PL88748B1 - - Google Patents
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- Publication number
- PL88748B1 PL88748B1 PL1974169070A PL16907074A PL88748B1 PL 88748 B1 PL88748 B1 PL 88748B1 PL 1974169070 A PL1974169070 A PL 1974169070A PL 16907074 A PL16907074 A PL 16907074A PL 88748 B1 PL88748 B1 PL 88748B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- substituted
- wzdr
- thallium
- mercury
- Prior art date
Links
- -1 2-tenyl Chemical group 0.000 claims 17
- 238000000034 method Methods 0.000 claims 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 229910001385 heavy metal Inorganic materials 0.000 claims 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 4
- 229910052753 mercury Inorganic materials 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229910052709 silver Inorganic materials 0.000 claims 4
- 239000004332 silver Substances 0.000 claims 4
- 229910052716 thallium Inorganic materials 0.000 claims 4
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims 4
- 239000011135 tin Substances 0.000 claims 4
- 229910052718 tin Inorganic materials 0.000 claims 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 3
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 229910052802 copper Inorganic materials 0.000 claims 3
- 239000010949 copper Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 229910052793 cadmium Inorganic materials 0.000 claims 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 229910017052 cobalt Inorganic materials 0.000 claims 2
- 239000010941 cobalt Substances 0.000 claims 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 2
- 229910052737 gold Inorganic materials 0.000 claims 2
- 239000010931 gold Substances 0.000 claims 2
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 229910052742 iron Inorganic materials 0.000 claims 2
- 239000011133 lead Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 229910052759 nickel Inorganic materials 0.000 claims 2
- 150000002960 penicillins Chemical class 0.000 claims 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (6)
1. Zastrzezenia patentowe 1. Sposób wytwarzania pochodnych kwasu 7-acy- 50 loaminodezacetoksycefalosporanowego o wzorze 1, w którym R oznacza grupe benzylowa, fenoksy- metylowa, Ill-rzed. butoksylowa, 2-tenylowa, cy- janometylowa, alkilowa o 1—6 atomach wegla, pod¬ stawiona igrupe benzylowa, która w pierscieniu *5 fenylowym moze byc podstawiona grupami hydro¬ ksylowymi, alkoksylowymi, alkilotio i atomami chlorowca, a w grupie metylenowej nizsza grupa alkilowa, grupa aminowa, acyloaminowa, alkoksy- karbonyflowa i grupa o wzorze 3, w którym X 60 oznacza grupe alkilowa o 1—4 atomach wegla, R' oznacza grupe p-nitrofoenzylowa, p-metoksy^ benzylowa, /?,£/?-trójchloroetylowa, dwufenylome- tylowa, 9-fluorenylowa, Ill-rzed. butylowa, try- tylowa, fenacylowa, p-chlorofenacylowa, p-lbromo- w fenacylowa! p-nitrofenacylowa i cyjanometylowa,88748 10 znamienny tym, ze S-tlenki estrów penicyliny o wzorze 2, w którym R i R' maja wyzej podane znaczenie, ogrzewa sie w ciagu 10 minut do 5 go¬ dzin w temperaturze 60—150°C, w obecnosci soli metali ciezkich o wzorze Me (R*—SO$)n przy czym Me oznacza atom miedzi, srebra, zlota, cynku, kad¬ mu, rteci, talu, cyny, olowiu, zelaza, kobaltu lub niklu, zwlaszcza atom miedzi, cyny, srebra, rteci i talu, R" oznacza rodnik alkilowy o 1—4 ato¬ mach wegla ewentualnie podstawiony fluorem lub rodnik fenyIowy lub naftyIowy ewentualnie pod¬ stawiony rodnikami metylowymi lub atomami chlorowca, a n oznacza 1—3 w zaleznosci od war¬ tosciowosci kationu metalu.
2. Sposób wedlug zastrz. 1, znamienny tym, ze reakcje prowadzi sie w temperaturze 80—130°C.
3. Sposób wedlug zastrz. 1, znamienny tym, ze sole metali ciezkich wprowadza sie w ilosci 1—20, zwlaszcza 3—10*/« molowych w przeliczeniu na uzy¬ ty S-tlenek.
4. Sposób wytwarzania pochodnych kwasu 7-acy- loaminodezacetoksycefalosporanowego o wzorze 1, w którym R oznacza podstawiona grupe benzylo¬ wa, która w pierscieniu fenyIowym moze byc pod¬ stawiona grupami hydroksylowymi, alkoksylowy- mi, alkilotio i atomami chlorowca, a w grupie me¬ tylenowej grupa azydowa, a R' oznacza grupe ip-nitrobenzylowa, p-metoksybenzylowa, /?,//,/?-tfój- chloroetylowa, dwufenylometylowa, 9-flucreny- lowa, III-butylewa, trytylowa, fenacylowa, p-chlo- 5 rofenacylowa, p-bromofenacylowa, p-nitrofenacy- lowa i cyjanometylowa, znamienny tym, ze S-tlen¬ ki estrów penicyliny o wzorze 2, w którym R i R' imaja wyzej podane znaczenie, ogrzewa sie w cia¬ gu 10 minut do 5 godzin w temperaturze 60— io i5fr°C, w obecnosci soli metali ciezkich o wzorze Me dzi, srebra, zlota, cynku, kadmu, rteci, talu, cy¬ ny, olowiu, zelaza, kobaltu lub. niklu, zwlaszcza atom miedzi, cyny, srebra, rteci i talu, R" ozna¬ cza rodnik alkilowy o 1—4 atomach wegla ewen¬ tualnie podstawiony fluorem lub rodnik fenylo- wy lub naftylówy ewentualnie podstawiony rodni¬ kami metylowymi lub atomami chlorowca, a n oznacza 1—3 w zaleznosci od wartosciowosci ka¬ tionu metalu.
5. Sposób wedlug zastrz. 2, znamienny tym, ze reakcje prowadzi sie w temperaturze 80—130°C.
6. Sposób wedlug zastrz. 2, znamienny tym, ze sole metali ciezkich wprowadza sie w ilosci 1—20, zwlaszcza 3—10f/» molowych w przeliczeniu na uzyty S-tlenek. 15 20 C00R' WZtfR 1 v-C0-NH- 0 o t r -N C00R' WZCfR 2 -NH-OCH-C00X CH, WZÓR 388748 Oo-^co-^p^^ 0 I 7— ( WZdR 4 C02CH2-^)-N02 o-°-^-c°-n^^CH3_ C02CH2-^M)CH3 WZdR 5 ^CH2-C0-NHT=r NV^CH3 Ol3,, C02-CH2-^_/-0CH3 WZÓR 6 {~^)-0-CH2-C0-NH 0 WZÓR 7 C02-CH2-CN88718 -0-CH-CO-NH |^~NY^CH, C02-CH2-C0-{ "VBr WZÓR 8 -0-CH-CO-NH-| ( 0/-y^CH3 WZdR 9 ^^-CH-CO--NH N ^' ,N3 O CK, C02-CH2-\ ^N02 WZdR 1088748 O t 65 2 J li r^CH, O -H20 COO-CH2-/^h NO. C6H5-0- CH2-C0- NH~! { O M ^J—CH, COO-CKH^^NCL SCHEMAT DN-3, zam. 162.77 Cena 10 zt PL PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732309599 DE2309599A1 (de) | 1973-02-26 | 1973-02-26 | Verfahren zur herstellung von 7-acylamino-desacetoxy-cephalosporansaeurederivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL88748B1 true PL88748B1 (pl) | 1976-09-30 |
Family
ID=5873158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1974169070A PL88748B1 (pl) | 1973-02-26 | 1974-02-25 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3997533A (pl) |
| JP (1) | JPS49117489A (pl) |
| AT (1) | AT330350B (pl) |
| AU (1) | AU476881B2 (pl) |
| BE (1) | BE811521A (pl) |
| CA (1) | CA1032156A (pl) |
| CH (1) | CH591498A5 (pl) |
| DD (1) | DD113549A5 (pl) |
| DE (1) | DE2309599A1 (pl) |
| EG (1) | EG11155A (pl) |
| ES (1) | ES423619A1 (pl) |
| FR (1) | FR2219167B1 (pl) |
| GB (1) | GB1420573A (pl) |
| HU (1) | HU168588B (pl) |
| IL (1) | IL44265A (pl) |
| LU (1) | LU69477A1 (pl) |
| NL (1) | NL7402533A (pl) |
| PL (1) | PL88748B1 (pl) |
| RO (1) | RO63497A (pl) |
| ZA (1) | ZA741210B (pl) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4164586A (en) * | 1974-07-19 | 1979-08-14 | Hoffmann-La Roche Inc. | Therapeutic agent for improving cardiovascular function |
| US4096329A (en) * | 1976-03-05 | 1978-06-20 | E. R. Squibb & Sons, Inc. | 7-Cyanoalkylureido 3 heterocylic thio methyl cephalosporins |
| US4128723A (en) * | 1977-02-02 | 1978-12-05 | E. R. Squibb & Sons, Inc. | Cyanoalkylureido cephalosporins |
| US4096330A (en) * | 1977-04-21 | 1978-06-20 | E. R. Squibb & Sons, Inc. | 7β-[[[(2-Cyanomethyl)amino]-1,2-dioxoethyl]amino]acyl cephalosporins |
| US4518773A (en) * | 1978-04-03 | 1985-05-21 | Bristol-Myers Company | "3-Carbamoyloxy cephalosporins" |
| US4322347A (en) * | 1978-04-03 | 1982-03-30 | Bristol-Myers Company | 2-Carbamoyloxymethyl-penicillin derivatives |
| US4310459A (en) * | 1978-04-03 | 1982-01-12 | Bristol-Myers Company | Process for producing carbamoyl substituted penams and carbamoyl substituted cephams from penicillin sulfoxide esters |
| US4426520A (en) | 1978-04-03 | 1984-01-17 | Bristol-Myers Company | 3-Carbamoyloxy-cepham-4-carboxylic acid derivatives |
| US4168266A (en) * | 1978-05-30 | 1979-09-18 | E. R. Squibb & Sons, Inc. | 6-[[[(2-Cyanomethyl)amino]-1,2-dioxoethyl]-amino]acyl penicillins |
| US4174399A (en) * | 1978-07-10 | 1979-11-13 | Syntex (Usa) Inc. | Treatment of lactic acidosis in ruminants |
| US4374982A (en) * | 1979-11-07 | 1983-02-22 | Bristol-Myers Company | Cepham compounds |
| CN103058932B (zh) * | 2013-02-01 | 2015-10-07 | 京博农化科技股份有限公司 | N-(2-苯并咪唑基)-氨基甲酸甲酯的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH565809A5 (pl) * | 1969-03-11 | 1975-08-29 | Glaxo Lab Ltd | |
| US3853861A (en) * | 1969-03-18 | 1974-12-10 | Lilly Co Eli | Cephalexin intermediate |
| GB1312233A (en) * | 1969-12-05 | 1973-04-04 | Glaxo Lab Ltd | Cephalosporin compounds |
| YU35448B (en) * | 1970-02-18 | 1981-02-28 | Koninkl Gist Spiritus | Process for obtaining 7-substituted amino-deacetoxy cephalosporanic acids |
| US3799924A (en) * | 1970-12-18 | 1974-03-26 | Lilly Co Eli | Ester cleavage process |
| DE2064107A1 (de) * | 1970-12-28 | 1972-07-06 | Farbwerke Hoechst AG vormals Meister Lucius & Brüning, 6000 Frankfurt | Verfahren zur Herstellung von Cephem-4-carbonsäureestern |
| GB1431174A (en) * | 1972-06-30 | 1976-04-07 | Clin Midy | Process for the conversion of a penicillin s-oxide into a corresponding desacetoxycephalosporin |
-
1973
- 1973-02-26 DE DE19732309599 patent/DE2309599A1/de active Pending
-
1974
- 1974-02-14 US US05/442,810 patent/US3997533A/en not_active Expired - Lifetime
- 1974-02-19 CA CA192,962A patent/CA1032156A/en not_active Expired
- 1974-02-19 RO RO7400077746A patent/RO63497A/ro unknown
- 1974-02-20 DD DD176699A patent/DD113549A5/xx unknown
- 1974-02-22 CH CH255274A patent/CH591498A5/xx not_active IP Right Cessation
- 1974-02-22 JP JP49020658A patent/JPS49117489A/ja active Pending
- 1974-02-22 AU AU65909/74A patent/AU476881B2/en not_active Expired
- 1974-02-22 IL IL44265A patent/IL44265A/en unknown
- 1974-02-22 LU LU69477A patent/LU69477A1/xx unknown
- 1974-02-23 EG EG51/74A patent/EG11155A/xx active
- 1974-02-25 ZA ZA00741210A patent/ZA741210B/xx unknown
- 1974-02-25 BE BE141341A patent/BE811521A/xx unknown
- 1974-02-25 ES ES423619A patent/ES423619A1/es not_active Expired
- 1974-02-25 NL NL7402533A patent/NL7402533A/xx unknown
- 1974-02-25 PL PL1974169070A patent/PL88748B1/pl unknown
- 1974-02-25 GB GB842174A patent/GB1420573A/en not_active Expired
- 1974-02-26 HU HUBA3036A patent/HU168588B/hu unknown
- 1974-02-26 AT AT155474A patent/AT330350B/de not_active IP Right Cessation
- 1974-02-26 FR FR7406499A patent/FR2219167B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL44265A0 (en) | 1974-05-16 |
| USB442810I5 (pl) | 1976-02-24 |
| NL7402533A (pl) | 1974-08-28 |
| ZA741210B (en) | 1975-01-29 |
| DD113549A5 (pl) | 1975-06-12 |
| ES423619A1 (es) | 1976-05-01 |
| FR2219167B1 (pl) | 1977-09-23 |
| AU6590974A (en) | 1975-08-28 |
| GB1420573A (en) | 1976-01-07 |
| HU168588B (pl) | 1976-06-28 |
| EG11155A (en) | 1977-05-31 |
| RO63497A (fr) | 1978-10-15 |
| US3997533A (en) | 1976-12-14 |
| DE2309599A1 (de) | 1974-09-05 |
| CH591498A5 (pl) | 1977-09-30 |
| BE811521A (fr) | 1974-08-26 |
| AT330350B (de) | 1976-06-25 |
| AU476881B2 (en) | 1976-10-07 |
| CA1032156A (en) | 1978-05-30 |
| FR2219167A1 (pl) | 1974-09-20 |
| ATA155474A (de) | 1975-09-15 |
| JPS49117489A (pl) | 1974-11-09 |
| IL44265A (en) | 1976-10-31 |
| LU69477A1 (pl) | 1974-09-25 |
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