SE445922B - 4"-deoxi-4"-arylglyoxamido- och -aroyltioformamido-derivat av oleandomycin och av dess estrar - Google Patents
4"-deoxi-4"-arylglyoxamido- och -aroyltioformamido-derivat av oleandomycin och av dess estrarInfo
- Publication number
- SE445922B SE445922B SE7900027A SE7900027A SE445922B SE 445922 B SE445922 B SE 445922B SE 7900027 A SE7900027 A SE 7900027A SE 7900027 A SE7900027 A SE 7900027A SE 445922 B SE445922 B SE 445922B
- Authority
- SE
- Sweden
- Prior art keywords
- oleandomycin
- deoxy
- acetyl
- oom
- uncle
- Prior art date
Links
- RZPAKFUAFGMUPI-KGIGTXTPSA-N oleandomycin Chemical class O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C RZPAKFUAFGMUPI-KGIGTXTPSA-N 0.000 title description 8
- 239000004104 Oleandomycin Substances 0.000 claims description 36
- 229960002351 oleandomycin Drugs 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
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- 150000001540 azides Chemical class 0.000 description 1
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
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- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- VTJCSBJRQLZNHE-CSMHCCOUSA-N desosamine Chemical compound C[C@@H](O)C[C@H](N(C)C)[C@@H](O)C=O VTJCSBJRQLZNHE-CSMHCCOUSA-N 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
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- 239000003937 drug carrier Substances 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
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- 125000004185 ester group Chemical group 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229960002773 hyaluronidase Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- PFDLUBNRHMFBGI-HRVFELILSA-N oleandolide Chemical compound O=C1[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@@H](C)C[C@]11OC1 PFDLUBNRHMFBGI-HRVFELILSA-N 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 101150028022 ppm1 gene Proteins 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical class 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 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/SE1979/000027 WO1980001678A1 (en) | 1979-01-02 | 1979-02-09 | Feeding device |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86689078A | 1978-01-03 | 1978-01-03 | |
| US05/952,411 US4166901A (en) | 1978-01-03 | 1978-10-23 | 4"-Deoxy-4"-arylglyoxamido- and aroylthioformamido derivatives of oleandomycin and its esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7900027L SE7900027L (sv) | 1979-07-04 |
| SE445922B true SE445922B (sv) | 1986-07-28 |
Family
ID=27127982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7900027A SE445922B (sv) | 1978-01-03 | 1979-01-02 | 4"-deoxi-4"-arylglyoxamido- och -aroyltioformamido-derivat av oleandomycin och av dess estrar |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4166901A (en, 2012) |
| JP (1) | JPS5495587A (en, 2012) |
| AR (1) | AR219363A1 (en, 2012) |
| AT (1) | AT364458B (en, 2012) |
| AU (1) | AU506520B2 (en, 2012) |
| CA (1) | CA1115697A (en, 2012) |
| CH (1) | CH642975A5 (en, 2012) |
| DE (1) | DE2900120A1 (en, 2012) |
| DK (1) | DK148421C (en, 2012) |
| ES (1) | ES476542A1 (en, 2012) |
| FI (1) | FI66879C (en, 2012) |
| FR (1) | FR2413404A1 (en, 2012) |
| GB (1) | GB2013179B (en, 2012) |
| IE (1) | IE47707B1 (en, 2012) |
| IL (1) | IL56362A (en, 2012) |
| IT (1) | IT1109926B (en, 2012) |
| LU (1) | LU80746A1 (en, 2012) |
| NL (1) | NL176076C (en, 2012) |
| PH (1) | PH14252A (en, 2012) |
| PT (1) | PT69015A (en, 2012) |
| SE (1) | SE445922B (en, 2012) |
| YU (1) | YU41139B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4336368A (en) * | 1981-04-20 | 1982-06-22 | Pfizer Inc. | 4 Deoxy-4-methylene oleandomycin and derivatives thereof |
| JPS60120895A (ja) * | 1983-12-02 | 1985-06-28 | Taisho Pharmaceut Co Ltd | ６−０−メチル−２′−０，ν−ビス（ベンジルオキシカルボニル）−ν−デメチルエリスロマイシンａの製法 |
| JPS60214796A (ja) * | 1984-04-06 | 1985-10-28 | Taisho Pharmaceut Co Ltd | ６−０−メチルエリスロマイシン類の製法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE44509B1 (en) * | 1976-03-03 | 1981-12-30 | Pfizer | Semi-synthetic oleandomycins |
| US4085119A (en) * | 1977-02-04 | 1978-04-18 | Pfizer Inc. | 4-Substituted amino derivatives of oleandomycin |
| US4090017A (en) * | 1977-02-04 | 1978-05-16 | Pfizer Inc. | 4-Deoxy-4-substituted amino derivatives of oleandomycin |
| US4098993A (en) * | 1977-07-25 | 1978-07-04 | Pfizer Inc. | Semi-synthetic 4-ureido-oleandomycin derivatives |
-
1978
- 1978-10-23 US US05/952,411 patent/US4166901A/en not_active Expired - Lifetime
- 1978-11-15 DK DK507478A patent/DK148421C/da not_active IP Right Cessation
- 1978-12-19 CH CH1295278A patent/CH642975A5/de not_active IP Right Cessation
- 1978-12-19 GB GB7849114A patent/GB2013179B/en not_active Expired
- 1978-12-27 CA CA318,610A patent/CA1115697A/en not_active Expired
- 1978-12-28 JP JP16447378A patent/JPS5495587A/ja active Granted
- 1978-12-28 YU YU3123/78A patent/YU41139B/xx unknown
- 1978-12-29 AU AU42984/78A patent/AU506520B2/en not_active Expired
-
1979
- 1979-01-02 LU LU80746A patent/LU80746A1/xx unknown
- 1979-01-02 IT IT19014/79A patent/IT1109926B/it active
- 1979-01-02 SE SE7900027A patent/SE445922B/sv not_active IP Right Cessation
- 1979-01-02 IL IL56362A patent/IL56362A/xx not_active IP Right Cessation
- 1979-01-02 PT PT197969015A patent/PT69015A/pt unknown
- 1979-01-02 ES ES476542A patent/ES476542A1/es not_active Expired
- 1979-01-02 FR FR7900015A patent/FR2413404A1/fr active Granted
- 1979-01-02 IE IE3/79A patent/IE47707B1/en not_active IP Right Cessation
- 1979-01-02 NL NLAANVRAGE7900007,A patent/NL176076C/xx not_active IP Right Cessation
- 1979-01-02 FI FI790005A patent/FI66879C/fi not_active IP Right Cessation
- 1979-01-02 AT AT0003179A patent/AT364458B/de not_active IP Right Cessation
- 1979-01-03 PH PH22011A patent/PH14252A/en unknown
- 1979-01-03 DE DE19792900120 patent/DE2900120A1/de active Granted
- 1979-01-03 AR AR275048A patent/AR219363A1/es active
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