IE36448B1 - New cephalosporin esters salts thereof and methods for their preparation - Google Patents
New cephalosporin esters salts thereof and methods for their preparationInfo
- Publication number
- IE36448B1 IE36448B1 IE65272A IE65272A IE36448B1 IE 36448 B1 IE36448 B1 IE 36448B1 IE 65272 A IE65272 A IE 65272A IE 65272 A IE65272 A IE 65272A IE 36448 B1 IE36448 B1 IE 36448B1
- Authority
- IE
- Ireland
- Prior art keywords
- cephalosporin
- compound
- azido
- sulphoxide
- salt
- Prior art date
Links
- -1 cephalosporin esters salts Chemical class 0.000 title abstract 21
- 229930186147 Cephalosporin Natural products 0.000 title abstract 13
- 229940124587 cephalosporin Drugs 0.000 title abstract 13
- 238000000034 method Methods 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000003277 amino group Chemical group 0.000 abstract 5
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- PJGJQVRXEUVAFT-UHFFFAOYSA-N chloroiodomethane Chemical compound ClCI PJGJQVRXEUVAFT-UHFFFAOYSA-N 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical class CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 abstract 2
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 abstract 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 238000005576 amination reaction Methods 0.000 abstract 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 2
- 150000001721 carbon Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- PEEUITQAXNZZPU-UHFFFAOYSA-N 2-azido-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)N=[N+]=[N-] PEEUITQAXNZZPU-UHFFFAOYSA-N 0.000 abstract 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 abstract 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 abstract 1
- 125000001960 7 membered carbocyclic group Chemical group 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical class CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000005035 acylthio group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 229940024606 amino acid Drugs 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 150000001768 cations Chemical group 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- YMQOUCWQGDOPJM-YFKPBYRVSA-N chloromethyl (2S)-2-azido-3-methylbutanoate Chemical compound CC(C)[C@H](N=[N+]=[N-])C(=O)OCCl YMQOUCWQGDOPJM-YFKPBYRVSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- DMRNQNYEMIDPPE-UHFFFAOYSA-M sodium 2-azido-2-methylpropanoate Chemical compound [Na+].N(=[N+]=[N-])C(C(=O)[O-])(C)C DMRNQNYEMIDPPE-UHFFFAOYSA-M 0.000 abstract 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 125000005208 trialkylammonium group Chemical group 0.000 abstract 1
- 229960004295 valine Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2944971 | 1971-06-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE36448L IE36448L (en) | 1972-12-23 |
| IE36448B1 true IE36448B1 (en) | 1976-11-10 |
Family
ID=10291750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE65272A IE36448B1 (en) | 1971-06-23 | 1972-05-15 | New cephalosporin esters salts thereof and methods for their preparation |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU457864B2 (enrdf_load_stackoverflow) |
| BE (1) | BE785275A (enrdf_load_stackoverflow) |
| DE (1) | DE2230620A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2143318B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1335317A (enrdf_load_stackoverflow) |
| IE (1) | IE36448B1 (enrdf_load_stackoverflow) |
| LU (1) | LU65565A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7208407A (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1425933A (en) * | 1972-03-13 | 1976-02-25 | Astra Laekemedel Ab | Cephalosporins |
| US5481011A (en) * | 1994-12-13 | 1996-01-02 | Bristol-Myers Squibb Company | Process for preparing N-protected amino acid α-halomethyl ketones and alcohols from N-protected amino acid esters |
| JP5324463B2 (ja) | 2006-12-10 | 2013-10-23 | チョンシー ユー | β−ラクタム抗生物質の経皮送達システム |
| US9969751B2 (en) | 2009-06-10 | 2018-05-15 | Techfields Pharma Co., Ltd. | High penetration prodrug compositions of antimicrobials and antimicrobial-related compounds |
| RU2683934C2 (ru) | 2012-01-18 | 2019-04-03 | Текфилдз Фарма Ко., Лтд. | Композиции, содержащие пролекарства с высокой проницаемостью, и фармацевтическая композиция для лечения состояний легких |
| JP5795343B2 (ja) * | 2013-01-23 | 2015-10-14 | チョンシー ユー | β−ラクタム抗生物質の経皮送達システム |
-
1971
- 1971-06-23 GB GB1335317D patent/GB1335317A/en not_active Expired
-
1972
- 1972-05-15 IE IE65272A patent/IE36448B1/xx unknown
- 1972-05-30 AU AU42874/72A patent/AU457864B2/en not_active Expired
- 1972-06-20 NL NL7208407A patent/NL7208407A/xx unknown
- 1972-06-22 LU LU65565D patent/LU65565A1/xx unknown
- 1972-06-22 BE BE785275A patent/BE785275A/xx unknown
- 1972-06-22 DE DE19722230620 patent/DE2230620A1/de active Pending
- 1972-06-22 FR FR7222623A patent/FR2143318B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU4287472A (en) | 1973-12-06 |
| DE2230620A1 (de) | 1972-12-28 |
| NL7208407A (enrdf_load_stackoverflow) | 1972-12-28 |
| IE36448L (en) | 1972-12-23 |
| LU65565A1 (enrdf_load_stackoverflow) | 1972-10-26 |
| FR2143318A1 (enrdf_load_stackoverflow) | 1973-02-02 |
| BE785275A (fr) | 1972-12-22 |
| GB1335317A (en) | 1973-10-24 |
| AU457864B2 (en) | 1975-01-22 |
| FR2143318B1 (enrdf_load_stackoverflow) | 1975-10-31 |
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