GB1358217A - Process for preparing 7-aminocephalosporanic acid - Google Patents
Process for preparing 7-aminocephalosporanic acidInfo
- Publication number
- GB1358217A GB1358217A GB4017272A GB4017272A GB1358217A GB 1358217 A GB1358217 A GB 1358217A GB 4017272 A GB4017272 A GB 4017272A GB 4017272 A GB4017272 A GB 4017272A GB 1358217 A GB1358217 A GB 1358217A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacting
- formula
- aminocephalosporanic acid
- inert solvent
- imino
- 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 compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 cephalosporin compound Chemical class 0.000 abstract 9
- 229930186147 Cephalosporin Natural products 0.000 abstract 4
- 229940124587 cephalosporin Drugs 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000012442 inert solvent Substances 0.000 abstract 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 abstract 2
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002091 cationic group Chemical group 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- GZGJIACHBCQSPC-UHFFFAOYSA-N methyl 3-chloropropanoate Chemical compound COC(=O)CCCl GZGJIACHBCQSPC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 abstract 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 abstract 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 abstract 1
- 150000003334 secondary amides Chemical class 0.000 abstract 1
- 150000003511 tertiary amides 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
- C07D501/14—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
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00177869A US3813389A (en) | 1971-09-03 | 1971-09-03 | Process for 7-aminocephalosporanic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1358217A true GB1358217A (en) | 1974-07-03 |
Family
ID=22650263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4017272A Expired GB1358217A (en) | 1971-09-03 | 1972-08-30 | Process for preparing 7-aminocephalosporanic acid |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US3813389A (enExample) |
| JP (1) | JPS558988B2 (enExample) |
| AR (1) | AR208492A1 (enExample) |
| AT (1) | AT314734B (enExample) |
| AU (1) | AU463141B2 (enExample) |
| BE (1) | BE788142A (enExample) |
| BG (1) | BG22836A3 (enExample) |
| CA (1) | CA969178A (enExample) |
| CH (1) | CH558382A (enExample) |
| CS (1) | CS184315B2 (enExample) |
| DD (1) | DD101164A5 (enExample) |
| DE (1) | DE2242299A1 (enExample) |
| DK (1) | DK140942B (enExample) |
| ES (1) | ES406344A1 (enExample) |
| FR (1) | FR2150936B1 (enExample) |
| GB (1) | GB1358217A (enExample) |
| HU (1) | HU166209B (enExample) |
| IE (1) | IE36956B1 (enExample) |
| IL (1) | IL40135A (enExample) |
| NL (1) | NL7211900A (enExample) |
| PH (1) | PH9581A (enExample) |
| PL (1) | PL87749B1 (enExample) |
| RO (1) | RO59967A (enExample) |
| SE (1) | SE392724B (enExample) |
| SU (1) | SU587865A3 (enExample) |
| ZA (1) | ZA725647B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1395184A (en) * | 1972-03-09 | 1975-05-21 | Alfa Farmaceutici Spa | Cephalosporin derivatives |
| GR70261B (enExample) * | 1977-12-12 | 1982-09-02 | Takeda Chemical Industries Ltd | |
| US6518420B2 (en) * | 1997-06-04 | 2003-02-11 | Biochemie Gesellschaft M.B.H. | Precipitation process of 7-aminocephalosporanic acid (7-ACA) |
-
0
- BE BE788142D patent/BE788142A/xx unknown
-
1971
- 1971-09-03 US US00177869A patent/US3813389A/en not_active Expired - Lifetime
-
1972
- 1972-08-15 IL IL40135A patent/IL40135A/xx unknown
- 1972-08-16 ZA ZA725647A patent/ZA725647B/xx unknown
- 1972-08-17 AU AU45709/72A patent/AU463141B2/en not_active Expired
- 1972-08-23 CA CA150,030A patent/CA969178A/en not_active Expired
- 1972-08-25 PH PH13835*UA patent/PH9581A/en unknown
- 1972-08-28 CS CS7200005917A patent/CS184315B2/cs unknown
- 1972-08-28 DE DE2242299A patent/DE2242299A1/de not_active Ceased
- 1972-08-29 FR FR7230641A patent/FR2150936B1/fr not_active Expired
- 1972-08-29 BG BG021280A patent/BG22836A3/xx unknown
- 1972-08-30 GB GB4017272A patent/GB1358217A/en not_active Expired
- 1972-08-30 CH CH1279072A patent/CH558382A/fr not_active IP Right Cessation
- 1972-08-31 AR AR243852A patent/AR208492A1/es active
- 1972-08-31 NL NL7211900A patent/NL7211900A/xx not_active Application Discontinuation
- 1972-09-01 PL PL1972157545A patent/PL87749B1/pl unknown
- 1972-09-01 DK DK433772AA patent/DK140942B/da unknown
- 1972-09-01 SU SU721826870A patent/SU587865A3/ru active
- 1972-09-01 RO RO72106A patent/RO59967A/ro unknown
- 1972-09-01 IE IE1187/72A patent/IE36956B1/xx unknown
- 1972-09-01 SE SE7211345A patent/SE392724B/xx unknown
- 1972-09-01 DD DD165401A patent/DD101164A5/xx unknown
- 1972-09-01 AT AT752872A patent/AT314734B/de not_active IP Right Cessation
- 1972-09-02 JP JP8830072A patent/JPS558988B2/ja not_active Expired
- 1972-09-02 HU HUEI430A patent/HU166209B/hu unknown
- 1972-09-02 ES ES406344A patent/ES406344A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH558382A (fr) | 1975-01-31 |
| AU463141B2 (en) | 1975-07-17 |
| AU4570972A (en) | 1974-02-21 |
| IE36956L (en) | 1973-03-03 |
| SU587865A3 (ru) | 1978-01-05 |
| AR208492A1 (es) | 1977-02-15 |
| PL87749B1 (enExample) | 1976-07-31 |
| JPS558988B2 (enExample) | 1980-03-07 |
| DE2242299A1 (de) | 1973-03-08 |
| DK140942B (da) | 1979-12-10 |
| DD101164A5 (enExample) | 1973-10-20 |
| RO59967A (enExample) | 1976-06-15 |
| HU166209B (enExample) | 1975-02-28 |
| IL40135A (en) | 1975-03-13 |
| CA969178A (en) | 1975-06-10 |
| JPS4834896A (enExample) | 1973-05-22 |
| NL7211900A (enExample) | 1973-03-06 |
| FR2150936A1 (enExample) | 1973-04-13 |
| CS184315B2 (en) | 1978-08-31 |
| ES406344A1 (es) | 1975-09-16 |
| FR2150936B1 (enExample) | 1975-10-17 |
| PH9581A (en) | 1976-01-19 |
| ZA725647B (en) | 1974-03-27 |
| IE36956B1 (en) | 1977-03-30 |
| BE788142A (fr) | 1973-02-28 |
| BG22836A3 (bg) | 1977-04-20 |
| SE392724B (sv) | 1977-04-18 |
| AT314734B (de) | 1974-04-25 |
| IL40135A0 (en) | 1972-10-29 |
| DK140942C (enExample) | 1980-05-19 |
| US3813389A (en) | 1974-05-28 |
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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 |