CS213385B2 - Method of making the new oxime derivatives of the 3-azidomethyl-7-aminothiazolylacetamidocephalospooran acid - Google Patents

Method of making the new oxime derivatives of the 3-azidomethyl-7-aminothiazolylacetamidocephalospooran acid Download PDF

Info

Publication number: CS213385B2
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; compound; acid; hydrogen
Prior art date: 1978-04-14

Application number

CS792474A

Other languages

Czech (cs)

English (en)

Inventor

Rene Heymer

Andre Lutz

Original Assignee

Roussel Uclaf

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.)

1978-04-14

Filing date

1979-04-11

Publication date

1982-04-09

1978-04-14 Priority claimed from FR7811065A external-priority patent/FR2422668A1/fr

1978-10-05 Priority claimed from FR7828465A external-priority patent/FR2438051A2/fr

1979-04-11 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1982-04-09 Publication of CS213385B2 publication Critical patent/CS213385B2/cs

Links

239000002253 acid Substances 0.000 title claims abstract description 56
150000002923 oximes Chemical class 0.000 title claims abstract description 4
238000004519 manufacturing process Methods 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 33
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
238000000034 method Methods 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 16
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 10
150000001340 alkali metals Chemical class 0.000 claims abstract description 10
125000004185 ester group Chemical group 0.000 claims abstract description 10
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 9
150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 114
-1 amine organic base Chemical class 0.000 claims description 109
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
239000000203 mixture Substances 0.000 claims description 26
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
150000002148 esters Chemical class 0.000 claims description 23
150000007524 organic acids Chemical class 0.000 claims description 18
150000007522 mineralic acids Chemical class 0.000 claims description 15
239000003795 chemical substances by application Substances 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
239000000243 solution Substances 0.000 claims description 12
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
235000005985 organic acids Nutrition 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 10
159000000000 sodium salts Chemical class 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 9
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 7
239000007864 aqueous solution Substances 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
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 2
125000006242 amine protecting group Chemical group 0.000 claims 1
150000003585 thioureas Chemical class 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 abstract description 8
230000003115 biocidal effect Effects 0.000 abstract description 6
150000007513 acids Chemical class 0.000 abstract description 5
150000001412 amines Chemical class 0.000 abstract description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract description 2
231100000252 nontoxic Toxicity 0.000 abstract 2
230000003000 nontoxic effect Effects 0.000 abstract 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
229910052749 magnesium Inorganic materials 0.000 abstract 1
239000011777 magnesium Substances 0.000 abstract 1
125000004417 unsaturated alkyl group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 22
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235000019441 ethanol Nutrition 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000010521 absorption reaction Methods 0.000 description 15
239000000126 substance Substances 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
235000019253 formic acid Nutrition 0.000 description 11
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
241000588724 Escherichia coli Species 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 10
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 9
229930182566 Gentamicin Natural products 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
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238000003756 stirring Methods 0.000 description 9
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 8
241000191967 Staphylococcus aureus Species 0.000 description 8
229930182555 Penicillin Natural products 0.000 description 7
150000001540 azides Chemical class 0.000 description 7
239000002585 base Substances 0.000 description 7
125000005935 hexyloxycarbonyl group Chemical group 0.000 description 7
229940049954 penicillin Drugs 0.000 description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000004098 Tetracycline Substances 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
201000010099 disease Diseases 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
125000001841 imino group Chemical group [H]N=* 0.000 description 6
239000000463 material Substances 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
229960002180 tetracycline Drugs 0.000 description 6
229930101283 tetracycline Natural products 0.000 description 6
235000019364 tetracycline Nutrition 0.000 description 6
150000003522 tetracyclines Chemical class 0.000 description 6
241000894006 Bacteria Species 0.000 description 5
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
241000588748 Klebsiella Species 0.000 description 5
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
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241000295644 Staphylococcaceae Species 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
230000008030 elimination Effects 0.000 description 5
238000003379 elimination reaction Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
235000011181 potassium carbonates Nutrition 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
239000001632 sodium acetate Substances 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
241000607142 Salmonella Species 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
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238000002329 infrared spectrum Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
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WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 3
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244000063299 Bacillus subtilis Species 0.000 description 3
235000014469 Bacillus subtilis Nutrition 0.000 description 3
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241000194032 Enterococcus faecalis Species 0.000 description 3
241000588769 Proteus <enterobacteria> Species 0.000 description 3
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239000004480 active ingredient Substances 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
244000052616 bacterial pathogen Species 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
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ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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BFICUYMMIFCNTD-UHFFFAOYSA-N ethyl 2-(2-bromoethoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate Chemical compound BrCCON=C(C(=O)OCC)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 BFICUYMMIFCNTD-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
229960002518 gentamicin Drugs 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
NZDJTVSTIFYISQ-UHFFFAOYSA-N iodomethyl acetate Chemical compound CC(=O)OCI NZDJTVSTIFYISQ-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
XHQZJYCNDZAGLW-UHFFFAOYSA-N meta-methoxylbenzoic acid Natural products COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
229950009215 phenylbutanoic acid Drugs 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
238000005201 scrubbing Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008221 sterile excipient Substances 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
239000000829 suppository Substances 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 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
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- C07D277/587—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 aliphatic hydrocarbon radicals substituted by 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, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS792474A 1978-04-14 1979-04-11 Method of making the new oxime derivatives of the 3-azidomethyl-7-aminothiazolylacetamidocephalospooran acid CS213385B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7811065A FR2422668A1 (fr)	1978-04-14	1978-04-14	Nouvelles oximes derivees de l'acide 3-azidomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments
FR7828465A FR2438051A2 (fr)	1978-10-05	1978-10-05	Nouvelles oximes derivees de l'acide 3-azidomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments

Publications (1)

Publication Number	Publication Date
CS213385B2 true CS213385B2 (en)	1982-04-09

Family

ID=26220553

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS792474A CS213385B2 (en)	1978-04-14	1979-04-11	Method of making the new oxime derivatives of the 3-azidomethyl-7-aminothiazolylacetamidocephalospooran acid

Country Status (21)

Country	Link
US (1)	US4420478A (fr)
AT (1)	AT365198B (fr)
AU (1)	AU4605279A (fr)
CH (1)	CH640858A5 (fr)
CS (1)	CS213385B2 (fr)
DD (1)	DD143260A5 (fr)
DE (1)	DE2914827A1 (fr)
DK (1)	DK150879A (fr)
ES (2)	ES479552A1 (fr)
FI (1)	FI791183A7 (fr)
GB (1)	GB2018758B (fr)
GR (1)	GR73581B (fr)
IL (1)	IL57064A0 (fr)
IT (1)	IT1164673B (fr)
LU (1)	LU81156A1 (fr)
NL (1)	NL7902922A (fr)
NO (1)	NO791218L (fr)
OA (1)	OA06223A (fr)
PL (1)	PL214880A1 (fr)
PT (1)	PT69490A (fr)
SE (1)	SE445350B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2476647A2 (fr) *	1980-02-26	1981-08-28	Roussel Uclaf	Procede de preparation de derives de l'acide 2-(2-amino protege 4-thiazolyl) 2-alkoxyimino acetique isomere syn
US4487768A (en) *	1982-12-22	1984-12-11	Fujisawa Pharmaceutical Co., Ltd.	Cephem compounds
US4521598A (en) *	1983-09-28	1985-06-04	Eli Lilly And Company	3-Azidocephalosporins
AU1630988A (en) *	1987-05-30	1988-12-01	Kyoto Pharmaceutical Industries, Ltd.	Cephalosporin compound and pharmaceutical composition thereof
JOP20200093A1 (ar) *	2015-01-09	2017-06-16	Kyowa Kirin Co Ltd	طريقة لإنتاج مشتق ثيازول
CN106977405A (zh) *	2017-04-17	2017-07-25	安徽广信农化股份有限公司	一种噁草酮中间体硝基苯酚的合成系统

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1399086A (en) *	1971-05-14	1975-06-25	Glaxo Lab Ltd	Cephalosporin compounds
US4076936A (en) *	1973-07-06	1978-02-28	Glaxo Laboratories Limited	7β-(2-Aryl-2-hydroxyiminoacetamido)ceph-3-em-4-carboxylic acids carrying a 7α-lower alkoxy substituent
DK154939C (da) *	1974-12-19	1989-06-12	Takeda Chemical Industries Ltd	Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf
SE440655B (sv) *	1976-01-23	1985-08-12	Roussel Uclaf	Sett att framstella nya oximderivat av 7-amino-tiazolyl-acetamido-cefalosporansyra
FR2361895A1 (fr) *	1976-08-20	1978-03-17	Roussel Uclaf	Nouvelles oximes derivees de l'acide 3-carbamoyloxymethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments

1979
- 1979-03-14 SE SE7902286A patent/SE445350B/sv not_active IP Right Cessation
- 1979-03-31 OA OA56774A patent/OA06223A/fr unknown
- 1979-04-06 GR GR58820A patent/GR73581B/el unknown
- 1979-04-09 US US06/028,372 patent/US4420478A/en not_active Expired - Lifetime
- 1979-04-10 NO NO791218A patent/NO791218L/no unknown
- 1979-04-11 DE DE19792914827 patent/DE2914827A1/de not_active Withdrawn
- 1979-04-11 CS CS792474A patent/CS213385B2/cs unknown
- 1979-04-11 ES ES479552A patent/ES479552A1/es not_active Expired
- 1979-04-11 IL IL57064A patent/IL57064A0/xx unknown
- 1979-04-11 FI FI791183A patent/FI791183A7/fi not_active Application Discontinuation
- 1979-04-11 DK DK150879A patent/DK150879A/da not_active Application Discontinuation
- 1979-04-12 PT PT69490A patent/PT69490A/fr unknown
- 1979-04-12 NL NL7902922A patent/NL7902922A/xx not_active Application Discontinuation
- 1979-04-12 CH CH355879A patent/CH640858A5/fr not_active IP Right Cessation
- 1979-04-12 AT AT0276479A patent/AT365198B/de not_active IP Right Cessation
- 1979-04-12 AU AU46052/79A patent/AU4605279A/en not_active Abandoned
- 1979-04-13 IT IT48726/79A patent/IT1164673B/it active
- 1979-04-13 LU LU81156A patent/LU81156A1/fr unknown
- 1979-04-13 PL PL21488079A patent/PL214880A1/xx unknown
- 1979-04-16 DD DD79212244A patent/DD143260A5/de unknown
- 1979-04-17 GB GB7913258A patent/GB2018758B/en not_active Expired
- 1979-09-17 ES ES484224A patent/ES484224A1/es not_active Expired

Also Published As

Publication number	Publication date
IT7948726A0 (it)	1979-04-13
ES479552A1 (es)	1979-12-16
SE7902286L (sv)	1979-10-15
NO791218L (no)	1979-10-16
SE445350B (sv)	1986-06-16
PL214880A1 (fr)	1980-02-25
CH640858A5 (fr)	1984-01-31
GB2018758A (en)	1979-10-24
GB2018758B (en)	1983-01-12
DE2914827A1 (de)	1979-10-18
FI791183A7 (fi)	1981-01-01
PT69490A (fr)	1979-05-01
AT365198B (de)	1981-12-28
ATA276479A (de)	1981-05-15
DD143260A5 (de)	1980-08-13
NL7902922A (nl)	1979-10-16
DK150879A (da)	1979-10-15
ES484224A1 (es)	1980-05-16
AU4605279A (en)	1979-10-18
OA06223A (fr)	1981-06-30
GR73581B (fr)	1984-03-21
IL57064A0 (en)	1979-07-25
IT1164673B (it)	1987-04-15
LU81156A1 (fr)	1979-11-07
US4420478A (en)	1983-12-13

Publication	Publication Date	Title
US4476122A (en)	1984-10-09	Alkyloximes of 7-amino-thiazolyl-acetamido-cephalosporanic acids
NL192041C (nl)	1997-01-07	Geneesmiddel met antibacteriële werking, alsmede 7-£2-(2-aminothiazool-4-yl)-2-(veretherd oxyimino)-aceetamido\|-3-cefem -4-carbonzuurderivaten.
US4202893A (en)	1980-05-13	Alkyloximes of 7-amino-thiazolyl-acetamido-cephalosporanic acids
FR2476087A1 (fr)	1981-08-21	Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkyl-thiomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments
JPS6228152B2 (fr)	1987-06-18
NO165027B (no)	1990-09-03	Analogifremgangsmaate for fremstilling av terapeutisk aktive propenyl-cefalosporinforbindelser.
US4097595A (en)	1978-06-27	7-Amino-thiazolyl acetamido cephalosporanic acids
JPS638117B2 (fr)	1988-02-19
IE48942B1 (en)	1985-06-26	3-unsubstituted-3-cephem compounds
CS213385B2 (en)	1982-04-09	Method of making the new oxime derivatives of the 3-azidomethyl-7-aminothiazolylacetamidocephalospooran acid
CH638221A5 (fr)	1983-09-15	Oximes derivees de l'acide 3-substitue 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et les compositions pharmaceutiques les renfermant.
KR840002163B1 (ko)	1984-11-24	7-β-[α-syn-메톡시이미노-α-(2-아미노티아졸-4-일)-아세트 아미도]-3-[(1,2,3-티아디아졸-5-일) 티오메틸]-3-세펨-4-카르복시산 및 C_1-C_6 알킬 유도체 제조방법.
GB2098217A (en)	1982-11-17	New 2-aminothiazolyl-2-oxyiminoacetamido bicyclooctene carboxylic acid compounds their preparation their compositions and their use as medicaments
HU184805B (en)	1984-10-29	Process for preparing new substituted alkyl-oximes derived from 7-/2-amino-4-thazolyl/-acetamido-cephalosporanic acid
CH639388A5 (fr)	1983-11-15	Cephalosporines derivees de l'acide 7-/2-(2-amino 4-thiazolyl) 2-(carboxymethoxyimino) acetamido/ 3-substitue cephalosporanique, leurs procedes de preparation et medicaments les renfermant.
CA1152061A (fr)	1983-08-16	Procede de preparation de nouvelles oximes o-substituees derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique
US4018921A (en)	1977-04-19	Substituted phenylglycylcephalosporins
HU181961B (en)	1983-11-28	Process for producing new oxime derivatives of 3-thiadiazolythio-methyl-7-aminothiazolylacetamido-ceph-3-eme-4-carboxylic acids
US4033956A (en)	1977-07-05	7[α-Amino-ω-(2,3-methylenedioxy-phenyl)acylamido]cephalosporanic acid derivatives
US4172941A (en)	1979-10-30	7-[2-[ω-(1,3-Dithiolan-2-imino)substituted]-acetylamino]cephalosporanic acid derivatives
US4016158A (en)	1977-04-05	Cephalosporin derivatives
EP0122154A2 (fr)	1984-10-17	Dérivés de benzothiénylglycylcéphalosporine
IE43376B1 (en)	1981-02-11	7-/ -amino-w-(3,4-methylenedioxyphenyl) acylamido/cephalosporanic acid derivatives
FR2499995A1 (fr)	1982-08-20	Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkylthiomethyl 7-amino thiazolylacetamido cephalosporanique, leur preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus.
CS209879B2 (cs)	1981-12-31	Způsob výroby nových alkyloximových derivátů kyseliny 7- [ 2- (2-amíno-4-thiazolyljacetamido] cefalosporanové