CH404667A - Procédé de préparation d'un nouveau dérivé de la pénicilline - Google Patents

Procédé de préparation d'un nouveau dérivé de la pénicilline

Info

Publication number: CH404667A
Authority: CH; Switzerland
Prior art keywords: amino; acid; erythromycin; hexahydrobenzyl; propionyl
Prior art date: 1962-08-31

Application number

CH980763A

Other languages

English (en)

French (fr)

Inventor

Penasse Lucien

Nomine Gerard

Hagemann Guy

Barthelemy Pierre

Original Assignee

Roussel Uclaf

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.)

1962-08-31

Filing date

1963-08-08

Publication date

1965-12-31

1962-08-31 Priority claimed from FR908344A external-priority patent/FR1421232A/fr

1963-02-20 Priority claimed from FR925432A external-priority patent/FR1426078A/fr

1963-08-08 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1965-12-31 Publication of CH404667A publication Critical patent/CH404667A/fr

Links

238000000034 method Methods 0.000 title claims description 8
150000002960 penicillins Chemical class 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
-1 alkali metal salt Chemical class 0.000 claims description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
TYQXKHPOXXXCTP-CSLYCKPJSA-N erythromycin A 2'-propanoate Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)OC(=O)CC)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 TYQXKHPOXXXCTP-CSLYCKPJSA-N 0.000 claims description 13
229950001028 erythromycin propionate Drugs 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
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 claims description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 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 claims description 5
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
238000001556 precipitation Methods 0.000 claims description 4
159000000000 sodium salts Chemical class 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 2
230000020477 pH reduction Effects 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
AOQONNCNKUWWRI-UHFFFAOYSA-N cyclohexylmethyl carbonochloridate Chemical group ClC(=O)OCC1CCCCC1 AOQONNCNKUWWRI-UHFFFAOYSA-N 0.000 claims 2
239000003960 organic solvent Substances 0.000 claims 2
150000003512 tertiary amines Chemical class 0.000 claims 2
239000012467 final product Substances 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 6
241000295644 Staphylococcaceae Species 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
229940126062 Compound A Drugs 0.000 description 3
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229940049954 penicillin Drugs 0.000 description 3
238000003756 stirring Methods 0.000 description 3
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000000284 extract Substances 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
229940056360 penicillin g Drugs 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
230000002195 synergetic effect Effects 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
108010087702 Penicillinase Proteins 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
229960003276 erythromycin Drugs 0.000 description 1
230000002949 hemolytic effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229960003085 meticillin Drugs 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
235000020075 ouzo Nutrition 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
229950009506 penicillinase Drugs 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
201000003068 rheumatic fever Diseases 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000011282 treatment Methods 0.000 description 1
238000005406 washing Methods 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

Landscapes

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

CH980763A 1962-08-31 1963-08-08 Procédé de préparation d'un nouveau dérivé de la pénicilline CH404667A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR908344A FR1421232A (fr)	1962-08-31	1962-08-31	Nouveaux dérivés de la pénicilline et procédé de préparation
FR925432A FR1426078A (fr)	1963-02-20	1963-02-20	Nouveau dérivé de la pénicilline et procédé de préparation

Publications (1)

Publication Number	Publication Date
CH404667A true CH404667A (fr)	1965-12-31

Family

ID=26197345

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH980763A CH404667A (fr)	1962-08-31	1963-08-08	Procédé de préparation d'un nouveau dérivé de la pénicilline

Country Status (6)

Country	Link
AT (1)	AT243436B (de)
CH (1)	CH404667A (de)
DE (1)	DE1203274B (de)
ES (1)	ES290113A1 (de)
GB (1)	GB1001784A (de)
NL (1)	NL137035C (de)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE569728A (de) *
DE953974C (de) *	1953-07-23	1956-12-13	Upjohn Co	Verfahren zur Herstellung saurer Dicarbonsaeureester des Erythromycins
CH332653A (de) *	1953-08-03	1958-09-15	Lilly Co Eli	Verfahren zur Herstellung von Säure-Additionssalzen des Erythromycins
DE1114498B (de) *	1958-08-02	1961-10-05	Lilly Co Eli	Verfahren zur Herstellung von Erythromicinestern und deren Salzen
FR1268464A (fr) *	1959-07-01	1961-08-04	Lilly Co Eli	Procédé de préparation de sulfates de dérivés de l'érythromycine

1963
- 1963-07-19 ES ES290113A patent/ES290113A1/es not_active Expired
- 1963-08-08 CH CH980763A patent/CH404667A/fr unknown
- 1963-08-28 AT AT692363A patent/AT243436B/de active
- 1963-08-29 DE DER36012A patent/DE1203274B/de active Pending
- 1963-08-29 GB GB34236/63A patent/GB1001784A/en not_active Expired
- 1963-08-30 NL NL297305A patent/NL137035C/xx active

Also Published As

Publication number	Publication date
GB1001784A (en)	1965-08-18
ES290113A1 (es)	1963-11-01
NL137035C (nl)	1973-03-15
AT243436B (de)	1965-11-10
DE1203274B (de)	1965-10-21

Publication	Publication Date	Title
JPS6237037B2 (de)	1987-08-10
FR2634766A1 (fr)	1990-02-02	Acides (rs)-2-(2,3-dihydro-5-hydroxy-4,6,7-trimethylbenzofurannyl)-acetiques, et acides 2-(2,3-dihydro-5-acyloxy-4,6,7-trimethylbenzofurannyl)-acetiques et leurs esters, utiles comme medicaments mucoregulateurs et anti-ischemiques, procede pour leur preparation et compositions pharmaceutiques les contenant
CH404667A (fr)	1965-12-31	Procédé de préparation d'un nouveau dérivé de la pénicilline
CA1123824A (fr)	1982-05-18	Oximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments
CH637650A5 (fr)	1983-08-15	Procede de preparation d'un acide chromone carboxylique.
CA1060020A (fr)	1979-08-07	Procede de preparation de nouveaux derives de la dibenzo/b,c/ thiepine et leurs sels
US3005854A (en)	1961-10-24	Process of producing dl-threo-l-phenyl-2-nitro propane-1, 3-diol
CH404649A (fr)	1965-12-31	Procédé de préparation d'un nouveau dérivé colchicique
Huggins et al.	1942	Studies on Substituted Diphenylbutadienes. I. The Addition of Bromine to 1-p-Bromophenyl-4-phenyl-1, 3-butadiene
CH408953A (fr)	1966-03-15	Procédé de préparation de nouveaux carbazates substitués
US3161649A (en)	1964-12-15	Substituted benzoxazoles
CH426858A (fr)	1966-12-31	Procédé de préparation de nouveaux dérivés colchiciques
CH407161A (fr)	1966-02-15	Procédé de préparation de nouveaux dérivés de l'acétanilide
CH433308A (fr)	1967-04-15	Procédé de préparation d'un nouveau dérivé de la quinoléine
FR2509730A1 (fr)	1983-01-21	Nouveaux phenols o-halogenes et o-substitues par un heterocycle, leur procede de preparation, medicaments les contenant, notamment anti-hypertenseurs, et nouveaux intermediaires de synthese
FR2534583A1 (fr)	1984-04-20	Procede pour la fabrication d'hexahydro-5-hydroxy-4-hydroxymethyl-2h-cyclopenta-(b)-furanne-2-one
FR2533927A1 (fr)	1984-04-06	Nouveaux aminoglucosides, leur preparation et leur utilisation comme medicaments
CH412897A (fr)	1966-05-15	Procédé de préparation d'amino oxazolinones
CH534677A (fr)	1973-03-15	Procédé de préparation d'acides bis-chromone-carboxyliques
CH293430A (fr)	1953-09-30	Procédé de préparation d'un nouveau dérivé d'oxazoline.
BE718270A (de)	1969-01-20
CH284723A (fr)	1952-07-31	Procédé de préparation d'un acylamidodiol aromatique, nitré dans le noyau.
CH592093A5 (en)	1977-10-14	7H-Indolizino (5,6,7-i,j)-isoquinolines - as antibilharzial, anthelmintic and antimicrobial agents
BE699167A (de)	1967-11-03
CH427801A (fr)	1967-01-15	Procédé de préparation de dérivés du succinimide