IL42820A - 6-(2-phenyl(or thienyl)-2-(amidino(or imidoylamino)-alkanoylamino)acetamido)-penicillanic acids and their preparation - Google Patents
6-(2-phenyl(or thienyl)-2-(amidino(or imidoylamino)-alkanoylamino)acetamido)-penicillanic acids and their preparationInfo
- Publication number
- IL42820A IL42820A IL42820A IL4282073A IL42820A IL 42820 A IL42820 A IL 42820A IL 42820 A IL42820 A IL 42820A IL 4282073 A IL4282073 A IL 4282073A IL 42820 A IL42820 A IL 42820A
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- IL
- Israel
- Prior art keywords
- compound
- hydrochloride
- phenyl
- formula
- hydrogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1418656 Penicillins PFIZER Inc 27 Dec 1972 [2 Aug 1972] 59711/72 Heading C2C Novel penicillins having the Formula (I) or (II) and salts thereof, wherein Ar is phenyl, 4- hydroxyphenyl or 2- or 3-thienyl; A is 1,4- phenylene, C 1 -C 3 alkylene or C 2 -C 3 alkylidene; R 1 and R 2 are each hydrogen, C 1 -C 3 alkyl; naphthyl, thienyl, pyrryl, pyridyl, furyl, phenyl, benzyl, or substituted phenyl or benzyl wherein the substituent is Cl, Br, F, CH 3 , CH 3 O, CF 3 , 3,4-dichloro or 3,5-dichloro; or R 1 and R 2 together are C 2 -C 6 alkylene; and R 2 and R 3 together can be C 2 -C 4 alkylene, and R 2 and R 4 together can be C 3 -C 5 alkylene; are prepared by reacting an appropriate α-amino arylacetamido-penicillin or a salt thereof with a compound of formula wherein R is X is OH or Cl, and R 1 , R 2 , R 3 and R 4 are as defined above, in the presence of a condensing agent or acid binding agent respectively. The penicillins (I) and (II) have antibiotic activity, and may be made up into antibacterially active pharmaceutical compositions with conventional pharmaceutical diluents or carriers. The following starting materials and intermediates are also prepared: 3-amidinopropionic acid hydrochloride is produced by reacting methanol, methyl-3-cyanopropionate and HCl to give methyl #-carbomethoxypropionamidate hydrochloride which is treated with ammonia to give #-carbomethoxypropionamidine hydrochloride, the latter then being hydrolysed with 12N hydrochloric acid. By analogous procedure, many other compounds of formula where R 1 , R 2 , R 3 and A are as defined above, are prepared. N,N<SP>1</SP> - Diethylamidinoacetic acid hydrochloride is prepared via N-ethyl-carboethoxyacetamide, methyl N - ethyl - carboethoxyacetamide and N,N<SP>1</SP> - diethyl - carboethoxyacetamidine hydrochloride. Other analogues wherein R 1 , R 2 , R 3 and A are as before are similarly produced. Other compounds produced are 3-(2-imidazolinyl)propionic acid hydrochloride, 3-amidinopropionyl chloride hydrochloride, ethyl isobutyrimidate hydrochloride, isobutyrimidoylaminoacetic acid hydrochloride and the corresponding free base; N - (N<SP>1</SP> - methylacetimidoyl)aminoacetic hydrochloride, 2 - (N - n - propyl - N - carboxymethyl)amino - 1 - aza - cyclohept - 2 - ene hydrochloride, N - carboxymethylimidazoline hydrochloride, N - carbobenzyloxymethyl - imidazoline; formimidoylaminoacetyl chloride hydrochloride; and benzimidoylaminoacetyl chloride hydrochloride.
[GB1418656A]
Description
acids nd preparation and However none of the heterocyclyl radicals in the above mentioned known compounds contains two nitrogen as in the amidino and imidoylamino derivatives according to the present and the pharmaceutically acceptable basic salts wherein Ar is or A is phenylene or straight or branched alkylene containing from 1 to 3 carbon and when considered separately are each hydrogen or alkyl containing from 1 to 3 carbon and are each alkyl containing from 1 to 3 carbon benzyl or substituted phenyl or benzyl wherein said substituent is bromo trifluoromethyl or 3 and when considered together are alkylene containing from 2 to 6 carbon and and when considered together are alkylene containing from 3 to 5 carbon are particularly active against a broad spectrum of especially A preferred group of congeners the present invention are those of formula I wherein Ar is A is alkylene containing from 1 to 3 carbon atoms and and are each accordance with the process employed for synthesizing the lins of the present invention two preparative routes are The first is illu 2 1 II In the requisite amine salt and acid chloride wherein and are previously are contacted in a solvent in the presence of a hydrogen halide such as a tertiary subcutraneously For parenteral they are best used the fo of a sterile aqueous solution which may be either aqueous such as tonic isotonic or such as fatty oils of vegetable origin peanut and other vehicles which will not interfere with the therapeutic efficiency of the preparation and are nontoxic in the volume or proportion us propylene compositions suitable for extemporaneous preparation of solutions prior to administration may advan tageously be Such compositions may include liquid for exampl propylene diethyl buffering as well as local anesthetics and inorganic salts to afford desirable pharmacological The following examples are provided solely for the purpose of illus tration and are not to be construed as limitations of this many variations of which are possible without departing from the spirit or scope thereof 1 ace acid Ar A and To 10 of dry at room temperature and maintai under a nitrogen atmosphere is added in of of dicyclohexylcarbodiiraide and S30 m of and the mixture allowed to stir for triethylamine 4 m is added to th yellow suspension and the mixture allowed to stir overnight at ambient tempe The solids are filtered and the clear filtrate poured into 200 o diethyl The precipitated yellow product is filtered and suspended in 100 of methylene to which is added 2 of Aft stirring for 1 the purified product is filtered and dried in 910 Infrared spectrum peaks and Nuclear magnetic resonance spectrum peaks and EXAMPLE 2 jj acid Ar A R and a suspension of m of triethylanine salt in 15 of dry diraethylformamide maintained under nitro V is added m of triethylamine and the mixture cooled in a penicillanic i D Θ product is filtered and dried chloride After stirring in the cold for 45 of the acid chloride is after 45 by the addition of 3 of Alternate additions are continued at 45 intervals until a total of of acid chloride and of triethylamine has been to the penicillanic penicillanic penicillani penicillanic acid luoromethy penicillanic d triethylanine salt in 85 of dry is cooled to in a sal ice bath subsequently treated 985 of 2 chloride hydrochloride and of After 30 of continued stirring and cooling an additional 985 of acid chloride and of are added and the mixture stirred for one The ice bath is then removed and the reactio mixture allowed to to room and stir for 45 The solids i are filtered and the clear filtrate is added dropwise to 1 of diethyl ether vigorous The crude product is filtered and suspended in 20 of methylene chloride containing 3 of triethylaraine After stirring at room temperature for 5 the purified product is washed diethyl ether and dried in vacuo EXAMPLE 18 the procedure of and starting the appropriate acid chloride and the congeners Example 26 acid dihydrochloride A mixture of of glycine and 97 of methyl imidate in 100 of amyl alcohol is heated to reflux for 3 The solids are filtered while the reaction mixture is hot and are quently washed with amyl alcohol x 100 and diethyl ether x 100 Drying overnight under nitrogen provides of the sired Ten grams of acid in 50 of diethyl ether is treated ith sufficient hydrogen chloride gas to vide the dihydrochloride To 350 of methylene chloride is added of imidoylaminoacetic acid of phosphorous chloride and of and the resulting reaction mixture allowed to stir at room temperature The yellow solid is washed successively with chloroform x 300 and hexane 1 x 300 The desired chloride chloride is dried under acid To of trihydrate in 60 of dimethyIformamide and of triethylamine contained in a 150 flask fitted with magnetic drying tube and cold temperature and cooled to is added of chloride After 30 of stirring at to an additional of triethylamine is followed after 5 by an additional of the acid Stirring is continued for 30 at to at which time of triethylamine is followed after 5 by of the acid After 45 of stirring in the cold of is added followed after 10 by of the acid Stirring is continued in the cold for 30 and then the reaction ture is allowed to warm during at 45 period to room The insolubles are filtered and washed with 20 of The solids are discarded and the washings are combined with the trate and added to 1 of The solids which precipitate are filtered and and the filtrate diluted with 2 of The resulting which is composed of a mixture of and the product is filtered and The crude product is added to 80 of methylene ride and to this suspension is with 1 of The suspension is allowed to stir 30 and is then Pure product is obtained by room temperature zation from methanol and from 325 Nuclear magentic resonance spectrum peaks and contamination In the synthesis of those intermediates where A is methylene and R3 is aryl or heterocyclic the preferred route of synthesis employs the which is conveniently removed in the final step employing dilute acid or trifluoroacetic acid at room N Acid hydrochloride i To of carboethoxyacetyl chloride in 150 of benzene is with of in 50 of the same The reaction mixture is allowed to stir at followed by The is washed with dried over sodium sulfate and concentrated to The residual product is washed several times with ether and dried n vacuo The crude product is employed in the next reaction without further hyl To a stirred solution of of carboethoxyacetamide in 20 of benzene is added of dimethyl sulfate over a period of hrs and the resulting mixture is for 16 The cooled reaction is neutralized carefully with sodium hydroxide and the organic phase separated and dried over G C2V 6 5 V 5 4 48 f and the reaction mixture allowed to stir overnigh at room The product is washed successively with methylene chloroform x hexane and dried i J Following procedures and starting with the appropriate I acid the imidoylaminoalkanoic acid chloride hydrochlorides j in the acylation of the are conveniently j E The utilized as starting reagents in Prepar tion are prepared by methods known to those skilled in the in particu the procedures of et 2214 et and et 497 j and 859 were F Amino Acids The amino acids employed as intermediates leading to the present invention are either commercial reagents or are synthesized by commonly known for according to the synthetic routes as taught by Greenstei al of the Amino John Wiley New 2 and G Haloesters The halo esters employed as intermediates are either commercial insufficientOCRQuality
Claims (25)
1. A compound selected from those of the fonaulsfS: A » II * N-R, I C=N-Rp and the pharmaceutically acceptable basic salts thereof, vherein Ar is phenyl, 2-thienyl or 3 thienyl; A is 1 ,4-phenylene or straight or branched alkylene containing from 1 to 3 carbon atoms; R^ and when considered separately are each hydrogen or alkyl containing from 1 to 3 carbon atoms; and are each hydrogen, alkyl containing from 1 to 3 carbon atoms , thienyl , furyl , pyridyl , phenyl , benzyl , substituted phenyl or substituted benzyl wherein said substituent is chloro, bromo, fluoro, methyl, methoxy, trifluoromethyl , 3,4-dichloro or 3 , 5-dichloro ; R^ and R2 when considered together are alkylene containing from 2 to 6 carbonatoms ; and R and R when considered to ether are alkylene 42820/2
2. A compound of claim 1, having the D-configuration.
3. A compound of claim 2, Formula I, wherein Ar is phenyl and ^, R2 and R^ are each hydrogen.
4. The compound of claim 3, wherein A is -CH2-.
5. The compound of claim 3, wherein A is - (CI^ 2**"
6. A compound of claim 2, Formula IX, wherein Ar is phenyl, A is -CH2-r R^ and R2 are each hydrogen and R^ is hydrogen or alkyl containing from 1 to 3 carbon atoms.
7. The compound of claim 6, wherein R^ is hydrogen.
8. The compound o claim 6, wherein ^ is methyl.
9. The compound of claim 6, wherein is ethyl.
10. The compound of claim 6, wherei RA is n-prepyl.
11. The compound of claim 6, wherein. 4 is i^propyl.
12. A compound of claim 2, Formula II, wherein Ar is phenyl, A is alk lene containing from 1 to 3 carbo atoms. and ¾ and R2 are each hydrogen.
13. The compound of claim 12, wherein A is and phenyl .
14. The compound of claim 12, wherein A is -C¾- and &4 is g-chlorophenyl.
15. The compound of claim 12, wherein A is -CH2- and R4 is p_-fluorophenyl.
16. The compound of claim 12, wherein A is -CB2- and 4 is £-bromophenyl.
17. The compound of claim 12, wherein A is -CH2- and R. is 4 2-thienyl.
18. The compound of claim 12, wherein A is -CH2- and R4 is 2-furyl.
19. The compound of claim 12, wherein A is and R. is 3 ,4-dichlorophenyl.
20. . The compound of claim 12, wherein A is -CB2- and - 42820/2
21. A process of preparing a compound of the Formulae I or II as defined in claim 1, which comprises reacting a . compound of the formula: Ar or salt thereof, wherein Ar is as defined in claim 1, with a compound of the formula: 0 If R - A - C - X whereΐηϊ wherein R-^, R2, R3 and R^ are as defined in claim 1, A is as defined in claim 1, and X is -0Π or CI, in tho presence of a scavenger to remove the elements of water or HC1, respectively, and if desired, forming the pharmaceutically acceptable basic salts thereof.
22. Compounds of the Formulae I and II as defined in claim 1, whenever prepared by the process as herein described
23. The process of preparing the compounds of Formulae I and II, as herein defined, as as herein described.
24.- A compound according--tcr-claim-2," Formula ΙΓ wherein Ar is phenyl, A is -CI^-, and R2 are each hydrogen and R^ is pyridyl.
25. A compound according to claim 2, Formula II, wherein R . is 4-pyridyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27706472A | 1972-08-02 | 1972-08-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42820A0 IL42820A0 (en) | 1973-10-25 |
| IL42820A true IL42820A (en) | 1977-06-30 |
Family
ID=23059254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42820A IL42820A (en) | 1972-08-02 | 1973-07-25 | 6-(2-phenyl(or thienyl)-2-(amidino(or imidoylamino)-alkanoylamino)acetamido)-penicillanic acids and their preparation |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS5318039B2 (en) |
| AR (1) | AR206879A1 (en) |
| AT (1) | AT327382B (en) |
| AU (1) | AU472676B2 (en) |
| BE (1) | BE803094A (en) |
| BG (1) | BG25798A3 (en) |
| CA (1) | CA1015355A (en) |
| CH (1) | CH574447A5 (en) |
| CS (1) | CS168459B2 (en) |
| DD (1) | DD106849A5 (en) |
| DE (1) | DE2338389A1 (en) |
| DK (1) | DK137047B (en) |
| EG (1) | EG10896A (en) |
| ES (1) | ES417461A1 (en) |
| FI (1) | FI56840C (en) |
| FR (1) | FR2194415B1 (en) |
| GB (1) | GB1418656A (en) |
| HU (1) | HU167653B (en) |
| IE (1) | IE37961B1 (en) |
| IL (1) | IL42820A (en) |
| LU (1) | LU68143A1 (en) |
| NL (1) | NL7310696A (en) |
| NO (1) | NO144831C (en) |
| PH (1) | PH12770A (en) |
| PL (1) | PL96500B1 (en) |
| RO (2) | RO68719A2 (en) |
| SE (1) | SE415977B (en) |
| SU (2) | SU576944A3 (en) |
| YU (1) | YU36966B (en) |
| ZA (1) | ZA735236B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4024130A (en) * | 1975-03-31 | 1977-05-17 | Pfizer Inc. | Process for the manufacture of alkali metal salts of 6-[2-phenyl-2-(imidoylaminoalkanoylamino)acetamido]penicillanic acids |
| US4073780A (en) * | 1976-06-03 | 1978-02-14 | Pfizer Inc. | 4-Pyridylformimidoylglycyl-D-phenylglycine |
-
1972
- 1972-12-27 GB GB5971172A patent/GB1418656A/en not_active Expired
-
1973
- 1973-01-01 AR AR249414A patent/AR206879A1/en active
- 1973-07-09 SE SE7309644A patent/SE415977B/en unknown
- 1973-07-24 AU AU58433/73A patent/AU472676B2/en not_active Expired
- 1973-07-25 IL IL42820A patent/IL42820A/en unknown
- 1973-07-28 DE DE19732338389 patent/DE2338389A1/en not_active Withdrawn
- 1973-07-31 FR FR7327954A patent/FR2194415B1/fr not_active Expired
- 1973-07-31 FI FI2405/73A patent/FI56840C/en active
- 1973-07-31 IE IE1303/73A patent/IE37961B1/en unknown
- 1973-07-31 CA CA177,719A patent/CA1015355A/en not_active Expired
- 1973-08-01 HU HUPI392A patent/HU167653B/hu unknown
- 1973-08-01 DD DD172673A patent/DD106849A5/xx unknown
- 1973-08-01 ZA ZA735236A patent/ZA735236B/en unknown
- 1973-08-01 ES ES417461A patent/ES417461A1/en not_active Expired
- 1973-08-01 BE BE1005272A patent/BE803094A/en not_active IP Right Cessation
- 1973-08-01 DK DK422873AA patent/DK137047B/en not_active IP Right Cessation
- 1973-08-01 NO NO3091/73A patent/NO144831C/en unknown
- 1973-08-01 SU SU7301949310A patent/SU576944A3/en active
- 1973-08-01 YU YU2086/73A patent/YU36966B/en unknown
- 1973-08-02 JP JP8646073A patent/JPS5318039B2/ja not_active Expired
- 1973-08-02 PL PL1973164483A patent/PL96500B1/en unknown
- 1973-08-02 RO RO7387460A patent/RO68719A2/en unknown
- 1973-08-02 CS CS5498A patent/CS168459B2/cs unknown
- 1973-08-02 NL NL7310696A patent/NL7310696A/xx not_active Application Discontinuation
- 1973-08-02 EG EG298/73A patent/EG10896A/en active
- 1973-08-02 LU LU68143A patent/LU68143A1/xx unknown
- 1973-08-02 CH CH1124373A patent/CH574447A5/xx not_active IP Right Cessation
- 1973-08-02 AT AT680773A patent/AT327382B/en active
- 1973-08-02 BG BG7300024251A patent/BG25798A3/en unknown
- 1973-08-02 RO RO7300075697A patent/RO63748A/en unknown
-
1975
- 1975-10-16 PH PH17666A patent/PH12770A/en unknown
- 1975-11-03 SU SU7502185959A patent/SU576945A3/en active
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