CA1087207A - Derivatives of the d-threo-1-phenyl-2-trifluoroacetamido-1,3-propanediol - Google Patents
Derivatives of the d-threo-1-phenyl-2-trifluoroacetamido-1,3-propanediolInfo
- Publication number
- CA1087207A CA1087207A CA284,228A CA284228A CA1087207A CA 1087207 A CA1087207 A CA 1087207A CA 284228 A CA284228 A CA 284228A CA 1087207 A CA1087207 A CA 1087207A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- acid
- ch3o2s
- formula
- threo
- 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
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 title claims description 16
- 229920000166 polytrimethylene carbonate Polymers 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 17
- 229960002449 glycine Drugs 0.000 claims abstract description 14
- 235000013905 glycine and its sodium salt Nutrition 0.000 claims abstract description 11
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- -1 aminoacetic acid ester Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 claims description 4
- 239000004160 Ammonium persulphate Substances 0.000 claims description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004159 Potassium persulphate Substances 0.000 claims description 3
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 3
- 235000019395 ammonium persulphate Nutrition 0.000 claims description 3
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 3
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 3
- 150000004965 peroxy acids Chemical class 0.000 claims description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 3
- 235000019394 potassium persulphate Nutrition 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 229940035437 1,3-propanediol Drugs 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 229960004011 methenamine Drugs 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 abstract description 4
- 239000004471 Glycine Substances 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 229940126572 wide-spectrum antibiotic Drugs 0.000 abstract description 2
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000194032 Enterococcus faecalis Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 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 description 2
- 229960003053 thiamphenicol Drugs 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
- IDCLTMRSSAXUNY-UHFFFAOYSA-N 5-hydroxylansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC(O)=CC=C2N1 IDCLTMRSSAXUNY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241001646716 Escherichia coli K-12 Species 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000588772 Morganella morganii Species 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- AELGFIZKISMQTG-UHFFFAOYSA-N n-(1,3-dihydroxypropan-2-yl)-2,2,2-trifluoroacetamide Chemical compound OCC(CO)NC(=O)C(F)(F)F AELGFIZKISMQTG-UHFFFAOYSA-N 0.000 description 1
- RMDOTXMZJWZIBQ-UHFFFAOYSA-N n-(1,3-dihydroxypropyl)-2,2,2-trifluoroacetamide Chemical compound OCCC(O)NC(=O)C(F)(F)F RMDOTXMZJWZIBQ-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT26042/76A IT1065143B (it) | 1976-08-05 | 1976-08-05 | Derivati del d-treo-1-fenil-2-trifluoroacetamido-1,3-propandiolo e processi per la loro preparazione |
| IT26042A/76 | 1976-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1087207A true CA1087207A (en) | 1980-10-07 |
Family
ID=11218484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA284,228A Expired CA1087207A (en) | 1976-08-05 | 1977-08-05 | Derivatives of the d-threo-1-phenyl-2-trifluoroacetamido-1,3-propanediol |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5321135A (de) |
| AT (1) | AT351018B (de) |
| AU (1) | AU509278B2 (de) |
| BE (1) | BE857543A (de) |
| CA (1) | CA1087207A (de) |
| CH (1) | CH609338A5 (de) |
| DE (1) | DE2735431A1 (de) |
| ES (1) | ES461093A1 (de) |
| FR (1) | FR2360560A1 (de) |
| GB (1) | GB1534387A (de) |
| HU (1) | HU173169B (de) |
| IE (1) | IE45460B1 (de) |
| IT (1) | IT1065143B (de) |
| NL (1) | NL7708695A (de) |
| PT (1) | PT66889B (de) |
| YU (1) | YU40678B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5977276A (ja) * | 1982-10-27 | 1984-05-02 | 松下冷機株式会社 | 製氷機 |
| EP0677511A3 (de) | 1983-06-02 | 1996-07-24 | Zambon Spa | Zwischenprodukte zur Herstellung von 1-Phenyl-1-hydroxy-2-amino-3-fluorpropan-Derivaten. |
| IT1317836B1 (it) * | 2000-02-16 | 2003-07-15 | Zambon Spa | Uso del tiamfenicolo per la preparazione di composizioni farmaceuticheutili per il trattamento di infezioni da staphylococci |
-
1976
- 1976-08-05 IT IT26042/76A patent/IT1065143B/it active
-
1977
- 1977-07-18 YU YU1779/77A patent/YU40678B/xx unknown
- 1977-07-28 ES ES461093A patent/ES461093A1/es not_active Expired
- 1977-08-04 CH CH959077A patent/CH609338A5/xx not_active IP Right Cessation
- 1977-08-04 PT PT66889A patent/PT66889B/pt unknown
- 1977-08-05 HU HU77CE1140A patent/HU173169B/hu unknown
- 1977-08-05 CA CA284,228A patent/CA1087207A/en not_active Expired
- 1977-08-05 AT AT577177A patent/AT351018B/de not_active IP Right Cessation
- 1977-08-05 GB GB32845/77A patent/GB1534387A/en not_active Expired
- 1977-08-05 FR FR7724168A patent/FR2360560A1/fr active Granted
- 1977-08-05 NL NL7708695A patent/NL7708695A/xx not_active Application Discontinuation
- 1977-08-05 DE DE19772735431 patent/DE2735431A1/de not_active Withdrawn
- 1977-08-05 AU AU27655/77A patent/AU509278B2/en not_active Expired
- 1977-08-05 JP JP9345877A patent/JPS5321135A/ja active Pending
- 1977-08-05 BE BE179956A patent/BE857543A/xx not_active IP Right Cessation
- 1977-08-05 IE IE1643/77A patent/IE45460B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU177977A (en) | 1982-10-31 |
| DE2735431A1 (de) | 1978-02-09 |
| PT66889A (en) | 1977-09-01 |
| ES461093A1 (es) | 1978-06-16 |
| IE45460L (en) | 1978-02-05 |
| FR2360560A1 (fr) | 1978-03-03 |
| AT351018B (de) | 1979-07-10 |
| NL7708695A (nl) | 1978-02-07 |
| HU173169B (hu) | 1979-03-28 |
| GB1534387A (en) | 1978-12-06 |
| FR2360560B1 (de) | 1981-02-06 |
| ATA577177A (de) | 1978-12-15 |
| PT66889B (en) | 1979-01-25 |
| IE45460B1 (en) | 1982-08-25 |
| CH609338A5 (en) | 1979-02-28 |
| YU40678B (en) | 1986-04-30 |
| AU509278B2 (en) | 1980-05-01 |
| AU2765577A (en) | 1979-02-08 |
| JPS5321135A (en) | 1978-02-27 |
| BE857543A (fr) | 1977-12-01 |
| IT1065143B (it) | 1985-02-25 |
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| FR2534588A2 (fr) | Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments |
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