NO763402L - - Google Patents
Info
- Publication number
- NO763402L NO763402L NO763402A NO763402A NO763402L NO 763402 L NO763402 L NO 763402L NO 763402 A NO763402 A NO 763402A NO 763402 A NO763402 A NO 763402A NO 763402 L NO763402 L NO 763402L
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- compound
- group
- oxo
- spectrum
- Prior art date
Links
- -1 amino, substituted amino Chemical group 0.000 claims description 499
- 150000001875 compounds Chemical class 0.000 claims description 184
- 238000000034 method Methods 0.000 claims description 150
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 77
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000000623 heterocyclic group Chemical group 0.000 claims description 53
- 125000001424 substituent group Chemical group 0.000 claims description 53
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 40
- 125000004442 acylamino group Chemical group 0.000 claims description 37
- 238000002360 preparation method Methods 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000012038 nucleophile Substances 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 17
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 16
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 125000006239 protecting group Chemical group 0.000 claims description 15
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000005110 aryl thio group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 239000002841 Lewis acid Substances 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 150000007517 lewis acids Chemical class 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 230000000269 nucleophilic effect Effects 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 239000002879 Lewis base Substances 0.000 claims description 4
- 150000007527 lewis bases Chemical class 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical group 0.000 claims 2
- 238000002329 infrared spectrum Methods 0.000 description 168
- 239000000203 mixture Substances 0.000 description 168
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 124
- 239000000243 solution Substances 0.000 description 115
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- 239000002904 solvent Substances 0.000 description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 50
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- 125000002393 azetidinyl group Chemical group 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 45
- 238000002844 melting Methods 0.000 description 43
- 230000008018 melting Effects 0.000 description 43
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 125000001931 aliphatic group Chemical group 0.000 description 30
- 150000002148 esters Chemical class 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
- 235000019341 magnesium sulphate Nutrition 0.000 description 24
- 239000002253 acid Substances 0.000 description 23
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical group C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 21
- 238000004440 column chromatography Methods 0.000 description 21
- 238000006722 reduction reaction Methods 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 238000004821 distillation Methods 0.000 description 19
- 230000007062 hydrolysis Effects 0.000 description 18
- 238000006460 hydrolysis reaction Methods 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- 125000002252 acyl group Chemical group 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 17
- 239000002585 base Substances 0.000 description 17
- 238000001816 cooling Methods 0.000 description 17
- 238000010828 elution Methods 0.000 description 17
- 239000000284 extract Substances 0.000 description 17
- 235000017557 sodium bicarbonate Nutrition 0.000 description 17
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 230000007306 turnover Effects 0.000 description 16
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 235000011054 acetic acid Nutrition 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 13
- 239000007983 Tris buffer Substances 0.000 description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000010531 catalytic reduction reaction Methods 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 230000002140 halogenating effect Effects 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 150000007524 organic acids Chemical class 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 229910052757 nitrogen Chemical group 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 7
- NONFLFDSOSZQHR-UHFFFAOYSA-N 3-(trimethylsilyl)propionic acid Chemical compound C[Si](C)(C)CCC(O)=O NONFLFDSOSZQHR-UHFFFAOYSA-N 0.000 description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000003944 tolyl group Chemical group 0.000 description 6
- 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 6
- 125000005023 xylyl group Chemical group 0.000 description 6
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 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 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 229940088710 antibiotic agent Drugs 0.000 description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 5
- 125000004468 heterocyclylthio group Chemical group 0.000 description 5
- 150000007522 mineralic acids Chemical class 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- RHZBRCQIKQUQHQ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetyl chloride Chemical compound C1=CC=C2C(=O)N(CC(=O)Cl)C(=O)C2=C1 RHZBRCQIKQUQHQ-UHFFFAOYSA-N 0.000 description 4
- FJYBBKFECAMBCP-UHFFFAOYSA-N 2-(3-amino-2-oxoazetidin-1-yl)-2-thiophen-2-ylacetic acid Chemical compound O=C1C(N)CN1C(C(O)=O)C1=CC=CS1 FJYBBKFECAMBCP-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005658 halogenation reaction Methods 0.000 description 4
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- DGKCJTPIPPJEOU-UHFFFAOYSA-N methyl 2-[3-amino-2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-4-oxoazetidin-1-yl]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)N(C(C1N)=O)C1SC1=NN=C(C)S1 DGKCJTPIPPJEOU-UHFFFAOYSA-N 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
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- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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- TWRAJPCQPHBABR-UHFFFAOYSA-N magnesium;diazide Chemical compound [Mg+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] TWRAJPCQPHBABR-UHFFFAOYSA-N 0.000 description 1
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- VOMARZSVOZBPSZ-OAHLLOKOSA-N methyl (2R)-2-(benzylideneamino)-2-(4-hydroxyphenyl)acetate Chemical compound N([C@@H](C(=O)OC)C=1C=CC(O)=CC=1)=CC1=CC=CC=C1 VOMARZSVOZBPSZ-OAHLLOKOSA-N 0.000 description 1
- BIXYQFJASLDNOU-QGZVFWFLSA-N methyl (2R)-2-(cinnamylideneamino)-2-phenylacetate Chemical compound COC([C@H](N=CC=CC1=CC=CC=C1)C1=CC=CC=C1)=O BIXYQFJASLDNOU-QGZVFWFLSA-N 0.000 description 1
- FNGPTOLTNNWYEC-QGZVFWFLSA-N methyl (2R)-2-(methylsulfanylmethylideneamino)-2-(4-phenylmethoxyphenyl)acetate Chemical compound C1=CC([C@@H](N=CSC)C(=O)OC)=CC=C1OCC1=CC=CC=C1 FNGPTOLTNNWYEC-QGZVFWFLSA-N 0.000 description 1
- LKVDGXKCOJAOHA-SNVBAGLBSA-N methyl (2R)-2-(methylsulfanylmethylideneamino)-2-phenylacetate Chemical compound CSC=N[C@@H](C(=O)OC)C1=CC=CC=C1 LKVDGXKCOJAOHA-SNVBAGLBSA-N 0.000 description 1
- CIQYCEIWSWMAMM-IDZRBWSNSA-N methyl (2R)-2-[3,5-bis[(1R)-1-[3-(methanesulfonamido)phenyl]-2-methoxy-2-oxoethyl]-1,3,5-triazinan-1-yl]-2-[3-(methanesulfonamido)phenyl]acetate Chemical compound COC(=O)[C@@H](C1=CC(=CC=C1)NS(=O)(=O)C)N1CN(CN(C1)[C@H](C1=CC(=CC=C1)NS(=O)(=O)C)C(=O)OC)[C@H](C1=CC(=CC=C1)NS(=O)(=O)C)C(=O)OC CIQYCEIWSWMAMM-IDZRBWSNSA-N 0.000 description 1
- CQQDENKZGHVZPX-OAHLLOKOSA-N methyl (2r)-2-(benzylideneamino)-2-phenylacetate Chemical compound N([C@@H](C(=O)OC)C=1C=CC=CC=1)=CC1=CC=CC=C1 CQQDENKZGHVZPX-OAHLLOKOSA-N 0.000 description 1
- AEBYTJMSTMTSEA-VJOZVQJDSA-N methyl (2r)-2-[3,5-bis[(1r)-2-methoxy-2-oxo-1-(4-phenylmethoxyphenyl)ethyl]-1,3,5-triazinan-1-yl]-2-(4-phenylmethoxyphenyl)acetate Chemical compound C1=CC([C@H](C(=O)OC)N2CN(CN(C2)[C@@H](C(=O)OC)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)[C@@H](C(=O)OC)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=CC=C1OCC1=CC=CC=C1 AEBYTJMSTMTSEA-VJOZVQJDSA-N 0.000 description 1
- NZJFYMTYPIVXEI-UHFFFAOYSA-N methyl 2-(2-oxo-3-phenoxy-4-phenylazetidin-1-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)N(C1=O)C(C=2C=CC=CC=2)C1OC1=CC=CC=C1 NZJFYMTYPIVXEI-UHFFFAOYSA-N 0.000 description 1
- FZRBDTKZSPSKHT-UHFFFAOYSA-N methyl 2-(3-amino-2-oxoazetidin-1-yl)-2-thiophen-2-ylacetate Chemical compound C=1C=CSC=1C(C(=O)OC)N1CC(N)C1=O FZRBDTKZSPSKHT-UHFFFAOYSA-N 0.000 description 1
- FTIWBUGSHWNCRH-UHFFFAOYSA-N methyl 2-(3-amino-2-oxoazetidin-1-yl)-3-phenylsulfanylpropanoate Chemical compound C1C(N)C(=O)N1C(C(=O)OC)CSC1=CC=CC=C1 FTIWBUGSHWNCRH-UHFFFAOYSA-N 0.000 description 1
- CXEOLWRDHHJIRU-UHFFFAOYSA-N methyl 2-(3-amino-2-oxoazetidin-1-yl)-4-(1,3-benzothiazol-2-ylsulfanyl)-3-methylbut-2-enoate Chemical compound N=1C2=CC=CC=C2SC=1SCC(C)=C(C(=O)OC)N1CC(N)C1=O CXEOLWRDHHJIRU-UHFFFAOYSA-N 0.000 description 1
- QGYKZEOBVKJRSS-UHFFFAOYSA-N methyl 2-(3-amino-2-oxoazetidin-1-yl)-4-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]but-2-enoate Chemical compound N=1N=C(C)SC=1SCC(CSC=1SC(C)=NN=1)=C(C(=O)OC)N1CC(N)C1=O QGYKZEOBVKJRSS-UHFFFAOYSA-N 0.000 description 1
- MPSWXCCOMDSTRQ-UHFFFAOYSA-N methyl 2-(3-azido-2-formyl-4-oxoazetidin-1-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)N1C(C=O)C(N=[N+]=[N-])C1=O MPSWXCCOMDSTRQ-UHFFFAOYSA-N 0.000 description 1
- VGQJNTOFDCQMHA-UHFFFAOYSA-N methyl 2-(3-azido-2-methylsulfanyl-4-oxoazetidin-1-yl)-2-(4-phenylmethoxyphenyl)acetate Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C(C(=O)OC)N1C(SC)C(N=[N+]=[N-])C1=O VGQJNTOFDCQMHA-UHFFFAOYSA-N 0.000 description 1
- XRKXIEOHHZZJLF-UHFFFAOYSA-N methyl 2-(3-azido-2-oxo-4-phenylazetidin-1-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)N(C(C1N=[N+]=[N-])=O)C1C1=CC=CC=C1 XRKXIEOHHZZJLF-UHFFFAOYSA-N 0.000 description 1
- FINBNYXHBHXBKS-UHFFFAOYSA-N methyl 2-(3-azido-2-oxoazetidin-1-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)N1CC(N=[N+]=[N-])C1=O FINBNYXHBHXBKS-UHFFFAOYSA-N 0.000 description 1
- CSHPYGFBALAMFQ-UHFFFAOYSA-N methyl 2-[2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-4-oxo-3-[(2-thiophen-2-ylacetyl)amino]azetidin-1-yl]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)N(C(C1NC(=O)CC=2SC=CC=2)=O)C1SC1=NN=C(C)S1 CSHPYGFBALAMFQ-UHFFFAOYSA-N 0.000 description 1
- UOCKHPFOYGNQJY-UHFFFAOYSA-N methyl 2-[2-methylsulfanyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)N(C1=O)C(SC)C1NC(=O)CC1=CC=CC=C1 UOCKHPFOYGNQJY-UHFFFAOYSA-N 0.000 description 1
- CPVBNQKISONJDV-UHFFFAOYSA-N methyl 2-[2-oxo-4-phenyl-3-(phenylmethoxycarbonylamino)azetidin-1-yl]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)N(C1=O)C(C=2C=CC=CC=2)C1NC(=O)OCC1=CC=CC=C1 CPVBNQKISONJDV-UHFFFAOYSA-N 0.000 description 1
- IOGDCVUITSDIMH-UHFFFAOYSA-N methyl 2-[3,5-bis(2-methoxy-1-naphthalen-1-yl-2-oxoethyl)-1,3,5-triazinan-1-yl]-2-naphthalen-1-ylacetate Chemical compound C1=CC=C2C(C(N3CN(CN(C3)C(C(=O)OC)C=3C4=CC=CC=C4C=CC=3)C(C(=O)OC)C=3C4=CC=CC=C4C=CC=3)C(=O)OC)=CC=CC2=C1 IOGDCVUITSDIMH-UHFFFAOYSA-N 0.000 description 1
- LNRRZXVELGWOLM-UHFFFAOYSA-N methyl 2-[3,5-bis(2-methoxy-2-oxoethyl)-1,3,5-triazinan-1-yl]acetate Chemical compound COC(=O)CN1CN(CC(=O)OC)CN(CC(=O)OC)C1 LNRRZXVELGWOLM-UHFFFAOYSA-N 0.000 description 1
- PRQASPOLCNBFCM-UHFFFAOYSA-N methyl 2-[3,5-bis[1-methoxy-1-oxo-3-(4-phenylmethoxyphenyl)propan-2-yl]-1,3,5-triazinan-1-yl]-3-(4-phenylmethoxyphenyl)propanoate Chemical compound C1N(C(CC=2C=CC(OCC=3C=CC=CC=3)=CC=2)C(=O)OC)CN(C(CC=2C=CC(OCC=3C=CC=CC=3)=CC=2)C(=O)OC)CN1C(C(=O)OC)CC(C=C1)=CC=C1OCC1=CC=CC=C1 PRQASPOLCNBFCM-UHFFFAOYSA-N 0.000 description 1
- WGPYNTJNUYZTKE-UHFFFAOYSA-N methyl 2-[3-(1,3-dioxoisoindol-2-yl)-2-oxoazetidin-1-yl]-2-(furan-2-yl)acetate Chemical compound C1C(N2C(C3=CC=CC=C3C2=O)=O)C(=O)N1C(C(=O)OC)C1=CC=CO1 WGPYNTJNUYZTKE-UHFFFAOYSA-N 0.000 description 1
- LSTJVKCJUGTEEA-UHFFFAOYSA-N methyl 2-[3-(1,3-dioxoisoindol-2-yl)-2-oxoazetidin-1-yl]-2-naphthalen-1-ylacetate Chemical compound C1=CC=C2C(C(N3C(C(N4C(C5=CC=CC=C5C4=O)=O)C3)=O)C(=O)OC)=CC=CC2=C1 LSTJVKCJUGTEEA-UHFFFAOYSA-N 0.000 description 1
- KTIGJRFFMGJTKT-UHFFFAOYSA-N methyl 2-[3-(1,3-dioxoisoindol-2-yl)-2-oxoazetidin-1-yl]-2-thiophen-2-ylacetate Chemical compound C1C(N2C(C3=CC=CC=C3C2=O)=O)C(=O)N1C(C(=O)OC)C1=CC=CS1 KTIGJRFFMGJTKT-UHFFFAOYSA-N 0.000 description 1
- JBJPLSPNXGGKFB-UHFFFAOYSA-N methyl 2-[3-(1,3-dioxoisoindol-2-yl)-2-oxoazetidin-1-yl]-4-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]but-2-enoate Chemical compound C1C(N2C(C3=CC=CC=C3C2=O)=O)C(=O)N1C(C(=O)OC)=C(CSC=1SC(C)=NN=1)CSC1=NN=C(C)S1 JBJPLSPNXGGKFB-UHFFFAOYSA-N 0.000 description 1
- HYRRQLQOUPLONJ-UHFFFAOYSA-N methyl 2-[3-[(2-hydroxyimino-2-phenylacetyl)amino]-2-oxoazetidin-1-yl]-2-naphthalen-1-ylacetate Chemical compound C=1C=CC2=CC=CC=C2C=1C(C(=O)OC)N(C1=O)CC1NC(=O)C(=NO)C1=CC=CC=C1 HYRRQLQOUPLONJ-UHFFFAOYSA-N 0.000 description 1
- UELJMZIWZJBZAX-UHFFFAOYSA-N methyl 2-[3-[(2-hydroxyimino-2-phenylacetyl)amino]-2-oxoazetidin-1-yl]-2-thiophen-2-ylacetate Chemical compound C=1C=CSC=1C(C(=O)OC)N(C1=O)CC1NC(=O)C(=NO)C1=CC=CC=C1 UELJMZIWZJBZAX-UHFFFAOYSA-N 0.000 description 1
- UEVPJXFMEIAYTL-UHFFFAOYSA-N methyl 2-[3-[(2-hydroxyimino-2-phenylacetyl)amino]-2-oxoazetidin-1-yl]-3-(4-hydroxyphenyl)propanoate Chemical compound C1C(NC(=O)C(=NO)C=2C=CC=CC=2)C(=O)N1C(C(=O)OC)CC1=CC=C(O)C=C1 UEVPJXFMEIAYTL-UHFFFAOYSA-N 0.000 description 1
- UYCQQOXBRYYYSZ-UHFFFAOYSA-N methyl 2-[3-[(2-hydroxyimino-2-phenylacetyl)amino]-2-oxoazetidin-1-yl]-3-phenylsulfanylpropanoate Chemical compound C1C(NC(=O)C(=NO)C=2C=CC=CC=2)C(=O)N1C(C(=O)OC)CSC1=CC=CC=C1 UYCQQOXBRYYYSZ-UHFFFAOYSA-N 0.000 description 1
- AYCGDCWOWXVAAE-UHFFFAOYSA-N methyl 2-[3-azido-2-(hydroxymethyl)-4-oxoazetidin-1-yl]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)N1C(CO)C(N=[N+]=[N-])C1=O AYCGDCWOWXVAAE-UHFFFAOYSA-N 0.000 description 1
- SZBDOFWNZVHVGR-UHFFFAOYSA-N methyl 2-amino-2-(4-hydroxyphenyl)acetate Chemical compound COC(=O)C(N)C1=CC=C(O)C=C1 SZBDOFWNZVHVGR-UHFFFAOYSA-N 0.000 description 1
- JNXQDKMSSIYHBP-UHFFFAOYSA-N methyl 3-(3-amino-2-oxoazetidin-1-yl)-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OC)N1CC(N)C1=O JNXQDKMSSIYHBP-UHFFFAOYSA-N 0.000 description 1
- YIQSOZDYGRVLBU-UHFFFAOYSA-N methyl 3-[3-(1,3-dioxoisoindol-2-yl)-2-oxoazetidin-1-yl]-3-phenylpropanoate Chemical compound C1C(N2C(C3=CC=CC=C3C2=O)=O)C(=O)N1C(CC(=O)OC)C1=CC=CC=C1 YIQSOZDYGRVLBU-UHFFFAOYSA-N 0.000 description 1
- HSMFXZQQFYAEFE-UHFFFAOYSA-N methyl 4-(1,3-benzothiazol-2-ylsulfanyl)-2-[3-(1,3-dioxoisoindol-2-yl)-2-oxoazetidin-1-yl]-3-methylbut-2-enoate Chemical compound C1=CC=C2SC(SCC(C)=C(N3C(C(N4C(C5=CC=CC=C5C4=O)=O)C3)=O)C(=O)OC)=NC2=C1 HSMFXZQQFYAEFE-UHFFFAOYSA-N 0.000 description 1
- SBDICIVGADZKBR-UHFFFAOYSA-N methyl 4-(1,3-benzothiazol-2-ylsulfanyl)-2-[3-[(2-hydroxyimino-2-phenylacetyl)amino]-2-oxoazetidin-1-yl]-3-methylbut-2-enoate Chemical compound N=1C2=CC=CC=C2SC=1SCC(C)=C(C(=O)OC)N(C1=O)CC1NC(=O)C(=NO)C1=CC=CC=C1 SBDICIVGADZKBR-UHFFFAOYSA-N 0.000 description 1
- ACWKHWFZFBEVGA-UHFFFAOYSA-N methyl 4-(1,3-benzothiazol-2-ylsulfanyl)-3-(1,3-benzothiazol-2-ylsulfanylmethyl)-2-[3-(1,3-dioxoisoindol-2-yl)-2-oxoazetidin-1-yl]but-2-enoate Chemical compound C1=CC=C2SC(SCC(CSC=3SC4=CC=CC=C4N=3)=C(N3C(C(N4C(C5=CC=CC=C5C4=O)=O)C3)=O)C(=O)OC)=NC2=C1 ACWKHWFZFBEVGA-UHFFFAOYSA-N 0.000 description 1
- OGOMLPDXQOHISI-UHFFFAOYSA-N methyl 4-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-2-[2-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]but-2-enoate Chemical compound N=1N=C(C)SC=1SCC(CSC=1SC(C)=NN=1)=C(C(=O)OC)N(C1=O)CC1NC(=O)COC1=CC=CC=C1 OGOMLPDXQOHISI-UHFFFAOYSA-N 0.000 description 1
- DWHPVIASJOOSOW-UHFFFAOYSA-N methyl 4-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-2-[2-oxo-3-[(2-thiophen-2-ylacetyl)amino]azetidin-1-yl]but-2-enoate Chemical compound N=1N=C(C)SC=1SCC(CSC=1SC(C)=NN=1)=C(C(=O)OC)N(C1=O)CC1NC(=O)CC1=CC=CS1 DWHPVIASJOOSOW-UHFFFAOYSA-N 0.000 description 1
- ZHGNCGJGPQPNSS-UHFFFAOYSA-N methyl 4-[3,5-bis(4-methoxycarbonylphenyl)-1,3,5-triazinan-1-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1N1CN(C=2C=CC(=CC=2)C(=O)OC)CN(C=2C=CC(=CC=2)C(=O)OC)C1 ZHGNCGJGPQPNSS-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 125000006682 monohaloalkyl group Chemical group 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- ZKXYINRKIDSREX-UHFFFAOYSA-N n,n-dipropylhydroxylamine Chemical compound CCCN(O)CCC ZKXYINRKIDSREX-UHFFFAOYSA-N 0.000 description 1
- JVHPKYBRJQNPAT-UHFFFAOYSA-N n-cyclohexyl-2,2-diphenylethenimine Chemical compound C1CCCCC1N=C=C(C=1C=CC=CC=1)C1=CC=CC=C1 JVHPKYBRJQNPAT-UHFFFAOYSA-N 0.000 description 1
- ZABOOJHTOKUIJW-UHFFFAOYSA-N n-cyclohexylcyclohexanamine;4-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-2-[2-oxo-3-[(2-thiophen-2-ylacetyl)amino]azetidin-1-yl]but-2-enoic acid Chemical compound C1CCCCC1NC1CCCCC1.S1C(C)=NN=C1SCC(CSC=1SC(C)=NN=1)=C(C(O)=O)N1C(=O)C(NC(=O)CC=2SC=CC=2)C1 ZABOOJHTOKUIJW-UHFFFAOYSA-N 0.000 description 1
- UULXSTDDDXOTIY-UHFFFAOYSA-N n-iodoacetamide Chemical compound CC(=O)NI UULXSTDDDXOTIY-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- ZDYTZVHWTZRJOM-UHFFFAOYSA-N phenacyl 2-amino-2-(4-phenacyloxyphenyl)acetate;hydrobromide Chemical compound Br.C=1C=C(OCC(=O)C=2C=CC=CC=2)C=CC=1C(N)C(=O)OCC(=O)C1=CC=CC=C1 ZDYTZVHWTZRJOM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
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- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
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- 125000003386 piperidinyl group Chemical group 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- BEBPTRYPELOERP-UHFFFAOYSA-M potassium;methanethiolate Chemical compound [K+].[S-]C BEBPTRYPELOERP-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- NYZPATVKEHZYNP-UHFFFAOYSA-N quinolin-2-yl thiohypochlorite Chemical compound C1=CC=CC2=NC(SCl)=CC=C21 NYZPATVKEHZYNP-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000004400 serine Nutrition 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- 125000005504 styryl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/085—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
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/04—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB40893/75A GB1570278A (en) | 1975-10-06 | 1975-10-06 | O-substituted-2-azetidinone derivatives and the preparation thereof |
GB9476 | 1976-01-02 | ||
GB24276 | 1976-01-05 | ||
GB2150776 | 1976-05-25 | ||
GB2574676 | 1976-06-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO763402L true NO763402L (ja) | 1977-04-12 |
Family
ID=27515653
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO763402A NO763402L (ja) | 1975-10-06 | 1976-10-06 |
Country Status (11)
Country | Link |
---|---|
US (1) | US4181800A (ja) |
BE (1) | BE846934A (ja) |
CH (1) | CH630073A5 (ja) |
DE (1) | DE2645085A1 (ja) |
DK (1) | DK451076A (ja) |
FR (2) | FR2326920A1 (ja) |
GB (1) | GB1570278A (ja) |
IT (1) | IT1071480B (ja) |
NL (1) | NL7611027A (ja) |
NO (1) | NO763402L (ja) |
SE (2) | SE438853B (ja) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL7806860A (nl) * | 1977-07-05 | 1979-01-09 | Farmaceutici Italia | Werkwijze voor het bereiden van met nocardicine verwan- te azetidinonen. |
CA1145347A (en) * | 1977-09-30 | 1983-04-26 | Akira Sato | 2-azetidinone derivatives |
US4195021A (en) * | 1977-10-26 | 1980-03-25 | Eli Lilly And Company | 1,3-Disubstituted 2-azetidinone antibitotics |
EP0005507A1 (de) * | 1978-05-18 | 1979-11-28 | Ciba-Geigy Ag | Fragmentierungsverfahren von 3-(2-Hydroxyimino-acetylamino)-2-oxo-azetidin-Verbindungen und die erhaltenen Verbindungen |
JPS55133355A (en) * | 1979-04-03 | 1980-10-17 | Shionogi & Co Ltd | Inversion of 3-amino group of beta-lactam ring |
EP0021678B1 (en) * | 1979-06-08 | 1984-11-07 | Takeda Chemical Industries, Ltd. | 1-sulpho-2-oxoazetidine derivatives, their production and pharmaceutical compositions thereof |
CA1242188A (en) * | 1979-06-08 | 1988-09-20 | Takeda Pharmaceutical Company Limited | 3-methoxy-2-oxoazetidine derivatives and their production |
US4456467A (en) * | 1980-02-11 | 1984-06-26 | Chevron Research Company | 1-Methylene carbonyl derivatives of 3-aryloxy-4-phenyl-azet-2-one |
JPS56125361A (en) * | 1980-03-07 | 1981-10-01 | Sagami Chem Res Center | Azetidinone compound |
US4337197A (en) | 1980-10-31 | 1982-06-29 | E. R. Squibb & Sons, Inc. | O-sulfated β-lactam hydroxamic acids and intermediates |
AU548727B2 (en) * | 1981-03-12 | 1986-01-02 | Gruppo Lepetit S.P.A. | Beta-lactam acetic acid derivatives |
CA1262128A (en) * | 1981-08-27 | 1989-10-03 | Christian N. Hubschwerlen | .beta.-lactams |
US4443372A (en) * | 1982-06-23 | 1984-04-17 | Chevron Research Company | 1-Alkyl derivatives of 3-aryloxy-4-(2-carbalkoxy)-phenyl-azet-2-ones as plant growth regulators |
US4534786A (en) * | 1982-06-23 | 1985-08-13 | Chevron Research Company | 1-Alkyl derivatives of 3-aryloxy-4-(2-carbalkoxy)-phenyl-azet-2-ones as plant growth regulators |
US4751299A (en) * | 1983-11-18 | 1988-06-14 | Takeda Chemical Industries, Ltd. | Optically active β-lactams and method of their production |
WO1985004877A1 (en) * | 1984-04-16 | 1985-11-07 | Chevron Research Company | 1-methylene carbonyl derivatives of 3-aryloxy-4-phenyl-azet-2-one |
EP0180398A1 (en) * | 1984-10-26 | 1986-05-07 | The Regents Of The University Of California | Synthesis of beta-lactam |
AR027024A1 (es) * | 1999-12-23 | 2003-03-12 | Basf Ag | Procedimiento para la preparacion de n-fosfonometilglicina |
DE10130135A1 (de) * | 2001-06-22 | 2003-01-02 | Basf Ag | Verfahren zur Herstellung von N-Phosphonomethylglycin |
JP2006076990A (ja) * | 2004-03-12 | 2006-03-23 | Bayer Cropscience Ag | 殺虫性ベンゼンジカルボキサミド類 |
DE102004055582A1 (de) * | 2004-11-18 | 2006-05-24 | Bayer Cropscience Ag | N-Heterocyclyl-phthalsäurediamide |
CN102988362B (zh) * | 2005-12-07 | 2014-11-05 | 巴斯利尔药物股份公司 | 单环-内酰胺类抗生素与β-内酰胺酶抑制剂的有效的联合应用 |
AU2012233003B2 (en) * | 2005-12-07 | 2014-12-18 | Basilea Pharmaceutica Ag | Useful combinations of monobactam antibiotics with beta-lactamase inhibitors |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3538092A (en) * | 1968-12-11 | 1970-11-03 | Geigy Chem Corp | Derivatives of n,n',n"-tris(3-mercaptopropionyl)-hfxahydro-s-triazine |
US3923977A (en) * | 1972-08-29 | 1975-12-02 | Fujisawa Pharmaceutical Co | Antibiotic FR-1923 substance |
-
1975
- 1975-10-06 GB GB40893/75A patent/GB1570278A/en not_active Expired
-
1976
- 1976-10-04 BE BE171233A patent/BE846934A/xx not_active IP Right Cessation
- 1976-10-05 IT IT28008/76A patent/IT1071480B/it active
- 1976-10-05 FR FR7629942A patent/FR2326920A1/fr active Granted
- 1976-10-06 NO NO763402A patent/NO763402L/no unknown
- 1976-10-06 DK DK451076A patent/DK451076A/da not_active Application Discontinuation
- 1976-10-06 NL NL7611027A patent/NL7611027A/xx not_active Application Discontinuation
- 1976-10-06 CH CH1264576A patent/CH630073A5/de not_active IP Right Cessation
- 1976-10-06 SE SE7611103A patent/SE438853B/xx not_active Application Discontinuation
- 1976-10-06 DE DE19762645085 patent/DE2645085A1/de not_active Ceased
- 1976-10-06 US US05/730,012 patent/US4181800A/en not_active Expired - Lifetime
-
1977
- 1977-06-14 FR FR7718241A patent/FR2408593B1/fr not_active Expired
-
1981
- 1981-06-10 SE SE8103640A patent/SE8103640L/sv not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
SE438853B (sv) | 1985-05-13 |
GB1570278A (en) | 1980-06-25 |
BE846934A (fr) | 1977-04-04 |
US4181800A (en) | 1980-01-01 |
CH630073A5 (de) | 1982-05-28 |
NL7611027A (nl) | 1977-04-12 |
SE7611103L (sv) | 1977-04-07 |
IT1071480B (it) | 1985-04-10 |
DE2645085A1 (de) | 1977-04-14 |
FR2408593A1 (fr) | 1979-06-08 |
SE8103640L (sv) | 1981-06-10 |
FR2326920B1 (ja) | 1982-08-27 |
FR2408593B1 (fr) | 1982-07-09 |
FR2326920A1 (fr) | 1977-05-06 |
DK451076A (da) | 1977-04-07 |
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