNFOCM-UHFFFAOYSA-N 0.000 description 1
- KYKDOARTYFGHPC-UHFFFAOYSA-N n-propan-2-ylpropanamide Chemical compound CCC(=O)NC(C)C KYKDOARTYFGHPC-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- CQKAPARXKPTKBK-UHFFFAOYSA-N tert-butylazanium;bromide Chemical compound Br.CC(C)(C)N CQKAPARXKPTKBK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000001549 tubercolostatic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- 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
- C07D213/60—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 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HURI385A HU162469B (de) | 1969-12-29 | 1969-12-29 |
Publications (2)
Publication Number | Publication Date |
---|---|
NO132393B true NO132393B (de) | 1975-07-28 |
NO132393C NO132393C (de) | 1975-11-05 |
Family
ID=11000834
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO4829/70A NO132393C (de) | 1969-12-29 | 1970-12-28 |
Country Status (16)
Country | Link |
---|---|
JP (1) | JPS4928740B1 (de) |
AT (1) | AT305242B (de) |
BE (1) | BE760793A (de) |
CA (1) | CA952113A (de) |
CH (1) | CH561177A5 (de) |
DE (1) | DE2064061C3 (de) |
ES (1) | ES386847A1 (de) |
FI (1) | FI53815C (de) |
FR (1) | FR2081405B1 (de) |
GB (1) | GB1329590A (de) |
HU (1) | HU162469B (de) |
IL (1) | IL35932A (de) |
NL (1) | NL7018971A (de) |
NO (1) | NO132393C (de) |
SE (1) | SE370230B (de) |
YU (1) | YU34514B (de) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS52134132A (en) * | 1976-05-06 | 1977-11-10 | Hitachi Ltd | Controlling system for automatic burner |
JPS59134740U (ja) * | 1983-02-23 | 1984-09-08 | 三国工業株式会社 | 燃焼制御の安全回路 |
CA2932121A1 (en) | 2007-11-30 | 2009-06-11 | Newlink Genetics Corporation | Ido inhibitors |
JP5196448B2 (ja) * | 2007-12-21 | 2013-05-15 | 独立行政法人産業技術総合研究所 | アミノオキシ基を含有する反応性化合物 |
-
1969
- 1969-12-29 HU HURI385A patent/HU162469B/hu unknown
-
1970
- 1970-12-22 SE SE7017451A patent/SE370230B/xx unknown
- 1970-12-23 GB GB6117770A patent/GB1329590A/en not_active Expired
- 1970-12-23 BE BE760793A patent/BE760793A/xx unknown
- 1970-12-26 ES ES386847A patent/ES386847A1/es not_active Expired
- 1970-12-28 NO NO4829/70A patent/NO132393C/no unknown
- 1970-12-28 FI FI3476/70A patent/FI53815C/fi active
- 1970-12-28 DE DE2064061A patent/DE2064061C3/de not_active Expired
- 1970-12-29 JP JP45124602A patent/JPS4928740B1/ja active Pending
- 1970-12-29 CA CA101,590A patent/CA952113A/en not_active Expired
- 1970-12-29 YU YU3187/70A patent/YU34514B/xx unknown
- 1970-12-29 IL IL35932A patent/IL35932A/xx unknown
- 1970-12-29 AT AT1167970A patent/AT305242B/de not_active IP Right Cessation
- 1970-12-29 CH CH1929270A patent/CH561177A5/xx not_active IP Right Cessation
- 1970-12-29 FR FR7047039A patent/FR2081405B1/fr not_active Expired
- 1970-12-29 NL NL7018971A patent/NL7018971A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
BE760793A (fr) | 1971-05-27 |
HU162469B (de) | 1973-02-28 |
FI53815C (fi) | 1978-08-10 |
DE2064061C3 (de) | 1974-05-22 |
GB1329590A (en) | 1973-09-12 |
FR2081405B1 (de) | 1974-07-12 |
CH561177A5 (de) | 1975-04-30 |
CA952113A (en) | 1974-07-30 |
NL7018971A (de) | 1971-07-01 |
IL35932A (en) | 1974-11-29 |
JPS4928740B1 (de) | 1974-07-29 |
AT305242B (de) | 1973-02-12 |
SE370230B (de) | 1974-10-07 |
ES386847A1 (es) | 1973-04-01 |
FR2081405A1 (de) | 1971-12-03 |
IL35932A0 (en) | 1971-02-25 |
FI53815B (fi) | 1978-05-02 |
YU318770A (en) | 1979-02-28 |
DE2064061A1 (de) | 1971-07-15 |
NO132393C (de) | 1975-11-05 |
DE2064061B2 (de) | 1973-10-18 |
YU34514B (en) | 1979-09-10 |
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