SI9300574A - 6-(substituted-methylene)penems with pharmaceutical properties - Google Patents
6-(substituted-methylene)penems with pharmaceutical properties Download PDFInfo
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- SI9300574A SI9300574A SI9300574A SI9300574A SI9300574A SI 9300574 A SI9300574 A SI 9300574A SI 9300574 A SI9300574 A SI 9300574A SI 9300574 A SI9300574 A SI 9300574A SI 9300574 A SI9300574 A SI 9300574A
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- 150000002961 penems Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000001424 substituent group Chemical group 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 4
- 150000001768 cations Chemical class 0.000 claims abstract description 4
- -1 1-benzazol-6-yl Chemical group 0.000 claims description 91
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000011734 sodium Substances 0.000 claims description 26
- 229910052708 sodium Inorganic materials 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- 230000003115 biocidal effect Effects 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 9
- 150000003462 sulfoxides Chemical class 0.000 claims description 9
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims description 7
- 150000003457 sulfones Chemical class 0.000 claims description 7
- 208000035143 Bacterial infection Diseases 0.000 claims description 6
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000002217 penem group Chemical group 0.000 claims description 3
- 238000006894 reductive elimination reaction Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 5
- 125000001174 sulfone group Chemical group 0.000 claims 2
- DMEYZPJEFHGESJ-CPWLGJMPSA-M (5R,6Z)-6-(6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [O-]C(=O)C1=CS[C@H]2N1C(=O)\C2=C\C1=CN2CCOCC2=N1 DMEYZPJEFHGESJ-CPWLGJMPSA-M 0.000 claims 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910001415 sodium ion Inorganic materials 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
- 239000000203 mixture Substances 0.000 description 92
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 77
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 59
- 239000000243 solution Substances 0.000 description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 34
- 230000002829 reductive effect Effects 0.000 description 33
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 32
- 239000012071 phase Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 150000001299 aldehydes Chemical class 0.000 description 24
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000008346 aqueous phase Substances 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
- 229910052786 argon Inorganic materials 0.000 description 16
- 238000004587 chromatography analysis Methods 0.000 description 16
- 235000017557 sodium bicarbonate Nutrition 0.000 description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- 229930182555 Penicillin Natural products 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- 229930186147 Cephalosporin Natural products 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 229940124587 cephalosporin Drugs 0.000 description 11
- 150000001780 cephalosporins Chemical class 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000006260 foam Substances 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 150000002960 penicillins Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000003039 volatile agent Substances 0.000 description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 229960003022 amoxicillin Drugs 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 6
- 229940049954 penicillin Drugs 0.000 description 6
- 239000001509 sodium citrate Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 6
- 229940038773 trisodium citrate Drugs 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 5
- 150000002500 ions Chemical group 0.000 description 5
- 150000004965 peroxy acids Chemical class 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- PPZFMKBUJLVNLH-ZWNOBZJWSA-N C1=CC(OC)=CC=C1CC1=C(C(O)=O)N2C(=O)[C@@H](Br)[C@H]2S1 Chemical compound C1=CC(OC)=CC=C1CC1=C(C(O)=O)N2C(=O)[C@@H](Br)[C@H]2S1 PPZFMKBUJLVNLH-ZWNOBZJWSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 229960000723 ampicillin Drugs 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
- 238000011260 co-administration Methods 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 229910052724 xenon Inorganic materials 0.000 description 4
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 4
- KIWYZTVZAJFYST-ZCFIWIBFSA-N (5R)-6-methylidene-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CS[C@@H]2C(=C)C(=O)N12 KIWYZTVZAJFYST-ZCFIWIBFSA-N 0.000 description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
- 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 3
- 241001465754 Metazoa Species 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 125000003172 aldehyde group Chemical group 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 239000006286 aqueous extract Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229960003669 carbenicillin Drugs 0.000 description 3
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 150000007942 carboxylates Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- PPWLZLNTPVSKLB-UHFFFAOYSA-N ethyl 6,7-dihydro-5h-imidazo[2,1-b][1,3]thiazine-2-carboxylate Chemical compound C1CCSC2=NC(C(=O)OCC)=CN21 PPWLZLNTPVSKLB-UHFFFAOYSA-N 0.000 description 3
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000004468 heterocyclylthio group Chemical group 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 229960004659 ticarcillin Drugs 0.000 description 3
- 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 3
- YGYVLHRWDBODQZ-UHFFFAOYSA-N (1,1-dioxo-2,3-dihydroimidazo[2,1-b][1,3]thiazol-6-yl)methanol Chemical compound C1CS(=O)(=O)C2=NC(CO)=CN21 YGYVLHRWDBODQZ-UHFFFAOYSA-N 0.000 description 2
- WRFCGBVLTRJBKN-QSNWEANLSA-N (2s,5r,6r)-6-[[(2r)-2-[[2-[[amino(pyridin-4-yl)methylidene]amino]acetyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC=CC=1)C(=O)CN=C(N)C1=CC=NC=C1 WRFCGBVLTRJBKN-QSNWEANLSA-N 0.000 description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- PODIRZNXZPJLBU-UHFFFAOYSA-N 1,1-dioxo-2,3-dihydroimidazo[2,1-b][1,3]thiazole-6-carbaldehyde Chemical compound C1CS(=O)(=O)C2=NC(C=O)=CN21 PODIRZNXZPJLBU-UHFFFAOYSA-N 0.000 description 2
- JSUDYMLJEPHJCU-UHFFFAOYSA-N 2,3-dihydroimidazo[2,1-b][1,3]thiazole-6-carbaldehyde Chemical compound C1CSC2=NC(C=O)=CN21 JSUDYMLJEPHJCU-UHFFFAOYSA-N 0.000 description 2
- KVFVJJCPCQOSEM-UHFFFAOYSA-N 2h-1,3-thiazine-2-carbaldehyde Chemical compound O=CC1SC=CC=N1 KVFVJJCPCQOSEM-UHFFFAOYSA-N 0.000 description 2
- RIKHJARBFAVIHT-UHFFFAOYSA-N 8,8-dioxo-6,7-dihydro-5h-imidazo[2,1-b][1,3]thiazine-2-carbaldehyde Chemical compound C1CCS(=O)(=O)C2=NC(C=O)=CN21 RIKHJARBFAVIHT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- RDLPVSKMFDYCOR-UEKVPHQBSA-N cephradine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CCC=CC1 RDLPVSKMFDYCOR-UEKVPHQBSA-N 0.000 description 1
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- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
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- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
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- 229960002457 epicillin Drugs 0.000 description 1
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- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- DCNDODRWJORREI-UHFFFAOYSA-N ethyl 2,3-dihydroimidazo[2,1-b][1,3]thiazole-6-carboxylate Chemical compound C1CSC2=NC(C(=O)OCC)=CN21 DCNDODRWJORREI-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical group COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
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- 125000004043 oxo group Chemical group O=* 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
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- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229960002292 piperacillin Drugs 0.000 description 1
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- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000001120 potassium sulphate Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 229960003672 propicillin Drugs 0.000 description 1
- HOCWPKXKMNXINF-XQERAMJGSA-N propicillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(CC)OC1=CC=CC=C1 HOCWPKXKMNXINF-XQERAMJGSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- PAYGMRRPBHYIMA-UHFFFAOYSA-N sodium;trihydrate Chemical compound O.O.O.[Na] PAYGMRRPBHYIMA-UHFFFAOYSA-N 0.000 description 1
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- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
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- 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
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with 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
- C07D233/90—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
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic 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; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/88—Compounds with a double bond between positions 2 and 3 and 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
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Ink Jet (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929222700A GB9222700D0 (en) | 1992-10-29 | 1992-10-29 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI9300574A true SI9300574A (en) | 1994-06-30 |
Family
ID=10724235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9300574A SI9300574A (en) | 1992-10-29 | 1993-10-29 | 6-(substituted-methylene)penems with pharmaceutical properties |
Country Status (35)
| Country | Link |
|---|---|
| US (3) | US5602250A (ko) |
| EP (1) | EP0666862B1 (ko) |
| JP (1) | JP3488457B2 (ko) |
| KR (1) | KR100295710B1 (ko) |
| CN (3) | CN1044247C (ko) |
| AP (1) | AP438A (ko) |
| AT (1) | ATE191914T1 (ko) |
| AU (1) | AU687365B2 (ko) |
| BR (1) | BR1100542A (ko) |
| CA (1) | CA2147755C (ko) |
| CZ (1) | CZ293106B6 (ko) |
| DE (1) | DE69328436T2 (ko) |
| DK (1) | DK0666862T3 (ko) |
| ES (1) | ES2145064T3 (ko) |
| FI (1) | FI114638B (ko) |
| GB (1) | GB9222700D0 (ko) |
| GR (1) | GR3033448T3 (ko) |
| HK (1) | HK1012375A1 (ko) |
| HU (1) | HUT71467A (ko) |
| IL (1) | IL107431A (ko) |
| MA (1) | MA23017A1 (ko) |
| MX (1) | MX9306679A (ko) |
| MY (1) | MY117265A (ko) |
| NO (1) | NO306903B1 (ko) |
| NZ (1) | NZ257109A (ko) |
| PH (1) | PH30919A (ko) |
| PL (1) | PL177840B1 (ko) |
| PT (1) | PT666862E (ko) |
| RU (1) | RU2133750C1 (ko) |
| SA (1) | SA93140373B1 (ko) |
| SI (1) | SI9300574A (ko) |
| SK (1) | SK281870B6 (ko) |
| TW (1) | TW400332B (ko) |
| WO (1) | WO1994010178A1 (ko) |
| ZA (1) | ZA937993B (ko) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9222700D0 (en) * | 1992-10-29 | 1992-12-09 | Smithkline Beecham Plc | Chemical compounds |
| GB9326248D0 (en) * | 1993-12-23 | 1994-02-23 | Smithkline Beecham Plc | Pharmaceutical formulations |
| US6472383B1 (en) | 1994-04-25 | 2002-10-29 | Smithkline Beecham P.L.C. | Pharmaceutical formulations |
| WO1995028935A1 (en) * | 1994-04-25 | 1995-11-02 | Smithkline Beecham Plc | Pharmaceutical formulations containing a beta-lactamase inhibiting penem in combination with a beta-lactam antibiotic and their use in the treatment of bacterial infections |
| US6969303B1 (en) * | 1994-10-12 | 2005-11-29 | Nextec, Inc. | Method and composition for removing coatings which contain hazardous elements |
| WO2002028868A1 (fr) * | 2000-10-03 | 2002-04-11 | Elena Alexandrovna Izakson | Derives de thiazine |
| ES2316599T3 (es) | 2001-09-14 | 2009-04-16 | Glaxo Group Limited | Derivados de fenetanolamina para el tratamiento de enfermedades respiratorias. |
| AR039476A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | Proceso para preparar derivados de 6-alquiliden penem |
| AR039774A1 (es) * | 2002-05-01 | 2005-03-02 | Wyeth Corp | 6-alquiliden-penems biciclicos como inhibidores de beta-lactamasas |
| AR039475A1 (es) | 2002-05-01 | 2005-02-23 | Wyeth Corp | 6-alquiliden-penems triciclicos como inhibidores de beta-lactamasa |
| FR2844807B1 (fr) * | 2002-09-23 | 2005-11-11 | Rambach Alain | Procede de detection de microorganismes resistants a la meticilline |
| AU2004240924A1 (en) | 2003-05-16 | 2004-12-02 | Wyeth Holdings Corporation | Process for synthesizing beta-lactamase inhibitor intermediates |
| TW200716102A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Bicyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
| US8722884B2 (en) * | 2005-12-01 | 2014-05-13 | Verastem, Inc. | Pyrimidine derivatives for the treatment of abnormal cell growth |
| EP2316821A1 (en) * | 2009-10-27 | 2011-05-04 | Novartis AG | Process for the manufacture of organic compounds |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2541924A (en) * | 1948-09-17 | 1951-02-13 | Lilly Co Eli | Synthesis of substituted imidazoles |
| GB1403841A (en) * | 1973-03-22 | 1975-08-28 | Ici Ltd | Imidazo heterocyclic derivatives |
| US4137320A (en) * | 1974-02-07 | 1979-01-30 | Plantex, Ltd. | Pharmaceutical compositions containing imidazo(2,1-b)thiazoles and process for reducing blood sugar levels therewith |
| DE2949167A1 (de) * | 1978-12-08 | 1980-06-26 | Ciba Geigy Ag | Photographisches material fuer das silberfarbbleichverfahren |
| FI82471C (fi) * | 1984-01-26 | 1991-03-11 | Beecham Group Plc | Foerfarande foer framstaellning av farmakologiskt aktiva 6-metylenpenemderivater. |
| US5015473A (en) * | 1984-01-30 | 1991-05-14 | Pfizer Inc. | 6-(substituted)methylenepenicillanic and 6-(substituted)hydroxymethylpenicillanic acids and derivatives thereof |
| GB8518421D0 (en) * | 1985-07-22 | 1985-08-29 | Beecham Group Plc | Compounds |
| GB8518416D0 (en) * | 1985-07-22 | 1985-08-29 | Beecham Group Plc | Compounds |
| GB9222700D0 (en) * | 1992-10-29 | 1992-12-09 | Smithkline Beecham Plc | Chemical compounds |
| JP2000500443A (ja) | 1995-11-08 | 2000-01-18 | スミスクライン・ビーチャム・コーポレイション | ３−フェニル−１−メチレンジオキシフェニル−インダン−２−カルボン酸誘導体の製造プロセス |
-
1992
- 1992-10-29 GB GB929222700A patent/GB9222700D0/en active Pending
-
1993
- 1993-10-15 PH PH47096A patent/PH30919A/en unknown
- 1993-10-20 SK SK540-95A patent/SK281870B6/sk not_active IP Right Cessation
- 1993-10-20 EP EP93923504A patent/EP0666862B1/en not_active Expired - Lifetime
- 1993-10-20 WO PCT/EP1993/002894 patent/WO1994010178A1/en active IP Right Grant
- 1993-10-20 NZ NZ257109A patent/NZ257109A/en not_active IP Right Cessation
- 1993-10-20 PT PT93923504T patent/PT666862E/pt unknown
- 1993-10-20 ES ES93923504T patent/ES2145064T3/es not_active Expired - Lifetime
- 1993-10-20 AU AU53355/94A patent/AU687365B2/en not_active Ceased
- 1993-10-20 RU RU95110049A patent/RU2133750C1/ru active
- 1993-10-20 CA CA002147755A patent/CA2147755C/en not_active Expired - Fee Related
- 1993-10-20 CZ CZ19951053A patent/CZ293106B6/cs not_active IP Right Cessation
- 1993-10-20 JP JP51063794A patent/JP3488457B2/ja not_active Expired - Fee Related
- 1993-10-20 DK DK93923504T patent/DK0666862T3/da active
- 1993-10-20 KR KR1019950701652A patent/KR100295710B1/ko not_active IP Right Cessation
- 1993-10-20 US US08/428,101 patent/US5602250A/en not_active Expired - Lifetime
- 1993-10-20 AT AT93923504T patent/ATE191914T1/de not_active IP Right Cessation
- 1993-10-20 DE DE69328436T patent/DE69328436T2/de not_active Expired - Fee Related
- 1993-10-20 PL PL93308643A patent/PL177840B1/pl not_active IP Right Cessation
- 1993-10-20 HU HU9501226A patent/HUT71467A/hu unknown
- 1993-10-27 MX MX9306679A patent/MX9306679A/es not_active IP Right Cessation
- 1993-10-27 MY MYPI93002250A patent/MY117265A/en unknown
- 1993-10-27 MA MA23323A patent/MA23017A1/fr unknown
- 1993-10-27 ZA ZA937993A patent/ZA937993B/xx unknown
- 1993-10-28 CN CN93119574A patent/CN1044247C/zh not_active Expired - Fee Related
- 1993-10-28 AP APAP/P/1993/000585A patent/AP438A/en active
- 1993-10-28 IL IL10743193A patent/IL107431A/en not_active IP Right Cessation
- 1993-10-29 SI SI9300574A patent/SI9300574A/sl unknown
- 1993-10-30 TW TW082109081A patent/TW400332B/zh not_active IP Right Cessation
- 1993-11-27 SA SA93140373A patent/SA93140373B1/ar unknown
-
1995
- 1995-04-28 NO NO951634A patent/NO306903B1/no not_active IP Right Cessation
- 1995-04-28 FI FI952063A patent/FI114638B/fi active IP Right Grant
- 1995-05-24 US US08/448,941 patent/US6600035B1/en not_active Expired - Fee Related
- 1995-05-24 US US08/448,730 patent/US6037469A/en not_active Expired - Fee Related
-
1997
- 1997-05-13 BR BR1100542-4A patent/BR1100542A/pt active IP Right Grant
-
1998
- 1998-08-11 CN CN98118447A patent/CN1102595C/zh not_active Expired - Fee Related
- 1998-08-11 CN CNB001068075A patent/CN1143851C/zh not_active Expired - Fee Related
- 1998-12-16 HK HK98113576A patent/HK1012375A1/xx not_active IP Right Cessation
-
2000
- 2000-05-19 GR GR20000401136T patent/GR3033448T3/el not_active IP Right Cessation
Also Published As
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