JP2012512863A - モノカルバム - Google Patents
モノカルバム Download PDFInfo
- Publication number
- JP2012512863A JP2012512863A JP2011541665A JP2011541665A JP2012512863A JP 2012512863 A JP2012512863 A JP 2012512863A JP 2011541665 A JP2011541665 A JP 2011541665A JP 2011541665 A JP2011541665 A JP 2011541665A JP 2012512863 A JP2012512863 A JP 2012512863A
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- Prior art keywords
- compound
- mmol
- amino
- pharmaceutically acceptable
- formula
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 183
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 239000003242 anti bacterial agent Substances 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
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- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 62
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- 238000006243 chemical reaction Methods 0.000 description 27
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- 235000019253 formic acid Nutrition 0.000 description 19
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- 239000011541 reaction mixture Substances 0.000 description 18
- 230000002194 synthesizing effect Effects 0.000 description 18
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 239000013543 active substance Substances 0.000 description 11
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- MSPCIZMDDUQPGJ-UHFFFAOYSA-N N-methyl-N-(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)N(C)C(=O)C(F)(F)F MSPCIZMDDUQPGJ-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 9
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 9
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- 239000000546 pharmaceutical excipient Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
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- 208000009470 Ventilator-Associated Pneumonia Diseases 0.000 description 7
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- HVFLCNVBZFFHBT-ZKDACBOMSA-N cefepime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1C[N+]1(C)CCCC1 HVFLCNVBZFFHBT-ZKDACBOMSA-N 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000013058 crude material Substances 0.000 description 7
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound 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 description 7
- 229960002260 meropenem Drugs 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 150000003952 β-lactams Chemical class 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000003781 beta lactamase inhibitor Substances 0.000 description 6
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
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- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 5
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- AVAACINZEOAHHE-VFZPANTDSA-N doripenem Chemical compound 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](CNS(N)(=O)=O)C1 AVAACINZEOAHHE-VFZPANTDSA-N 0.000 description 5
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- 150000004677 hydrates Chemical class 0.000 description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
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- XGZWGROCQWUCHU-UHFFFAOYSA-N 3-[4,5-bis(phenylmethoxy)pyridin-2-yl]-4-ethyl-1h-1,2,4-triazol-5-one Chemical compound N1C(=O)N(CC)C(C=2N=CC(OCC=3C=CC=CC=3)=C(OCC=3C=CC=CC=3)C=2)=N1 XGZWGROCQWUCHU-UHFFFAOYSA-N 0.000 description 4
- SEROJOMPCMRBRI-UHFFFAOYSA-N 5-[4,5-bis(phenylmethoxy)pyridin-2-yl]-3h-1,3,4-oxadiazol-2-one Chemical compound O1C(=O)NN=C1C(N=C1)=CC(OCC=2C=CC=CC=2)=C1OCC1=CC=CC=C1 SEROJOMPCMRBRI-UHFFFAOYSA-N 0.000 description 4
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- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 4
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- GCBWDZYSLVSRRI-REOHCLBHSA-N (3s)-3-aminoazetidin-2-one Chemical compound N[C@H]1CNC1=O GCBWDZYSLVSRRI-REOHCLBHSA-N 0.000 description 2
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- KNIWPHSUTGNZST-UHFFFAOYSA-N polymyxin E2 Natural products CC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O KNIWPHSUTGNZST-UHFFFAOYSA-N 0.000 description 1
- 229940041153 polymyxins 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
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229930184609 rhodostreptomycin Natural products 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- TUPFOYXHAYOHIB-YCAIQWGJSA-M sodium;(2s,5r,6r)-6-[[(2r)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;(2s,3s,5r)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]h Chemical compound [Na+].C([C@]1(C)S([C@H]2N(C(C2)=O)[C@H]1C(O)=O)(=O)=O)N1C=CN=N1.O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 TUPFOYXHAYOHIB-YCAIQWGJSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229940010329 spectracef Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- FKENQMMABCRJMK-RITPCOANSA-N sulbactam Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)C[C@H]21 FKENQMMABCRJMK-RITPCOANSA-N 0.000 description 1
- 229960005256 sulbactam Drugs 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 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
- 235000012222 talc Nutrition 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
- 238000010998 test method Methods 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- 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
- 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
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229940104666 zosyn Drugs 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
Classifications
-
- 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
- C07D417/14—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 three or more hetero rings
-
- 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
- A61K31/41—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
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13915908P | 2008-12-19 | 2008-12-19 | |
| US61/139,159 | 2008-12-19 | ||
| PCT/IB2009/055544 WO2010070523A1 (en) | 2008-12-19 | 2009-12-07 | Monocarbams |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012512863A true JP2012512863A (ja) | 2012-06-07 |
| JP2012512863A5 JP2012512863A5 (enExample) | 2012-12-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011541665A Pending JP2012512863A (ja) | 2008-12-19 | 2009-12-07 | モノカルバム |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US8252782B2 (enExample) |
| EP (1) | EP2379546A1 (enExample) |
| JP (1) | JP2012512863A (enExample) |
| KR (1) | KR20110086742A (enExample) |
| CN (1) | CN102325769A (enExample) |
| AR (1) | AR074801A1 (enExample) |
| AU (1) | AU2009329169B2 (enExample) |
| CA (1) | CA2744756C (enExample) |
| IL (1) | IL213216A0 (enExample) |
| MX (1) | MX2011006541A (enExample) |
| PA (1) | PA8855001A1 (enExample) |
| SG (1) | SG171781A1 (enExample) |
| TW (1) | TW201026696A (enExample) |
| UY (1) | UY32336A (enExample) |
| WO (1) | WO2010070523A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2744756C (en) * | 2008-12-19 | 2013-05-28 | Pfizer Inc. | Monocarbams and their use as antibacterial agent |
| JP5777725B2 (ja) | 2010-11-29 | 2015-09-09 | ファイザー・インク | モノバクタム |
| UY34585A (es) * | 2012-01-24 | 2013-09-02 | Aicuris Gmbh & Co Kg | Compuestos b-lactámicos sustituidos con amidina, su preparación y uso |
| AU2016327264B2 (en) | 2015-09-23 | 2019-06-27 | Novartis Ag | Salts and solid forms of monobactam antibiotic |
| CN105481812B (zh) * | 2015-11-30 | 2020-04-21 | 重庆天奕恒化科技有限公司 | 一种5-苄氧基-4-氧代-4h-吡喃-2-羧酸的制备方法 |
| CN110312715A (zh) | 2016-12-21 | 2019-10-08 | 艾库里斯有限及两合公司 | 用于抗生素耐药性细菌菌株感染的使用脒取代的β-内酰胺化合物和β-内酰胺酶抑制剂的组合疗法 |
| ES2912656T3 (es) | 2017-08-02 | 2022-05-26 | Novartis Ag | Proceso para preparar ácido 1-(((Z)-(1-(2-aminotiazol-4-il)-2-oxo-2-(((3S,4R)-2-oxo-4-((2-oxooxazolidin-3-il)metil)-1-sulfoacetidin-3-il)amino)etiliden)amino)oxi)ciclopropano carboxílico |
| US11034648B2 (en) | 2017-08-23 | 2021-06-15 | Helmholtz-Zentrum Für | Cystobactamide derivatives |
| WO2019045085A1 (ja) | 2017-08-31 | 2019-03-07 | 北興化学工業株式会社 | １－（ｎ，ｎ－ジ置換カルバモイル）４－（置換スルホニル）トリアゾリン－５－オン誘導体、４－（ｎ，ｎ－ジ置換カルバモイル）１－（置換スルホニル）トリアゾリン－５－オン誘導体、およびそれらを有効成分として含有する除草剤 |
| EP3747883A4 (en) | 2018-01-29 | 2020-12-16 | Medshine Discovery Inc. | MONOCYCLIC B-LACTAM COMPOUND FOR TREATING BACTERIAL INFECTION |
| WO2020125670A1 (zh) | 2018-12-18 | 2020-06-25 | 南京明德新药研发有限公司 | 单环β-内酰胺化合物在制药中的应用 |
| US12491180B2 (en) | 2019-12-19 | 2025-12-09 | Shenzhen Optimum Biological Technology Co., Ltd | Application of compound in treating pneumonia |
| JP2025513455A (ja) | 2022-04-22 | 2025-04-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | 疼痛の治療のためのヘテロアリール化合物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02502281A (ja) * | 1987-03-03 | 1990-07-26 | ジ・アップジョン・カンパニー | 抗生物質スルホニルアミノカルボニル活性化β‐ラクタム類 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ199981A (en) | 1981-04-09 | 1985-08-16 | Squibb & Sons Inc | 2-oxo-1-(((substituted sulphonyl)amino)carbonyl)azetidines |
| US4587047A (en) * | 1981-04-09 | 1986-05-06 | E. R. Squibb & Sons, Inc. | 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines |
| US5006650A (en) * | 1987-02-11 | 1991-04-09 | The Upjohn Company | Novel N-1 substituted beta-lactams as antibiotics |
| DE3864257D1 (de) | 1987-02-11 | 1991-09-19 | Upjohn Co | Neue n-1 substituierte beta-lactame als antibiotika. |
| US5001235A (en) * | 1987-02-27 | 1991-03-19 | The Upjohn Company | Antibiotic beta-lactams containing a pyridone carboxylic acid or acid derivative |
| US4762922A (en) * | 1987-07-01 | 1988-08-09 | Squibb Corporation | 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines |
| US5015737A (en) * | 1987-07-22 | 1991-05-14 | The Upjohn Company | Therapeutically useful beta-lactams |
| US4777252A (en) * | 1987-08-13 | 1988-10-11 | E. R. Squibb & Sons, Inc. | 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines |
| US4889930A (en) | 1987-12-21 | 1989-12-26 | E. R. Squibb & Sons, Inc. | Process for making 2-oxo-1-((substituted sulfonyl)amino)carbonzyl)azetidines and intermediates used therein |
| JPH01305081A (ja) | 1988-04-04 | 1989-12-08 | E R Squibb & Sons Inc | ３―アシルアミノ―１―［［［（置換スルホニル）アミノ〕カルボニル〕アミノ〕―２―アゼチジノン類 |
| EP0344707A3 (en) | 1988-06-02 | 1990-04-18 | E.R. Squibb & Sons, Inc. | 2-Oxo-1-[[(substituted sulfonyl)-amino]carbonyl]-azetidine derivatives |
| US4959470A (en) * | 1988-08-17 | 1990-09-25 | E. R. Squibb & Sons, Inc. | 2-oxo-[[(substituted sulfonyl)-amino]carbonyl]-azetidines |
| EP0436568A1 (en) | 1988-09-27 | 1991-07-17 | The Upjohn Company | Dihydroxyaryl 4-substituted monocarbams as antibiotics |
| CA2210787A1 (en) | 1997-07-17 | 1999-01-17 | William R. Collier | Self-contained work station |
| BRPI0809147A2 (pt) | 2007-03-23 | 2014-08-26 | Basilea Pharmaceutica Ag | Medicamentos combinados para tratamento de infecções bacterianas |
| CA2744756C (en) * | 2008-12-19 | 2013-05-28 | Pfizer Inc. | Monocarbams and their use as antibacterial agent |
-
2009
- 2009-12-07 CA CA2744756A patent/CA2744756C/en not_active Expired - Fee Related
- 2009-12-07 CN CN2009801569587A patent/CN102325769A/zh active Pending
- 2009-12-07 AU AU2009329169A patent/AU2009329169B2/en not_active Ceased
- 2009-12-07 JP JP2011541665A patent/JP2012512863A/ja active Pending
- 2009-12-07 MX MX2011006541A patent/MX2011006541A/es active IP Right Grant
- 2009-12-07 KR KR1020117013944A patent/KR20110086742A/ko not_active Abandoned
- 2009-12-07 SG SG2011036704A patent/SG171781A1/en unknown
- 2009-12-07 WO PCT/IB2009/055544 patent/WO2010070523A1/en not_active Ceased
- 2009-12-07 EP EP09795553A patent/EP2379546A1/en not_active Withdrawn
- 2009-12-17 UY UY0001032336A patent/UY32336A/es not_active Application Discontinuation
- 2009-12-18 TW TW098143723A patent/TW201026696A/zh unknown
- 2009-12-18 US US12/641,343 patent/US8252782B2/en not_active Expired - Fee Related
- 2009-12-18 PA PA20098855001A patent/PA8855001A1/es unknown
- 2009-12-18 AR ARP090104977A patent/AR074801A1/es not_active Application Discontinuation
-
2011
- 2011-05-30 IL IL213216A patent/IL213216A0/en unknown
-
2012
- 2012-07-26 US US13/558,989 patent/US8324198B1/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02502281A (ja) * | 1987-03-03 | 1990-07-26 | ジ・アップジョン・カンパニー | 抗生物質スルホニルアミノカルボニル活性化β‐ラクタム類 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2744756A1 (en) | 2010-06-24 |
| TW201026696A (en) | 2010-07-16 |
| AU2009329169A1 (en) | 2010-06-24 |
| EP2379546A1 (en) | 2011-10-26 |
| US20100160281A1 (en) | 2010-06-24 |
| CN102325769A (zh) | 2012-01-18 |
| IL213216A0 (en) | 2011-07-31 |
| SG171781A1 (en) | 2011-07-28 |
| US20120289455A1 (en) | 2012-11-15 |
| WO2010070523A1 (en) | 2010-06-24 |
| KR20110086742A (ko) | 2011-07-29 |
| PA8855001A1 (es) | 2010-07-27 |
| US8252782B2 (en) | 2012-08-28 |
| MX2011006541A (es) | 2011-07-20 |
| AU2009329169B2 (en) | 2012-06-28 |
| UY32336A (es) | 2010-07-30 |
| AR074801A1 (es) | 2011-02-16 |
| CA2744756C (en) | 2013-05-28 |
| US8324198B1 (en) | 2012-12-04 |
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