GB1577725A - Azetidinone derivatives - Google Patents
Azetidinone derivatives Download PDFInfo
- Publication number
- GB1577725A GB1577725A GB27201/76A GB2720176A GB1577725A GB 1577725 A GB1577725 A GB 1577725A GB 27201/76 A GB27201/76 A GB 27201/76A GB 2720176 A GB2720176 A GB 2720176A GB 1577725 A GB1577725 A GB 1577725A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- salt
- formula
- iii
- oxidation
- 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
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 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
- 229940049954 penicillin Drugs 0.000 claims description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 2
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 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
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical class C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000012747 synergistic agent Substances 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000002195 synergetic effect Effects 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB27201/76A GB1577725A (en) | 1976-06-30 | 1976-06-30 | Azetidinone derivatives |
| US05/800,347 US4210662A (en) | 1976-06-30 | 1977-05-25 | Side chain sulphoxide metabolites |
| FR7717835A FR2356649A1 (fr) | 1976-06-30 | 1977-06-10 | Nouveaux sulfoxydes utilisables comme agents antibacteriens |
| DE19772728097 DE2728097A1 (de) | 1976-06-30 | 1977-06-22 | Sulfoxide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
| JP7847577A JPS535195A (en) | 1976-06-30 | 1977-06-29 | Antiibacterial agent |
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 |
|---|---|
| GB1577725A true GB1577725A (en) | 1980-10-29 |
Family
ID=10255829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27201/76A Expired GB1577725A (en) | 1976-06-30 | 1976-06-30 | Azetidinone derivatives |
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 (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2134903A (en) * | 1983-02-01 | 1984-08-22 | Shionogi & Co | 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 |
Families Citing this family (7)
| 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 |
| EP0002564B1 (en) * | 1977-11-12 | 1984-06-20 | 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 |
| US4446146A (en) * | 1978-07-26 | 1984-05-01 | Beecham Group Limited | β-Lactam containing compounds, their preparation and use |
| EP0007753B1 (en) * | 1978-08-02 | 1982-08-25 | 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 |
| DE3265578D1 (en) * | 1981-05-14 | 1985-09-26 | Beecham Group Plc | Modified beta-lactam compounds |
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 (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2134903A (en) * | 1983-02-01 | 1984-08-22 | Shionogi & Co | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| US4210662A (en) | 1980-07-01 |
| FR2356649B1 (enExample) | 1980-03-07 |
| JPS535195A (en) | 1978-01-18 |
| DE2728097A1 (de) | 1978-01-12 |
| FR2356649A1 (fr) | 1978-01-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |