JPS62132852A - チアムフエニコ−ル（１）の製法 - Google Patents
チアムフエニコ−ル（１）の製法Info
- Publication number
- JPS62132852A JPS62132852A JP61287879A JP28787986A JPS62132852A JP S62132852 A JPS62132852 A JP S62132852A JP 61287879 A JP61287879 A JP 61287879A JP 28787986 A JP28787986 A JP 28787986A JP S62132852 A JPS62132852 A JP S62132852A
- Authority
- JP
- Japan
- Prior art keywords
- threo
- aminodiol
- hcl
- tables
- thiamphenicol
- 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.)
- Pending
Links
- OTVAEFIXJLOWRX-NXEZZACHSA-N thiamphenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-NXEZZACHSA-N 0.000 title claims abstract description 17
- 229960003053 thiamphenicol Drugs 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 238000000034 method Methods 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 39
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 23
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- 238000010956 selective crystallization Methods 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000011081 inoculation Methods 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- HKMLRUAPIDAGIE-UHFFFAOYSA-N methyl 2,2-dichloroacetate Chemical compound COC(=O)C(Cl)Cl HKMLRUAPIDAGIE-UHFFFAOYSA-N 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000013078 crystal Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- -1 methylene ester Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VUZPGEIXNYGDJN-UHFFFAOYSA-N 1-nitroethanol Chemical compound CC(O)[N+]([O-])=O VUZPGEIXNYGDJN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000006937 anti-inflammatory bioactivity Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003534 oscillatory effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3543021.4 | 1985-12-05 | ||
| DE19853543021 DE3543021A1 (de) | 1985-12-05 | 1985-12-05 | Verbesserte verfahren zur herstellung von d-threo-1-(p-methylsulfonylphenyl) -2-dichloracetamido-propandiol-1,3-(thiamphenicol) sowie verwendung geeigneter zwischenprodukte |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62132852A true JPS62132852A (ja) | 1987-06-16 |
Family
ID=6287716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61287879A Pending JPS62132852A (ja) | 1985-12-05 | 1986-12-04 | チアムフエニコ−ル（１）の製法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4945181A (en, 2012) |
| EP (1) | EP0224902B1 (en, 2012) |
| JP (1) | JPS62132852A (en, 2012) |
| AT (1) | ATE42094T1 (en, 2012) |
| DE (2) | DE3543021A1 (en, 2012) |
| ES (1) | ES2008668B3 (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4796258B2 (ja) * | 2000-04-11 | 2011-10-19 | ザンボン グループ エス．ピー．エー． | クラミジア・ニューモニエ感染症の治療に有用な医薬組成物を製造するためのチアムフェニコール及びその誘導体の使用 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02771A (ja) * | 1988-01-08 | 1990-01-05 | Nippon Zeon Co Ltd | チアンフェニコールの製造法 |
| US5346828A (en) * | 1991-03-27 | 1994-09-13 | Celgene Corporation | Stereoisomeric enrichment of 2-amino-3-hydroxy-3-phenylpropionic acids using d-threonine aldolase |
| EP1785414A1 (en) * | 2005-11-09 | 2007-05-16 | KRKA, tovarna zdravil, d.d., Novo mesto | Process for the synthesis of intermediates of chloramphenicol or its analogues |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA526865A (en) * | 1956-06-26 | A. Gregory Walter | Substituted sulfonylphenyl-amido-1,3-propanediols and process for preparing them | |
| GB745900A (en) * | 1951-10-01 | 1956-03-07 | Sterling Drug Inc | Acylaminodiols and method for preparing same |
| GB770277A (en) * | 1952-08-23 | 1957-03-20 | Parke Davis & Co | Amino-propanediols and their derivatives |
| US2791595A (en) * | 1953-01-14 | 1957-05-07 | Parke Davis & Co | Long chain esters of nitrophenylaminopropanediols and preparation thereof |
| US2742500A (en) * | 1953-12-22 | 1956-04-17 | Du Pont | Resolution of phenylaminopropanediols and intermediates |
| US2726266A (en) * | 1954-05-10 | 1955-12-06 | Du Pont | Antibacterial composition containing diastereoisomers of 1-(p-methylsul-fonylphenyl)-2-(alpha, alpha-dichlo-roacetamido)-1, 3-propanediol |
| CH589617A5 (en, 2012) * | 1973-11-22 | 1977-07-15 | Hoffmann La Roche | |
| US4235892A (en) * | 1979-02-05 | 1980-11-25 | Schering Corporation, Patent Dept. | 1-Aryl-2-acylamido-3-fluoro-1-propanols, methods for their use as antibacterial agents and compositions useful therefor |
| US4582918A (en) * | 1984-09-19 | 1986-04-15 | Schering Corporation | Preparation of intermediates for (threo)-1-aryl-2-acylamido-3-fluoro-1-propanols |
-
1985
- 1985-12-05 DE DE19853543021 patent/DE3543021A1/de active Granted
-
1986
- 1986-12-01 EP EP86116667A patent/EP0224902B1/de not_active Expired
- 1986-12-01 ES ES86116667T patent/ES2008668B3/es not_active Expired
- 1986-12-01 DE DE8686116667T patent/DE3662786D1/de not_active Expired
- 1986-12-01 AT AT86116667T patent/ATE42094T1/de active
- 1986-12-01 US US06/936,173 patent/US4945181A/en not_active Expired - Lifetime
- 1986-12-04 JP JP61287879A patent/JPS62132852A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4796258B2 (ja) * | 2000-04-11 | 2011-10-19 | ザンボン グループ エス．ピー．エー． | クラミジア・ニューモニエ感染症の治療に有用な医薬組成物を製造するためのチアムフェニコール及びその誘導体の使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| US4945181A (en) | 1990-07-31 |
| ATE42094T1 (de) | 1989-04-15 |
| ES2008668B3 (es) | 1989-08-01 |
| DE3543021C2 (en, 2012) | 1988-04-14 |
| EP0224902B1 (de) | 1989-04-12 |
| DE3543021A1 (de) | 1987-06-11 |
| DE3662786D1 (en) | 1989-05-18 |
| EP0224902A1 (de) | 1987-06-10 |
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