CH583242A5 - Verfahren zur Herstellung von Verbindungen der Cephalosporinreihe - Google Patents
Verfahren zur Herstellung von Verbindungen der CephalosporinreiheInfo
- Publication number
- CH583242A5 CH583242A5 CH1186275A CH1186275A CH583242A5 CH 583242 A5 CH583242 A5 CH 583242A5 CH 1186275 A CH1186275 A CH 1186275A CH 1186275 A CH1186275 A CH 1186275A CH 583242 A5 CH583242 A5 CH 583242A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- carboxylate
- ceph
- ylmethyl
- sulfo
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 29
- 229930186147 Cephalosporin Natural products 0.000 title claims description 12
- 229940124587 cephalosporin Drugs 0.000 title claims description 12
- 150000001780 cephalosporins Chemical class 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 6
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 16
- -1 α-sulfopropionamido Chemical group 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 230000001419 dependent effect Effects 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 238000002329 infrared spectrum Methods 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000005481 NMR spectroscopy Methods 0.000 claims description 4
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 4
- 241000191967 Staphylococcus aureus Species 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003952 β-lactams Chemical class 0.000 claims description 4
- 229920001429 chelating resin Polymers 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- FVFVBVBWERFYML-UHFFFAOYSA-N 2-chloro-2-oxo-1-thiophen-3-ylethanesulfonic acid Chemical compound OS(=O)(=O)C(C(Cl)=O)C=1C=CSC=1 FVFVBVBWERFYML-UHFFFAOYSA-N 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 claims description 2
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 claims description 2
- 229940056360 penicillin g Drugs 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical group S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 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 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PIMQVFSTMNWDMJ-UHFFFAOYSA-N 2-chloro-2-oxo-1-phenylethanesulfonic acid Chemical compound OS(=O)(=O)C(C(Cl)=O)C1=CC=CC=C1 PIMQVFSTMNWDMJ-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/23—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings other than six-membered aromatic rings
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5346671A JPS5324439B1 (no) | 1971-07-17 | 1971-07-17 | |
| JP8413071A JPS5442998B2 (no) | 1971-10-22 | 1971-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH583242A5 true CH583242A5 (de) | 1976-12-31 |
Family
ID=26394179
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1186275A CH583242A5 (de) | 1971-07-17 | 1972-07-14 | Verfahren zur Herstellung von Verbindungen der Cephalosporinreihe |
| CH1062372A CH586228A5 (no) | 1971-07-17 | 1972-07-14 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1062372A CH586228A5 (no) | 1971-07-17 | 1972-07-14 |
Country Status (16)
| Country | Link |
|---|---|
| AT (2) | AT318143B (no) |
| AU (1) | AU464451B2 (no) |
| BE (1) | BE786271A (no) |
| CA (1) | CA1005813A (no) |
| CH (2) | CH583242A5 (no) |
| DE (1) | DE2234280C3 (no) |
| DK (1) | DK147339C (no) |
| ES (1) | ES404745A1 (no) |
| FR (1) | FR2146313B1 (no) |
| GB (1) | GB1387656A (no) |
| HK (1) | HK27278A (no) |
| HU (1) | HU166318B (no) |
| MY (1) | MY7800302A (no) |
| NL (1) | NL165749C (no) |
| NO (1) | NO142914C (no) |
| SE (1) | SE405478B (no) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3962232A (en) * | 1973-11-05 | 1976-06-08 | Eli Lilly And Company | 7-methoxycephalosporins |
| DE2407715C2 (de) * | 1974-02-18 | 1982-12-02 | Bayer Ag, 5090 Leverkusen | Cephalosporine, Verfahren zu ihrer Herstellung sowie Arzneimittel |
| JPS5285143A (en) * | 1976-01-05 | 1977-07-15 | Takeda Chem Ind Ltd | Antimicrobial agents and method of preparing same |
| US4063019A (en) | 1976-03-30 | 1977-12-13 | E. R. Squibb & Sons, Inc. | [[[(2,4-Dioxo-1-imidazolidinyl)amino]carbonyl]amino]-acetylcephalosporin derivatives |
| PH16771A (en) * | 1978-04-19 | 1984-02-22 | Ciba Geigy Ag | Synergistic mixtures of cepsulodin sodium and an aminoglycoside |
| US4396619A (en) * | 1981-09-08 | 1983-08-02 | Eli Lilly And Company | Cephalosporin betaines |
| US4396620A (en) * | 1981-09-08 | 1983-08-02 | Eli Lilly And Company | Cephalosporin quinolinium betaines |
| RU2482312C2 (ru) * | 2011-07-04 | 2013-05-20 | В & C Boрлд Ко.Лтд | Воздушно-реактивный бесклапанный пульсирующий двигатель |
-
0
- BE BE786271D patent/BE786271A/xx not_active IP Right Cessation
-
1972
- 1972-07-11 ES ES404745A patent/ES404745A1/es not_active Expired
- 1972-07-12 SE SE7209172A patent/SE405478B/xx unknown
- 1972-07-12 DE DE2234280A patent/DE2234280C3/de not_active Expired
- 1972-07-13 NO NO2518/72A patent/NO142914C/no unknown
- 1972-07-13 AU AU44531/72A patent/AU464451B2/en not_active Expired
- 1972-07-14 CA CA147,161A patent/CA1005813A/en not_active Expired
- 1972-07-14 NL NL7209811.A patent/NL165749C/xx not_active IP Right Cessation
- 1972-07-14 CH CH1186275A patent/CH583242A5/de not_active IP Right Cessation
- 1972-07-14 AT AT607072A patent/AT318143B/de not_active IP Right Cessation
- 1972-07-14 CH CH1062372A patent/CH586228A5/xx not_active IP Right Cessation
- 1972-07-14 AT AT855973A patent/AT320154B/de not_active IP Right Cessation
- 1972-07-14 DK DK354372A patent/DK147339C/da not_active IP Right Cessation
- 1972-07-17 HU HUTA1194A patent/HU166318B/hu unknown
- 1972-07-17 GB GB3339572A patent/GB1387656A/en not_active Expired
- 1972-07-17 FR FR7225732A patent/FR2146313B1/fr not_active Expired
-
1978
- 1978-06-01 HK HK272/78A patent/HK27278A/xx unknown
- 1978-12-30 MY MY302/78A patent/MY7800302A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK27278A (en) | 1978-06-09 |
| NL165749B (nl) | 1980-12-15 |
| CA1005813A (en) | 1977-02-22 |
| NL165749C (nl) | 1981-05-15 |
| HU166318B (no) | 1975-02-28 |
| ES404745A1 (es) | 1975-11-01 |
| DK147339B (da) | 1984-06-25 |
| AT318143B (de) | 1974-09-25 |
| FR2146313A1 (no) | 1973-03-02 |
| SE405478B (sv) | 1978-12-11 |
| FR2146313B1 (no) | 1975-03-14 |
| NL7209811A (no) | 1973-01-19 |
| NO142914C (no) | 1980-11-12 |
| MY7800302A (en) | 1978-12-31 |
| DE2234280C3 (de) | 1979-11-29 |
| GB1387656A (en) | 1975-03-19 |
| BE786271A (fr) | 1973-01-15 |
| CH586228A5 (no) | 1977-03-31 |
| AT320154B (de) | 1975-01-27 |
| AU4453172A (en) | 1974-01-17 |
| NO142914B (no) | 1980-08-04 |
| DE2234280A1 (de) | 1973-02-08 |
| AU464451B2 (en) | 1975-08-28 |
| DE2234280B2 (de) | 1979-03-29 |
| SE7209172L (no) | 1973-01-18 |
| DK147339C (da) | 1985-01-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |