CA1111021A - Acyl derivatives - Google Patents
Acyl derivativesInfo
- Publication number
- CA1111021A CA1111021A CA229,803A CA229803A CA1111021A CA 1111021 A CA1111021 A CA 1111021A CA 229803 A CA229803 A CA 229803A CA 1111021 A CA1111021 A CA 1111021A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- methyl
- dioxo
- tetrahydro
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000002252 acyl group Chemical group 0.000 title claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 105
- 238000000034 method Methods 0.000 claims abstract description 85
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
- 150000004677 hydrates Chemical class 0.000 claims abstract description 8
- -1 1-tetrazolyl Chemical group 0.000 claims description 201
- 238000004519 manufacturing process Methods 0.000 claims description 58
- 229960000603 cefalotin Drugs 0.000 claims description 44
- 239000000126 substance Substances 0.000 claims description 42
- XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 239000007858 starting material Substances 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 25
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 24
- LFYOIWKDYNCFNR-UHFFFAOYSA-N 4-ethyl-3-sulfanylidene-1,2,4-triazinane-5,6-dione Chemical compound CCN1C(S)=NN=C(O)C1=O LFYOIWKDYNCFNR-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 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 15
- 229940124587 cephalosporin Drugs 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
- 229930186147 Cephalosporin Natural products 0.000 claims description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 10
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- GRWAIJBHBCCLGS-UHFFFAOYSA-N 2-(tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1C=NN=N1 GRWAIJBHBCCLGS-UHFFFAOYSA-N 0.000 claims description 5
- CJDXQHXLUSJTMO-UHFFFAOYSA-N 4-methyl-3-sulfanylidene-1,2,4-triazinane-5,6-dione Chemical compound CN1C(S)=NN=C(O)C1=O CJDXQHXLUSJTMO-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 229950004030 cefaloglycin Drugs 0.000 claims description 4
- 150000001780 cephalosporins Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- VLQMHTXSYRXAJU-UHFFFAOYSA-N 1,4-diethyl-3-sulfanylidene-1,2,4-triazinane-5,6-dione Chemical compound CCN1N=C(S)N(CC)C(=O)C1=O VLQMHTXSYRXAJU-UHFFFAOYSA-N 0.000 claims description 3
- KZSLHPBJJSPILT-UHFFFAOYSA-N 1-ethyl-3-sulfanylidene-1,2,4-triazinane-5,6-dione Chemical compound CCN1NC(=S)NC(=O)C1=O KZSLHPBJJSPILT-UHFFFAOYSA-N 0.000 claims description 3
- ILEZLXLLLYYQAX-UHFFFAOYSA-N 1-ethyl-4-sulfanylidenepyrimidin-2-one Chemical compound CCN1C=CC(S)=NC1=O ILEZLXLLLYYQAX-UHFFFAOYSA-N 0.000 claims description 3
- QXMOUGSKSWZDOI-UHFFFAOYSA-N 1-ethyl-6-methyl-2-sulfanylidenepyrimidin-4-one Chemical compound CCN1C(C)=CC(=O)N=C1S QXMOUGSKSWZDOI-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 229960003972 cefacetrile Drugs 0.000 claims description 3
- RRYMAQUWDLIUPV-BXKDBHETSA-N cefacetrile Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC#N)[C@@H]12 RRYMAQUWDLIUPV-BXKDBHETSA-N 0.000 claims description 3
- FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 claims description 3
- DHKQGZQQBUORJS-UHFFFAOYSA-N 1-amino-4-sulfanylidenepyrimidin-2-one Chemical compound NN1C=CC(=S)NC1=O DHKQGZQQBUORJS-UHFFFAOYSA-N 0.000 claims description 2
- STIDBAKBUIRMGQ-UHFFFAOYSA-N 1-butoxy-4-sulfanylidenepyrimidin-2-one Chemical compound CCCCON1C=CC(S)=NC1=O STIDBAKBUIRMGQ-UHFFFAOYSA-N 0.000 claims description 2
- WKGQCEADQVWHBK-UHFFFAOYSA-N 3,6-dimethyl-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound CC1=CC(=O)N(C)C(S)=N1 WKGQCEADQVWHBK-UHFFFAOYSA-N 0.000 claims description 2
- DDGUXTGMUNEGOJ-UHFFFAOYSA-N 4-(2-methoxyethyl)-3-sulfanylidene-1,2,4-triazinane-5,6-dione Chemical compound COCCN1C(=S)NNC(=O)C1=O DDGUXTGMUNEGOJ-UHFFFAOYSA-N 0.000 claims description 2
- RTYJEWCPNNMFKA-UHFFFAOYSA-N 4-butyl-3-sulfanylidene-1,2,4-triazinane-5,6-dione Chemical compound CCCCN1C(S)=NNC(=O)C1=O RTYJEWCPNNMFKA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- JYWBSWSHTPGXEW-ABIUDSBCSA-N (6R)-4-acetamido-3-(acetyloxymethyl)-8-oxo-7-thiophen-2-yl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(=CC=C1)C1[C@@H]2N(C(=C(C(S2)NC(C)=O)COC(C)=O)C(=O)O)C1=O JYWBSWSHTPGXEW-ABIUDSBCSA-N 0.000 claims 2
- NGQILHFOYCDCGO-UHFFFAOYSA-N 1-butoxy-5-methyl-4-sulfanylidenepyrimidin-2-one Chemical compound CCCCON1C=C(C)C(S)=NC1=O NGQILHFOYCDCGO-UHFFFAOYSA-N 0.000 claims 2
- ARXTVWVMIMBQEY-BBEGDGIKSA-N (6R,7R)-3-[(4-ethyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(C)N1C(=NNC(C1=O)=O)SCC=1CS[C@H]2N(C=1C(=O)O)C([C@H]2NC([C@H](O)C1=CC=CC=C1)=O)=O ARXTVWVMIMBQEY-BBEGDGIKSA-N 0.000 claims 1
- FKFIVLNXDYAFPR-CZIZLABSSA-N (6R,7R)-3-[(4-ethyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-7-[[(2R)-2-hydroxy-4-methylpentanoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(C)N1C(=NNC(C1=O)=O)SCC=1CS[C@H]2N(C=1C(=O)O)C([C@H]2NC([C@@H](CC(C)C)O)=O)=O FKFIVLNXDYAFPR-CZIZLABSSA-N 0.000 claims 1
- RJAYAMZXNSWKSX-CZIZLABSSA-N (6R,7R)-3-[(4-ethyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-7-[[(2R)-2-hydroxyhexanoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(C)N1C(=NNC(C1=O)=O)SCC=1CS[C@H]2N(C=1C(=O)O)C([C@H]2NC([C@@H](CCCC)O)=O)=O RJAYAMZXNSWKSX-CZIZLABSSA-N 0.000 claims 1
- OGPONJXSYNUSMC-AUUYWEPGSA-N (6r,7r)-3-[(1,4-diethyl-5,6-dioxo-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CCN1C(=O)C(=O)N(CC)N=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC=3SC=CC=3)[C@H]2SC1 OGPONJXSYNUSMC-AUUYWEPGSA-N 0.000 claims 1
- HTQAIPHCVDDSAE-CRAIPNDOSA-N (6r,7r)-3-[(1,4-dimethyl-6-oxopyrimidin-2-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CC1=CC(=O)N(C)C(SCC=2CS[C@H]3N(C([C@H]3NC(=O)CC=3SC=CC=3)=O)C=2C(O)=O)=N1 HTQAIPHCVDDSAE-CRAIPNDOSA-N 0.000 claims 1
- QKRIACCEBKVDAT-CZUORRHYSA-N (6r,7r)-3-[(1-amino-2-oxopyrimidin-4-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O=C1N(N)C=CC(SCC=2CS[C@H]3N(C([C@H]3NC(=O)CC=3SC=CC=3)=O)C=2C(O)=O)=N1 QKRIACCEBKVDAT-CZUORRHYSA-N 0.000 claims 1
- ZEDUYJVFACRVNV-ZWNOBZJWSA-N (6r,7r)-3-[(1-amino-2-oxopyrimidin-4-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O=C1N(N)C=CC(SCC=2CS[C@H]3N(C([C@H]3NC(=O)CN3N=NN=C3)=O)C=2C(O)=O)=N1 ZEDUYJVFACRVNV-ZWNOBZJWSA-N 0.000 claims 1
- BRROOYJWWCXDSQ-YLJYHZDGSA-N (6r,7r)-3-[(1-butoxy-2-oxopyrimidin-4-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O=C1N(OCCCC)C=CC(SCC=2CS[C@H]3N(C([C@H]3NC(=O)CC=3SC=CC=3)=O)C=2C(O)=O)=N1 BRROOYJWWCXDSQ-YLJYHZDGSA-N 0.000 claims 1
- QYGBTWZAZHAZSG-DYESRHJHSA-N (6r,7r)-3-[(1-butoxy-5-methyl-2-oxopyrimidin-4-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O=C1N(OCCCC)C=C(C)C(SCC=2CS[C@H]3N(C([C@H]3NC(=O)CC=3SC=CC=3)=O)C=2C(O)=O)=N1 QYGBTWZAZHAZSG-DYESRHJHSA-N 0.000 claims 1
- ZCEQPYXLNLSRBP-CRAIPNDOSA-N (6r,7r)-3-[(1-ethyl-2-oxopyrimidin-4-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O=C1N(CC)C=CC(SCC=2CS[C@H]3N(C([C@H]3NC(=O)CC=3SC=CC=3)=O)C=2C(O)=O)=N1 ZCEQPYXLNLSRBP-CRAIPNDOSA-N 0.000 claims 1
- ZASVAIISBAYZBQ-SJKOYZFVSA-N (6r,7r)-3-[(1-ethyl-5,6-dioxo-2h-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O=C1C(=O)N(CC)NC(SCC=2CS[C@H]3N(C([C@H]3NC(=O)CC=3SC=CC=3)=O)C=2C(O)=O)=N1 ZASVAIISBAYZBQ-SJKOYZFVSA-N 0.000 claims 1
- UPBXAAGIJHVVRO-AUUYWEPGSA-N (6r,7r)-3-[(4-butyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N1C(=O)C(=O)N(CCCC)C(SCC=2CS[C@H]3N(C([C@H]3NC(=O)CC=3SC=CC=3)=O)C=2C(O)=O)=N1 UPBXAAGIJHVVRO-AUUYWEPGSA-N 0.000 claims 1
- YUFULSSJRKXPGL-SJKOYZFVSA-N (6r,7r)-3-[(4-ethyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N1C(=O)C(=O)N(CC)C(SCC=2CS[C@H]3N(C([C@H]3NC(=O)CC=3SC=CC=3)=O)C=2C(O)=O)=N1 YUFULSSJRKXPGL-SJKOYZFVSA-N 0.000 claims 1
- CGZGYCWEUAQONY-BDJLRTHQSA-N (6r,7r)-3-[(4-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N1C(=O)C(=O)N(C)C(SCC=2CS[C@H]3N(C([C@H]3NC(=O)CC=3SC=CC=3)=O)C=2C(O)=O)=N1 CGZGYCWEUAQONY-BDJLRTHQSA-N 0.000 claims 1
- OLGZNTYOAUKSNH-YMTOWFKASA-N (6r,7r)-7-[(2-cyanoacetyl)amino]-3-[(4-ethyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N1C(=O)C(=O)N(CC)C(SCC=2CS[C@H]3N(C([C@H]3NC(=O)CC#N)=O)C=2C(O)=O)=N1 OLGZNTYOAUKSNH-YMTOWFKASA-N 0.000 claims 1
- ZCDXSKFCZLHNAV-VLXJIEOASA-N (6r,7r)-7-[[(2r)-2-amino-2-phenylacetyl]amino]-3-[(4-ethyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N1C(=O)C(=O)N(CC)C(SCC=2CS[C@H]3N(C([C@H]3NC(=O)[C@H](N)C=3C=CC=CC=3)=O)C=2C(O)=O)=N1 ZCDXSKFCZLHNAV-VLXJIEOASA-N 0.000 claims 1
- PFDZFIOGANIPGC-MJGOQNOKSA-N (6r,7s)-7-methoxy-3-[(4-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@]1(OC)C(N2C(=C(CSC=3N(C(=O)C(=O)NN=3)C)CS[C@@H]21)C(O)=O)=O)C(=O)CC1=CC=CS1 PFDZFIOGANIPGC-MJGOQNOKSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 10
- 125000003368 amide group Chemical group 0.000 abstract description 2
- 230000003115 biocidal effect Effects 0.000 abstract description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000002844 melting Methods 0.000 description 65
- 230000008018 melting Effects 0.000 description 65
- 159000000000 sodium salts Chemical class 0.000 description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 238000000354 decomposition reaction Methods 0.000 description 44
- 239000000243 solution Substances 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 125000000217 alkyl group Chemical group 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 235000011167 hydrochloric acid Nutrition 0.000 description 14
- 229960000443 hydrochloric acid Drugs 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 9
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 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 5
- 150000007513 acids Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
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- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- RDEAKCXMQCTSEB-UHFFFAOYSA-N butoxyurea Chemical compound CCCCONC(N)=O RDEAKCXMQCTSEB-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229960004350 cefapirin Drugs 0.000 description 1
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000007928 imidazolide derivatives Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229960004393 lidocaine hydrochloride Drugs 0.000 description 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- CDHRVOKWLXOXRZ-UHFFFAOYSA-N n,n'-dibenzyl-n'-ethylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CC)CCNCC1=CC=CC=C1 CDHRVOKWLXOXRZ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229950009506 penicillinase Drugs 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000005494 pyridonyl group Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003583 thiosemicarbazides Chemical class 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three 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
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000387618A CA1240314A (en) | 1974-06-21 | 1981-10-08 | Acyl derivatives |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH853774A CH609989A5 (en) | 1974-06-21 | 1974-06-21 | Process for the preparation of acyl derivatives |
| CH8537/74 | 1974-06-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1111021A true CA1111021A (en) | 1981-10-20 |
Family
ID=4341690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA229,803A Expired CA1111021A (en) | 1974-06-21 | 1975-06-20 | Acyl derivatives |
Country Status (25)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1599232A (en) * | 1977-06-03 | 1981-09-30 | Hoffmann La Roche | 7-(2-oximinoacetamido)-cephalosporin derivatives |
| JPS5419990A (en) * | 1977-07-14 | 1979-02-15 | Shionogi & Co Ltd | Dihydrotriazinylthioxacephalosporin |
| MC1259A1 (fr) * | 1978-05-30 | 1980-01-14 | Hoffmann La Roche | Derives acyles |
| FR2474030A1 (fr) * | 1980-01-17 | 1981-07-24 | Rhone Poulenc Ind | Nouvelles dioxotriazines et leur preparation |
| FR2494278A1 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouveaux derives de la cephalosporine, leurs preparations et les medicaments qui les contiennent |
| CN1531598A (zh) * | 2001-04-19 | 2004-09-22 | ��ŷ�����¶����ǹɷ�����˾ | 制备头孢菌素衍生物的酶促方法 |
| HUE025132T2 (en) | 2008-03-05 | 2016-01-28 | Merck Patent Gmbh | Pyrazinone derivatives that stimulate insulin secretion, methods for their preparation and their use in the treatment of diabetes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3868369A (en) * | 1972-11-14 | 1975-02-25 | Smithkline Corp | 3-heterocyclicthiomethylcephalosporins |
-
1974
- 1974-06-21 CH CH853774A patent/CH609989A5/xx not_active IP Right Cessation
-
1975
- 1975-05-13 ZA ZA00753086A patent/ZA753086B/xx unknown
- 1975-05-13 NZ NZ177508A patent/NZ177508A/xx unknown
- 1975-05-14 IL IL47299A patent/IL47299A/xx unknown
- 1975-06-06 AU AU81912/75A patent/AU498387B2/en not_active Expired
- 1975-06-16 SE SE7506908A patent/SE431755B/xx not_active IP Right Cessation
- 1975-06-17 PH PH17273A patent/PH13030A/en unknown
- 1975-06-17 BR BR4864/75D patent/BR7503782A/pt unknown
- 1975-06-17 DK DK271975A patent/DK153155C/da not_active IP Right Cessation
- 1975-06-18 FI FI751815A patent/FI751815A7/fi not_active Application Discontinuation
- 1975-06-18 SU SU752145554A patent/SU635873A3/ru active
- 1975-06-18 JP JP50074251A patent/JPS625917B2/ja not_active Expired
- 1975-06-18 IE IE1366/75A patent/IE41888B1/en unknown
- 1975-06-19 LU LU72771A patent/LU72771A1/xx unknown
- 1975-06-19 DE DE19752527291 patent/DE2527291A1/de active Granted
- 1975-06-19 FR FR7519213A patent/FR2275215A1/fr active Granted
- 1975-06-20 CA CA229,803A patent/CA1111021A/en not_active Expired
- 1975-06-20 CU CU7534293A patent/CU34293A/es unknown
- 1975-06-20 BE BE157517A patent/BE830455A/xx not_active IP Right Cessation
- 1975-06-20 NL NLAANVRAGE7507390,A patent/NL180665C/xx not_active IP Right Cessation
- 1975-06-20 HU HUHO1808A patent/HU170576B/hu unknown
- 1975-06-20 DD DD186797A patent/DD121113A5/xx unknown
- 1975-06-20 AT AT476975A patent/AT337897B/de not_active IP Right Cessation
- 1975-06-20 GB GB2634175A patent/GB1471804A/en not_active Expired
- 1975-06-20 NO NO752202A patent/NO752202L/no unknown
-
1976
- 1976-01-07 SU SU762309104A patent/SU589921A3/ru active
-
1987
- 1987-08-28 DK DK453687A patent/DK155329C/da not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |