FI60714C - Foerfarande foer framstaellning av saosom laekemedel anvaendbara 1-n-substituerade derivat av 4,6-di-(aminoglykosyl)-1,3-diaminocyklitoler - Google Patents
Foerfarande foer framstaellning av saosom laekemedel anvaendbara 1-n-substituerade derivat av 4,6-di-(aminoglykosyl)-1,3-diaminocyklitoler Download PDFInfo
- Publication number
- FI60714C FI60714C FI750141A FI750141A FI60714C FI 60714 C FI60714 C FI 60714C FI 750141 A FI750141 A FI 750141A FI 750141 A FI750141 A FI 750141A FI 60714 C FI60714 C FI 60714C
- Authority
- FI
- Finland
- Prior art keywords
- gentamicin
- amino
- acid
- aminoglycosyl
- antibiotic
- Prior art date
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- 239000002253 acid Substances 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 14
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical class O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims description 10
- RHRAMPXHWHSKQB-GGEUKFTFSA-N betamicin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)O)[C@@H](N)C[C@H]1N RHRAMPXHWHSKQB-GGEUKFTFSA-N 0.000 claims description 9
- RHRAMPXHWHSKQB-UHFFFAOYSA-N gentamicin B Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(C(O)C(O)C(CN)O2)O)C(N)CC1N RHRAMPXHWHSKQB-UHFFFAOYSA-N 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 8
- XUSXOPRDIDWMFO-UHFFFAOYSA-N Verdamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(O2)C(C)N)N)C(N)CC1N XUSXOPRDIDWMFO-UHFFFAOYSA-N 0.000 claims description 7
- VEGXETMJINRLTH-BOZYPMBZSA-N gentamycin C1a Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N VEGXETMJINRLTH-BOZYPMBZSA-N 0.000 claims description 7
- XUSXOPRDIDWMFO-CTMSJIKGSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[[(2s,3r)-3-amino-6-[(1s)-1-aminoethyl]-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(O2)[C@H](C)N)N)[C@@H](N)C[C@H]1N XUSXOPRDIDWMFO-CTMSJIKGSA-N 0.000 claims description 6
- WYJSPPYVEJPMJA-DJWUNRQOSA-N Antibiotic JI-20B Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H]([C@@H](C)N)O2)N)[C@@H](N)C[C@H]1N WYJSPPYVEJPMJA-DJWUNRQOSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- URWAJWIAIPFPJE-UHFFFAOYSA-N Rickamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(CN)O2)N)C(N)CC1N URWAJWIAIPFPJE-UHFFFAOYSA-N 0.000 claims description 5
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- URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 claims description 5
- VIAXDDBFFSKHGA-UHFFFAOYSA-N Antibiotic G52 Natural products CNC1CC(N)C(OC2OCC(C)(O)C(NC)C2O)C(O)C1OC3OC(=CCC3N)CN VIAXDDBFFSKHGA-UHFFFAOYSA-N 0.000 claims description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- ARCVBMPERJRMKB-UHFFFAOYSA-N antibiotic g-52 Chemical compound O1C(CNC)=CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N ARCVBMPERJRMKB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- BRZYSWJRSDMWLG-DJWUNRQOSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-[(1r)-1-hydroxyethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H]([C@@H](C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-DJWUNRQOSA-N 0.000 claims description 3
- YQGZDAPJXRYYLX-ZFAMMYHGSA-N Antibiotic JI-20A Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N YQGZDAPJXRYYLX-ZFAMMYHGSA-N 0.000 claims description 3
- 150000001718 carbodiimides Chemical class 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 150000001875 compounds Chemical class 0.000 description 31
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- 238000003756 stirring Methods 0.000 description 26
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- 239000000243 solution Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
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- 239000000047 product Substances 0.000 description 19
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
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- 229910002027 silica gel Inorganic materials 0.000 description 15
- 239000012141 concentrate Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- -1 antibiotic cum G-418 Chemical compound 0.000 description 11
- 239000003480 eluent Substances 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
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- 239000012065 filter cake Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229930076781 gentamycin C1 Natural products 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000008774 maternal effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YTXAYGAYACWVGD-UHFFFAOYSA-N palladium;hydrate Chemical compound O.[Pd] YTXAYGAYACWVGD-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic 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
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
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
-
- 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
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45257174A | 1974-03-19 | 1974-03-19 | |
| US05/452,586 US4029882A (en) | 1974-03-19 | 1974-03-19 | Selective acylation of the C-1 amino group of aminoglycoside antibiotics |
| US45258674 | 1974-03-19 | ||
| US45257174 | 1974-03-19 | ||
| CH1060174 | 1974-07-31 | ||
| CH1060174 | 1974-07-31 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI750141A7 FI750141A7 (enrdf_load_stackoverflow) | 1975-09-20 |
| FI60714B FI60714B (fi) | 1981-11-30 |
| FI60714C true FI60714C (fi) | 1982-03-10 |
Family
ID=27176473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI750141A FI60714C (fi) | 1974-03-19 | 1975-01-21 | Foerfarande foer framstaellning av saosom laekemedel anvaendbara 1-n-substituerade derivat av 4,6-di-(aminoglykosyl)-1,3-diaminocyklitoler |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2007783B1 (en) * | 2006-04-03 | 2018-07-11 | Technion Research & Development Foundation Ltd. | Novel aminoglycosides and uses thereof in the treatment of genetic disorders |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3780018A (en) * | 1972-06-26 | 1973-12-18 | Bristol Myers Co | Derivatives of gentamicin c1 |
| US3796698A (en) * | 1972-10-18 | 1974-03-12 | Bristol Myers Co | Antibiotic derivatives of gentamicin c2 |
| US3796699A (en) * | 1972-11-06 | 1974-03-12 | Bristol Myers Co | Antibiotic derivatives of gentamicin c1a |
-
1975
- 1975-01-21 LU LU71687*A patent/LU71687A1/xx unknown
- 1975-01-21 NL NLAANVRAGE7500690,A patent/NL183826C/xx not_active IP Right Cessation
- 1975-01-21 FI FI750141A patent/FI60714C/sv not_active IP Right Cessation
- 1975-01-21 ES ES433990A patent/ES433990A1/es not_active Expired
- 1975-01-21 NO NO750168A patent/NO140426C/no unknown
- 1975-01-21 IT IT19435/75A patent/IT1049348B/it active
- 1975-01-21 AT AT42975A patent/AT341088B/de not_active IP Right Cessation
- 1975-01-22 JP JP50009654A patent/JPS5843398B2/ja not_active Expired
- 1975-01-22 DK DK018675A patent/DK156070C/da not_active IP Right Cessation
- 1975-01-23 HU HU75SCHE507A patent/HU175673B/hu unknown
- 1975-01-23 DD DD183784A patent/DD117871A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK156070B (da) | 1989-06-19 |
| JPS50126640A (enrdf_load_stackoverflow) | 1975-10-04 |
| NO140426C (no) | 1979-08-29 |
| NL183826C (nl) | 1989-02-01 |
| HU175673B (hu) | 1980-09-28 |
| NL183826B (nl) | 1988-09-01 |
| DK18675A (enrdf_load_stackoverflow) | 1975-09-20 |
| FI750141A7 (enrdf_load_stackoverflow) | 1975-09-20 |
| ES433990A1 (es) | 1977-03-01 |
| JPS5843398B2 (ja) | 1983-09-27 |
| LU71687A1 (enrdf_load_stackoverflow) | 1975-12-09 |
| ATA42975A (de) | 1977-05-15 |
| NO750168L (enrdf_load_stackoverflow) | 1975-09-22 |
| NO140426B (no) | 1979-05-21 |
| FI60714B (fi) | 1981-11-30 |
| AT341088B (de) | 1978-01-25 |
| DK156070C (da) | 1989-11-06 |
| NL7500690A (nl) | 1975-09-23 |
| DD117871A5 (enrdf_load_stackoverflow) | 1976-02-05 |
| IT1049348B (it) | 1981-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired | ||
| MA | Patent expired |
Owner name: SCHERICO LTD |