ZA200300676B - Azabicyclic compounds, preparation thereof and use as medicines, in particular as antibacterial agents. - Google Patents

Azabicyclic compounds, preparation thereof and use as medicines, in particular as antibacterial agents. Download PDF

Info

Publication number: ZA200300676B
Authority: ZA; South Africa
Prior art keywords: group; radical; protected; hydrogen atom; carbon atoms
Prior art date: 2000-08-01

Application number

ZA200300676A

Other languages

English (en)

Inventor

Maxime Lampilas

Jozsef Aszodi

David Alun Rowlands

Claude Fromentin

Original Assignee

Aventis Pharma Sa

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.)

2000-08-01

Filing date

2003-01-24

Publication date

2004-05-10

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8853181&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ZA200300676(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2003-01-24 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

2004-05-10 Publication of ZA200300676B publication Critical patent/ZA200300676B/en

Links

150000001875 compounds Chemical class 0.000 title claims description 55
239000003814 drug Substances 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 11
239000003242 anti bacterial agent Substances 0.000 title description 2
229940079593 drug Drugs 0.000 title 1
-1 alkyl radical Chemical class 0.000 claims description 73
239000002585 base Substances 0.000 claims description 35
125000004432 carbon atom Chemical group C* 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 32
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
239000002253 acid Substances 0.000 claims description 26
150000003254 radicals Chemical class 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 22
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 19
239000011734 sodium Substances 0.000 claims description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
229910052708 sodium Inorganic materials 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 15
238000000034 method Methods 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
125000003831 tetrazolyl group Chemical group 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 9
238000005810 carbonylation reaction Methods 0.000 claims description 9
238000010511 deprotection reaction Methods 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
239000000969 carrier Substances 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
230000004224 protection Effects 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
150000001408 amides Chemical class 0.000 claims description 7
230000006315 carbonylation Effects 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
150000003536 tetrazoles Chemical class 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
150000005840 aryl radicals Chemical class 0.000 claims description 4
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
238000007127 saponification reaction Methods 0.000 claims description 4
OVKXDANNQWXYKF-UHFFFAOYSA-N 2-methyloctanamide Chemical class CCCCCCC(C)C(N)=O OVKXDANNQWXYKF-UHFFFAOYSA-N 0.000 claims description 3
MXPCVNXHFDGZRB-PHDIDXHHSA-N C1N2[C@@H](C(=O)NCC(N)=O)CC[C@@]1([H])N(OS(O)(=O)=O)C2=O Chemical class C1N2[C@@H](C(=O)NCC(N)=O)CC[C@@]1([H])N(OS(O)(=O)=O)C2=O MXPCVNXHFDGZRB-PHDIDXHHSA-N 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 3
238000005917 acylation reaction Methods 0.000 claims description 3
238000005804 alkylation reaction Methods 0.000 claims description 3
238000007112 amidation reaction Methods 0.000 claims description 3
230000018044 dehydration Effects 0.000 claims description 3
238000006297 dehydration reaction Methods 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
150000004678 hydrides Chemical class 0.000 claims description 3
238000005342 ion exchange Methods 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
150000002825 nitriles Chemical class 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
238000000926 separation method Methods 0.000 claims description 3
125000001174 sulfone group Chemical group 0.000 claims description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
230000009435 amidation Effects 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
PWEBUXCTKOWPCW-UHFFFAOYSA-L squarate Chemical group [O-]C1=C([O-])C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-L 0.000 claims description 2
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 4
229910006069 SO3H Inorganic materials 0.000 claims 2
125000003710 aryl alkyl group Chemical group 0.000 claims 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
239000012429 reaction media Substances 0.000 description 31
239000000047 product Substances 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
239000002904 solvent Substances 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
230000009471 action Effects 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000012298 atmosphere Substances 0.000 description 12
239000012043 crude product Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 7
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
235000002906 tartaric acid Nutrition 0.000 description 6
239000011975 tartaric acid Substances 0.000 description 6
238000013019 agitation Methods 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
239000013078 crystal Substances 0.000 description 5
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 5
238000001035 drying Methods 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
238000007327 hydrogenolysis reaction Methods 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000000126 substance Substances 0.000 description 5
229960000549 4-dimethylaminophenol Drugs 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000001261 hydroxy acids Chemical class 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000007017 scission Effects 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
NDCUAPJVLWFHHB-RFZPGFLSSA-N [(2r,5r)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical class C1N2[C@@H](C(N)=O)CC[C@@]1([H])N(OS(O)(=O)=O)C2=O NDCUAPJVLWFHHB-RFZPGFLSSA-N 0.000 description 2
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000010265 fast atom bombardment Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
150000002596 lactones Chemical class 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
AFINAILKDBCXMX-PBHICJAKSA-N (2s,3r)-2-amino-3-hydroxy-n-(4-octylphenyl)butanamide Chemical compound CCCCCCCCC1=CC=C(NC(=O)[C@@H](N)[C@@H](C)O)C=C1 AFINAILKDBCXMX-PBHICJAKSA-N 0.000 description 1
JWZMLPVLGNVRKQ-UHFFFAOYSA-N (4-nitrophenyl)methyl hydrogen carbonate Chemical class OC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 JWZMLPVLGNVRKQ-UHFFFAOYSA-N 0.000 description 1
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
GPAAEZIXSQCCES-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxymethoxymethoxy)ethane Chemical class COCCOCOCOCCOC GPAAEZIXSQCCES-UHFFFAOYSA-N 0.000 description 1
ZLRFPQPVXRIBCQ-UHFFFAOYSA-N 2-$l^{1}-oxidanyl-2-methylpropane Chemical compound CC(C)(C)[O] ZLRFPQPVXRIBCQ-UHFFFAOYSA-N 0.000 description 1
RGJBDTNYISGBNL-DTWKUNHWSA-N 2-[(3s,4s)-3-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]acetic acid Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](CC(O)=O)[C@H](O)C1 RGJBDTNYISGBNL-DTWKUNHWSA-N 0.000 description 1
SIRALSXDSRQQMW-WDSKDSINSA-N 2-[(4s,5r)-7-oxo-6-oxa-1-azabicyclo[3.2.1]octan-4-yl]acetic acid Chemical compound C1N2CC[C@@H](CC(O)=O)[C@@]1([H])OC2=O SIRALSXDSRQQMW-WDSKDSINSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
MKSTXMDSWOHKOR-UHFFFAOYSA-N 3-aminopyrrolidine-1-carboxylic acid Chemical compound NC1CCN(C(O)=O)C1 MKSTXMDSWOHKOR-UHFFFAOYSA-N 0.000 description 1
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VRVPRKZTEHHUTH-UHFFFAOYSA-N tert-butyl 3-benzamidopyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1NC(=O)C1=CC=CC=C1 VRVPRKZTEHHUTH-UHFFFAOYSA-N 0.000 description 1
MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
- 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
- C07D487/08—Bridged systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (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)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Urology & Nephrology (AREA)
Dermatology (AREA)
Pulmonology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

ZA200300676A 2000-08-01 2003-01-24 Azabicyclic compounds, preparation thereof and use as medicines, in particular as antibacterial agents. ZA200300676B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR0010121A FR2812635B1 (fr)	2000-08-01	2000-08-01	Nouveaux composes heterocycliques, preparation et utilisation comme medicaments notamment comme anti- bacteriens

Publications (1)

Publication Number	Publication Date
ZA200300676B true ZA200300676B (en)	2004-05-10

Family

ID=8853181

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200300676A ZA200300676B (en)	2000-08-01	2003-01-24	Azabicyclic compounds, preparation thereof and use as medicines, in particular as antibacterial agents.

Country Status (42)

Country	Link
US (5)	US7112592B2 (sr)
EP (1)	EP1307457B1 (sr)
JP (2)	JP4515704B2 (sr)
KR (1)	KR100632906B1 (sr)
CN (1)	CN1289500C (sr)
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- 2001-07-24 HU HU0302943A patent/HU226889B1/hu unknown
- 2001-07-24 CN CNB018167004A patent/CN1289500C/zh not_active Expired - Lifetime
- 2001-07-24 PT PT01958173T patent/PT1307457E/pt unknown
- 2001-07-24 DE DE60102702T patent/DE60102702T2/de not_active Expired - Lifetime
- 2001-07-24 WO PCT/FR2001/002418 patent/WO2002010172A1/fr not_active Application Discontinuation
- 2001-07-25 TW TW090118209A patent/TWI292401B/zh not_active IP Right Cessation
- 2001-07-26 AR ARP010103571A patent/AR031716A1/es active IP Right Grant
2003
- 2003-01-21 HR HR20030034A patent/HRP20030034B1/xx not_active IP Right Cessation
- 2003-01-23 BG BG107497A patent/BG66094B1/bg unknown
- 2003-01-24 ZA ZA200300676A patent/ZA200300676B/en unknown
- 2003-01-28 MA MA27016A patent/MA26938A1/fr unknown
- 2003-01-29 CR CR6895A patent/CR6895A/es unknown
- 2003-01-29 IL IL154187A patent/IL154187A/en unknown
- 2003-01-30 EC EC2003004460A patent/ECSP034460A/es unknown
- 2003-01-31 NO NO20030494A patent/NO324940B1/no not_active IP Right Cessation
2004
- 2004-05-11 HK HK04103300A patent/HK1060356A1/xx not_active IP Right Cessation
2005
- 2005-09-14 US US11/226,749 patent/US7638529B2/en not_active Expired - Fee Related
2006
- 2006-02-06 US US11/348,047 patent/US7732610B2/en not_active Expired - Lifetime
2010
- 2010-03-16 JP JP2010059251A patent/JP2010138206A/ja active Pending
- 2010-04-16 US US12/799,038 patent/US20110021772A1/en not_active Abandoned
2011
- 2011-05-10 US US13/068,399 patent/US8178554B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
PT1307457E (pt)	2004-08-31
TWI292401B (en)	2008-01-11
DE60102702T2 (de)	2005-04-07
FR2812635B1 (fr)	2002-10-11
NO20030494L (no)	2003-03-28
IL154187A0 (en)	2003-07-31
US20110021772A1 (en)	2011-01-27
SI1307457T1 (en)	2004-08-31
CZ294956B6 (cs)	2005-04-13
HUP0302943A3 (en)	2007-08-28
US8178554B2 (en)	2012-05-15
BG107497A (bg)	2003-09-30
EE200300046A (et)	2004-10-15
DK1307457T3 (da)	2004-08-09
PL216028B1 (pl)	2014-02-28
ATE263768T1 (de)	2004-04-15
KR100632906B1 (ko)	2006-10-13
CA2417475A1 (fr)	2002-02-07
EP1307457A1 (fr)	2003-05-07
YU6303A (sh)	2006-03-03
MXPA03000881A (es)	2003-06-06
RS50214B (sr)	2009-07-15
IL154187A (en)	2009-02-11
JP4515704B2 (ja)	2010-08-04
JP2010138206A (ja)	2010-06-24
ME00060B (me)	2010-06-10
JP2004505088A (ja)	2004-02-19
AU2001279905B2 (en)	2005-12-08
AP2003002726A0 (en)	2003-06-30
NZ523707A (en)	2005-02-25
HK1060356A1 (en)	2004-08-06
US20030199541A1 (en)	2003-10-23
TR200400859T4 (tr)	2004-06-21
BR0112986A (pt)	2003-07-08
EP1307457B1 (fr)	2004-04-07
MA26938A1 (fr)	2004-12-20
CZ2003223A3 (cs)	2003-08-13
CR6895A (es)	2007-07-12
WO2002010172A1 (fr)	2002-02-07
HRP20030034B1 (en)	2011-03-31
AU7990501A (en)	2002-02-13
OA12347A (fr)	2006-05-15
BRPI0112986B8 (pt)	2021-05-25
NO324940B1 (no)	2008-01-07
US20060046995A1 (en)	2006-03-02
FR2812635A1 (fr)	2002-02-08
HUP0302943A2 (hu)	2003-12-29
UA73791C2 (uk)	2005-09-15
NO20030494D0 (no)	2003-01-31
HU226889B1 (en)	2010-01-28
ECSP034460A (es)	2003-03-10
US7638529B2 (en)	2009-12-29
EA004920B1 (ru)	2004-10-28
PL401469A1 (pl)	2013-02-04
EA200300211A1 (ru)	2003-06-26
EE05183B1 (et)	2009-06-15
CA2417475C (en)	2010-04-20
CN1289500C (zh)	2006-12-13
HRP20030034A2 (en)	2004-02-29
US20110213147A1 (en)	2011-09-01
KR20030019642A (ko)	2003-03-06
PL365162A1 (en)	2004-12-27
SK287597B6 (sk)	2011-03-04
ES2220793T3 (es)	2004-12-16
US7732610B2 (en)	2010-06-08
MEP17108A (en)	2010-06-10
US20060189652A1 (en)	2006-08-24
DE60102702D1 (de)	2004-05-13
AR031716A1 (es)	2003-10-01
PL234468B1 (pl)	2020-02-28
SK1052003A3 (en)	2003-11-04
BG66094B1 (bg)	2011-04-29
CN1468242A (zh)	2004-01-14
US7112592B2 (en)	2006-09-26
DZ3397A1 (fr)	2002-02-07
AP1614A (en)	2006-05-21
BR0112986B1 (pt)	2014-04-01

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US8148540B2 (en)	2012-04-03	Heterocyclic compounds, their preparation and their use as medicaments, in particular as anti-bacterial agents
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