CA1059992A - Penam derivatives and preparation thereof - Google Patents

Penam derivatives and preparation thereof

Info

Publication number: CA1059992A
Authority: CA; Canada
Prior art keywords: carbon atoms; substituted; group; penam; phenyl
Prior art date: 1973-10-17
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

Application number

CA211,057A

Other languages

English (en)

French (fr)

Other versions

CA211057S (en

Inventor

Wayne E. Barth

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.)

Pfizer Corp SRL

Original Assignee

Pfizer Corp SRL

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.)

1973-10-17

Filing date

1974-10-09

Publication date

1979-08-07

1974-10-09 Application filed by Pfizer Corp SRL filed Critical Pfizer Corp SRL

1979-08-07 Application granted granted Critical

1979-08-07 Publication of CA1059992A publication Critical patent/CA1059992A/en

Status Expired legal-status Critical Current

Links

150000002959 penams Chemical class 0.000 title claims description 30
238000002360 preparation method Methods 0.000 title abstract description 24
-1 5- tetrazolyl moiety Chemical group 0.000 claims abstract description 305
WSHJJCPTKWSMRR-RXMQYKEDSA-N penam group Chemical group S1CCN2[C@H]1CC2=O WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 claims abstract description 291
238000000034 method Methods 0.000 claims abstract description 270
238000006243 chemical reaction Methods 0.000 claims abstract description 130
150000003839 salts Chemical class 0.000 claims abstract description 65
230000008569 process Effects 0.000 claims abstract description 50
125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 47
125000006239 protecting group Chemical group 0.000 claims abstract description 39
238000005917 acylation reaction Methods 0.000 claims abstract description 35
230000010933 acylation Effects 0.000 claims abstract description 33
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 19
150000001875 compounds Chemical class 0.000 claims description 271
125000004432 carbon atom Chemical group C* 0.000 claims description 207
229910052739 hydrogen Inorganic materials 0.000 claims description 183
239000001257 hydrogen Substances 0.000 claims description 182
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 139
125000000217 alkyl group Chemical group 0.000 claims description 90
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 88
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 76
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 70
239000002253 acid Substances 0.000 claims description 65
125000003545 alkoxy group Chemical group 0.000 claims description 37
239000003795 chemical substances by application Substances 0.000 claims description 36
125000001544 thienyl group Chemical group 0.000 claims description 36
239000007858 starting material Substances 0.000 claims description 34
125000002252 acyl group Chemical group 0.000 claims description 32
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
125000005633 phthalidyl group Chemical group 0.000 claims description 25
150000001412 amines Chemical class 0.000 claims description 24
125000002541 furyl group Chemical group 0.000 claims description 24
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
125000001309 chloro group Chemical group Cl* 0.000 claims description 23
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 22
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 21
150000008064 anhydrides Chemical class 0.000 claims description 20
125000004076 pyridyl group Chemical group 0.000 claims description 20
125000003277 amino group Chemical group 0.000 claims description 19
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
125000005042 acyloxymethyl group Chemical group 0.000 claims description 18
125000001153 fluoro group Chemical group F* 0.000 claims description 18
125000004423 acyloxy group Chemical group 0.000 claims description 17
150000002148 esters Chemical class 0.000 claims description 17
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 16
125000001786 isothiazolyl group Chemical group 0.000 claims description 16
125000002883 imidazolyl group Chemical group 0.000 claims description 15
239000012948 isocyanate Substances 0.000 claims description 15
125000003226 pyrazolyl group Chemical group 0.000 claims description 15
125000004665 trialkylsilyl group Chemical group 0.000 claims description 15
NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims description 14
125000000335 thiazolyl group Chemical group 0.000 claims description 14
125000001425 triazolyl group Chemical group 0.000 claims description 14
KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 13
125000001246 bromo group Chemical group Br* 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
150000003512 tertiary amines Chemical class 0.000 claims description 13
150000002513 isocyanates Chemical class 0.000 claims description 12
125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 11
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
150000004820 halides Chemical class 0.000 claims description 10
IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
ZMMRLWFGWQVVJD-UHFFFAOYSA-O (n,n-dimethylcarbamimidoyl)-dimethylazanium;azide Chemical compound [N-]=[N+]=[N-].CN(C)C(N)=[N+](C)C ZMMRLWFGWQVVJD-UHFFFAOYSA-O 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
150000001540 azides Chemical class 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
125000005846 1-(alkanoyloxy)ethyl group Chemical group 0.000 claims description 7
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
125000000168 pyrrolyl group Chemical group 0.000 claims description 6
229910052717 sulfur Chemical group 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000004442 acylamino group Chemical group 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
230000008878 coupling Effects 0.000 claims description 5
238000010168 coupling process Methods 0.000 claims description 5
238000005859 coupling reaction Methods 0.000 claims description 5
239000002243 precursor Substances 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
239000007822 coupling agent Substances 0.000 claims description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000002188 cycloheptatrienyl group Chemical group C1(=CC=CC=CC1)* 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 claims description 4
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 claims description 4
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 3
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 2
150000002540 isothiocyanates Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 19
150000007524 organic acids Chemical class 0.000 claims 1
AWRSDQGCXNOXOC-NUWLTMBBSA-N (5r)-6-amino-3,3-dimethyl-2-(2h-tetrazol-5-yl)-4-thia-1-azabicyclo[3.2.0]heptan-7-one Chemical compound NC([C@H]1SC2(C)C)C(=O)N1C2C=1N=NNN=1 AWRSDQGCXNOXOC-NUWLTMBBSA-N 0.000 abstract description 30
239000003242 anti bacterial agent Substances 0.000 abstract description 12
239000000543 intermediate Substances 0.000 abstract description 12
238000001228 spectrum Methods 0.000 abstract description 10
230000009466 transformation Effects 0.000 abstract description 7
239000000243 solution Substances 0.000 description 245
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 218
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 211
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 203
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 124
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 118
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 113
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 110
239000000047 product Substances 0.000 description 106
229960001701 chloroform Drugs 0.000 description 105
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 99
238000003756 stirring Methods 0.000 description 90
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 76
229940093499 ethyl acetate Drugs 0.000 description 73
235000019439 ethyl acetate Nutrition 0.000 description 72
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 70
239000002904 solvent Substances 0.000 description 69
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 67
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 67
239000000203 mixture Substances 0.000 description 66
229940086542 triethylamine Drugs 0.000 description 65
238000010521 absorption reaction Methods 0.000 description 61
230000009102 absorption Effects 0.000 description 60
238000005481 NMR spectroscopy Methods 0.000 description 56
150000001408 amides Chemical class 0.000 description 56
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 52
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
238000001704 evaporation Methods 0.000 description 49
230000008020 evaporation Effects 0.000 description 48
239000007787 solid Substances 0.000 description 45
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
239000011541 reaction mixture Substances 0.000 description 42
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 40
239000008346 aqueous phase Substances 0.000 description 38
238000007792 addition Methods 0.000 description 37
239000002244 precipitate Substances 0.000 description 36
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 35
230000000875 corresponding effect Effects 0.000 description 34
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 33
235000011121 sodium hydroxide Nutrition 0.000 description 33
229940083608 sodium hydroxide Drugs 0.000 description 33
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 32
229940073584 methylene chloride Drugs 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
239000000126 substance Substances 0.000 description 29
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
239000012043 crude product Substances 0.000 description 22
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 21
238000002329 infrared spectrum Methods 0.000 description 21
101150041968 CDC13 gene Proteins 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
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 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
239000010410 layer Substances 0.000 description 18
239000011734 sodium Substances 0.000 description 18
229910052708 sodium Inorganic materials 0.000 description 18
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 18
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 17
230000015572 biosynthetic process Effects 0.000 description 17
239000000284 extract Substances 0.000 description 17
238000001914 filtration Methods 0.000 description 17
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
239000000725 suspension Substances 0.000 description 17
238000001816 cooling Methods 0.000 description 16
INAVQIOTUQGEAF-LWOQYNTDSA-N C([C@H]1SC2(C)C)C(=O)N1C2C1=NN=NN1 Chemical compound C([C@H]1SC2(C)C)C(=O)N1C2C1=NN=NN1 INAVQIOTUQGEAF-LWOQYNTDSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
239000000706 filtrate Substances 0.000 description 14
235000011167 hydrochloric acid Nutrition 0.000 description 14
229960000443 hydrochloric acid Drugs 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 14
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 14
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
230000000844 anti-bacterial effect Effects 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 11
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 11
239000012267 brine Substances 0.000 description 11
230000006870 function Effects 0.000 description 11
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 11
239000002002 slurry Substances 0.000 description 11
159000000000 sodium salts Chemical class 0.000 description 11
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
125000003460 beta-lactamyl group Chemical group 0.000 description 10
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
QTHZORHGLCOAQI-YEJVQYHQSA-N (2R)-2-amino-N-[(5R)-3,3-dimethyl-7-oxo-2-(2H-tetrazol-5-yl)-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylacetamide Chemical compound N[C@@H](C(=O)NC1[C@@H]2N(C(C(S2)(C)C)C2=NN=NN2)C1=O)C1=CC=CC=C1 QTHZORHGLCOAQI-YEJVQYHQSA-N 0.000 description 9
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 9
239000000039 congener Substances 0.000 description 9
229960005419 nitrogen Drugs 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
125000004429 atom Chemical group 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
230000000694 effects Effects 0.000 description 8
238000005755 formation reaction Methods 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
VHOYFVFTYVTOBQ-SDMSXHDGSA-N (5r)-3-(2h-tetrazol-5-yl)-4-thia-1-azabicyclo[3.2.0]heptan-7-one Chemical compound S([C@@H]1CC(N1C1)=O)C1C=1N=NNN=1 VHOYFVFTYVTOBQ-SDMSXHDGSA-N 0.000 description 7
XLCUJQQFWDZWIT-UFFDXJJYSA-N 2-amino-n-[(2s,5r,6r)-3,3-dimethyl-7-oxo-2-(2h-tetrazol-5-yl)-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-(4-hydroxyphenyl)acetamide Chemical class N([C@H]1[C@H]2SC([C@@H](N2C1=O)C1=NNN=N1)(C)C)C(=O)C(N)C1=CC=C(O)C=C1 XLCUJQQFWDZWIT-UFFDXJJYSA-N 0.000 description 7
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 7
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BKIAIXBIMIOJFW-TXRRYJPOSA-N phenyl 3-[[(5r)-3,3-dimethyl-7-oxo-2-(2h-tetrazol-5-yl)-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]amino]-3-oxo-2-phenylpropanoate Chemical compound C1([C@H]2SC(C(N2C1=O)C1=NNN=N1)(C)C)NC(=O)C(C=1C=CC=CC=1)C(=O)OC1=CC=CC=C1 BKIAIXBIMIOJFW-TXRRYJPOSA-N 0.000 description 1
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239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
ZOSLBJGPFLIVKI-UHFFFAOYSA-M sodium;2-[(4-methoxy-4-oxobut-2-en-2-yl)amino]acetate Chemical class [Na+].COC(=O)C=C(C)NCC([O-])=O ZOSLBJGPFLIVKI-UHFFFAOYSA-M 0.000 description 1
FNEVXHRWAIYODR-UHFFFAOYSA-M sodium;2-[4-[[(1-methoxy-1-oxobut-3-en-2-yl)amino]methyl]phenyl]acetate Chemical compound [Na+].COC(=O)C(C=C)NCC1=CC=C(CC([O-])=O)C=C1 FNEVXHRWAIYODR-UHFFFAOYSA-M 0.000 description 1
HWEXKRHYVOGVDA-UHFFFAOYSA-M sodium;3-trimethylsilylpropane-1-sulfonate Chemical compound [Na+].C[Si](C)(C)CCCS([O-])(=O)=O HWEXKRHYVOGVDA-UHFFFAOYSA-M 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000008054 sulfonate salts Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
230000009469 supplementation Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
VKDYDXILKHBYHT-UHFFFAOYSA-O tributylazanium;azide Chemical compound [N-]=[N+]=[N-].CCCC[NH+](CCCC)CCCC VKDYDXILKHBYHT-UHFFFAOYSA-O 0.000 description 1
DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical compound CC[O+](CC)CC DWCSXQCXXITVKE-UHFFFAOYSA-N 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
238000005292 vacuum distillation Methods 0.000 description 1
ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical class C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

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

CA211,057A 1973-10-17 1974-10-09 Penam derivatives and preparation thereof Expired CA1059992A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US40709773A	1973-10-17	1973-10-17
US45043574A	1974-03-12	1974-03-12

Publications (1)

Publication Number	Publication Date
CA1059992A true CA1059992A (en)	1979-08-07

Family

ID=27019757

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA211,057A Expired CA1059992A (en)	1973-10-17	1974-10-09	Penam derivatives and preparation thereof

Country Status (26)

Country	Link
JP (1)	JPS5740839B2 (cs)
AR (2)	AR214039A1 (cs)
AU (1)	AU475973B2 (cs)
BG (2)	BG27752A3 (cs)
CA (1)	CA1059992A (cs)
CH (1)	CH605979A5 (cs)
CS (1)	CS193505B2 (cs)
DD (1)	DD114082A5 (cs)
DE (1)	DE2462675B1 (cs)
DK (1)	DK150515C (cs)
ES (1)	ES431064A1 (cs)
FI (2)	FI59411C (cs)
FR (1)	FR2248044B1 (cs)
GB (1)	GB1481600A (cs)
HU (1)	HU174960B (cs)
IE (1)	IE40532B1 (cs)
IL (1)	IL45833A (cs)
IN (1)	IN143272B (cs)
LU (1)	LU71116A1 (cs)
NL (1)	NL178508C (cs)
NO (2)	NO147915C (cs)
OA (1)	OA04798A (cs)
RO (1)	RO70536A (cs)
SE (2)	SE425788B (cs)
YU (1)	YU36521B (cs)
ZM (1)	ZM15374A1 (cs)

1974
- 1974-09-27 SE SE7412234A patent/SE425788B/xx unknown
- 1974-10-08 GB GB43620/74A patent/GB1481600A/en not_active Expired
- 1974-10-09 CA CA211,057A patent/CA1059992A/en not_active Expired
- 1974-10-11 IL IL45833A patent/IL45833A/xx unknown
- 1974-10-14 IE IE2112/74A patent/IE40532B1/en unknown
- 1974-10-15 ZM ZM153/74A patent/ZM15374A1/xx unknown
- 1974-10-15 YU YU02759/74A patent/YU36521B/xx unknown
- 1974-10-15 RO RO7490550A patent/RO70536A/ro unknown
- 1974-10-16 FI FI3024/74A patent/FI59411C/fi active
- 1974-10-16 NL NLAANVRAGE7413589,A patent/NL178508C/xx not_active IP Right Cessation
- 1974-10-16 CH CH383577A patent/CH605979A5/xx not_active IP Right Cessation
- 1974-10-16 DK DK541974A patent/DK150515C/da not_active IP Right Cessation
- 1974-10-16 DD DD181738A patent/DD114082A5/xx unknown
- 1974-10-16 CS CS747099A patent/CS193505B2/cs unknown
- 1974-10-16 FI FI3025/74A patent/FI302574A7/fi unknown
- 1974-10-16 NO NO743738A patent/NO147915C/no unknown
- 1974-10-16 ES ES431064A patent/ES431064A1/es not_active Expired
- 1974-10-16 HU HU74PI434A patent/HU174960B/hu unknown
- 1974-10-16 LU LU71116A patent/LU71116A1/xx unknown
- 1974-10-17 JP JP49118742A patent/JPS5740839B2/ja not_active Expired
- 1974-10-17 AU AU74424/74A patent/AU475973B2/en not_active Expired
- 1974-10-17 DE DE2462675A patent/DE2462675B1/de active Granted
- 1974-10-17 BG BG035959A patent/BG27752A3/xx unknown
- 1974-10-17 BG BG027976A patent/BG27090A3/xx unknown
- 1974-10-17 FR FR7435014A patent/FR2248044B1/fr not_active Expired
- 1974-10-18 OA OA55327A patent/OA04798A/xx unknown
- 1974-10-28 IN IN2348/CAL/74A patent/IN143272B/en unknown
1975
- 1975-05-27 AR AR258967A patent/AR214039A1/es active
1977
- 1977-04-02 AR AR267281A patent/AR219704A1/es active
- 1977-07-26 SE SE7708594A patent/SE7708594L/xx not_active Application Discontinuation
1978
- 1978-11-14 NO NO783827A patent/NO148526C/no unknown

Also Published As

Publication number	Publication date
DK150515B (da)	1987-03-16
NO147915B (no)	1983-03-28
DE2462675C2 (cs)	1980-01-03
FI302574A7 (cs)	1975-04-18
FR2248044A1 (cs)	1975-05-16
IL45833A (en)	1978-07-31
IL45833A0 (en)	1974-12-31
NO743738L (cs)	1975-05-12
AU7442474A (en)	1976-04-29
NO147915C (no)	1983-07-06
CS193505B2 (en)	1979-10-31
NL7413589A (nl)	1975-04-21
YU275974A (en)	1982-02-25
FI59411B (fi)	1981-04-30
NO148526C (no)	1983-10-26
DK150515C (da)	1987-09-28
RO70536A (ro)	1981-05-30
GB1481600A (en)	1977-08-03
BG27752A3 (bg)	1979-12-12
YU36521B (en)	1984-02-29
AR214039A1 (es)	1979-04-30
BG27090A3 (bg)	1979-08-15
SE7708594L (sv)	1977-07-26
JPS5740839B2 (cs)	1982-08-30
NL178508B (nl)	1985-11-01
DE2462675B1 (de)	1979-05-17
ZM15374A1 (en)	1976-06-21
FI59411C (fi)	1981-08-10
ES431064A1 (es)	1977-02-16
FR2248044B1 (cs)	1977-10-28
NO783827L (no)	1975-04-18
IN143272B (cs)	1977-10-29
DK541974A (cs)	1975-06-16
CH605979A5 (cs)	1978-10-13
NL178508C (nl)	1986-04-01
HU174960B (hu)	1980-04-28
AU475973B2 (en)	1976-09-09
DD114082A5 (cs)	1975-07-12
IE40532L (en)	1975-04-17
NO148526B (no)	1983-07-18
FI302474A7 (cs)	1975-04-18
SE7412234L (cs)	1975-04-18
LU71116A1 (cs)	1975-06-24
OA04798A (fr)	1980-08-31
JPS5064295A (cs)	1975-05-31
SE425788B (sv)	1982-11-08
AR219704A1 (es)	1980-09-15
IE40532B1 (en)	1979-06-20

Publication	Publication Date	Title
SE446186B (sv)	1986-08-18	Beta-laktamforeningar samt farmaceutiska kompositioner derav
NL8105470A (nl)	1982-07-01	1-sulfo 2-oxoazetidinederivaten, alsmede bereiding en toepassing daarvan.
USRE31926E (en)	1985-06-25	Penicillins and salts thereof
US4374138A (en)	1983-02-15	Antibacterial amide compounds, compositions, and methods of use
US4053609A (en)	1977-10-11	Penicillins and processes for preparing the same
CA1059992A (en)	1979-08-07	Penam derivatives and preparation thereof
EP0000392B1 (de)	1982-04-28	Cephalosporin und Penicillin-derivate, Verfahren zu deren Herstellung, und deren pharmazeutische Präparate
US4115385A (en)	1978-09-19	Antibacterial 3-(5-tetrazolyl) penam compounds
US3933797A (en)	1976-01-20	6-[α-(ω-QUANIDINOALKANOYLAMIDO)ACYLAMIDO]PENICILLANIC ACIDS
IE871651L (en)	1987-12-23	Azetidine derivatives
US4179511A (en)	1979-12-18	Antibacterial 3-(5-tetrazolyl) penam compounds
US3406185A (en)	1968-10-15	Antibiotics
HU181961B (en)	1983-11-28	Process for producing new oxime derivatives of 3-thiadiazolythio-methyl-7-aminothiazolylacetamido-ceph-3-eme-4-carboxylic acids
CA1063108A (en)	1979-09-25	Azetidinone derivatives and process for preparation thereof
US3946003A (en)	1976-03-23	Hydroxy substituted phenylglycylamido-3-heterocyclic thiomethyl cephalosporins
CA1056817A (en)	1979-06-19	Penicillins
US3668198A (en)	1972-06-06	{60 -ureido-2,4,6-cycloheptatrienylmethylpenicillins
Hardy et al.	1984	The chemistry of some 2-aminothiazol-4-ylacetic acid derivatives and the synthesis of derived penicillins
CA1050010A (en)	1979-03-06	Process for preparing-3-methyl-4-(5-tetrazolyl)-a3-cephem compounds
JP3523664B2 (ja)	2004-04-26	新規なペナム誘導体またはその塩
CA1060887A (en)	1979-08-21	Process for the production of 6-acylamino-2,2-dimethyl-3-(5-tetrazolyl) penams and intermediates therefor
CA1104562A (en)	1981-07-07	Cephalosporins, processes for their preparation and their use as medicaments
JPS60105676A (ja)	1985-06-11	フルオロアルキル化カルバペネム誘導体およびその製法
US4044047A (en)	1977-08-23	Intermediates for preparing substituted phenylglycylcephalosporins
US3714150A (en)	1973-01-30	6-(2,5-dioxo-4-phenyl-n-substituted-4-imidazolinecarboxamido)penicillanic acids