NO883590L - Acylderivater. - Google Patents

Acylderivater.

Info

Publication number: NO883590L
Authority: NO; Norway
Prior art keywords: methyl; compounds; amino; oxo; carbamoyl
Prior art date: 1987-08-14

Application number

NO88883590A

Other languages

English (en)

Norwegian (no)

Other versions

NO883590D0 (no

Inventor

Erwin Goetschi

Original Assignee

Hoffmann La Roche

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.)

1987-08-14

Filing date

1988-08-12

Publication date

1989-02-15

1988-08-12 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1988-08-12 Publication of NO883590D0 publication Critical patent/NO883590D0/no

1989-02-15 Publication of NO883590L publication Critical patent/NO883590L/no

Links

125000002252 acyl group Chemical group 0.000 title claims description 3
-1 or a 6-membered Chemical group 0.000 claims description 132
125000000217 alkyl group Chemical group 0.000 claims description 87
150000001875 compounds Chemical class 0.000 claims description 86
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 74
238000000034 method Methods 0.000 claims description 71
125000001841 imino group Chemical group [H]N=* 0.000 claims description 60
SCNWTQPZTZMXBG-UHFFFAOYSA-N 2-methyloct-2-enoic acid Chemical compound CCCCCC=C(C)C(O)=O SCNWTQPZTZMXBG-UHFFFAOYSA-N 0.000 claims description 59
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 59
239000000047 product Substances 0.000 claims description 57
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 55
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 54
150000003839 salts Chemical class 0.000 claims description 50
239000007858 starting material Substances 0.000 claims description 40
150000002148 esters Chemical class 0.000 claims description 38
125000000623 heterocyclic group Chemical group 0.000 claims description 36
239000002253 acid Substances 0.000 claims description 28
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 28
238000002360 preparation method Methods 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 26
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 19
150000002431 hydrogen Chemical class 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 16
150000004677 hydrates Chemical class 0.000 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
150000001780 cephalosporins Chemical class 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
229930186147 Cephalosporin Natural products 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
229940124587 cephalosporin Drugs 0.000 claims description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 5
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 5
229960003237 betaine Drugs 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
125000002619 bicyclic group Chemical group 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
238000011321 prophylaxis Methods 0.000 claims description 4
238000011282 treatment Methods 0.000 claims description 4
208000035473 Communicable disease Diseases 0.000 claims description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000004103 aminoalkyl group Chemical group 0.000 claims description 3
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
150000001879 copper Chemical class 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
229940126601 medicinal product Drugs 0.000 claims description 3
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 3
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 3
125000001118 alkylidene group Chemical group 0.000 claims description 2
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 claims description 2
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
XMGMFRIEKMMMSU-UHFFFAOYSA-N phenylmethylbenzene Chemical group C=1C=CC=CC=1[C]C1=CC=CC=C1 XMGMFRIEKMMMSU-UHFFFAOYSA-N 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 112
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 99
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 88
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
239000000203 mixture Substances 0.000 description 48
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
239000011541 reaction mixture Substances 0.000 description 36
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 34
239000000843 powder Substances 0.000 description 30
239000002244 precipitate Substances 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 21
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 20
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
150000002923 oximes Chemical class 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
235000011121 sodium hydroxide Nutrition 0.000 description 18
239000000499 gel Substances 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
239000000706 filtrate Substances 0.000 description 16
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
239000013078 crystal Substances 0.000 description 15
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 14
238000004108 freeze drying Methods 0.000 description 14
239000000463 material Substances 0.000 description 12
239000012074 organic phase Substances 0.000 description 12
229910052938 sodium sulfate Inorganic materials 0.000 description 12
235000011152 sodium sulphate Nutrition 0.000 description 12
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 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
238000003756 stirring Methods 0.000 description 10
239000000126 substance Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 10
239000008346 aqueous phase Substances 0.000 description 9
239000002585 base Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
238000001914 filtration Methods 0.000 description 8
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 8
229910015900 BF3 Inorganic materials 0.000 description 7
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
239000012876 carrier material Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
238000001816 cooling Methods 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
150000002430 hydrocarbons Chemical group 0.000 description 5
PLUBDQHYMHSVEI-UHFFFAOYSA-N methyl 2h-pyrimidine-1-carboxylate Chemical compound COC(=O)N1CN=CC=C1 PLUBDQHYMHSVEI-UHFFFAOYSA-N 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
235000011181 potassium carbonates Nutrition 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
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 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
230000001143 conditioned effect Effects 0.000 description 4
239000012043 crude product Substances 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
150000004292 cyclic ethers Chemical class 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000007903 gelatin capsule Substances 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
239000007788 liquid Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
238000000746 purification Methods 0.000 description 4
150000005846 sugar alcohols Polymers 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
125000005907 alkyl ester group Chemical group 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000011097 chromatography purification Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
KVTTTZRERLOCFN-UHFFFAOYSA-M lithium;2,2-diphenyl-1,3-benzodioxole-5-sulfinate Chemical compound [Li+].O1C2=CC(S(=O)[O-])=CC=C2OC1(C=1C=CC=CC=1)C1=CC=CC=C1 KVTTTZRERLOCFN-UHFFFAOYSA-M 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 3
239000000052 vinegar Substances 0.000 description 3
235000021419 vinegar Nutrition 0.000 description 3
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
RARBEEPFNXYAGR-UHFFFAOYSA-N 2,2-dimethyl-5-methylsulfanyl-1,3-benzodioxole Chemical compound CSC1=CC=C2OC(C)(C)OC2=C1 RARBEEPFNXYAGR-UHFFFAOYSA-N 0.000 description 2
IZDBVQTVHWUFOP-UHFFFAOYSA-N 2,2-dimethyl-5-methylsulfinyl-1,3-benzodioxole Chemical compound CS(=O)C1=CC=C2OC(C)(C)OC2=C1 IZDBVQTVHWUFOP-UHFFFAOYSA-N 0.000 description 2
VMASTYPGLHRVNL-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetic acid Chemical compound NC1=NC(C(=O)C(O)=O)=CS1 VMASTYPGLHRVNL-UHFFFAOYSA-N 0.000 description 2
VBVJERQQYCZNOS-UHFFFAOYSA-N 3,4-dihydroxybenzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=C(O)C(O)=C1 VBVJERQQYCZNOS-UHFFFAOYSA-N 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
DZPGCBNJLAKMQJ-UHFFFAOYSA-N 5-bromo-2,2-diphenyl-1,3-benzodioxole Chemical compound O1C2=CC(Br)=CC=C2OC1(C=1C=CC=CC=1)C1=CC=CC=C1 DZPGCBNJLAKMQJ-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
FOPPBRUPIHUFAH-UHFFFAOYSA-N FC(F)(F)C1=CC(S)=NC2=C(C(=O)N)C=NN21 Chemical compound FC(F)(F)C1=CC(S)=NC2=C(C(=O)N)C=NN21 FOPPBRUPIHUFAH-UHFFFAOYSA-N 0.000 description 2
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125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
JOQJEWAXHQDQAG-UHFFFAOYSA-N methyl pyrimidine-2-carboxylate Chemical compound COC(=O)C1=NC=CC=N1 JOQJEWAXHQDQAG-UHFFFAOYSA-N 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 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
ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000003755 preservative agent Substances 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
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000012264 purified product Substances 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
HZGCZRCZOMANHK-UHFFFAOYSA-N pyrimidin-2-ylmethanol Chemical compound OCC1=NC=CC=N1 HZGCZRCZOMANHK-UHFFFAOYSA-N 0.000 description 1
ZFCHNZDUMIOWFV-UHFFFAOYSA-M pyrimidine-2-carboxylate Chemical compound [O-]C(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-M 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
UFWZVYJQVSWHEK-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl) 2-(1,3-dioxoisoindol-2-yl)oxy-2-methylpropanethioate Chemical compound C1=CC=C2SC(SC(=O)C(C)(ON3C(C4=CC=CC=C4C3=O)=O)C)=NC2=C1 UFWZVYJQVSWHEK-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000012064 sodium phosphate buffer Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
WRVHPSSSTBDGRK-UHFFFAOYSA-N sodium;sulfane;hydrate Chemical compound O.[Na].S WRVHPSSSTBDGRK-UHFFFAOYSA-N 0.000 description 1
239000011343 solid material Substances 0.000 description 1
235000014347 soups Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
229960004418 trolamine Drugs 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- 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
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
- 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
- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)

NO88883590A 1987-08-14 1988-08-12 Acylderivater. NO883590L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH313387		1987-08-14
CH472687		1987-12-03

Publications (2)

Publication Number	Publication Date
NO883590D0 NO883590D0 (no)	1988-08-12
NO883590L true NO883590L (no)	1989-02-15

Family

ID=25692275

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO88883590A NO883590L (no)	1987-08-14	1988-08-12	Acylderivater.

Country Status (15)

Country	Link
US (2)	US5036064A (da)
EP (1)	EP0303172A3 (da)
JP (1)	JPS6466190A (da)
KR (1)	KR890003776A (da)
AU (1)	AU614984B2 (da)
DK (1)	DK455288A (da)
FI (1)	FI883766A7 (da)
HU (1)	HUT47944A (da)
IL (1)	IL87374A0 (da)
MC (1)	MC1970A1 (da)
NO (1)	NO883590L (da)
NZ (1)	NZ225754A (da)
PH (1)	PH25646A (da)
PT (1)	PT88274B (da)
YU (1)	YU156388A (da)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0366189A3 (en) *	1988-10-24	1992-01-02	Norwich Eaton Pharmaceuticals, Inc.	Novel antimicrobial lactam-quinolones
US5030724A (en) *	1990-01-22	1991-07-09	E. R. Squibb & Sons, Inc.	Monobactam hydrazides containing catechol sulfonic acid groups
US20040197408A1 (en) *	2002-12-30	2004-10-07	Angiotech International Ag	Amino acids in micelle preparation
US7537532B2 (en) *	2007-05-16	2009-05-26	Young Carl D	Handle for implement and method
KR101719556B1 (ko) *	2011-03-30	2017-03-24	주식회사 레고켐 바이오사이언스	신규한 세파로스포린 유도체 및 이를 함유하는 의약 조성물
MX352760B (es)	2011-09-09	2017-12-07	Merck Sharp & Dohme Corp Star	Metodos para tratar infecciones intrapulmonares.
JPWO2013051597A1 (ja) *	2011-10-04	2015-03-30	塩野義製薬株式会社	カテコール基を有するセフェム誘導体
US8809314B1 (en)	2012-09-07	2014-08-19	Cubist Pharmacueticals, Inc.	Cephalosporin compound
US8476425B1 (en)	2012-09-27	2013-07-02	Cubist Pharmaceuticals, Inc.	Tazobactam arginine compositions
US10011715B2 (en)	2012-11-19	2018-07-03	Mitsui Chemicals, Inc.	Polyester resin composition, manufacturing method therefor, and camera module containing said polyester resin composition
DK2893929T3 (da)	2013-03-15	2025-07-07	Merck Sharp & Dohme Llc	Antibiotisk ceftolozansammensætninger
US20140274993A1 (en)	2013-03-15	2014-09-18	Cubist Pharmaceuticals, Inc.	Ceftolozane-tazobactam pharmaceutical compositions
US9872906B2 (en)	2013-03-15	2018-01-23	Merck Sharp & Dohme Corp.	Ceftolozane antibiotic compositions
EP3043797B1 (en)	2013-09-09	2020-04-08	Merck Sharp & Dohme Corp.	Treating infections with ceftolozane/tazobactam in subjects having impaired renal function
US20150094293A1 (en)	2013-09-27	2015-04-02	Calixa Therapeutics, Inc.	Solid forms of ceftolozane

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4166115A (en) *	1976-04-12	1979-08-28	Fujisawa Pharmaceutical Co., Ltd.	Syn 7-oxoimino substituted derivatives of cephalosporanic acid
GB1596278A (en) *	1976-11-30	1981-08-26	Glaxo Operations Ltd	7-(-oxyimino-acetamino)cephalosporin derivatives
EP0150507B1 (en) *	1983-12-29	1992-08-05	Mochida Pharmaceutical Co., Ltd.	Cephalosporin derivatives, processes for producing the same and compositions containing them
AU586215B2 (en) *	1985-01-21	1989-07-06	Nippon Pharmaceutical Development Institute Company Limited	Novel ```-lactam antibiotics
FI872879A7 (fi) *	1986-07-21	1988-01-22	Sankei Yakuhin Kk	--laktamfoerening, foerfarande foer dess framstaellning, denna innehaollande laekemedelskomposition foer behandling av sjukdom med bakterieinfektion samt mellanprodukter foer dess syntes.
DE3840011A1 (de) *	1988-11-26	1990-05-31	Merck Patent Gmbh	Benzoxazinderivate

1988
- 1988-08-03 EP EP19880112640 patent/EP0303172A3/de not_active Withdrawn
- 1988-08-08 AU AU20554/88A patent/AU614984B2/en not_active Ceased
- 1988-08-08 IL IL87374A patent/IL87374A0/xx unknown
- 1988-08-09 US US07/229,960 patent/US5036064A/en not_active Expired - Fee Related
- 1988-08-09 NZ NZ225754A patent/NZ225754A/en unknown
- 1988-08-10 HU HU884144A patent/HUT47944A/hu unknown
- 1988-08-11 MC MC882001A patent/MC1970A1/fr unknown
- 1988-08-12 JP JP63201825A patent/JPS6466190A/ja active Pending
- 1988-08-12 PT PT88274A patent/PT88274B/pt not_active IP Right Cessation
- 1988-08-12 DK DK455288A patent/DK455288A/da not_active Application Discontinuation
- 1988-08-12 PH PH37404A patent/PH25646A/en unknown
- 1988-08-12 YU YU01563/88A patent/YU156388A/xx unknown
- 1988-08-12 FI FI883766A patent/FI883766A7/fi not_active IP Right Cessation
- 1988-08-12 NO NO88883590A patent/NO883590L/no unknown
- 1988-08-13 KR KR1019880010328A patent/KR890003776A/ko not_active Withdrawn
1992
- 1992-05-19 US US07/885,581 patent/US5319140A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US5319140A (en)	1994-06-07
NZ225754A (en)	1991-04-26
EP0303172A2 (de)	1989-02-15
JPS6466190A (en)	1989-03-13
AU614984B2 (en)	1991-09-19
PH25646A (en)	1991-08-21
MC1970A1 (fr)	1989-09-29
EP0303172A3 (de)	1991-05-15
YU156388A (en)	1990-02-28
DK455288D0 (da)	1988-08-12
DK455288A (da)	1989-02-15
PT88274A (pt)	1989-06-30
IL87374A0 (en)	1989-01-31
HUT47944A (en)	1989-04-28
FI883766A7 (fi)	1989-02-15
PT88274B (pt)	1995-03-01
FI883766A0 (fi)	1988-08-12
NO883590D0 (no)	1988-08-12
AU2055488A (en)	1989-04-20
KR890003776A (ko)	1989-04-18
US5036064A (en)	1991-07-30

Publication	Publication Date	Title
NO883590L (no)	1989-02-15	Acylderivater.
NO881531L (no)	1988-10-11	Acylderivater.
NO780074L (no)	1978-08-14	Fremgangsmaate ved fremstilling av derivater av 7-acylamido-3-cefem-4-karboksylsyre
US4254119A (en)	1981-03-03	3-Unsubstituted-3-cephem compounds
NO763601L (da)	1977-04-26
NZ245200A (en)	1995-08-28	Cephalosporin derivatives, medicaments and intermediate compounds
AU672675B2 (en)	1996-10-10	Thiazolopyrimidine derivatives
NO170021B (no)	1992-05-25	Analogifremgangsmaate ved fremstilling av terapeutisk aktive 3-propenylcefem-derivater
US5138066A (en)	1992-08-11	Intermediates for cephalosporins with sulfur-containing oxyimino side chain
DK165836B (da)	1993-01-25	Fremgangsmaade til fremstilling af cephemforbindelser
NO774180L (no)	1978-06-09	Fremgangsmaate for fremstilling av cefalosporin- og penicillinderivater
US5073550A (en)	1991-12-17	Cephalosphorins with sulfur-containing oxyimino side chain
FI66619C (fi)	1984-11-12	Foerfarande foer framstaellning av farmaceutiskt anvaendbara 7beta-(d-2-amino-2-(laogalkylsulfonylaminofenyl)-asetylamino)-3-r-3-cefem-4-karboxylsyror
GB1568962A (en)	1980-06-11	Reparation and compositions containing them (heterocyclic-carbonylamino)pencillins methods for their p
NO763600L (da)	1977-04-26
JPS6118785A (ja)	1986-01-27	ペネム誘導体
PT92890A (pt)	1990-07-31	Processo para a preparacao de derivados de cefalosporina e de composicoes farmaceuticas que os contem
KR970004049B1 (ko)	1997-03-24	세팔로스포린 유도체
NO171502B (no)	1992-12-14	Analogifremgangsmaate for fremstilling av terapeutisk aktive thiadiazolylacetamidcefem-derivater
AU746732B2 (en)	2002-05-02	Novel cephalosporin compounds, processes for preparation thereof and antimicrobial compositions containing the same
NO763602L (da)	1977-04-26
JPH01216997A (ja)	1989-08-30	新規セフェム化合物ならびにその製造法
DK159157B (da)	1990-09-10	Krystallinske 3-hydroxy-cephalosporin-solvater
KR790001400B1 (ko)	1979-10-02	페니실린의제법
NO841791L (no)	1984-11-08	Fremgangsmaate for fremstilling av cephem-forbindelser