DE2728097A1 - Sulfoxide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate - Google Patents
Sulfoxide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparateInfo
- Publication number
- DE2728097A1 DE2728097A1 DE19772728097 DE2728097A DE2728097A1 DE 2728097 A1 DE2728097 A1 DE 2728097A1 DE 19772728097 DE19772728097 DE 19772728097 DE 2728097 A DE2728097 A DE 2728097A DE 2728097 A1 DE2728097 A1 DE 2728097A1
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- compound
- salt
- formulas
- salts
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000003462 sulfoxides Chemical class 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 15
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- 229930186147 Cephalosporin Natural products 0.000 claims description 3
- 229930182555 Penicillin Natural products 0.000 claims description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 3
- 229940124587 cephalosporin Drugs 0.000 claims description 3
- 150000001780 cephalosporins Chemical class 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 229940049954 penicillin Drugs 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229920002307 Dextran Polymers 0.000 description 1
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 1
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- IBUIVNCCBFLEJL-UHFFFAOYSA-M sodium;phosphoric acid;chloride Chemical compound [Na+].[Cl-].OP(O)(O)=O IBUIVNCCBFLEJL-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB27201/76A GB1577725A (en) | 1976-06-30 | 1976-06-30 | Azetidinone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2728097A1 true DE2728097A1 (de) | 1978-01-12 |
Family
ID=10255829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772728097 Withdrawn DE2728097A1 (de) | 1976-06-30 | 1977-06-22 | Sulfoxide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4210662A (enExample) |
| JP (1) | JPS535195A (enExample) |
| DE (1) | DE2728097A1 (enExample) |
| FR (1) | FR2356649A1 (enExample) |
| GB (1) | GB1577725A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002564A1 (en) * | 1977-11-12 | 1979-06-27 | Beecham Group Plc | Derivatives of 7-oxo-1-azabicyclo(3.2.0)-hept-2-ene-2-carboxylic acid, their preparation, pharmaceutical compositions containing them and intermediates |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT68527A (en) * | 1977-09-15 | 1978-10-01 | Merck & Co Inc | Process for the preparation of o-,n-and carboxyl derivati-ves of thienamycin sulfoxide and sulfone |
| US4446146A (en) * | 1978-07-26 | 1984-05-01 | Beecham Group Limited | β-Lactam containing compounds, their preparation and use |
| DE2963580D1 (en) * | 1978-08-02 | 1982-10-21 | Beecham Group Plc | Beta-lactam antibacterial agents, a process for their preparation and pharmaceutical compositions containing them |
| AU534530B2 (en) * | 1979-02-02 | 1984-02-02 | Takeda Chemical Industries Ltd. | 5-aza-(3.2.0)-heptane derivatives |
| US4530791A (en) * | 1979-04-16 | 1985-07-23 | Kowa Co., Ltd. | β-Lactam antibiotics |
| EP0067518B1 (en) * | 1981-05-14 | 1985-08-21 | Beecham Group Plc | Modified beta-lactam compounds |
| US4647408A (en) * | 1983-02-01 | 1987-03-03 | Shionogi & Co., Ltd. | Carbapenem-type antibiotics |
| RU2146172C1 (ru) * | 1999-07-29 | 2000-03-10 | Институт катализа им.Г.К.Борескова СО РАН | Каталитическая композиция, способ ее приготовления и способ очистки терефталевой кислоты |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000129A (en) * | 1970-02-18 | 1976-12-28 | Koninklijke Nederlandsche Gist-En Spiritusfabriek N.V. | 6-aminopenicillanic acid sulfoxide silyl esters |
| US3928569A (en) * | 1972-08-09 | 1975-12-23 | Microbial Chem Res Found | Two substances inhibiting beta-lactamase and their production |
| CA1061779A (en) * | 1974-08-29 | 1979-09-04 | Toshiyasu Ishimaru | Cephalosporin esters |
| US3950357A (en) * | 1974-11-25 | 1976-04-13 | Merck & Co., Inc. | Antibiotics |
| NL7702183A (nl) * | 1976-03-16 | 1977-09-20 | Merck & Co Inc | Werkwijze voor het bereiden van nieuwe antibiotica. |
| US4123547A (en) * | 1977-08-04 | 1978-10-31 | Merck & Co., Inc. | Thienamycin sulfoxide and sulphone |
| US4150145A (en) * | 1977-09-15 | 1979-04-17 | Merck & Co., Inc. | N-alkylated derivatives of thienamycin sulfoxide and sulfone |
-
1976
- 1976-06-30 GB GB27201/76A patent/GB1577725A/en not_active Expired
-
1977
- 1977-05-25 US US05/800,347 patent/US4210662A/en not_active Expired - Lifetime
- 1977-06-10 FR FR7717835A patent/FR2356649A1/fr active Granted
- 1977-06-22 DE DE19772728097 patent/DE2728097A1/de not_active Withdrawn
- 1977-06-29 JP JP7847577A patent/JPS535195A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002564A1 (en) * | 1977-11-12 | 1979-06-27 | Beecham Group Plc | Derivatives of 7-oxo-1-azabicyclo(3.2.0)-hept-2-ene-2-carboxylic acid, their preparation, pharmaceutical compositions containing them and intermediates |
Also Published As
| Publication number | Publication date |
|---|---|
| US4210662A (en) | 1980-07-01 |
| JPS535195A (en) | 1978-01-18 |
| FR2356649B1 (enExample) | 1980-03-07 |
| FR2356649A1 (fr) | 1978-01-27 |
| GB1577725A (en) | 1980-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: JUNG, E., DIPL.-CHEM. DR.PHIL. SCHIRDEWAHN, J., DI |
|
| 8141 | Disposal/no request for examination |