OA12347A - Composés azabicycliques, leur préparation et leur utilisation comme médicaments, notamment comme anti-bactériens. - Google Patents

Composés azabicycliques, leur préparation et leur utilisation comme médicaments, notamment comme anti-bactériens. Download PDF

Info

Publication number: OA12347A
Authority: OA; OAPI
Prior art keywords: group; dichloromethane; added; reduced pressure; trans
Prior art date: 2000-08-01

Application number

OA1200300019A

Other languages

English (en)

French (fr)

Inventor

Maxime Lampilas

Jozsef Aszodi

David Alan 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

2001-07-24

Publication date

2006-05-15

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=OA12347(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2001-07-24 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

2006-05-15 Publication of OA12347A publication Critical patent/OA12347A/fr

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 160
238000002360 preparation method Methods 0.000 title claims abstract description 18
239000003814 drug Substances 0.000 title claims abstract description 13
230000000844 anti-bacterial effect Effects 0.000 title description 3
229940088710 antibiotic agent Drugs 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 41
239000002253 acid Substances 0.000 claims abstract description 36
238000000034 method Methods 0.000 claims abstract description 34
230000008569 process Effects 0.000 claims abstract description 9
239000000203 mixture Substances 0.000 claims description 176
-1 alkyl radical Chemical class 0.000 claims description 117
239000011734 sodium Substances 0.000 claims description 54
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 52
239000002585 base Substances 0.000 claims description 35
125000004432 carbon atom Chemical group C* 0.000 claims description 32
HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 claims description 31
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 29
150000003254 radicals Chemical class 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 19
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 18
229910052708 sodium Inorganic materials 0.000 claims description 17
150000001412 amines Chemical class 0.000 claims description 16
150000001408 amides Chemical class 0.000 claims description 11
150000003536 tetrazoles Chemical class 0.000 claims description 11
150000007513 acids Chemical class 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
238000010511 deprotection reaction Methods 0.000 claims description 8
230000004224 protection Effects 0.000 claims description 8
238000005810 carbonylation reaction Methods 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
OVKXDANNQWXYKF-UHFFFAOYSA-N 2-methyloctanamide Chemical class CCCCCCC(C)C(N)=O OVKXDANNQWXYKF-UHFFFAOYSA-N 0.000 claims description 5
GRZOIGCMOCWPHU-VXGBXAGGSA-N O=C([C@@H]1N2C[C@@](CC1)(N(C2=O)OS(O)(=O)=O)[H])OCC1=CC=CC=C1 Chemical compound O=C([C@@H]1N2C[C@@](CC1)(N(C2=O)OS(O)(=O)=O)[H])OCC1=CC=CC=C1 GRZOIGCMOCWPHU-VXGBXAGGSA-N 0.000 claims description 5
229910006069 SO3H Inorganic materials 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
230000006315 carbonylation Effects 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
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 claims description 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
238000007127 saponification reaction Methods 0.000 claims description 4
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-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 compound 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
ZDZLZLBMGLFZKY-VXGBXAGGSA-N O=C([C@@H]1N2C[C@@](CC1)(N(C2=O)OS(O)(=O)=O)[H])NCC1=CC=CC=C1 Chemical class O=C([C@@H]1N2C[C@@](CC1)(N(C2=O)OS(O)(=O)=O)[H])NCC1=CC=CC=C1 ZDZLZLBMGLFZKY-VXGBXAGGSA-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
150000005840 aryl radicals Chemical class 0.000 claims description 3
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
230000018044 dehydration Effects 0.000 claims description 3
238000006297 dehydration reaction Methods 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
150000002825 nitriles Chemical class 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
238000000926 separation method Methods 0.000 claims description 3
238000005670 sulfation reaction Methods 0.000 claims description 3
150000003457 sulfones Chemical class 0.000 claims description 3
238000005694 sulfonylation reaction Methods 0.000 claims description 3
150000003462 sulfoxides Chemical class 0.000 claims description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
OYKQFPLVJDOKLB-GHMZBOCLSA-N O=C([C@@H]1N2C[C@@](CC1)(N(C2=O)OS(O)(=O)=O)[H])NCC1=CC=NC=C1 Chemical compound O=C([C@@H]1N2C[C@@](CC1)(N(C2=O)OS(O)(=O)=O)[H])NCC1=CC=NC=C1 OYKQFPLVJDOKLB-GHMZBOCLSA-N 0.000 claims description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-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
125000003342 alkenyl group Chemical group 0.000 claims description 2
150000004703 alkoxides Chemical class 0.000 claims description 2
230000029936 alkylation Effects 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
229940079593 drug Drugs 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 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 compound [O-]C1=C([O-])C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-L 0.000 claims description 2
230000019635 sulfation Effects 0.000 claims description 2
230000006103 sulfonylation Effects 0.000 claims description 2
125000003831 tetrazolyl group Chemical group 0.000 claims 4
125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
125000003545 alkoxy group Chemical group 0.000 claims 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims 1
125000003107 substituted aryl group Chemical group 0.000 claims 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims 1
150000002391 heterocyclic compounds Chemical class 0.000 abstract description 2
239000003242 anti bacterial agent Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 635
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 367
230000002829 reductive effect Effects 0.000 description 175
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 152
239000002904 solvent Substances 0.000 description 129
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 123
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 123
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 106
239000000047 product Substances 0.000 description 102
239000000243 solution Substances 0.000 description 101
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 98
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 93
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 87
239000007864 aqueous solution Substances 0.000 description 77
239000000377 silicon dioxide Substances 0.000 description 76
238000003756 stirring Methods 0.000 description 68
238000004587 chromatography analysis Methods 0.000 description 67
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 66
239000012074 organic phase Substances 0.000 description 65
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 61
239000012043 crude product Substances 0.000 description 56
229910052943 magnesium sulfate Inorganic materials 0.000 description 53
235000019341 magnesium sulphate Nutrition 0.000 description 53
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 50
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
239000000126 substance Substances 0.000 description 49
239000012298 atmosphere Substances 0.000 description 48
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 42
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 39
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 39
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 39
239000011975 tartaric acid Substances 0.000 description 39
235000002906 tartaric acid Nutrition 0.000 description 39
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
229910052938 sodium sulfate Inorganic materials 0.000 description 36
235000011152 sodium sulphate Nutrition 0.000 description 36
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 34
239000003921 oil Substances 0.000 description 34
235000019198 oils Nutrition 0.000 description 34
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 32
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 31
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 31
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 25
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
229920006395 saturated elastomer Polymers 0.000 description 24
239000011780 sodium chloride Substances 0.000 description 23
239000003054 catalyst Substances 0.000 description 22
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 21
229910000041 hydrogen chloride Inorganic materials 0.000 description 21
238000001704 evaporation Methods 0.000 description 20
230000008020 evaporation Effects 0.000 description 20
159000000000 sodium salts Chemical class 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
239000012299 nitrogen atmosphere Substances 0.000 description 18
229960000549 4-dimethylaminophenol Drugs 0.000 description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
230000009471 action Effects 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
239000007858 starting material Substances 0.000 description 13
239000011261 inert gas Substances 0.000 description 12
239000012429 reaction media Substances 0.000 description 12
239000013078 crystal Substances 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
239000008363 phosphate buffer Substances 0.000 description 11
239000007787 solid Substances 0.000 description 11
239000000725 suspension Substances 0.000 description 11
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
101150041968 CDC13 gene Proteins 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
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 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
238000007792 addition 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
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
239000006260 foam Substances 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
229920001467 poly(styrenesulfonates) Polymers 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
239000011347 resin Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 5
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
239000000460 chlorine 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
239000003480 eluent Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000007327 hydrogenolysis reaction Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 5
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
239000008055 phosphate buffer solution Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
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 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
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229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
230000036210 malignancy Effects 0.000 description 1
CGJMROBVSBIBKP-UHFFFAOYSA-N malonamic acid Chemical compound NC(=O)CC(O)=O CGJMROBVSBIBKP-UHFFFAOYSA-N 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
DNWQULQKZBSTEE-VZXYPILPSA-N methyl (2r,4s)-4-benzamidopyrrolidine-2-carboxylate;hydrochloride Chemical compound Cl.C1N[C@@H](C(=O)OC)C[C@@H]1NC(=O)C1=CC=CC=C1 DNWQULQKZBSTEE-VZXYPILPSA-N 0.000 description 1
DYBDOVKHIAJFQP-UHFFFAOYSA-N methyl 4-anilino-3-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC=C1NC1=CC=CC=C1 DYBDOVKHIAJFQP-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
ONMQJOUYBLBFBI-UHFFFAOYSA-N n-benzylpiperidin-3-amine Chemical compound C=1C=CC=CC=1CNC1CCCNC1 ONMQJOUYBLBFBI-UHFFFAOYSA-N 0.000 description 1
GSMPSKWDIFSIAR-UHFFFAOYSA-N n-cyclohexyl-1-(4-nitrophenyl)methanimine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=NC1CCCCC1 GSMPSKWDIFSIAR-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
NOQGHLSHVNUSKX-UHFFFAOYSA-N n-phenylmethoxy-1,2,3,6-tetrahydropyridin-3-amine Chemical compound C=1C=CC=CC=1CONC1CNCC=C1 NOQGHLSHVNUSKX-UHFFFAOYSA-N 0.000 description 1
WXVBYGAUTHAAAW-UHFFFAOYSA-N n-phenylmethoxy-1,2,3,6-tetrahydropyridin-3-amine;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1CONC1CNCC=C1 WXVBYGAUTHAAAW-UHFFFAOYSA-N 0.000 description 1
MNPZBYLCTOOFPY-UHFFFAOYSA-N n-piperidin-4-ylbenzamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(=O)NC1CCNCC1 MNPZBYLCTOOFPY-UHFFFAOYSA-N 0.000 description 1
QMAHBNNINZWBGF-UHFFFAOYSA-N n-prop-2-enoxy-1,2,3,6-tetrahydropyridin-3-amine Chemical compound C=CCONC1CNCC=C1 QMAHBNNINZWBGF-UHFFFAOYSA-N 0.000 description 1
BMOLKBZTZCSBQQ-UHFFFAOYSA-N n-prop-2-enoxy-1,2,3,6-tetrahydropyridin-3-amine;dihydrochloride Chemical compound Cl.Cl.C=CCONC1CNCC=C1 BMOLKBZTZCSBQQ-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XDALBRBPLAEAPK-UHFFFAOYSA-N n-pyrrolidin-3-ylbenzamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(=O)NC1CCNC1 XDALBRBPLAEAPK-UHFFFAOYSA-N 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
NBFKNCBRFJKDDR-UHFFFAOYSA-N oct-5-en-2-one Chemical compound CCC=CCCC(C)=O NBFKNCBRFJKDDR-UHFFFAOYSA-N 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
HXEACLLIILLPRG-UHFFFAOYSA-M pipecolate Chemical compound [O-]C(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-M 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 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
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000012552 review Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
206010039447 salmonellosis Diseases 0.000 description 1
238000001004 secondary ion mass spectrometry Methods 0.000 description 1
208000013223 septicemia Diseases 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000012064 sodium phosphate buffer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
KWNDKZADLGFSKE-UHFFFAOYSA-N tert-butyl 3,5-dioxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(=O)CC(=O)C1 KWNDKZADLGFSKE-UHFFFAOYSA-N 0.000 description 1
KCHLWZLPDQXFSA-UHFFFAOYSA-N tert-butyl 3-(phenylmethoxyamino)piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC1NOCC1=CC=CC=C1 KCHLWZLPDQXFSA-UHFFFAOYSA-N 0.000 description 1
VKPDBQCAPWLSPT-UHFFFAOYSA-N tert-butyl 3-[(4-methylphenyl)sulfonylamino]piperidine-1-carboxylate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1CN(C(=O)OC(C)(C)C)CCC1 VKPDBQCAPWLSPT-UHFFFAOYSA-N 0.000 description 1
DTVQYXRBISWVTQ-UHFFFAOYSA-N tert-butyl 3-[2-(4-methylphenyl)sulfonylhydrazinyl]piperidine-1-carboxylate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NNC1CN(C(=O)OC(C)(C)C)CCC1 DTVQYXRBISWVTQ-UHFFFAOYSA-N 0.000 description 1
AKQXKEBCONUWCL-UHFFFAOYSA-N tert-butyl 3-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(N)C1 AKQXKEBCONUWCL-UHFFFAOYSA-N 0.000 description 1
CMIBWIAICVBURI-UHFFFAOYSA-N tert-butyl 3-aminopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)C1 CMIBWIAICVBURI-UHFFFAOYSA-N 0.000 description 1
WSRRJCHATJLAOS-UHFFFAOYSA-N tert-butyl 3-phenylmethoxyimino-2,6-dihydropyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC=CC1=NOCC1=CC=CC=C1 WSRRJCHATJLAOS-UHFFFAOYSA-N 0.000 description 1
LFLSATIDKNWYRN-UHFFFAOYSA-N tert-butyl 3-prop-2-enoxyimino-2,6-dihydropyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC=CC(=NOCC=C)C1 LFLSATIDKNWYRN-UHFFFAOYSA-N 0.000 description 1
CHWMFCCGEWQABK-UHFFFAOYSA-N tert-butyl 7-methyl-3,4-dihydro-2h-1,8-naphthyridine-1-carboxylate Chemical compound C1CCN(C(=O)OC(C)(C)C)C2=NC(C)=CC=C21 CHWMFCCGEWQABK-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
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003568 thioethers Chemical class 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
230000000699 topical effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000017105 transposition Effects 0.000 description 1
HHLJUSLZGFYWKW-UHFFFAOYSA-N triethanolamine hydrochloride Chemical compound Cl.OCCN(CCO)CCO HHLJUSLZGFYWKW-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
GTDZRCHHWHXSRA-UHFFFAOYSA-N triphenyl(prop-1-enyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=CC)C1=CC=CC=C1 GTDZRCHHWHXSRA-UHFFFAOYSA-N 0.000 description 1
125000003960 triphenylenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

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

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Heart & Thoracic Surgery (AREA)
Dermatology (AREA)
Pulmonology (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)

OA1200300019A 2000-08-01 2001-07-24 Composés azabicycliques, leur préparation et leur utilisation comme médicaments, notamment comme anti-bactériens. OA12347A (fr)

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
OA12347A true OA12347A (fr)	2006-05-15

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OA1200300019A OA12347A (fr)	2000-08-01	2001-07-24	Composés azabicycliques, leur préparation et leur utilisation comme médicaments, notamment comme anti-bactériens.

Country Status (41)

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US (5)	US7112592B2 (de)
EP (1)	EP1307457B1 (de)
JP (2)	JP4515704B2 (de)
KR (1)	KR100632906B1 (de)
CN (1)	CN1289500C (de)
AP (1)	AP1614A (de)
AR (1)	AR031716A1 (de)
AT (1)	ATE263768T1 (de)
AU (2)	AU2001279905B2 (de)
BG (1)	BG66094B1 (de)
BR (1)	BRPI0112986B8 (de)
CA (1)	CA2417475C (de)
CR (1)	CR6895A (de)
CZ (1)	CZ294956B6 (de)
DE (1)	DE60102702T2 (de)
DK (1)	DK1307457T3 (de)
DZ (1)	DZ3397A1 (de)
EA (1)	EA004920B1 (de)
EC (1)	ECSP034460A (de)
EE (1)	EE05183B1 (de)
ES (1)	ES2220793T3 (de)
FR (1)	FR2812635B1 (de)
HR (1)	HRP20030034B1 (de)
HU (1)	HU226889B1 (de)
IL (2)	IL154187A0 (de)
MA (1)	MA26938A1 (de)
ME (2)	MEP17108A (de)
MX (1)	MXPA03000881A (de)
NO (1)	NO324940B1 (de)
NZ (1)	NZ523707A (de)
OA (1)	OA12347A (de)
PL (2)	PL234468B1 (de)
PT (1)	PT1307457E (de)
RS (1)	RS50214B (de)
SI (1)	SI1307457T1 (de)
SK (1)	SK287597B6 (de)
TR (1)	TR200400859T4 (de)
TW (1)	TWI292401B (de)
UA (1)	UA73791C2 (de)
WO (1)	WO2002010172A1 (de)
ZA (1)	ZA200300676B (de)

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Publication number	Priority date	Publication date	Assignee	Title
FR2812635B1 (fr) *	2000-08-01	2002-10-11	Aventis Pharma Sa	Nouveaux composes heterocycliques, preparation et utilisation comme medicaments notamment comme anti- bacteriens
FR2835186B1 (fr) *	2002-01-28	2006-10-20	Aventis Pharma Sa	Nouveaux composes heterocycliques, actifs comme inhibiteurs de beta-lactamases
FR2844273B1 (fr) *	2002-09-05	2008-04-04	Aventis Pharma Sa	Nouveaux composes heterocycliques, procede et intermediaires de preparation et utilisation comme medicament, notamment comme inhibiteurs de beta-lactamases et anti-bacteriens.
FR2848210B1 (fr)	2002-12-06	2007-10-19	Aventis Pharma Sa	Nouveaux composes heterocycliques, leur preparation et leur utilisation comme medicaments, notamment comme anti-bacteriens et inhibiteurs de beta-lactamases
US7439253B2 (en)	2002-12-06	2008-10-21	Novexel	Heterocyclic compounds, their preparation and their use as medicaments, in particular as antibacterials and beta-lactamase inhibitors
HRP20110841T1 (hr)	2005-12-07	2012-01-31	Basilea Pharmaceutica Ag	Korisni monobaktamski antibiotici
DK2041156T3 (en)	2006-07-13	2014-02-24	Achillion Pharmaceuticals Inc	4-AMINO-4-OXOBUTANOYL Peptides AS INHIBITORS OF VIRUS REPLICATION
WO2008008398A2 (en) *	2006-07-14	2008-01-17	Shionogi & Co., Ltd.	Oxime compounds and the use thereof
CA2664296A1 (en) *	2006-09-27	2008-04-03	Merck & Co., Inc.	Novel inhibitors of beta-lactamase
CN101589047A (zh) *	2006-10-23	2009-11-25	Irm责任有限公司	组织蛋白酶类抑制剂
US20100056497A1 (en)	2007-01-31	2010-03-04	Dainippon Sumitomo Pharma Co., Ltd	Amide derivative
FR2914923B1 (fr) *	2007-04-12	2013-06-14	Novexel	Nouveaux composes heterocycliques azotes,leur preparation et leur utilisation comme medicaments antibacteriens.
EP2164325B1 (de) *	2007-05-31	2013-04-24	Shionogi&Co., Ltd.	Oxyiminoverbindungen und ihre verwendung
FR2921060B1 (fr) *	2007-09-14	2012-06-15	Novexel	Nouveau procede de preparation d'une piperidine disubsituee et nouveaux intermediaires
CN101918407B (zh) *	2008-01-18	2014-02-26	默沙东公司	β-内酰胺酶抑制剂
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DE60102702T2 (de)	2005-04-07
FR2812635B1 (fr)	2002-10-11
HRP20030034A2 (en)	2004-02-29
CZ294956B6 (cs)	2005-04-13
EA200300211A1 (ru)	2003-06-26
JP2004505088A (ja)	2004-02-19
PT1307457E (pt)	2004-08-31
ES2220793T3 (es)	2004-12-16
TWI292401B (en)	2008-01-11
MEP17108A (en)	2010-06-10
SK287597B6 (sk)	2011-03-04
FR2812635A1 (fr)	2002-02-08
HUP0302943A3 (en)	2007-08-28
SI1307457T1 (en)	2004-08-31
EP1307457B1 (de)	2004-04-07
JP2010138206A (ja)	2010-06-24
KR100632906B1 (ko)	2006-10-13
PL234468B1 (pl)	2020-02-28
US20110021772A1 (en)	2011-01-27
CN1468242A (zh)	2004-01-14
AU7990501A (en)	2002-02-13
BR0112986B1 (pt)	2014-04-01
ECSP034460A (es)	2003-03-10
MXPA03000881A (es)	2003-06-06
EE200300046A (et)	2004-10-15
ME00060B (me)	2010-06-10
PL401469A1 (pl)	2013-02-04
CR6895A (es)	2007-07-12
ATE263768T1 (de)	2004-04-15
US20030199541A1 (en)	2003-10-23
CN1289500C (zh)	2006-12-13
IL154187A (en)	2009-02-11
HUP0302943A2 (hu)	2003-12-29
TR200400859T4 (tr)	2004-06-21
PL216028B1 (pl)	2014-02-28
NZ523707A (en)	2005-02-25
BG107497A (bg)	2003-09-30
EE05183B1 (et)	2009-06-15
AP1614A (en)	2006-05-21
US20060046995A1 (en)	2006-03-02
RS50214B (sr)	2009-07-15
PL365162A1 (en)	2004-12-27
AR031716A1 (es)	2003-10-01
CA2417475A1 (fr)	2002-02-07
ZA200300676B (en)	2004-05-10
US20110213147A1 (en)	2011-09-01
EP1307457A1 (de)	2003-05-07
AP2003002726A0 (en)	2003-06-30
KR20030019642A (ko)	2003-03-06
NO20030494L (no)	2003-03-28
CZ2003223A3 (cs)	2003-08-13
BR0112986A (pt)	2003-07-08
BG66094B1 (bg)	2011-04-29
HRP20030034B1 (hr)	2011-03-31
US7112592B2 (en)	2006-09-26
JP4515704B2 (ja)	2010-08-04
US8178554B2 (en)	2012-05-15
MA26938A1 (fr)	2004-12-20
NO20030494D0 (no)	2003-01-31
HU226889B1 (en)	2010-01-28
YU6303A (sh)	2006-03-03
NO324940B1 (no)	2008-01-07
US7732610B2 (en)	2010-06-08
WO2002010172A1 (fr)	2002-02-07
UA73791C2 (uk)	2005-09-15
IL154187A0 (en)	2003-07-31
DK1307457T3 (da)	2004-08-09
DZ3397A1 (fr)	2002-02-07
US7638529B2 (en)	2009-12-29
AU2001279905B2 (en)	2005-12-08
DE60102702D1 (de)	2004-05-13
CA2417475C (en)	2010-04-20
HK1060356A1 (en)	2004-08-06
EA004920B1 (ru)	2004-10-28
SK1052003A3 (en)	2003-11-04
US20060189652A1 (en)	2006-08-24
BRPI0112986B8 (pt)	2021-05-25

Publication	Publication Date	Title
OA12347A (fr)	2006-05-15	Composés azabicycliques, leur préparation et leur utilisation comme médicaments, notamment comme anti-bactériens.
CA2474043C (fr)	2011-08-02	Composes heterocycliques, actifs comme inhibiteurs de beta-lactamases
US8148540B2 (en)	2012-04-03	Heterocyclic compounds, their preparation and their use as medicaments, in particular as anti-bacterial agents
EP2146994B1 (de)	2015-07-01	Stickstoffhaltige heterocyclische verbindungen, ihre herstellung und ihre verwendung als antibakterielle arzneimittel
CA2507607C (fr)	2014-06-17	Composes heterocycliques, leur preparation et leur utilisation comme medicaments, notamment comme anti-bacteriens et inhibiteurs de beta-lactamases
BR122015020406B1 (pt)	2019-10-29	uso de compostos de formula i como inibidores de beta-lactamases e composições farmaceuticas