ZA200303796B - 1-methylcarbapenem derivatives. - Google Patents

1-methylcarbapenem derivatives. Download PDF

Info

Publication number: ZA200303796B
Authority: ZA; South Africa
Prior art keywords: group; hydroxyethyl; carboxylic acid; methylcarbapen; hydrogen atom
Prior art date: 2000-11-16

Application number

ZA200303796A

Other languages

English (en)

Inventor

Yoshiyuki Kobayashi

Osamu Kanno

Tsuyoshi Shinozuka

Original Assignee

Sankyo Co

Priority date (The priority date 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 date listed.)

2000-11-16

Filing date

2003-05-15

Publication date

2004-08-16

2003-05-15 Application filed by Sankyo Co filed Critical Sankyo Co

2004-08-16 Publication of ZA200303796B publication Critical patent/ZA200303796B/en

Links

YKMONJZIUAOVEM-GDVGLLTNSA-N (5S)-4-methyl-1-azabicyclo[3.2.0]hept-2-en-7-one Chemical class CC1C=CN2[C@H]1CC2=O YKMONJZIUAOVEM-GDVGLLTNSA-N 0.000 title description 7
-1 1-methylcarbapenem compound Chemical class 0.000 claims description 158
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 70
125000000217 alkyl group Chemical group 0.000 claims description 62
150000001875 compounds Chemical class 0.000 claims description 57
150000003839 salts Chemical class 0.000 claims description 52
150000002148 esters Chemical class 0.000 claims description 48
125000001424 substituent group Chemical group 0.000 claims description 46
229910052799 carbon Inorganic materials 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
125000004434 sulfur atom Chemical group 0.000 claims description 20
229910052717 sulfur Inorganic materials 0.000 claims description 18
125000004430 oxygen atom Chemical group O* 0.000 claims description 17
229910052792 caesium Inorganic materials 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 10
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
230000002265 prevention Effects 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
125000002393 azetidinyl group Chemical group 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
125000003386 piperidinyl group Chemical group 0.000 claims description 7
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
125000005505 thiomorpholino group Chemical group 0.000 claims description 6
208000035143 Bacterial infection Diseases 0.000 claims description 5
208000022362 bacterial infectious disease Diseases 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229910052684 Cerium Inorganic materials 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 2
239000000203 mixture Substances 0.000 claims 11
125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 10
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
DUNKKIRUWZSMPT-RXMQYKEDSA-N (5r)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CS[C@@H]2CC(=O)N12 DUNKKIRUWZSMPT-RXMQYKEDSA-N 0.000 claims 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 4
125000005129 aryl carbonyl group Chemical group 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
125000004423 acyloxy group Chemical group 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
241000282414 Homo sapiens Species 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
125000000266 alpha-aminoacyl group Chemical group 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
229930192474 thiophene Natural products 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical class CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 1
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical class C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical class NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
101000941450 Lasioglossum laticeps Lasioglossin-1 Proteins 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
125000005042 acyloxymethyl group Chemical group 0.000 description 1
125000001980 alanyl group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
125000005206 alkoxycarbonyloxymethyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
159000000013 aluminium salts Chemical class 0.000 description 1
229910000329 aluminium sulfate Inorganic materials 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
125000000539 amino acid group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
125000000637 arginyl group Chemical class N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
229940009098 aspartate Drugs 0.000 description 1
125000004069 aziridinyl group Chemical group 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical class C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000010170 biological method Methods 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 description 1
VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
150000001868 cobalt Chemical class 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
150000005332 diethylamines Chemical class 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
150000002301 glucosamine derivatives Chemical class 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000002505 iron Chemical class 0.000 description 1
125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
125000001998 leucyl group Chemical group 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000002815 nickel Chemical class 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003566 oxetanyl group Chemical group 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
125000000405 phenylalanyl group Chemical group 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000012453 solvate Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

ZA200303796A 2000-11-16 2003-05-15 1-methylcarbapenem derivatives. ZA200303796B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2000350063		2000-11-16

Publications (1)

Publication Number	Publication Date
ZA200303796B true ZA200303796B (en)	2004-08-16

Family

ID=18823361

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200303796A ZA200303796B (en)	2000-11-16	2003-05-15	1-methylcarbapenem derivatives.

Country Status (24)

Country	Link
US (1)	US7001897B2 (da)
EP (1)	EP1340757B1 (da)
KR (1)	KR100832287B1 (da)
CN (1)	CN1289498C (da)
AT (1)	ATE342266T1 (da)
AU (2)	AU1521202A (da)
BR (1)	BR0115454A (da)
CA (1)	CA2429346A1 (da)
CZ (1)	CZ300137B6 (da)
DE (1)	DE60123827T2 (da)
DK (1)	DK1340757T3 (da)
ES (1)	ES2273902T3 (da)
HU (1)	HUP0303204A3 (da)
IL (1)	IL155931A0 (da)
MX (1)	MXPA03004372A (da)
NO (1)	NO20032198L (da)
NZ (1)	NZ525934A (da)
PL (1)	PL362132A1 (da)
PT (1)	PT1340757E (da)
RU (1)	RU2247725C2 (da)
SK (1)	SK5982003A3 (da)
TW (1)	TWI242013B (da)
WO (1)	WO2002040483A1 (da)
ZA (1)	ZA200303796B (da)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR0211291A (pt) *	2001-07-18	2004-08-03	Mitsui Chemicals Inc	Derivados de diamina, processo para produção dos derivados de diamina e fungicidas contendo os derivados de diamina como ingrediente ativo
KR100451670B1 (ko) *	2001-09-14	2004-10-08	한국화학연구원	내성균에 대해 항생작용을 갖는 카바페넴 유도체 및 이의제조방법
KR100599876B1 (ko) *	2004-08-31	2006-07-13	한국화학연구원	2-아릴메틸아제티딘 카바페넴 유도체 및 그의 제조방법
EP1637529A1 (en) *	2004-09-20	2006-03-22	4Sc Ag	Novel piperidin-4-yl-thiazole-carboxamide analogues as inhibitors of T-cell proliferation and uses thereof
US7601745B2 (en) *	2004-09-27	2009-10-13	4Sc Ag	Heterocyclic NF-kB inhibitors
EP2009005A4 (en)	2006-04-19	2010-06-02	Astellas Pharma Inc	AZOLECARBOXAMIDE DERIVATIVE
CN101328179B (zh) *	2007-06-15	2011-01-12	山东轩竹医药科技有限公司	含有氧代氮杂环的巯基吡咯烷培南衍生物
SI2206707T1 (sl)	2007-10-24	2014-11-28	Astellas Pharma Inc.	Azolkarboksamidna spojina ali njena sol
ES2533826T3 (es)	2008-01-18	2015-04-15	Merck Sharp & Dohme Corp.	Inhibidores de beta-lactamasa
US9409895B2 (en)	2012-12-19	2016-08-09	Novartis Ag	Autotaxin inhibitors
WO2014097151A2 (en)	2012-12-19	2014-06-26	Novartis Ag	Autotaxin inhibitors
AU2022300325A1 (en) *	2021-06-23	2023-11-02	F. Hoffmann-La Roche Ag	Process for the preparation of nlrp3 inhibitors

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3784147T2 (de) *	1986-11-24	1993-06-03	Fujisawa Pharmaceutical Co	3-pyrrolidinylthio-1-azabicyclo(3.2.0)hept-2-en-2-carbonsaeure-derivate.
GB9210096D0 (en) *	1992-05-11	1992-06-24	Fujisawa Pharmaceutical Co	1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid derivatives and their preparation
AU682510B2 (en) *	1993-07-01	1997-10-09	Pfizer Japan Inc.	2-(1-(1,3-thiazolin-2-yl)azetidin-3-yl)thio-carbapenem derivatives
DE4423612A1 (de)	1994-07-06	1996-01-11	Basf Ag	2-[(Dihydro)pyrazolyl-3'-oxymethylen]-anilide, Verfahren zu ihrer Herstelung und ihre Verwendung
TW445265B (en) *	1996-11-25	2001-07-11	Meiji Seika Kaisha	Carbapenem derivatives and antimicrobial agents
TW200403244A (en) *	2002-05-14	2004-03-01	Sankyo Co	1β-Methylcarbapenem derivatives for oral use
JP2004043438A (ja) *	2002-05-15	2004-02-12	Sankyo Co Ltd	１−メチルカルバペネム誘導体を含有する医薬

2001
- 2001-11-14 MX MXPA03004372A patent/MXPA03004372A/es active IP Right Grant
- 2001-11-14 SK SK598-2003A patent/SK5982003A3/sk unknown
- 2001-11-14 ES ES01983800T patent/ES2273902T3/es not_active Expired - Lifetime
- 2001-11-14 IL IL15593101A patent/IL155931A0/xx unknown
- 2001-11-14 AU AU1521202A patent/AU1521202A/xx active Pending
- 2001-11-14 CN CNB018220703A patent/CN1289498C/zh not_active Expired - Fee Related
- 2001-11-14 NZ NZ525934A patent/NZ525934A/en unknown
- 2001-11-14 AT AT01983800T patent/ATE342266T1/de not_active IP Right Cessation
- 2001-11-14 PL PL01362132A patent/PL362132A1/xx not_active Application Discontinuation
- 2001-11-14 EP EP01983800A patent/EP1340757B1/en not_active Expired - Lifetime
- 2001-11-14 CZ CZ20031325A patent/CZ300137B6/cs not_active IP Right Cessation
- 2001-11-14 KR KR1020037006664A patent/KR100832287B1/ko not_active IP Right Cessation
- 2001-11-14 PT PT01983800T patent/PT1340757E/pt unknown
- 2001-11-14 DE DE60123827T patent/DE60123827T2/de not_active Expired - Fee Related
- 2001-11-14 AU AU2002215212A patent/AU2002215212B2/en not_active Ceased
- 2001-11-14 CA CA002429346A patent/CA2429346A1/en not_active Abandoned
- 2001-11-14 BR BR0115454-0A patent/BR0115454A/pt not_active IP Right Cessation
- 2001-11-14 HU HU0303204A patent/HUP0303204A3/hu unknown
- 2001-11-14 WO PCT/JP2001/009960 patent/WO2002040483A1/ja active IP Right Grant
- 2001-11-14 RU RU2003114408/04A patent/RU2247725C2/ru not_active IP Right Cessation
- 2001-11-14 DK DK01983800T patent/DK1340757T3/da active
- 2001-11-15 TW TW090128317A patent/TWI242013B/zh not_active IP Right Cessation
2003
- 2003-05-15 NO NO20032198A patent/NO20032198L/no not_active Application Discontinuation
- 2003-05-15 ZA ZA200303796A patent/ZA200303796B/en unknown
- 2003-05-15 US US10/439,198 patent/US7001897B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP1340757A4 (en)	2005-01-26
CZ20031325A3 (cs)	2003-10-15
NO20032198D0 (no)	2003-05-15
NO20032198L (no)	2003-07-16
TWI242013B (en)	2005-10-21
NZ525934A (en)	2004-09-24
US7001897B2 (en)	2006-02-21
DE60123827T2 (de)	2007-05-31
CN1289498C (zh)	2006-12-13
CZ300137B6 (cs)	2009-02-18
WO2002040483A1 (fr)	2002-05-23
US20040014962A1 (en)	2004-01-22
RU2247725C2 (ru)	2005-03-10
ATE342266T1 (de)	2006-11-15
HUP0303204A3 (en)	2010-04-28
CA2429346A1 (en)	2002-05-23
ES2273902T3 (es)	2007-05-16
KR20030048151A (ko)	2003-06-18
KR100832287B1 (ko)	2008-05-26
PT1340757E (pt)	2006-12-29
EP1340757A1 (en)	2003-09-03
DK1340757T3 (da)	2007-02-12
HUP0303204A2 (hu)	2003-12-29
IL155931A0 (en)	2003-12-23
DE60123827D1 (en)	2006-11-23
BR0115454A (pt)	2003-09-23
MXPA03004372A (es)	2003-08-19
CN1486317A (zh)	2004-03-31
SK5982003A3 (en)	2004-05-04
AU1521202A (en)	2002-05-27
EP1340757B1 (en)	2006-10-11
AU2002215212B2 (en)	2004-10-14
PL362132A1 (en)	2004-10-18

Publication	Publication Date	Title
ZA200303796B (en)	2004-08-16	1-methylcarbapenem derivatives.
JP5542336B2 (ja)	2014-07-09	臨床的に潜伏性の微生物を死滅させるピロロキノリン化合物の使用
NZ591449A (en)	2012-12-21	Picolinamide derivatives as kinase inhibitors
JP2006513265A5 (da)	2006-08-10
NO20082338L (no)	2008-06-25	Pyrimidinderivater for behandling av avvikende cellevekst
NZ627385A (en)	2016-02-26	Piperidinone derivatives as mdm2 inhibitors for the treatment of cancer
HRP20120968T1 (hr)	2013-01-31	Spojevi
ATE512140T1 (de)	2011-06-15	1,2,3-triazolderivate zur verwendung als inhibitoren von stearoyl-coa-desaturase
CA2632771A1 (en)	2007-07-26	Substituted imidazoles and their use as pesticides
EP3139918B1 (en)	2019-12-25	Beta-tetrazolyl-propionic acids as metallo-beta-lactamase inhibitors
DE602005022764D1 (de)	2010-09-16	Piperidin- und azetidinderivate als glyt1-inhibitoren
MX2009009849A (es)	2009-09-24	Derivados de piridazinona sustituida con piperazina utiles como inhibidores de glucano sintasa.
RU2012142832A (ru)	2014-04-20	Мостиковые липогликопептиды, усиливающие активность бета-лактамных антибактериальных агентов
MX2009006636A (es)	2009-06-30	Nuevos intermediarios y procesos utiles en la rpeparacion de {2-[1-(3,5-bis-trifluorometil-bencil)-5-piridin-4-il-1h-[1,2,3]tr iazol-4-il]-piridin-3-il}-(2-clorofenil)-metanona.
WO2005123069A3 (en)	2006-08-10	Gram-positive carbapenem antibacterials and processes for their preparation
RU2011105059A (ru)	2012-08-20	Применение производных пиримидиламинобензамида для лечения фиброза
KR100386993B1 (ko)	2003-12-18	1-메틸카르바페넴유도체
US6221859B1 (en)	2001-04-24	Carbapenem antibacterial compositions and methods of the treatment
RU2222540C2 (ru)	2004-01-27	Производные карбапенема, их применение и промежуточные соединения для их получения
RU2011100106A (ru)	2012-10-27	Замещенные бензимидазолы для лечения нейрофиброматоза
RU2000130224A (ru)	2003-01-27	Производные карбапенема, их применение и промежуточные соединения для их получения
PE20071423A1 (es)	2006-12-17	Sales de mono-lisina de compuestos azol
RU2003114408A (ru)	2004-12-10	Производные 1-метилкарбапенема
CZ363598A3 (cs)	1999-04-14	Anti-"heliobacter pylori" prostředky obsahující 1-methylkarbapenemové deriváty jako aktivní sloučeniny
JPS61155387A (ja)	1986-07-15	内部又は外部アルキル化された単環又は２環式４級ヘテロアリール・アルキル・ヘテロメチル置換基を２位に有するカルパペネム類