US3574185A - Acyl derivatives of erythromycin oxime - Google Patents
Acyl derivatives of erythromycin oxime Download PDFInfo
- Publication number
- US3574185A US3574185A US745104A US3574185DA US3574185A US 3574185 A US3574185 A US 3574185A US 745104 A US745104 A US 745104A US 3574185D A US3574185D A US 3574185DA US 3574185 A US3574185 A US 3574185A
- Authority
- US
- United States
- Prior art keywords
- erythromycin oxime
- percent
- millimols
- mono
- erythromycin
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Natural products 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 title description 8
- 125000002252 acyl group Chemical group 0.000 title description 5
- 229960003276 erythromycin Drugs 0.000 title description 5
- KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N\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 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 abstract description 41
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 229940088710 antibiotic agent Drugs 0.000 abstract description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- LOLKAJARZKDJTD-UHFFFAOYSA-N 4-Ethoxy-4-oxobutanoic acid Chemical compound CCOC(=O)CCC(O)=O LOLKAJARZKDJTD-UHFFFAOYSA-N 0.000 description 6
- 229940022682 acetone Drugs 0.000 description 5
- 150000001805 chlorine compounds Chemical class 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229940050390 benzoate Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UZNLHJCCGYKCIL-UHFFFAOYSA-N 6-ethoxy-6-oxohexanoic acid Chemical compound CCOC(=O)CCCCC(O)=O UZNLHJCCGYKCIL-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
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- -1 erythromycin oxime propionates Chemical class 0.000 description 3
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WZBCGBHVFQPVKQ-UHFFFAOYSA-N 4-ethoxy-4-oxobutanoic acid;hydrochloride Chemical compound Cl.CCOC(=O)CCC(O)=O WZBCGBHVFQPVKQ-UHFFFAOYSA-N 0.000 description 2
- KWWCXEXKKYYNRF-UHFFFAOYSA-N 4-methoxy-4-oxobutanoic acid;hydrochloride Chemical compound Cl.COC(=O)CCC(O)=O KWWCXEXKKYYNRF-UHFFFAOYSA-N 0.000 description 2
- FUFHKMOUERGVRB-UHFFFAOYSA-N 6-ethoxy-6-oxohexanoic acid;hydrochloride Chemical compound Cl.CCOC(=O)CCCCC(O)=O FUFHKMOUERGVRB-UHFFFAOYSA-N 0.000 description 2
- JVKJKTZQMQSICC-UHFFFAOYSA-N 6-methoxy-6-oxohexanoic acid;hydrochloride Chemical compound Cl.COC(=O)CCCCC(O)=O JVKJKTZQMQSICC-UHFFFAOYSA-N 0.000 description 2
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JDRMYOQETPMYQX-UHFFFAOYSA-M 4-methoxy-4-oxobutanoate Chemical compound COC(=O)CCC([O-])=O JDRMYOQETPMYQX-UHFFFAOYSA-M 0.000 description 1
- 241000194106 Bacillus mycoides Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- NGXUUAFYUCOICP-UHFFFAOYSA-N aminometradine Chemical group CCN1C(=O)C=C(N)N(CC=C)C1=O NGXUUAFYUCOICP-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- JDRMYOQETPMYQX-UHFFFAOYSA-N butanedioic acid monomethyl ester Natural products COC(=O)CCC(O)=O JDRMYOQETPMYQX-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000005646 oximino group Chemical group 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Definitions
- the present invention relates to acyl derivatives of erythromycin oxime and to the preparation thereof.
- acylation of erythrornycin with different acid chlorides or acid anhydrides yields a variety of products with a single acyl grouping attached to the hydroxyl group of the desosaminyl moiety.
- the sole exception is with the use of acetic anhydride as an acylating agent, which yield erythromycin diacetate.
- EXAMPLE 2 Erythromycin oxime mono-palmitate Erythromycin oxime mono-stearate From 5 g. (6.67 millimols) of erythromycin oxime, 2.616 g. (8.64 millimols) of stearoyl chloride and 2.5 g. of sodium bicarbonate, by the process described in Example 1, there are obtained 5.24 g. (77.49%) of mono-stearate, M.P. 74-78 C.
- EXAMPLE 4 Erythromycin oxime mono-benz oate From 5 g. (6.67 millimols) of erythromycin oxime, 1.26 g. (8.64 millimols) of benzoyl chloride and 2.5 g. of sodium carbonate, by the process described in Example 1, there are obtained 4.15 g. (73%) of monobenzoate, M.P. ISO-152 C.
- EXAMPLE 6 Erythromycin oxime mono-ethylsuccinate From 5 g. (6.67 millimols) of erythromycin oxime, 1.098 g. (6.67 millimols) of succinic acid ethylester chloride and 2.5 g. of sodium bicarbonate, by the process described in Example 1, there are obtained 4.23 g. (72.5%) of mono-ethylsuccinate, M.P. 99102. C.
- EXAMPLE 7 Erythromycin oxime mono-methyladipate From 5 g. (6.67 millimols) of erythromycin oxime, 1.19 g. (6.67 millimols) of adipic acid methylester chloride and 2.5 g. of sodium bicarbonate, by the process described in Example 1, there are obtained 4.5 g. (76%) of mono-methyladipate, M.P. 89-94 C.
- EXAMPLE 8 Erythromycin oxime mono-ethyladipate From 5 g. (6.67 millimols) of erythromycin oxime, 1.28 g. (6.67 millimols) of adipic acid mono-ethylester chloride and 2.5 g. of sodium bicarbonate, by the process described in Example 1, there are obtained 4.8 g. (79.3%) of mono-ethyladipate, M.P. 82-86 C.
- EXAMPLE 9 Erythromycin oxime bis-propionate To a suspension of 5 g. (6.67 millimols) of erythromycin oxime in ml. of dry acetone, 5.0 g. of dry sodium bicarbonate were added. Then the solution of 1.596 g. (17.29 millimols) of propionyl chloride in 50 ml. of dry acetone was added dropwise with stirring over a period of one hour. Stirring was continued for 8 hours more While heating the reaction mixture under reflux. After cooling to room temperature and filtration, the clear filtrate was diluted with a solution of 5 g. sodium bicarbonate in 250 ml. water and extracted with one 100 m1. and two 50 ml. portions of ether. The isolation of the product was performed in the same manner as described in Example 1. The yield was 4.49 g. (78.2%), M.P. 196-202 C.
- EXAMPLE 1O Erythromycin oxime bis-palmitate From 5 g. (6.67 millimols) of erythromycin oxime, 4.5 g. (16.38 millimols) of palmitoyl chloride and 5 g. of sodium bicarbonate, by the process described in Example 9, there are obtained 6.31 g. (77%) of bis-palmitate, M.P. 6872 C.
- EXAMPLE 11 Erythromycin oxime bis-stearate From 5 g. (6.67 millimols) of erythromycin oxime, 5 g. (16.52 millimols) of stearoyl chloride and 5 g. of sodium bicarbonate, by the process described in Example 9, there are obtained 6.2 g. (72.6%) of bis-stearate, M.P. 63.5-66.5 C.
- EXAMPLE 12 Erythromycin oxime bis-benzoate From 5 g. (6.67 millimols) of erythromycin oxime, 2.52 g. (17.28 millimols) of benzoyl chloride and 5 g. of sodium bicarbonate, by the process described in Example 9, there are obtained 4.75 g. (74%) of bis-benzoate, M.P. 193-196" C.
- EXAMPLE 13 Erythromycin oxime bis-methylsuccinate From 5 g. (6.67 millimols) of erythromycin oxime, 2.424 g. (16.1 millimols) of succinic acid methylester chloride, and 5 g. of sodium bicarbonate, by the process described in Example 9, there are obtained 5.18 g. (79.5%) of bis-methylsuccinate, M.P. 173176 C.
- EXAMPLE 14 Erythromycin oxime bis-ethylsuccinate From 5 g. (6.67 millimols) of erythromycin oxime, 2.649 g. (16.1 millimols) of succinic acid ethylester chloride and 5 g. of sodium in carbonate, by the process described in Example 9, there are obtained 4.92 g. (73.4%) of bis-ethylsuccinate, M.P. -162 C.
- EXAMPLE 15 Erythromycin oxime bis-methyladi'pate From g. (6.67 millirnols) of erythromycin oxime, 2.86 g. (16.1 millirnols) of adipic acid methylester chloride and 5 g. of sodium bicarbonate, by the process described in Example 9, there are obtained 5.25 g. (76.2%) of bis-methyladipate, M.P. 7883 C.
- EXAMPLE 16 Erythromycin oxime bis-ethyladipate From 5 g. (6.67 millirnols) of erythromycin oxime, 3.1 g. (16.1 millirnols) of adipic acid ethylester chloride and 5 g. of sodium bicarbonate, by the process described in Example 9, there are obtained 5.68 g. (80.1%) of hisethyiadipate, M.P. 72-76 C.
- Erythromycin oxime mono-stearate Erythromycin oxime mono-benzoate. Erythromycin oxime mono-methy1succinate.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU1540/67A YU31319B (en) | 1967-08-03 | 1967-08-03 | Postupak za dobijanje acil derivata eritromicin oksima |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3574185A true US3574185A (en) | 1971-04-06 |
Family
ID=25554577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US745104A Expired - Lifetime US3574185A (en) | 1967-08-03 | 1968-07-16 | Acyl derivatives of erythromycin oxime |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3574185A (ru) |
| AT (1) | AT278241B (ru) |
| CH (1) | CH503016A (ru) |
| CS (1) | CS151478B2 (ru) |
| FR (1) | FR1584610A (ru) |
| SU (1) | SU664568A3 (ru) |
| YU (1) | YU31319B (ru) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2121758A1 (ru) * | 1971-01-11 | 1972-08-25 | Abbott Lab | |
| US3855203A (en) * | 1973-05-03 | 1974-12-17 | Abbott Lab | 4{41 -o-sulfonyl erythromycin-9-o-oxime derivatives |
| US3869444A (en) * | 1972-10-10 | 1975-03-04 | Abbott Lab | Esters of erythromycin oxime |
| US4328334A (en) * | 1979-04-02 | 1982-05-04 | Pliva Pharmaceutical And Chemical Works | 11-Aza-10-deoxo-10-dihydroerythromycin A and derivatives thereof as well as a process for their preparation |
| US4526889A (en) * | 1982-11-15 | 1985-07-02 | Pfizer Inc. | Epimeric azahomoerythromycin A derivative, intermediates and method of use |
| US5075289A (en) * | 1988-06-07 | 1991-12-24 | Abbott Laboratories | 9-r-azacyclic erythromycin antibiotics |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2473525A1 (fr) * | 1980-01-11 | 1981-07-17 | Roussel Uclaf | Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments |
-
1967
- 1967-08-03 YU YU1540/67A patent/YU31319B/xx unknown
-
1968
- 1968-07-11 AT AT668968A patent/AT278241B/de not_active IP Right Cessation
- 1968-07-16 US US745104A patent/US3574185A/en not_active Expired - Lifetime
- 1968-07-31 SU SU681262024A patent/SU664568A3/ru active
- 1968-07-31 FR FR1584610D patent/FR1584610A/fr not_active Expired
- 1968-08-02 CH CH1165668A patent/CH503016A/de not_active IP Right Cessation
- 1968-08-02 CS CS5649A patent/CS151478B2/cs unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2121758A1 (ru) * | 1971-01-11 | 1972-08-25 | Abbott Lab | |
| US3869444A (en) * | 1972-10-10 | 1975-03-04 | Abbott Lab | Esters of erythromycin oxime |
| US3855203A (en) * | 1973-05-03 | 1974-12-17 | Abbott Lab | 4{41 -o-sulfonyl erythromycin-9-o-oxime derivatives |
| US4328334A (en) * | 1979-04-02 | 1982-05-04 | Pliva Pharmaceutical And Chemical Works | 11-Aza-10-deoxo-10-dihydroerythromycin A and derivatives thereof as well as a process for their preparation |
| US4526889A (en) * | 1982-11-15 | 1985-07-02 | Pfizer Inc. | Epimeric azahomoerythromycin A derivative, intermediates and method of use |
| US5075289A (en) * | 1988-06-07 | 1991-12-24 | Abbott Laboratories | 9-r-azacyclic erythromycin antibiotics |
Also Published As
| Publication number | Publication date |
|---|---|
| YU31319B (en) | 1973-04-30 |
| AT278241B (de) | 1970-01-26 |
| CH503016A (de) | 1971-02-15 |
| FR1584610A (ru) | 1969-12-26 |
| CS151478B2 (ru) | 1973-10-19 |
| SU664568A3 (ru) | 1979-05-25 |
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