SE446340B - Sett att framstella halvsyntetiska 4"-sulfonylamino-oleandomycinderivat - Google Patents
Sett att framstella halvsyntetiska 4"-sulfonylamino-oleandomycinderivatInfo
- Publication number
- SE446340B SE446340B SE7804080A SE7804080A SE446340B SE 446340 B SE446340 B SE 446340B SE 7804080 A SE7804080 A SE 7804080A SE 7804080 A SE7804080 A SE 7804080A SE 446340 B SE446340 B SE 446340B
- Authority
- SE
- Sweden
- Prior art keywords
- deoxy
- oleandomycin
- acetyl
- amino
- mmol
- Prior art date
Links
- -1 1,1,1-trifluoroethyl Chemical group 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
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- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
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- 239000004104 Oleandomycin Substances 0.000 description 83
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- 239000000047 product Substances 0.000 description 45
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- RZPAKFUAFGMUPI-UHFFFAOYSA-N Oleandomycin Natural products O1C(C)C(O)C(OC)CC1OC1C(C)C(=O)OC(C)C(C)C(O)C(C)C(=O)C2(OC2)CC(C)C(OC2C(C(CC(C)O2)N(C)C)O)C1C RZPAKFUAFGMUPI-UHFFFAOYSA-N 0.000 description 36
- 235000019367 oleandomycin Nutrition 0.000 description 36
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- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 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
- 239000012458 free base Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229960002773 hyaluronidase Drugs 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001802 infusion Methods 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
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- YPPVMLHOORADOQ-UHFFFAOYSA-N methyl 5-chlorosulfonyl-1h-pyrrole-2-carboxylate Chemical compound COC(=O)C1=CC=C(S(Cl)(=O)=O)N1 YPPVMLHOORADOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- 239000002798 polar solvent Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 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
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 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
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US79585077A | 1977-05-11 | 1977-05-11 | |
US05/883,608 US4136253A (en) | 1977-05-11 | 1978-03-06 | Semi-synthetic 4"-sulfonylamino-oleandomycin derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
SE7804080L SE7804080L (sv) | 1978-11-12 |
SE446340B true SE446340B (sv) | 1986-09-01 |
Family
ID=27121658
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE7804080A SE446340B (sv) | 1977-05-11 | 1978-04-11 | Sett att framstella halvsyntetiska 4"-sulfonylamino-oleandomycinderivat |
Country Status (31)
Country | Link |
---|---|
JP (1) | JPS53149990A (cs) |
AR (1) | AR219529A1 (cs) |
AT (1) | AT357263B (cs) |
AU (1) | AU500587B1 (cs) |
CA (1) | CA1098123A (cs) |
CH (1) | CH631461A5 (cs) |
CS (1) | CS199728B2 (cs) |
DD (1) | DD135907A5 (cs) |
DE (1) | DE2820411C2 (cs) |
DK (1) | DK148845C (cs) |
EG (1) | EG13371A (cs) |
ES (1) | ES469648A1 (cs) |
FI (1) | FI67709C (cs) |
FR (1) | FR2390453A1 (cs) |
GB (1) | GB1590162A (cs) |
GR (1) | GR70056B (cs) |
HU (1) | HU180279B (cs) |
IE (1) | IE46839B1 (cs) |
IL (1) | IL54688A (cs) |
IT (1) | IT1094816B (cs) |
LU (1) | LU79638A1 (cs) |
NL (1) | NL174254C (cs) |
NO (1) | NO145384C (cs) |
NZ (1) | NZ187229A (cs) |
PH (1) | PH15382A (cs) |
PL (1) | PL111988B1 (cs) |
PT (1) | PT68019B (cs) |
RO (1) | RO75819A (cs) |
SE (1) | SE446340B (cs) |
SU (1) | SU860707A1 (cs) |
YU (1) | YU40963B (cs) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4124755A (en) * | 1978-01-03 | 1978-11-07 | Pfizer Inc. | 11-Alkanoyl-4"-deoxy-4"-isonitrilo-oleandomycin derivatives |
US4133950A (en) * | 1978-01-03 | 1979-01-09 | Pfizer Inc. | 4"-Deoxy-4"-carbamate and dithiocarbamate derivatives of oleandomycin and its esters |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3836519A (en) * | 1973-05-04 | 1974-09-17 | Abbott Lab | Sulfonyl derivatives of erythromycin |
-
1978
- 1978-04-11 SE SE7804080A patent/SE446340B/sv not_active IP Right Cessation
- 1978-04-24 AU AU35379/78A patent/AU500587B1/en not_active Expired
- 1978-04-25 PH PH21053A patent/PH15382A/en unknown
- 1978-05-05 CS CS782903A patent/CS199728B2/cs unknown
- 1978-05-05 YU YU1082/78A patent/YU40963B/xx unknown
- 1978-05-09 GB GB18353/78A patent/GB1590162A/en not_active Expired
- 1978-05-09 CA CA302,902A patent/CA1098123A/en not_active Expired
- 1978-05-09 PT PT68019A patent/PT68019B/pt unknown
- 1978-05-10 HU HU78PI623A patent/HU180279B/hu unknown
- 1978-05-10 DE DE2820411A patent/DE2820411C2/de not_active Expired
- 1978-05-10 NZ NZ187229A patent/NZ187229A/xx unknown
- 1978-05-10 NL NLAANVRAGE7805007,A patent/NL174254C/xx not_active IP Right Cessation
- 1978-05-10 JP JP5540578A patent/JPS53149990A/ja active Granted
- 1978-05-10 CH CH508978A patent/CH631461A5/fr not_active IP Right Cessation
- 1978-05-10 NO NO781656A patent/NO145384C/no unknown
- 1978-05-10 IL IL54688A patent/IL54688A/xx unknown
- 1978-05-10 LU LU79638A patent/LU79638A1/xx unknown
- 1978-05-10 IT IT23229/78A patent/IT1094816B/it active
- 1978-05-10 FR FR7813918A patent/FR2390453A1/fr active Granted
- 1978-05-10 DK DK205878A patent/DK148845C/da not_active IP Right Cessation
- 1978-05-10 FI FI781478A patent/FI67709C/fi not_active IP Right Cessation
- 1978-05-10 AT AT338978A patent/AT357263B/de not_active IP Right Cessation
- 1978-05-10 EG EG301/78A patent/EG13371A/xx active
- 1978-05-10 IE IE953/78A patent/IE46839B1/en unknown
- 1978-05-10 PL PL1978206687A patent/PL111988B1/pl unknown
- 1978-05-10 ES ES469648A patent/ES469648A1/es not_active Expired
- 1978-05-10 GR GR56192A patent/GR70056B/el unknown
- 1978-05-10 RO RO7894029A patent/RO75819A/ro unknown
- 1978-05-10 SU SU782616147A patent/SU860707A1/ru active
- 1978-05-11 DD DD78205329A patent/DD135907A5/xx unknown
- 1978-05-11 AR AR272125A patent/AR219529A1/es active
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