PL89385B1 - - Google Patents
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- Publication number
- PL89385B1 PL89385B1 PL1973164647A PL16464773A PL89385B1 PL 89385 B1 PL89385 B1 PL 89385B1 PL 1973164647 A PL1973164647 A PL 1973164647A PL 16464773 A PL16464773 A PL 16464773A PL 89385 B1 PL89385 B1 PL 89385B1
- Authority
- PL
- Poland
- Prior art keywords
- tetrazole
- preparation
- methyl
- substituted
- esters
- Prior art date
Links
- -1 alkoxycarbonyl cyanide Chemical compound 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 229930186147 Cephalosporin Natural products 0.000 claims description 4
- 229940124587 cephalosporin Drugs 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 235000019439 ethyl acetate Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229930182555 Penicillin Natural products 0.000 claims 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical group 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 1
- 125000001271 cephalosporin group Chemical group 0.000 claims 1
- 229940049954 penicillin Drugs 0.000 claims 1
- 150000002960 penicillins Chemical class 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 description 9
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 6
- JUNAPQMUUHSYOV-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)acetic acid Chemical class OC(=O)CC=1N=NNN=1 JUNAPQMUUHSYOV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 3
- GRWAIJBHBCCLGS-UHFFFAOYSA-N 2-(tetrazol-1-yl)acetic acid Chemical class OC(=O)CN1C=NN=N1 GRWAIJBHBCCLGS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- SFFUEHODRAXXIA-UHFFFAOYSA-N 2,2,2-trifluoroacetonitrile Chemical compound FC(F)(F)C#N SFFUEHODRAXXIA-UHFFFAOYSA-N 0.000 description 1
- ZYHXBGMQUWRUBE-UHFFFAOYSA-N 2-(tetrazol-2-yl)acetic acid Chemical class OC(=O)CN1N=CN=N1 ZYHXBGMQUWRUBE-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- MSMGXWFHBSCQFB-UHFFFAOYSA-N ethyl cyanoformate Chemical compound CCOC(=O)C#N MSMGXWFHBSCQFB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- RXYCUKSOYJWGPE-UHFFFAOYSA-N methyl 2-azidoacetate Chemical compound COC(=O)CN=[N+]=[N-] RXYCUKSOYJWGPE-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania kwasów i estrów lH-tetrazolo-1-octowych o wzo¬ rze ogólnym 1.Zwiazki wytwarzane sposobem wedlug wynalazku maja róznorodne zastosowania, sposród których naj¬ bardziej interesujace polega na uzyciu ich jako produktów posrednich przy wytwarzaniu kwasu 1-tetrazolooctowego, który jest uzywany do otrzy¬ mywania pewnych antybiotyków z grupy cefalo- sporyn.W artykule C. R. Jacobsona i in. „Studies in Tetrazole Chemistry", IV, Tetrazole Chemistry, IV, „Tetrazoleacetric Acide and Esters" Journal of Organie Chemistry, tom 21 (1956) str. 311—315 opisano sposób wytwarzania kwasów i estrów -podstawionych — tetrazolooctowych przez meta¬ lizacje 1-podstawionych tetrazoli zawierajacych atom wodoru przy atomie wegla a podstawnika w pozycji 5 pierscienia tetrazolowego za pomoca fenylosodu. Na drodze nasycania dwutlenkiem we¬ gla i hydrolizy 1-podstawionych 5-a-metalotetrazoli otrzymuje sie odpowiednie pochodne kwasów tetra¬ zolooctowych.W artykule F. G. Fallona i in. „Syntesis of 1-sub- stituted Tetrazoles" Journal of Organie Chemistry, tom 22 (1957) str. 933—936 opisano sposób wytwa¬ rzania siedmiu 1-alkilotetrazoli przez reakcje izo- cyjanków alkilowych z kwasem azotowodorowym prowadzona w benzenie.W artykule W. R. Carpentera „The Formartaon 13 of Tetrazoles by the Condensation of Organie Azi- des with Nitriles" Journal of Organie Chemistry, tom 27, str. :208i5—2087 (1962) opisano sposób wy-i twarzania róznych 1,5-dwupodstawionych tetrazoli na drodze kondensacji cieplnej azydków alkilowych lub arylowych z elektroujemnymi nitrylami chlo- rowcoalkilowymi, takimi jak trójfluorometylonitryl, nadfluoropropylonitryl, przy czym zaden z nich nie doprowadzal do wytwarzania estru lub kwasu te- trazolooctowego.W Angen. Chem. Internat. Edit. tom 2 (1969) nr 10, str. 10 sugerowano, ze tylko ubogie w elektro¬ ny potrójne wiazanie C=N cyjanomrówczanu etylu lub cyjanków nadfluoroalkilowych jest zdolne do addycji azydków organicznych i utworzenia 5-trój- fluorometylo-1-alkilo-lH-tetrazoli, lecz nie okreslo¬ no warunków reakcji.W opisie patentowym St. Zjedn. Ameryki nr 3 073 731 opisano sposób wytwarzania interslia 1- i 2-tetrazolooctanów etylu z tetrazolu i bromo- octanu etylu. Produkt ten jest uzywany jako pla¬ styfikator.W The Canadian Journal of Chemistry, tom 47 (1969), str. 813—819 R. Raap i in. opisali synteze ¦kilkunastu 1-, 2- i 5-tetrazolooctanów na drodze alkilowania soli trójetyloamoniowych tetrazoli za pomoca bromooctanu etylu lub chorooctanu metylu.Opisano równiez sposób hydrolizowania tych estrów do kwasów i podano bibliografie dotyczaca tego zagadnienia. Tamze podano sposób wytwarzania 89 385$9-385 3 4 -trójfluorometylo-l-tetrazolilooctanu metylu z trój- fluoroacetonitrylu i azydooctanu metylu w poda¬ nych przez Carpentera warunkach [W. R. Carpen- ter, J. Org. Chem., 27, 2085 (1962)].W opisie patentowym St. Zjedn. Ameryki nr 3 468 874 podano sposób wytwarzania tetaizoliloocta- nów przez poddanie reakcji izocyjanooctanu III-n.- -butylu z kwasem azotowodorowym lub przez dzia¬ lanie bromoctanem etylu na mieszanine tetrazolu i trójetyioamlny w acetonie. PL
Claims (1)
1. Zastrzezeniami objete sa pewne penicyliny i cyfalosporyny podstawione w pozycji 6 penicyliny lub w pozycji 7 cefalospo- ryny grupa tetrazoloacetamidowa. W holenderskiej publikacji patentowej nr 67/17107 ujawniono sposób wytwarzania 3-podstawionych te- trazolo-metylocefolosporyn na drodze reakcji estru kwasu 3-azydo-metylocefalosporyny z pewnymi grupami dwupolarnofilnymi, np. cyjankiem alkoksy- karbonylowym. Jednakze istnieje potrzeba opracowania dogod¬ nego sposobu wytwarzania kwasów i estrów 1-te- trazolooctowych, które posiadaja szerokie zastoso¬ wanie. Niektóre z tych zastosowan wymieniono. Za¬ den ze znanych sposobów inie jest dostatecznie pro¬ sty i wygodny do stosowania. PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28062572A | 1972-08-14 | 1972-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL89385B1 true PL89385B1 (pl) | 1976-11-30 |
Family
ID=23073908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973164647A PL89385B1 (pl) | 1972-08-14 | 1973-08-13 |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5821628B2 (pl) |
| KR (1) | KR780000071B1 (pl) |
| AR (1) | AR195626A1 (pl) |
| AT (1) | AT329555B (pl) |
| AU (1) | AU476519B2 (pl) |
| BE (1) | BE803520A (pl) |
| BG (1) | BG21220A3 (pl) |
| CA (1) | CA998397A (pl) |
| CH (1) | CH588475A5 (pl) |
| CS (1) | CS179425B2 (pl) |
| DD (1) | DD110272A5 (pl) |
| DE (1) | DE2340409A1 (pl) |
| ES (1) | ES417837A1 (pl) |
| FR (1) | FR2196336B1 (pl) |
| GB (1) | GB1435809A (pl) |
| HU (1) | HU166844B (pl) |
| IE (1) | IE37949B1 (pl) |
| IL (1) | IL42843A (pl) |
| NL (1) | NL179380C (pl) |
| PH (1) | PH10552A (pl) |
| PL (1) | PL89385B1 (pl) |
| RO (1) | RO73460A (pl) |
| SE (1) | SE402913B (pl) |
| SU (1) | SU576935A3 (pl) |
| YU (1) | YU36513B (pl) |
| ZA (1) | ZA735075B (pl) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2854015B2 (de) * | 1978-12-14 | 1980-10-09 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von !H-TetrazoI-1-essigsauren und bestimmter Ester derselben |
| KR101350123B1 (ko) | 2009-03-11 | 2014-01-09 | 닛뽕소다 가부시키가이샤 | 1-알킬-5-벤조일-1ｈ-테트라졸 유도체의 제조 방법 |
| CN114085193A (zh) * | 2021-11-20 | 2022-02-25 | 九江中星医药化工有限公司 | 一种水相法制备1h-四氮唑乙酸及其衍生物的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD70880A (pl) * |
-
1973
- 1973-07-25 IE IE1268/73A patent/IE37949B1/xx unknown
- 1973-07-25 ZA ZA00735075A patent/ZA735075B/xx unknown
- 1973-07-26 AU AU58575/73A patent/AU476519B2/en not_active Expired
- 1973-07-27 IL IL42843A patent/IL42843A/en unknown
- 1973-08-02 CA CA177,995A patent/CA998397A/en not_active Expired
- 1973-08-03 PH PH14880A patent/PH10552A/en unknown
- 1973-08-07 YU YU02148/73A patent/YU36513B/xx unknown
- 1973-08-09 DE DE19732340409 patent/DE2340409A1/de active Granted
- 1973-08-10 BE BE1005292A patent/BE803520A/xx unknown
- 1973-08-10 AT AT703773A patent/AT329555B/de not_active IP Right Cessation
- 1973-08-10 HU HUEI490A patent/HU166844B/hu unknown
- 1973-08-13 ES ES417837A patent/ES417837A1/es not_active Expired
- 1973-08-13 GB GB3813273A patent/GB1435809A/en not_active Expired
- 1973-08-13 KR KR7301319A patent/KR780000071B1/ko not_active Expired
- 1973-08-13 SE SE7311051A patent/SE402913B/xx unknown
- 1973-08-13 SU SU7301955734A patent/SU576935A3/ru active
- 1973-08-13 PL PL1973164647A patent/PL89385B1/pl unknown
- 1973-08-14 CS CS7300005736A patent/CS179425B2/cs unknown
- 1973-08-14 CH CH1171373A patent/CH588475A5/xx not_active IP Right Cessation
- 1973-08-14 NL NLAANVRAGE7311222,A patent/NL179380C/xx not_active IP Right Cessation
- 1973-08-14 AR AR249586A patent/AR195626A1/es active
- 1973-08-14 JP JP48091225A patent/JPS5821628B2/ja not_active Expired
- 1973-08-14 BG BG024317A patent/BG21220A3/xx unknown
- 1973-08-14 RO RO7375793A patent/RO73460A/ro unknown
- 1973-08-14 FR FR7329649A patent/FR2196336B1/fr not_active Expired
- 1973-08-14 DD DD172890A patent/DD110272A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4975580A (pl) | 1974-07-20 |
| YU214873A (en) | 1982-02-25 |
| NL7311222A (pl) | 1974-02-18 |
| RO73460A (ro) | 1982-09-09 |
| AR195626A1 (es) | 1973-10-23 |
| CA998397A (en) | 1976-10-12 |
| NL179380B (nl) | 1986-04-01 |
| YU36513B (en) | 1984-02-29 |
| GB1435809A (en) | 1976-05-19 |
| DE2340409A1 (de) | 1974-02-28 |
| FR2196336A1 (pl) | 1974-03-15 |
| DE2340409C2 (pl) | 1988-03-17 |
| SE402913B (sv) | 1978-07-24 |
| CS179425B2 (en) | 1977-10-31 |
| KR780000071B1 (en) | 1978-03-30 |
| SU576935A3 (ru) | 1977-10-15 |
| BG21220A3 (bg) | 1976-03-20 |
| PH10552A (en) | 1977-06-08 |
| ZA735075B (en) | 1975-03-26 |
| JPS5821628B2 (ja) | 1983-05-02 |
| CH588475A5 (pl) | 1977-06-15 |
| AU5857573A (en) | 1975-01-30 |
| NL179380C (nl) | 1986-09-01 |
| IL42843A (en) | 1976-12-31 |
| AU476519B2 (en) | 1976-09-23 |
| ATA703773A (de) | 1975-08-15 |
| FR2196336B1 (pl) | 1977-02-25 |
| ES417837A1 (es) | 1976-02-16 |
| DD110272A5 (pl) | 1974-12-12 |
| AT329555B (de) | 1976-05-25 |
| IE37949B1 (en) | 1977-11-23 |
| IE37949L (en) | 1974-02-14 |
| BE803520A (fr) | 1974-02-11 |
| IL42843A0 (en) | 1976-01-30 |
| HU166844B (pl) | 1975-06-28 |
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