ES339028A1 - Improvements in or relating to cephalosporins - Google Patents
Improvements in or relating to cephalosporinsInfo
- Publication number
- ES339028A1 ES339028A1 ES339028A ES339028A ES339028A1 ES 339028 A1 ES339028 A1 ES 339028A1 ES 339028 A ES339028 A ES 339028A ES 339028 A ES339028 A ES 339028A ES 339028 A1 ES339028 A1 ES 339028A1
- Authority
- ES
- Spain
- Prior art keywords
- salt
- acid
- acid addition
- addition salt
- pyridinium
- 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
- 229930186147 Cephalosporin Natural products 0.000 title 1
- 229940124587 cephalosporin Drugs 0.000 title 1
- 150000001780 cephalosporins Chemical class 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 abstract 4
- 239000008346 aqueous phase Substances 0.000 abstract 3
- 239000012535 impurity Substances 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical class C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 1
- 230000002745 absorbent Effects 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229960003237 betaine Drugs 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 abstract 1
- 229960003866 cefaloridine Drugs 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- -1 iodide ions Chemical class 0.000 abstract 1
- 239000012452 mother liquor Substances 0.000 abstract 1
- 239000012429 reaction media Substances 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
- C07D501/38—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
- C07D501/46—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 with the 7-amino radical acylated by carboxylic acids containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
An N - (7 - acylamido - ceph - 3 - em - 3 - ylmethyl) - pyridinium - 4 - carboxylate is produced by (A) reacting a 7-acylamidocephalosporanic acid or a salt thereof with pyridine or a substituted pyridine in solution in a reaction medium in the presence of at least an equivalent equimolar proportion, calculated on the 7-acylamido cephalosporanic acid, of thiocyanate or iodide ions and recovering the resultant N-(7- acylamidoceph - 3 - em - 3 - yl - methyl)- pyridinium-4-carboxylate as its crude hydrothiocyanate or hydroidide acid addition salt (B) converting the crude hydrothiocyanate or hydroiodide acid addition salt from (A) to the betaine form by reacting said salt with a base, the betaine being recovered in an aqueous phase (C) if desired, passing the aqueous phase from (B) through one or more ion-exchangers and, if desired, decolouring absorbent, to remove further impurities, e.g. acidic and basic impurities as well as colourants (D) reacting the aqueous phase from (B) or (C) with an acid to form an insoluble acid addition salt (E) separating the acid addition salt from (D) from the mother liquor and converting the salt to the betaine form by reaction with a base. The examples relate to the preparation of N-(7-21- thienylacetamidoceph - 3 - em - 3 - ylmethyl)- pyridinium - 4 - carboxylate - (cephaloridine). The pyridine may be substituted by one or more alkyl, carboxy or carbamoyl groups. Specifications 912,541, 966,221, 1,028,563, 1,101,561, 1,101,562 and 1,132,621 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1571966A GB1171603A (en) | 1966-04-07 | 1966-04-07 | Improvements in or relating to cephalosporins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES339028A1 true ES339028A1 (en) | 1968-07-01 |
Family
ID=10064258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES339028A Expired ES339028A1 (en) | 1966-04-07 | 1967-04-07 | Improvements in or relating to cephalosporins |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT287189B (en) |
| BE (1) | BE696775A (en) |
| CH (1) | CH504472A (en) |
| DE (1) | DE1695015C3 (en) |
| DK (1) | DK136609C (en) |
| ES (1) | ES339028A1 (en) |
| GB (1) | GB1171603A (en) |
| GR (1) | GR35150B (en) |
| NL (1) | NL6704945A (en) |
| SE (1) | SE370080B (en) |
-
1966
- 1966-04-07 GB GB1571966A patent/GB1171603A/en not_active Expired
-
1967
- 1967-04-04 GR GR670135150A patent/GR35150B/en unknown
- 1967-04-07 ES ES339028A patent/ES339028A1/en not_active Expired
- 1967-04-07 BE BE696775D patent/BE696775A/xx not_active IP Right Cessation
- 1967-04-07 CH CH494767A patent/CH504472A/en not_active IP Right Cessation
- 1967-04-07 AT AT333467A patent/AT287189B/en active
- 1967-04-07 SE SE489467A patent/SE370080B/xx unknown
- 1967-04-07 DE DE1967G0049776 patent/DE1695015C3/en not_active Expired
- 1967-04-07 DK DK195867A patent/DK136609C/en not_active IP Right Cessation
- 1967-04-07 NL NL6704945A patent/NL6704945A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6704945A (en) | 1967-10-09 |
| DE1695015C3 (en) | 1978-05-03 |
| AT287189B (en) | 1971-01-11 |
| SE370080B (en) | 1974-09-30 |
| BE696775A (en) | 1967-10-09 |
| DE1695015B2 (en) | 1977-09-22 |
| DK136609C (en) | 1978-04-10 |
| DE1695015A1 (en) | 1972-03-09 |
| CH504472A (en) | 1971-03-15 |
| DK136609B (en) | 1977-10-31 |
| GR35150B (en) | 1968-08-21 |
| GB1171603A (en) | 1969-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD2A | Announcement of lapse in spain |
Effective date: 20170626 |