CH646171A5 - Bicyclic compounds - Google Patents

Bicyclic compounds Download PDF

Info

Publication number: CH646171A5
Authority: CH; Switzerland
Prior art keywords: alkyl; radical; compounds; oxo; rac
Prior art date: 1981-01-30

Application number

CH62081A

Other languages

German (de)

English (en)

Inventor

Erwin Dr Goetschi

Original Assignee

Hoffmann La Roche

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.)

1981-01-30

Filing date

1981-01-30

Publication date

1984-11-15

1981-01-30 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1981-01-30 Priority to CH62081A priority Critical patent/CH646171A5/de

1982-01-08 Priority to CA000393840A priority patent/CA1179675A/fr

1982-01-14 Priority to NZ199487A priority patent/NZ199487A/en

1982-01-19 Priority to IT19187/82A priority patent/IT1153416B/it

1982-01-21 Priority to NL8200217A priority patent/NL8200217A/nl

1982-01-22 Priority to DE19823201957 priority patent/DE3201957A1/de

1982-01-22 Priority to PH26771A priority patent/PH19227A/en

1982-01-22 Priority to ZA82446A priority patent/ZA82446B/xx

1982-01-25 Priority to IL64859A priority patent/IL64859A/xx

1982-01-25 Priority to DK32082A priority patent/DK32082A/da

1982-01-25 Priority to AU79798/82A priority patent/AU7979882A/en

1982-01-26 Priority to BE0/207139A priority patent/BE891899A/fr

1982-01-28 Priority to FR828201345A priority patent/FR2499081B1/fr

1982-01-28 Priority to LU83906A priority patent/LU83906A1/de

1982-01-29 Priority to SE8200515A priority patent/SE8200515L/xx

1982-01-29 Priority to IE197/82A priority patent/IE52421B1/en

1982-01-29 Priority to AT0034082A priority patent/AT377762B/de

1982-01-29 Priority to GB8202523A priority patent/GB2092147B/en

1982-01-29 Priority to JP57011936A priority patent/JPS57144285A/ja

1984-11-15 Publication of CH646171A5 publication Critical patent/CH646171A5/de

Links

125000002619 bicyclic group Chemical group 0.000 title claims abstract description 9
-1 C1-3-alkoxycarbonyl Chemical group 0.000 claims abstract description 148
150000001875 compounds Chemical class 0.000 claims abstract description 53
150000003839 salts Chemical class 0.000 claims abstract description 35
150000002148 esters Chemical class 0.000 claims abstract description 27
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 24
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 23
229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
239000001301 oxygen Substances 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
150000004677 hydrates Chemical class 0.000 claims abstract description 13
150000007524 organic acids Chemical class 0.000 claims abstract description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
150000002894 organic compounds Chemical group 0.000 claims abstract description 7
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 5
238000011282 treatment Methods 0.000 claims abstract description 5
208000035473 Communicable disease Diseases 0.000 claims abstract description 4
238000011321 prophylaxis Methods 0.000 claims abstract description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 6
239000000460 chlorine Substances 0.000 claims description 37
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
150000003254 radicals Chemical class 0.000 claims description 22
229910052717 sulfur Inorganic materials 0.000 claims description 22
239000011593 sulfur Substances 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
229920006395 saturated elastomer Polymers 0.000 claims description 19
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
238000000034 method Methods 0.000 claims description 17
125000005842 heteroatom Chemical group 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
239000011737 fluorine Substances 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
125000001246 bromo group Chemical group Br* 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000004043 oxo group Chemical group O=* 0.000 claims description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
239000000825 pharmaceutical preparation Substances 0.000 claims description 6
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000000464 thioxo group Chemical group S=* 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
229920001577 copolymer Chemical class 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical group ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
150000002923 oximes Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
239000005711 Benzoic acid Substances 0.000 claims description 2
239000004593 Epoxy Substances 0.000 claims description 2
229910006069 SO3H Inorganic materials 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
235000010233 benzoic acid Nutrition 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
239000005864 Sulphur Substances 0.000 abstract 1
125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
239000000243 solution Substances 0.000 description 88
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 86
238000006243 chemical reaction Methods 0.000 description 38
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
239000000203 mixture Substances 0.000 description 31
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
229910001868 water Inorganic materials 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
239000003921 oil Substances 0.000 description 20
235000019198 oils Nutrition 0.000 description 20
239000012074 organic phase Substances 0.000 description 16
239000000741 silica gel Substances 0.000 description 16
229910002027 silica gel Inorganic materials 0.000 description 16
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
239000013078 crystal Substances 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
239000012071 phase Substances 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
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 10
239000000047 product Substances 0.000 description 10
239000007858 starting material Substances 0.000 description 10
125000004149 thio group Chemical group *S* 0.000 description 10
ITAPQTGSOLYCLH-UHFFFAOYSA-N 4-[(2-methyl-1,3-dioxolan-2-yl)methyl]azetidin-2-one Chemical compound C1OC(CC2CC(N2)=O)(C)OC1 ITAPQTGSOLYCLH-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000002425 crystallisation Methods 0.000 description 9
230000008025 crystallization Effects 0.000 description 9
239000011734 sodium Substances 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
150000002431 hydrogen Chemical class 0.000 description 8
239000002904 solvent Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000003480 eluent Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
238000007363 ring formation reaction Methods 0.000 description 6
239000011780 sodium chloride Substances 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
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
239000012300 argon atmosphere Substances 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000011097 chromatography purification Methods 0.000 description 5
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
238000003756 stirring Methods 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
NJAWPFHASBAMLE-UHFFFAOYSA-N ethyl 3-amino-4-(2-methyl-1,3-dioxolan-2-yl)butanoate Chemical compound NC(CC(=O)OCC)CC1(C)OCCO1 NJAWPFHASBAMLE-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
RLBQTMYBGOKQBU-UHFFFAOYSA-N 2-(2-methyl-1,3-dioxolan-2-yl)acetaldehyde Chemical compound O=CCC1(C)OCCO1 RLBQTMYBGOKQBU-UHFFFAOYSA-N 0.000 description 3
VNAJIZNBAHUGRS-UHFFFAOYSA-N 4-(3-bromo-2,2-dimethoxypropyl)azetidin-2-one Chemical compound BrCC(CC1CC(N1)=O)(OC)OC VNAJIZNBAHUGRS-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical group O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 3
229910052681 coesite Inorganic materials 0.000 description 3
229910052906 cristobalite Inorganic materials 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000007257 deesterification reaction Methods 0.000 description 3
XWEOGMYZFCHQNT-UHFFFAOYSA-N ethyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate Chemical compound CCOC(=O)CC1(C)OCCO1 XWEOGMYZFCHQNT-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 3
239000008055 phosphate buffer solution Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
229910052682 stishovite Inorganic materials 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
229910052905 tridymite Inorganic materials 0.000 description 3
DCJCOLNFKFQFDC-YUMQZZPRSA-N (3S,4S)-3-ethyl-4-[(2-methyl-1,3-dioxolan-2-yl)methyl]azetidin-2-one Chemical compound C(C)[C@@H]1C(N[C@H]1CC1(OCCO1)C)=O DCJCOLNFKFQFDC-YUMQZZPRSA-N 0.000 description 2
BKGLGDXGKJTHOR-YUMQZZPRSA-N (3S,4S)-4-(3-bromo-2,2-dimethoxypropyl)-3-ethylazetidin-2-one Chemical compound BrCC(C[C@H]1[C@@H](C(N1)=O)CC)(OC)OC BKGLGDXGKJTHOR-YUMQZZPRSA-N 0.000 description 2
125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
101100132433 Arabidopsis thaliana VIII-1 gene Proteins 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
238000013375 chromatographic separation Methods 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000004042 decolorization Methods 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 2
RPZBLMVYFMNYPC-UHFFFAOYSA-N ethyl 4-(2-methyl-1,3-dioxolan-2-yl)but-2-enoate Chemical compound CCOC(=O)C=CCC1(C)OCCO1 RPZBLMVYFMNYPC-UHFFFAOYSA-N 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
239000007789 gas Substances 0.000 description 2
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
150000002373 hemiacetals Chemical class 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
PELJISAVHGXLAL-UHFFFAOYSA-N iodomethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCI PELJISAVHGXLAL-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
229910003002 lithium salt Inorganic materials 0.000 description 2
159000000002 lithium salts Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
230000000269 nucleophilic effect Effects 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 2
230000004962 physiological condition Effects 0.000 description 2
239000012264 purified product Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000000630 rising effect Effects 0.000 description 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
235000019345 sodium thiosulphate Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
239000005051 trimethylchlorosilane Substances 0.000 description 2
GQYWSVHXZPDQQT-SFYZADRCSA-N (3R,4R)-3-(2-hydroxypropan-2-yl)-4-[(2-methyl-1,3-dioxolan-2-yl)methyl]azetidin-2-one Chemical compound OC(C)(C)[C@@H]1C(N[C@@H]1CC1(OCCO1)C)=O GQYWSVHXZPDQQT-SFYZADRCSA-N 0.000 description 1
GQYWSVHXZPDQQT-YUMQZZPRSA-N (3R,4S)-3-(2-hydroxypropan-2-yl)-4-[(2-methyl-1,3-dioxolan-2-yl)methyl]azetidin-2-one Chemical compound OC(C)(C)[C@@H]1C(N[C@H]1CC1(OCCO1)C)=O GQYWSVHXZPDQQT-YUMQZZPRSA-N 0.000 description 1
125000006559 (C1-C3) alkylamino group Chemical group 0.000 description 1
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125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
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125000005999 2-bromoethyl group Chemical group 0.000 description 1
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JQDOSKYNGOYQNP-UHFFFAOYSA-N 3-amino-4-(2-methyl-1,3-dioxolan-2-yl)butanoic acid Chemical compound NC(CC(=O)O)CC1(C)OCCO1 JQDOSKYNGOYQNP-UHFFFAOYSA-N 0.000 description 1
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WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
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241000894006 Bacteria Species 0.000 description 1
ZDPXVVSYSWAYQN-UHFFFAOYSA-N CC1(OCCO1)CC(CC(=O)N)N Chemical compound CC1(OCCO1)CC(CC(=O)N)N ZDPXVVSYSWAYQN-UHFFFAOYSA-N 0.000 description 1
UIOAQJNADLELPQ-UHFFFAOYSA-N C[C]1OCCO1 Chemical group C[C]1OCCO1 UIOAQJNADLELPQ-UHFFFAOYSA-N 0.000 description 1
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238000007445 Chromatographic isolation Methods 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
108090000371 Esterases Proteins 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
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150000000994 L-ascorbates Chemical class 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
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HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
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239000012298 atmosphere Substances 0.000 description 1
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230000031709 bromination Effects 0.000 description 1
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239000012876 carrier material Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
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WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
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238000005886 esterification reaction Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
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235000011852 gelatine desserts Nutrition 0.000 description 1
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230000036571 hydration Effects 0.000 description 1
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150000003840 hydrochlorides Chemical class 0.000 description 1
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238000006460 hydrolysis reaction Methods 0.000 description 1
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230000002401 inhibitory effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
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ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
IWPOSDLLFZKGOW-UHFFFAOYSA-N oct-3-enoic acid Chemical compound CCCCC=CCC(O)=O IWPOSDLLFZKGOW-UHFFFAOYSA-N 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
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239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 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
150000003892 tartrate salts Chemical class 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
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239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003952 β-lactams Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings

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

CH62081A 1981-01-30 1981-01-30 Bicyclic compounds CH646171A5 (en)

Priority Applications (19)

Application Number	Priority Date	Filing Date	Title
CH62081A CH646171A5 (en)	1981-01-30	1981-01-30	Bicyclic compounds
CA000393840A CA1179675A (fr)	1981-01-30	1982-01-08	Derives du 7-oxo-1-azabicyclo ¬3,2,0\| heptene-2-
NZ199487A NZ199487A (en)	1981-01-30	1982-01-14	Azabicycloheptene derivatives,intermediates and pharmaceutical compositions
IT19187/82A IT1153416B (it)	1981-01-30	1982-01-19	Composti biciclici
NL8200217A NL8200217A (nl)	1981-01-30	1982-01-21	Bicyclische verbindingen, werkwijzen ter bereiding ervan, alsmede farmaceutische preparaten, die deze bicyclische verbindingen bevatten.
DE19823201957 DE3201957A1 (de)	1981-01-30	1982-01-22	Derivate der 7-oxo-1-azabicyclo-(3.2.0)-hept-2-en-2-carbonsaeure
PH26771A PH19227A (en)	1981-01-30	1982-01-22	Bicyclic compounds
ZA82446A ZA82446B (en)	1981-01-30	1982-01-22	Bicyclic compounds
IL64859A IL64859A (en)	1981-01-30	1982-01-25	7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid derivatives,their preparation and pharmaceutical compositions comprising them
DK32082A DK32082A (da)	1981-01-30	1982-01-25	Fremgangsmaade til fremstilling af bicycliske forbindelser
AU79798/82A AU7979882A (en)	1981-01-30	1982-01-25	7-oxo-1-azabicyclo(3,2,0)hept-2-ene derivatives
BE0/207139A BE891899A (fr)	1981-01-30	1982-01-26	Derives de 7-oxo-1-azabicyclo(3-2-0) hept-2-ene, leur preparation et leur application en tant que medicaments
FR828201345A FR2499081B1 (fr)	1981-01-30	1982-01-28	Derives de 7-oxo-1-azabicyclo (3-2-0) hept-2-ene, leur preparation et leur application en tant que medicaments
LU83906A LU83906A1 (de)	1981-01-30	1982-01-28	Bicyclische verbindungen
SE8200515A SE8200515L (sv)	1981-01-30	1982-01-29	Bicykliska foreningar
IE197/82A IE52421B1 (en)	1981-01-30	1982-01-29	Carbapenen compounds
AT0034082A AT377762B (de)	1981-01-30	1982-01-29	Verfahren zur herstellung von neuen bicyclischen verbindungen
GB8202523A GB2092147B (en)	1981-01-30	1982-01-29	Azabicycloheptene
JP57011936A JPS57144285A (en)	1981-01-30	1982-01-29	Bicyclic compound

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH62081A CH646171A5 (en)	1981-01-30	1981-01-30	Bicyclic compounds

Publications (1)

Publication Number	Publication Date
CH646171A5 true CH646171A5 (en)	1984-11-15

Family

ID=4191247

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH62081A CH646171A5 (en)	1981-01-30	1981-01-30	Bicyclic compounds

Country Status (4)

Country	Link
JP (1)	JPS57144285A (fr)
BE (1)	BE891899A (fr)
CH (1)	CH646171A5 (fr)
ZA (1)	ZA82446B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57175192A (en) *	1981-04-22	1982-10-28	Sankyo Co Ltd	7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid derivative
JPS58103388A (ja) *	1981-12-11	1983-06-20	Sankyo Co Ltd	カルバペネム誘導体
EP0184844A1 (fr) *	1984-12-13	1986-06-18	Merck & Co. Inc.	1-Méthylcarbapénèmes ayant un substituant, relié par un pont alkylène-thio, en position 2
EP0186057A1 (fr) *	1984-12-13	1986-07-02	Merck & Co. Inc.	Carbapénèmes ayant en position 2 un substituant relié par un pont alkylène-hétéroatome

1981
- 1981-01-30 CH CH62081A patent/CH646171A5/de not_active IP Right Cessation
1982
- 1982-01-22 ZA ZA82446A patent/ZA82446B/xx unknown
- 1982-01-26 BE BE0/207139A patent/BE891899A/fr not_active IP Right Cessation
- 1982-01-29 JP JP57011936A patent/JPS57144285A/ja active Pending

Also Published As

Publication number	Publication date
ZA82446B (en)	1982-12-29
JPS57144285A (en)	1982-09-06
BE891899A (fr)	1982-07-26

Legal Events

Date	Code	Title	Description
1987-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE3587126T2 (de)	1993-10-07	Carbapenem-Derivate und sie enthaltende Zusammensetzung.
DE69429742T2 (de)	2002-06-06	2-[1-(1,3-Thiazolin-2-yl)azetidin-3-yl]thio-carbapenem-Derivate
CH657853A5 (de)	1986-09-30	Carbapenemderivate, deren herstellung und solche verbindungen enthaltende praeparate.
CH640856A5 (en)	1984-01-31	Process for preparing novel derivatives of 1-carba-2-penem-3-carboxylic acid
DE3321864A1 (de)	1983-12-22	Carbapenem-derivate, verfahren zu ihrer herstellung und pharmazeutische mittel
DE69319764T2 (de)	1998-11-26	Verfahren zur Herstellung von Beta-Lactamderivaten und Zwischenprodukt für ihre Synthese
DE3109086C2 (fr)	1991-05-02
US4262009A (en)	1981-04-14	6- And 1,1-disubstituted-1-carbadethiapen-2-em-3-carboxylic acid
DE3312533C2 (fr)	1991-08-14
CH666274A5 (de)	1988-07-15	Cephalosporin-antibiotika.
DE3334937C2 (fr)	1991-05-02
EP0300278A2 (fr)	1989-01-25	Procédé de préparation de pyrroles 2-substituées
US4806637A (en)	1989-02-21	6-(Hydroxyethyl)-2-(heterocyclylthio)-penem-3-carboxylates
EP0378850B1 (fr)	1994-04-06	Pyrido(2,3-d)pyrimidines substituées
DD228258A5 (de)	1985-10-09	Verfahren zur herstellung von carbapenem-derivaten
DE3317742C2 (fr)	1991-08-29
CH651037A5 (de)	1985-08-30	Penem-3-carbonsaeurederivate und verfahren zu deren herstellung.
CH631987A5 (de)	1982-09-15	Verfahren zur herstellung von 7-acylamino-8-oxo-3-oxa-1-azabicyclo(4.2.0)octan-2-carbonsaeure-derivaten.
DD156911A5 (de)	1982-09-29	Verfahren zur herstellung von 7-oxo-1-azabicyclo(3,2,0)hept-2-ene-2-carbonsaeure-derivaten
DE3201957A1 (de)	1982-09-09	Derivate der 7-oxo-1-azabicyclo-(3.2.0)-hept-2-en-2-carbonsaeure
AT395590B (de)	1993-01-25	2-methoxymethylpenemverbindungen, verfahren zu deren herstellung und sie enthaltende pharmazeutische zusammensetzungen
EP0330057A2 (fr)	1989-08-30	Pyrimidines substituées
DE3344317C2 (fr)	1992-02-27
CH646171A5 (en)	1984-11-15	Bicyclic compounds
DE2751597A1 (de)	1978-05-24	3-(2-aminoaethylthio)-6-(1-hydroxyaethyl)-7-oxo-1-azabicyclo eckige klammer auf 3.2.0 eckige klammer zu hept-2-en- 2-carbonsaeure