IE37793B1 - 7-hydroxy-halophenylacetamido-3-heterocyclicthiomethyl cephalosporins - Google Patents
7-hydroxy-halophenylacetamido-3-heterocyclicthiomethyl cephalosporinsInfo
- Publication number
- IE37793B1 IE37793B1 IE969/73A IE96973A IE37793B1 IE 37793 B1 IE37793 B1 IE 37793B1 IE 969/73 A IE969/73 A IE 969/73A IE 96973 A IE96973 A IE 96973A IE 37793 B1 IE37793 B1 IE 37793B1
- Authority
- IE
- Ireland
- Prior art keywords
- amino
- fluoro
- ylthiomethyl
- cephem
- acetamido
- Prior art date
Links
- 229930186147 Cephalosporin Natural products 0.000 title abstract 4
- 229940124587 cephalosporin Drugs 0.000 title abstract 4
- 150000001780 cephalosporins Chemical class 0.000 title abstract 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 2
- 230000010933 acylation Effects 0.000 abstract 2
- 238000005917 acylation reaction Methods 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- VDWPQGQGGAOUJH-ZEPSKSRBSA-N (6R)-7-[[2-amino-2-(3-chloro-4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound ClC=1C=C(C(N)C(=O)NC2[C@@H]3N(C(=C(CS3)CSC3=NN=NN3C)C(=O)O)C2=O)C=CC=1O VDWPQGQGGAOUJH-ZEPSKSRBSA-N 0.000 abstract 1
- MYGDBAYVXQNBCO-IOJJLOCKSA-N (6r)-4-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1C=C(C(O)=O)N2C(=O)C[C@H]2S1 MYGDBAYVXQNBCO-IOJJLOCKSA-N 0.000 abstract 1
- OUYUJUJHVLCUPX-ZEPSKSRBSA-N (6r)-7-[[2-amino-2-(3-fluoro-4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)C(N)C=3C=C(F)C(O)=CC=3)[C@H]2SC1 OUYUJUJHVLCUPX-ZEPSKSRBSA-N 0.000 abstract 1
- MTEWCIRHXLXEQI-QWQCLYJRSA-N (6r)-7-[[2-amino-2-(3-fluoro-4-hydroxyphenyl)acetyl]amino]-8-oxo-3-(2h-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)NC(=O)C(N)C=2C=C(F)C(O)=CC=2)CC=1CSC=1C=NNN=1 MTEWCIRHXLXEQI-QWQCLYJRSA-N 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- TZKQRQGNHZYFKG-UHFFFAOYSA-N 2-(3-fluoro-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)C1=CC=C(O)C(F)=C1 TZKQRQGNHZYFKG-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000006073 displacement reaction Methods 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 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
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000395 magnesium oxide Substances 0.000 abstract 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- -1 t-butoxycarbonyl Chemical group 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
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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US262903A US3867380A (en) | 1971-02-18 | 1972-06-14 | 3-Heterocyclic thiomethylcephalosporins |
| US00289499A US3855213A (en) | 1971-02-18 | 1972-09-15 | 3-heterocyclic thiomethyl-cephalosporins |
| US35956773A | 1973-05-11 | 1973-05-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37793L IE37793L (en) | 1973-12-14 |
| IE37793B1 true IE37793B1 (en) | 1977-10-12 |
Family
ID=27401552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE969/73A IE37793B1 (en) | 1972-06-14 | 1973-06-12 | 7-hydroxy-halophenylacetamido-3-heterocyclicthiomethyl cephalosporins |
Country Status (10)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1035353A (en) * | 1973-01-31 | 1978-07-25 | Lee C. Cheney | 3-thiolated-7-acylamidocephalosporanic acids |
| CA1074784A (en) * | 1974-09-06 | 1980-04-01 | Sumitomo Chemical Company | N-ACYLAMINO-.alpha.-ARYLACETAMIDO CEPHALOSPORINS |
| IL49183A0 (en) * | 1975-03-27 | 1976-05-31 | Pfizer | Novel cephalosporin derivatives,their preparation and pharmaceutical compositions containing them |
| JPS5346995A (en) * | 1976-10-12 | 1978-04-27 | Sangyo Kagaku Kenkyu Kyokai | Antibacterial agents |
| WO2010087425A1 (ja) | 2009-01-30 | 2010-08-05 | 国立大学法人京都大学 | 前立腺癌の進行抑制剤および進行抑制方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641021A (en) * | 1969-04-18 | 1972-02-08 | Lilly Co Eli | 3 7-(ring-substituted) cephalosporin compounds |
-
1973
- 1973-06-11 CA CA173,707A patent/CA999574A/en not_active Expired
- 1973-06-12 GB GB2779473A patent/GB1416503A/en not_active Expired
- 1973-06-12 IE IE969/73A patent/IE37793B1/xx unknown
- 1973-06-13 CH CH852573A patent/CH585228A5/xx not_active IP Right Cessation
- 1973-06-13 NL NL7308199A patent/NL7308199A/xx not_active Application Discontinuation
- 1973-06-13 ES ES415874A patent/ES415874A1/es not_active Expired
- 1973-06-14 FR FR7321732A patent/FR2187305B1/fr not_active Expired
- 1973-06-14 DE DE2330307A patent/DE2330307C2/de not_active Expired
- 1973-06-14 JP JP48067291A patent/JPS4949984A/ja active Pending
- 1973-06-14 AU AU56952/73A patent/AU474443B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA999574A (en) | 1976-11-09 |
| CH585228A5 (enrdf_load_stackoverflow) | 1977-02-28 |
| AU474443B2 (en) | 1976-07-22 |
| DE2330307A1 (de) | 1974-01-03 |
| FR2187305A1 (enrdf_load_stackoverflow) | 1974-01-18 |
| FR2187305B1 (enrdf_load_stackoverflow) | 1976-12-03 |
| NL7308199A (enrdf_load_stackoverflow) | 1973-12-18 |
| DE2330307C2 (de) | 1983-03-10 |
| IE37793L (en) | 1973-12-14 |
| ES415874A1 (es) | 1976-02-01 |
| AU5695273A (en) | 1974-12-19 |
| JPS4949984A (enrdf_load_stackoverflow) | 1974-05-15 |
| GB1416503A (en) | 1975-12-03 |
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