OA12232A - Pharmaceutical compositions of glycogen phosporylase inhibitors. - Google Patents

Pharmaceutical compositions of glycogen phosporylase inhibitors. Download PDF

Info

Publication number: OA12232A
Authority: OA; OAPI
Prior art keywords: alkyl; composition; hydroxy; strand; mono
Prior art date: 2000-03-16

Application number

OA1200200290A

Other languages

English (en)

Inventor

Dwayne Thomas Friesen

Dennis Jay Hoover

Douglas Alan Lorenz

James Alan Schrive Nightingale

Ravi Mysore Shanker

Original Assignee

Pfizer Prod Inc

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

2000-03-16

Filing date

2001-03-16

Publication date

2006-05-10

2001-03-16 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2006-05-10 Publication of OA12232A publication Critical patent/OA12232A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
229920002527 Glycogen Polymers 0.000 title claims description 5
229940096919 glycogen Drugs 0.000 title claims description 5
239000003112 inhibitor Substances 0.000 title description 17
229920000642 polymer Polymers 0.000 claims abstract description 233
239000000203 mixture Substances 0.000 claims abstract description 232
ROJNYKZWTOHRNU-UHFFFAOYSA-N 2-chloro-4,5-difluoro-n-[[2-methoxy-5-(methylcarbamoylamino)phenyl]carbamoyl]benzamide Chemical compound CNC(=O)NC1=CC=C(OC)C(NC(=O)NC(=O)C=2C(=CC(F)=C(F)C=2)Cl)=C1 ROJNYKZWTOHRNU-UHFFFAOYSA-N 0.000 claims abstract description 223
239000006185 dispersion Substances 0.000 claims abstract description 44
239000006069 physical mixture Substances 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims description 253
-1 n-propyl,hydroxy Chemical group 0.000 claims description 202
125000003545 alkoxy group Chemical group 0.000 claims description 77
239000000243 solution Substances 0.000 claims description 65
125000005843 halogen group Chemical group 0.000 claims description 54
239000002904 solvent Substances 0.000 claims description 50
238000000034 method Methods 0.000 claims description 49
229940081735 acetylcellulose Drugs 0.000 claims description 45
229920002301 cellulose acetate Polymers 0.000 claims description 45
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
150000001875 compounds Chemical class 0.000 claims description 39
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
125000001424 substituent group Chemical group 0.000 claims description 36
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 33
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
125000004093 cyano group Chemical group *C#N 0.000 claims description 28
229910052757 nitrogen Inorganic materials 0.000 claims description 28
FUQOTYRCMBZFOL-UHFFFAOYSA-N 5-chloro-1H-indole-2-carboxylic acid Chemical compound ClC1=CC=C2NC(C(=O)O)=CC2=C1 FUQOTYRCMBZFOL-UHFFFAOYSA-N 0.000 claims description 27
229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 27
229910052799 carbon Inorganic materials 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 27
235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 26
239000001863 hydroxypropyl cellulose Substances 0.000 claims description 25
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 24
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
238000000338 in vitro Methods 0.000 claims description 23
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 23
229920002678 cellulose Polymers 0.000 claims description 22
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 claims description 21
125000003282 alkyl amino group Chemical group 0.000 claims description 21
235000010980 cellulose Nutrition 0.000 claims description 21
239000001913 cellulose Substances 0.000 claims description 21
239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 21
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
229940081734 cellulose acetate phthalate Drugs 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 18
229920000609 methyl cellulose Polymers 0.000 claims description 18
235000010981 methylcellulose Nutrition 0.000 claims description 18
239000001923 methylcellulose Substances 0.000 claims description 18
206010053317 Hydrophobia Diseases 0.000 claims description 16
102000004877 Insulin Human genes 0.000 claims description 16
108090001061 Insulin Proteins 0.000 claims description 16
229940125396 insulin Drugs 0.000 claims description 16
238000001694 spray drying Methods 0.000 claims description 16
229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 15
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 15
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
239000000651 prodrug Substances 0.000 claims description 15
229940002612 prodrug Drugs 0.000 claims description 15
229960002900 methylcellulose Drugs 0.000 claims description 14
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 14
102000007390 Glycogen Phosphorylase Human genes 0.000 claims description 13
108010046163 Glycogen Phosphorylase Proteins 0.000 claims description 13
125000001475 halogen functional group Chemical group 0.000 claims description 13
125000000623 heterocyclic group Chemical group 0.000 claims description 13
238000001727 in vivo Methods 0.000 claims description 13
239000007787 solid Substances 0.000 claims description 13
102000004190 Enzymes Human genes 0.000 claims description 12
108090000790 Enzymes Proteins 0.000 claims description 12
WZNRVWBKYDHTKI-UHFFFAOYSA-N cellulose, acetate 1,2,4-benzenetricarboxylate Chemical compound OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O.OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O.CC(=O)OCC1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(COC(C)=O)O1.CC(=O)OCC1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(COC(C)=O)O1.OC(=O)C1=CC(C(=O)O)=CC=C1C(=O)OCC1C(OC2C(C(OC(=O)C=3C(=CC(=CC=3)C(O)=O)C(O)=O)C(OC(=O)C=3C(=CC(=CC=3)C(O)=O)C(O)=O)C(COC(=O)C=3C(=CC(=CC=3)C(O)=O)C(O)=O)O2)OC(=O)C=2C(=CC(=CC=2)C(O)=O)C(O)=O)C(OC(=O)C=2C(=CC(=CC=2)C(O)=O)C(O)=O)C(OC(=O)C=2C(=CC(=CC=2)C(O)=O)C(O)=O)C(OC(=O)C=2C(=CC(=CC=2)C(O)=O)C(O)=O)O1 WZNRVWBKYDHTKI-UHFFFAOYSA-N 0.000 claims description 12
125000002541 furyl group Chemical group 0.000 claims description 12
125000001153 fluoro group Chemical group F* 0.000 claims description 11
125000005591 trimellitate group Chemical group 0.000 claims description 11
ZAMLGGRVTAXBHI-UHFFFAOYSA-N 3-(4-bromophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(CC(O)=O)C1=CC=C(Br)C=C1 ZAMLGGRVTAXBHI-UHFFFAOYSA-N 0.000 claims description 10
206010020772 Hypertension Diseases 0.000 claims description 10
GAMPNQJDUFQVQO-UHFFFAOYSA-N acetic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O GAMPNQJDUFQVQO-UHFFFAOYSA-N 0.000 claims description 10
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 10
125000002883 imidazolyl group Chemical group 0.000 claims description 10
125000003226 pyrazolyl group Chemical group 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 9
208000002177 Cataract Diseases 0.000 claims description 9
239000001856 Ethyl cellulose Substances 0.000 claims description 9
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 9
208000035150 Hypercholesterolemia Diseases 0.000 claims description 9
IYKJEILNJZQJPU-UHFFFAOYSA-N acetic acid;butanedioic acid Chemical compound CC(O)=O.OC(=O)CCC(O)=O IYKJEILNJZQJPU-UHFFFAOYSA-N 0.000 claims description 9
239000007864 aqueous solution Substances 0.000 claims description 9
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
235000019325 ethyl cellulose Nutrition 0.000 claims description 9
229920001249 ethyl cellulose Polymers 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
125000004076 pyridyl group Chemical group 0.000 claims description 9
125000000168 pyrrolyl group Chemical group 0.000 claims description 9
208000031226 Hyperlipidaemia Diseases 0.000 claims description 8
125000000676 alkoxyimino group Chemical group 0.000 claims description 8
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 claims description 8
201000001421 hyperglycemia Diseases 0.000 claims description 8
125000001786 isothiazolyl group Chemical group 0.000 claims description 8
125000000842 isoxazolyl group Chemical group 0.000 claims description 8
125000002757 morpholinyl group Chemical group 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 8
125000002098 pyridazinyl group Chemical group 0.000 claims description 8
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
208000007342 Diabetic Nephropathies Diseases 0.000 claims description 7
208000032131 Diabetic Neuropathies Diseases 0.000 claims description 7
206010012689 Diabetic retinopathy Diseases 0.000 claims description 7
241000282414 Homo sapiens Species 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
229920001577 copolymer Polymers 0.000 claims description 7
208000033679 diabetic kidney disease Diseases 0.000 claims description 7
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
238000012545 processing Methods 0.000 claims description 7
125000000335 thiazolyl group Chemical group 0.000 claims description 7
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical compound CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
229920001727 cellulose butyrate Polymers 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
125000002971 oxazolyl group Chemical group 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000003386 piperidinyl group Chemical group 0.000 claims description 6
125000003373 pyrazinyl group Chemical group 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 5
229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims description 5
241001465754 Metazoa Species 0.000 claims description 5
PLEULVPCZZDBNB-UHFFFAOYSA-N acetic acid;butanedioic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)CCC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O PLEULVPCZZDBNB-UHFFFAOYSA-N 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
229920006218 cellulose propionate Polymers 0.000 claims description 5
235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 5
QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000004043 oxo group Chemical group O=* 0.000 claims description 5
229920002554 vinyl polymer Polymers 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims description 4
VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 claims description 4
DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 claims description 4
229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 4
CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
208000031225 myocardial ischemia Diseases 0.000 claims description 4
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 4
125000002755 pyrazolinyl group Chemical group 0.000 claims description 4
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims description 3
ZNNQGSGPVUYWOS-UHFFFAOYSA-N 2-(3-hydroxypropoxy)benzoic acid Chemical compound OCCCOC1=CC=CC=C1C(O)=O ZNNQGSGPVUYWOS-UHFFFAOYSA-N 0.000 claims description 3
NMGBFVPQUCLJGM-UHFFFAOYSA-N 3-ethylphthalic acid Chemical compound CCC1=CC=CC(C(O)=O)=C1C(O)=O NMGBFVPQUCLJGM-UHFFFAOYSA-N 0.000 claims description 3
INTNEELQXPKMNM-UHFFFAOYSA-N 3-ethylpyridine-2-carboxylic acid Chemical compound CCC1=CC=CN=C1C(O)=O INTNEELQXPKMNM-UHFFFAOYSA-N 0.000 claims description 3
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
GZRANGIRVYGSDJ-UHFFFAOYSA-N acetic acid;pyridine-2,3-dicarboxylic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CN=C1C(O)=O GZRANGIRVYGSDJ-UHFFFAOYSA-N 0.000 claims description 3
FMTQGBMMIVVKSN-UHFFFAOYSA-N acetic acid;terephthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=C(C(O)=O)C=C1 FMTQGBMMIVVKSN-UHFFFAOYSA-N 0.000 claims description 3
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
239000001768 carboxy methyl cellulose Substances 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
230000002441 reversible effect Effects 0.000 claims description 3
125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 claims description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 2
208000035143 Bacterial infection Diseases 0.000 claims description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
208000032781 Diabetic cardiomyopathy Diseases 0.000 claims description 2
XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
208000022362 bacterial infectious disease Diseases 0.000 claims description 2
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
230000002708 enhancing effect Effects 0.000 claims description 2
210000001035 gastrointestinal tract Anatomy 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims description 2
229940081066 picolinic acid Drugs 0.000 claims description 2
125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
230000004614 tumor growth Effects 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
229940122294 Phosphorylase inhibitor Drugs 0.000 claims 19
SOGNHUJSAKAIRG-UHFFFAOYSA-N 2-chloro-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound C1=C(Cl)SC2=C1C=C(C(=O)O)N2 SOGNHUJSAKAIRG-UHFFFAOYSA-N 0.000 claims 4
ZUAAPNNKRHMPKG-UHFFFAOYSA-N acetic acid;butanedioic acid;methanol;propane-1,2-diol Chemical compound OC.CC(O)=O.CC(O)CO.OC(=O)CCC(O)=O ZUAAPNNKRHMPKG-UHFFFAOYSA-N 0.000 claims 3
125000006529 (C3-C6) alkyl group Chemical group 0.000 claims 1
125000005987 1-oxo-thiomorpholinyl group Chemical group 0.000 claims 1
ZEDBZFFACLMUCO-UHFFFAOYSA-N 2-amino-1-(1-oxo-1,3-thiazolidin-3-yl)ethanone Chemical compound NCC(=O)N1CCS(=O)C1 ZEDBZFFACLMUCO-UHFFFAOYSA-N 0.000 claims 1
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
VFFMCGXIWQUAEL-UHFFFAOYSA-N 5-acetyl-1-ethyl-2-oxo-n-[3-(phenylcarbamoyl)phenyl]-3h-indole-3-carboxamide Chemical compound C12=CC(C(C)=O)=CC=C2N(CC)C(=O)C1C(=O)NC(C=1)=CC=CC=1C(=O)NC1=CC=CC=C1 VFFMCGXIWQUAEL-UHFFFAOYSA-N 0.000 claims 1
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- 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
- A61K31/403—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 carbocyclic rings, e.g. carbazole
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OA1200200290A 2000-03-16 2001-03-16 Pharmaceutical compositions of glycogen phosporylase inhibitors. OA12232A (en)

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US18994200P	2000-03-16	2000-03-16

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OA12232A true OA12232A (en)	2006-05-10

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EP (1)	EP1263414A1 (is)
JP (1)	JP2003526654A (is)
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MA (1)	MA26882A1 (is)
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SV (1)	SV2002000343A (is)
TN (1)	TNSN01040A1 (is)
TR (1)	TR200202184T2 (is)
WO (1)	WO2001068055A1 (is)
YU (1)	YU67202A (is)
ZA (1)	ZA200207290B (is)

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2001
- 2001-03-14 PE PE2001000246A patent/PE20011184A1/es not_active Application Discontinuation
- 2001-03-14 US US09/805,828 patent/US20010053778A1/en not_active Abandoned
- 2001-03-14 AR ARP010101185A patent/AR027656A1/es not_active Application Discontinuation
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- 2001-03-16 TR TR2002/02184T patent/TR200202184T2/xx unknown
- 2001-03-16 JP JP2001566619A patent/JP2003526654A/ja active Pending
- 2001-03-16 EP EP01915586A patent/EP1263414A1/en not_active Withdrawn
- 2001-03-16 MX MXPA02009097A patent/MXPA02009097A/es unknown
- 2001-03-16 CN CN01806619A patent/CN1418089A/zh active Pending
- 2001-03-16 WO PCT/IB2001/000394 patent/WO2001068055A1/en not_active Ceased
- 2001-03-16 CA CA002403241A patent/CA2403241A1/en not_active Abandoned
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- 2001-03-16 PL PL36078001A patent/PL360780A1/xx not_active Application Discontinuation
- 2001-03-16 BR BR0109189-1A patent/BR0109189A/pt not_active Application Discontinuation
- 2001-03-16 CO CO01021769A patent/CO5280087A1/es not_active Application Discontinuation
- 2001-03-16 AU AU2001242669A patent/AU2001242669A1/en not_active Abandoned
- 2001-03-16 CZ CZ20022955A patent/CZ20022955A3/cs unknown
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- 2001-03-16 PA PA20018513601A patent/PA8513601A1/es unknown
- 2001-03-16 SK SK1262-2002A patent/SK12622002A3/sk unknown
- 2001-03-16 KR KR1020027012009A patent/KR20020081445A/ko not_active Ceased
- 2001-03-16 IL IL15132001A patent/IL151320A0/xx unknown
- 2001-03-16 EE EEP200200530A patent/EE200200530A/xx unknown
2002
- 2002-08-16 IS IS6508A patent/IS6508A/is unknown
- 2002-08-26 BG BG107037A patent/BG107037A/bg unknown
- 2002-09-11 MA MA26810A patent/MA26882A1/fr unknown
- 2002-09-11 ZA ZA200207290A patent/ZA200207290B/xx unknown
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Also Published As

Publication number	Publication date
BG107037A (bg)	2003-04-30
EE200200530A (et)	2004-04-15
US20010053778A1 (en)	2001-12-20
IS6508A (is)	2002-08-16
CA2403241A1 (en)	2001-09-20
HUP0204583A2 (hu)	2003-04-28
EA200200858A1 (ru)	2003-02-27
PE20011184A1 (es)	2001-11-15
PA8513601A1 (es)	2004-08-31
YU67202A (sh)	2006-01-16
TR200202184T2 (tr)	2003-01-21
PL360780A1 (en)	2004-09-20
CN1418089A (zh)	2003-05-14
NO20024386L (no)	2002-11-13
AU2001242669A1 (en)	2001-09-24
CZ20022955A3 (cs)	2003-09-17
MXPA02009097A (es)	2003-03-12
AP2002002621A0 (en)	2002-09-30
AR027656A1 (es)	2003-04-09
WO2001068055A1 (en)	2001-09-20
SK12622002A3 (sk)	2004-02-03
EP1263414A1 (en)	2002-12-11
TNSN01040A1 (fr)	2005-11-10
JP2003526654A (ja)	2003-09-09
NO20024386D0 (no)	2002-09-13
IL151320A0 (en)	2003-04-10
KR20020081445A (ko)	2002-10-26
CO5280087A1 (es)	2003-05-30
SV2002000343A (es)	2002-07-03
MA26882A1 (fr)	2004-12-20
ZA200207290B (en)	2003-09-11
BR0109189A (pt)	2003-05-27

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