NO793791L - 7-oxo-4-thia-1-a2a-bicyclo(3,2,0) heptanderivater og fremstilling derav. - Google Patents

7-oxo-4-thia-1-a2a-bicyclo(3,2,0) heptanderivater og fremstilling derav.

Info

Publication number: NO793791L
Authority: NO; Norway
Prior art keywords: compound; general formula; formula; meaning; temperature
Prior art date: 1978-11-24

Application number

NO793791A

Other languages

English (en)

Norwegian (no)

Inventor

Maurizio Foglio

Giovanni Franceschi

Cosimo Scarafile

Federico Arcamone

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

1979-11-22

Publication date

1980-05-28

1979-11-22 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1980-05-28 Publication of NO793791L publication Critical patent/NO793791L/no

Links

238000002360 preparation method Methods 0.000 title claims abstract 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 122
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 44
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 42
125000001424 substituent group Chemical group 0.000 claims description 40
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 22
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
-1 acetoxymethyl Chemical group 0.000 claims description 17
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
239000012442 inert solvent Substances 0.000 claims description 15
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 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
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
239000002904 solvent Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
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 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000012320 chlorinating reagent Substances 0.000 claims description 7
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 6
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
150000007530 organic bases Chemical class 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
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 4
125000005633 phthalidyl group Chemical group 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
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 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
208000035473 Communicable disease Diseases 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
125000006000 trichloroethyl group Chemical group 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims 3
101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims 2
101150113676 chr1 gene Proteins 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
229910020667 PBr3 Inorganic materials 0.000 claims 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 claims 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims 1
WSHJJCPTKWSMRR-UHFFFAOYSA-N 4-thia-1-azabicyclo[3.2.0]heptan-7-one Chemical class S1CCN2C(=O)CC21 WSHJJCPTKWSMRR-UHFFFAOYSA-N 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 22
239000000203 mixture Substances 0.000 description 14
229910052799 carbon Inorganic materials 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 6
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
238000010992 reflux Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 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
238000006460 hydrolysis reaction Methods 0.000 description 3
239000002198 insoluble material Substances 0.000 description 3
KFKXSMSQHIOMSO-UHFFFAOYSA-N methyl 2-oxoacetate Chemical compound COC(=O)C=O KFKXSMSQHIOMSO-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
238000004440 column chromatography Methods 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
150000002431 hydrogen Chemical group 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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
238000005055 short column chromatography Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-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
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-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
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 1
229960003324 clavulanic acid 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
125000006575 electron-withdrawing group Chemical group 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
238000004519 manufacturing process Methods 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
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 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
230000005588 protonation Effects 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
238000003786 synthesis reaction Methods 0.000 description 1
229940124597 therapeutic agent Drugs 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
229920002554 vinyl polymer Polymers 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)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO793791A 1978-11-24 1979-11-22 7-oxo-4-thia-1-a2a-bicyclo(3,2,0) heptanderivater og fremstilling derav. NO793791L (no)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
NO793791L true NO793791L (no)	1980-05-28

Family

ID=10501302

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO793791A NO793791L (no)	1978-11-24	1979-11-22	7-oxo-4-thia-1-a2a-bicyclo(3,2,0) heptanderivater og fremstilling derav.

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
US4508649A (en) *	1981-12-11	1985-04-02	Farmitalia Carlo Erba	Process for preparing optically active penems
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
US5229510A (en) *	1983-12-01	1993-07-20	Merck & Co., Inc.	β-lactams useful in determining the amount of elastase in a clinical sample
US4680391A (en) *	1983-12-01	1987-07-14	Merck & Co., Inc.	Substituted azetidinones as anti-inflammatory and antidegenerative agents
US5229381A (en) *	1983-12-01	1993-07-20	Merck & Co., Inc.	Substituted azetidinones as anti-inflammatory and antidegenerative agents
CN1051702C (zh) *	1987-03-19	2000-04-26	科研制药株式会社	杀真菌组合物的制备方法
DE69225821T2 (de) *	1991-03-13	1998-11-05	Otsuka Kagaku Kk	Penamderivate und Verfahren zu deren Herstellung
US5100880A (en) *	1991-03-20	1992-03-31	Merck & Co., Inc.	Novel betalactam elastase inhibitors containing phosphorous acid derivatives at the 4-position of the 2-azetidinone
US5104862A (en) *	1991-03-20	1992-04-14	Merck & Co., Inc.	Bethalactam elastase inhibitors containing phosphorous acid derivatives at the 4-position of the 2-azetidinone
US5348953A (en) *	1991-06-25	1994-09-20	Merck & Co., Inc.	Substituted azetidinones as anti-inflammatory and antidegenerative agents
CA2147129A1 (en) *	1992-10-27	1994-05-11	James B. Doherty	New substituted azetidinones as anti-inflammatory and antidegenerative agents
US5591737A (en) *	1992-12-17	1997-01-07	Merck & Co., Inc.	Substituted azetidinones as anti-inflammatory and antidegenerative agents
TW383308B (en) *	1993-08-24	2000-03-01	Hoffmann La Roche	2-beta-alkenyl penam sulfones as beta-lactamase inhibitors
US5747485A (en) *	1995-04-13	1998-05-05	Merck & Co., Inc.	Substituted azetidiones as anti-inflammatory and antidegenerative agents

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4110165A (en) *	1974-04-20	1978-08-29	Beecham Group Limited	Process for the production of clavulanic acid
US4207323A (en) *	1975-11-21	1980-06-10	Merck & Co., Inc.	6-Substituted methyl penicillins, derivatives and analogues thereof
US4076826A (en) *	1976-04-12	1978-02-28	Merck & Co., Inc.	3-(.beta.-Hydroxyethylidene)-6-(α-Hydroxyethyl)-7-oxo-4-oxaazabicyclo[3.2.0]heptene-2-carboxylic acid and derivatives thereof
GB1563427A (en) *	1977-03-04	1980-03-26	Beecham Group Ltd	Clavulanic acid derivatives
LU77306A1 (de) *	1977-05-09	1979-01-18
EP0000636A1 (de) *	1977-07-13	1979-02-07	Glaxo Group Limited	Penem Verbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Arzneimittel, sowie die Azetidinone gebraucht für ihre Herstellung
US4168314A (en) *	1977-11-17	1979-09-18	Merck & Co., Inc.	6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid
US4155912A (en) *	1977-12-14	1979-05-22	Bristol-Myers Company	2-Methylpenem-3-carboxylic acid antibiotics
US4189493A (en) *	1977-12-28	1980-02-19	Merck & Co., Inc.	N-heterocyclic derivatives of thienamycin
US4123539A (en) *	1977-12-29	1978-10-31	Merck & Co., Inc.	6-Ethylpenicillanic acid
EP0003415A3 (de) *	1978-01-20	1979-08-22	Glaxo Group Limited	Beta-Lactam-Verbindungen, Verfahren zu ihrer Herstellung, sie enthaltende Arzneipräparate und Zwischenprodukte zur Verwendung in ihrer Herstellung
GB2014574A (en) *	1978-02-16	1979-08-30	Glaxo Group Ltd	Lactam Compounds
US4182711A (en) *	1978-04-27	1980-01-08	Bristol-Myers Company	Antibacterial agents of the β-lactam type
US4244965A (en) *	1978-06-15	1981-01-13	Beecham Group Limited	Azetidinoyl ethers
JPS5559193A (en) *	1978-09-20	1980-05-02	Glaxo Group Ltd	Bblactam compound
US4269771A (en) *	1979-04-06	1981-05-26	Farmitalia Carlo Erba	Total synthesis of 7-oxo-4-thia-1-azabicyclo-[3,2,0]-heptane-2-carboxyl derivatives useful as β-lactamase inhibitors and antibacterial agents

1979
- 1979-11-19 US US06/095,790 patent/US4331677A/en not_active Expired - Lifetime
- 1979-11-19 AT AT0736879A patent/AT365594B/de not_active IP Right Cessation
- 1979-11-20 BE BE0/198198A patent/BE880153A/fr not_active IP Right Cessation
- 1979-11-20 IL IL58750A patent/IL58750A/xx unknown
- 1979-11-20 IE IE2222/79A patent/IE49874B1/en not_active IP Right Cessation
- 1979-11-20 NL NL7908464A patent/NL7908464A/nl not_active Application Discontinuation
- 1979-11-20 JP JP14962379A patent/JPS5573685A/ja active Pending
- 1979-11-21 GB GB8205522A patent/GB2093839B/en not_active Expired
- 1979-11-21 AU AU53019/79A patent/AU529597B2/en not_active Ceased
- 1979-11-22 CH CH1042479A patent/CH644128A5/de not_active IP Right Cessation
- 1979-11-22 DK DK495879A patent/DK495879A/da not_active Application Discontinuation
- 1979-11-22 CA CA000340400A patent/CA1139745A/en not_active Expired
- 1979-11-22 SE SE7909667A patent/SE446339B/sv not_active IP Right Cessation
- 1979-11-22 DE DE2947118A patent/DE2947118C2/de not_active Expired
- 1979-11-22 NO NO793791A patent/NO793791L/no unknown
- 1979-11-22 ZA ZA00796333A patent/ZA796333B/xx unknown
- 1979-11-23 SU SU792847112A patent/SU942598A3/ru active
- 1979-11-23 IT IT7927509A patent/IT1209143B/it active
- 1979-11-23 YU YU02877/79A patent/YU287779A/xx unknown
- 1979-11-23 FR FR7928918A patent/FR2449092A1/fr active Granted

Also Published As

Publication number	Publication date
AT365594B (de)	1982-01-25
DK495879A (da)	1980-05-25
DE2947118C2 (de)	1984-03-08
IL58750A (en)	1983-07-31
ZA796333B (en)	1980-11-26
IE792222L (en)	1980-05-24
IT1209143B (it)	1989-07-10
BE880153A (fr)	1980-05-20
AU5301979A (en)	1980-05-29
FR2449092A1 (fr)	1980-09-12
CH644128A5 (de)	1984-07-13
GB2093839A (en)	1982-09-08
SU942598A3 (ru)	1982-07-07
JPS5573685A (en)	1980-06-03
GB2093839B (en)	1983-06-02
IL58750A0 (en)	1980-02-29
SE7909667L (sv)	1980-05-25
YU287779A (en)	1982-10-31
US4331677A (en)	1982-05-25
NL7908464A (nl)	1980-05-28
CA1139745A (en)	1983-01-18
AU529597B2 (en)	1983-06-16
IT7927509A0 (it)	1979-11-23
IE49874B1 (en)	1986-01-08
ATA736879A (de)	1981-06-15
SE446339B (sv)	1986-09-01
DE2947118A1 (de)	1980-06-04
FR2449092B1 (de)	1983-06-03

Publication	Publication Date	Title
NO793791L (no)	1980-05-28	7-oxo-4-thia-1-a2a-bicyclo(3,2,0) heptanderivater og fremstilling derav.
SE449489B (sv)	1987-05-04	Beta-laktam foreningar med antibakteriell och beta-laktam inhiberande aktivitet
JPH0557980B2 (de)	1993-08-25
US4182711A (en)	1980-01-08	Antibacterial agents of the β-lactam type
US4155912A (en)	1979-05-22	2-Methylpenem-3-carboxylic acid antibiotics
JP3479720B2 (ja)	2003-12-15	カルバペネム類の製造法
EP0008514A1 (de)	1980-03-05	Beta-Lactam-Antibiotika, diese enthaltende Zusammensetzungen und ein Verfahren zu ihrer Herstellung
FR2542316A1 (fr)	1984-09-14	Procede de preparation de derives carbapenem, nouveaux intermediaires de synthese et procede de preparation de ces intermediaires
US4269771A (en)	1981-05-26	Total synthesis of 7-oxo-4-thia-1-azabicyclo-[3,2,0]-heptane-2-carboxyl derivatives useful as β-lactamase inhibitors and antibacterial agents
US4704385A (en)	1987-11-03	3-formamido azetidinone antibacterial agents, their preparation and use
EP0031509B1 (de)	1984-10-24	Penem-Derivate
NZ242894A (en)	1994-10-26	Tetracyclic beta-lactam derivatives and pharmaceutical compositions
JPS5823875B2 (ja)	1983-05-18	α−イソプロピリデン−１−アゼチジンアセテ−トおよびその酸の製造法
NZ234329A (en)	1992-03-26	Preparations of penems and pharmaceutical compositions
US4192801A (en)	1980-03-11	Novel phosphorane intermediates for use in preparing penem antibiotics
KR0167718B1 (ko)	1999-01-15	베타-메틸 카르바페넴 유도체 및 이의 제조방법
US5416208A (en)	1995-05-16	Process for penems
GB2036023A (en)	1980-06-25	Bicycloheptane derivatives
KR830002380B1 (ko)	1983-10-25	카바페넴계 항생물질 유도체의 제조방법
JPH04364183A (ja)	1992-12-16	フルオロアルキル化カルバペネム中間体
US4169833A (en)	1979-10-02	Novel phosphorane intermediates for use in preparing penem antibiotics
OIDA et al.	1980	2-(Alkylthio) penem-3-carboxylic Acids. I. Synthesis of 6-Unsubstituted Penems
KR100231498B1 (ko)	1999-11-15	베타메틸 카르바페넴 유도체 및 그의 제조 방법
JPS6254310B2 (de)	1987-11-13
JPS58192874A (ja)	1983-11-10	新規スピロイソキサゾリン誘導体