IE37961B1 - 6-(alpha-(amidino-and imidoylaminoalkanoylamino)penicillanic acids - Google Patents
6-(alpha-(amidino-and imidoylaminoalkanoylamino)penicillanic acidsInfo
- Publication number
- IE37961B1 IE37961B1 IE1303/73A IE130373A IE37961B1 IE 37961 B1 IE37961 B1 IE 37961B1 IE 1303/73 A IE1303/73 A IE 1303/73A IE 130373 A IE130373 A IE 130373A IE 37961 B1 IE37961 B1 IE 37961B1
- Authority
- IE
- Ireland
- Prior art keywords
- hydrochloride
- alkylene
- prepared
- acid
- penicillins
- Prior art date
Links
Classifications
-
- 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
-
- 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
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]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27706472A | 1972-08-02 | 1972-08-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37961L IE37961L (en) | 1974-02-02 |
| IE37961B1 true IE37961B1 (en) | 1977-11-23 |
Family
ID=23059254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1303/73A IE37961B1 (en) | 1972-08-02 | 1973-07-31 | 6-(alpha-(amidino-and imidoylaminoalkanoylamino)penicillanic acids |
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 CA CA177,719A patent/CA1015355A/en not_active Expired
- 1973-07-31 FR FR7327954A patent/FR2194415B1/fr not_active Expired
- 1973-07-31 IE IE1303/73A patent/IE37961B1/en unknown
- 1973-07-31 FI FI2405/73A patent/FI56840C/en active
- 1973-08-01 DK DK422873AA patent/DK137047B/en not_active IP Right Cessation
- 1973-08-01 ES ES417461A patent/ES417461A1/en not_active Expired
- 1973-08-01 YU YU2086/73A patent/YU36966B/en unknown
- 1973-08-01 ZA ZA735236A patent/ZA735236B/en unknown
- 1973-08-01 NO NO3091/73A patent/NO144831C/en unknown
- 1973-08-01 SU SU7301949310A patent/SU576944A3/en active
- 1973-08-01 HU HUPI392A patent/HU167653B/hu unknown
- 1973-08-01 DD DD172673A patent/DD106849A5/xx unknown
- 1973-08-01 BE BE1005272A patent/BE803094A/en not_active IP Right Cessation
- 1973-08-02 PL PL1973164483A patent/PL96500B1/en unknown
- 1973-08-02 CS CS5498A patent/CS168459B2/cs unknown
- 1973-08-02 JP JP8646073A patent/JPS5318039B2/ja not_active Expired
- 1973-08-02 LU LU68143A patent/LU68143A1/xx unknown
- 1973-08-02 BG BG7300024251A patent/BG25798A3/en unknown
- 1973-08-02 RO RO7387460A patent/RO68719A2/en unknown
- 1973-08-02 RO RO7300075697A patent/RO63748A/en unknown
- 1973-08-02 AT AT680773A patent/AT327382B/en active
- 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 CH CH1124373A patent/CH574447A5/xx not_active IP Right Cessation
-
1975
- 1975-10-16 PH PH17666A patent/PH12770A/en unknown
- 1975-11-03 SU SU7502185959A patent/SU576945A3/en active
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