GB1211694A - Derivatives of 7-aminocephalosporanic acid - Google Patents
Derivatives of 7-aminocephalosporanic acidInfo
- Publication number
- GB1211694A GB1211694A GB56301/66A GB5630166A GB1211694A GB 1211694 A GB1211694 A GB 1211694A GB 56301/66 A GB56301/66 A GB 56301/66A GB 5630166 A GB5630166 A GB 5630166A GB 1211694 A GB1211694 A GB 1211694A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- ester
- acyl
- methyl
- cyano
- 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
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title 1
- 150000002148 esters Chemical class 0.000 abstract 6
- 125000002252 acyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 3
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- -1 silyl ester Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 abstract 2
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 abstract 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 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 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 150000003672 ureas Chemical class 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
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- 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
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
Abstract
1,211,694. Cephalosporins. GLAXO LABORATORIES Ltd. 4 Dec., 1967 [15 Dec., 1966], No. 56301/66. Heading C2A. [Also in Division A5] The invention comprises 7 - acylamido - 3 - methyl (or 3-substituted methyl)-ceph-3-em-4- carboxylic acids having an N-linked polyazole ring substituent on the acylamido group at the 7-position and/or on the methyl group at the 3-position, salts and esters thereof; and the corresponding 7-amino compounds. The polyazole ring contains at least three N atoms in the ring. Preferred are the 1-(7<SP>1</SP>-acylamido-4<SP>1</SP>-carboxyceph - 3<SP>1</SP> - em - 3<SP>1</SP> - yl methyl) - 1,2,3- triazoles and -1,2,3-triazolines and particularly triazolines of Formula III wherein R is H or acyl and the groups Y are cyano or methoxycarbonyl groups, e.g. 4,5- dimethoxycarbonyl-1-(4<SP>1</SP>- carboxy - 7<SP>1</SP> - phenylacetamido - ceph - 31 - em - 3<SP>1</SP>- yl methyl)- 1,2,3-thiazole; and salts and esters thereof. The compounds are prepared by reacting a dipolarophile with a cephalosporanic acid, salt or ester, the acid having the Formula II wherein R is H or acyl which may contain an azido group; and X is an acetoxy group, an azido group or H, at least one of R and X providing the compound of Formula II with at least one azido group, to obtain a compound having at least one polyazole ring substituent, whereafter, when R is H, the resulting compound may be acylated. The ester may be a diphenylmethyl, stannyl or silyl ester. The dipolarophiles are substances which react with groups having a dipole and may be classified as (a) acetylenic, i.e. of structure R<SP>1</SP>C#CR<SP>2</SP>, where R<SP>1</SP> and R<SP>2</SP> may be the same or differe group or atom, e.g. H, cyano, ester such methoxycarbonyl or acyl, e.g. benzoyl; (b) ethylenic, i.e. R<SP>5</SP>.R<SP>6</SP>C = CR<SP>7</SP>R<SP>8</SP>, wherein R<SP>5</SP>, R<SP>6</SP>, R<SP>7</SP> and R<SP>8</SP> may be the same or different and may be H, cyano, ester, e.g. methoxy carbonyl, acyl or carboxy; (c) cyano compounds other than those of (a) and (b) particularly cyanogen and alkoxy carbonyl cyanides. The azide and dipolarophile are reacted in an organic solvent at 15 to 150 C. A wide range of specific acyl groups for R of Formulµ II and III is listed. The silyl or stannyl ester group is removed by treatment with a compound containing active hydrogen, e.g. water, acidified or basified water, alcohols, phenols, ureas and amides. Specifications 1,012,943, 1,054,806, 1,082,943 and 1,082,962 are referred to.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB56301/66A GB1211694A (en) | 1966-12-15 | 1966-12-15 | Derivatives of 7-aminocephalosporanic acid |
| DE1695049A DE1695049C3 (en) | 1966-12-15 | 1967-12-12 | Process for the preparation of cephalosporin derivatives |
| CH1748767A CH558810A (en) | 1966-12-15 | 1967-12-13 | PROCESS FOR THE PRODUCTION OF NEW CEPHALOSPORINES AND THEIR ACID DERIVATIVES. |
| FR132294A FR7520M (en) | 1966-12-15 | 1967-12-14 | |
| FR1572190D FR1572190A (en) | 1966-12-15 | 1967-12-14 | |
| SE6717251A SE373142B (en) | 1966-12-15 | 1967-12-15 | |
| NL6717107A NL6717107A (en) | 1966-12-15 | 1967-12-15 | |
| JP42080160A JPS5013275B1 (en) | 1966-12-15 | 1967-12-15 | |
| US00108189A US3821206A (en) | 1966-12-15 | 1971-01-20 | Cephalosporins having a polyazole substituent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB56301/66A GB1211694A (en) | 1966-12-15 | 1966-12-15 | Derivatives of 7-aminocephalosporanic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1211694A true GB1211694A (en) | 1970-11-11 |
Family
ID=10476282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB56301/66A Expired GB1211694A (en) | 1966-12-15 | 1966-12-15 | Derivatives of 7-aminocephalosporanic acid |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5013275B1 (en) |
| CH (1) | CH558810A (en) |
| DE (1) | DE1695049C3 (en) |
| FR (2) | FR7520M (en) |
| GB (1) | GB1211694A (en) |
| NL (1) | NL6717107A (en) |
| SE (1) | SE373142B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001516A1 (en) * | 1977-10-10 | 1979-04-18 | Glaxo Group Limited | Beta-Lactam compounds, processes for their preparation, pharmaceutical compositions containing them and intermediates of use in their preparation |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR860000487B1 (en) * | 1980-09-25 | 1986-04-30 | 도야마 가가꾸 고오교 가부시끼가이샤 | Process for preparing cephalosporins |
| NZ198350A (en) * | 1980-09-25 | 1985-02-28 | Toyama Chemical Co Ltd | Cephalosporins and intermediates;pharmaceutical compositions |
| FR2533216A1 (en) * | 1982-09-22 | 1984-03-23 | Toyama Chemical Co Ltd | New cephalosporins and their salts. |
-
1966
- 1966-12-15 GB GB56301/66A patent/GB1211694A/en not_active Expired
-
1967
- 1967-12-12 DE DE1695049A patent/DE1695049C3/en not_active Expired
- 1967-12-13 CH CH1748767A patent/CH558810A/en not_active IP Right Cessation
- 1967-12-14 FR FR132294A patent/FR7520M/fr not_active Expired
- 1967-12-14 FR FR1572190D patent/FR1572190A/fr not_active Expired
- 1967-12-15 JP JP42080160A patent/JPS5013275B1/ja active Pending
- 1967-12-15 SE SE6717251A patent/SE373142B/xx unknown
- 1967-12-15 NL NL6717107A patent/NL6717107A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001516A1 (en) * | 1977-10-10 | 1979-04-18 | Glaxo Group Limited | Beta-Lactam compounds, processes for their preparation, pharmaceutical compositions containing them and intermediates of use in their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6717107A (en) | 1968-06-17 |
| SE373142B (en) | 1975-01-27 |
| DE1695049C3 (en) | 1980-02-21 |
| DE1695049A1 (en) | 1971-03-18 |
| CH558810A (en) | 1975-02-14 |
| FR1572190A (en) | 1969-06-27 |
| JPS5013275B1 (en) | 1975-05-19 |
| DE1695049B2 (en) | 1979-06-21 |
| FR7520M (en) | 1969-12-15 |
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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 |