GB1445872A - 2-deoxystreptamine-aminoglycosides and methods for their preparation paration - Google Patents
2-deoxystreptamine-aminoglycosides and methods for their preparation parationInfo
- Publication number
- GB1445872A GB1445872A GB2671973A GB2671973A GB1445872A GB 1445872 A GB1445872 A GB 1445872A GB 2671973 A GB2671973 A GB 2671973A GB 2671973 A GB2671973 A GB 2671973A GB 1445872 A GB1445872 A GB 1445872A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- free
- hydrogen
- hydroxyl group
- amino
- 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
Links
- 229940126575 aminoglycoside Drugs 0.000 title abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- 229930182566 Gentamicin Natural products 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229960003807 dibekacin Drugs 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- 229930027917 kanamycin Natural products 0.000 abstract 1
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical class O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- SYJXFKPQNSDJLI-HKEUSBCWSA-N neamine Chemical class N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](N)C[C@@H]1N SYJXFKPQNSDJLI-HKEUSBCWSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000005561 phenanthryl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 229960000707 tobramycin Drugs 0.000 abstract 1
- -1 tobramycin gentamycins Chemical class 0.000 abstract 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
-
- 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)
- 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)
Abstract
1445872 2-Deoxy-streptamine-aminoglycosides PFIZER Ltd 4 June 1974 [5 June 1973] 26719/73 Heading C2C Novel 2-dioxystreptamines and their acid addition salts in which R is an aromatic carboxylic or heterocyclic group, R<SP>1</SP> is hydrogen or methyl R<SP>2</SP> is amino or hydroxy, R<SP>3</SP> is hydrogen or hydroxy. R<SP>5</SP> is hydrogen or a group of Formulµ VI or VII and the dotted line represents an optional bond when each R<SP>3</SP> is hydrogen are prepared by reacting a compound II in which R<SP>2</SP>' is a free or protected hydroxyl group, R<SP>3'</SP> is hydrogen or a free or protected hydroxyl group, R<SP>4</SP> is a mono-valent protecting group for a primary amino group, and R<SP>6</SP> is a free or protected hydroxyl group or a group OR<SP>5'</SP> in which R<SP>5'</SP> is a Group VI or VII in which any free amino group is replaced by NHR<SP>4</SP> and any free hydroxyl group is optionally protected and R<SP>7</SP> is a free or protected hydroxyl group or a compound V with (1) an aldehyde R-CHO are simultaneously or subsequently reducing the Schiffs base so formed (2) a halide R-CH 2 -X where X is halogen or (3) an acylating agent derived from an acid R-COOH and reducing the R-CO group so formed, and thereafter removing any amino or hydroxyl protecting groups. Compounds I prepared are the 6<SP>1</SP>-(R-CH 2 ) derivatives of neamine, kanamycins A and B, tobramycin gentamycins C 1a and C 2 and 3,41- dideoxy-kanamycin B, in which R is phenyl (optionally substituted by Me, OH, NMe 2 , CF 3 , NH 2 , NH-COCH 3 , Ph, CH 2 OH, F, Br, OB 3 , COOH, NO 2 , mono- or di-Cl or mono-, di- or tri-MeO), naphthyl, phenanthryl, furyl, thienyl (optionally substituted by Me) pyrrolyl, indolyl or pyridinyl (optionally substituted by Cl). Compounds I have anti-bacterial activity and form with a carrier a pharmaceutical composition which may be administered orally or parenterally.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2671973A GB1445872A (en) | 1973-06-05 | 1973-06-05 | 2-deoxystreptamine-aminoglycosides and methods for their preparation paration |
| US05/476,269 US4024332A (en) | 1973-06-05 | 1974-06-04 | Aminoglycoside antibiotics and intermediates therefor |
| FR7419268A FR2232326B1 (en) | 1973-06-05 | 1974-06-04 | |
| NL7407483A NL7407483A (en) | 1973-06-05 | 1974-06-04 | |
| LU70223A LU70223A1 (en) | 1973-06-05 | 1974-06-04 | |
| DE19742427096 DE2427096A1 (en) | 1973-06-05 | 1974-06-05 | 2-DEOXYSTREPTAMINE AMINOGLYCOSIDES AND THE METHOD OF MANUFACTURING THEREOF |
| ES426998A ES426998A1 (en) | 1973-06-05 | 1974-06-05 | Aminoglycoside antibiotics and intermediates therefor |
| JP49063829A JPS5035131A (en) | 1973-06-05 | 1974-06-05 | |
| DK304574A DK304574A (en) | 1973-06-05 | 1974-06-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2671973A GB1445872A (en) | 1973-06-05 | 1973-06-05 | 2-deoxystreptamine-aminoglycosides and methods for their preparation paration |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1445872A true GB1445872A (en) | 1976-08-11 |
Family
ID=10248165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2671973A Expired GB1445872A (en) | 1973-06-05 | 1973-06-05 | 2-deoxystreptamine-aminoglycosides and methods for their preparation paration |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1445872A (en) |
-
1973
- 1973-06-05 GB GB2671973A patent/GB1445872A/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |