GB1295841A - - Google Patents
Info
- Publication number
- GB1295841A GB1295841A GB1295841DA GB1295841A GB 1295841 A GB1295841 A GB 1295841A GB 1295841D A GB1295841D A GB 1295841DA GB 1295841 A GB1295841 A GB 1295841A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thiadiazolyl
- tetrazolyl
- prepared
- thiol
- esters
- 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 1H-tetrazolyl Chemical group 0.000 abstract 10
- 125000001113 thiadiazolyl group Chemical group 0.000 abstract 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 6
- 229930186147 Cephalosporin Natural products 0.000 abstract 5
- 229940124587 cephalosporin Drugs 0.000 abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000001715 oxadiazolyl group Chemical group 0.000 abstract 3
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001780 cephalosporins Chemical class 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- MLYYVTUWGNIJIB-FFFFSGIJSA-N (6r)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-FFFFSGIJSA-N 0.000 abstract 1
- AIPGVDXAMMEYPD-UHFFFAOYSA-N 1-(1-methoxypropyl)-2H-tetrazole-5-thione Chemical compound COC(CC)N1N=NN=C1S AIPGVDXAMMEYPD-UHFFFAOYSA-N 0.000 abstract 1
- MYTWYPWDKHLWED-UHFFFAOYSA-N 2-(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)acetic acid Chemical compound OC(=O)CC1=NN=C(S)S1 MYTWYPWDKHLWED-UHFFFAOYSA-N 0.000 abstract 1
- QPBTXSMHGRULPT-UHFFFAOYSA-N 5-[(dimethylazaniumyl)methyl]-1,3,4-oxadiazole-2-thiolate Chemical compound CN(C)CC1=NNC(=S)O1 QPBTXSMHGRULPT-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- LFPNOWWZGJPVSY-UHFFFAOYSA-N N-(3-methoxypropyl)-2-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)acetamide Chemical compound COCCCNC(=O)CC1=NN=C(S1)S LFPNOWWZGJPVSY-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical compound NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 abstract 1
- 125000002720 diazolyl group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- JLORMGPIXBJSIY-UHFFFAOYSA-N ethyl 2-(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)acetate Chemical compound CCOC(=O)CC1=NN=C(S)S1 JLORMGPIXBJSIY-UHFFFAOYSA-N 0.000 abstract 1
- QEZGROMHDDHBPR-UHFFFAOYSA-N ethyl 3-ethylsulfanyl-3-sulfanylidenepropanoate Chemical compound CCOC(=O)CC(=S)SCC QEZGROMHDDHBPR-UHFFFAOYSA-N 0.000 abstract 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 abstract 1
- 238000004108 freeze drying Methods 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 150000004686 pentahydrates Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
- 238000001291 vacuum drying Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5261669 | 1969-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1295841A true GB1295841A (enrdf_load_stackoverflow) | 1972-11-08 |
Family
ID=10464610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1295841D Expired GB1295841A (enrdf_load_stackoverflow) | 1969-10-27 | 1969-10-27 |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1295841A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50142587A (enrdf_load_stackoverflow) * | 1974-04-26 | 1975-11-17 | ||
| US6642020B2 (en) | 2001-04-19 | 2003-11-04 | Bioferma Murcia S.A. | Process for preparing cephalosporin derivatives |
-
1969
- 1969-10-27 GB GB1295841D patent/GB1295841A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50142587A (enrdf_load_stackoverflow) * | 1974-04-26 | 1975-11-17 | ||
| US6642020B2 (en) | 2001-04-19 | 2003-11-04 | Bioferma Murcia S.A. | Process for preparing cephalosporin derivatives |
| US6730497B2 (en) | 2001-04-19 | 2004-05-04 | Bioferma Murcia S.A. | Process for preparing cephalosporanic acid derivatives using β-ketoacid derivatives |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |