NL7908464A - 7-oxo-4-thia-1-aza-bicyclo3,2,0heptaanderivaten en hun bereiding. - Google Patents

7-oxo-4-thia-1-aza-bicyclo3,2,0heptaanderivaten en hun bereiding. Download PDF

Info

Publication number: NL7908464A
Authority: NL; Netherlands
Prior art keywords: formula; compound; cooch3; meanings; substituents
Prior art date: 1978-11-24

Application number

NL7908464A

Other languages

English (en)

Dutch (nl)

Original Assignee

Erba Farmitalia

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.)

1978-11-24

Filing date

1979-11-20

Publication date

1980-05-28

1979-11-20 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1980-05-28 Publication of NL7908464A publication Critical patent/NL7908464A/nl

Links

238000002360 preparation method Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 125
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 57
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 43
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 21
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 20
-1 trichlorethyl Chemical group 0.000 claims description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 17
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 16
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 16
239000012442 inert solvent Substances 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
239000000741 silica gel Substances 0.000 claims description 12
229910002027 silica gel Inorganic materials 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
239000012320 chlorinating reagent Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
150000007530 organic bases Chemical class 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
125000005633 phthalidyl group Chemical group 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 3
208000035473 Communicable disease Diseases 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
238000006317 isomerization reaction Methods 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000006000 trichloroethyl group Chemical group 0.000 claims description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims 5
229960001866 silicon dioxide Drugs 0.000 claims 5
238000004519 manufacturing process Methods 0.000 claims 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
150000001805 chlorine compounds Chemical class 0.000 claims 2
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
241000283986 Lepus Species 0.000 claims 1
101150064767 NNR1 gene Proteins 0.000 claims 1
239000013543 active substance Substances 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 claims 1
210000000988 bone and bone Anatomy 0.000 claims 1
VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical compound [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
239000000047 product Substances 0.000 description 16
239000000203 mixture Substances 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-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 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
238000005949 ozonolysis reaction Methods 0.000 description 5
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 4
238000004040 coloring Methods 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000005055 short column chromatography Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
229940125797 compound 12 Drugs 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
FMWSHZRIJXQMOO-UHFFFAOYSA-N Glutinic acid Natural products OC(=O)C=C(C)CCC1(C)C(C)CCC2(C)C1CCC=C2C(O)=O FMWSHZRIJXQMOO-UHFFFAOYSA-N 0.000 description 1
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
229960004419 dimethyl fumarate Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000010902 straw Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- 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
- 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

Landscapes

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

NL7908464A 1978-11-24 1979-11-20 7-oxo-4-thia-1-aza-bicyclo3,2,0heptaanderivaten en hun bereiding. NL7908464A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7845966		1978-11-24
GB7845966		1978-11-24

Publications (1)

Publication Number	Publication Date
NL7908464A true NL7908464A (nl)	1980-05-28

Family

ID=10501302

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7908464A NL7908464A (nl)	1978-11-24	1979-11-20	7-oxo-4-thia-1-aza-bicyclo3,2,0heptaanderivaten en hun bereiding.

Country Status (20)

Country	Link
US (1)	US4331677A (de)
JP (1)	JPS5573685A (de)
AT (1)	AT365594B (de)
AU (1)	AU529597B2 (de)
BE (1)	BE880153A (de)
CA (1)	CA1139745A (de)
CH (1)	CH644128A5 (de)
DE (1)	DE2947118C2 (de)
DK (1)	DK495879A (de)
FR (1)	FR2449092A1 (de)
GB (1)	GB2093839B (de)
IE (1)	IE49874B1 (de)
IL (1)	IL58750A (de)
IT (1)	IT1209143B (de)
NL (1)	NL7908464A (de)
NO (1)	NO793791L (de)
SE (1)	SE446339B (de)
SU (1)	SU942598A3 (de)
YU (1)	YU287779A (de)
ZA (1)	ZA796333B (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4361513A (en) *	1980-12-11	1982-11-30	Pfizer Inc.	Esters of penicillanic acid sulfone
US4474698A (en) *	1980-12-11	1984-10-02	Pfizer Inc.	Process for preparing esters of penicillanic acid sulfone
NL8204720A (nl) *	1981-12-11	1983-07-01	Erba Farmitalia	Werkwijze voor het bereiden van optisch actieve penemverbindingen.
NO831160L (no) *	1982-04-08	1983-10-10	Erba Farmitalia	Fremstilling av substituerte penem-derivater
JPS58225091A (ja) *	1982-06-21	1983-12-27	Taiho Yakuhin Kogyo Kk	ペニシリン誘導体及びその製造法
US4562073A (en) *	1982-12-24	1985-12-31	Taiho Pharmaceutical Company Limited	Penicillin derivatives
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1979
- 1979-11-19 AT AT0736879A patent/AT365594B/de not_active IP Right Cessation
- 1979-11-19 US US06/095,790 patent/US4331677A/en not_active Expired - Lifetime
- 1979-11-20 IL IL58750A patent/IL58750A/xx unknown
- 1979-11-20 JP JP14962379A patent/JPS5573685A/ja active Pending
- 1979-11-20 NL NL7908464A patent/NL7908464A/nl not_active Application Discontinuation
- 1979-11-20 BE BE0/198198A patent/BE880153A/fr not_active IP Right Cessation
- 1979-11-20 IE IE2222/79A patent/IE49874B1/en not_active IP Right Cessation
- 1979-11-21 AU AU53019/79A patent/AU529597B2/en not_active Ceased
- 1979-11-21 GB GB8205522A patent/GB2093839B/en not_active Expired
- 1979-11-22 SE SE7909667A patent/SE446339B/sv not_active IP Right Cessation
- 1979-11-22 ZA ZA00796333A patent/ZA796333B/xx unknown
- 1979-11-22 DK DK495879A patent/DK495879A/da not_active Application Discontinuation
- 1979-11-22 CH CH1042479A patent/CH644128A5/de not_active IP Right Cessation
- 1979-11-22 CA CA000340400A patent/CA1139745A/en not_active Expired
- 1979-11-22 DE DE2947118A patent/DE2947118C2/de not_active Expired
- 1979-11-22 NO NO793791A patent/NO793791L/no unknown
- 1979-11-23 FR FR7928918A patent/FR2449092A1/fr active Granted
- 1979-11-23 IT IT7927509A patent/IT1209143B/it active
- 1979-11-23 SU SU792847112A patent/SU942598A3/ru active
- 1979-11-23 YU YU02877/79A patent/YU287779A/xx unknown

Also Published As

Publication number	Publication date
IE49874B1 (en)	1986-01-08
YU287779A (en)	1982-10-31
JPS5573685A (en)	1980-06-03
US4331677A (en)	1982-05-25
GB2093839A (en)	1982-09-08
DE2947118A1 (de)	1980-06-04
DE2947118C2 (de)	1984-03-08
FR2449092A1 (fr)	1980-09-12
AT365594B (de)	1982-01-25
FR2449092B1 (de)	1983-06-03
DK495879A (da)	1980-05-25
IL58750A0 (en)	1980-02-29
SE7909667L (sv)	1980-05-25
SE446339B (sv)	1986-09-01
SU942598A3 (ru)	1982-07-07
ATA736879A (de)	1981-06-15
GB2093839B (en)	1983-06-02
CA1139745A (en)	1983-01-18
AU5301979A (en)	1980-05-29
IL58750A (en)	1983-07-31
NO793791L (no)	1980-05-28
IT7927509A0 (it)	1979-11-23
AU529597B2 (en)	1983-06-16
BE880153A (fr)	1980-05-20
CH644128A5 (de)	1984-07-13
IT1209143B (it)	1989-07-10
IE792222L (en)	1980-05-24
ZA796333B (en)	1980-11-26

Legal Events

Date	Code	Title
1985-01-01	A85	Still pending on 85-01-01
1985-02-01	BA	A request for search or an international-type search has been filed
1985-05-01	BB	A search report has been drawn up
1986-11-03	BC	A request for examination has been filed
1992-07-01	BV	The patent application has lapsed

Publication	Publication Date	Title
NL7908464A (nl)	1980-05-28	7-oxo-4-thia-1-aza-bicyclo3,2,0heptaanderivaten en hun bereiding.
Overman et al.	1985	A convenient synthesis of 4-unsubstituted. beta.-lactams
Mori et al.	1991	New synthesis of 4-acetoxy-2-azetidinones by use of electrochemical oxidation
Palomo et al.	1997	A Contribution to the Asymmetric Synthesis of 3‐Amino β‐Lactams: The Diastereoselective [2+ 2] Cycloaddition Reaction of Chiral Aminoketene Equivalents with Enolizable Aldehyde‐Derived Imines
DE3428049C2 (de)	1989-09-28
DE68906945T2 (de)	1993-10-14	Verfahren für Carbapenem-Zwischenprodukte.
DE3006273A1 (de)	1980-09-04	Verbindungen mit beta - lactamgeruest, verfahren zu deren herstellung und diese enthaltende pharmazeutische zubereitungen
CH653034A5 (de)	1985-12-13	2-thioxopenam-3-carbonsaeurederivate sowie ihre tautomere und diese erstgenannten verbindungen enthaltendes pharmazeutisches praeparat.
DE3382761T2 (de)	1995-03-09	Verfahren zur Herstellung von Penem-Verbindungen.
EP1753717A1 (de)	2007-02-21	Verfahren zur herstellung von diphenyl-azetidinon-derivaten
Shono et al.	1992	Electroorganic chemistry 139. Electroreductive decyanation of nitriles and its application to synthesis of α-alkylamines
Udding et al.	1994	Xanthate Transfer Addition of a Glycine Radical Equivalent to Alkenes. A Novel Route to. alpha.-Amino Acid Derivatives
US4560508A (en)	1985-12-24	4-Cyano-2-azetidinones and production thereof
NL193407C (nl)	1999-09-06	Werkwijze voor de bereiding van 3-exomethyleencefamderivaten.
Wang et al.	2003	Elimination of benzotriazolyl group in N-(α-benzotriazol-1-ylalkyl) amides and N-(α-benzotriazol-1-ylalkyl) sulfonamides: their self-coupling and cross-coupling reactions with carbonyl compounds
Meth-Cohn et al.	1989	Synthesis of halothiophene S, C-ylides and the corresponding 1, 4-oxathiocines
CH641448A5 (de)	1984-02-29	Verfahren zur herstellung von beta-lactamen.
Ishibashi et al.	1995	Uncatalyzed cationic olefin cyclizations of N-vinylic α-chloro-α-thioacetamides. Formation of β-and γ-lactams
US6867297B1 (en)	2005-03-15	Process for synthesizing 4-substituted azetidinone derivatives
JP2719624B2 (ja)	1998-02-25	４−アシロキシ−２−アゼチジノン誘導体の製造法
RU2134685C1 (ru)	1999-08-20	2-бром- и 2-нитрокси-производные 3,3-дибром-4-оксоазетидинов, способ их получения, способ подавления роста опухолевых клеток, 2-хлор-производные 3,3-дибром-4-оксоазетидинов
DE69432777T2 (de)	2004-03-18	Verfahren zur synthese von 4-substituierten azetidinon-derivaten
Barrett et al.	2002	Application of lanthanide catalysis in the penicillin to cephalosporin conversion
SI9700028A (en)	1997-08-31	Novel derivatives of 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines, their preparation processes and their use
DE69717059T2 (de)	2003-07-31	Verfahren zur Herstellung von Cyclohexylazetidinon