NL8300893A - 6'-alkylanaloga van spectinomycine en werkwijze voor het bereiden daarvan. - Google Patents
6'-alkylanaloga van spectinomycine en werkwijze voor het bereiden daarvan. Download PDFInfo
- Publication number
- NL8300893A NL8300893A NL8300893A NL8300893A NL8300893A NL 8300893 A NL8300893 A NL 8300893A NL 8300893 A NL8300893 A NL 8300893A NL 8300893 A NL8300893 A NL 8300893A NL 8300893 A NL8300893 A NL 8300893A
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- Netherlands
- Prior art keywords
- compound
- formula
- ch3c
- hydrogen
- thio
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- 238000000034 method Methods 0.000 title claims description 19
- 229960000268 spectinomycin Drugs 0.000 title claims description 12
- UNFWWIHTNXNPBV-WXKVUWSESA-N spectinomycin Chemical compound O([C@@H]1[C@@H](NC)[C@@H](O)[C@H]([C@@H]([C@H]1O1)O)NC)[C@]2(O)[C@H]1O[C@H](C)CC2=O UNFWWIHTNXNPBV-WXKVUWSESA-N 0.000 title claims description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- -1 compound compound Chemical class 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 81
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- 239000000243 solution Substances 0.000 description 32
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
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- 239000002253 acid Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 5
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- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 208000001786 gonorrhea Diseases 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- GRYDGXUVWLGHPL-UHFFFAOYSA-M magnesium;heptane;bromide Chemical compound [Mg+2].[Br-].CCCCCC[CH2-] GRYDGXUVWLGHPL-UHFFFAOYSA-M 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/04—Ortho-condensed systems
-
- 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
- C07H15/224—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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35972382A | 1982-03-19 | 1982-03-19 | |
| US35972382 | 1982-03-19 | ||
| US44930482 | 1982-12-13 | ||
| US06/449,304 US4532336A (en) | 1982-03-19 | 1982-12-13 | 6'-Alkylspectinomycins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8300893A true NL8300893A (nl) | 1983-10-17 |
Family
ID=27000602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8300893A NL8300893A (nl) | 1982-03-19 | 1983-03-11 | 6'-alkylanaloga van spectinomycine en werkwijze voor het bereiden daarvan. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4532336A (en, 2012) |
| JP (1) | JPH0776222B2 (en, 2012) |
| BE (1) | BE896215A (en, 2012) |
| DE (1) | DE3308196A1 (en, 2012) |
| FR (1) | FR2523583B1 (en, 2012) |
| GB (1) | GB2117757B (en, 2012) |
| HK (1) | HK61788A (en, 2012) |
| IT (1) | IT1164157B (en, 2012) |
| MX (1) | MX9203211A (en, 2012) |
| NL (1) | NL8300893A (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4532336A (en) * | 1982-03-19 | 1985-07-30 | The Upjohn Company | 6'-Alkylspectinomycins |
| US4578485A (en) * | 1984-02-08 | 1986-03-25 | The Upjohn Company | Synthesis of spectinomycin analogs by an improved Grignard process |
| EP0216898B1 (en) * | 1985-03-29 | 1990-06-13 | The Upjohn Company | Treating chlamydia infections using spectinomycin analogs |
| US4730059A (en) * | 1986-03-10 | 1988-03-08 | The Upjohn Company | 6'-thiomethylsubstituted spectinomycins |
| EP0593439A1 (en) * | 1989-09-13 | 1994-04-27 | The Upjohn Company | Gamma alkylation of a protected derivative of the enone of spectinomycin |
| US5048126A (en) * | 1989-10-02 | 1991-09-17 | Mclaughlin James G | Protective apparel |
| CN104725392B (zh) * | 2013-12-24 | 2017-01-11 | 中国农业大学 | 半抗原spe-ede及其相应的人工抗原与应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3234092A (en) * | 1959-10-20 | 1966-02-08 | Upjohn Co | Actinospectacin and process for producing same |
| DE2756914A1 (de) * | 1977-12-21 | 1979-07-05 | Thomae Gmbh Dr K | 4-spectinomycylamin und seine physiologisch vertraegliche salze, verfahren zur herstellung und diese stoffe enthaltende arzneimittel |
| US4351771A (en) * | 1979-03-13 | 1982-09-28 | The Upjohn Company | Spectinomycin analogs and methods for the preparation thereof |
| GB2050348B (en) * | 1979-03-13 | 1983-08-03 | Upjohn Co | Spectinomycin analogues |
| US4282152A (en) * | 1979-08-23 | 1981-08-04 | The Upjohn Company | Intermediates for preparing spectinomycin and analogs thereof |
| BE887456R (fr) * | 1981-02-10 | 1981-08-10 | Upjohn Co | Procede de production de composes intermediaires pour l'obtention de la spectinomycine et de ses analogues et produits de ce procede |
| US4420623A (en) * | 1981-07-20 | 1983-12-13 | The Upjohn Company | Process and intermediates for preparing 6'-methylspectinomycin and analogs thereof |
| US4380651A (en) * | 1981-07-20 | 1983-04-19 | The Upjohn Company | Process for preparing 6'-methylspectinomycin and analogs thereof |
| US4405797A (en) * | 1981-10-16 | 1983-09-20 | The Upjohn Company | Process for preparing spectinomycin analogs: N-demethylation of spectinomycin or its analogs and realkylation of the intermediates |
| US4465848A (en) * | 1981-10-23 | 1984-08-14 | The Upjohn Company | Spectinomycin compounds |
| US4532336A (en) * | 1982-03-19 | 1985-07-30 | The Upjohn Company | 6'-Alkylspectinomycins |
-
1982
- 1982-12-13 US US06/449,304 patent/US4532336A/en not_active Expired - Fee Related
-
1983
- 1983-02-14 GB GB08304026A patent/GB2117757B/en not_active Expired
- 1983-03-08 DE DE19833308196 patent/DE3308196A1/de active Granted
- 1983-03-11 NL NL8300893A patent/NL8300893A/nl not_active Application Discontinuation
- 1983-03-14 IT IT20066/83A patent/IT1164157B/it active
- 1983-03-18 BE BE0/210360A patent/BE896215A/fr not_active IP Right Cessation
- 1983-03-18 FR FR8304499A patent/FR2523583B1/fr not_active Expired
-
1988
- 1988-08-11 HK HK617/88A patent/HK61788A/xx not_active IP Right Cessation
-
1992
- 1992-06-24 MX MX9203211A patent/MX9203211A/es unknown
-
1993
- 1993-03-12 JP JP5051986A patent/JPH0776222B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT1164157B (it) | 1987-04-08 |
| GB8304026D0 (en) | 1983-03-16 |
| IT8320066A0 (it) | 1983-03-14 |
| DE3308196C2 (en, 2012) | 1993-06-09 |
| BE896215A (fr) | 1983-09-19 |
| JPH0776222B2 (ja) | 1995-08-16 |
| GB2117757A (en) | 1983-10-19 |
| FR2523583A1 (fr) | 1983-09-23 |
| US4532336A (en) | 1985-07-30 |
| DE3308196A1 (de) | 1983-09-29 |
| FR2523583B1 (fr) | 1987-06-12 |
| HK61788A (en) | 1988-08-19 |
| MX9203211A (es) | 1992-09-01 |
| JPH0649072A (ja) | 1994-02-22 |
| GB2117757B (en) | 1985-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |