PT85773B - Processo para a preparacao de um hidrato estavel de um derivado de penicilina com actividade antimicrobiana contra microrganismos gram-positivos e gram- -negativos - Google Patents
Processo para a preparacao de um hidrato estavel de um derivado de penicilina com actividade antimicrobiana contra microrganismos gram-positivos e gram- -negativos Download PDFInfo
- Publication number
- PT85773B PT85773B PT85773A PT8577387A PT85773B PT 85773 B PT85773 B PT 85773B PT 85773 A PT85773 A PT 85773A PT 8577387 A PT8577387 A PT 8577387A PT 85773 B PT85773 B PT 85773B
- Authority
- PT
- Portugal
- Prior art keywords
- gram
- methyl
- trihydrate
- solution
- asparaginylamoxicillin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 150000002960 penicillins Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 244000005700 microbiome Species 0.000 title claims description 5
- 230000000845 anti-microbial effect Effects 0.000 title claims description 4
- 150000004684 trihydrates Chemical class 0.000 claims abstract description 14
- 239000000243 solution Substances 0.000 claims description 19
- -1 (2R) -2-amino-3- (N-methyl-carbamoyl) propionamido Chemical group 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 3
- NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- ATPVSNJCPGPJGO-XUXOXWKISA-N 6-[[(1s)-2-[[(2s)-4-amino-2-(methylamino)-4-oxobutanoyl]amino]-1-(4-hydroxyphenyl)-2-oxoethyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H](NC2C(N3C(C(C)(C)SC32)C(O)=O)=O)C(=O)NC(=O)[C@H](CC(N)=O)NC)=CC=C(O)C=C1 ATPVSNJCPGPJGO-XUXOXWKISA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 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
- 238000012360 testing method Methods 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin 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=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 2
- 229960003022 amoxicillin Drugs 0.000 description 2
- 229960004920 amoxicillin trihydrate Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 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 1
- 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 1
- 238000001159 Fisher's combined probability test Methods 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
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Natural products NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- 125000002059 L-arginyl group Chemical class O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 description 1
- 125000002066 L-histidyl group Chemical class [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- FGDQGIKMWOAFIK-UHFFFAOYSA-N acetonitrile;phosphoric acid Chemical compound CC#N.OP(O)(O)=O FGDQGIKMWOAFIK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000011141 high resolution liquid chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- UVUKMPQRNIREDM-UHFFFAOYSA-N n,n-dibenzoylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C(=O)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 UVUKMPQRNIREDM-UHFFFAOYSA-N 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product 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
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- C07D499/04—Preparation
- C07D499/18—Separation; Purification
-
- 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
- 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
- C07D499/21—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 with a nitrogen atom directly attached in position 6 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
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
- C07D499/68—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with aromatic rings as additional substituents on the carbon chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61226423A JPS6379888A (ja) | 1986-09-24 | 1986-09-24 | ペニシリン誘導体の安定型水和物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT85773A PT85773A (en) | 1987-10-01 |
| PT85773B true PT85773B (pt) | 1990-07-31 |
Family
ID=16844890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT85773A PT85773B (pt) | 1986-09-24 | 1987-09-23 | Processo para a preparacao de um hidrato estavel de um derivado de penicilina com actividade antimicrobiana contra microrganismos gram-positivos e gram- -negativos |
Country Status (24)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5375123A (en) * | 1993-02-05 | 1994-12-20 | Telefonakitebolaget L. M. Ericsson | Allocation of channels using interference estimation |
| US6473602B1 (en) | 1996-10-28 | 2002-10-29 | Ericsson Inc. | Mobile assisted handoff in radiocommunication systems |
| PE20000879A1 (es) * | 1998-04-29 | 2000-09-23 | Dsm Nv | METODO PARA CRISTALIZAR UN ANTIBIOTICO ß-LACTAMICO |
| KR101879756B1 (ko) * | 2016-11-30 | 2018-08-17 | 주식회사 지앤지비 | 욕실용 난방기 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6705789A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1967-03-08 | 1968-09-09 | ||
| GB1241844A (en) * | 1968-08-23 | 1971-08-04 | Beecham Group Ltd | Penicillins |
| US4053609A (en) * | 1975-09-12 | 1977-10-11 | Tanabe Seiyaku Co., Ltd. | Penicillins and processes for preparing the same |
| JPS5640686A (en) * | 1979-09-11 | 1981-04-16 | Tanabe Seiyaku Co Ltd | Purification of penicillin derivative |
-
1986
- 1986-09-24 JP JP61226423A patent/JPS6379888A/ja active Granted
-
1987
- 1987-09-01 IE IE234687A patent/IE60042B1/en not_active IP Right Cessation
- 1987-09-03 EP EP87307794A patent/EP0261823B1/en not_active Expired - Lifetime
- 1987-09-03 ES ES198787307794T patent/ES2026545T3/es not_active Expired - Lifetime
- 1987-09-03 AT AT87307794T patent/ATE59655T1/de not_active IP Right Cessation
- 1987-09-03 DE DE8787307794T patent/DE3766921D1/de not_active Expired - Lifetime
- 1987-09-04 IL IL83786A patent/IL83786A/xx not_active IP Right Cessation
- 1987-09-09 ZA ZA876739A patent/ZA876739B/xx unknown
- 1987-09-11 PH PH35805A patent/PH23644A/en unknown
- 1987-09-12 CN CN87106308A patent/CN1021225C/zh not_active Expired - Fee Related
- 1987-09-18 US US07/098,364 patent/US4866170A/en not_active Expired - Fee Related
- 1987-09-22 AU AU78827/87A patent/AU592467B2/en not_active Ceased
- 1987-09-22 MY MYPI87001873A patent/MY102553A/en unknown
- 1987-09-23 PT PT85773A patent/PT85773B/pt not_active IP Right Cessation
- 1987-09-23 CA CA000547616A patent/CA1286285C/en not_active Expired - Lifetime
- 1987-09-23 SU SU874203390A patent/SU1517764A3/ru active
- 1987-09-23 HU HU874281A patent/HU196810B/hu not_active IP Right Cessation
- 1987-09-23 DK DK500887A patent/DK167319B1/da not_active IP Right Cessation
- 1987-09-23 FI FI874152A patent/FI86853C/fi not_active IP Right Cessation
- 1987-09-23 NO NO873969A patent/NO169717C/no not_active IP Right Cessation
- 1987-09-24 KR KR1019870010566A patent/KR920003902B1/ko not_active Expired
- 1987-10-15 AT AT0273187A patent/AT389311B/de not_active IP Right Cessation
-
1991
- 1991-01-03 GR GR90400968T patent/GR3001274T3/el unknown
-
1993
- 1993-02-11 SG SG153/93A patent/SG15393G/en unknown
- 1993-04-29 HK HK420/93A patent/HK42093A/en not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 20010731 |