GB1418656A - 6-alpha-amidino-and imidoylaminoalkanoyl-amino-penicillanic acids - Google Patents
6-alpha-amidino-and imidoylaminoalkanoyl-amino-penicillanic acidsInfo
- Publication number
- GB1418656A GB1418656A GB5971172A GB5971172A GB1418656A GB 1418656 A GB1418656 A GB 1418656A GB 5971172 A GB5971172 A GB 5971172A GB 5971172 A GB5971172 A GB 5971172A GB 1418656 A GB1418656 A GB 1418656A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrochloride
- alkylene
- prepared
- acid
- amino
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 239000002253 acid Substances 0.000 title abstract 2
- 150000007513 acids Chemical class 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 6
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 229930182555 Penicillin Natural products 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000002960 penicillins Chemical class 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
- BTZMKYDRWKUERF-UHFFFAOYSA-N 2-(4,5-dihydroimidazol-1-yl)acetic acid;hydrochloride Chemical compound Cl.OC(=O)CN1CCN=C1 BTZMKYDRWKUERF-UHFFFAOYSA-N 0.000 abstract 1
- OQBWVGWIZGYYCZ-UHFFFAOYSA-N 2-(aminomethylideneamino)acetyl chloride;hydrochloride Chemical compound Cl.ClC(=O)CNC=N OQBWVGWIZGYYCZ-UHFFFAOYSA-N 0.000 abstract 1
- JMQGOPFWDGSLKM-UHFFFAOYSA-N 2-[(1-amino-2-methylpropylidene)amino]acetic acid;hydrochloride Chemical compound Cl.CC(C)C(=N)NCC(O)=O JMQGOPFWDGSLKM-UHFFFAOYSA-N 0.000 abstract 1
- HMRCCGFILBNRKU-UHFFFAOYSA-N 2-[[amino(phenyl)methylidene]amino]acetyl chloride;hydrochloride Chemical compound Cl.ClC(=O)CNC(=N)C1=CC=CC=C1 HMRCCGFILBNRKU-UHFFFAOYSA-N 0.000 abstract 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- JQDMLIASGZNNSY-UHFFFAOYSA-N 3-(4,5-dihydroimidazol-1-yl)propanoic acid;hydrochloride Chemical compound Cl.OC(=O)CCN1CCN=C1 JQDMLIASGZNNSY-UHFFFAOYSA-N 0.000 abstract 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- ZBRAQBFYFWXCGD-UHFFFAOYSA-N 4-amino-4-iminobutanoic acid;hydrochloride Chemical compound Cl.NC(=N)CCC(O)=O ZBRAQBFYFWXCGD-UHFFFAOYSA-N 0.000 abstract 1
- CPKVWQIHWUBWJG-UHFFFAOYSA-N 4-amino-4-iminobutanoyl chloride;hydrochloride Chemical compound Cl.NC(=N)CCC(Cl)=O CPKVWQIHWUBWJG-UHFFFAOYSA-N 0.000 abstract 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000001118 alkylidene group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- AUYABQKPUHQTOC-UHFFFAOYSA-N benzyl 2-(4,5-dihydroimidazol-1-yl)acetate Chemical compound C=1C=CC=CC=1COC(=O)CN1CCN=C1 AUYABQKPUHQTOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- LWNZWFFRNHYXPX-UHFFFAOYSA-N ethyl 2-methylpropanimidate;hydrochloride Chemical compound Cl.CCOC(=N)C(C)C LWNZWFFRNHYXPX-UHFFFAOYSA-N 0.000 abstract 1
- YPCIAPYFQQPVMR-UHFFFAOYSA-N ethyl 3-(ethylamino)-3-oxopropanoate Chemical compound CCNC(=O)CC(=O)OCC YPCIAPYFQQPVMR-UHFFFAOYSA-N 0.000 abstract 1
- MQYCBOANPAANDZ-UHFFFAOYSA-N ethyl 3-[ethyl(methyl)amino]-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)N(C)CC MQYCBOANPAANDZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- BPSKURPOKFSLHJ-UHFFFAOYSA-N methyl 3-cyanopropanoate Chemical compound COC(=O)CCC#N BPSKURPOKFSLHJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- -1 pyrryl Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1719/CAL/73A IN138817B (cs) | 1972-12-27 | 1973-07-23 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27706472A | 1972-08-02 | 1972-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1418656A true GB1418656A (en) | 1975-12-24 |
Family
ID=23059254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5971172A Expired GB1418656A (en) | 1972-08-02 | 1972-12-27 | 6-alpha-amidino-and imidoylaminoalkanoyl-amino-penicillanic acids |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS5318039B2 (cs) |
| AR (1) | AR206879A1 (cs) |
| AT (1) | AT327382B (cs) |
| AU (1) | AU472676B2 (cs) |
| BE (1) | BE803094A (cs) |
| BG (1) | BG25798A3 (cs) |
| CA (1) | CA1015355A (cs) |
| CH (1) | CH574447A5 (cs) |
| CS (1) | CS168459B2 (cs) |
| DD (1) | DD106849A5 (cs) |
| DE (1) | DE2338389A1 (cs) |
| DK (1) | DK137047B (cs) |
| EG (1) | EG10896A (cs) |
| ES (1) | ES417461A1 (cs) |
| FI (1) | FI56840C (cs) |
| FR (1) | FR2194415B1 (cs) |
| GB (1) | GB1418656A (cs) |
| HU (1) | HU167653B (cs) |
| IE (1) | IE37961B1 (cs) |
| IL (1) | IL42820A (cs) |
| LU (1) | LU68143A1 (cs) |
| NL (1) | NL7310696A (cs) |
| NO (1) | NO144831C (cs) |
| PH (1) | PH12770A (cs) |
| PL (1) | PL96500B1 (cs) |
| RO (2) | RO68719A2 (cs) |
| SE (1) | SE415977B (cs) |
| SU (2) | SU576944A3 (cs) |
| YU (1) | YU36966B (cs) |
| ZA (1) | ZA735236B (cs) |
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/es active
- 1973-07-09 SE SE7309644A patent/SE415977B/xx 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/de not_active Withdrawn
- 1973-07-31 CA CA177,719A patent/CA1015355A/en not_active Expired
- 1973-07-31 FI FI2405/73A patent/FI56840C/fi active
- 1973-07-31 IE IE1303/73A patent/IE37961B1/xx unknown
- 1973-07-31 FR FR7327954A patent/FR2194415B1/fr not_active Expired
- 1973-08-01 BE BE1005272A patent/BE803094A/xx not_active IP Right Cessation
- 1973-08-01 SU SU7301949310A patent/SU576944A3/ru active
- 1973-08-01 ZA ZA735236A patent/ZA735236B/xx unknown
- 1973-08-01 ES ES417461A patent/ES417461A1/es not_active Expired
- 1973-08-01 DK DK422873AA patent/DK137047B/da not_active IP Right Cessation
- 1973-08-01 DD DD172673A patent/DD106849A5/xx unknown
- 1973-08-01 HU HUPI392A patent/HU167653B/hu unknown
- 1973-08-01 YU YU2086/73A patent/YU36966B/xx unknown
- 1973-08-01 NO NO3091/73A patent/NO144831C/no unknown
- 1973-08-02 RO RO7387460A patent/RO68719A2/ro unknown
- 1973-08-02 LU LU68143A patent/LU68143A1/xx unknown
- 1973-08-02 AT AT680773A patent/AT327382B/de active
- 1973-08-02 CH CH1124373A patent/CH574447A5/xx not_active IP Right Cessation
- 1973-08-02 PL PL1973164483A patent/PL96500B1/pl unknown
- 1973-08-02 RO RO7300075697A patent/RO63748A/ro unknown
- 1973-08-02 NL NL7310696A patent/NL7310696A/xx not_active Application Discontinuation
- 1973-08-02 EG EG298/73A patent/EG10896A/xx active
- 1973-08-02 BG BG024251A patent/BG25798A3/xx unknown
- 1973-08-02 JP JP8646073A patent/JPS5318039B2/ja not_active Expired
- 1973-08-02 CS CS5498A patent/CS168459B2/cs unknown
-
1975
- 1975-10-16 PH PH17666A patent/PH12770A/en unknown
- 1975-11-03 SU SU7502185959A patent/SU576945A3/ru active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |