CA1039276A - Process for the manufacture of n-(benzenesulfonyl)-5-0-desosaminyl-erythromycilamine derivatives - Google Patents
Process for the manufacture of n-(benzenesulfonyl)-5-0-desosaminyl-erythromycilamine derivativesInfo
- Publication number
- CA1039276A CA1039276A CA217,875A CA217875A CA1039276A CA 1039276 A CA1039276 A CA 1039276A CA 217875 A CA217875 A CA 217875A CA 1039276 A CA1039276 A CA 1039276A
- Authority
- CA
- Canada
- Prior art keywords
- benzenesulfonyl
- chloroform
- erythromycilamine
- desosaminyl
- solution
- 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
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 4
- 150000007513 acids Chemical class 0.000 claims abstract description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 4
- 239000011707 mineral Substances 0.000 claims abstract description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 44
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000002026 chloroform extract Substances 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
- 229960000443 hydrochloric acid Drugs 0.000 claims 3
- 235000011167 hydrochloric acid Nutrition 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- 235000017550 sodium carbonate Nutrition 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 235000010755 mineral Nutrition 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 abstract description 2
- 244000005700 microbiome Species 0.000 abstract 1
- 230000002195 synergetic effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- DVSDDICSXBCMQJ-UHFFFAOYSA-N diethyl 2-acetylbutanedioate Chemical compound CCOC(=O)CC(C(C)=O)C(=O)OCC DVSDDICSXBCMQJ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- YHVUVJYEERGYNU-UHFFFAOYSA-N 4',8-Di-Me ether-5,7,8-Trihydroxy-3-(4-hydroxybenzyl)-4-chromanone Natural products COC1(C)CC(O)OC(C)C1O YHVUVJYEERGYNU-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical compound O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 241000030538 Thecla Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU97/74A YU35363B (en) | 1974-01-14 | 1974-01-14 | Process for obtaining n-(benzene-sulfonyl)-5-0desosaminyl-erythromycilamine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1039276A true CA1039276A (en) | 1978-09-26 |
Family
ID=25548317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA217,875A Expired CA1039276A (en) | 1974-01-14 | 1975-01-14 | Process for the manufacture of n-(benzenesulfonyl)-5-0-desosaminyl-erythromycilamine derivatives |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3939144A (en, 2012) |
| AT (1) | AT333959B (en, 2012) |
| CA (1) | CA1039276A (en, 2012) |
| DE (1) | DE2501238C2 (en, 2012) |
| FR (1) | FR2257302B1 (en, 2012) |
| GB (1) | GB1461032A (en, 2012) |
| YU (1) | YU35363B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK139522C (da) * | 1975-04-07 | 1979-08-20 | Thomae Gmbh Dr K | Analogifremgangsmaade til fremstilling af 9-iminoalkylamino-erythromyciner eller syreadditionssalte deraf |
| US4206205A (en) * | 1977-10-03 | 1980-06-03 | Merck & Co., Inc. | Monosaccharide and aglycone derivatives of C-076 |
| US4334019A (en) * | 1980-06-12 | 1982-06-08 | Eli Lilly And Company | Process for producing de(mycinosyloxy)tylosin |
| US4321361A (en) * | 1980-06-12 | 1982-03-23 | Eli Lilly And Company | Demycinosyltylosin and process for its production |
| US5075289A (en) * | 1988-06-07 | 1991-12-24 | Abbott Laboratories | 9-r-azacyclic erythromycin antibiotics |
| IL99995A (en) * | 1990-11-21 | 1997-11-20 | Roussel Uclaf | Erythromycin derivatives, their preparation and pharmaceutical compositions containing them |
| FR2677025B1 (fr) * | 1991-05-27 | 1995-04-07 | Roussel Uclaf | Nouveaux derives descladinosyles de l'erythromycine, leur procede de preparation et leur application comme medicaments. |
| FR2680790B1 (fr) * | 1991-08-29 | 1996-10-31 | Roussel Uclaf | Nouveaux derives descladinosyles de l'erythromycine, leur procede de preparation et leur application comme medicaments. |
| US20020132782A1 (en) * | 2001-01-18 | 2002-09-19 | Zhenkun Ma | 9-amino erythromycin derivatives with antibacterial activity |
| US7582611B2 (en) | 2005-05-24 | 2009-09-01 | Pfizer Inc. | Motilide compounds |
| AU2006323175A1 (en) * | 2005-12-08 | 2007-06-14 | Pfizer, Inc. | Method for demethylating the 3'-dimethylamino group of erythromycin compounds |
| EP2104680B1 (en) | 2006-12-05 | 2013-01-09 | Bristol-Myers Squibb Company | Motilide polymorphs |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1100267A (en) * | 1966-10-14 | 1968-01-24 | Pliva Pharm & Chem Works | 9-amino-5-o-desosaminyl-3,6,11,12-tetrahydroxy-2,4,6,8,10,12-hexamethylpentadecane-13-olide and 9-amino-3,5,6,11,12-pentahydroxy-2,4,6,8,10,12-hexamethylpentadecane-13-olide |
-
1974
- 1974-01-14 YU YU97/74A patent/YU35363B/xx unknown
-
1975
- 1975-01-10 US US05/540,151 patent/US3939144A/en not_active Expired - Lifetime
- 1975-01-14 AT AT21975*#A patent/AT333959B/de not_active IP Right Cessation
- 1975-01-14 CA CA217,875A patent/CA1039276A/en not_active Expired
- 1975-01-14 GB GB155875A patent/GB1461032A/en not_active Expired
- 1975-01-14 DE DE2501238A patent/DE2501238C2/de not_active Expired
- 1975-01-14 FR FR7501033A patent/FR2257302B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1461032A (en) | 1977-01-13 |
| US3939144A (en) | 1976-02-17 |
| YU35363B (en) | 1980-12-31 |
| FR2257302A1 (en, 2012) | 1975-08-08 |
| YU9774A (en) | 1980-06-30 |
| DE2501238A1 (de) | 1975-07-17 |
| ATA21975A (de) | 1976-04-15 |
| FR2257302B1 (en, 2012) | 1978-07-21 |
| AT333959B (de) | 1976-12-27 |
| DE2501238C2 (de) | 1982-02-25 |
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