CA1129871A - Derives de l'azetidine - Google Patents

Derives de l'azetidine

Info

Publication number: CA1129871A
Authority: CA; Canada
Prior art keywords: hal; beta; alpha; oxoazetidin; cob
Prior art date: 1976-07-28
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

CA393,848A

Other languages

English (en)

Inventor

Mitsuru Yoshioka

Yoshio Hamashima

Wataru Nagata

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.)

Shionogi and Co Ltd

Original Assignee

Shionogi and Co Ltd

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.)

1976-07-28

Filing date

1982-01-08

Publication date

1982-08-17

1976-07-28 Priority claimed from JP51090690A external-priority patent/JPS604811B2/ja

1982-01-08 Application filed by Shionogi and Co Ltd filed Critical Shionogi and Co Ltd

1982-01-08 Priority to CA393,848A priority Critical patent/CA1129871A/fr

1982-08-17 Application granted granted Critical

1982-08-17 Publication of CA1129871A publication Critical patent/CA1129871A/fr

Status Expired legal-status Critical Current

Links

150000001539 azetidines Chemical class 0.000 title abstract 2
238000000034 method Methods 0.000 claims abstract description 40
229910052736 halogen Inorganic materials 0.000 claims abstract description 16
150000002367 halogens Chemical class 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
239000001257 hydrogen Substances 0.000 claims abstract description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 12
238000002360 preparation method Methods 0.000 claims abstract description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000003118 aryl group Chemical group 0.000 claims abstract description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 7
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
-1 cupric halogenides Inorganic materials 0.000 claims description 76
150000001875 compounds Chemical class 0.000 claims description 32
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
238000006243 chemical reaction Methods 0.000 claims description 22
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical group [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 17
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 claims description 17
230000002140 halogenating effect Effects 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
229910021590 Copper(II) bromide Inorganic materials 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 9
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
150000002334 glycols Chemical class 0.000 claims description 3
150000003138 primary alcohols Chemical class 0.000 claims description 3
150000000185 1,3-diols Chemical class 0.000 claims description 2
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
229910052753 mercury Inorganic materials 0.000 claims description 2
BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 claims description 2
ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 claims description 2
238000010792 warming Methods 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims 10
150000002431 hydrogen Chemical group 0.000 claims 5
125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 claims 3
125000001309 chloro group Chemical group Cl* 0.000 claims 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 5
239000004599 antimicrobial Substances 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 3
230000003389 potentiating effect Effects 0.000 abstract description 2
239000000460 chlorine Substances 0.000 description 37
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
230000026030 halogenation Effects 0.000 description 13
238000005658 halogenation reaction Methods 0.000 description 13
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
125000002252 acyl group Chemical group 0.000 description 10
238000005907 ketalization reaction Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000007858 starting material Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
150000003839 salts Chemical group 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
238000006567 deketalization reaction Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
125000004423 acyloxy group Chemical group 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000011707 mineral Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
GKEGNIXZSXBQTH-UHFFFAOYSA-N C1=CC=NC=C1.Br.[Br+] Chemical compound C1=CC=NC=C1.Br.[Br+] GKEGNIXZSXBQTH-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
230000031709 bromination Effects 0.000 description 3
238000005893 bromination reaction Methods 0.000 description 3
229940124587 cephalosporin Drugs 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
125000004442 acylamino group Chemical group 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
230000000845 anti-microbial effect Effects 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 2
239000013078 crystal Substances 0.000 description 2
150000005826 halohydrocarbons Chemical class 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
229910052721 tungsten Inorganic materials 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical class CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
OPXYNEYEDHAXOM-UHFFFAOYSA-N 3-oxobutanenitrile Chemical compound CC(=O)CC#N OPXYNEYEDHAXOM-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000295146 Gallionellaceae Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
DTUNKKWUXHBUHO-UHFFFAOYSA-N [Br].Br.C1=CC=NC=C1 Chemical compound [Br].Br.C1=CC=NC=C1 DTUNKKWUXHBUHO-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005138 alkoxysulfonyl group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
229940089960 chloroacetate Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical compound O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002312 hydrocarbylidene group Chemical group 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
238000007689 inspection Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000002730 mercury Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
VTWKXBJHBHYJBI-UHFFFAOYSA-N n-benzylidenehydroxylamine Chemical compound ON=CC1=CC=CC=C1 VTWKXBJHBHYJBI-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004355 nitrogen functional group Chemical group 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
125000002743 phosphorus functional group Chemical group 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
RCOUWKSZRXJXLA-UHFFFAOYSA-N propylbarbital Chemical compound CCCC1(CCC)C(=O)NC(=O)NC1=O RCOUWKSZRXJXLA-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
125000004354 sulfur functional group Chemical group 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 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
238000005406 washing Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA393,848A 1976-07-28 1982-01-08 Derives de l'azetidine Expired CA1129871A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA393,848A CA1129871A (fr)	1976-07-28	1982-01-08	Derives de l'azetidine

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP90690/1976		1976-07-28
JP51090690A JPS604811B2 (ja)	1976-07-28	1976-07-28	メチルケトンのハロゲン化
CA283,351A CA1129870A (fr)	1976-07-28	1977-07-22	Derives d'azetidine
CA393,848A CA1129871A (fr)	1976-07-28	1982-01-08	Derives de l'azetidine

Publications (1)

Publication Number	Publication Date
CA1129871A true CA1129871A (fr)	1982-08-17

Family

ID=27165199

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA393,848A Expired CA1129871A (fr)	1976-07-28	1982-01-08	Derives de l'azetidine

Country Status (1)

Country	Link
CA (1)	CA1129871A (fr)

1982
- 1982-01-08 CA CA393,848A patent/CA1129871A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-08-17	MKEX	Expiry

Publication	Publication Date	Title
US4160085A (en)	1979-07-03	Cyclization to form cephem ring and intermediates therefor
EP0023097B1 (fr)	1984-08-01	Dé-arylméthylation de N-mono- ou N-diarylméthyl-bêta-lactames; azétidinones à activité anti-bactérienne
US4322345A (en)	1982-03-30	2-Azetidinone 4-carboxy derivatives and a process for producing the same
EP0037592A2 (fr)	1981-10-14	Composés contenant le groupement bêta-lactame
US4089956A (en)	1978-05-16	7-Acylamino-8-oxo-3-oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid derivatives and bactericidal compositions and use thereof
US4882429A (en)	1989-11-21	Stereospecific preparation of (3S,4R,5R)-3-(1-hydroxyethyl)-4-benzoyloxy-azeridinones from L-(-)-theonine
CA1129871A (fr)	1982-08-17	Derives de l'azetidine
Ernest	1977	Penicillin-derived diazoketones: Copper (II) catalyzed decomposition in aprotic media
US4283333A (en)	1981-08-11	α-[4-Oxoazetidin-1-yl]-acetic acid compounds useful as intermediates in preparing 1-oxadethiacephalosporins
US4130557A (en)	1978-12-19	Method for the hydrolysis of azetidinothiazoline compounds
US4332722A (en)	1982-06-01	Cyclization to form cephem ring and intermediates therefor
US4008230A (en)	1977-02-15	Process for preparing 3-hydroxy cephalosporins
US4048162A (en)	1977-09-13	Process for preparing 3-hydroxy cephalosporins
US3862182A (en)	1975-01-21	Process to prepare novel antibiotic intermediates
US4560750A (en)	1985-12-24	Cephem compounds and process for preparing the same
EP0122002B1 (fr)	1987-04-15	Procédé de préparation de dérivés d'azétidinone
NZ206831A (en)	1987-04-30	The manufacture of beta-lactams
EP0038661B1 (fr)	1983-12-28	Procédé de préparation de bêta-lactames
EP0096496B1 (fr)	1986-07-23	Procédé de préparation de composés de la pénicilline et de la céphalosporine et produits intermédiaires pour ce procédé
US4187375A (en)	1980-02-05	Process for preparing oxazine ring compounds
DE2615621A1 (de)	1976-10-21	Beta-lactam-antibiotika und -zwischenprodukte sowie ihr herstellungsverfahren
CA1089469A (fr)	1980-11-11	Composes d'oxazolidine
KR800001528B1 (ko)	1980-12-20	세펨환의 중간체의 제조방법
US6011151A (en)	2000-01-04	Process for preparing β-lactam halide compound
US4175076A (en)	1979-11-20	Azetidinone mercury sulfides and process therefor