BR112020001327A2 - compostos químicos - Google Patents
compostos químicos Download PDFInfo
- Publication number
- BR112020001327A2 BR112020001327A2 BR112020001327-7A BR112020001327A BR112020001327A2 BR 112020001327 A2 BR112020001327 A2 BR 112020001327A2 BR 112020001327 A BR112020001327 A BR 112020001327A BR 112020001327 A2 BR112020001327 A2 BR 112020001327A2
- Authority
- BR
- Brazil
- Prior art keywords
- carboxylic acid
- amino
- fluoro
- thiazole
- phenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 237
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 53
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 52
- 238000011282 treatment Methods 0.000 claims abstract description 38
- 230000002265 prevention Effects 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- -1 2-guanidinoacetyl Chemical group 0.000 claims description 240
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 135
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- 125000001424 substituent group Chemical group 0.000 claims description 85
- 125000000623 heterocyclic group Chemical group 0.000 claims description 71
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 61
- 239000003242 anti bacterial agent Substances 0.000 claims description 60
- 229940088710 antibiotic agent Drugs 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- 241000894006 Bacteria Species 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 44
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- 229960002260 meropenem Drugs 0.000 claims description 38
- 125000004429 atom Chemical group 0.000 claims description 37
- 230000003115 biocidal effect Effects 0.000 claims description 37
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical group C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 claims description 37
- 229920006395 saturated elastomer Polymers 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 34
- 125000002947 alkylene group Chemical group 0.000 claims description 26
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 125000004450 alkenylene group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 241000588747 Klebsiella pneumoniae Species 0.000 claims description 13
- 229940123930 Lactamase inhibitor Drugs 0.000 claims description 11
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 10
- BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical group OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 claims description 9
- 241000588921 Enterobacteriaceae Species 0.000 claims description 9
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 9
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- 229960002379 avibactam Drugs 0.000 claims description 8
- NDCUAPJVLWFHHB-UHNVWZDZSA-N avibactam Chemical compound C1N2[C@H](C(N)=O)CC[C@@]1([H])N(OS(O)(=O)=O)C2=O NDCUAPJVLWFHHB-UHNVWZDZSA-N 0.000 claims description 8
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 229930186147 Cephalosporin Natural products 0.000 claims description 7
- 229940124587 cephalosporin Drugs 0.000 claims description 7
- 150000001780 cephalosporins Chemical class 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 7
- YCZPXRQPDCXTIO-BBBLOLIVSA-N [(2s,5r)-7-oxo-2-[[[(3r)-piperidine-3-carbonyl]amino]carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound O=C([C@H]1N2C[C@@H](CC1)N(C2=O)OS(=O)(=O)O)NNC(=O)[C@@H]1CCCNC1 YCZPXRQPDCXTIO-BBBLOLIVSA-N 0.000 claims description 6
- RSBPYSTVZQAADE-RQJHMYQMSA-N nacubactam Chemical compound C1N2[C@H](C(=O)NOCCN)CC[C@@]1([H])N(OS(O)(=O)=O)C2=O RSBPYSTVZQAADE-RQJHMYQMSA-N 0.000 claims description 6
- 229950005001 nacubactam Drugs 0.000 claims description 6
- 229950007224 zidebactam Drugs 0.000 claims description 6
- 229930182555 Penicillin Natural products 0.000 claims description 5
- 241000947836 Pseudomonadaceae Species 0.000 claims description 5
- 150000002960 penicillins Chemical class 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- 241000589289 Moraxellaceae Species 0.000 claims description 4
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 4
- 229940041011 carbapenems Drugs 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 241000588626 Acinetobacter baumannii Species 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 241000589513 Burkholderia cepacia Species 0.000 claims description 2
- 201000008225 Klebsiella pneumonia Diseases 0.000 claims description 2
- 206010035717 Pneumonia klebsiella Diseases 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 235000002046 Hedeoma drummondii Nutrition 0.000 claims 1
- 244000139725 Hedeoma drummondii Species 0.000 claims 1
- 239000003781 beta lactamase inhibitor Substances 0.000 claims 1
- 229940126813 beta-lactamase inhibitor Drugs 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 150000002961 penems Chemical class 0.000 claims 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract description 8
- 150000007979 thiazole derivatives Chemical group 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 170
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 131
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 106
- 239000011541 reaction mixture Substances 0.000 description 104
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 98
- 239000000243 solution Substances 0.000 description 92
- 239000007787 solid Substances 0.000 description 87
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 86
- 230000002829 reductive effect Effects 0.000 description 85
- 102000004190 Enzymes Human genes 0.000 description 67
- 108090000790 Enzymes Proteins 0.000 description 67
- 235000019253 formic acid Nutrition 0.000 description 66
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 65
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- 239000012043 crude product Substances 0.000 description 52
- 239000003112 inhibitor Substances 0.000 description 48
- 238000002953 preparative HPLC Methods 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 235000019439 ethyl acetate Nutrition 0.000 description 42
- 239000000047 product Substances 0.000 description 41
- 238000005160 1H NMR spectroscopy Methods 0.000 description 34
- 238000000034 method Methods 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 31
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- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 31
- 239000013058 crude material Substances 0.000 description 29
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 28
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 26
- 239000012044 organic layer Substances 0.000 description 25
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 24
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 24
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 23
- 238000003818 flash chromatography Methods 0.000 description 22
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 21
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 19
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 17
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 9
- 102100035679 Inositol monophosphatase 1 Human genes 0.000 description 9
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- 125000003118 aryl group Chemical group 0.000 description 9
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- 125000005842 heteroatom Chemical group 0.000 description 9
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- 239000011734 sodium Substances 0.000 description 9
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- 239000000706 filtrate Substances 0.000 description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 7
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
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- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 1
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- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- IQSYKHVFMYGJER-UHFFFAOYSA-N tert-butyl 2-isocyanoacetate Chemical compound CC(C)(C)OC(=O)C[N+]#[C-] IQSYKHVFMYGJER-UHFFFAOYSA-N 0.000 description 1
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- DRDVJQOGFWAVLH-UHFFFAOYSA-N tert-butyl n-hydroxycarbamate Chemical compound CC(C)(C)OC(=O)NO DRDVJQOGFWAVLH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
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- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
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- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
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- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
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- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
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- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
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- A—HUMAN NECESSITIES
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Life Sciences & Earth Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
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| EP17305973.4A EP3431474A1 (en) | 2017-07-21 | 2017-07-21 | Chemical compounds |
| EP17305973.4 | 2017-07-21 | ||
| EP18290003.5 | 2018-01-08 | ||
| EP18290003 | 2018-01-08 | ||
| EP18150903 | 2018-01-09 | ||
| EP18150903.5 | 2018-01-09 | ||
| PCT/EP2018/069827 WO2019016393A1 (en) | 2017-07-21 | 2018-07-20 | CHEMICAL COMPOUNDS |
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| BR112020001327A2 true BR112020001327A2 (pt) | 2020-08-11 |
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| EP (1) | EP3655405B1 (https=) |
| JP (1) | JP2020528412A (https=) |
| KR (1) | KR20200030584A (https=) |
| CN (2) | CN115745910B (https=) |
| AU (1) | AU2018304907B2 (https=) |
| BR (1) | BR112020001327A2 (https=) |
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| SG (1) | SG11202000217QA (https=) |
| WO (1) | WO2019016393A1 (https=) |
| ZA (1) | ZA202000529B (https=) |
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| US11905286B2 (en) | 2018-08-09 | 2024-02-20 | Antabio Sas | Diazabicyclooctanones as inhibitors of serine beta-lactamases |
| EP3833665B1 (en) | 2018-08-09 | 2023-07-19 | Antabio SAS | Diazabicyclooctanones as inhibitors of serine beta-lactamases |
| CN110878032B (zh) * | 2019-10-31 | 2022-03-15 | 苏州诚和医药化学有限公司 | 一种n-苄基乙脒盐酸盐的合成方法 |
| CN110713459A (zh) * | 2019-12-04 | 2020-01-21 | 西南大学 | 一类喹啉酮富马来酰胺衍生物的设计合成与应用 |
| KR102874744B1 (ko) | 2020-03-12 | 2025-10-22 | 주식회사 엘지에너지솔루션 | 에너지 밀도가 향상된 전지 모듈 및 이를 포함하는 전지 팩 |
| CN115745838B (zh) * | 2022-10-27 | 2023-12-22 | 苏州诚和医药化学有限公司 | 一种脒类化合物及n-苄基乙脒盐酸盐的合成方法 |
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| WO2002000651A2 (en) | 2000-06-27 | 2002-01-03 | Bristol-Myers Squibb Pharma Company | Factor xa inhibitors |
| KR20090090406A (ko) | 2000-12-18 | 2009-08-25 | 가부시키가이샤 이야쿠 분지 셋케이 겐쿠쇼 | 염증성 사이토카인 생산 유리 억제제 |
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| JP2009513523A (ja) | 2003-07-08 | 2009-04-02 | ノバルティス アクチエンゲゼルシャフト | ベンゼンスルホニルアミノ化合物およびそれらを含む医薬組成物 |
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| KR20160115946A (ko) | 2014-02-03 | 2016-10-06 | 욱크하르트 리미티드 | (2s,5r)-1,6-다이아자-바이사이클로[3.2.1]옥테인-2-카보나이트릴-7-옥소-6-(설포옥시)-모노 소듐 염의 제조 공정 |
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2018
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2022
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| CA3070036A1 (en) | 2019-01-24 |
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| ES2946917T3 (es) | 2023-07-27 |
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| US20220315546A1 (en) | 2022-10-06 |
| AU2018304907B2 (en) | 2022-11-24 |
| ZA202000529B (en) | 2023-07-26 |
| EP3655405C0 (en) | 2023-06-07 |
| MX2020000576A (es) | 2020-09-10 |
| CN115745910A (zh) | 2023-03-07 |
| KR20200030584A (ko) | 2020-03-20 |
| CN110446708A (zh) | 2019-11-12 |
| EP3655405A1 (en) | 2020-05-27 |
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