NL8002087A - Werkwijze voor de bereiding van 6-beta-amidino- penicillaanzuur-derivaten. - Google Patents

Werkwijze voor de bereiding van 6-beta-amidino- penicillaanzuur-derivaten. Download PDF

Info

Publication number: NL8002087A
Authority: NL; Netherlands
Prior art keywords: formula; carbon atoms; hydrogen atom; group; atoms
Prior art date: 1979-04-12

Application number

NL8002087A

Other languages

English (en)

Dutch (nl)

Original Assignee

Archifar Lab Chim Farm

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.)

1979-04-12

Filing date

1980-04-09

Publication date

1980-10-14

1980-04-09 Application filed by Archifar Lab Chim Farm filed Critical Archifar Lab Chim Farm

1980-10-14 Publication of NL8002087A publication Critical patent/NL8002087A/nl

Links

238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 8
150000001408 amides Chemical class 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 11
-1 acid amide halides Chemical class 0.000 description 7
239000000047 product Substances 0.000 description 7
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 6
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
150000008050 dialkyl sulfates Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000012265 solid product Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 2
AIPVTTKYSPOWFO-UHFFFAOYSA-N azepane-1-carbaldehyde Chemical compound O=CN1CCCCCC1 AIPVTTKYSPOWFO-UHFFFAOYSA-N 0.000 description 2
239000003782 beta lactam antibiotic agent Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000012467 final product Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229940024554 amdinocillin Drugs 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
BWWVAEOLVKTZFQ-ISVUSNJMSA-N chembl530 Chemical compound N(/[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)=C\N1CCCCCC1 BWWVAEOLVKTZFQ-ISVUSNJMSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
DWCZIOOZPIDHAB-UHFFFAOYSA-L methyl green Chemical compound [Cl-].[Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)[N+](C)(C)C)=C1C=CC(=[N+](C)C)C=C1 DWCZIOOZPIDHAB-UHFFFAOYSA-L 0.000 description 1
244000005700 microbiome Species 0.000 description 1
AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)

NL8002087A 1979-04-12 1980-04-09 Werkwijze voor de bereiding van 6-beta-amidino- penicillaanzuur-derivaten. NL8002087A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT21809/79A IT1119716B (it)	1979-04-12	1979-04-12	Metodo per la produzione di derivati dell'acido 6-beta-amidino-penicillanico
IT2180979		1979-04-12

Publications (1)

Publication Number	Publication Date
NL8002087A true NL8002087A (nl)	1980-10-14

Family

ID=11187143

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8002087A NL8002087A (nl)	1979-04-12	1980-04-09	Werkwijze voor de bereiding van 6-beta-amidino- penicillaanzuur-derivaten.

Country Status (10)

Country	Link
US (1)	US4278792A (it)
JP (1)	JPS55139386A (it)
BE (1)	BE882555A (it)
DE (1)	DE3012667A1 (it)
DK (1)	DK154880A (it)
ES (1)	ES8102575A1 (it)
FR (1)	FR2453864A1 (it)
GB (1)	GB2047243B (it)
IT (1)	IT1119716B (it)
NL (1)	NL8002087A (it)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
LU77362A1 (it) *	1977-05-17	1979-01-19
US5162523A (en) *	1989-07-21	1992-11-10	Hoffmann-La Roche Inc.	Cephalosporin antibacterial compounds
US5159077A (en) *	1989-07-21	1992-10-27	Hoffmann-La Roche Inc.	Penam antibacterial compounds
CN114573603A (zh) *	2022-03-07	2022-06-03	南京美智德合成材料有限公司	一种一锅合成匹美西林的工艺

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3957764A (en) *	1969-11-11	1976-05-18	Lovens Kemiske Fabrik Produktionsaktieselskab	6-aminopenicillanic acid derivatives

1979
- 1979-04-12 IT IT21809/79A patent/IT1119716B/it active
1980
- 1980-03-19 GB GB8009288A patent/GB2047243B/en not_active Expired
- 1980-03-24 US US06/132,763 patent/US4278792A/en not_active Expired - Lifetime
- 1980-03-28 FR FR8006993A patent/FR2453864A1/fr active Granted
- 1980-03-31 BE BE0/200055A patent/BE882555A/fr not_active IP Right Cessation
- 1980-04-01 DE DE19803012667 patent/DE3012667A1/de not_active Withdrawn
- 1980-04-01 JP JP4125480A patent/JPS55139386A/ja active Pending
- 1980-04-09 NL NL8002087A patent/NL8002087A/nl not_active Application Discontinuation
- 1980-04-10 DK DK154880A patent/DK154880A/da not_active Application Discontinuation
- 1980-04-11 ES ES490469A patent/ES8102575A1/es not_active Expired

Also Published As

Publication number	Publication date
US4278792A (en)	1981-07-14
ES490469A0 (es)	1981-02-16
DK154880A (da)	1980-10-13
GB2047243A (en)	1980-11-26
ES8102575A1 (es)	1981-02-16
JPS55139386A (en)	1980-10-31
IT7921809A0 (it)	1979-04-12
DE3012667A1 (de)	1980-10-23
IT1119716B (it)	1986-03-10
FR2453864B1 (it)	1983-05-27
BE882555A (fr)	1980-07-16
FR2453864A1 (fr)	1980-11-07
GB2047243B (en)	1983-06-15

Legal Events

Date	Code	Title	Description
1982-09-16	CNR	Transfer of rights (patent application after its laying open for public inspection)	Free format text: LEPETIT S.P.A. GRUPPO -
1984-12-03	BV	The patent application has lapsed

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US3936447A (en)	1976-02-03	7-Acylamino-desacetoxy-cephalosporanic acid esters and their production
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Rigo et al.	1988	Studies on pyrrolidinones. Synthesis of N‐acylpyroglutamic acids having bactericide and fungicide properties
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FI63759B (fi)	1983-04-29	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara bis-penicillanoyloxialkaner
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CS219347B2 (en)	1983-03-25	Method of preparation of the 1-hydroxyaporfin derivative
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