CA1268763A - Esters 3-acylamino-2-oxo-1-azetidinyliques d'acides phosphoniques; esters d'acide phosphorique - Google Patents

Esters 3-acylamino-2-oxo-1-azetidinyliques d'acides phosphoniques; esters d'acide phosphorique

Info

Publication number: CA1268763A
Authority: CA; Canada
Prior art keywords: substituted; alkyl; phenyl; amino; hydrogen
Prior art date: 1982-09-27
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 - Fee Related

Application number

CA000595565A

Other languages

English (en)

Inventor

William A. Slusarchyk

Tamara Dejneka

William H. Koster

Eric M. Gordon

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.)

ER Squibb and Sons LLC

Original Assignee

ER Squibb and Sons LLC

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.)

1982-09-27

Filing date

1989-04-03

Publication date

1990-05-08

1982-09-27 Priority claimed from US06/424,132 external-priority patent/US4681937A/en

1989-04-03 Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC

1989-04-03 Priority to CA000595565A priority Critical patent/CA1268763A/fr

1990-05-08 Application granted granted Critical

1990-05-08 Publication of CA1268763A publication Critical patent/CA1268763A/fr

2007-05-08 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000003009 phosphonic acids Chemical class 0.000 title description 2
150000003014 phosphoric acid esters Chemical class 0.000 title description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title 2
229910000147 aluminium phosphate Inorganic materials 0.000 title 1
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
239000001257 hydrogen Substances 0.000 claims abstract description 41
150000003839 salts Chemical class 0.000 claims abstract description 35
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 28
-1 2-phenylethenyl Chemical group 0.000 claims description 158
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 84
125000000217 alkyl group Chemical group 0.000 claims description 65
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
125000004432 carbon atom Chemical group C* 0.000 claims description 30
125000000547 substituted alkyl group Chemical group 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
125000004093 cyano group Chemical group *C#N 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 19
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
125000001589 carboacyl group Chemical group 0.000 claims description 15
125000000623 heterocyclic group Chemical group 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
125000003884 phenylalkyl group Chemical group 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
150000001721 carbon Chemical group 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
125000000168 pyrrolyl group Chemical group 0.000 claims description 6
125000003831 tetrazolyl group Chemical group 0.000 claims description 6
125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
125000000335 thiazolyl group Chemical group 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 5
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 5
125000004442 acylamino group Chemical group 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
125000002883 imidazolyl group Chemical group 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
125000004306 triazinyl group Chemical group 0.000 claims description 5
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000005236 alkanoylamino group Chemical group 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 3
125000006371 dihalo methyl group Chemical group 0.000 claims description 3
125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
125000004970 halomethyl group Chemical group 0.000 claims description 3
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 3
125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 claims description 3
125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
125000000160 oxazolidinyl group Chemical group 0.000 claims description 3
125000003566 oxetanyl group Chemical group 0.000 claims description 3
125000002071 phenylalkoxy group Chemical group 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000002053 thietanyl group Chemical group 0.000 claims description 3
125000004953 trihalomethyl group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims 8
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 4
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 1
125000004043 oxo group Chemical group O=* 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
125000002252 acyl group Chemical group 0.000 abstract description 12
239000000543 intermediate Substances 0.000 abstract description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 5
238000002360 preparation method Methods 0.000 abstract description 2
230000000845 anti-microbial effect Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 73
150000001875 compounds Chemical class 0.000 description 44
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 25
239000000047 product Substances 0.000 description 23
239000000243 solution Substances 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000011347 resin Substances 0.000 description 12
229920005989 resin Polymers 0.000 description 12
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 11
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 8
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
229920001467 poly(styrenesulfonates) Polymers 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000007836 KH2PO4 Substances 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
238000004108 freeze drying Methods 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
229910000402 monopotassium phosphate Inorganic materials 0.000 description 6
235000019796 monopotassium phosphate Nutrition 0.000 description 6
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 6
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
239000012043 crude product Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 5
CAAULPUQFIIOTL-UHFFFAOYSA-L methyl phosphate(2-) Chemical compound COP([O-])([O-])=O CAAULPUQFIIOTL-UHFFFAOYSA-L 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
239000007787 solid Substances 0.000 description 5
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000003368 amide group Chemical group 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
239000003782 beta lactam antibiotic agent Substances 0.000 description 4
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
SCLFRABIDYGTAZ-UHFFFAOYSA-N methylphosphonic acid dichloride Chemical compound CP(Cl)(Cl)=O SCLFRABIDYGTAZ-UHFFFAOYSA-N 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229940024606 amino acid Drugs 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000013058 crude material Substances 0.000 description 3
125000000392 cycloalkenyl group Chemical group 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
125000001841 imino group Chemical group [H]N=* 0.000 description 3
150000002960 penicillins Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
208000035143 Bacterial infection Diseases 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
WTPZDQICVMWKED-UHFFFAOYSA-N FC(C(=O)O)(F)F.CP(O)(O)=O Chemical compound FC(C(=O)O)(F)F.CP(O)(O)=O WTPZDQICVMWKED-UHFFFAOYSA-N 0.000 description 2
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 2
241000124008 Mammalia Species 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
239000000872 buffer Substances 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
125000004966 cyanoalkyl group Chemical group 0.000 description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000002024 ethyl acetate extract Substances 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
230000026731 phosphorylation Effects 0.000 description 2
238000006366 phosphorylation reaction Methods 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
125000004149 thio group Chemical group *S* 0.000 description 2
LLHOYOCAAURYRL-RITPCOANSA-N (2s,3r)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)OC(C)(C)C LLHOYOCAAURYRL-RITPCOANSA-N 0.000 description 1
NLARCUDOUOQRPB-WTKPLQERSA-N (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetic acid Chemical compound CO\N=C(/C(O)=O)C1=CSC(N)=N1 NLARCUDOUOQRPB-WTKPLQERSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
NDVMCQUOSYOQMZ-UHFFFAOYSA-N 2,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)C(C(N)=O)[Si](C)(C)C NDVMCQUOSYOQMZ-UHFFFAOYSA-N 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 1
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241000283690 Bos taurus Species 0.000 description 1
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241000282472 Canis lupus familiaris Species 0.000 description 1
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241000283086 Equidae Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
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239000004472 Lysine Substances 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
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229910003849 O-Si Inorganic materials 0.000 description 1
241001648341 Orites Species 0.000 description 1
229910003872 O—Si Inorganic materials 0.000 description 1
206010057190 Respiratory tract infections Diseases 0.000 description 1
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KUOXWPCYGDJLBQ-UHFFFAOYSA-N acetic acid methylphosphonic acid Chemical compound C(C)(=O)O.CP(O)(O)=O KUOXWPCYGDJLBQ-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
125000005276 alkyl hydrazino group Chemical group 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
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239000003242 anti bacterial agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000012062 aqueous buffer Substances 0.000 description 1
239000012223 aqueous fraction Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000010936 aqueous wash Methods 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
125000005100 aryl amino carbonyl group Chemical group 0.000 description 1
125000004658 aryl carbonyl amino group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
LXWBXEWUSAABOA-VXSYNFHWSA-N cephamycin C Chemical compound S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)[C@@](OC)(NC(=O)CCC[C@@H](N)C(O)=O)[C@H]21 LXWBXEWUSAABOA-VXSYNFHWSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
KLKYJMASALXYQR-UHFFFAOYSA-L dipotassium;methyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [K+].[K+].CP([O-])([O-])=O KLKYJMASALXYQR-UHFFFAOYSA-L 0.000 description 1
CDMADVZSLOHIFP-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane;decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 CDMADVZSLOHIFP-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
150000002390 heteroarenes Chemical class 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical class C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
DCPMPXBYPZGNDC-UHFFFAOYSA-N hydron;methanediimine;chloride Chemical compound Cl.N=C=N DCPMPXBYPZGNDC-UHFFFAOYSA-N 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000595565A 1982-09-27 1989-04-03 Esters 3-acylamino-2-oxo-1-azetidinyliques d'acides phosphoniques; esters d'acide phosphorique Expired - Fee Related CA1268763A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000595565A CA1268763A (fr)	1982-09-27	1989-04-03	Esters 3-acylamino-2-oxo-1-azetidinyliques d'acides phosphoniques; esters d'acide phosphorique

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US06/424,132 US4681937A (en)	1982-09-27	1982-09-27	3-acylamino-2-oxo-1-azetidinyl esters of phosphonic acids, phosphoric acid and phosphoric acid esters
US424,132		1982-09-27
CA 435268 CA1268763C (fr)	1982-09-27	1983-08-24	Esters 3-acylamino-2-oxo-1-azetidinyliques d'acides phosphoniques; esters d'acide phosphorique
CA000595565A CA1268763A (fr)	1982-09-27	1989-04-03	Esters 3-acylamino-2-oxo-1-azetidinyliques d'acides phosphoniques; esters d'acide phosphorique

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 435268 Division CA1268763C (fr)	1982-09-27	1983-08-24	Esters 3-acylamino-2-oxo-1-azetidinyliques d'acides phosphoniques; esters d'acide phosphorique

Publications (1)

Publication Number	Publication Date
CA1268763A true CA1268763A (fr)	1990-05-08

Family

ID=25670132

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000595565A Expired - Fee Related CA1268763A (fr)	1982-09-27	1989-04-03	Esters 3-acylamino-2-oxo-1-azetidinyliques d'acides phosphoniques; esters d'acide phosphorique

Country Status (1)

Country	Link
CA (1)	CA1268763A (fr)

1989
- 1989-04-03 CA CA000595565A patent/CA1268763A/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1992-11-10	MKLA	Lapsed

Publication	Publication Date	Title
EP0051381B1 (fr)	1985-01-30	Acides bêta-lactame hydroxamiques 0-sulfatés
US4939253A (en)	1990-07-03	2-oxoazetidin-1-yloxy acetic acids and analogs
US4670553A (en)	1987-06-02	2-oxo-1-(aminocarbonylaminosulfonyl-aminocarbonyl)azetidines
EP0085291B1 (fr)	1988-08-17	2-Oxo-1-(aminocarbonylaminosulfonylaminocarbonyl)-azétidines
US4534896A (en)	1985-08-13	3-Acylamino-2-oxoazetidine-1-(β-oxopropionic acid)
US4559335A (en)	1985-12-17	3-Acylamino-1-carboxymethyloxy (or thio) carbonyl-2-azetidinones
US4533660A (en)	1985-08-06	Antibacterial O-sulfated β-lactam hydroxamic acids
US4478749A (en)	1984-10-23	2-Oxo-1-(substituted phosphorous)azetidines
EP0243924B1 (fr)	1992-12-23	Azétidines 2-oxo, substituées en 1 par un groupe phosphoreux substitué
CA1268763A (fr)	1990-05-08	Esters 3-acylamino-2-oxo-1-azetidinyliques d'acides phosphoniques; esters d'acide phosphorique
US4681937A (en)	1987-07-21	3-acylamino-2-oxo-1-azetidinyl esters of phosphonic acids, phosphoric acid and phosphoric acid esters
CA1253502A (fr)	1989-05-02	Sels de l'acide 4-[[(amidomethyl)oxy]methyl]- 2-oxo-1-azetidinesulfonique
KR900005132B1 (ko)	1990-07-20	아제티디닐 술폰산 및 그의 유도체
US4548751A (en)	1985-10-22	(2-Oxo-1-azetidinyloxy)-2-propenoic acid
US4734496A (en)	1988-03-29	4-amino derivatives of 2-oxo-1-azetidinesulfonic acid salts
US4551277A (en)	1985-11-05	4-(3-Acylamino-2-oxo-1-azetidinyl)-4-oxo-2-butenoic acid
EP0124123B1 (fr)	1989-04-19	3-Acylamine-1-sulphonylaminocarbonylméthoxy-2-azétidinones
US4551276A (en)	1985-11-05	2-Oxoazetidin-1-yloxymethyl sulfonic acid and analogs
EP0127177B1 (fr)	1988-12-21	Acides [[(acylamino-3-oxo-2-azétidinyl-1)oxy]méthyl]phosphiniques
US4670554A (en)	1987-06-02	((3-Acylamino-2-oxo-1-azetidinyl)oxy)methyl)phosphinic acids
CA1243679A (fr)	1988-10-25	3-ACYLAMINO-2-OXO-1-AZETIDINYL-.beta.-OXYPROPIONATES
EP0135814A1 (fr)	1985-04-03	1-(1H-tétrazol-5-yl-alcoxy)-2-azétidinones
FR2552757A1 (fr)	1985-04-05	Procede de production de bromoacenaphtylene condense
EP0344707A2 (fr)	1989-12-06	Dérivés de 2-oxo-azétidines portant en 1 un groupe [[(sulphonyl substitué)-amino]carbonyle]