PT80095B - Sali di eritromicina con derivati dell'acido acetico procedimento per la loro preparazione e composizioni farmaceutiche che li contengono - Google Patents
Sali di eritromicina con derivati dell'acido acetico procedimento per la loro preparazione e composizioni farmaceutiche che li contengono Download PDFInfo
- Publication number
- PT80095B PT80095B PT80095A PT8009585A PT80095B PT 80095 B PT80095 B PT 80095B PT 80095 A PT80095 A PT 80095A PT 8009585 A PT8009585 A PT 8009585A PT 80095 B PT80095 B PT 80095B
- Authority
- PT
- Portugal
- Prior art keywords
- erythromycin
- preparation
- oxo
- tetrahydrothienylcarbamoyl
- acetic acid
- Prior art date
Links
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- -1 2-oxo-3-tetrahydrothienylcarbamoyl Chemical group 0.000 claims abstract description 20
- 229960003276 erythromycin Drugs 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 239000003172 expectorant agent Substances 0.000 claims abstract description 6
- 229940066491 mucolytics Drugs 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 4
- 229940088710 antibiotic agent Drugs 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229950001028 erythromycin propionate Drugs 0.000 claims description 14
- TYQXKHPOXXXCTP-CSLYCKPJSA-N erythromycin A 2'-propanoate Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)OC(=O)CC)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 TYQXKHPOXXXCTP-CSLYCKPJSA-N 0.000 claims description 13
- 230000003115 biocidal effect Effects 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- QUXYOFPORLVGFQ-UHFFFAOYSA-N [2-oxo-2-[(2-oxothiolan-3-yl)amino]ethyl]sulfanyl acetate Chemical compound C(C)(=O)OSCC(NC1C(SCC1)=O)=O QUXYOFPORLVGFQ-UHFFFAOYSA-N 0.000 claims description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 9
- 230000000510 mucolytic effect Effects 0.000 abstract description 6
- 239000013543 active substance Substances 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 210000002345 respiratory system Anatomy 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 210000003097 mucus Anatomy 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- KWVXPUXNQGRMGK-UHFFFAOYSA-N 2-[3-oxo-3-[(2-oxothiolan-3-yl)amino]propyl]sulfanylacetic acid Chemical compound OC(=O)CSCCC(=O)NC1CCSC1=O KWVXPUXNQGRMGK-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 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 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- VCKOQVVDHKESSP-UHFFFAOYSA-N [3-oxo-3-[(2-oxothiolan-3-yl)amino]propyl]sulfanyl acetate Chemical compound C(C)(=O)OSCCC(NC1C(SCC1)=O)=O VCKOQVVDHKESSP-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003979 granulating agent Substances 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
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003843 mucus production Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000000080 wetting agent 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20047/84A IT1173441B (it) | 1984-03-14 | 1984-03-14 | Sali di eritromicina con derivati dell'acido acetico,procedimento per la loro preparazione e composizioni farmaceutiche che li contengono |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT80095A PT80095A (it) | 1985-04-01 |
| PT80095B true PT80095B (it) | 1986-11-10 |
Family
ID=11163398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT80095A PT80095B (it) | 1984-03-14 | 1985-03-12 | Sali di eritromicina con derivati dell'acido acetico procedimento per la loro preparazione e composizioni farmaceutiche che li contengono |
Country Status (7)
| Country | Link |
|---|---|
| KR (1) | KR850006428A (it) |
| BE (1) | BE901917A (it) |
| DE (1) | DE3509244A1 (it) |
| ES (1) | ES541251A0 (it) |
| FR (1) | FR2561105B1 (it) |
| IT (1) | IT1173441B (it) |
| PT (1) | PT80095B (it) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1254530B (it) * | 1992-03-18 | 1995-09-25 | Derivati mercapto acetamidici | |
| IE970584A1 (en) * | 1996-08-07 | 2000-02-09 | Russinsky Ltd | A process for the production of pharmaceuticals |
| ITMI981267A1 (it) * | 1998-06-05 | 1999-12-05 | Edmond Pharma Srl | Uso di derivati dell'omocisteina per la preparazione di farmaci destinati ad inibire l'adesivita'batterica |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2519988B1 (fr) * | 1982-01-20 | 1985-06-14 | Refarmed Sa | Derives thioliques de l'erythromycine a activite therapeutique, procede de preparation et produits pharmaceutiques dans lesquels ils apparaissent |
| FR2502153A1 (fr) * | 1981-03-19 | 1982-09-24 | Rech Pharmaceutiq Medicale | Acides (2-oxo-3-tetrahydrothienylcarbamoyl)-alkylthio) acetiques, leurs sels et leurs esters, leur procede de preparation et les compositions pharmaceutiques en contenant |
-
1984
- 1984-03-14 IT IT20047/84A patent/IT1173441B/it active
-
1985
- 1985-03-12 PT PT80095A patent/PT80095B/it not_active IP Right Cessation
- 1985-03-12 BE BE0/214633A patent/BE901917A/fr not_active IP Right Cessation
- 1985-03-13 FR FR8503679A patent/FR2561105B1/fr not_active Expired
- 1985-03-14 KR KR1019850001647A patent/KR850006428A/ko not_active Withdrawn
- 1985-03-14 ES ES541251A patent/ES541251A0/es active Granted
- 1985-03-14 DE DE19853509244 patent/DE3509244A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IT8420047A0 (it) | 1984-03-14 |
| PT80095A (it) | 1985-04-01 |
| KR850006428A (ko) | 1985-10-05 |
| FR2561105B1 (fr) | 1987-08-21 |
| IT1173441B (it) | 1987-06-24 |
| ES8603507A1 (es) | 1986-01-01 |
| DE3509244A1 (de) | 1985-09-19 |
| ES541251A0 (es) | 1986-01-01 |
| FR2561105A1 (fr) | 1985-09-20 |
| BE901917A (fr) | 1985-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 19930511 |