CA1269978A - Carbapenem antibiotics - Google Patents
Carbapenem antibioticsInfo
- Publication number
- CA1269978A CA1269978A CA000436924A CA436924A CA1269978A CA 1269978 A CA1269978 A CA 1269978A CA 000436924 A CA000436924 A CA 000436924A CA 436924 A CA436924 A CA 436924A CA 1269978 A CA1269978 A CA 1269978A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- carbon atoms
- phenyl
- group
- atoms
- 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 - Lifetime
Links
- 239000003242 anti bacterial agent Substances 0.000 title abstract 2
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 title abstract 2
- 229940088710 antibiotic agent Drugs 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 542
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 412
- 125000001424 substituent group Chemical group 0.000 claims abstract 397
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 204
- -1 araliphatic Chemical group 0.000 claims abstract 191
- 125000003118 aryl group Chemical group 0.000 claims abstract 101
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 97
- 229910052799 carbon Inorganic materials 0.000 claims abstract 53
- 125000002947 alkylene group Chemical group 0.000 claims abstract 34
- 125000000217 alkyl group Chemical group 0.000 claims 424
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 400
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 385
- 229910052739 hydrogen Inorganic materials 0.000 claims 307
- 239000001257 hydrogen Substances 0.000 claims 307
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 302
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 250
- 229910052757 nitrogen Inorganic materials 0.000 claims 227
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 215
- 150000001875 compounds Chemical class 0.000 claims 215
- 125000003282 alkyl amino group Chemical group 0.000 claims 212
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 204
- 125000000753 cycloalkyl group Chemical group 0.000 claims 190
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 186
- 229910052760 oxygen Inorganic materials 0.000 claims 183
- 125000005842 heteroatom Chemical group 0.000 claims 171
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 167
- 125000006239 protecting group Chemical group 0.000 claims 165
- 238000000034 method Methods 0.000 claims 164
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 154
- 125000005843 halogen group Chemical group 0.000 claims 150
- 125000004429 atom Chemical group 0.000 claims 144
- 125000004434 sulfur atom Chemical group 0.000 claims 140
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 120
- 239000001301 oxygen Substances 0.000 claims 120
- 125000000129 anionic group Chemical group 0.000 claims 115
- 150000002500 ions Chemical class 0.000 claims 105
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 99
- 125000003342 alkenyl group Chemical group 0.000 claims 96
- 125000000304 alkynyl group Chemical group 0.000 claims 96
- 125000001153 fluoro group Chemical group F* 0.000 claims 96
- 125000003710 aryl alkyl group Chemical group 0.000 claims 95
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 94
- 150000003839 salts Chemical class 0.000 claims 94
- 150000003254 radicals Chemical class 0.000 claims 92
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 88
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 67
- 125000001246 bromo group Chemical group Br* 0.000 claims 66
- 125000001309 chloro group Chemical group Cl* 0.000 claims 66
- 125000004093 cyano group Chemical group *C#N 0.000 claims 66
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 62
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 61
- 125000001118 alkylidene group Chemical group 0.000 claims 59
- 229910052717 sulfur Inorganic materials 0.000 claims 59
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 57
- 150000001721 carbon Chemical group 0.000 claims 46
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 40
- 239000002168 alkylating agent Substances 0.000 claims 38
- 229940100198 alkylating agent Drugs 0.000 claims 38
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 37
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 36
- 125000004414 alkyl thio group Chemical group 0.000 claims 34
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 32
- 125000004423 acyloxy group Chemical group 0.000 claims 27
- 125000005236 alkanoylamino group Chemical group 0.000 claims 27
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 26
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 25
- 239000007795 chemical reaction product Substances 0.000 claims 25
- 229910052736 halogen Inorganic materials 0.000 claims 20
- 150000002367 halogens Chemical class 0.000 claims 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 17
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 17
- 239000003960 organic solvent Substances 0.000 claims 17
- 125000002837 carbocyclic group Chemical group 0.000 claims 16
- 125000001475 halogen functional group Chemical group 0.000 claims 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 238000005160 1H NMR spectroscopy Methods 0.000 claims 8
- 238000001228 spectrum Methods 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 6
- 125000004954 trialkylamino group Chemical group 0.000 claims 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000003367 polycyclic group Chemical group 0.000 claims 4
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- 206010011416 Croup infectious Diseases 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 201000010549 croup Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 238000005956 quaternization reaction Methods 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 125000006243 carbonyl protecting group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/26—Radicals substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65611—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. penicillins and analogs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42575582A | 1982-09-28 | 1982-09-28 | |
| US425,755 | 1982-09-28 | ||
| US53001183A | 1983-09-09 | 1983-09-09 | |
| US530,011 | 1983-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1269978A true CA1269978A (en) | 1990-06-05 |
Family
ID=27026797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000436924A Expired - Lifetime CA1269978A (en) | 1982-09-28 | 1983-09-16 | Carbapenem antibiotics |
Country Status (29)
| Country | Link |
|---|---|
| KR (1) | KR890002228B1 (ko) |
| AR (1) | AR241785A1 (ko) |
| AT (1) | AT382621B (ko) |
| AU (1) | AU575541B2 (ko) |
| CA (1) | CA1269978A (ko) |
| CH (1) | CH656130A5 (ko) |
| CS (1) | CS247168B2 (ko) |
| DD (1) | DD212255A5 (ko) |
| DE (1) | DE3334937A1 (ko) |
| DK (1) | DK442383A (ko) |
| ES (1) | ES525983A0 (ko) |
| FI (1) | FI78094C (ko) |
| FR (1) | FR2533568B1 (ko) |
| GB (1) | GB2128187B (ko) |
| GR (1) | GR78696B (ko) |
| HU (1) | HU191066B (ko) |
| IE (1) | IE55947B1 (ko) |
| IL (1) | IL69824A (ko) |
| IT (1) | IT1163944B (ko) |
| LU (1) | LU85021A1 (ko) |
| NL (1) | NL8303310A (ko) |
| NO (1) | NO163284C (ko) |
| NZ (1) | NZ205626A (ko) |
| OA (1) | OA07548A (ko) |
| PT (1) | PT77404B (ko) |
| SE (1) | SE461734B (ko) |
| SU (1) | SU1493108A3 (ko) |
| YU (1) | YU43196B (ko) |
| ZW (1) | ZW20783A1 (ko) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4683296A (en) * | 1983-03-07 | 1987-07-28 | Bristol-Myers Company | Carbapenem intermediates |
| CA1273011A (en) * | 1984-07-02 | 1990-08-21 | Susan M. Schmitt | Carbapenems having an externally alkylated mono- or bicyclic 2-quaternary heteroarylalkylthio substituent |
| CA1273012A (en) * | 1984-07-02 | 1990-08-21 | Burton G. Christensen | 1-methylcarbapenems having an externally alkylated mono- of bicyclic 2-quarternary heteroarylalkylthio substituent |
| US4725594A (en) * | 1984-12-13 | 1988-02-16 | Merck & Co., Inc. | Carbapenems having an internally or externally alkylated mono- or bicyclic 2-quaternary heteroarylalxyl heteromethyl substituent |
| US4729993A (en) * | 1984-12-13 | 1988-03-08 | Merck & Co., Inc. | Carbapenems and 1-methylcarbapenems having an externally alkylated mono- or bicyclic 2-quaternary heteroarylalkyl substituent |
| US4680292A (en) * | 1984-12-13 | 1987-07-14 | Merck & Co., Inc. | Carbapenems and 1-methylcarbapenems having a 2-heteroaryliumaliphatic substituent |
| US4665169A (en) * | 1985-09-11 | 1987-05-12 | Bristol-Myers Company | Carbapenem antibiotics |
| US4880922A (en) * | 1985-11-22 | 1989-11-14 | Bristol-Myers Company | Carbapenems with quaternized heterothioalkylthio substitution at position 2 |
| NZ219892A (en) * | 1986-04-15 | 1991-02-26 | Merck & Co Inc | N-amino quaternised heteroarylium carbapenem derivatives and pharmaceutical compositions thereof |
| DK168047B1 (da) * | 1987-12-07 | 1994-01-24 | Lederle Japan Ltd | (1r,5s,6s)-2-substitueret thio-6-oe(r)-1-hydroxyethylaa-1-methyl-carbapenem-3-carboxylsyrederivater, fremgangsmaade til remstilling deraf, midler og praeparater indeholdende den krystallinske forbindelse samt dens anvendelse. |
| CA2241321A1 (en) | 1996-01-12 | 1997-07-17 | Tetsuo Miwa | Carbapenem compounds, their production and use |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0017992A1 (en) * | 1979-04-19 | 1980-10-29 | Merck & Co. Inc. | 2-Substituted-6-substituted-1-carbadethiapen-2-em-3-carboxylic acids, processes for preparing them, antibiotic pharmaceutical compositions containing same and process for preparing intermediates |
| IE52147B1 (en) * | 1980-03-27 | 1987-07-08 | Merck & Co Inc | 4-(3-carboxy-2-oxopropyl)-azetidin-2-ones and process for their preparation |
| EP0038869A1 (en) * | 1980-04-30 | 1981-11-04 | Merck & Co. Inc. | Process for the preparation of 1-carbapenems, and intermediates for their preparation |
| PT73791B (en) * | 1980-10-17 | 1983-10-14 | Merck & Co Inc | Process for preparing 2-carbamimidoyl-6-substituted-1- -carbadethiapen-2-em-3-carboxylic acids |
| GB2089340B (en) * | 1980-10-25 | 1984-09-19 | Beecham Group Ltd | -lactam antibiotics their preparation and their use |
| US4552873A (en) * | 1981-08-19 | 1985-11-12 | Sankyo Company Limited | Carbapenem compounds, and compositions containing them |
| EP0074599A1 (en) * | 1981-09-09 | 1983-03-23 | Takeda Chemical Industries, Ltd. | 5,6-cis-Carbapenem derivatives, their production and use |
-
1983
- 1983-09-16 CA CA000436924A patent/CA1269978A/en not_active Expired - Lifetime
- 1983-09-16 NZ NZ205626A patent/NZ205626A/en unknown
- 1983-09-21 AU AU19342/83A patent/AU575541B2/en not_active Ceased
- 1983-09-22 FR FR838315069A patent/FR2533568B1/fr not_active Expired - Fee Related
- 1983-09-22 GR GR72509A patent/GR78696B/el unknown
- 1983-09-22 YU YU1906/83A patent/YU43196B/xx unknown
- 1983-09-23 FI FI833417A patent/FI78094C/fi not_active IP Right Cessation
- 1983-09-27 NO NO833479A patent/NO163284C/no unknown
- 1983-09-27 DE DE19833334937 patent/DE3334937A1/de active Granted
- 1983-09-27 PT PT77404A patent/PT77404B/pt not_active IP Right Cessation
- 1983-09-27 IT IT23022/83A patent/IT1163944B/it active
- 1983-09-27 DK DK442383A patent/DK442383A/da not_active Application Discontinuation
- 1983-09-27 SE SE8305217A patent/SE461734B/sv not_active IP Right Cessation
- 1983-09-27 NL NL8303310A patent/NL8303310A/nl not_active Application Discontinuation
- 1983-09-27 IL IL69824A patent/IL69824A/xx unknown
- 1983-09-27 HU HU833351A patent/HU191066B/hu not_active IP Right Cessation
- 1983-09-27 GB GB08325744A patent/GB2128187B/en not_active Expired
- 1983-09-27 AR AR83294329A patent/AR241785A1/es active
- 1983-09-27 OA OA58118A patent/OA07548A/xx unknown
- 1983-09-27 CS CS837049A patent/CS247168B2/cs unknown
- 1983-09-27 ES ES525983A patent/ES525983A0/es active Granted
- 1983-09-27 SU SU833648007A patent/SU1493108A3/ru active
- 1983-09-27 IE IE2266/83A patent/IE55947B1/en not_active IP Right Cessation
- 1983-09-28 ZW ZW207/83A patent/ZW20783A1/xx unknown
- 1983-09-28 LU LU85021A patent/LU85021A1/fr unknown
- 1983-09-28 DD DD83255191A patent/DD212255A5/de not_active IP Right Cessation
- 1983-09-28 KR KR1019830004574A patent/KR890002228B1/ko not_active IP Right Cessation
- 1983-09-28 CH CH5263/83A patent/CH656130A5/de not_active IP Right Cessation
- 1983-09-28 AT AT0344983A patent/AT382621B/de not_active IP Right Cessation
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