GB1470210A - Organometallic derivatives of penicillin - Google Patents
Organometallic derivatives of penicillinInfo
- Publication number
- GB1470210A GB1470210A GB4693274A GB4693274A GB1470210A GB 1470210 A GB1470210 A GB 1470210A GB 4693274 A GB4693274 A GB 4693274A GB 4693274 A GB4693274 A GB 4693274A GB 1470210 A GB1470210 A GB 1470210A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penicillin
- acid
- complex
- prepared
- organometallic complex
- 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
- 229930182555 Penicillin Natural products 0.000 title abstract 5
- 229940049954 penicillin Drugs 0.000 title abstract 5
- 125000002524 organometallic group Chemical group 0.000 title abstract 2
- -1 -CHO Chemical group 0.000 abstract 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound 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 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000002960 penicillins Chemical class 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 abstract 1
- 229960003805 amantadine Drugs 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- DUMROMGSFPYPHA-UHFFFAOYSA-N cyclopenta-1,3-diene 2-cyclopenta-1,4-dien-1-yl-2-methylpropanoic acid iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.CC(C)(C(O)=O)[c-]1cccc1 DUMROMGSFPYPHA-UHFFFAOYSA-N 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 abstract 1
- 229910052718 tin Inorganic materials 0.000 abstract 1
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- 150000003624 transition metals Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1470210 Organometallic complex derivatives of penicillin E I EDWARDS R EPTON and G MARR 29 Oct 1975 [30 Oct 1974 29 April 1975] 46932/74 and 17853/75 Heading C2J [Also in Division C3] A semi-synthetic penicillin having at least one #-aromatic organometallic complex of a transition metal attached to an optionally substituted penicillin residue is prepared by condensing a carboxylic acid derivative of the complex with a 6-amino-penicillanic acid, the condensation being effected optionally in the presence of an amine and either by initially converting the complex acid to the acid chloride by reaction with PCl 3 or by mixing the complex acid with dicyclohexylcarbodiimide. Pharmaceutically acceptable salts of the penicillin derivatives may be prepared by subsequent reaction with sodium 2-ethylhexanoate or an amine such as benzylamine, cyclohexylamine or adamantanamine. The semi-synthetic penicillin may be of formula where M is a #-aromatic organometallic complex such as ferrocene, #-cyclopentadienyl Mn(CO) 3 or #-benzene Cr(CO) 3 which may be substituted in the ring (or rings) by organic or functional groups (linked directly or indirectly) a group -MeR 3 where Me is Si, Ge or Sn and R is C 1-4 alkyl, or by another penicillin residue, and L is a direct bond or a linking group such as ortho-phenylene, -[C(R<SP>1</SP>)(R<SP>2</SP>)] n - or where n is 0, 1 or 2 and R<SP>1</SP> and R<SP>2</SP> are each H, alkyl, aryl, alkaryl, aralkyl, alkoxy, -CHO, -COOH, -CHN 2 (CH 3 ) 2 , -NH 2 , -CH 2 SH, -CH 2 I, -COCH 2 Z (Z is Cl, Br or I) or -MeR 3 (see above) or K<SP>1</SP> and R<SP>2</SP> together with the C atom to which they are attached form a carbon ring. A number of ferrocene-containing penicillanic acids and salts are prepared in the examples and the intermediate compounds 2- ferrocenyl - 2 - methylpropionic acid, (ferrocenyl) (methoxy) acetic acid and ferrocenylcyclopropane carboxylic acid are obtained from the corresponding nitriles.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4693274A GB1470210A (en) | 1974-10-30 | 1974-10-30 | Organometallic derivatives of penicillin |
| US05/624,405 US4046903A (en) | 1974-10-30 | 1975-10-20 | Organometallic derivatives of penicillin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4693274A GB1470210A (en) | 1974-10-30 | 1974-10-30 | Organometallic derivatives of penicillin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1470210A true GB1470210A (en) | 1977-04-14 |
Family
ID=10443120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4693274A Expired GB1470210A (en) | 1974-10-30 | 1974-10-30 | Organometallic derivatives of penicillin |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1470210A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996035698A1 (en) * | 1995-05-10 | 1996-11-14 | Universite Des Sciences Et Technologies De Lille | Antimalarial organometallic iron complexes |
-
1974
- 1974-10-30 GB GB4693274A patent/GB1470210A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996035698A1 (en) * | 1995-05-10 | 1996-11-14 | Universite Des Sciences Et Technologies De Lille | Antimalarial organometallic iron complexes |
| FR2733985A1 (en) * | 1995-05-10 | 1996-11-15 | Univ Lille Sciences Tech | ORGANOMETALLIC COMPLEXES OF ANTIMALARIAL IRON |
| US6127543A (en) * | 1995-05-10 | 2000-10-03 | Universite Des Sciences Et Technologies De Lille | Antimalarial organometallic iron complexes |
| AP953A (en) * | 1995-05-10 | 2001-04-02 | Univ Des Sciences Et Technologies De Lille | Antimalarial organometallic iron complexes. |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |