FI100884B - Menetelmä sulfonyylipristinamysiini-IIB:n valmistamiseksi - Google Patents
Menetelmä sulfonyylipristinamysiini-IIB:n valmistamiseksi Download PDFInfo
- Publication number
- FI100884B FI100884B FI925643A FI925643A FI100884B FI 100884 B FI100884 B FI 100884B FI 925643 A FI925643 A FI 925643A FI 925643 A FI925643 A FI 925643A FI 100884 B FI100884 B FI 100884B
- Authority
- FI
- Finland
- Prior art keywords
- iib
- alk
- water
- diethylaminoethyl
- mmol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 19
- -1 alkali metal tungstate Chemical class 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 7
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical group [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 abstract description 10
- 230000003647 oxidation Effects 0.000 abstract description 9
- 108010015791 Streptogramin A Proteins 0.000 abstract description 7
- JOOMGSFOCRDAHL-XKCHLWDXSA-N pristinamycin-IIB Natural products CC(C)[C@@H]1OC(=O)[C@H]2CCCN2C(=O)c3coc(CC(=O)C[C@@H](O)C=C(C)C=CCNC(=O)C=C[C@H]1C)n3 JOOMGSFOCRDAHL-XKCHLWDXSA-N 0.000 abstract description 7
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229960002163 hydrogen peroxide Drugs 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 abstract 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 5
- 150000003457 sulfones Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- CUCXXSBYLSQIJF-UHFFFAOYSA-N 1,1-dichloroethane;hydrate Chemical compound O.CC(Cl)Cl CUCXXSBYLSQIJF-UHFFFAOYSA-N 0.000 description 1
- NTOIKDYVJIWVSU-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-UHFFFAOYSA-N 0.000 description 1
- YGXCETJZBDTKRY-UHFFFAOYSA-N Pristinamycin Component I A Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC(=CC=2)N(C)C)N(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O YGXCETJZBDTKRY-UHFFFAOYSA-N 0.000 description 1
- 108010015795 Streptogramin B Proteins 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OGODKNYCTJYXFF-UHFFFAOYSA-N bis(4-methylbenzoyl) 2,3-dihydroxybutanedioate Chemical compound C1=CC(C)=CC=C1C(=O)OC(=O)C(O)C(O)C(=O)OC(=O)C1=CC=C(C)C=C1 OGODKNYCTJYXFF-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- FIMJSWFMQJGVAM-UHFFFAOYSA-N chloroform;hydrate Chemical compound O.ClC(Cl)Cl FIMJSWFMQJGVAM-UHFFFAOYSA-N 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- AAQNGTNRWPXMPB-UHFFFAOYSA-N dipotassium;dioxido(dioxo)tungsten Chemical compound [K+].[K+].[O-][W]([O-])(=O)=O AAQNGTNRWPXMPB-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- YGXCETJZBDTKRY-DZCVGBHJSA-N pristinamycin IA Chemical compound N([C@@H]1C(=O)N[C@@H](C(N2CCC[C@H]2C(=O)N(C)[C@@H](CC=2C=CC(=CC=2)N(C)C)C(=O)N2CCC(=O)C[C@H]2C(=O)N[C@H](C(=O)O[C@@H]1C)C=1C=CC=CC=1)=O)CC)C(=O)C1=NC=CC=C1O YGXCETJZBDTKRY-DZCVGBHJSA-N 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06182—Dipeptides with the first amino acid being heterocyclic and Pristinamycin II; Derivatives thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Peptides Or Proteins (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
- Heat Treatment Of Sheet Steel (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR909009033A FR2664597B1 (fr) | 1990-07-16 | 1990-07-16 | Procede de preparation de sulfonylpristinamycine iib. |
| FR9009033 | 1990-07-16 | ||
| PCT/FR1991/000579 WO1992001692A1 (fr) | 1990-07-16 | 1991-07-15 | Procede de preparation de sulfonylpristinamycine ii¿b? |
| FR9100579 | 1991-07-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI925643L FI925643L (fi) | 1992-12-11 |
| FI925643A0 FI925643A0 (fi) | 1992-12-11 |
| FI100884B true FI100884B (fi) | 1998-03-13 |
Family
ID=9398751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI925643A FI100884B (fi) | 1990-07-16 | 1992-12-11 | Menetelmä sulfonyylipristinamysiini-IIB:n valmistamiseksi |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5347001A (enExample) |
| EP (1) | EP0539484B1 (enExample) |
| JP (1) | JP3345811B2 (enExample) |
| KR (1) | KR100199068B1 (enExample) |
| AT (1) | ATE147744T1 (enExample) |
| AU (1) | AU654145B2 (enExample) |
| CA (1) | CA2082636C (enExample) |
| DE (1) | DE69124241T2 (enExample) |
| DK (1) | DK0539484T3 (enExample) |
| ES (1) | ES2095946T3 (enExample) |
| FI (1) | FI100884B (enExample) |
| FR (1) | FR2664597B1 (enExample) |
| GR (1) | GR3022284T3 (enExample) |
| IE (1) | IE912446A1 (enExample) |
| IL (1) | IL98851A (enExample) |
| NZ (1) | NZ238948A (enExample) |
| PT (1) | PT98334B (enExample) |
| RU (1) | RU2073002C1 (enExample) |
| TW (1) | TW197438B (enExample) |
| WO (1) | WO1992001692A1 (enExample) |
| ZA (1) | ZA915443B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2664598A1 (fr) * | 1990-07-16 | 1992-01-17 | Rhone Poulenc Rorer Sa | Procede de preparation de sulfinyl pristinamycine iib. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2576022B1 (fr) * | 1985-01-11 | 1987-09-11 | Rhone Poulenc Sante | Nouveaux derives de la pristinamycine ii b, leur preparation et les compositions pharmaceutiques qui les contiennent |
| GB8616768D0 (en) * | 1986-07-09 | 1986-08-13 | May & Baker Ltd | Process |
| GB2206577B (en) * | 1987-07-07 | 1990-10-24 | May & Baker Ltd | New process for the preparation of therapeutically useful pristinamycin iib sulphone derivatives |
| EP0322800A1 (en) * | 1987-12-25 | 1989-07-05 | Sumitomo Pharmaceuticals Company, Limited | Process for preparation of sulfone derivatives |
-
1990
- 1990-07-16 FR FR909009033A patent/FR2664597B1/fr not_active Expired - Lifetime
-
1991
- 1991-07-12 ZA ZA915443A patent/ZA915443B/xx unknown
- 1991-07-12 IE IE244691A patent/IE912446A1/en not_active IP Right Cessation
- 1991-07-12 NZ NZ238948A patent/NZ238948A/en not_active IP Right Cessation
- 1991-07-15 CA CA002082636A patent/CA2082636C/fr not_active Expired - Lifetime
- 1991-07-15 IL IL9885191A patent/IL98851A/xx not_active IP Right Cessation
- 1991-07-15 DE DE69124241T patent/DE69124241T2/de not_active Expired - Lifetime
- 1991-07-15 KR KR1019930700113A patent/KR100199068B1/ko not_active Expired - Lifetime
- 1991-07-15 DK DK91913608.5T patent/DK0539484T3/da active
- 1991-07-15 RU RU9192016441A patent/RU2073002C1/ru active
- 1991-07-15 EP EP91913608A patent/EP0539484B1/fr not_active Expired - Lifetime
- 1991-07-15 US US07/961,915 patent/US5347001A/en not_active Expired - Lifetime
- 1991-07-15 AT AT91913608T patent/ATE147744T1/de not_active IP Right Cessation
- 1991-07-15 WO PCT/FR1991/000579 patent/WO1992001692A1/fr not_active Ceased
- 1991-07-15 ES ES91913608T patent/ES2095946T3/es not_active Expired - Lifetime
- 1991-07-15 AU AU82221/91A patent/AU654145B2/en not_active Expired
- 1991-07-15 JP JP51234991A patent/JP3345811B2/ja not_active Expired - Lifetime
- 1991-07-16 PT PT98334A patent/PT98334B/pt not_active IP Right Cessation
- 1991-07-16 TW TW080105509A patent/TW197438B/zh not_active IP Right Cessation
-
1992
- 1992-12-11 FI FI925643A patent/FI100884B/fi not_active IP Right Cessation
-
1997
- 1997-01-16 GR GR960402521T patent/GR3022284T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK0539484T3 (da) | 1997-03-03 |
| PT98334B (pt) | 1999-01-29 |
| FI925643L (fi) | 1992-12-11 |
| FI925643A0 (fi) | 1992-12-11 |
| IL98851A (en) | 1995-08-31 |
| DE69124241D1 (de) | 1997-02-27 |
| WO1992001692A1 (fr) | 1992-02-06 |
| IE912446A1 (en) | 1992-01-29 |
| AU8222191A (en) | 1992-02-18 |
| EP0539484B1 (fr) | 1997-01-15 |
| NZ238948A (en) | 1992-10-28 |
| ATE147744T1 (de) | 1997-02-15 |
| DE69124241T2 (de) | 1997-05-15 |
| ZA915443B (en) | 1993-03-31 |
| IL98851A0 (en) | 1992-07-15 |
| FR2664597A1 (fr) | 1992-01-17 |
| US5347001A (en) | 1994-09-13 |
| EP0539484A1 (fr) | 1993-05-05 |
| JP3345811B2 (ja) | 2002-11-18 |
| JPH05508651A (ja) | 1993-12-02 |
| KR100199068B1 (ko) | 1999-06-15 |
| KR930701449A (ko) | 1993-06-11 |
| FR2664597B1 (fr) | 1994-09-02 |
| ES2095946T3 (es) | 1997-03-01 |
| PT98334A (pt) | 1992-06-30 |
| RU2073002C1 (ru) | 1997-02-10 |
| GR3022284T3 (en) | 1997-04-30 |
| CA2082636C (fr) | 2002-05-21 |
| AU654145B2 (en) | 1994-10-27 |
| TW197438B (enExample) | 1993-01-01 |
| CA2082636A1 (fr) | 1992-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |