GB1427211A - P-hydroxymethylphenylacetamido-cephalosporins - Google Patents
P-hydroxymethylphenylacetamido-cephalosporinsInfo
- Publication number
- GB1427211A GB1427211A GB2779573A GB2779573A GB1427211A GB 1427211 A GB1427211 A GB 1427211A GB 2779573 A GB2779573 A GB 2779573A GB 2779573 A GB2779573 A GB 2779573A GB 1427211 A GB1427211 A GB 1427211A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- hydroxymethylphenylacetamido
- ylthiomethyl
- cephem
- formula
- 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
- 229940124587 cephalosporin Drugs 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229930186147 Cephalosporin Natural products 0.000 abstract 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract 2
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 abstract 2
- 150000001780 cephalosporins Chemical class 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- KWNSHEVEPIKTCJ-QWQCLYJRSA-N (6R)-7-[[2-amino-2-[4-(hydroxymethyl)phenyl]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 NC(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)O)C1=O)C1=CC=C(C=C1)CO KWNSHEVEPIKTCJ-QWQCLYJRSA-N 0.000 abstract 1
- PGXVPMPTIYUZQH-WTNGLUPJSA-N (6R)-7-[[2-amino-2-[4-(hydroxymethyl)phenyl]acetyl]amino]-3-[(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 NC(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC=2SC(=NN=2)C)C(=O)O)C1=O)C1=CC=C(C=C1)CO PGXVPMPTIYUZQH-WTNGLUPJSA-N 0.000 abstract 1
- GOUZKJYCJYJVCL-WTNGLUPJSA-N (6r)-7-[[2-amino-2-[4-(hydroxymethyl)phenyl]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=CC(CO)=CC=2)CC=1CSC=1C=NNN=1 GOUZKJYCJYJVCL-WTNGLUPJSA-N 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
- IVQDNDSBHMVGLM-UHFFFAOYSA-N 2-amino-2-[4-(hydroxymethyl)phenyl]acetic acid Chemical compound OC(=O)C(N)C1=CC=C(CO)C=C1 IVQDNDSBHMVGLM-UHFFFAOYSA-N 0.000 abstract 1
- -1 acetoxy, methoxy, methylthio Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- 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
-
- 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
-
- 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)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
| US359566A US3891634A (en) | 1970-12-17 | 1973-05-11 | P-Hydroxymethylphenylacetamidocephalosporins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1427211A true GB1427211A (en) | 1976-03-10 |
Family
ID=27401551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2779573A Expired GB1427211A (en) | 1972-06-14 | 1973-06-12 | P-hydroxymethylphenylacetamido-cephalosporins |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4949983A (enrdf_load_stackoverflow) |
| AU (1) | AU470357B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1003405A (enrdf_load_stackoverflow) |
| DE (1) | DE2330296A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2187306B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1427211A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1074784A (en) * | 1974-09-06 | 1980-04-01 | Sumitomo Chemical Company | N-ACYLAMINO-.alpha.-ARYLACETAMIDO CEPHALOSPORINS |
| JPH01157988A (ja) * | 1987-12-12 | 1989-06-21 | Microbial Chem Res Found | 経口用セフアロスポリン優導体 |
| GB9325360D0 (en) * | 1993-12-10 | 1994-02-16 | Univ Bristol | Organic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1524225A (fr) * | 1966-09-14 | 1968-05-10 | Lilly Co Eli | Procédé de préparation d'analogues à la 7-alpha-aminobenzyl-3-méthyl céphalosporine |
-
1973
- 1973-06-11 CA CA173,745A patent/CA1003405A/en not_active Expired
- 1973-06-12 GB GB2779573A patent/GB1427211A/en not_active Expired
- 1973-06-14 JP JP48067290A patent/JPS4949983A/ja active Pending
- 1973-06-14 FR FR7321733A patent/FR2187306B1/fr not_active Expired
- 1973-06-14 AU AU56951/73A patent/AU470357B2/en not_active Expired
- 1973-06-14 DE DE2330296A patent/DE2330296A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU5695173A (en) | 1974-12-19 |
| FR2187306B1 (enrdf_load_stackoverflow) | 1976-12-31 |
| AU470357B2 (en) | 1976-03-11 |
| CA1003405A (en) | 1977-01-11 |
| JPS4949983A (enrdf_load_stackoverflow) | 1974-05-15 |
| FR2187306A1 (enrdf_load_stackoverflow) | 1974-01-18 |
| DE2330296A1 (de) | 1974-01-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |