NO327786B1 - Krystallinske 1-metylkarbapenemforbindelser - Google Patents

Krystallinske 1-metylkarbapenemforbindelser Download PDF

Info

Publication number: NO327786B1
Authority: NO; Norway
Prior art keywords: compound; crystalline form; crystalline; methylcarbapenem derivative; formula
Prior art date: 1999-07-06

Application number

NO20020030A

Other languages

English (en)

Norwegian (no)

Other versions

NO20020030L (no

NO20020030D0 (no

Inventor

Isao Kawamoto

Yasuo Shimoji

Hiroshi Fukuhara

Original Assignee

Sankyo Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-07-06

Filing date

2002-01-04

Publication date

2009-09-21

2002-01-04 Application filed by Sankyo Co filed Critical Sankyo Co

2002-01-04 Publication of NO20020030D0 publication Critical patent/NO20020030D0/no

2002-03-05 Publication of NO20020030L publication Critical patent/NO20020030L/no

2009-09-21 Publication of NO327786B1 publication Critical patent/NO327786B1/no

Links

YKMONJZIUAOVEM-GDVGLLTNSA-N (5S)-4-methyl-1-azabicyclo[3.2.0]hept-2-en-7-one Chemical class CC1C=CN2[C@H]1CC2=O YKMONJZIUAOVEM-GDVGLLTNSA-N 0.000 title claims description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 104
150000001875 compounds Chemical class 0.000 claims description 83
239000000243 solution Substances 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 28
238000000634 powder X-ray diffraction Methods 0.000 claims description 22
239000007864 aqueous solution Substances 0.000 claims description 14
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 11
238000001816 cooling Methods 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 6
208000035143 Bacterial infection Diseases 0.000 claims description 5
208000022362 bacterial infectious disease Diseases 0.000 claims description 5
239000001569 carbon dioxide Substances 0.000 claims description 5
229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
238000001556 precipitation Methods 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
239000000203 mixture Substances 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000013078 crystal Substances 0.000 description 29
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
239000000843 powder Substances 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 13
-1 inorganic acid salts Chemical class 0.000 description 11
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
239000010949 copper Substances 0.000 description 10
238000002329 infrared spectrum Methods 0.000 description 10
239000012528 membrane Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000000546 pharmaceutical excipient Substances 0.000 description 7
239000012453 solvate Substances 0.000 description 7
230000001580 bacterial effect Effects 0.000 description 6
230000003115 biocidal effect Effects 0.000 description 6
150000004649 carbonic acid derivatives Chemical class 0.000 description 6
235000008504 concentrate Nutrition 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
239000003480 eluent Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
KEDAXBWZURNCHS-GPODMPQUSA-N (4r,5s,6s)-3-[(3s,5s)-5-[(3s)-3-[[2-(diaminomethylideneamino)acetyl]amino]pyrrolidine-1-carbonyl]-1-methylpyrrolidin-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound O=C([C@@H]1C[C@@H](CN1C)SC=1[C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)N1CC[C@H](NC(=O)CN=C(N)N)C1 KEDAXBWZURNCHS-GPODMPQUSA-N 0.000 description 5
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
229940079593 drug Drugs 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
150000004677 hydrates Chemical class 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
238000012360 testing method Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
YLXDRUQODCBMGR-BWGZFRQBSA-N (4R,5R,6S)-3-diphenylphosphoryloxy-6-[(1R)-1-hydroxyethyl]-4-methyl-4-[(4-nitrophenyl)methyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C[C@H]([C@@H]1[C@@H]2[C@@](C(=C(N2C1=O)C(=O)O)OP(=O)(C3=CC=CC=C3)C4=CC=CC=C4)(C)CC5=CC=C(C=C5)[N+](=O)[O-])O YLXDRUQODCBMGR-BWGZFRQBSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
229910002483 Cu Ka Inorganic materials 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
229920000881 Modified starch Polymers 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
150000003840 hydrochlorides Chemical class 0.000 description 3
235000019426 modified starch Nutrition 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
UENJGVXXQNWWBK-WDSOQIARSA-N s-[(3s,5s)-5-[(3s)-3-[[2-[[amino-[(4-nitrophenyl)methoxycarbonylamino]methylidene]amino]acetyl]amino]pyrrolidine-1-carbonyl]-1-methylpyrrolidin-3-yl] ethanethioate Chemical compound CN1C[C@@H](SC(C)=O)C[C@H]1C(=O)N1C[C@@H](NC(=O)CNC(=N)NC(=O)OCC=2C=CC(=CC=2)[N+]([O-])=O)CC1 UENJGVXXQNWWBK-WDSOQIARSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
239000003826 tablet Substances 0.000 description 3
BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical class OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 2
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
241000589517 Pseudomonas aeruginosa Species 0.000 description 2
241000193998 Streptococcus pneumoniae Species 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
239000008272 agar Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000003708 ampul Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000002775 capsule Substances 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000010908 decantation Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000003113 dilution method Methods 0.000 description 2
239000007884 disintegrant Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000001802 infusion Methods 0.000 description 2
229960004393 lidocaine hydrochloride Drugs 0.000 description 2
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 2
239000003589 local anesthetic agent Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
239000008176 lyophilized powder Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
239000002674 ointment Substances 0.000 description 2
230000003204 osmotic effect Effects 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000011343 solid material Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
229940031000 streptococcus pneumoniae Drugs 0.000 description 2
238000011200 topical administration Methods 0.000 description 2
241001148471 unidentified anaerobic bacterium Species 0.000 description 2
GYAJUSQMNLTTEY-XIRDDKMYSA-N (4-nitrophenyl)methyl n-[n'-[2-[[(3s)-1-[(2s,4s)-1-methyl-4-sulfanylpyrrolidine-2-carbonyl]pyrrolidin-3-yl]amino]-2-oxoethyl]carbamimidoyl]carbamate Chemical compound CN1C[C@@H](S)C[C@H]1C(=O)N1C[C@@H](NC(=O)CNC(=N)NC(=O)OCC=2C=CC(=CC=2)[N+]([O-])=O)CC1 GYAJUSQMNLTTEY-XIRDDKMYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000606124 Bacteroides fragilis Species 0.000 description 1
108020004256 Beta-lactamase Proteins 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
229920002785 Croscarmellose sodium Polymers 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
241000588921 Enterobacteriaceae Species 0.000 description 1
241000194033 Enterococcus Species 0.000 description 1
208000007882 Gastritis Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000590002 Helicobacter pylori Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
239000004368 Modified starch Substances 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
239000004373 Pullulan Substances 0.000 description 1
229920001218 Pullulan Polymers 0.000 description 1
241000607720 Serratia Species 0.000 description 1
241000607764 Shigella dysenteriae Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
240000004922 Vigna radiata Species 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
YFHNDHXQDJQEEE-UHFFFAOYSA-N acetic acid;hydrazine Chemical compound NN.CC(O)=O YFHNDHXQDJQEEE-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000002535 acidifier Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
208000023652 chronic gastritis Diseases 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
150000001868 cobalt Chemical class 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000003193 general anesthetic agent Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229940037467 helicobacter pylori Drugs 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
159000000014 iron salts Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
229960003511 macrogol Drugs 0.000 description 1
229940037627 magnesium lauryl sulfate Drugs 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
HBNDBUATLJAUQM-UHFFFAOYSA-L magnesium;dodecyl sulfate Chemical compound [Mg+2].CCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCOS([O-])(=O)=O HBNDBUATLJAUQM-UHFFFAOYSA-L 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
229960002660 mepivacaine hydrochloride Drugs 0.000 description 1
RETIMRUQNCDCQB-UHFFFAOYSA-N mepivacaine hydrochloride Chemical compound Cl.CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C RETIMRUQNCDCQB-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
229960003085 meticillin Drugs 0.000 description 1
150000002815 nickel Chemical class 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000003891 oxalate salts Chemical class 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
150000002989 phenols Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
235000019423 pullulan Nutrition 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000013074 reference sample Substances 0.000 description 1
UGOXITGUCYPVOH-HRNNMHKYSA-N s-[(3s,5s)-5-[(3s)-3-[[2-[bis[(4-nitrophenyl)methoxycarbonylamino]methylideneamino]acetyl]amino]pyrrolidine-1-carbonyl]-1-methylpyrrolidin-3-yl] ethanethioate Chemical compound CN1C[C@@H](SC(C)=O)C[C@H]1C(=O)N1C[C@@H](NC(=O)CNC(NC(=O)OCC=2C=CC(=CC=2)[N+]([O-])=O)=NC(=O)OCC=2C=CC(=CC=2)[N+]([O-])=O)CC1 UGOXITGUCYPVOH-HRNNMHKYSA-N 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000009738 saturating Methods 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
NGHMEZWZOZEZOH-UHFFFAOYSA-N silicic acid;hydrate Chemical compound O.O[Si](O)(O)O NGHMEZWZOZEZOH-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
OIIWPAYIXDCDNL-UHFFFAOYSA-M sodium 3-(trimethylsilyl)propionate Chemical compound [Na+].C[Si](C)(C)CCC([O-])=O OIIWPAYIXDCDNL-UHFFFAOYSA-M 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000013112 stability test Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Communicable Diseases (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO20020030A 1999-07-06 2002-01-04 Krystallinske 1-metylkarbapenemforbindelser NO327786B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP19136899		1999-07-06
PCT/JP2000/004496 WO2001002401A1 (en)	1999-07-06	2000-07-06	Crystalline 1-methylcarbapenem compounds

Publications (3)

Publication Number	Publication Date
NO20020030D0 NO20020030D0 (no)	2002-01-04
NO20020030L NO20020030L (no)	2002-03-05
NO327786B1 true NO327786B1 (no)	2009-09-21

Family

ID=16273433

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20020030A NO327786B1 (no)	1999-07-06	2002-01-04	Krystallinske 1-metylkarbapenemforbindelser

Country Status (21)

Country	Link
US (3)	US20020128254A1 (es)
EP (1)	EP1193269A4 (es)
JP (1)	JP3476420B2 (es)
KR (1)	KR100750552B1 (es)
CN (2)	CN100360530C (es)
AU (1)	AU758190B2 (es)
BR (1)	BR0012253A (es)
CA (1)	CA2378483C (es)
CZ (1)	CZ20014731A3 (es)
HK (1)	HK1044768A1 (es)
HU (1)	HUP0202255A3 (es)
IL (2)	IL147214A0 (es)
MX (1)	MXPA02000061A (es)
NO (1)	NO327786B1 (es)
NZ (1)	NZ516310A (es)
PL (1)	PL352296A1 (es)
RU (2)	RU2214411C2 (es)
TR (2)	TR200403436T2 (es)
TW (1)	TWI250160B (es)
WO (1)	WO2001002401A1 (es)
ZA (1)	ZA200110413B (es)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20020060067A (ko)	1999-04-06	2002-07-16	가와무라 요시부미	α-치환 카르복실산 유도체
US7041660B2 (en) *	1999-07-06	2006-05-09	Sankyo Company, Limited	Crystalline 1-methylcarbapenem derivatives
ATE267831T1 (de) *	1999-09-30	2004-06-15	Otsuka Kagaku Kk	Kristalle von cephemderivaten und verfahren zu ihrer herstellung
PT1294361E (pt)	2000-06-21	2011-07-26	Cubist Pharm Inc	Composições e métodos para melhorar a absorção oral de agentes antimicrobianos
KR100451672B1 (ko) *	2001-06-05	2004-10-08	한미약품 주식회사	결정성 세프디니르 산부가염, 이의 제조방법 및 이를이용한 세프디니르의 제조방법
EP1426376A4 (en) *	2001-08-13	2004-12-22	Eisai Co Ltd	PROCESS FOR THE PREPARATION OF CARBAPENEM-BASED ANTIBIOTICS
HRP20040264B1 (en) *	2001-09-26	2012-07-31	Merck@Sharp@@@Dohme@Corp	Process for making carbapenem compounds
ATE518864T1 (de) *	2001-09-26	2011-08-15	Merck Sharp & Dohme	Verfahren zur herstellung von carbapenemverbindungen
ITMI20012364A1 (it) *	2001-11-09	2003-05-09	Antibioticos Spa	Processo di sintesi della cefixima via alchil-o arilsolfonati
CN100475817C (zh) *	2003-08-25	2009-04-08	三共株式会社	1-甲基碳青霉烯化合物的结晶
JP2005097278A (ja) *	2003-08-25	2005-04-14	Sankyo Co Ltd	１−メチルカルバペネム化合物の結晶
EP1776365B1 (en) *	2004-06-02	2011-08-03	Sandoz Ag	Meropenem intermediate in crystalline form
EP1862456A4 (en) *	2005-03-22	2010-01-27	Daiichi Sankyo Co Ltd	PROCESS FOR PREPARING A CARBAPENE DERIVATIVE WITH 1-ALKYLPYRROLIDINE STRUCTURE
US8968781B2 (en)	2005-04-29	2015-03-03	Cubist Pharmaceuticals, Inc.	Therapeutic compositions
JPWO2006121151A1 (ja) *	2005-05-13	2008-12-18	第一三共株式会社	１−メチルカルバペネム化合物の結晶
CN101328179B (zh) *	2007-06-15	2011-01-12	山东轩竹医药科技有限公司	含有氧代氮杂环的巯基吡咯烷培南衍生物
CN101412717B (zh) *	2007-10-19	2011-01-12	山东轩竹医药科技有限公司	含有胍基烷酰胺基杂环的碳青霉烯衍生物
WO2009091031A1 (ja) *	2008-01-17	2009-07-23	Dainippon Sumitomo Pharma Co., Ltd.	アデニン化合物の製造方法
WO2011143935A1 (zh) *	2010-05-21	2011-11-24	山东轩竹医药科技有限公司	碳青霉烯衍生物或其水合物的晶型及其制备方法与用途
US8822445B2 (en) *	2010-06-03	2014-09-02	Xuanzhu Pharma Co., Ltd.	Crystalline form of carbapenem derivative or its hydrates and preparation methods and uses thereof
EP2945929B1 (de) *	2013-01-15	2020-01-22	Merck Patent GmbH	Acylguanidine zur behandlung von arthrose

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4260543A (en)	1978-07-03	1981-04-07	Merck & Co., Inc.	Crystalline N-formimidoyl thienamycin
US4748238A (en)	1984-03-14	1988-05-31	Merck & Co., Inc.	Crystalline 1R,5S,6S,8R-1-methyl-2-(N,N-dimethylcarbamimidoylmethylthio)-6-(1-hydroxyethyl)-1-carbapen-2-em-3-carboxylic acid
US4713451A (en)	1984-04-09	1987-12-15	Merck & Co., Inc.	Crystalline dimethyliminothienamycin
IE60588B1 (en)	1986-07-30	1994-07-27	Sumitomo Pharma	Carbapenem compound in crystalline form, and its production and use
US4866171A (en)	1987-04-11	1989-09-12	Lederle (Japan), Ltd.	(1R,5S,6S)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)]thio-6-[R-1-hydroxyethyl]-1-methyl-carbapenum-3-carboxylate
CA2036163C (en) *	1990-02-14	2001-06-19	Makoto Sunagawa	Novel beta-lactam compounds and their production
TW209220B (es) *	1991-11-27	1993-07-11	Manyu Seiyaku Kk
GB9202298D0 (en) *	1992-02-04	1992-03-18	Ici Plc	Antibiotic compounds
DE69324106T2 (de)	1992-11-17	1999-12-09	Sankyo Co., Ltd.	Krystallines Carbapenemderivat
JPH06336483A (ja) *	1993-05-26	1994-12-06	Banyu Pharmaceut Co Ltd	アミノアルキルピロリジニルチオカルバペネム誘導体
JPH07291973A (ja) *	1994-04-27	1995-11-07	Banyu Pharmaceut Co Ltd	新規な２−ピロリジニルチオカルバペネム誘導体
JPH09110869A (ja) *	1995-10-23	1997-04-28	Lederle Japan Ltd	カルバペネム化合物
DK0882728T3 (da) *	1995-12-21	2003-01-06	Sankyo Co	1-methylcarbapenemderivater
JP2955276B2 (ja) *	1997-06-19	1999-10-04	三共株式会社	１−メチルカルバペネム誘導体を含有する抗菌剤

2000
- 2000-07-05 TW TW089113337A patent/TWI250160B/zh not_active IP Right Cessation
- 2000-07-06 TR TR2004/03436T patent/TR200403436T2/xx unknown
- 2000-07-06 BR BR0012253-0A patent/BR0012253A/pt not_active Application Discontinuation
- 2000-07-06 EP EP00944289A patent/EP1193269A4/en not_active Withdrawn
- 2000-07-06 KR KR1020027000117A patent/KR100750552B1/ko not_active Expired - Fee Related
- 2000-07-06 HU HU0202255A patent/HUP0202255A3/hu unknown
- 2000-07-06 HK HK02106273.3A patent/HK1044768A1/en unknown
- 2000-07-06 RU RU2002100058/04A patent/RU2214411C2/ru not_active IP Right Cessation
- 2000-07-06 MX MXPA02000061A patent/MXPA02000061A/es active IP Right Grant
- 2000-07-06 CN CNB008124558A patent/CN100360530C/zh not_active Expired - Fee Related
- 2000-07-06 NZ NZ516310A patent/NZ516310A/en not_active IP Right Cessation
- 2000-07-06 CZ CZ20014731A patent/CZ20014731A3/cs unknown
- 2000-07-06 IL IL14721400A patent/IL147214A0/xx unknown
- 2000-07-06 TR TR2002/00100T patent/TR200200100T2/xx unknown
- 2000-07-06 CA CA002378483A patent/CA2378483C/en not_active Expired - Fee Related
- 2000-07-06 PL PL00352296A patent/PL352296A1/xx not_active Application Discontinuation
- 2000-07-06 JP JP2000204430A patent/JP3476420B2/ja not_active Expired - Fee Related
- 2000-07-06 WO PCT/JP2000/004496 patent/WO2001002401A1/ja not_active Ceased
- 2000-07-06 CN CNA2007101096355A patent/CN101077869A/zh active Pending
- 2000-07-06 AU AU58487/00A patent/AU758190B2/en not_active Ceased
2001
- 2001-12-19 ZA ZA200110413A patent/ZA200110413B/xx unknown
- 2001-12-20 IL IL147214A patent/IL147214A/en not_active IP Right Cessation
- 2001-12-28 US US10/034,548 patent/US20020128254A1/en not_active Abandoned
2002
- 2002-01-04 NO NO20020030A patent/NO327786B1/no not_active IP Right Cessation
2003
- 2003-01-27 US US10/351,944 patent/US6924279B2/en not_active Expired - Fee Related
- 2003-04-03 US US10/407,546 patent/US20030232803A1/en not_active Abandoned
- 2003-06-18 RU RU2003118411/04A patent/RU2003118411A/ru not_active Application Discontinuation

Also Published As

Publication number	Publication date
KR100750552B1 (ko)	2007-08-20
MXPA02000061A (es)	2002-07-02
WO2001002401A1 (en)	2001-01-11
IL147214A0 (en)	2002-08-14
CA2378483C (en)	2008-09-16
US6924279B2 (en)	2005-08-02
TWI250160B (en)	2006-03-01
HK1044768A1 (en)	2002-11-01
CN100360530C (zh)	2008-01-09
AU5848700A (en)	2001-01-22
JP3476420B2 (ja)	2003-12-10
JP2001072681A (ja)	2001-03-21
HUP0202255A2 (en)	2002-10-28
AU758190B2 (en)	2003-03-20
TR200403436T2 (tr)	2005-03-21
IL147214A (en)	2009-12-24
PL352296A1 (en)	2003-08-11
CA2378483A1 (en)	2001-01-11
CN1372560A (zh)	2002-10-02
CZ20014731A3 (cs)	2002-04-17
RU2003118411A (ru)	2004-12-20
US20020128254A1 (en)	2002-09-12
US20030232803A1 (en)	2003-12-18
CN101077869A (zh)	2007-11-28
KR20020022761A (ko)	2002-03-27
EP1193269A1 (en)	2002-04-03
ZA200110413B (en)	2003-03-19
HUP0202255A3 (en)	2003-10-28
US20030158174A1 (en)	2003-08-21
TR200200100T2 (tr)	2002-05-21
BR0012253A (pt)	2002-03-26
RU2214411C2 (ru)	2003-10-20
NO20020030L (no)	2002-03-05
NZ516310A (en)	2004-05-28
NO20020030D0 (no)	2002-01-04
EP1193269A4 (en)	2003-05-28

Publication	Publication Date	Title
NO327786B1 (no)	2009-09-21	Krystallinske 1-metylkarbapenemforbindelser
JP3375084B2 (ja)	2003-02-10	ピロリジルチオカルバペネム誘導体の新型結晶
EP1784407A1 (en)	2007-05-16	2-arylmethylazetidine carbapenem derivatives and preparation thereof
JP3681116B2 (ja)	2005-08-10	結晶性カルバペネム化合物を含有する抗菌剤
US7041660B2 (en)	2006-05-09	Crystalline 1-methylcarbapenem derivatives
US7534782B2 (en)	2009-05-19	Crystal of 1-methylcarbapenem solvate
US20080227768A1 (en)	2008-09-18	Crystal of 1-Methylcarbapenem Compound
JP2008143887A (ja)	2008-06-26	１−メチルカルバペネム化合物の結晶を含有する医薬
HK1085213A (en)	2006-08-18	Crystal of 1-methyl carbapenem compound
HU211964A9 (hu)	1996-01-29	Az átmeneti oltalom az 1-5. és 9. igénypontokra vonatkozik.
JPH09110869A (ja)	1997-04-28	カルバペネム化合物
JP2005097278A (ja)	2005-04-14	１−メチルカルバペネム化合物の結晶
JP2003183281A (ja)	2003-07-03	カルバペネム化合物
JP2010013356A (ja)	2010-01-21	結晶性カルバペネム化合物
JP2006265235A (ja)	2006-10-05	１−メチルカルバペネム化合物の結晶を含有する医薬
JPH07109278A (ja)	1995-04-25	結晶性カルバペネム誘導体
JP2000264886A (ja)	2000-09-26	カルバペネムエステル化合物

Legal Events

Date	Code	Title	Description
2012-02-20	MM1K	Lapsed by not paying the annual fees