CA2216809A1 - Imidazo[1,2-a]pyridine derivatives - Google Patents

Imidazo[1,2-a]pyridine derivatives Download PDF

Info

Publication number: CA2216809A1
Authority: CA; Canada
Prior art keywords: formula; compounds; compound; 4alkyl; methyl
Prior art date: 1995-04-04
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA002216809A

Other languages

English (en)

French (fr)

Inventor

Alan Naylor

Ian Baxter Campbell

Paul John Beswick

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Glaxo Group Ltd

Original Assignee

Individual

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.)

1995-04-04

Filing date

1996-04-02

Publication date

1996-10-10

1995-04-04 Priority claimed from GBGB9506965.4A external-priority patent/GB9506965D0/en

1995-06-14 Priority claimed from GBGB9512099.4A external-priority patent/GB9512099D0/en

1995-08-05 Priority claimed from GBGB9516117.0A external-priority patent/GB9516117D0/en

1996-04-02 Application filed by Individual filed Critical Individual

1996-10-10 Publication of CA2216809A1 publication Critical patent/CA2216809A1/en

Status Abandoned legal-status Critical Current

Links

150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 139
238000011282 treatment Methods 0.000 claims abstract description 21
102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims abstract description 19
108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 claims abstract description 18
229910052799 carbon Inorganic materials 0.000 claims abstract description 11
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 15
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
229910052794 bromium Inorganic materials 0.000 claims description 25
238000000034 method Methods 0.000 claims description 23
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
229910052801 chlorine Inorganic materials 0.000 claims description 18
239000000460 chlorine Substances 0.000 claims description 18
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 13
239000011737 fluorine Substances 0.000 claims description 13
239000003814 drug Substances 0.000 claims description 12
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 11
VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
-1 methyl) Chemical group 0.000 claims description 9
230000008569 process Effects 0.000 claims description 8
230000005764 inhibitory process Effects 0.000 claims description 7
229940124597 therapeutic agent Drugs 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 4
208000027866 inflammatory disease Diseases 0.000 claims description 4
230000001404 mediated effect Effects 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
KVVJDDVNYVCFDS-UHFFFAOYSA-N 1-[3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridin-8-yl]ethanone Chemical compound N1=C2C(C(=O)C)=CC=CN2C(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 KVVJDDVNYVCFDS-UHFFFAOYSA-N 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
150000003840 hydrochlorides Chemical class 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical class [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
229910021653 sulphate ion Chemical class 0.000 claims 1
201000010099 disease Diseases 0.000 abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
229940124639 Selective inhibitor Drugs 0.000 abstract description 4
230000003389 potentiating effect Effects 0.000 abstract description 3
206010061218 Inflammation Diseases 0.000 abstract description 2
208000002193 Pain Diseases 0.000 abstract description 2
206010037660 Pyrexia Diseases 0.000 abstract description 2
230000004054 inflammatory process Effects 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 61
239000000243 solution Substances 0.000 description 51
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 29
239000000377 silicon dioxide Substances 0.000 description 29
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
239000007787 solid Substances 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
125000000217 alkyl group Chemical group 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
229910052681 coesite Inorganic materials 0.000 description 11
229910052906 cristobalite Inorganic materials 0.000 description 11
238000003818 flash chromatography Methods 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
235000012239 silicon dioxide Nutrition 0.000 description 11
229910052682 stishovite Inorganic materials 0.000 description 11
229910052905 tridymite Inorganic materials 0.000 description 11
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
238000001514 detection method Methods 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
239000002253 acid Substances 0.000 description 9
239000012286 potassium permanganate Substances 0.000 description 9
108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 8
102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000002904 solvent Substances 0.000 description 8
MWSPVZXQINZJFP-UHFFFAOYSA-N 2-bromo-2-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)ethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)C(Br)C1=CC=C(F)C=C1 MWSPVZXQINZJFP-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
238000011534 incubation Methods 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
239000002609 medium Substances 0.000 description 6
239000001267 polyvinylpyrrolidone Substances 0.000 description 6
229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
239000000725 suspension Substances 0.000 description 6
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 5
229960000583 acetic acid Drugs 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000008101 lactose Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical class C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
229960004132 diethyl ether Drugs 0.000 description 4
238000009472 formulation Methods 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000003826 tablet Substances 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
206010012289 Dementia Diseases 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
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 3
239000007832 Na2SO4 Substances 0.000 description 3
241000282320 Panthera leo Species 0.000 description 3
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 3
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
244000309464 bull Species 0.000 description 3
238000004113 cell culture Methods 0.000 description 3
239000006071 cream Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000002768 hydroxyalkyl group Chemical group 0.000 description 3
208000014674 injury Diseases 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
239000002953 phosphate buffered saline Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000012453 solvate Substances 0.000 description 3
NXPJZQYAGOYGTO-UHFFFAOYSA-N 1,2-bis(4-fluorophenyl)ethanone Chemical compound C1=CC(F)=CC=C1CC(=O)C1=CC=C(F)C=C1 NXPJZQYAGOYGTO-UHFFFAOYSA-N 0.000 description 2
CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 2
208000024827 Alzheimer disease Diseases 0.000 description 2
206010010904 Convulsion Diseases 0.000 description 2
102000004127 Cytokines Human genes 0.000 description 2
108090000695 Cytokines Proteins 0.000 description 2
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 2
201000004624 Dermatitis Diseases 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
101000605122 Homo sapiens Prostaglandin G/H synthase 1 Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
229920000168 Microcrystalline cellulose Polymers 0.000 description 2
229920000881 Modified starch Polymers 0.000 description 2
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 2
102000008299 Nitric Oxide Synthase Human genes 0.000 description 2
108010021487 Nitric Oxide Synthase Proteins 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
102000004142 Trypsin Human genes 0.000 description 2
108090000631 Trypsin Proteins 0.000 description 2
201000004810 Vascular dementia Diseases 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
HUCJFAOMUPXHDK-UHFFFAOYSA-N Xylometazoline Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1CC1=NCCN1 HUCJFAOMUPXHDK-UHFFFAOYSA-N 0.000 description 2
FRRYJNHCBPBFKC-UHFFFAOYSA-N [3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridin-8-yl]methanol Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N2C=CC=C(CO)C2=N1 FRRYJNHCBPBFKC-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000008364 bulk solution Substances 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
208000010877 cognitive disease Diseases 0.000 description 2
238000007906 compression Methods 0.000 description 2
230000006835 compression Effects 0.000 description 2
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
230000006378 damage Effects 0.000 description 2
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 2
229960002986 dinoprostone Drugs 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000019634 flavors Nutrition 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000003102 growth factor Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
239000005556 hormone Substances 0.000 description 2
102000053332 human PTGS1 Human genes 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
229940016286 microcrystalline cellulose Drugs 0.000 description 2
235000019813 microcrystalline cellulose Nutrition 0.000 description 2
239000008108 microcrystalline cellulose Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
230000001537 neural effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
201000008482 osteoarthritis Diseases 0.000 description 2
WYWIFABBXFUGLM-UHFFFAOYSA-N oxymetazoline Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1 WYWIFABBXFUGLM-UHFFFAOYSA-N 0.000 description 2
229940094443 oxytocics prostaglandins Drugs 0.000 description 2
230000001575 pathological effect Effects 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 2
150000003180 prostaglandins Chemical class 0.000 description 2
230000009467 reduction Effects 0.000 description 2
230000001624 sedative effect Effects 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000012588 trypsin Substances 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
WRRSFOZOETZUPG-FFHNEAJVSA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;hydrate Chemical compound O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC WRRSFOZOETZUPG-FFHNEAJVSA-N 0.000 description 1
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
229930182837 (R)-adrenaline Natural products 0.000 description 1
CFJMRBQWBDQYMK-UHFFFAOYSA-N 1-phenyl-1-cyclopentanecarboxylic acid 2-[2-(diethylamino)ethoxy]ethyl ester Chemical compound C=1C=CC=CC=1C1(C(=O)OCCOCCN(CC)CC)CCCC1 CFJMRBQWBDQYMK-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
AEJJCZKQIDVMBE-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)ethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)CC1=CC=C(F)C=C1 AEJJCZKQIDVMBE-UHFFFAOYSA-N 0.000 description 1
AZVBUXADPFKFPH-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N2C=CC=CC2=N1 AZVBUXADPFKFPH-UHFFFAOYSA-N 0.000 description 1
FMIAWMTWGFMXDB-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine-8-carbaldehyde Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N2C=CC=C(C=O)C2=N1 FMIAWMTWGFMXDB-UHFFFAOYSA-N 0.000 description 1
KDSWLPVULUCPSK-UHFFFAOYSA-N 3-(4-fluorophenyl)-7,8-dimethyl-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound N1=C2C(C)=C(C)C=CN2C(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 KDSWLPVULUCPSK-UHFFFAOYSA-N 0.000 description 1
DPJUCZCNHAEIFB-UHFFFAOYSA-N 3-(4-fluorophenyl)-8-methyl-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound N1=C2C(C)=CC=CN2C(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 DPJUCZCNHAEIFB-UHFFFAOYSA-N 0.000 description 1
YWOWJQMFMXHLQD-UHFFFAOYSA-N 3-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=NC=CC=C1C(F)(F)F YWOWJQMFMXHLQD-UHFFFAOYSA-N 0.000 description 1
RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 description 1
FODHGTMFSOOZEY-UHFFFAOYSA-N 3-methylsulfanylpyridin-2-amine Chemical compound CSC1=CC=CN=C1N FODHGTMFSOOZEY-UHFFFAOYSA-N 0.000 description 1
JTMWTMXGLQZPKU-UHFFFAOYSA-N 4-bromo-2-methyl-2h-pyridin-1-amine Chemical compound CC1C=C(Br)C=CN1N JTMWTMXGLQZPKU-UHFFFAOYSA-N 0.000 description 1
ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 1
LUMNWCHHXDUKFI-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethanol Chemical compound C1C2C(CO)CC1C=C2 LUMNWCHHXDUKFI-UHFFFAOYSA-N 0.000 description 1
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
DKTCASRYGFMCRO-UHFFFAOYSA-N 8-(fluoromethyl)-3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N2C=CC=C(CF)C2=N1 DKTCASRYGFMCRO-UHFFFAOYSA-N 0.000 description 1
QPVMPKSUPTWTTL-UHFFFAOYSA-N 8-bromo-3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N2C=CC=C(Br)C2=N1 QPVMPKSUPTWTTL-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
206010002660 Anoxia Diseases 0.000 description 1
241000976983 Anoxia Species 0.000 description 1
208000032467 Aplastic anaemia Diseases 0.000 description 1
208000025978 Athletic injury Diseases 0.000 description 1
208000000412 Avitaminosis Diseases 0.000 description 1
208000027496 Behcet disease Diseases 0.000 description 1
206010006811 Bursitis Diseases 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
208000020406 Creutzfeldt Jacob disease Diseases 0.000 description 1
208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 description 1
208000010859 Creutzfeldt-Jakob disease Diseases 0.000 description 1
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 1
206010013935 Dysmenorrhoea Diseases 0.000 description 1
NXEZCZIUCZFUOY-UHFFFAOYSA-N FC1=CC=C(C=C1)C1=C(N=C2N1C=CC=C2C(F)(F)F)C2=CC=C(C=C2)S(=O)(=O)C Chemical compound FC1=CC=C(C=C1)C1=C(N=C2N1C=CC=C2C(F)(F)F)C2=CC=C(C=C2)S(=O)(=O)C NXEZCZIUCZFUOY-UHFFFAOYSA-N 0.000 description 1
201000011240 Frontotemporal dementia Diseases 0.000 description 1
208000007882 Gastritis Diseases 0.000 description 1
201000005569 Gout Diseases 0.000 description 1
208000034308 Grand mal convulsion Diseases 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
208000017604 Hodgkin disease Diseases 0.000 description 1
208000010747 Hodgkins lymphoma Diseases 0.000 description 1
101000605127 Homo sapiens Prostaglandin G/H synthase 2 Proteins 0.000 description 1
208000023105 Huntington disease Diseases 0.000 description 1
206010021135 Hypovitaminosis Diseases 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
208000022559 Inflammatory bowel disease Diseases 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
208000008930 Low Back Pain Diseases 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
208000005314 Multi-Infarct Dementia Diseases 0.000 description 1
208000036572 Myoclonic epilepsy Diseases 0.000 description 1
201000002481 Myositis Diseases 0.000 description 1
206010028836 Neck pain Diseases 0.000 description 1
206010029164 Nephrotic syndrome Diseases 0.000 description 1
102100022397 Nitric oxide synthase, brain Human genes 0.000 description 1
101710111444 Nitric oxide synthase, brain Proteins 0.000 description 1
102100029438 Nitric oxide synthase, inducible Human genes 0.000 description 1
101710089543 Nitric oxide synthase, inducible Proteins 0.000 description 1
239000012425 OXONE® Substances 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
206010061334 Partial seizures Diseases 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
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 1
206010034759 Petit mal epilepsy Diseases 0.000 description 1
208000000609 Pick Disease of the Brain Diseases 0.000 description 1
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
241000183024 Populus tremula Species 0.000 description 1
206010036600 Premature labour Diseases 0.000 description 1
108010029485 Protein Isoforms Proteins 0.000 description 1
102000001708 Protein Isoforms Human genes 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
206010038910 Retinitis Diseases 0.000 description 1
206010038923 Retinopathy Diseases 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
206010039085 Rhinitis allergic Diseases 0.000 description 1
206010039966 Senile dementia Diseases 0.000 description 1
208000010040 Sprains and Strains Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000006011 Stroke Diseases 0.000 description 1
208000000491 Tendinopathy Diseases 0.000 description 1
206010043255 Tendonitis Diseases 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
102000018594 Tumour necrosis factor Human genes 0.000 description 1
108050007852 Tumour necrosis factor Proteins 0.000 description 1
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
206010046851 Uveitis Diseases 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000009692 acute damage Effects 0.000 description 1
238000011360 adjunctive therapy Methods 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
201000010105 allergic rhinitis Diseases 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229950011175 aminopicoline Drugs 0.000 description 1
230000000954 anitussive effect Effects 0.000 description 1
230000007953 anoxia Effects 0.000 description 1
229940069428 antacid Drugs 0.000 description 1
239000003159 antacid agent Substances 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000001458 anti-acid effect Effects 0.000 description 1
230000001760 anti-analgesic effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
238000009175 antibody therapy Methods 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
229940124584 antitussives Drugs 0.000 description 1
229940114079 arachidonic acid Drugs 0.000 description 1
235000021342 arachidonic acid Nutrition 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
239000000337 buffer salt Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
244000309466 calf Species 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
229960004126 codeine Drugs 0.000 description 1
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Natural products C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 1
208000029742 colonic neoplasm Diseases 0.000 description 1
239000002299 complementary DNA Substances 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
239000000850 decongestant Substances 0.000 description 1
230000003412 degenerative effect Effects 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 1
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 1
FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 1
AMTWCFIAVKBGOD-UHFFFAOYSA-N dioxosilane;methoxy-dimethyl-trimethylsilyloxysilane Chemical compound O=[Si]=O.CO[Si](C)(C)O[Si](C)(C)C AMTWCFIAVKBGOD-UHFFFAOYSA-N 0.000 description 1
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
201000009028 early myoclonic encephalopathy Diseases 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
229960005139 epinephrine Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000004927 fusion Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
208000007565 gingivitis Diseases 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000002430 glycine receptor antagonist Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 description 1
229960000240 hydrocodone Drugs 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000003018 immunoassay Methods 0.000 description 1
238000002513 implantation Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000007917 intracranial administration Methods 0.000 description 1
239000012336 iodinating agent Substances 0.000 description 1
208000002551 irritable bowel syndrome Diseases 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 1
230000003902 lesion Effects 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
229940121386 matrix metalloproteinase inhibitor Drugs 0.000 description 1
239000003771 matrix metalloproteinase inhibitor Substances 0.000 description 1
206010027175 memory impairment Diseases 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000001394 metastastic effect Effects 0.000 description 1
206010061289 metastatic neoplasm Diseases 0.000 description 1
NZZDEODTCXHCRS-UHFFFAOYSA-N methyl 2-aminopyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1N NZZDEODTCXHCRS-UHFFFAOYSA-N 0.000 description 1
NJAVPXLVHIUTBA-UHFFFAOYSA-N methyl 3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine-8-carboxylate Chemical compound N1=C2C(C(=O)OC)=CC=CN2C(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 NJAVPXLVHIUTBA-UHFFFAOYSA-N 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
208000027061 mild cognitive impairment Diseases 0.000 description 1
239000003226 mitogen Substances 0.000 description 1
238000002625 monoclonal antibody therapy Methods 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
206010028417 myasthenia gravis Diseases 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
OYVXVLSZQHSNDK-UHFFFAOYSA-N n-methoxy-n-methylacetamide Chemical compound CON(C)C(C)=O OYVXVLSZQHSNDK-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960005016 naphazoline Drugs 0.000 description 1
230000001613 neoplastic effect Effects 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000036542 oxidative stress Effects 0.000 description 1
229960001528 oxymetazoline Drugs 0.000 description 1
229940124641 pain reliever Drugs 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
229960003436 pentoxyverine Drugs 0.000 description 1
239000012071 phase Substances 0.000 description 1
229960001802 phenylephrine Drugs 0.000 description 1
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
229960000395 phenylpropanolamine Drugs 0.000 description 1
DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
201000006292 polyarteritis nodosa Diseases 0.000 description 1
208000005987 polymyositis Diseases 0.000 description 1
OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960000786 propylhexedrine Drugs 0.000 description 1
JCRIVQIOJSSCQD-UHFFFAOYSA-N propylhexedrine Chemical compound CNC(C)CC1CCCCC1 JCRIVQIOJSSCQD-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
229960003908 pseudoephedrine Drugs 0.000 description 1
KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
229960000620 ranitidine Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000008327 renal blood flow Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
229940085605 saccharin sodium Drugs 0.000 description 1
238000007789 sealing Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229940083037 simethicone Drugs 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229940126121 sodium channel inhibitor Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
230000003019 stabilising effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
239000003890 substance P antagonist Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
201000004595 synovitis Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
201000004415 tendinitis Diseases 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
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
206010043778 thyroiditis Diseases 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
208000004371 toothache Diseases 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
108700012359 toxins Proteins 0.000 description 1
LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
230000008733 trauma Effects 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
208000030401 vitamin deficiency disease Diseases 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
229960000833 xylometazoline Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

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

CA002216809A 1995-04-04 1996-04-02 Imidazo[1,2-a]pyridine derivatives Abandoned CA2216809A1 (en)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
GBGB9506965.4A GB9506965D0 (en)	1995-04-04	1995-04-04	Chemical compounds
GB9506965.4		1995-04-04
GB9512099.4		1995-06-14
GBGB9512099.4A GB9512099D0 (en)	1995-06-14	1995-06-14	Chemical compounds
GBGB9516117.0A GB9516117D0 (en)	1995-08-05	1995-08-05	Chemical compounds
GB9516117.0		1995-08-05

Publications (1)

Publication Number	Publication Date
CA2216809A1 true CA2216809A1 (en)	1996-10-10

Family

ID=27267657

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002216809A Abandoned CA2216809A1 (en)	1995-04-04	1996-04-02	Imidazo[1,2-a]pyridine derivatives

Country Status (17)

Country	Link
EP (1)	EP0819127A1 (cs)
JP (1)	JPH11501049A (cs)
KR (1)	KR19980703559A (cs)
CN (1)	CN1186492A (cs)
AU (1)	AU5276696A (cs)
BG (1)	BG101934A (cs)
CA (1)	CA2216809A1 (cs)
CZ (1)	CZ313397A3 (cs)
EA (1)	EA199700209A1 (cs)
HU (1)	HUP9801602A3 (cs)
IS (1)	IS4570A (cs)
NO (1)	NO974595L (cs)
NZ (1)	NZ304886A (cs)
PL (1)	PL322623A1 (cs)
SK (1)	SK133297A3 (cs)
TR (1)	TR199701105T1 (cs)
WO (1)	WO1996031509A1 (cs)

Families Citing this family (57)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2764292B1 (fr) *	1997-06-10	2000-12-29	Innothera Lab Sa	Utilisation de derives de tetracycles dicetoniques, nouveaux composes obtenus et leur application en therapeutique
US6307047B1 (en)	1997-08-22	2001-10-23	Abbott Laboratories	Prostaglandin endoperoxide H synthase biosynthesis inhibitors
US6525053B1 (en)	1997-08-22	2003-02-25	Abbott Laboratories	Prostaglandin endoperoxide H synthase biosynthesis inhibitors
ES2203985T3 (es) *	1997-09-05	2004-04-16	Glaxo Group Limited	Derivados de 2,3-diaril-pirazolo(1,5)piridazina, su preparacion y su uso como inhibidores de la ciclooxigenasa 2(cox-2)`.
FR2770131A1 (fr) *	1997-10-27	1999-04-30	Union Pharma Scient Appl	Nouvelle association pharmaceutique a activite analgesique
FR2771005B1 (fr) *	1997-11-18	2002-06-07	Union Pharma Scient Appl	Nouvelle association pharmaceutique a activite analgesique
GB9810920D0 (en) *	1998-05-21	1998-07-22	Merck Sharp & Dohme	Therapeutic use
ES2140354B1 (es) *	1998-08-03	2000-11-01	S A L V A T Lab Sa	Imidazo (1,2a) azinas sustituidas como inhibidores selectivos de la cox-2.
TW587079B (en)	1998-09-25	2004-05-11	Almirall Prodesfarma Ag	2-phenylpyran-4-one derivatives
CN1263755C (zh)	1998-11-03	2006-07-12	葛兰素集团有限公司	作为选择性cox－2抑制剂的吡唑并吡啶衍生物
ATE261444T1 (de) *	1999-02-27	2004-03-15	Glaxo Group Ltd	Pyrazolopyridine
EA008242B1 (ru)	1999-12-08	2007-04-27	Фармация Корпорейшн	Композиции на основе ингибитора циклооксигеназы-2 с быстро наступающим терапевтическим действием и способы лечения заболеваний
GB9930358D0 (en) *	1999-12-22	2000-02-09	Glaxo Group Ltd	Process for the preparation of chemical compounds
US6649629B2 (en)	1999-12-23	2003-11-18	Nitromed, Inc.	Nitrosated and nitrosylated cyclooxygenase-2 inhibitors, compositions and methods of use
GB0002312D0 (en) *	2000-02-01	2000-03-22	Glaxo Group Ltd	Medicaments
PE20011333A1 (es)	2000-03-16	2002-01-16	Almirall Prodesfarma Ag	Derivados de 2-fenilpiran-4-ona como inhibidores de ciclooxigenasa 2
PE20020146A1 (es) *	2000-07-13	2002-03-31	Upjohn Co	Formulacion oftalmica que comprende un inhibidor de ciclooxigenasa-2 (cox-2)
NZ524252A (en)	2000-07-20	2004-03-26	Lauras As	Cox-2 inhibitors for treating HIV and AIDS
PE20020506A1 (es)	2000-08-22	2002-07-09	Glaxo Group Ltd	Derivados de pirazol fusionados como inhibidores de la proteina cinasa
GB0025449D0 (en) *	2000-10-17	2000-11-29	Glaxo Group Ltd	Chemical compounds
WO2002048148A2 (en)	2000-12-15	2002-06-20	Glaxo Group Limited	Pyrazolopyridine derivatives
ATE301653T1 (de)	2000-12-15	2005-08-15	Glaxo Group Ltd	Pyrazolopyridine
DE60201074T2 (de)	2001-03-08	2005-09-15	Smithkline Beecham Corp.	Pyrazolopyridinderivate
EP1372643A1 (en)	2001-03-30	2004-01-02	Smithkline Beecham Corporation	Pyrazolopyridines, process for their preparation and use as therapeutic compounds
PE20021017A1 (es)	2001-04-03	2002-11-24	Pharmacia Corp	Composicion parenteral reconstituible
US7141569B2 (en)	2001-04-10	2006-11-28	Smithkline Beecham Corporation	Antiviral pyrazolopyridine compounds
ES2242028T3 (es)	2001-04-27	2005-11-01	Smithkline Beecham Corporation	Derivados de pirazolo(1,5-a)piridina.
US6756498B2 (en)	2001-04-27	2004-06-29	Smithkline Beecham Corporation	Process for the preparation of chemical compounds
HUP0400266A2 (hu)	2001-06-21	2004-08-30	Smithkline Beecham Corp.	Imidazo[1,2-a]piridin-származékok, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk herpeszvírus-fertőzések megelőzésére vagy kezelésére
AR038957A1 (es)	2001-08-15	2005-02-02	Pharmacia Corp	Terapia de combinacion para el tratamiento del cancer
WO2003031446A1 (en)	2001-10-05	2003-04-17	Smithkline Beecham Corporation	Imidazo-pyridine derivatives for use in the treatment of herpes viral infection
GB0124936D0 (en)	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124931D0 (en)	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124933D0 (en)	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124938D0 (en)	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124934D0 (en)	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124941D0 (en)	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124939D0 (en)	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
AU2002357740A1 (en)	2001-12-11	2003-06-23	Smithkline Beecham Corporation	Pyrazolo-pyridine derivatives as antiherpes agents
BRPI0307351B8 (pt)	2002-02-12	2021-05-25	Smithkline Beecham Corp	composto, composição farmacêutica, uso de um composto, e, processo para preparar um composto
US7211598B2 (en)	2002-06-28	2007-05-01	Nitromed, Inc.	Oxime and/or hydrozone containing nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use
GB0217757D0 (en)	2002-07-31	2002-09-11	Glaxo Group Ltd	Novel compounds
JP2006504728A (ja)	2002-10-03	2006-02-09	スミスクラインビーチャムコーポレーション	ピラソロピリジン誘導体系治療用化合物
KR20040072004A (ko)	2003-02-07	2004-08-16	삼성에스디아이 주식회사	유기 전계 발광 소자용 발광 화합물 및 그를 이용한 유기전계발광 소자
GB0308186D0 (en)	2003-04-09	2003-05-14	Smithkline Beecham Corp	Novel compounds
GB0308201D0 (en)	2003-04-09	2003-05-14	Smithkline Beecham Corp	Novel compounds
GB0308185D0 (en)	2003-04-09	2003-05-14	Smithkline Beecham Corp	Novel compounds
ES2275218T3 (es)	2003-05-07	2007-06-01	Osteologix A/S	Sales de estroncio hidrosolubles para el tratamiento de afecciones de cartilagos y/o huesos.
GB0318814D0 (en)	2003-08-11	2003-09-10	Smithkline Beecham Corp	Novel compounds
WO2006041855A2 (en)	2004-10-04	2006-04-20	Nitromed, Inc.	Compositions and methods using apocynin compounds and nitric oxide donors
WO2007016677A2 (en)	2005-08-02	2007-02-08	Nitromed, Inc.	Nitric oxide enhancing antimicrobial compounds, compositions and methods of use
CA2647859C (en)	2006-03-29	2016-01-05	Nitromed, Inc.	Nitric oxide enhancing prostaglandin compounds, compositions and methods of use
MY146474A (en)	2006-11-06	2012-08-15	Supergen Inc	Imidazo[1,2-b]pyridazine and pyrazolo[1,5-a]pyrimidine derivatives and their use as protein kinase inhibitors
EP2734205B1 (en)	2011-07-21	2018-03-21	Tolero Pharmaceuticals, Inc.	Heterocyclic protein kinase inhibitors
WO2016177776A1 (en)	2015-05-04	2016-11-10	Academisch Medisch Centrum	Biomarkers for the detection of aspirin insensitivity
AU2020221247B2 (en)	2019-02-12	2024-12-12	Sumitomo Pharma America, Inc.	Formulations comprising heterocyclic protein kinase inhibitors
CA3209491A1 (en)	2021-03-15	2022-09-22	Saul Yedgar	Hyaluronic acid-conjugated dipalmitoyl phosphatidyl ethanolamine in combination with non-steroidal anti-inflammatory drugs (nsaids) for treating or alleviating inflammatory disease

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3455924A (en) *	1967-02-08	1969-07-15	Upjohn Co	Dianisylimidazoles

1996
- 1996-04-02 KR KR1019970706963A patent/KR19980703559A/ko not_active Ceased
- 1996-04-02 JP JP8529971A patent/JPH11501049A/ja active Pending
- 1996-04-02 CN CN96194403A patent/CN1186492A/zh active Pending
- 1996-04-02 CZ CZ973133A patent/CZ313397A3/cs unknown
- 1996-04-02 SK SK1332-97A patent/SK133297A3/sk unknown
- 1996-04-02 AU AU52766/96A patent/AU5276696A/en not_active Abandoned
- 1996-04-02 EP EP96909164A patent/EP0819127A1/en not_active Withdrawn
- 1996-04-02 WO PCT/EP1996/001438 patent/WO1996031509A1/en not_active Ceased
- 1996-04-02 NZ NZ304886A patent/NZ304886A/en unknown
- 1996-04-02 PL PL96322623A patent/PL322623A1/xx unknown
- 1996-04-02 EA EA199700209A patent/EA199700209A1/ru unknown
- 1996-04-02 HU HU9801602A patent/HUP9801602A3/hu unknown
- 1996-04-02 CA CA002216809A patent/CA2216809A1/en not_active Abandoned
- 1996-04-02 TR TR97/01105T patent/TR199701105T1/xx unknown
1997
- 1997-09-25 IS IS4570A patent/IS4570A/is unknown
- 1997-09-30 BG BG101934A patent/BG101934A/xx unknown
- 1997-10-03 NO NO974595A patent/NO974595L/no unknown

Also Published As

Publication number	Publication date
MX9707379A (es)	1997-11-29
CN1186492A (zh)	1998-07-01
SK133297A3 (en)	1998-07-08
IS4570A (is)	1997-09-25
HUP9801602A2 (hu)	1998-11-30
JPH11501049A (ja)	1999-01-26
AU5276696A (en)	1996-10-23
NO974595L (no)	1997-12-03
HUP9801602A3 (en)	1999-01-28
BG101934A (en)	1999-04-30
WO1996031509A1 (en)	1996-10-10
EP0819127A1 (en)	1998-01-21
KR19980703559A (ko)	1998-11-05
NO974595D0 (no)	1997-10-03
CZ313397A3 (cs)	1998-03-18
NZ304886A (en)	1998-11-25
PL322623A1 (en)	1998-02-02
EA199700209A1 (ru)	1998-04-30
TR199701105T1 (xx)	1998-02-21

Legal Events

Date	Code	Title	Description
2001-04-02	FZDE	Discontinued

Publication	Publication Date	Title
NZ304886A (en)	1998-11-25	Imidazo [1,2a] pyridine derivatives, preparation and pharmaceutical compositions thereof
US6498166B1 (en)	2002-12-24	Pyrazolopyridines
US6831097B2 (en)	2004-12-14	2,3-diaryl-pyrazolo[1,5-B]pyridazines derivatives, their preparation and their use as cyclooxygenase 2 (COX-2) inhibitors
US7223772B1 (en)	2007-05-29	Pyrazolopyridine derivatives as selective cox-2 inhibitors
RU2696275C1 (ru)	2019-08-01	Производные имидазопиридина в качестве модуляторов активности tnf
WO2007032466A1 (ja)	2007-03-22	複素環化合物、その製造方法並びに用途
JP6811233B2 (ja)	2021-01-13	Ｔｎｆアルファの修飾因子として有用な環状化合物
RU2683940C1 (ru)	2019-04-03	Производные имидазотиазола в качестве модуляторов активности tnf
RU2697090C1 (ru)	2019-08-12	Производные тетрагидроимидазопиридина в качестве модуляторов активности tnf
WO2001038311A2 (en)	2001-05-31	Pyrimidine derivatives as selective inhibitors of cox-2
JP7577819B2 (ja)	2024-11-05	Ａｈｒアゴニスト
IE58739B1 (en)	1993-11-03	Tricyclic oxindole antiinflammatory agents
MXPA97007379A (en)	1998-07-03	Derivatives of imidazo [1,2-a] pirid
HRP960425A2 (en)	1998-02-28	Chemical compounds
JP3167700B1 (ja)	2001-05-21	２，３−ジアリール−ピラゾロ［１，５−ｂ］ピリダジン誘導体、その製造方法およびそのシクロオキシゲナーゼ２（ｃｏｘ−２）阻害剤としての使用
MXPA00002203A (en)	2001-03-05	2,3-diaryl-pyrazolo[1,5-b]pyridazines derivatives, their preparation and their use as cyclooxygenase 2 (cox-2) inhibitors
CZ2000800A3 (cs)	2000-08-16	2,3-diarylpyrazolo /1,5 - b/ pyridazinové deriváty
ZA200103344B (en)	2002-07-24	Pyrazolopyridine derivatives as selective COX-2 inhibitors.