IL37476A - 6-(1,2,5-thiadiazolyloxyacetyl)-aminopenicillanic acids and their preparation - Google Patents

6-(1,2,5-thiadiazolyloxyacetyl)-aminopenicillanic acids and their preparation

Info

Publication number: IL37476A
Authority: IL; Israel
Prior art keywords: acid; salts; preparation; general formula; stands
Prior art date: 1970-08-12

Application number

IL37476A

Other languages

English (en)

Other versions

IL37476A0 (en

Original Assignee

Inoin Gyogyszer Es Vegyeszeti

Priority date (The priority date 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 date listed.)

1970-08-12

Filing date

1971-08-09

Publication date

1974-10-22

1971-08-09 Application filed by Inoin Gyogyszer Es Vegyeszeti filed Critical Inoin Gyogyszer Es Vegyeszeti

1971-11-29 Publication of IL37476A0 publication Critical patent/IL37476A0/xx

1974-10-22 Publication of IL37476A publication Critical patent/IL37476A/en

Links

239000002253 acid Substances 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 5
150000007513 acids Chemical class 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
239000013543 active substance Substances 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
239000007787 solid Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
230000035945 sensitivity Effects 0.000 description 4
241001660259 Cereus <cactus> Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 description 2
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000194032 Enterococcus faecalis Species 0.000 description 1
DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
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 description 1
241000588653 Neisseria Species 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
241000194017 Streptococcus Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
241001312524 Streptococcus viridans Species 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)

IL37476A 1970-08-12 1971-08-09 6-(1,2,5-thiadiazolyloxyacetyl)-aminopenicillanic acids and their preparation IL37476A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUCI001024		1970-08-12

Publications (2)

Publication Number	Publication Date
IL37476A0 IL37476A0 (en)	1971-11-29
IL37476A true IL37476A (en)	1974-10-22

Family

ID=10994388

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL37476A IL37476A (en)	1970-08-12	1971-08-09	6-(1,2,5-thiadiazolyloxyacetyl)-aminopenicillanic acids and their preparation

Country Status (10)

Country	Link
US (1)	US3816411A (fr)
AU (1)	AU458881B2 (fr)
BE (1)	BE771236A (fr)
DK (1)	DK132277C (fr)
ES (1)	ES394132A1 (fr)
FR (1)	FR2102209B1 (fr)
GB (1)	GB1319204A (fr)
IL (1)	IL37476A (fr)
NL (1)	NL7111114A (fr)
SE (1)	SE375098B (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB957570A (en) *	1961-05-03	1964-05-06	Smith Kline French Lab	Heterocyclic antimicrobial agents and processes for their preparation

1971
- 1971-08-09 IL IL37476A patent/IL37476A/en unknown
- 1971-08-10 AU AU32174/71A patent/AU458881B2/en not_active Expired
- 1971-08-10 SE SE7110209A patent/SE375098B/xx unknown
- 1971-08-11 DK DK392071A patent/DK132277C/da active
- 1971-08-11 GB GB3776971A patent/GB1319204A/en not_active Expired
- 1971-08-11 FR FR7129362A patent/FR2102209B1/fr not_active Expired
- 1971-08-11 ES ES394132A patent/ES394132A1/es not_active Expired
- 1971-08-12 BE BE771236A patent/BE771236A/fr unknown
- 1971-08-12 NL NL7111114A patent/NL7111114A/xx unknown
- 1971-08-12 US US00171397A patent/US3816411A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DK132277B (da)	1975-11-17
BE771236A (fr)	1971-12-16
FR2102209A1 (fr)	1972-04-07
AU3217471A (en)	1973-02-15
NL7111114A (fr)	1972-02-15
ES394132A1 (es)	1974-04-01
SE375098B (fr)	1975-04-07
IL37476A0 (en)	1971-11-29
AU458881B2 (en)	1975-03-13
GB1319204A (en)	1973-06-06
US3816411A (en)	1974-06-11
DK132277C (da)	1976-04-20
FR2102209B1 (fr)	1975-06-06

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