IE52580B1 - Azetidinone compounds and their preparation - Google Patents
Azetidinone compounds and their preparationInfo
- Publication number
- IE52580B1 IE52580B1 IE516/82A IE51682A IE52580B1 IE 52580 B1 IE52580 B1 IE 52580B1 IE 516/82 A IE516/82 A IE 516/82A IE 51682 A IE51682 A IE 51682A IE 52580 B1 IE52580 B1 IE 52580B1
- Authority
- IE
- Ireland
- Prior art keywords
- oxo
- formula
- methyl
- azetidinyl
- group
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract description 11
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title description 5
- -1 carboxy-substituted butenyl group Chemical group 0.000 claims abstract description 91
- RFGZYLNEARMOGP-UHFFFAOYSA-N 4-fluoroazetidin-2-one Chemical class FC1CC(=O)N1 RFGZYLNEARMOGP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 6
- 125000003368 amide group Chemical group 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- XHFXMNZYIKFCPN-UHFFFAOYSA-N perchloryl fluoride Chemical compound FCl(=O)(=O)=O XHFXMNZYIKFCPN-UHFFFAOYSA-N 0.000 claims description 12
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 claims description 3
- GCBWDZYSLVSRRI-UHFFFAOYSA-N 3-aminoazetidin-2-one Chemical compound NC1CNC1=O GCBWDZYSLVSRRI-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- PVEOYINWKBTPIZ-UHFFFAOYSA-M but-3-enoate Chemical class [O-]C(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-M 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Chemical group 0.000 claims description 3
- ANJHTLZWTYGNKM-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-[2-fluoro-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]-3-methylbut-2-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(=C(C)C)N(C1=O)C(F)C1NC(=O)COC1=CC=CC=C1 ANJHTLZWTYGNKM-UHFFFAOYSA-N 0.000 claims description 2
- UUFYUDGFKQGFIY-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-[2-fluoro-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(C(=C)C)N(C1=O)C(F)C1NC(=O)COC1=CC=CC=C1 UUFYUDGFKQGFIY-UHFFFAOYSA-N 0.000 claims description 2
- MSZRNTXTMAAYGY-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-[3-(1,3-dioxoisoindol-2-yl)-2-fluoro-4-oxoazetidin-1-yl]-3-methylbut-3-enoate Chemical compound FC1C(N2C(C3=CC=CC=C3C2=O)=O)C(=O)N1C(C(=C)C)C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 MSZRNTXTMAAYGY-UHFFFAOYSA-N 0.000 claims description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- LXKZQNQBTPSVDI-UHFFFAOYSA-N 1-[3-methyl-1-[(4-nitrophenyl)methoxy]-1-oxobut-3-en-2-yl]-4-oxo-3-[(2-phenoxyacetyl)amino]azetidine-2-sulfinic acid Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(C(=C)C)N(C1=O)C(S(O)=O)C1NC(=O)COC1=CC=CC=C1 LXKZQNQBTPSVDI-UHFFFAOYSA-N 0.000 claims description 2
- FPZDNWDLRIUPDI-UHFFFAOYSA-N 2,2,2-trichloroethyl 2-[2-fluoro-4-oxo-3-[(2-thiophen-2-ylacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate Chemical compound O=C1N(C(C(=C)C)C(=O)OCC(Cl)(Cl)Cl)C(F)C1NC(=O)CC1=CC=CS1 FPZDNWDLRIUPDI-UHFFFAOYSA-N 0.000 claims description 2
- MGTKVFGCLTZFBN-UHFFFAOYSA-N 2-[2-fluoro-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoic acid Chemical compound O=C1N(C(C(=C)C)C(O)=O)C(F)C1NC(=O)COC1=CC=CC=C1 MGTKVFGCLTZFBN-UHFFFAOYSA-N 0.000 claims description 2
- ANSXQSSHZVOBIL-UHFFFAOYSA-N 2-[2-fluoro-4-oxo-3-[(2-thiophen-2-ylacetyl)amino]azetidin-1-yl]-3-methylbut-2-enoic acid Chemical compound O=C1N(C(=C(C)C)C(O)=O)C(F)C1NC(=O)CC1=CC=CS1 ANSXQSSHZVOBIL-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- FVHOSELPFQDVNU-UHFFFAOYSA-N benzhydryl 2-[2-fluoro-3-[(4-methylbenzoyl)amino]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(=O)C(C(=C)C)N(C1=O)C(F)C1NC(=O)C1=CC=C(C)C=C1 FVHOSELPFQDVNU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 2
- 239000011591 potassium Chemical group 0.000 claims description 2
- 229910052700 potassium Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- CIUHMIBWSMMGET-UHFFFAOYSA-N (4-methoxyphenyl)methyl 2-(3-amino-2-fluoro-4-oxoazetidin-1-yl)-3-methylbut-3-enoate Chemical compound C1=CC(OC)=CC=C1COC(=O)C(C(C)=C)N1C(=O)C(N)C1F CIUHMIBWSMMGET-UHFFFAOYSA-N 0.000 claims 1
- YKFYAXLHEGAOTH-UHFFFAOYSA-N (4-methoxyphenyl)methyl 2-[2-fluoro-4-oxo-3-(phenylmethoxycarbonylamino)azetidin-1-yl]-3-methylbut-3-enoate Chemical compound C1=CC(OC)=CC=C1COC(=O)C(C(C)=C)N1C(=O)C(NC(=O)OCC=2C=CC=CC=2)C1F YKFYAXLHEGAOTH-UHFFFAOYSA-N 0.000 claims 1
- WFFWMCNXTJIHMU-UHFFFAOYSA-N 2,2,2-trichloroethyl 2-[2-fluoro-4-oxo-3-[(2-thiophen-2-ylacetyl)amino]azetidin-1-yl]-3-methylbut-2-enoate Chemical compound O=C1N(C(=C(C)C)C(=O)OCC(Cl)(Cl)Cl)C(F)C1NC(=O)CC1=CC=CS1 WFFWMCNXTJIHMU-UHFFFAOYSA-N 0.000 claims 1
- QDSCLYIXXGXXHM-UHFFFAOYSA-N 2-[2-fluoro-4-(oxaldehydoylamino)-3-phenylazetidin-1-yl]-3-methylbut-3-enoic acid Chemical compound O=CC(=O)NC1N(C(C(=C)C)C(O)=O)C(F)C1C1=CC=CC=C1 QDSCLYIXXGXXHM-UHFFFAOYSA-N 0.000 claims 1
- 206010007134 Candida infections Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 6
- 229930182555 Penicillin Natural products 0.000 abstract description 4
- 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 abstract description 3
- 229940049954 penicillin Drugs 0.000 abstract description 3
- 239000003782 beta lactam antibiotic agent Substances 0.000 abstract description 2
- 239000002132 β-lactam antibiotic Substances 0.000 abstract description 2
- 229940124586 β-lactam antibiotics Drugs 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- 239000002253 acid Substances 0.000 description 11
- 238000006317 isomerization reaction Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 5
- 125000004442 acylamino group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003242 anti bacterial agent Substances 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
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 150000003455 sulfinic acids Chemical class 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IZXITUBKBNCSCK-UHFFFAOYSA-N 2-[2-fluoro-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]-3-methylbut-2-enoic acid Chemical compound O=C1N(C(=C(C)C)C(O)=O)C(F)C1NC(=O)COC1=CC=CC=C1 IZXITUBKBNCSCK-UHFFFAOYSA-N 0.000 description 2
- YFCSNHUPUILNIX-UHFFFAOYSA-N 3-amino-4-fluoroazetidin-2-one Chemical compound NC1C(F)NC1=O YFCSNHUPUILNIX-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- ZRRLCCCOCSDAKF-UHFFFAOYSA-N azetidin-2-one thionyl dichloride Chemical compound ClS(Cl)=O.O=C1CCN1 ZRRLCCCOCSDAKF-UHFFFAOYSA-N 0.000 description 2
- ASZXBENXWJESDF-UHFFFAOYSA-N benzhydryl 2-[2-fluoro-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(=O)C(C(=C)C)N(C1=O)C(F)C1NC(=O)CC1=CC=CC=C1 ASZXBENXWJESDF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 238000005947 deacylation reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical class ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- PLAJFJGVUYYCCG-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-(3-amino-2-fluoro-4-oxoazetidin-1-yl)-3-methylbut-2-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(=C(C)C)N1C(F)C(N)C1=O PLAJFJGVUYYCCG-UHFFFAOYSA-N 0.000 description 1
- XHHHBGMQIWUQSK-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-(3-amino-2-fluoro-4-oxoazetidin-1-yl)-3-methylbut-3-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(C(=C)C)N1C(F)C(N)C1=O XHHHBGMQIWUQSK-UHFFFAOYSA-N 0.000 description 1
- IAMLIWXXCZLVGR-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-[2-fluoro-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxoazetidin-1-yl]-3-methylbut-2-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(=C(C)C)N1C(F)C(NC(=O)OC(C)(C)C)C1=O IAMLIWXXCZLVGR-UHFFFAOYSA-N 0.000 description 1
- FYDVDYOHFXQPBT-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-[3-(2,5-dioxopyrrolidin-1-yl)-2-fluoro-4-oxoazetidin-1-yl]-3-methylbut-2-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(=C(C)C)N(C1=O)C(F)C1N1C(=O)CCC1=O FYDVDYOHFXQPBT-UHFFFAOYSA-N 0.000 description 1
- IGDASZKEZFHJKR-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-[3-[(2-chloroacetyl)amino]-2-fluoro-4-oxoazetidin-1-yl]-3-methylbut-3-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(C(=C)C)N1C(F)C(NC(=O)CCl)C1=O IGDASZKEZFHJKR-UHFFFAOYSA-N 0.000 description 1
- GLHDBEFVSFUQRE-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-[3-[(2-cyanoacetyl)amino]-2-fluoro-4-oxoazetidin-1-yl]-3-methylbut-3-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(C(=C)C)N1C(F)C(NC(=O)CC#N)C1=O GLHDBEFVSFUQRE-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- MUJKKAPBAKVUFG-UHFFFAOYSA-N 1,1-dichloroethane;dichloromethane Chemical compound ClCCl.CC(Cl)Cl MUJKKAPBAKVUFG-UHFFFAOYSA-N 0.000 description 1
- NVUDCOLTISIMFV-UHFFFAOYSA-N 1-[3-methyl-1-[(4-nitrophenyl)methoxy]-1-oxobut-3-en-2-yl]-4-oxo-3-[(2-phenylacetyl)amino]azetidine-2-sulfinic acid Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(C(=C)C)N(C1=O)C(S(O)=O)C1NC(=O)CC1=CC=CC=C1 NVUDCOLTISIMFV-UHFFFAOYSA-N 0.000 description 1
- DNQPQJXIIUZTDI-UHFFFAOYSA-N 1-[3-methyl-1-oxo-1-(2,2,2-trichloroethoxy)but-3-en-2-yl]-4-oxo-3-[(2-thiophen-2-ylacetyl)amino]azetidine-2-sulfinic acid Chemical compound O=C1N(C(C(=C)C)C(=O)OCC(Cl)(Cl)Cl)C(S(O)=O)C1NC(=O)CC1=CC=CS1 DNQPQJXIIUZTDI-UHFFFAOYSA-N 0.000 description 1
- JTFLUJJESVAQGM-UHFFFAOYSA-N 1-aminoazetidin-2-one Chemical compound NN1CCC1=O JTFLUJJESVAQGM-UHFFFAOYSA-N 0.000 description 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- ZBZNRTIQYIGBMT-UHFFFAOYSA-N 2,2,2-trichloroethyl 2-(3-amino-2-fluoro-4-oxoazetidin-1-yl)-3-methylbut-2-enoate Chemical compound ClC(Cl)(Cl)COC(=O)C(=C(C)C)N1C(F)C(N)C1=O ZBZNRTIQYIGBMT-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- BOSSRUCERTWFKY-UHFFFAOYSA-N 2-(3-amino-2-fluoro-4-oxoazetidin-1-yl)-3-methylbut-2-enoic acid Chemical compound CC(C)=C(C(O)=O)N1C(F)C(N)C1=O BOSSRUCERTWFKY-UHFFFAOYSA-N 0.000 description 1
- WPCKVTFGCPYGIY-UHFFFAOYSA-N 2-(3-amino-2-fluoro-4-oxoazetidin-1-yl)-3-methylbut-3-enoic acid Chemical compound CC(=C)C(C(O)=O)N1C(F)C(N)C1=O WPCKVTFGCPYGIY-UHFFFAOYSA-N 0.000 description 1
- JARSEVXIKSLEPE-UHFFFAOYSA-N 2-[2-fluoro-3-[(2-hydroxy-2-phenylacetyl)amino]-4-oxoazetidin-1-yl]-3-methylbut-2-enoic acid Chemical compound O=C1N(C(=C(C)C)C(O)=O)C(F)C1NC(=O)C(O)C1=CC=CC=C1 JARSEVXIKSLEPE-UHFFFAOYSA-N 0.000 description 1
- YWGMTVVBXVHCCZ-UHFFFAOYSA-N 2-[2-fluoro-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-3-methylbut-2-enoic acid Chemical compound O=C1N(C(=C(C)C)C(O)=O)C(F)C1NC(=O)CC1=CC=CC=C1 YWGMTVVBXVHCCZ-UHFFFAOYSA-N 0.000 description 1
- JUGAQLJUOITKIG-UHFFFAOYSA-N 2-[3-[(2-amino-2-phenylacetyl)amino]-2-fluoro-4-oxoazetidin-1-yl]-3-methylbut-2-enoic acid Chemical compound O=C1N(C(=C(C)C)C(O)=O)C(F)C1NC(=O)C(N)C1=CC=CC=C1 JUGAQLJUOITKIG-UHFFFAOYSA-N 0.000 description 1
- HEWUUUAOFGCFHK-UHFFFAOYSA-N 2-oxoazetidine-1-sulfinyl chloride Chemical class ClS(=O)N1CCC1=O HEWUUUAOFGCFHK-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- LFPOXPQRODFGRU-UHFFFAOYSA-N 3-[(2-chloroacetyl)amino]-1-[3-methyl-1-oxo-1-(2,2,2-trichloroethoxy)but-3-en-2-yl]-4-oxoazetidine-2-sulfinic acid Chemical compound ClC(Cl)(Cl)COC(=O)C(C(=C)C)N1C(S(O)=O)C(NC(=O)CCl)C1=O LFPOXPQRODFGRU-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- JCOLXNINLBTMIS-UHFFFAOYSA-N 4-chloroazetidin-2-one Chemical class ClC1CC(=O)N1 JCOLXNINLBTMIS-UHFFFAOYSA-N 0.000 description 1
- FIEQMOCSOXENFX-UHFFFAOYSA-N 4-oxoazetidine-2-sulfinic acid Chemical class OS(=O)C1CC(=O)N1 FIEQMOCSOXENFX-UHFFFAOYSA-N 0.000 description 1
- KDXFMMHNGFNJFA-UHFFFAOYSA-N 4-oxoazetidine-2-sulfinyl chloride Chemical class ClS(=O)C1CC(=O)N1 KDXFMMHNGFNJFA-UHFFFAOYSA-N 0.000 description 1
- HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WREBNDYJJMUWAO-LWYYNNOASA-N [(1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)[C@@H](CCC(C(C)C)=C3)C3=CC[C@H]21 WREBNDYJJMUWAO-LWYYNNOASA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- PSVQLHNSQKORAQ-UHFFFAOYSA-N benzhydryl 2-(3-acetamido-2-fluoro-4-oxoazetidin-1-yl)-3-methylbut-3-enoate Chemical compound O=C1C(NC(=O)C)C(F)N1C(C(C)=C)C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PSVQLHNSQKORAQ-UHFFFAOYSA-N 0.000 description 1
- ATLXQEQVSRWBCF-UHFFFAOYSA-N benzhydryl 2-(3-amino-2-fluoro-4-oxoazetidin-1-yl)-3-methylbut-2-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(=O)C(=C(C)C)N1C(F)C(N)C1=O ATLXQEQVSRWBCF-UHFFFAOYSA-N 0.000 description 1
- ALQKEXMTEJTDGR-UHFFFAOYSA-N benzhydryl 2-(3-amino-2-fluoro-4-oxoazetidin-1-yl)-3-methylbut-3-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(=O)C(C(=C)C)N1C(F)C(N)C1=O ALQKEXMTEJTDGR-UHFFFAOYSA-N 0.000 description 1
- PUXZAHLDKFSBLA-UHFFFAOYSA-N benzhydryl 2-(3-benzamido-2-fluoro-4-oxoazetidin-1-yl)-3-methylbut-3-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(=O)C(C(=C)C)N(C1=O)C(F)C1NC(=O)C1=CC=CC=C1 PUXZAHLDKFSBLA-UHFFFAOYSA-N 0.000 description 1
- CDBATTGFKJDRKE-UHFFFAOYSA-N benzhydryl 2-[2-fluoro-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-3-methylbut-2-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(=O)C(=C(C)C)N(C1=O)C(F)C1NC(=O)CC1=CC=CC=C1 CDBATTGFKJDRKE-UHFFFAOYSA-N 0.000 description 1
- 125000003460 beta-lactamyl group Chemical group 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000007017 scission Effects 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
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000626 sulfinic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BFICUDUFPORHKF-UHFFFAOYSA-N tert-butyl 2-(3-acetamido-2-fluoro-4-oxoazetidin-1-yl)-3-methylbut-3-enoate Chemical compound CC(=O)NC1C(F)N(C(C(C)=C)C(=O)OC(C)(C)C)C1=O BFICUDUFPORHKF-UHFFFAOYSA-N 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
-
- 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
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24198981A | 1981-03-09 | 1981-03-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE820516L IE820516L (en) | 1982-09-09 |
| IE52580B1 true IE52580B1 (en) | 1987-12-23 |
Family
ID=22913020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE516/82A IE52580B1 (en) | 1981-03-09 | 1982-03-08 | Azetidinone compounds and their preparation |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0060119B1 (Direct) |
| JP (1) | JPS57159760A (Direct) |
| KR (1) | KR850001879B1 (Direct) |
| CA (1) | CA1173837A (Direct) |
| DE (1) | DE3262931D1 (Direct) |
| DK (1) | DK99582A (Direct) |
| GB (1) | GB2094306B (Direct) |
| GR (1) | GR74762B (Direct) |
| HU (1) | HU188781B (Direct) |
| IE (1) | IE52580B1 (Direct) |
| IL (1) | IL65158A0 (Direct) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0117053A1 (en) * | 1983-02-10 | 1984-08-29 | Ajinomoto Co., Inc. | Azetidinone derivatives |
| US5631365A (en) | 1993-09-21 | 1997-05-20 | Schering Corporation | Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents |
-
1982
- 1982-03-03 IL IL65158A patent/IL65158A0/xx unknown
- 1982-03-04 CA CA000397601A patent/CA1173837A/en not_active Expired
- 1982-03-05 HU HU82692A patent/HU188781B/hu unknown
- 1982-03-05 GR GR67510A patent/GR74762B/el unknown
- 1982-03-08 IE IE516/82A patent/IE52580B1/en unknown
- 1982-03-08 KR KR8200990A patent/KR850001879B1/ko not_active Expired
- 1982-03-08 DE DE8282301165T patent/DE3262931D1/de not_active Expired
- 1982-03-08 GB GB8206710A patent/GB2094306B/en not_active Expired
- 1982-03-08 EP EP82301165A patent/EP0060119B1/en not_active Expired
- 1982-03-08 DK DK99582A patent/DK99582A/da not_active Application Discontinuation
- 1982-03-09 JP JP57037900A patent/JPS57159760A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA1173837A (en) | 1984-09-04 |
| KR830009087A (ko) | 1983-12-17 |
| KR850001879B1 (ko) | 1985-12-28 |
| EP0060119A1 (en) | 1982-09-15 |
| GR74762B (Direct) | 1984-07-12 |
| GB2094306B (en) | 1985-03-13 |
| DE3262931D1 (en) | 1985-05-15 |
| HU188781B (en) | 1986-05-28 |
| EP0060119B1 (en) | 1985-04-10 |
| DK99582A (da) | 1982-09-10 |
| JPS57159760A (en) | 1982-10-01 |
| GB2094306A (en) | 1982-09-15 |
| IE820516L (en) | 1982-09-09 |
| IL65158A0 (en) | 1982-05-31 |
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