GB1377642A - Penicillanic and cephalosporanic acid derivatives - Google Patents
Penicillanic and cephalosporanic acid derivativesInfo
- Publication number
- GB1377642A GB1377642A GB196071A GB196071A GB1377642A GB 1377642 A GB1377642 A GB 1377642A GB 196071 A GB196071 A GB 196071A GB 196071 A GB196071 A GB 196071A GB 1377642 A GB1377642 A GB 1377642A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- hydrogen
- alkyl
- phenyl
- penicillanic
- 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
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 title abstract 3
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 title abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000002902 organometallic compounds Chemical class 0.000 abstract 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- -1 amine salts Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical group [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 abstract 2
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000005263 alkylenediamine group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000004429 atom Chemical group 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
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000686 lactone group Chemical group 0.000 abstract 1
- 150000002596 lactones Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 150000002641 lithium Chemical group 0.000 abstract 1
- 229910001623 magnesium bromide Chemical group 0.000 abstract 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000012454 non-polar solvent Substances 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- KZHAHJANVBGCOC-UHFFFAOYSA-N phenyl hypochlorite Chemical compound ClOC1=CC=CC=C1 KZHAHJANVBGCOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1377642 Penicillins and cephalosporins KONINKLIJKE NEDERLANDSCHE GISTEN SPIRITUSFABRIEK NV 13 Jan 1972 [14 Jan 1971] 1960/71 Heading C2C [Also in Division C3] Novel penicillanic and cephalosporanic acid derivatives having the general Formulµ (I) and (II) and alkali metal, alkaline earth metal and amine salts thereof, wherein R is hydrogen, -OH or C 1 to C 4 alkanoyloxy, or the group -OH 2 R and -COOH in Formula II are linked to form a lactone group; R 1 and R 2 are the same or different and each is hydrogen, C 1 to C 4 alkyl, C 1 to C 4 alkoxy, C 5 to C 8 cycloalkyl, phenyl, phenoxy, chlorine or fluorine, or R 1 and R 2 together with the attached carbon atoms form a phenyl group or cycloalkylene group having at least one double bond, these groups optionally being substituted; R 3 is hydrogen, C 1 to C 4 alkyl, vinyl, allyl, C 5 to C 8 cycloalkyl, phenyl (C 1 to C 4 ) alkyl, or phenyl optionally substituted by one or more of C 1 to C 4 alkyl or alkoxy or chlorine; R 4 and R 5 are the same or different and each is hydrogen or C 1 to C 4 alkyl, or R 4 and R 5 together represent a keto oxygen; and n is zero or 1; are prepared by reacting an organo-metallic heterocyclic compound of Formula III wherein R 1 to R 5 are as before and X is a lithium atom or a magnesium chloride (-MgCl) or magnesium bromide (-MgBr) group, with an ester of 6-isocyanatopenicillanic acid or an ester or lactone of 7-isocyanatocephalosporanic acid, said acids having the Formulµ IV respectively, wherein R<SP>1</SP> is hydrogen, C 1-4 alkanoyloxy or a protected hydroxy group; and hydrolysing the resulting product to remove the metal atom and the esterifying group (and the hydroxy-protecting group if present). The organo-metallic compound (III) is prepared by reacting a compound of Formula III in which X is hydrogen with either (i) nbutyllithium, ethylmagnesium bromide or isopropylmagnesium chloride in an aprotic polar solvent (e.g. tetrahydrofuran) at - 40‹ to - 80‹ C.; or (ii) a complex of n-butyllithium and an N,N,N<SP>1</SP>,N<SP>1</SP>-tetrasubstituted alkylenediamine in a non-polar solvent (e.g. toluene). Pharmaceutical compositions having broad spectrum anti-bacterial activity comprise a penicillanic or cephalosporanic acid derivative of Formula I or II or an appropriate salt thereof, together with a pharmaceutically acceptable carrier.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB196071A GB1377642A (en) | 1971-01-14 | 1971-01-14 | Penicillanic and cephalosporanic acid derivatives |
| NL7200486A NL7200486A (en) | 1971-01-14 | 1972-01-13 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB196071A GB1377642A (en) | 1971-01-14 | 1971-01-14 | Penicillanic and cephalosporanic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1377642A true GB1377642A (en) | 1974-12-18 |
Family
ID=9731087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB196071A Expired GB1377642A (en) | 1971-01-14 | 1971-01-14 | Penicillanic and cephalosporanic acid derivatives |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB1377642A (en) |
| NL (1) | NL7200486A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1479676A1 (en) * | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | Benzimidazole-derivatives as factor xa inhibitors |
| US7470700B2 (en) | 2003-08-13 | 2008-12-30 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7550590B2 (en) | 2003-03-25 | 2009-06-23 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7741341B2 (en) | 2003-05-19 | 2010-06-22 | Sanofi-Aventis Deutschland Gmbh | Benzimidazole-derivatives as factor Xa inhibitors |
| US7781584B2 (en) | 2004-03-15 | 2010-08-24 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7790734B2 (en) | 2003-09-08 | 2010-09-07 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7872124B2 (en) | 2004-12-21 | 2011-01-18 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8084605B2 (en) | 2006-11-29 | 2011-12-27 | Kelly Ron C | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
| US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
| US8222411B2 (en) | 2005-09-16 | 2012-07-17 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8906901B2 (en) | 2005-09-14 | 2014-12-09 | Takeda Pharmaceutical Company Limited | Administration of dipeptidyl peptidase inhibitors |
-
1971
- 1971-01-14 GB GB196071A patent/GB1377642A/en not_active Expired
-
1972
- 1972-01-13 NL NL7200486A patent/NL7200486A/xx unknown
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7550590B2 (en) | 2003-03-25 | 2009-06-23 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7687625B2 (en) * | 2003-03-25 | 2010-03-30 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7741341B2 (en) | 2003-05-19 | 2010-06-22 | Sanofi-Aventis Deutschland Gmbh | Benzimidazole-derivatives as factor Xa inhibitors |
| EP1479676A1 (en) * | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | Benzimidazole-derivatives as factor xa inhibitors |
| US7470700B2 (en) | 2003-08-13 | 2008-12-30 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7579357B2 (en) | 2003-08-13 | 2009-08-25 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7723344B2 (en) | 2003-08-13 | 2010-05-25 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| US7790736B2 (en) | 2003-08-13 | 2010-09-07 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7790734B2 (en) | 2003-09-08 | 2010-09-07 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7807689B2 (en) | 2004-03-15 | 2010-10-05 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7781584B2 (en) | 2004-03-15 | 2010-08-24 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7906523B2 (en) | 2004-03-15 | 2011-03-15 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8173663B2 (en) | 2004-03-15 | 2012-05-08 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8188275B2 (en) | 2004-03-15 | 2012-05-29 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8288539B2 (en) | 2004-03-15 | 2012-10-16 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8329900B2 (en) | 2004-03-15 | 2012-12-11 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7872124B2 (en) | 2004-12-21 | 2011-01-18 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8906901B2 (en) | 2005-09-14 | 2014-12-09 | Takeda Pharmaceutical Company Limited | Administration of dipeptidyl peptidase inhibitors |
| US8222411B2 (en) | 2005-09-16 | 2012-07-17 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8084605B2 (en) | 2006-11-29 | 2011-12-27 | Kelly Ron C | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
| US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7200486A (en) | 1972-07-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |