NL8003596A - 6-amino-spiro- (penam 2,4'-piperidine)-3-carbonzuur- derivaten de bereiding daarvan, alsmede farmaceutische preparaten die deze verbindingen als actieve component bevatten. - Google Patents

6-amino-spiro- (penam 2,4'-piperidine)-3-carbonzuur- derivaten de bereiding daarvan, alsmede farmaceutische preparaten die deze verbindingen als actieve component bevatten. Download PDF

Info

Publication number: NL8003596A
Authority: NL; Netherlands
Prior art keywords: spiro; penam; piperidine; amino; carboxylic acid
Prior art date: 1979-06-25

Application number

NL8003596A

Other languages

English (en)

Dutch (nl)

Original Assignee

Ucb Sa

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.)

1979-06-25

Filing date

1980-06-20

Publication date

1980-12-30

1980-06-20 Application filed by Ucb Sa filed Critical Ucb Sa

1980-12-30 Publication of NL8003596A publication Critical patent/NL8003596A/nl

Links

150000001875 compounds Chemical class 0.000 title claims description 48
238000002360 preparation method Methods 0.000 title claims description 19
239000000825 pharmaceutical preparation Substances 0.000 title description 2
PPJZWRJVKDRLHT-QFSRMBNQSA-N NC1[C@@H]2N(CC3(CCNCC3)S2)C1=O Chemical compound NC1[C@@H]2N(CC3(CCNCC3)S2)C1=O PPJZWRJVKDRLHT-QFSRMBNQSA-N 0.000 title 1
-1 2-phenylacetyl Chemical group 0.000 claims description 77
229930182555 Penicillin Natural products 0.000 claims description 26
150000002960 penicillins Chemical class 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
241000894006 Bacteria Species 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
WSHJJCPTKWSMRR-RXMQYKEDSA-N penam Chemical compound S1CCN2C(=O)C[C@H]21 WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
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241001522878 Escherichia coli B Species 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
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AIPVTTKYSPOWFO-UHFFFAOYSA-N azepane-1-carbaldehyde Chemical class O=CN1CCCCCC1 AIPVTTKYSPOWFO-UHFFFAOYSA-N 0.000 description 2
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239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 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
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000008261 resistance mechanism Effects 0.000 description 1
230000001932 seasonal effect Effects 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
208000013223 septicemia Diseases 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-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
- 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

Landscapes

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

NL8003596A 1979-06-25 1980-06-20 6-amino-spiro- (penam 2,4'-piperidine)-3-carbonzuur- derivaten de bereiding daarvan, alsmede farmaceutische preparaten die deze verbindingen als actieve component bevatten. NL8003596A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7922055		1979-06-25
GB7922055		1979-06-25

Publications (1)

Publication Number	Publication Date
NL8003596A true NL8003596A (nl)	1980-12-30

Family

ID=10506074

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8003596A NL8003596A (nl)	1979-06-25	1980-06-20	6-amino-spiro- (penam 2,4'-piperidine)-3-carbonzuur- derivaten de bereiding daarvan, alsmede farmaceutische preparaten die deze verbindingen als actieve component bevatten.

Country Status (10)

Country	Link
US (1)	US4271173A (fr)
JP (1)	JPS567789A (fr)
BE (1)	BE883970A (fr)
CA (1)	CA1148144A (fr)
DE (1)	DE3023831A1 (fr)
FR (1)	FR2459801A1 (fr)
GB (1)	GB2052496B (fr)
IT (1)	IT1145338B (fr)
NL (1)	NL8003596A (fr)
SU (1)	SU997609A3 (fr)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1576415A (en) *	1976-05-25	1980-10-08	Ucb Sa	Penam-carboxylic acids
GB1576414A (en) *	1976-05-25	1980-10-08	Ucb Sa	Anti-bacterially-active penicillins
GB1567561A (en) *	1977-01-18	1980-05-14	Ucb Sa	Amino-spiro(oxa-(orthia)cycloalkane-penam) - carboxylic acids
GB1567562A (en) *	1977-01-18	1980-05-14	Ucb Sa	Amino-spiro(oxy(or thia) cycloalkane - penam) - carboxylicacid derivatives

1980
- 1980-05-30 GB GB8017713A patent/GB2052496B/en not_active Expired
- 1980-06-20 NL NL8003596A patent/NL8003596A/nl not_active Application Discontinuation
- 1980-06-23 CA CA000354562A patent/CA1148144A/fr not_active Expired
- 1980-06-23 FR FR8013930A patent/FR2459801A1/fr active Granted
- 1980-06-24 BE BE1/9861A patent/BE883970A/fr not_active IP Right Cessation
- 1980-06-24 SU SU802936854A patent/SU997609A3/ru active
- 1980-06-24 JP JP8581680A patent/JPS567789A/ja active Pending
- 1980-06-24 US US06/162,615 patent/US4271173A/en not_active Expired - Lifetime
- 1980-06-24 IT IT49052/80A patent/IT1145338B/it active
- 1980-06-25 DE DE19803023831 patent/DE3023831A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
FR2459801B1 (fr)	1983-04-22
IT8049052A0 (it)	1980-06-24
CA1148144A (fr)	1983-06-14
SU997609A3 (ru)	1983-02-15
GB2052496A (en)	1981-01-28
IT1145338B (it)	1986-11-05
US4271173A (en)	1981-06-02
JPS567789A (en)	1981-01-27
GB2052496B (en)	1983-06-29
FR2459801A1 (fr)	1981-01-16
BE883970A (fr)	1980-12-24
DE3023831A1 (de)	1981-01-22

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-08-03	BV	The patent application has lapsed

Publication	Publication Date	Title
US7812014B2 (en)	2010-10-12	Bicyclic 6-alkylidene-penems as β-lactamase inhibitors
EP0199446B1 (fr)	1990-06-13	Dérivés de pénème, leur préparation et application
US20060276445A1 (en)	2006-12-07	Bicyclic 6-alkylidene-penems as class-D beta-lactamases inhibitors
US4952577A (en)	1990-08-28	Methoxymethyl penem compounds
EP0318767A2 (fr)	1989-06-07	Esters d'acides carboxyliques pharmacologiquement actifs, clivables sous conditions physiologiques
DE69625910T2 (de)	2003-11-06	Penamsulfone als beta-laktamase inhibitoren
JPS63162694A (ja)	1988-07-06	ペネム誘導体、その製造法およびその用途
JPH05508625A (ja)	1993-12-02	新規なセファロスポリン化合物およびその製法
DD247677A5 (de)	1987-07-15	Verfahren zur herstellung von 6-(subst.)-methylenpenicillan- und 6-(subst.)-hydroxymehtylpenicillansaeure und deren derivaten
AU760249B2 (en)	2003-05-08	Novel c-2 s/o- and s/n formaldehyde acetal derivatives of carbapenem-3-carboxylic acids and their use as antibiotics and beta-lactamase inhibitors
CA1148144A (fr)	1983-06-14	Derives d'acide 6-amino-spiro¬penam-2,4'- piperidine\|-3-carboxylique
DE3688066T2 (de)	1993-07-22	1-carbacephalosporin-antibiotika.
US4416883A (en)	1983-11-22	Penicillin derivatives
US4540580A (en)	1985-09-10	2-[(1'R)-1'-Aminoalkyl]penems
US4540579A (en)	1985-09-10	2-[(R) Amino acid alkyl]penems
US3767645A (en)	1973-10-23	Acylthioacetyl penicillins
US4349551A (en)	1982-09-14	Penicillin derivatives and compositions containing them
DK162286B (da)	1991-10-07	Penemderivat, farmaceutisk praeparat indeholdende dette, anvendelse af derivatet samt fremgangsmaader til fremstilling deraf
NL8003597A (nl)	1980-12-30	6-amino-spiro (penam-2,4'-piperidine)-3-carbonzuren, de bereiding daarvan, alsmede farmaceutische preparaten die deze verbindingen als actieve component bevatten.
DE2253781A1 (de)	1973-05-24	Keteniminpenicilline
GB1576414A (en)	1980-10-08	Anti-bacterially-active penicillins
US4394375A (en)	1983-07-19	Cephalosporin derivatives, and compositions containing them
GB1567562A (en)	1980-05-14	Amino-spiro(oxy(or thia) cycloalkane - penam) - carboxylicacid derivatives
US3879385A (en)	1975-04-22	3-(Alpha-trifluoromethylarylacetamido)-1,4-cyclo(1,-carboxyl)alkylenethio)-azetidin-2-one derivatives
IT202000031070A1 (it)	2022-06-16	Procedimento di sintesi di derivati ammidici dell’acido 8-idrossi penicillanico