CH633290A5 - Process for preparing derivatives of 7-oxo-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid - Google Patents

Process for preparing derivatives of 7-oxo-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid Download PDF

Info

Publication number: CH633290A5
Authority: CH; Switzerland
Prior art keywords: group; oxo; cis; general formula; compound
Prior art date: 1975-09-03

Application number

CH1117176A

Other languages

German (de)

English (en)

Inventor

John Gerald Gleason

Kenneth George Holden

William Francis Huffman

Original Assignee

Smithkline Corp

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.)

1975-09-03

Filing date

1976-09-02

Publication date

1982-11-30

1975-09-03 Priority claimed from US05/610,517 external-priority patent/US4000154A/en

1976-09-02 Application filed by Smithkline Corp filed Critical Smithkline Corp

1982-11-30 Publication of CH633290A5 publication Critical patent/CH633290A5/de

Links

KNQWNKVLMILMKH-UHFFFAOYSA-N 7-oxo-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid Chemical class OC(=O)C1NCC2CC(=O)N12 KNQWNKVLMILMKH-UHFFFAOYSA-N 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title description 2
-1 phenylacetyl group Chemical group 0.000 claims description 63
150000001875 compounds Chemical class 0.000 claims description 47
125000006239 protecting group Chemical group 0.000 claims description 18
238000000034 method Methods 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 9
150000002148 esters Chemical group 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
239000012346 acetyl chloride Substances 0.000 claims description 4
150000001266 acyl halides Chemical class 0.000 claims description 4
150000001555 benzenes Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
BNENAZVHANNQGG-FXAWDEMLSA-N benzyl 2-[[(2s,3r)-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-2-yl]methylimino]acetate Chemical compound N([C@H]1C(N[C@H]1CN=CC(=O)OCC=1C=CC=CC=1)=O)C(=O)COC1=CC=CC=C1 BNENAZVHANNQGG-FXAWDEMLSA-N 0.000 claims description 3
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 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 claims description 3
150000002960 penicillins Chemical class 0.000 claims description 3
229930182555 Penicillin Natural products 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
125000006502 nitrobenzyl group Chemical group 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
125000006207 phenyl benzoyl methyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(=O)C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 2
XCVIKOAUQDAMAG-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.0]heptan-7-one Chemical compound N1CCN2C(=O)CC21 XCVIKOAUQDAMAG-UHFFFAOYSA-N 0.000 claims 1
PLJMVAOHNZXLOF-UHFFFAOYSA-N 3-thia-1-azabicyclo[3.2.0]heptan-7-one Chemical class C1SCN2C(=O)CC21 PLJMVAOHNZXLOF-UHFFFAOYSA-N 0.000 claims 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
UBIRCWMYTXDXJX-UHFFFAOYSA-N 4-oxa-1-azabicyclo[3.2.0]heptan-7-one Chemical class O1CCN2C(=O)CC21 UBIRCWMYTXDXJX-UHFFFAOYSA-N 0.000 claims 1
WSHJJCPTKWSMRR-UHFFFAOYSA-N 4-thia-1-azabicyclo[3.2.0]heptan-7-one Chemical group S1CCN2C(=O)CC21 WSHJJCPTKWSMRR-UHFFFAOYSA-N 0.000 claims 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical class CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 claims 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 1
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 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 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 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
239000000243 solution Substances 0.000 description 41
239000000203 mixture Substances 0.000 description 36
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 23
238000002474 experimental method Methods 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
239000000706 filtrate Substances 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
239000003480 eluent Substances 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
238000004809 thin layer chromatography Methods 0.000 description 8
239000000047 product Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
150000004702 methyl esters Chemical class 0.000 description 6
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 6
229910000033 sodium borohydride Inorganic materials 0.000 description 6
239000012279 sodium borohydride Substances 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 5
239000002024 ethyl acetate extract Substances 0.000 description 5
239000000155 melt Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
239000005909 Kieselgur Substances 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
230000001681 protective effect Effects 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
238000000862 absorption spectrum Methods 0.000 description 3
125000003368 amide group Chemical group 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 3
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 3
239000012267 brine Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000004519 grease Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
150000002466 imines Chemical class 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000003952 β-lactams Chemical group 0.000 description 3
QOWBXWFYRXSBAS-UHFFFAOYSA-N (2,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C(OC)=C1 QOWBXWFYRXSBAS-UHFFFAOYSA-N 0.000 description 2
FUUJJKKLRGGIKY-UHFFFAOYSA-N 2-(2-oxo-4,5-diphenyl-1,3-oxazol-3-yl)acetyl chloride Chemical compound O1C(=O)N(CC(=O)Cl)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 FUUJJKKLRGGIKY-UHFFFAOYSA-N 0.000 description 2
PPXUUPXQWDQNGO-UHFFFAOYSA-N 2-azidoacetic acid Chemical compound OC(=O)CN=[N+]=[N-] PPXUUPXQWDQNGO-UHFFFAOYSA-N 0.000 description 2
XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
FTWWNKCHSPDIQW-UHFFFAOYSA-N azetidin-2-ylmethanol Chemical compound OCC1CCN1 FTWWNKCHSPDIQW-UHFFFAOYSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
DOMUIIVWHOMQCB-UHFFFAOYSA-N benzyl 2-methylheptanoate Chemical compound CCCCCC(C)C(=O)OCC1=CC=CC=C1 DOMUIIVWHOMQCB-UHFFFAOYSA-N 0.000 description 2
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
BTNMPGBKDVTSJY-UHFFFAOYSA-M keto-phenylpyruvate Chemical compound [O-]C(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-M 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
HWIPKUZJQXCDEP-UHFFFAOYSA-N methyl 2-[(2,4-dimethoxyphenyl)methylimino]acetate Chemical compound COC(=O)C=NCC1=CC=C(OC)C=C1OC HWIPKUZJQXCDEP-UHFFFAOYSA-N 0.000 description 2
LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
AVWWZSWBJXZQQU-UHFFFAOYSA-N (4-oxoazetidin-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1NC(=O)C1 AVWWZSWBJXZQQU-UHFFFAOYSA-N 0.000 description 1
KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 1
ANUZNUZVUXSPIF-UHFFFAOYSA-N 2-(2-oxo-4,5-diphenyl-1,3-oxazol-3-yl)acetic acid Chemical compound O1C(=O)N(CC(=O)O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ANUZNUZVUXSPIF-UHFFFAOYSA-N 0.000 description 1
MGKPFALCNDRSQD-UHFFFAOYSA-N 2-(4-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C=C1 MGKPFALCNDRSQD-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
HNORVZDAANCHAY-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=C(C(F)(F)F)C=C1 HNORVZDAANCHAY-UHFFFAOYSA-N 0.000 description 1
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
FVMDYYGIDFPZAX-UHFFFAOYSA-N 3-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=CC(O)=C1 FVMDYYGIDFPZAX-UHFFFAOYSA-N 0.000 description 1
FQXQBFUUVCDIRK-UHFFFAOYSA-N 3-trifluoromethylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C(F)(F)F)=C1 FQXQBFUUVCDIRK-UHFFFAOYSA-N 0.000 description 1
ZQVKTHRQIXSMGY-UHFFFAOYSA-N 4-Ethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1 ZQVKTHRQIXSMGY-UHFFFAOYSA-N 0.000 description 1
MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 1
TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 1
LAUFPZPAKULAGB-UHFFFAOYSA-N 4-butoxybenzoic acid Chemical compound CCCCOC1=CC=C(C(O)=O)C=C1 LAUFPZPAKULAGB-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
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 1
238000012404 In vitro experiment Methods 0.000 description 1
DTGKSKDOIYIVQL-MRTMQBJTSA-N Isoborneol Natural products C1C[C@@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-MRTMQBJTSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
YQKMJMRJXRHOKZ-PKOBYXMFSA-N benzyl 2-[[(2s,3r)-4-oxo-3-(phenylmethoxycarbonylamino)azetidin-2-yl]methylimino]acetate Chemical compound C([C@H]1[C@H](C(N1)=O)NC(=O)OCC=1C=CC=CC=1)N=CC(=O)OCC1=CC=CC=C1 YQKMJMRJXRHOKZ-PKOBYXMFSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
125000003460 beta-lactamyl group Chemical group 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000002826 coolant Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005179 haloacetyl group Chemical group 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
WAKVYXZJTFOVKC-UHFFFAOYSA-N methyl 4-oxoazetidine-2-carboxylate Chemical compound COC(=O)C1CC(=O)N1 WAKVYXZJTFOVKC-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
FJADRFHKHXEPCL-UHFFFAOYSA-N n-(2-oxoazetidin-3-yl)-2-phenoxyacetamide Chemical compound C1NC(=O)C1NC(=O)COC1=CC=CC=C1 FJADRFHKHXEPCL-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/36—One oxygen atom
- C07D263/38—One oxygen atom attached in position 2

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CH1117176A 1975-09-03 1976-09-02 Process for preparing derivatives of 7-oxo-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid CH633290A5 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/610,517 US4000154A (en)	1975-09-03	1975-09-03	3-Substituted-6β-(amino- and acylamino)-7-oxo-1,3-diazabicyclo[3.2.0]-h
US68780576A	1976-05-19	1976-05-19

Publications (1)

Publication Number	Publication Date
CH633290A5 true CH633290A5 (en)	1982-11-30

Family

ID=27086273

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1117176A CH633290A5 (en)	1975-09-03	1976-09-02	Process for preparing derivatives of 7-oxo-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid

Country Status (7)

Country	Link
JP (1)	JPS6055507B2 (fr)
CH (1)	CH633290A5 (fr)
DE (1)	DE2639397A1 (fr)
FR (2)	FR2361885A1 (fr)
GB (2)	GB1566262A (fr)
IE (1)	IE44230B1 (fr)
NL (1)	NL7609838A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3108089C2 (de) *	1981-03-04	1987-01-15	Focke & Co, 2810 Verden	Vorrichtung zum Auftragen von Leim auf Lappen von Verpackungen
FR2515182B1 (fr) *	1981-10-23	1986-05-09	Roussel Uclaf	Nouveaux produits derives de l'acide 3-amino 2-oxo azetidine 1-sulfamique, leur procede de preparation, leur application comme medicaments et les produits intermediaires necessaires a leur preparation
GB2151628B (en) *	1981-10-23	1986-05-21	Roussel Uclaf	Azetidine intermediates
JPS6316908U (fr) *	1986-07-19	1988-02-04

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2219601A1 (de) *	1971-04-27	1972-11-16	Astra Läkemedel AB, Södertälje (Schweden)	beta-Lactame und Verfahren zu deren Herstellung
NL7402539A (fr) *	1973-03-13	1974-09-17
DE2356862A1 (de) *	1973-11-14	1975-05-15	Univ Kingston	Sauerstoffanaloga von 6-aminopenicillansaeurederivaten und verfahren zu ihrer herstellung

1976
- 1976-08-30 FR FR7626099A patent/FR2361885A1/fr active Granted
- 1976-09-01 JP JP51105379A patent/JPS6055507B2/ja not_active Expired
- 1976-09-01 DE DE19762639397 patent/DE2639397A1/de not_active Withdrawn
- 1976-09-01 IE IE1953/76A patent/IE44230B1/en unknown
- 1976-09-02 CH CH1117176A patent/CH633290A5/de not_active IP Right Cessation
- 1976-09-03 NL NL7609838A patent/NL7609838A/xx not_active Application Discontinuation
- 1976-09-03 GB GB17327/79A patent/GB1566262A/en not_active Expired
- 1976-09-03 GB GB35505/76A patent/GB1566261A/en not_active Expired
1977
- 1977-01-21 FR FR7701808A patent/FR2344534A1/fr active Granted

Also Published As

Publication number	Publication date
FR2361885B1 (fr)	1980-03-14
DE2639397A1 (de)	1977-03-10
JPS6055507B2 (ja)	1985-12-05
GB1566261A (en)	1980-04-30
FR2344534A1 (fr)	1977-10-14
IE44230L (en)	1977-03-03
GB1566262A (en)	1980-04-30
IE44230B1 (en)	1981-09-23
NL7609838A (nl)	1977-03-07
FR2361885A1 (fr)	1978-03-17
FR2344534B1 (fr)	1980-07-04
JPS5239695A (en)	1977-03-28

Legal Events

Date	Code	Title	Description
1988-05-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE3018590A1 (de)	1980-11-20	Bisester von methandiol mit penicillinen und penicillansaeure-1,1-dioxid
DD154542A5 (de)	1982-03-31	Verfahren zur herstellung von 6 beta-hydroxyalkylpenicillansaeuren
DE3239157C2 (de)	1994-04-28	3-Oximinoacylamino-4-fluormethyl-1-sulfoazetidinone, ihre Herstellung, Zwischenprodukte und pharmazeutische Zusammensetzungen
EP0005889A1 (fr)	1979-12-12	Procédé de préparation de dérivés de bêta-lactame, les nouveaux dérivés ainsi obtenus et compositions pharmaceutiques les contenant
US4237051A (en)	1980-12-02	Stereospecific production of 6- or 7-carbon-substituted-β-lactams
CH644866A5 (de)	1984-08-31	Cephalosporin-analoge und verfahren zu ihrer herstellung.
JPH0557980B2 (fr)	1993-08-25
DE2740280A1 (de)	1978-03-09	7-acylamino-8-oxo-3-oxa-1-azabicyclo eckige klammer auf 4.2.0 eckige klammer zu octan-2-carbonsaeure-derivate
DE2619458A1 (de)	1976-11-18	7 beta -acylamino-6 alpha h-8-oxo-4thia-1-azabicyclo eckige klammer auf 4.2.0 eckige klammer zu oct-2-en-2- carbonsaeure-derivate, verfahren zu ihrer herstellung, arzneimittel und zwischenprodukte
US4200572A (en)	1980-04-29	Substituted azetidinones
CH628900A5 (fr)	1982-03-31	Procede de preparation de thio-oximes derivees de cephalosporines et de penicillines.
EP0300278A2 (fr)	1989-01-25	Procédé de préparation de pyrroles 2-substituées
DE2718714A1 (de)	1977-11-17	2-oxoazetidin-derivate und verfahren zu ihrer herstellung
EP0000645B1 (fr)	1981-01-28	Isopénicillines, procédés pour leur préparation et compositions qui les contiennent
CH630333A5 (de)	1982-06-15	Verfahren zur spaltung von benzylestern von carbonsaeuren.
CH644608A5 (de)	1984-08-15	Verfahren zur herstellung von penicillansaeure-1,1-dioxid und dessen estern sowie zwischenverbindungen zur durchfuehrung des verfahrens.
FR2496666A1 (fr)	1982-06-25	Nouveaux derives de cephalosporine et composition pharmaceutique les contenant
CH648850A5 (de)	1985-04-15	Penicillansaeure-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel.
US4000154A (en)	1976-12-28	3-Substituted-6β-(amino- and acylamino)-7-oxo-1,3-diazabicyclo[3.2.0]-h
US4103086A (en)	1978-07-25	8-Oxo-4-thia-1-azabicyclo (4.2.0)-oct-2-ene derivatives
DE3779675T2 (de)	1992-12-10	6-(disubstituiertes amino)carbapenam-verbindungen.
DE2612926A1 (de)	1977-10-06	Neue acyl-derivate der 6-(alpha- amino-phenylacetamido)-penicillansaeure
CH619468A5 (fr)	1980-09-30
DE2429166A1 (de)	1975-01-09	Verfahren zur selektiven spaltung der amidsaeurefunktion eines 7-(amidsaeure)cephalosporins
DE2639397A1 (de)	1977-03-10	7-oxo-1,3-diazabicyclo eckige klammer auf 3.2.o eckige klammer zu heptan-2-carbonsaeure-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte