CA1099257A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1099257A
Authority: CA; Canada
Prior art keywords: amino; cephem; carboxylic acid; thiomethyl; compound
Prior art date: 1973-12-25
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

Application number

CA340,052A

Other languages

English (en)

Inventor

Mitsuo Numata

Mitsuru Shiraishi

Masayoshi Yamaoka

Isao Minamida

Toshio Miyawaki

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

Priority date (The priority date 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 date listed.)

1973-12-25

Filing date

1979-11-16

Publication date

1981-04-14

1973-12-25 Priority claimed from JP741521A external-priority patent/JPS57873B2/ja

1974-02-20 Priority claimed from JP49020752A external-priority patent/JPS50111093A/ja

1974-04-15 Priority claimed from JP4257474A external-priority patent/JPS57874B2/ja

1974-07-17 Priority claimed from JP8262374A external-priority patent/JPS5652908B2/ja

1974-11-13 Priority claimed from JP13138174A external-priority patent/JPS5512913B2/ja

1975-03-29 Priority claimed from KR7500661A external-priority patent/KR800001569B1/ko

1979-11-16 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1979-11-16 Priority to CA340,052A priority Critical patent/CA1099257A/fr

1981-04-14 Application granted granted Critical

1981-04-14 Publication of CA1099257A publication Critical patent/CA1099257A/fr

Status Expired legal-status Critical Current

Links

229930186147 Cephalosporin Natural products 0.000 title description 14
229940124587 cephalosporin Drugs 0.000 title description 14
150000001780 cephalosporins Chemical class 0.000 title description 14
150000001875 compounds Chemical class 0.000 claims abstract description 87
-1 cephem compounds Chemical class 0.000 claims abstract description 83
150000003839 salts Chemical class 0.000 claims abstract description 13
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 10
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims description 90
125000000217 alkyl group Chemical group 0.000 claims description 67
239000000126 substance Substances 0.000 claims description 40
229910052794 bromium Inorganic materials 0.000 claims description 28
229910052801 chlorine Inorganic materials 0.000 claims description 28
239000000460 chlorine Substances 0.000 claims description 28
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 27
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 25
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
125000004423 acyloxy group Chemical group 0.000 claims description 20
125000004414 alkyl thio group Chemical group 0.000 claims description 19
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 19
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 18
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
125000003396 thiol group Chemical class [H]S* 0.000 claims description 14
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 13
125000003282 alkyl amino group Chemical group 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
125000003831 tetrazolyl group Chemical group 0.000 claims description 5
125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
125000002720 diazolyl group Chemical group 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000002098 pyridazinyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims 20
125000004429 atom Chemical group 0.000 claims 4
125000004433 nitrogen atom Chemical group N* 0.000 claims 4
125000001425 triazolyl group Chemical group 0.000 claims 4
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 3
125000001715 oxadiazolyl group Chemical group 0.000 claims 2
HSHGZXNAXBPPDL-IOJJLOCKSA-N (6r)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 HSHGZXNAXBPPDL-IOJJLOCKSA-N 0.000 claims 1
XUTQHTOXGKVJPN-XCGJVMPOSA-N (6r)-7-amino-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 XUTQHTOXGKVJPN-XCGJVMPOSA-N 0.000 claims 1
NHGDIVKLXRLQQK-HWZXHQHMSA-N (6r)-7-amino-3-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC1=NN=C(N)S1 NHGDIVKLXRLQQK-HWZXHQHMSA-N 0.000 claims 1
HJSGHKMSDOLGJJ-IOJJLOCKSA-N (6r)-7-amino-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 HJSGHKMSDOLGJJ-IOJJLOCKSA-N 0.000 claims 1
ZHIPJKYHQPBNPD-OMNKOJBGSA-N (6r)-7-amino-3-[[5-(2-amino-2-oxoethyl)-1,3,4-thiadiazol-2-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC1=NN=C(CC(N)=O)S1 ZHIPJKYHQPBNPD-OMNKOJBGSA-N 0.000 claims 1
YSRGJBKQWHQSSH-JLOHTSLTSA-N (6r)-7-amino-3-[[5-(2-morpholin-4-yl-2-oxoethyl)sulfanyl-1,3,4-thiadiazol-2-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC(S1)=NN=C1SCC(=O)N1CCOCC1 YSRGJBKQWHQSSH-JLOHTSLTSA-N 0.000 claims 1
DFNMXKXKUCZKBH-OMNKOJBGSA-N (6r)-7-amino-3-[[5-(carboxymethyl)-1,3,4-thiadiazol-2-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC1=NN=C(CC(O)=O)S1 DFNMXKXKUCZKBH-OMNKOJBGSA-N 0.000 claims 1
DXIMROGRHVUZHW-FFFFSGIJSA-N (6r)-7-amino-3-[[5-[2-(dimethylamino)-2-oxoethyl]-1,3,4-thiadiazol-2-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(CC(=O)N(C)C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 DXIMROGRHVUZHW-FFFFSGIJSA-N 0.000 claims 1
OBZPELDGSNYFTD-XCGJVMPOSA-N (6r)-7-amino-8-oxo-3-(1,3,4-thiadiazol-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC1=NN=CS1 OBZPELDGSNYFTD-XCGJVMPOSA-N 0.000 claims 1
IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims 1
PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 abstract description 9
238000001228 spectrum Methods 0.000 abstract description 7
241000588724 Escherichia coli Species 0.000 abstract description 4
241000588772 Morganella morganii Species 0.000 abstract description 2
241000588767 Proteus vulgaris Species 0.000 abstract description 2
230000000845 anti-microbial effect Effects 0.000 abstract description 2
229940007042 proteus vulgaris Drugs 0.000 abstract description 2
241000894006 Bacteria Species 0.000 abstract 1
241000588747 Klebsiella pneumoniae Species 0.000 abstract 1
239000004599 antimicrobial Substances 0.000 abstract 1
230000001225 therapeutic effect Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000000047 product Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000013078 crystal Substances 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
229940093499 ethyl acetate Drugs 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
238000003756 stirring Methods 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000010410 layer Substances 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 3
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
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 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 3
244000005700 microbiome Species 0.000 description 3
229960004838 phosphoric acid Drugs 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
244000110797 Polygonum persicaria Species 0.000 description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
229940022663 acetate Drugs 0.000 description 2
MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 2
229960001139 cefazolin Drugs 0.000 description 2
HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000000463 material Substances 0.000 description 2
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 2
229920005990 polystyrene resin Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
CIFZTJFBDLIEOW-JLOHTSLTSA-N (6r)-3-(acetyloxymethyl)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)NC(=O)CC1=CSC(N)=N1 CIFZTJFBDLIEOW-JLOHTSLTSA-N 0.000 description 1
IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 1
125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
125000005042 acyloxymethyl group Chemical group 0.000 description 1
239000008272 agar Substances 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
125000005079 alkoxycarbonylmethyl group Chemical group 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
230000036765 blood level Effects 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical class O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 1
229960003866 cefaloridine 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
239000012141 concentrate Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
229940043237 diethanolamine Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
229940096118 ella Drugs 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000006352 iso-propylthiomethyl group Chemical group [H]C([H])([H])C([H])(SC([H])([H])*)C([H])([H])[H] 0.000 description 1
230000007775 late Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
ZFRSLDLBIUSAHF-XTBNCEIVSA-M sodium;(6r)-3-(acetyloxymethyl)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].C1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)NC(=O)CC1=CSC(N)=N1 ZFRSLDLBIUSAHF-XTBNCEIVSA-M 0.000 description 1
GKIORNMIXFGNLY-ZHWMGRLRSA-M sodium;(6r)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].CN1N=NN=C1SCC1=C(C([O-])=O)N2C(=O)C(NC(=O)CC=3N=C(N)SC=3)[C@H]2SC1 GKIORNMIXFGNLY-ZHWMGRLRSA-M 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 description 1

Classifications

- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Cephalosporin Compounds (AREA)

CA340,052A 1973-12-25 1979-11-16 Traduction non-disponible Expired CA1099257A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA340,052A CA1099257A (fr)	1973-12-25	1979-11-16	Traduction non-disponible

Applications Claiming Priority (12)

Application Number	Priority Date	Filing Date	Title
JP1521/74		1973-12-25
JP741521A JPS57873B2 (fr)	1973-12-25	1973-12-25
JP49020752A JPS50111093A (fr)	1974-02-20	1974-02-20
JP20752/74		1974-02-20
JP42574/74		1974-04-15
JP4257474A JPS57874B2 (fr)	1974-04-15	1974-04-15
JP82623/74		1974-07-17
JP8262374A JPS5652908B2 (fr)	1974-07-17	1974-07-17
JP131381/74		1974-11-13
JP13138174A JPS5512913B2 (fr)	1974-11-13	1974-11-13
KR7500661A KR800001569B1 (ko)	1973-12-25	1975-03-29	세팔로스포린 유도체의 제조법
CA340,052A CA1099257A (fr)	1973-12-25	1979-11-16	Traduction non-disponible

Publications (1)

Publication Number	Publication Date
CA1099257A true CA1099257A (fr)	1981-04-14

Family

ID=27560898

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA340,052A Expired CA1099257A (fr)	1973-12-25	1979-11-16	Traduction non-disponible

Country Status (1)

Country	Link
CA (1)	CA1099257A (fr)

1979
- 1979-11-16 CA CA340,052A patent/CA1099257A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-04-14	MKEX	Expiry

Publication	Publication Date	Title
US4421912A (en)	1983-12-20	Cephalosporin derivatives
CA1316171C (fr)	1993-04-13	Derives de cephalosporine
FI66188B (fi)	1984-05-31	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara s-oxider och -dioxider av 7-(2-(2-aminotiazol-4-yl)-2-oxiimino-acetamido)-cef-3-em-4-karboxylsyraderivat
CA1039270A (fr)	1978-09-26	Cephalosporine a radical thio en position 3
HU177441B (en)	1981-10-28	Process for preparing syn isomers of 3,7-disubstituted 3-cephem-4-carboxylic acid derivatives
US3819623A (en)	1974-06-25	3,7-disubstituted cephalosporin compounds
DE2162575A1 (de)	1972-07-27	Cephalosporinverbindungen und diese Verbindungen enthaltende Arzneimittel
CA1225390A (fr)	1987-08-11	Cephalosporines 3-bicyclopyridinium-methyliques
US4482710A (en)	1984-11-13	Process for preparing 3-alkoxymethylcephalosporin derivatives
EP0043546B1 (fr)	1986-01-29	7-Oxo-céphalosporines et 6-oxo-pénicillines, leurs homologues et procédé pour leur préparation
CA1283096C (fr)	1991-04-16	Composes antibacteriens
CA1065854A (fr)	1979-11-06	Derives du 7-acetoacetamidocephem
CA1092095A (fr)	1980-12-23	Composes a base de 3-acyloxymethyl-cephem
EP0082498A2 (fr)	1983-06-29	Dérivés bêta-lactame et procédé pour leur préparation
US5066800A (en)	1991-11-19	Qunoline intermediates useful therein for synthesizing antibacterial compounds
JP2529093B2 (ja)	1996-08-28	セファロスポリン中間体の製造方法
US4239758A (en)	1980-12-16	Cephalosporins
US4311842A (en)	1982-01-19	Cephalosporin compounds
US3772286A (en)	1973-11-13	7-ureidocephalosporins
CA1074296A (fr)	1980-03-25	Composes de 3-acyloxymethylcephem
US5484928A (en)	1996-01-16	2-(2-aminothiazol-4-yl)-2-oxoacetic acid derivatives
US4379924A (en)	1983-04-12	Cephalosporin derivatives
DE3043865A1 (de)	1981-09-03	N-substituierte thiazolylderivate von oxy-imino-substituierten cephalosporinen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische und veterinaermedizinische mittel
CA1075679A (fr)	1980-04-15	3-heterothio-7-thioureidocephalosporines
CA1057738A (fr)	1979-07-03	(((alkylthiocarbonyl)oxy) acetyl) cephalosporines