GB1412721A - Antibacterial agents and processes for their preparation - Google Patents
Antibacterial agents and processes for their preparationInfo
- Publication number
- GB1412721A GB1412721A GB4096273A GB4096273A GB1412721A GB 1412721 A GB1412721 A GB 1412721A GB 4096273 A GB4096273 A GB 4096273A GB 4096273 A GB4096273 A GB 4096273A GB 1412721 A GB1412721 A GB 1412721A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- ylaminomethyl
- compound
- formula
- carbomethoxypropen
- 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
- 239000003242 anti bacterial agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 4
- YICPBKWYZXFJNB-UHFFFAOYSA-N 3-chloro-1h-pyridazin-6-one Chemical compound OC1=CC=C(Cl)N=N1 YICPBKWYZXFJNB-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- WMUZDBZPDLHUMW-UHFFFAOYSA-N (2-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1[N+]([O-])=O WMUZDBZPDLHUMW-UHFFFAOYSA-N 0.000 abstract 1
- QLHZKPQKYARBGT-UHFFFAOYSA-N 2-(2-cyanophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1C#N QLHZKPQKYARBGT-UHFFFAOYSA-N 0.000 abstract 1
- FEULZCSWZZYMKQ-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-hydroxyphenyl]acetic acid Chemical compound NCC1=CC(O)=CC=C1CC(O)=O FEULZCSWZZYMKQ-UHFFFAOYSA-N 0.000 abstract 1
- WBSLLIVJKKGUTM-UHFFFAOYSA-N 2-[2-(aminomethyl)-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C(CN)=C1 WBSLLIVJKKGUTM-UHFFFAOYSA-N 0.000 abstract 1
- KVHOGDSCPNRSLD-UHFFFAOYSA-N 2-[2-(azidomethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CN=[N+]=[N-] KVHOGDSCPNRSLD-UHFFFAOYSA-N 0.000 abstract 1
- CGPQRFCFBISLKF-UHFFFAOYSA-N 2-[2-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]acetic acid Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC=C1CC(O)=O CGPQRFCFBISLKF-UHFFFAOYSA-N 0.000 abstract 1
- YSQMCCYRADIHGQ-UHFFFAOYSA-N 2-[4-hydroxy-2-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]acetic acid Chemical compound CC(C)(C)OC(=O)NCC1=CC(O)=CC=C1CC(O)=O YSQMCCYRADIHGQ-UHFFFAOYSA-N 0.000 abstract 1
- PXQZTHWKWRIQSO-UHFFFAOYSA-N 2-[6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-4,6-dinitrocyclohexa-2,4-dien-1-yl]acetic acid Chemical compound CC(C)(C)OC(=O)NCC1(C=C(C=CC1CC(=O)O)[N+](=O)[O-])[N+](=O)[O-] PXQZTHWKWRIQSO-UHFFFAOYSA-N 0.000 abstract 1
- GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 abstract 1
- SRYILVFXQKHDGZ-UHFFFAOYSA-N 6-sulfanylidene-1,2-dihydropyridazin-3-one Chemical compound OC1=CC=C(S)N=N1 SRYILVFXQKHDGZ-UHFFFAOYSA-N 0.000 abstract 1
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 1
- OMFPMSBRJNYKCE-UHFFFAOYSA-N C(C)(=O)OC1=C(C=C(C=C1)O)CNC(=CC(=O)OC)C.[K] Chemical compound C(C)(=O)OC1=C(C=C(C=C1)O)CNC(=CC(=O)OC)C.[K] OMFPMSBRJNYKCE-UHFFFAOYSA-N 0.000 abstract 1
- SZZDHCWVBSPXKK-UHFFFAOYSA-M C(C)OC(=O)C(NC(=C)C)C1=C(C=CC=C1)CC(=S)[O-].[Na+] Chemical compound C(C)OC(=O)C(NC(=C)C)C1=C(C=CC=C1)CC(=S)[O-].[Na+] SZZDHCWVBSPXKK-UHFFFAOYSA-M 0.000 abstract 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- SREHTNKKTKQWOH-UHFFFAOYSA-N Cl.NCC1=C(C=CC=C1)CC(=O)O.[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])C(C(=O)O)C1=C(C=CC=C1)NC(=O)OC(C)(C)C Chemical compound Cl.NCC1=C(C=CC=C1)CC(=O)O.[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])C(C(=O)O)C1=C(C=CC=C1)NC(=O)OC(C)(C)C SREHTNKKTKQWOH-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- -1 cephalosporin compounds Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- HBMCQTHGYMTCOF-UHFFFAOYSA-N hydroquinone monoacetate Natural products CC(=O)OC1=CC=C(O)C=C1 HBMCQTHGYMTCOF-UHFFFAOYSA-N 0.000 abstract 1
- UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical compound C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- BRAHRRYCGOLXPW-UHFFFAOYSA-N methyl 2-[2-(bromomethyl)phenyl]acetate Chemical compound COC(=O)CC1=CC=CC=C1CBr BRAHRRYCGOLXPW-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- YVRNJWNSNHAEHJ-UHFFFAOYSA-M potassium 2-[2-[[(4-methoxy-4-oxobut-2-en-2-yl)amino]methyl]phenyl]ethanethioate Chemical compound C(=O)(OC)C=C(C)NCC1=C(C=CC=C1)CC(=S)[O-].[K+] YVRNJWNSNHAEHJ-UHFFFAOYSA-M 0.000 abstract 1
- JYXAWTDHRHNTNK-UHFFFAOYSA-M potassium;2-[2-[[(4-methoxy-4-oxobut-2-en-2-yl)amino]methyl]phenyl]acetate Chemical compound [K+].COC(=O)C=C(C)NCC1=CC=CC=C1CC([O-])=O JYXAWTDHRHNTNK-UHFFFAOYSA-M 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- ULWITEWBVPNPOO-UHFFFAOYSA-M sodium 2-[2-[2-ethoxy-2-oxo-1-(prop-1-en-2-ylamino)ethyl]phenyl]acetate Chemical compound C(C)OC(=O)C(NC(=C)C)C1=C(C=CC=C1)CC(=O)[O-].[Na+] ULWITEWBVPNPOO-UHFFFAOYSA-M 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 abstract 1
- 150000003573 thiols Chemical class 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
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00285764A US3813376A (en) | 1972-08-31 | 1972-08-31 | 7-(o-aminomethylphenyl-acetamido)-3-(3-hydroxypyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acid |
| US00286630A US3813390A (en) | 1972-09-06 | 1972-09-06 | 7-(o-aminomethylphenylthioacetamido)-3-(3-hydroxypyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acid |
| US00286792A US3823141A (en) | 1972-09-06 | 1972-09-06 | 7-(o-aminomethyl-p-hydroxy-phenylacetamido)-3-(3-hydroxy-pyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1412721A true GB1412721A (en) | 1975-11-05 |
Family
ID=27403558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4096273A Expired GB1412721A (en) | 1972-08-31 | 1973-08-30 | Antibacterial agents and processes for their preparation |
Country Status (10)
-
1973
- 1973-08-28 DK DK472373A patent/DK145465C/da active
- 1973-08-28 SE SE7311703A patent/SE415980B/xx unknown
- 1973-08-28 FI FI2677/73A patent/FI57420C/fi active
- 1973-08-29 AU AU59742/73A patent/AU476592B2/en not_active Expired
- 1973-08-30 JP JP48096730A patent/JPS5930716B2/ja not_active Expired
- 1973-08-30 ES ES418328A patent/ES418328A1/es not_active Expired
- 1973-08-30 GB GB4096273A patent/GB1412721A/en not_active Expired
- 1973-08-31 NL NL7312062A patent/NL7312062A/xx not_active Application Discontinuation
- 1973-08-31 FR FR7331617A patent/FR2279408A1/fr active Granted
- 1973-08-31 DE DE19732344095 patent/DE2344095A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4992091A (enrdf_load_html_response) | 1974-09-03 |
| ES418328A1 (es) | 1976-09-01 |
| AU5974273A (en) | 1975-03-06 |
| NL7312062A (enrdf_load_html_response) | 1974-03-04 |
| FR2279408B1 (enrdf_load_html_response) | 1978-07-28 |
| FR2279408A1 (fr) | 1976-02-20 |
| DE2344095A1 (de) | 1974-04-18 |
| FI57420B (fi) | 1980-04-30 |
| DK145465C (da) | 1983-04-18 |
| SE415980B (sv) | 1980-11-17 |
| DK145465B (da) | 1982-11-22 |
| AU476592B2 (en) | 1976-09-30 |
| FI57420C (fi) | 1980-08-11 |
| JPS5930716B2 (ja) | 1984-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |