CS219273B2 - Method of making the inhibitor of the beta-lactamase - Google Patents

Method of making the inhibitor of the beta-lactamase Download PDF

Info

Publication number: CS219273B2
Authority: CS; Czechoslovakia
Prior art keywords: compound; formula; defined above; mmol; coor
Prior art date: 1979-04-06

Application number

CS802289A

Other languages

Czech (cs)

English (en)

Inventor

Paolo Lambardi

Giovanni Franceschi

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.)

1979-04-06

Filing date

1980-04-02

Publication date

1983-03-25

1980-04-02 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1983-03-25 Publication of CS219273B2 publication Critical patent/CS219273B2/cs

Links

239000003112 inhibitor Substances 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title description 2
108090000204 Dipeptidase 1 Proteins 0.000 title 1
102000006635 beta-lactamase Human genes 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 48
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 10
-1 acetoxymethyl Chemical group 0.000 claims abstract description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims abstract description 7
OEYMQQDJCUHKQS-UHFFFAOYSA-N (4-oxoazetidin-2-yl) acetate Chemical compound CC(=O)OC1CC(=O)N1 OEYMQQDJCUHKQS-UHFFFAOYSA-N 0.000 claims abstract description 5
238000006243 chemical reaction Methods 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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 10
238000005949 ozonolysis reaction Methods 0.000 claims description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
238000007039 two-step reaction Methods 0.000 claims description 2
239000000203 mixture Substances 0.000 abstract description 19
125000000217 alkyl group Chemical group 0.000 abstract description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
125000000623 heterocyclic group Chemical group 0.000 abstract 2
125000003118 aryl group Chemical group 0.000 abstract 1
238000010438 heat treatment Methods 0.000 abstract 1
125000005842 heteroatom Chemical group 0.000 abstract 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 abstract 1
229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
125000005633 phthalidyl group Chemical group 0.000 abstract 1
125000006000 trichloroethyl group Chemical group 0.000 abstract 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 28
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
238000012746 preparative thin layer chromatography Methods 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000003921 oil Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
229940089960 chloroacetate Drugs 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000002253 acid Substances 0.000 description 2
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
UMSCEBMQKDMQLP-UHFFFAOYSA-N diethyl 3-sulfanylpent-2-enedioate Chemical compound CCOC(=O)CC(S)=CC(=O)OCC UMSCEBMQKDMQLP-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000005055 short column chromatography Methods 0.000 description 2
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
229940001584 sodium metabisulfite Drugs 0.000 description 2
235000010262 sodium metabisulphite Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000002211 ultraviolet spectrum Methods 0.000 description 2
NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 description 1
LLYSCVDKLKLODX-UHFFFAOYSA-N 3-acetyloxy-2-oxopropanoic acid Chemical compound CC(=O)OCC(=O)C(O)=O LLYSCVDKLKLODX-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
101100063435 Caenorhabditis elegans din-1 gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
102100034741 Cyclin-dependent kinase 20 Human genes 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
101500014379 Lymnaea stagnalis Ovulation hormone Proteins 0.000 description 1
ZTCLCSCHTACERP-AWEZNQCLSA-N N-[(1S)-1-[3-chloro-5-fluoro-2-[[2-methyl-4-(2-methyl-1,2,4-triazol-3-yl)quinolin-8-yl]oxymethyl]phenyl]ethyl]-2-(difluoromethoxy)acetamide Chemical compound C1=C(C=C(C(=C1Cl)COC1=CC=CC2=C(C=3N(N=CN=3)C)C=C(C)N=C12)[C@@H](NC(=O)COC(F)F)C)F ZTCLCSCHTACERP-AWEZNQCLSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
XNBOQYBVLZISAO-UHFFFAOYSA-N acetyloxymethyl 3-(2-ethoxy-2-oxoethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound CC(=O)OCOC(=O)C1C(=CC(=O)OCC)SC2CC(=O)N21 XNBOQYBVLZISAO-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
229960000723 ampicillin Drugs 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000006364 carbonyl oxy methylene group Chemical group [H]C([H])([*:2])OC([*:1])=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
PNBLXAHSDJEAME-UHFFFAOYSA-N ethyl 5-hydroxy-3-sulfanylpent-2-enoate Chemical compound SC(=CC(=O)OCC)CCO PNBLXAHSDJEAME-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
VYHPOMLHQAZVEG-SECBINFHSA-N methyl (5R)-3-(2-acetyloxyethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound C(C)(=O)OCCC=1S[C@H]2N(C=1C(=O)OC)C(C2)=O VYHPOMLHQAZVEG-SECBINFHSA-N 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
KWUZCAVKPCRJPO-UHFFFAOYSA-N n-ethyl-4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound C1=CC(NCC)=CC=C1C1=NC2=CC=C(C)C=C2S1 KWUZCAVKPCRJPO-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 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
- C07D499/88—Compounds with a double bond between positions 2 and 3 and 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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)
Veterinary Medicine (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Cephalosporin Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CS802289A 1979-04-06 1980-04-02 Method of making the inhibitor of the beta-lactamase CS219273B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7912168		1979-04-06

Publications (1)

Publication Number	Publication Date
CS219273B2 true CS219273B2 (en)	1983-03-25

Family

ID=10504396

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS802289A CS219273B2 (en)	1979-04-06	1980-04-02	Method of making the inhibitor of the beta-lactamase

Country Status (24)

Country	Link
US (1)	US4269771A (fr)
JP (1)	JPS55139385A (fr)
AT (1)	AT369371B (fr)
AU (1)	AU536673B2 (fr)
BE (1)	BE882621A (fr)
CA (1)	CA1148143A (fr)
CH (1)	CH645645A5 (fr)
CS (1)	CS219273B2 (fr)
DE (1)	DE3012975A1 (fr)
DK (1)	DK144180A (fr)
FI (1)	FI801080A (fr)
FR (1)	FR2453162A1 (fr)
GB (1)	GB2048857B (fr)
GR (1)	GR66673B (fr)
HU (1)	HU182118B (fr)
IE (1)	IE49656B1 (fr)
IL (1)	IL59760A (fr)
IT (1)	IT1196407B (fr)
LU (1)	LU82320A1 (fr)
NL (1)	NL8001919A (fr)
SE (1)	SE8002600L (fr)
SU (1)	SU1152524A3 (fr)
YU (1)	YU93880A (fr)
ZA (1)	ZA802000B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4500457A (en) *	1977-05-09	1985-02-19	Ciba-Geigy Corporation	Process for preparing thia-aza compounds with a beta-lactam ring
US4331677A (en) *	1978-11-24	1982-05-25	Farmitalia Carlo Erba S.P.A.	7-Oxo-4-1-aza-bicyclo-[3,2,0]-heptane derivatives
JPS5625110A (en) *	1978-12-18	1981-03-10	Bristol Myers Co	Antibacterial
US4347183A (en) *	1981-02-02	1982-08-31	Schering Corporation	Process for the synthesis of penems and carbapenems
AT379399B (de) *	1981-12-11	1985-12-27	Erba Farmitalia	Verfahren zur herstellung von optisch aktiven penemen
NO831160L (no) *	1982-04-08	1983-10-10	Erba Farmitalia	Fremstilling av substituerte penem-derivater
GB8321677D0 (en) *	1983-08-11	1983-09-14	Erba Farmitalia	Preparation of penems
US6720445B2 (en)	2000-12-21	2004-04-13	Beacon Laboratories, Inc.	Acetyloxymethyl esters and methods for using the same

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3905965A (en) *	1969-10-17	1975-09-16	Roussel Uclaf	Process of total synthesis of cephalosporin derivatives and intermediates
US4053468A (en) *	1976-02-25	1977-10-11	Smithkline Corporation	Process for preparing 7-oxo cephalosporins and 6-oxo penicillins
LU77306A1 (fr) *	1977-05-09	1979-01-18
EP0000636A1 (fr) *	1977-07-13	1979-02-07	Glaxo Group Limited	Composés dérivés pénème, procédés pour leur préparation, leur utilisation dans les compositions pharmaceutiques et les azétidinones utilisées dans leur préparation
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
JPS54117459A (en) *	1978-01-20	1979-09-12	Glaxo Group Ltd	Novel lactam compound
GB2014574A (en) *	1978-02-16	1979-08-30	Glaxo Group Ltd	Lactam Compounds
EP0010358A1 (fr) *	1978-09-20	1980-04-30	Glaxo Group Limited	Composés de bêta-lactame, procédés pour leur préparation, compositions les contenant, intermédiaires utilisables dans leur préparation et méthodes pour leur production

1979
- 1979-11-13 US US06/093,603 patent/US4269771A/en not_active Expired - Lifetime
1980
- 1980-04-01 NL NL8001919A patent/NL8001919A/nl not_active Application Discontinuation
- 1980-04-01 AT AT0177480A patent/AT369371B/de not_active IP Right Cessation
- 1980-04-01 LU LU82320A patent/LU82320A1/fr unknown
- 1980-04-01 IT IT21099/80A patent/IT1196407B/it active
- 1980-04-01 GB GB8010920A patent/GB2048857B/en not_active Expired
- 1980-04-01 AU AU57015/80A patent/AU536673B2/en not_active Ceased
- 1980-04-02 DK DK144180A patent/DK144180A/da not_active Application Discontinuation
- 1980-04-02 DE DE19803012975 patent/DE3012975A1/de not_active Withdrawn
- 1980-04-02 CH CH261580A patent/CH645645A5/de not_active IP Right Cessation
- 1980-04-02 IE IE668/80A patent/IE49656B1/en unknown
- 1980-04-02 GR GR61611A patent/GR66673B/el unknown
- 1980-04-02 JP JP4403280A patent/JPS55139385A/ja active Pending
- 1980-04-02 CS CS802289A patent/CS219273B2/cs unknown
- 1980-04-02 CA CA000349137A patent/CA1148143A/fr not_active Expired
- 1980-04-03 FI FI801080A patent/FI801080A/fi not_active Application Discontinuation
- 1980-04-03 SE SE8002600A patent/SE8002600L/xx not_active Application Discontinuation
- 1980-04-03 IL IL59760A patent/IL59760A/xx unknown
- 1980-04-03 ZA ZA00802000A patent/ZA802000B/xx unknown
- 1980-04-03 BE BE0/200106A patent/BE882621A/fr not_active IP Right Cessation
- 1980-04-03 HU HU80810A patent/HU182118B/hu unknown
- 1980-04-04 SU SU802903400A patent/SU1152524A3/ru active
- 1980-04-04 FR FR8007730A patent/FR2453162A1/fr active Pending
- 1980-04-04 YU YU00938/80A patent/YU93880A/xx unknown

Also Published As

Publication number	Publication date
DK144180A (da)	1980-10-07
DE3012975A1 (de)	1980-10-23
GR66673B (fr)	1981-04-08
YU93880A (en)	1983-02-28
BE882621A (fr)	1980-10-03
FR2453162A1 (fr)	1980-10-31
CA1148143A (fr)	1983-06-14
ZA802000B (en)	1981-04-29
US4269771A (en)	1981-05-26
SU1152524A3 (en)	1985-04-23
CH645645A5 (de)	1984-10-15
IT8021099A0 (it)	1980-04-01
GB2048857B (en)	1983-05-25
IE800668L (en)	1980-10-06
FI801080A (fi)	1980-10-07
IE49656B1 (en)	1985-11-13
SE8002600L (sv)	1980-10-07
AU536673B2 (en)	1984-05-17
LU82320A1 (fr)	1980-07-02
HU182118B (en)	1983-12-28
IL59760A (en)	1983-07-31
AT369371B (de)	1982-12-27
GB2048857A (en)	1980-12-17
IL59760A0 (en)	1980-06-30
IT1196407B (it)	1988-11-16
ATA177480A (de)	1982-05-15
JPS55139385A (en)	1980-10-31
AU5701580A (en)	1980-10-09
NL8001919A (nl)	1980-10-08

Publication	Publication Date	Title
Burgess et al.	1991	Optically active building blocks from the SPAC reaction: a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone, a statine analog
Franco et al.	1982	Novel syntheses of 5-aroyl-1, 2-dihydro-3H-pyrrolo [1, 2-a] pyrrole-1-carboxylic acids
Šmit et al.	2015	Three-step synthetic pathway to fused bicyclic hydantoins involving a selenocyclization step
Andreoli et al.	1991	. beta.-Lactams from ester enolates and silylimines: enantioselective synthesis of the trans-carbapenem antibiotics (+)-PS-5 and (+)-PS-6
CS219273B2 (en)	1983-03-25	Method of making the inhibitor of the beta-lactamase
FI82697C (fi)	1991-04-10	Foerfarande foer framstaellning av farmaceutiskt vaerdefulla tautomera tioner.
Musser et al.	1982	Cytochalasin support studies. The C14-C19 subunit of cytochalasin C. Intramolecular 2+ 2 photochemical cycloaddition of vinyl sulfones
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Yuste et al.	1982	4-Hydroxy-2-butenolide. A versatile reagent for the synthesis of heterocyclic compounds
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Huang et al.	2003	Synthesis of (S)-vasicol and (S)-3-hydroxy-2-pyrrolidinone
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Hernandez et al.	1994	Syntheses of Substituted Succinimides by Radical. beta.-Fragmentation of Bicyclic Carbinol Amides. A New Expeditious Synthesis of 2-[2-(Methoxycarbonyl) ethyl]-3-[(methoxycarbonyl) methyl]-3-methylsuccinimide, the Ring-B Imide of Vitamin B12
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Lepage et al.	2018	Stereoselective bidirectional synthesis of spiroacetals via Rh (II)-catalysed double C–H insertion
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