IL40151A - Aminoglycoside antibiotics and preparation thereof from micromonospora - Google Patents
Aminoglycoside antibiotics and preparation thereof from micromonosporaInfo
- Publication number
- IL40151A IL40151A IL40151A IL4015172A IL40151A IL 40151 A IL40151 A IL 40151A IL 40151 A IL40151 A IL 40151A IL 4015172 A IL4015172 A IL 4015172A IL 40151 A IL40151 A IL 40151A
- Authority
- IL
- Israel
- Prior art keywords
- antibiotic
- acid addition
- verdamicin
- process according
- pharmaceutically acceptable
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
- C07H15/236—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2 a saccharide radical being substituted by an alkylamino radical in position 3 and by two substituents different from hydrogen in position 4, e.g. gentamicin complex, sisomicin, verdamycin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Claims (18)
1. May-21-1975 992X-Israel SK/ch 1. Antibiotically active compounds having the general formula I wherein the dotted line. indicates a possible second bond between C4 ' and C5 ' and wherein either R^, and R^ are all hydroxy whereby there is a single bond between C4 ' and C5 ' , or R.^ is NH2 and R2 and R. are both hydrogen whereby there is a double bond between C4 ' and C5 ' , as well as acid addition salts of such compounds.
2. Compound according to claim 1 having the formula 40151-3 ay-21-1975 992X-Israel SK/ch and the infrared spectrum in mineral oil and the N.M.R. spectrum in deuteriomethanol substantially as shown in Figures 3 and 4 respectively of the accompanying drawings, said compound being designated antibiotic G-418.
3. Pharmaceutically acceptable acid addition salts of antibiotic G-418 defined in claim 2.
4. Antibiotic G-418 sulfate.
5. A compound according to claim 1 having the general formula and the infrared spectrum in mineral oil and the N.M.R. spectrum in a mixture of deuterium oxide and dimethyl-sulfoxide substantially as shown in Figures 1 and 2 of the accompanying drawings, said compound being .designated Verdamicin I . πι. -3 May-21-1975 992X-Israel SK/ch
6. Pharmaceutically acceptable acid addition salts of Verdamicin I defined in claim 5.
7. Verdamicin I sulfate.
8. Verdamicin I hydrochloride.
9. An antibiotically active composition comprising antibiotic G-418 defined in claim 2 , or a pharmaceutically acceptable acid addition salt thereof, together with at least one antibiotic selected from Verdamicin I defined in claim 5^ Sisomicin and Gentamicin A, or a pharmaceutically acceptable acid addition salt thereof, in admixture with a pharmaceutically acceptable carrier or excipient.
10. An antibiotically active composition comprising Verdamicin I or an acid addition salt thereof, together with a least one antibiotic selected from sisomicin and gentamicin A, or a pharmaceutically acceptable acid addition salt thereof, in admixture with a pharmaceutically acceptable carrier or excipient.
11. Pharmaceutical compositions comprising as active ingredient at least one compound selected from antibiotic G-418 defined in claim 2 and Verdamicin I defined in claim 5 and their pharmaceutically acceptable acid addition salts, May 21-1975 992X-Israel SK/ch
12. Compositions according to claim 11 in the form of dosage units .
13. Compositions according to claim 11 or claim 12 in the form of injectable preparations in ampoules.
14. Compositions according to claim 11 in the form of ointments, creams or lotions.
15. Compositions according to any of claims 11 to 14 wherein the active ingredient is a pharmaceutically acceptable acid addition salt of antibiotic G-418 or Verdamicin I.
16. Method for the preparation of an antibiotically active composition which comprises bringing an active ingredient selected from antibiotic G-418 (defined in claim 2) and Verdamicin I (defined in claim 5) and the pharmaceutically acceptable acid addition salts thereof, into a form suitable for therapeutic administration.
17. Method according to claim 16 which comprises mixing said active ingredient with a pharmaceutical carrier or excipient.
18. Antibiotic G-418 as herein defined and substanib d 40151-3 '■ May-21-1975 ^ 992X-Israel SK/ch 20. Process for the preparation of an antibiotically active substance containing the antibiotics Verdamicin I,' Antibiotic G-418, Sisomicin and Gentamicin A and of the acid addition salts aH^-6ehif€-fee«e-exe*^i^iinre--dier .'ve--txves-thereof , which comprises cultivating a microorganism of the species Micromonospora grisea in ah aqueous nutrient medium under aerobic conditions until substantial antibiotic activity is imparted to the medium. 21. Process according to claim 20 wherein the microorganism is cultivated in a nutrient medium under submerged aerobic conditions. 22. Process according to claim 20 or claim 21 wherein the cultivation is effected at a temperature of from 20° to 40°C. 23. Process according to claim 22 wherein the temperature is from 28° to 35°C. 24. Process according to any of claims 20 to 23 wherein the cultivation is effected at a pH of 6.5 to 8.5. 25. Process according to any of claims 20 to 24 wherein the cultivation is effected at a pH of 7.2 to 8.3. 26. Process according to any of claims 20 to 25 wherein the microorganism of the species Mi romonospora grisea 4,0151-3 May-21-1975 992X-Israel SK/ch 27. Process according to any of claims 20 to 26 wherein at least one of the antibiotics Verdamicin I, Antibiotic G-418, Sisomicin and Gentamicin A are recovered from the fermentation medium or from the mycelium. 28. Process according to any of claims 20 to 27 wherein the recovery comprises acidifying the fermentation medium, separating the mycelium therefrom, neutralising the fermentation medium, and extracting an antibiotically active substance therefrom. 29. Process according to claim 27 or claim 28 wherein antibiotic G-418 having the formula is isolated in the free form. 30. Process according to claim 27 or claim 28 wherein antibiotic G-418 is isolated in the form of a pharma ^ 992X-Israel SK/ch 31. Process according to claim 30 wherein the pharmaceutically acceptable acid addition salt is the sulfate. 32. Process according to claim 27 or claim 28 wherein the novel antibiotic designated Verdamicin I, having the formula is isolated in the free form from the antibiotically active substance. 33. Process according to claim 27 or claim 28 wherein Verdamicin I is isolated in the form of a pharmaceutically acceptable acid addition salt. 34. Process according to claim 33 wherein the pharmaceutically acceptable acid addition salt is the sulphate. . May 21 1975 992X-Israel SK/ch 35. Process according to claim 27 or 28 wherein a mixture of two or more of the antibiotics Sisomicin, Verdamicin I, gentamicin A and antibiotic G-418 is isolated from the antibiotically active substance. 36. Process according to claim 35 wherein a mixture of two or more of the antibiotics Verdamicin I, Sisomicin, gentamicin A and antibiotic G-418 is isolated in the free form. 35 , 37. Process according to claim 6i>_wherein a mixture of two or more of the antibiotics Verdamicin I, Sisomicin, gentamicin A and antibiotic G-418 is isolated in the form of a pharmaceutically acceptable acid addition salt. 38. Process according to claim 37, wherein the acid addition salt is the sulfate. 39. Process according to claim 27 or claim 28 wherein gentamicin A and/or sisomicin is isolated from the antibiotically active substance. 40. Process according to claim 39, wherein gentamicin A and/or Sisomicin is isolated in the form of a pharmaceutically acceptable acid addition salt. 40151-3 May 21,1975 992X-Israel SK/ch 41. The antibiotically active substances Sisomicin, Verdamicin I, gentamicin A, Antibiotic G-418 and their acid addition salts whenever prepared by a process as claimed in any of claims 20 to 40. 42. Antibiotic G-418 whenever isolated by the process of claim 29. 43. Pharmaceutically acceptable acid addition salts of antibiotic G-418 whenever isolated by the process of claim 30. 44. Verdamicin I whenever isolated by the process of claim 32. 45. Pharmaceutically acceptable acid addition salts of Verdamicin I whenever isolated by the process of claim 33. 46. Gentamicin A and sisomicin and pharmaceutically acceptable acid addition salts thereof whenever isolated by a process as claimed in any of claims 39 and 40. Attowye i0T Ap lican
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19670771A | 1971-11-08 | 1971-11-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40151A0 IL40151A0 (en) | 1972-10-29 |
| IL40151A true IL40151A (en) | 1976-01-30 |
Family
ID=22726520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40151A IL40151A (en) | 1971-11-08 | 1972-08-17 | Aminoglycoside antibiotics and preparation thereof from micromonospora |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS4852991A (en) |
| AR (1) | AR193286A1 (en) |
| AT (1) | AT319469B (en) |
| BE (1) | BE787758A (en) |
| CA (1) | CA972303A (en) |
| CH (1) | CH586281A5 (en) |
| CS (1) | CS163282B2 (en) |
| DD (1) | DD102161A5 (en) |
| DE (1) | DE2239964A1 (en) |
| DK (1) | DK130847B (en) |
| FR (1) | FR2159246A1 (en) |
| IL (1) | IL40151A (en) |
| LU (1) | LU65922A1 (en) |
| NL (1) | NL7211265A (en) |
| NO (1) | NO136050C (en) |
| OA (1) | OA04260A (en) |
| PH (1) | PH13016A (en) |
| PL (1) | PL84893B1 (en) |
| RO (1) | RO58761A (en) |
| SE (1) | SE384691B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2201872B1 (en) * | 1972-10-10 | 1977-01-28 | Scherico Ltd |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7012428A (en) * | 1969-08-25 | 1971-03-01 | ||
| CH551965A (en) * | 1970-06-22 | 1974-07-31 | Scherico Ltd | PROCESS FOR PRODUCING ANTIBIOTICALLY ACTIVE COMPOUNDS. |
-
0
- BE BE787758D patent/BE787758A/en unknown
-
1972
- 1972-08-14 DE DE2239964A patent/DE2239964A1/en active Pending
- 1972-08-16 CH CH1211472A patent/CH586281A5/xx not_active IP Right Cessation
- 1972-08-17 AT AT712272A patent/AT319469B/en not_active IP Right Cessation
- 1972-08-17 PH PH13813A patent/PH13016A/en unknown
- 1972-08-17 NL NL7211265A patent/NL7211265A/xx not_active Application Discontinuation
- 1972-08-17 CS CS5710A patent/CS163282B2/cs unknown
- 1972-08-17 DD DD165307A patent/DD102161A5/xx unknown
- 1972-08-17 FR FR7229471A patent/FR2159246A1/en active Granted
- 1972-08-17 SE SE7210703A patent/SE384691B/en unknown
- 1972-08-17 CA CA149,843A patent/CA972303A/en not_active Expired
- 1972-08-17 NO NO2955/72A patent/NO136050C/en unknown
- 1972-08-17 DK DK407772AA patent/DK130847B/en unknown
- 1972-08-17 IL IL40151A patent/IL40151A/en unknown
- 1972-08-17 RO RO71981A patent/RO58761A/ro unknown
- 1972-08-17 PL PL1972157318A patent/PL84893B1/pl unknown
- 1972-08-18 AR AR243622A patent/AR193286A1/en active
- 1972-08-18 LU LU65922A patent/LU65922A1/xx unknown
- 1972-08-18 OA OA54666A patent/OA04260A/en unknown
- 1972-08-18 JP JP47082680A patent/JPS4852991A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NO136050B (en) | 1977-04-04 |
| RO58761A (en) | 1975-12-15 |
| DE2239964A1 (en) | 1973-06-14 |
| OA04260A (en) | 1979-12-31 |
| SE384691B (en) | 1976-05-17 |
| DK130847C (en) | 1975-09-29 |
| BE787758A (en) | 1973-02-19 |
| DD102161A5 (en) | 1973-12-05 |
| FR2159246B1 (en) | 1976-03-05 |
| CA972303A (en) | 1975-08-05 |
| PL84893B1 (en) | 1976-04-30 |
| LU65922A1 (en) | 1973-01-15 |
| PH13016A (en) | 1979-11-09 |
| JPS4852991A (en) | 1973-07-25 |
| NL7211265A (en) | 1973-05-10 |
| IL40151A0 (en) | 1972-10-29 |
| AT319469B (en) | 1974-12-27 |
| CH586281A5 (en) | 1977-03-31 |
| DK130847B (en) | 1975-04-21 |
| CS163282B2 (en) | 1975-08-29 |
| FR2159246A1 (en) | 1973-06-22 |
| AR193286A1 (en) | 1973-04-11 |
| NO136050C (en) | 1977-07-13 |
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