PL111474B1 - Process for preparing novel neamine drivatives - Google Patents
Process for preparing novel neamine drivatives Download PDFInfo
- Publication number
- PL111474B1 PL111474B1 PL1976192253A PL19225376A PL111474B1 PL 111474 B1 PL111474 B1 PL 111474B1 PL 1976192253 A PL1976192253 A PL 1976192253A PL 19225376 A PL19225376 A PL 19225376A PL 111474 B1 PL111474 B1 PL 111474B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- nht
- compound
- neamine
- carbon atoms
- Prior art date
Links
- SYJXFKPQNSDJLI-HKEUSBCWSA-N neamine Chemical compound 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 title claims 38
- 238000004519 manufacturing process Methods 0.000 title 1
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 4
- 101100006982 Mus musculus Ppcdc gene Proteins 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 21
- 125000004432 carbon atom Chemical group C* 0.000 claims 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
- -1 carboxylic acid hydrocarbon radical Chemical class 0.000 claims 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 8
- 125000003277 amino group Chemical group 0.000 claims 8
- 238000010992 reflux Methods 0.000 claims 8
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 8
- 125000002252 acyl group Chemical group 0.000 claims 6
- FQGYCXFLEQVDJQ-UHFFFAOYSA-N mercury dicyanide Chemical compound N#C[Hg]C#N FQGYCXFLEQVDJQ-UHFFFAOYSA-N 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 5
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 239000003513 alkali Substances 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000007864 aqueous solution Substances 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 239000011347 resin Substances 0.000 claims 4
- 229920005989 resin Polymers 0.000 claims 4
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 claims 3
- 125000004442 acylamino group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000006242 amine protecting group Chemical group 0.000 claims 3
- 238000006206 glycosylation reaction Methods 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000004983 dialkoxyalkyl group Chemical group 0.000 claims 2
- 230000013595 glycosylation Effects 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims 1
- 241000251468 Actinopterygii Species 0.000 claims 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229940126657 Compound 17 Drugs 0.000 claims 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims 1
- 238000007171 acid catalysis Methods 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- RBADLHJXVXRWQY-UHFFFAOYSA-N benzene;nitromethane Chemical compound C[N+]([O-])=O.C1=CC=CC=C1 RBADLHJXVXRWQY-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 229960003328 benzoyl peroxide Drugs 0.000 claims 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229940126086 compound 21 Drugs 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 1
- 230000037361 pathway Effects 0.000 claims 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 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
- C07H15/224—Cyclohexane rings substituted by at least two nitrogen atoms with only one saccharide radical directly attached to the cyclohexyl radical, e.g. destomycin, fortimicin, neamine
-
- 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
-
- 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
-
- 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)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/611,349 US3996205A (en) | 1975-09-08 | 1975-09-08 | Aminoglycoside antibiotics and intermediates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL192253A1 PL192253A1 (pl) | 1979-02-26 |
| PL111474B1 true PL111474B1 (en) | 1980-08-30 |
Family
ID=24448676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976192253A PL111474B1 (en) | 1975-09-08 | 1976-09-08 | Process for preparing novel neamine drivatives |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3996205A (member.php) |
| JP (1) | JPS5233649A (member.php) |
| AU (1) | AU506262B2 (member.php) |
| BE (1) | BE845942A (member.php) |
| CA (1) | CA1067899A (member.php) |
| CH (1) | CH626896A5 (member.php) |
| DE (1) | DE2638794A1 (member.php) |
| FR (2) | FR2322608A1 (member.php) |
| GB (1) | GB1530643A (member.php) |
| HU (1) | HU177271B (member.php) |
| NL (1) | NL7609874A (member.php) |
| PL (1) | PL111474B1 (member.php) |
| SU (1) | SU700066A3 (member.php) |
| ZA (1) | ZA764726B (member.php) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4182855A (en) * | 1977-05-05 | 1980-01-08 | The Upjohn Company | Nitrosugar |
| US7794713B2 (en) | 2004-04-07 | 2010-09-14 | Lpath, Inc. | Compositions and methods for the treatment and prevention of hyperproliferative diseases |
| PL2390255T3 (pl) | 2006-04-03 | 2017-01-31 | Technion Research & Development Foundation Ltd. | Nowe aminoglikozydy i ich zastosowania w leczeniu zaburzeń genetycznych |
| US7862812B2 (en) | 2006-05-31 | 2011-01-04 | Lpath, Inc. | Methods for decreasing immune response and treating immune conditions |
| JP6862428B6 (ja) | 2015-09-02 | 2021-06-02 | エロックス ファーマシューティカルズ リミテッド | アミノグリコシド誘導体および遺伝性疾患の治療におけるその使用 |
| EP3344640A4 (en) | 2015-09-02 | 2019-05-01 | Eloxx Pharmaceuticals Ltd. | AMINO-LIKES DERIVATIVES AND USES THEREOF FOR THE TREATMENT OF GENETIC DISEASES |
| US10786520B2 (en) | 2015-09-02 | 2020-09-29 | Eloxx Pharmaceuticals Ltd. | Aminoglycoside derivatives and uses thereof in treating genetic disorders |
| WO2018167794A1 (en) | 2017-03-15 | 2018-09-20 | Eloxx Pharmaceuticals Ltd. | Large scale preparation of pseudo-trisaccharide aminoglycosides and of intermediates thereof |
| EP3883943A4 (en) | 2018-11-22 | 2023-01-04 | Technion Research & Development Foundation Limited | MODIFIED AMINOGLYCOSIDE COMPOUNDS AND THEIR USES TO DEACTIVATE BACTERIAL RIBOSOMES |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH84A (fr) * | 1889-01-10 | Fontainemelon Horlogerie | Perfectionnement apporté dans la construction des mécanismes de remontoir des montres de tous calibres | |
| JPS507595B1 (member.php) * | 1970-07-29 | 1975-03-27 | ||
| US3792037A (en) * | 1971-11-04 | 1974-02-12 | Bristol Myers Co | Process for preparing ambutyrosin |
| CA992535A (en) * | 1972-03-08 | 1976-07-06 | Bristol-Myers Squibb Company | Antibiotic derivatives |
| US3897412A (en) * | 1972-05-04 | 1975-07-29 | Bristol Myers Co | Paromomycin antibiotic derivatives |
| US3860574A (en) * | 1972-12-06 | 1975-01-14 | Bristol Myers Co | Derivatives of neomycin b and neomycin c |
| US3886139A (en) * | 1973-02-23 | 1975-05-27 | Bristol Myers Co | Derivatives of kanamycin |
| US3893997A (en) * | 1974-07-01 | 1975-07-08 | Smithkline Corp | Pseudodisaccharide intermediates |
-
1975
- 1975-09-08 US US05/611,349 patent/US3996205A/en not_active Expired - Lifetime
-
1976
- 1976-07-27 CA CA257,925A patent/CA1067899A/en not_active Expired
- 1976-08-05 ZA ZA764726A patent/ZA764726B/xx unknown
- 1976-08-06 AU AU16626/76A patent/AU506262B2/en not_active Expired
- 1976-08-19 GB GB34527/76A patent/GB1530643A/en not_active Expired
- 1976-08-27 DE DE19762638794 patent/DE2638794A1/de not_active Withdrawn
- 1976-09-03 JP JP51105075A patent/JPS5233649A/ja active Pending
- 1976-09-06 NL NL7609874A patent/NL7609874A/xx not_active Application Discontinuation
- 1976-09-07 FR FR7626904A patent/FR2322608A1/fr active Granted
- 1976-09-07 SU SU762393663A patent/SU700066A3/ru active
- 1976-09-08 PL PL1976192253A patent/PL111474B1/pl unknown
- 1976-09-08 HU HU76UO124A patent/HU177271B/hu unknown
- 1976-09-08 BE BE170428A patent/BE845942A/xx not_active IP Right Cessation
- 1976-09-08 CH CH1140476A patent/CH626896A5/de not_active IP Right Cessation
-
1977
- 1977-08-05 FR FR7724310A patent/FR2355852A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US3996205A (en) | 1976-12-07 |
| GB1530643A (en) | 1978-11-01 |
| ZA764726B (en) | 1977-07-27 |
| PL192253A1 (pl) | 1979-02-26 |
| NL7609874A (nl) | 1977-03-10 |
| AU1662676A (en) | 1978-02-09 |
| FR2322608A1 (fr) | 1977-04-01 |
| HU177271B (en) | 1981-08-28 |
| SU700066A3 (ru) | 1979-11-25 |
| JPS5233649A (en) | 1977-03-14 |
| AU506262B2 (en) | 1979-12-20 |
| FR2322608B1 (member.php) | 1979-09-07 |
| FR2355852A1 (fr) | 1978-01-20 |
| FR2355852B1 (member.php) | 1980-04-04 |
| CH626896A5 (member.php) | 1981-12-15 |
| CA1067899A (en) | 1979-12-11 |
| BE845942A (fr) | 1977-03-08 |
| DE2638794A1 (de) | 1977-03-10 |
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