GB1412311A - Cephalosporin compounds and a process for the preparation thereof - Google Patents
Cephalosporin compounds and a process for the preparation thereofInfo
- Publication number
- GB1412311A GB1412311A GB934673A GB934673A GB1412311A GB 1412311 A GB1412311 A GB 1412311A GB 934673 A GB934673 A GB 934673A GB 934673 A GB934673 A GB 934673A GB 1412311 A GB1412311 A GB 1412311A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- amino
- isothiazole
- thiadiazole
- methyl
- 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
- -1 Cephalosporin compounds Chemical class 0.000 title abstract 6
- 229930186147 Cephalosporin Natural products 0.000 title abstract 4
- 229940124587 cephalosporin Drugs 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 125000003277 amino group Chemical group 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
- GFTBMBHVZZFGCK-UHFFFAOYSA-N 1,2,5-thiadiazole-3-carboxylic acid Chemical compound OC(=O)C=1C=NSN=1 GFTBMBHVZZFGCK-UHFFFAOYSA-N 0.000 abstract 1
- FGGLAFQQOCBWMY-UHFFFAOYSA-N 1,2-thiazole-3-carbonyl chloride Chemical compound ClC(=O)C=1C=CSN=1 FGGLAFQQOCBWMY-UHFFFAOYSA-N 0.000 abstract 1
- BIQMFEMMAANIFE-UHFFFAOYSA-N 1,2-thiazole-4-carbonyl chloride Chemical compound ClC(=O)C=1C=NSC=1 BIQMFEMMAANIFE-UHFFFAOYSA-N 0.000 abstract 1
- XGUISCOTZYKWFJ-UHFFFAOYSA-N 1,2-thiazole-5-carbothioic s-acid Chemical compound SC(=O)C1=CC=NS1 XGUISCOTZYKWFJ-UHFFFAOYSA-N 0.000 abstract 1
- DKCLBOAXAZZNQA-UHFFFAOYSA-N 1-methyltriazole-4-carbonyl chloride Chemical compound CN1C=C(C(Cl)=O)N=N1 DKCLBOAXAZZNQA-UHFFFAOYSA-N 0.000 abstract 1
- SBUXBHALPHVDFT-UHFFFAOYSA-N 1-methyltriazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)N=N1 SBUXBHALPHVDFT-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- XBDAGPORHYLEFF-UHFFFAOYSA-N 3-methyl-1,2-oxazole-5-carbothioic s-acid Chemical compound CC=1C=C(C(S)=O)ON=1 XBDAGPORHYLEFF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- FRTKHBIDCKIZIV-UHFFFAOYSA-M CN1N=NC(=C1)C([O-])=S.[K+] Chemical compound CN1N=NC(=C1)C([O-])=S.[K+] FRTKHBIDCKIZIV-UHFFFAOYSA-M 0.000 abstract 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 abstract 1
- QFJPJABYKXWFPV-UHFFFAOYSA-M S1N=CC(=C1)C([O-])=S.[K+] Chemical compound S1N=CC(=C1)C([O-])=S.[K+] QFJPJABYKXWFPV-UHFFFAOYSA-M 0.000 abstract 1
- BTIGARVSTIXBTQ-UHFFFAOYSA-M S1N=NC=C1C([O-])=S.[K+] Chemical compound S1N=NC=C1C([O-])=S.[K+] BTIGARVSTIXBTQ-UHFFFAOYSA-M 0.000 abstract 1
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 abstract 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000005947 deacylation reaction Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002081 enamines Chemical class 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UGIYGMMHMWKSRW-UHFFFAOYSA-M potassium 1,2-thiazole-3-carbothioate Chemical compound S1N=C(C=C1)C([O-])=S.[K+] UGIYGMMHMWKSRW-UHFFFAOYSA-M 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 230000005588 protonation Effects 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- GDPRTNRLCIICFQ-UHFFFAOYSA-N thiadiazole-5-carbonyl chloride Chemical compound ClC(=O)C1=CN=NS1 GDPRTNRLCIICFQ-UHFFFAOYSA-N 0.000 abstract 1
- BXCZJWHJYRELHY-UHFFFAOYSA-N thiadiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=NS1 BXCZJWHJYRELHY-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
-
- 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
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
-
- 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)
- Cephalosporin Compounds (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22954872A | 1972-02-25 | 1972-02-25 | |
| US22954672A | 1972-02-25 | 1972-02-25 | |
| US23003072A | 1972-02-28 | 1972-02-28 | |
| US23532372A | 1972-03-16 | 1972-03-16 | |
| US26176772A | 1972-06-12 | 1972-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1412311A true GB1412311A (en) | 1975-11-05 |
Family
ID=27539947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB934673A Expired GB1412311A (en) | 1972-02-25 | 1973-02-26 | Cephalosporin compounds and a process for the preparation thereof |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4897888A (enrdf_load_stackoverflow) |
| AU (1) | AU476271B2 (enrdf_load_stackoverflow) |
| BE (1) | BE795811A (enrdf_load_stackoverflow) |
| CA (1) | CA999292A (enrdf_load_stackoverflow) |
| CH (3) | CH602761A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2309135C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2181762B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1412311A (enrdf_load_stackoverflow) |
| NL (1) | NL7302486A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2728523C2 (de) * | 1977-06-23 | 1986-02-27 | Schering AG, 1000 Berlin und 4709 Bergkamen | 4-Methyl-1,2,3-thiadiazol-5-carbonsäure-(cyclohexylmethyl)-amid, Mittel mit herbizider und wachstumsregulatorischer Wirkung enthaltend diese Verbindung sowie Verfahren zu seiner Herstellung |
-
0
- BE BE795811D patent/BE795811A/xx not_active IP Right Cessation
-
1973
- 1973-02-13 AU AU52101/73A patent/AU476271B2/en not_active Expired
- 1973-02-16 CA CA163,930A patent/CA999292A/en not_active Expired
- 1973-02-22 CH CH956177A patent/CH602761A5/xx not_active IP Right Cessation
- 1973-02-22 CH CH253673A patent/CH601309A5/xx not_active IP Right Cessation
- 1973-02-22 NL NL7302486A patent/NL7302486A/xx not_active Application Discontinuation
- 1973-02-22 CH CH956077A patent/CH602758A5/xx not_active IP Right Cessation
- 1973-02-23 FR FR7306587A patent/FR2181762B1/fr not_active Expired
- 1973-02-23 DE DE2309135A patent/DE2309135C2/de not_active Expired
- 1973-02-23 JP JP48021377A patent/JPS4897888A/ja active Pending
- 1973-02-26 GB GB934673A patent/GB1412311A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4897888A (enrdf_load_stackoverflow) | 1973-12-13 |
| CH602761A5 (enrdf_load_stackoverflow) | 1978-07-31 |
| BE795811A (fr) | 1973-08-22 |
| DE2309135C2 (de) | 1983-03-03 |
| CA999292A (en) | 1976-11-02 |
| AU476271B2 (en) | 1976-09-16 |
| FR2181762A1 (enrdf_load_stackoverflow) | 1973-12-07 |
| DE2309135A1 (de) | 1973-09-06 |
| AU5210173A (en) | 1974-08-15 |
| CH602758A5 (enrdf_load_stackoverflow) | 1978-07-31 |
| FR2181762B1 (enrdf_load_stackoverflow) | 1976-12-03 |
| NL7302486A (enrdf_load_stackoverflow) | 1973-08-28 |
| CH601309A5 (enrdf_load_stackoverflow) | 1978-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |