GB1424373A - 7-azido-cephalosporin compounds and their preparation - Google Patents
7-azido-cephalosporin compounds and their preparationInfo
- Publication number
- GB1424373A GB1424373A GB1705073A GB1705073A GB1424373A GB 1424373 A GB1424373 A GB 1424373A GB 1705073 A GB1705073 A GB 1705073A GB 1705073 A GB1705073 A GB 1705073A GB 1424373 A GB1424373 A GB 1424373A
- Authority
- GB
- United Kingdom
- Prior art keywords
- azido
- acid
- reacted
- reaction
- ester
- 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
- 238000002360 preparation method Methods 0.000 title abstract 2
- -1 carbamoyloxy Chemical group 0.000 abstract 7
- 238000006243 chemical reaction Methods 0.000 abstract 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 239000000543 intermediate Substances 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 abstract 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-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
- IOVQBHMSPTUQAQ-UHFFFAOYSA-N 2-azido-2-methoxyacetic acid Chemical compound COC(C(O)=O)N=[N+]=[N-] IOVQBHMSPTUQAQ-UHFFFAOYSA-N 0.000 abstract 1
- HWPXTDXPHUUFID-UHFFFAOYSA-N 2-azido-2-methoxyacetyl chloride Chemical compound COC(C(Cl)=O)N=[N+]=[N-] HWPXTDXPHUUFID-UHFFFAOYSA-N 0.000 abstract 1
- PPXUUPXQWDQNGO-UHFFFAOYSA-N 2-azidoacetic acid Chemical compound OC(=O)CN=[N+]=[N-] PPXUUPXQWDQNGO-UHFFFAOYSA-N 0.000 abstract 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 abstract 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 abstract 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002262 Schiff base Substances 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- JNKVFSFFZPJLMW-UHFFFAOYSA-N methyl 2-azido-2-methoxyacetate Chemical compound [N-]=[N+]=NC(OC)C(=O)OC JNKVFSFFZPJLMW-UHFFFAOYSA-N 0.000 abstract 1
- DCOWHZYIFORKFC-UHFFFAOYSA-N methyl 2-chloro-2-methoxyacetate Chemical compound COC(Cl)C(=O)OC DCOWHZYIFORKFC-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- KTKAAPWVXFAGIT-UHFFFAOYSA-N methylsulfonyl 2-azidoacetate Chemical compound CS(=O)(=O)OC(=O)CN=[N+]=[N-] KTKAAPWVXFAGIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 150000002900 organolithium compounds Chemical class 0.000 abstract 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- ULUATRKSGFEGOE-UHFFFAOYSA-N prop-1-en-2-yl 2-azidoacetate Chemical compound CC(=C)OC(=O)CN=[N+]=[N-] ULUATRKSGFEGOE-UHFFFAOYSA-N 0.000 abstract 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 abstract 1
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- QTXBEQGZSJCCAU-UHFFFAOYSA-N trifluoromethylsulfonyl 2-azidoacetate Chemical compound FC(F)(F)S(=O)(=O)OC(=O)CN=[N+]=[N-] QTXBEQGZSJCCAU-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- 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
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24427172A | 1972-04-14 | 1972-04-14 | |
| US26784572A | 1972-06-30 | 1972-06-30 | |
| US26784672A | 1972-06-30 | 1972-06-30 | |
| US29635672A | 1972-10-10 | 1972-10-10 | |
| US05/336,561 US3962224A (en) | 1972-10-10 | 1973-03-05 | Cephalosporin compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1424373A true GB1424373A (en) | 1976-02-11 |
Family
ID=27540192
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1705073A Expired GB1424373A (en) | 1972-04-14 | 1973-04-10 | 7-azido-cephalosporin compounds and their preparation |
| GB596475A Expired GB1424375A (en) | 1972-04-14 | 1973-04-10 | Dl-cephalosporin derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB596475A Expired GB1424375A (en) | 1972-04-14 | 1973-04-10 | Dl-cephalosporin derivatives |
Country Status (10)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2300856A (en) * | 1995-05-16 | 1996-11-20 | Pfizer Ltd | Beta-lactam preparation |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3947413A (en) * | 1972-11-13 | 1976-03-30 | Merck & Co., Inc. | 3-α-Substituted cephalosporins |
-
1973
- 1973-04-05 NL NL7304755A patent/NL7304755A/xx not_active Application Discontinuation
- 1973-04-09 IL IL41986A patent/IL41986A/en unknown
- 1973-04-10 GB GB1705073A patent/GB1424373A/en not_active Expired
- 1973-04-10 GB GB596475A patent/GB1424375A/en not_active Expired
- 1973-04-10 IE IE562/73A patent/IE37510B1/xx unknown
- 1973-04-11 CH CH525173A patent/CH599220A5/xx not_active IP Right Cessation
- 1973-04-11 FR FR7313062A patent/FR2182953B1/fr not_active Expired
- 1973-04-13 DE DE2365406*A patent/DE2365406A1/de not_active Ceased
- 1973-04-13 DE DE2365582A patent/DE2365582C2/de not_active Expired
- 1973-04-13 DD DD179575*A patent/DD112272A5/xx unknown
- 1973-04-13 DD DD179995*A patent/DD112455A5/xx unknown
- 1973-04-13 DD DD170170A patent/DD107053A5/xx unknown
- 1973-04-13 DE DE2365456*A patent/DE2365456A1/de not_active Ceased
- 1973-04-14 JP JP4184973A patent/JPS5538957B2/ja not_active Expired
-
1975
- 1975-11-19 SE SE7513005A patent/SE7513005L/xx unknown
- 1975-11-19 SE SE7513006A patent/SE7513006L/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2300856A (en) * | 1995-05-16 | 1996-11-20 | Pfizer Ltd | Beta-lactam preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2365582C2 (de) | 1982-03-25 |
| IE37510B1 (en) | 1977-08-03 |
| DE2318829A1 (de) | 1973-10-31 |
| IL41986A0 (en) | 1973-06-29 |
| JPS4914488A (enrdf_load_stackoverflow) | 1974-02-07 |
| DE2365456A1 (de) | 1975-02-20 |
| DD107053A5 (enrdf_load_stackoverflow) | 1974-07-12 |
| NL7304755A (enrdf_load_stackoverflow) | 1973-10-16 |
| SE7513005L (sv) | 1975-11-19 |
| SE7513006L (sv) | 1975-11-19 |
| IE37510L (en) | 1973-10-14 |
| DD112272A5 (enrdf_load_stackoverflow) | 1975-04-05 |
| IL41986A (en) | 1976-12-31 |
| DE2365406A1 (de) | 1975-01-23 |
| FR2182953A1 (enrdf_load_stackoverflow) | 1973-12-14 |
| JPS5538957B2 (enrdf_load_stackoverflow) | 1980-10-07 |
| DE2365582A1 (de) | 1975-06-26 |
| DE2318829B2 (de) | 1976-01-02 |
| CH599220A5 (enrdf_load_stackoverflow) | 1978-05-12 |
| DD112455A5 (enrdf_load_stackoverflow) | 1975-04-12 |
| GB1424375A (en) | 1976-02-11 |
| FR2182953B1 (enrdf_load_stackoverflow) | 1976-07-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |