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)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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 (en, 2012) | 1976-11-30 |
Family
ID=23073908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973164647A PL89385B1 (en, 2012) | 1972-08-14 | 1973-08-13 |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5821628B2 (en, 2012) |
| KR (1) | KR780000071B1 (en, 2012) |
| AR (1) | AR195626A1 (en, 2012) |
| AT (1) | AT329555B (en, 2012) |
| AU (1) | AU476519B2 (en, 2012) |
| BE (1) | BE803520A (en, 2012) |
| BG (1) | BG21220A3 (en, 2012) |
| CA (1) | CA998397A (en, 2012) |
| CH (1) | CH588475A5 (en, 2012) |
| CS (1) | CS179425B2 (en, 2012) |
| DD (1) | DD110272A5 (en, 2012) |
| DE (1) | DE2340409A1 (en, 2012) |
| ES (1) | ES417837A1 (en, 2012) |
| FR (1) | FR2196336B1 (en, 2012) |
| GB (1) | GB1435809A (en, 2012) |
| HU (1) | HU166844B (en, 2012) |
| IE (1) | IE37949B1 (en, 2012) |
| IL (1) | IL42843A (en, 2012) |
| NL (1) | NL179380C (en, 2012) |
| PH (1) | PH10552A (en, 2012) |
| PL (1) | PL89385B1 (en, 2012) |
| RO (1) | RO73460A (en, 2012) |
| SE (1) | SE402913B (en, 2012) |
| SU (1) | SU576935A3 (en, 2012) |
| YU (1) | YU36513B (en, 2012) |
| ZA (1) | ZA735075B (en, 2012) |
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 |
| JP5319755B2 (ja) * | 2009-03-11 | 2013-10-16 | 日本曹達株式会社 | １−アルキル−５−ベンゾイル−１ｈ−テトラゾール誘導体の製造方法 |
| 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 (en, 2012) * |
-
1973
- 1973-07-25 ZA ZA00735075A patent/ZA735075B/xx unknown
- 1973-07-25 IE IE1268/73A patent/IE37949B1/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 HU HUEI490A patent/HU166844B/hu unknown
- 1973-08-10 BE BE1005292A patent/BE803520A/xx unknown
- 1973-08-10 AT AT703773A patent/AT329555B/de not_active IP Right Cessation
- 1973-08-13 ES ES417837A patent/ES417837A1/es not_active Expired
- 1973-08-13 KR KR7301319A patent/KR780000071B1/ko not_active Expired
- 1973-08-13 GB GB3813273A patent/GB1435809A/en not_active Expired
- 1973-08-13 SE SE7311051A patent/SE402913B/xx unknown
- 1973-08-13 PL PL1973164647A patent/PL89385B1/pl unknown
- 1973-08-13 SU SU7301955734A patent/SU576935A3/ru active
- 1973-08-14 CS CS7300005736A patent/CS179425B2/cs unknown
- 1973-08-14 NL NLAANVRAGE7311222,A patent/NL179380C/xx not_active IP Right Cessation
- 1973-08-14 FR FR7329649A patent/FR2196336B1/fr not_active Expired
- 1973-08-14 DD DD172890A patent/DD110272A5/xx unknown
- 1973-08-14 JP JP48091225A patent/JPS5821628B2/ja not_active Expired
- 1973-08-14 BG BG024317A patent/BG21220A3/xx unknown
- 1973-08-14 CH CH1171373A patent/CH588475A5/xx not_active IP Right Cessation
- 1973-08-14 AR AR249586A patent/AR195626A1/es active
- 1973-08-14 RO RO7375793A patent/RO73460A/ro unknown
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