CA2246336A1 - Combinations, having immunosuppressive effects, containing a cyclooxygenase-2 inhibitor and a leukotriene a4 hydrolase inhibitor - Google Patents
Combinations, having immunosuppressive effects, containing a cyclooxygenase-2 inhibitor and a leukotriene a4 hydrolase inhibitor Download PDFInfo
- Publication number
- CA2246336A1 CA2246336A1 CA002246336A CA2246336A CA2246336A1 CA 2246336 A1 CA2246336 A1 CA 2246336A1 CA 002246336 A CA002246336 A CA 002246336A CA 2246336 A CA2246336 A CA 2246336A CA 2246336 A1 CA2246336 A1 CA 2246336A1
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- CA
- Canada
- Prior art keywords
- alkyl
- methyl
- amino
- phenyl
- phenoxy
- Prior art date
- 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
Links
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title claims abstract description 26
- 229940093444 Cyclooxygenase 2 inhibitor Drugs 0.000 title claims abstract description 21
- 229940126065 leukotriene A4 hydrolase inhibitor Drugs 0.000 title claims abstract description 20
- 230000001506 immunosuppresive effect Effects 0.000 title description 3
- 210000000056 organ Anatomy 0.000 claims abstract description 21
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 6
- -1 cyano, carboxyl Chemical group 0.000 claims description 270
- 125000000217 alkyl group Chemical group 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 21
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 16
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 108010036949 Cyclosporine Proteins 0.000 claims description 14
- 229960001265 ciclosporin Drugs 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical group CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 13
- 229930105110 Cyclosporin A Natural products 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 229930182912 cyclosporin Natural products 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000005466 alkylenyl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 125000002971 oxazolyl group Chemical group 0.000 claims description 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 11
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 11
- 125000004043 oxo group Chemical group O=* 0.000 claims description 11
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 10
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 9
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 206010020751 Hypersensitivity Diseases 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 6
- 230000001154 acute effect Effects 0.000 claims description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 230000001028 anti-proliverative effect Effects 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 230000009610 hypersensitivity Effects 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 230000004044 response Effects 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 5
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 5
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 5
- 125000006003 dichloroethyl group Chemical group 0.000 claims description 5
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000006343 heptafluoro propyl group Chemical group 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 210000000265 leukocyte Anatomy 0.000 claims description 5
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- AJFTZWGGHJXZOB-UHFFFAOYSA-N DuP 697 Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)SC(Br)=C1 AJFTZWGGHJXZOB-UHFFFAOYSA-N 0.000 claims description 4
- 206010018691 Granuloma Diseases 0.000 claims description 4
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 claims description 4
- KTDZCOWXCWUPEO-UHFFFAOYSA-N NS-398 Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1CCCCC1 KTDZCOWXCWUPEO-UHFFFAOYSA-N 0.000 claims description 4
- 206010040070 Septic Shock Diseases 0.000 claims description 4
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 230000001363 autoimmune Effects 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
- 125000006001 difluoroethyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 229950005722 flosulide Drugs 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000004470 heterocyclooxy group Chemical group 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 230000028993 immune response Effects 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 229960001929 meloxicam Drugs 0.000 claims description 4
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 4
- CXJONBHNIJFARE-UHFFFAOYSA-N n-[6-(2,4-difluorophenoxy)-1-oxo-2,3-dihydroinden-5-yl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=2CCC(=O)C=2C=C1OC1=CC=C(F)C=C1F CXJONBHNIJFARE-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 230000036303 septic shock Effects 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- ZVSGOCRXDUNISM-UHFFFAOYSA-N 4-[5-(2-hydroxyethyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(CCO)ON=C1C1=CC=CC=C1 ZVSGOCRXDUNISM-UHFFFAOYSA-N 0.000 claims description 3
- NSQNZEUFHPTJME-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C(F)(F)F)=N1 NSQNZEUFHPTJME-UHFFFAOYSA-N 0.000 claims description 3
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 3
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 3
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
- 208000015023 Graves' disease Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 3
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 3
- WAZQAZKAZLXFMK-UHFFFAOYSA-N deracoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WAZQAZKAZLXFMK-UHFFFAOYSA-N 0.000 claims description 3
- 208000024908 graft versus host disease Diseases 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 230000009257 reactivity Effects 0.000 claims description 3
- 206010043778 thyroiditis Diseases 0.000 claims description 3
- NSRMOHFGSWCCFK-UHFFFAOYSA-N 4-[2-(5-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide Chemical compound CC1=CN=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(N)(=O)=O)=C1 NSRMOHFGSWCCFK-UHFFFAOYSA-N 0.000 claims description 2
- 208000026872 Addison Disease Diseases 0.000 claims description 2
- 206010012442 Dermatitis contact Diseases 0.000 claims description 2
- 206010037549 Purpura Diseases 0.000 claims description 2
- 241001672981 Purpura Species 0.000 claims description 2
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 2
- 208000024780 Urticaria Diseases 0.000 claims description 2
- 230000007815 allergy Effects 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims description 2
- 208000010247 contact dermatitis Diseases 0.000 claims description 2
- 208000007475 hemolytic anemia Diseases 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
- 239000003018 immunosuppressive agent Substances 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 206010043554 thrombocytopenia Diseases 0.000 claims description 2
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims 3
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 3
- 125000001769 aryl amino group Chemical group 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- OUHAMHSISQCVQY-UHFFFAOYSA-N 1-[2-(4-benzylphenoxy)ethyl]-2-methyl-4-(2h-tetrazol-5-yl)piperidine Chemical compound CC1CC(C=2NN=NN=2)CCN1CCOC(C=C1)=CC=C1CC1=CC=CC=C1 OUHAMHSISQCVQY-UHFFFAOYSA-N 0.000 claims 2
- IMGGKNXDSXRLHK-UHFFFAOYSA-N 2-[4-[4-(2-pyrrolidin-1-ylethoxy)phenoxy]phenyl]-1,3-oxazole Chemical compound C=1C=C(OC=2C=CC(=CC=2)C=2OC=CN=2)C=CC=1OCCN1CCCC1 IMGGKNXDSXRLHK-UHFFFAOYSA-N 0.000 claims 2
- FOPWYBMDYRFLEB-UHFFFAOYSA-N 2-[5-(3,4-difluorophenyl)-2-(trifluoromethyl)-1,3-oxazol-4-yl]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1C1=C(C=2C=C(F)C(F)=CC=2)OC(C(F)(F)F)=N1 FOPWYBMDYRFLEB-UHFFFAOYSA-N 0.000 claims 2
- TZUKXDRCVJCLLL-UHFFFAOYSA-N 2-methyl-5-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound C1=NC(C)=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(C)(=O)=O)C=C1 TZUKXDRCVJCLLL-UHFFFAOYSA-N 0.000 claims 2
- ZJOUYQCSZYKGKU-UHFFFAOYSA-N 3-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=NC=CC=2)=NC(C(F)(F)F)=C1 ZJOUYQCSZYKGKU-UHFFFAOYSA-N 0.000 claims 2
- SBBJJLDNKNNWFJ-UHFFFAOYSA-N 3-[3-(4-benzylphenoxy)propyl-methylamino]propanoic acid;hydrochloride Chemical compound Cl.C1=CC(OCCCN(C)CCC(O)=O)=CC=C1CC1=CC=CC=C1 SBBJJLDNKNNWFJ-UHFFFAOYSA-N 0.000 claims 2
- WXPJULBDMSVCLI-UHFFFAOYSA-N 3-[methyl-[3-[4-(4-phenylphenoxy)phenoxy]propyl]amino]propanoic acid Chemical compound C1=CC(OCCCN(C)CCC(O)=O)=CC=C1OC1=CC=C(C=2C=CC=CC=2)C=C1 WXPJULBDMSVCLI-UHFFFAOYSA-N 0.000 claims 2
- GMDFARFIYKWUOZ-UHFFFAOYSA-N 3-[methyl-[3-[4-(thiophen-2-ylmethyl)phenoxy]propyl]amino]propanoic acid Chemical compound C1=CC(OCCCN(C)CCC(O)=O)=CC=C1CC1=CC=CS1 GMDFARFIYKWUOZ-UHFFFAOYSA-N 0.000 claims 2
- WSHWIOIPTHKMJC-UHFFFAOYSA-N 3-[methyl-[3-[4-(thiophen-3-ylmethyl)phenoxy]propyl]amino]propanoic acid Chemical compound C1=CC(OCCCN(C)CCC(O)=O)=CC=C1CC1=CSC=C1 WSHWIOIPTHKMJC-UHFFFAOYSA-N 0.000 claims 2
- RBIMSEGCQFORTH-UHFFFAOYSA-N 4-(2-methyl-4-phenyl-1,3-oxazol-5-yl)benzenesulfonamide Chemical compound O1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=C(S(N)(=O)=O)C=C1 RBIMSEGCQFORTH-UHFFFAOYSA-N 0.000 claims 2
- INRQTVDUZFESAO-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C(F)=CC=2)C(=O)OC1 INRQTVDUZFESAO-UHFFFAOYSA-N 0.000 claims 2
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims 2
- NBVALOWOMUMEJI-UHFFFAOYSA-N ethyl 1-[2-(4-benzylphenoxy)ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCOC(C=C1)=CC=C1CC1=CC=CC=C1 NBVALOWOMUMEJI-UHFFFAOYSA-N 0.000 claims 2
- NXZVXXACWZJUDZ-UHFFFAOYSA-N methyl 3-[methyl-[3-[4-(thiophen-2-ylmethyl)phenoxy]propyl]amino]propanoate Chemical compound C1=CC(OCCCN(C)CCC(=O)OC)=CC=C1CC1=CC=CS1 NXZVXXACWZJUDZ-UHFFFAOYSA-N 0.000 claims 2
- BYJHZLDLKOKIFU-UHFFFAOYSA-N methyl 3-[methyl-[3-[4-(thiophen-3-ylmethyl)phenoxy]propyl]amino]propanoate Chemical compound C1=CC(OCCCN(C)CCC(=O)OC)=CC=C1CC1=CSC=C1 BYJHZLDLKOKIFU-UHFFFAOYSA-N 0.000 claims 2
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims 2
- IUWJOVIQIJRTOX-UHFFFAOYSA-N 3-[3-[4-(4-fluorophenoxy)phenoxy]propyl-methylamino]propanoic acid Chemical compound C1=CC(OCCCN(C)CCC(O)=O)=CC=C1OC1=CC=C(F)C=C1 IUWJOVIQIJRTOX-UHFFFAOYSA-N 0.000 claims 1
- 208000024869 Goodpasture syndrome Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000003807 Graves Disease Diseases 0.000 claims 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 1
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 1
- 201000009906 Meningitis Diseases 0.000 claims 1
- 208000003250 Mixed connective tissue disease Diseases 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 1
- 201000002491 encephalomyelitis Diseases 0.000 claims 1
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims 1
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims 1
- 229940124589 immunosuppressive drug Drugs 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000005951 type IV hypersensitivity Effects 0.000 claims 1
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Landscapes
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- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
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- Diabetes (AREA)
- Neurology (AREA)
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- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
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| WO1997029776A1 (en) * | 1996-02-13 | 1997-08-21 | G.D. Searle & Co. | Combinations having immunosuppressive effects, containing cyclooxygenase-2-inhibitors and 5-lipoxygenase inhibitors |
| DE69715382T2 (de) * | 1996-02-13 | 2003-04-30 | G.D. Searle & Co., Chicago | Arzneimittelkombinationen mit immunosuppressiven wirkungen welche cyclooxygenase-2 inhibitoren und leukotrien lta4 hydrase-inhibitoren enthalten |
| SE9703693D0 (sv) * | 1997-10-10 | 1997-10-10 | Astra Pharma Prod | Novel combination |
| PT1303265E (pt) * | 2000-07-20 | 2007-10-09 | Lauras As | ''utilização de inibidores da cox-2 como imuno-estimulantes, no tratamento do vih ou da sida'' |
| GB0112348D0 (en) | 2001-05-19 | 2001-07-11 | Smithkline Beecham Plc | Compounds |
| AR038957A1 (es) | 2001-08-15 | 2005-02-02 | Pharmacia Corp | Terapia de combinacion para el tratamiento del cancer |
| MXPA04003451A (es) | 2001-10-09 | 2005-02-17 | Dimensional Pharm Inc | Difeniloxazoles substituidos, la sintesis de los mismos y el uso de los mismo como detectores fluorescencia. |
| AU2003263043A1 (en) * | 2002-08-28 | 2004-03-19 | Sangstat Medical Corporation | Methods and compostions for immune tolerance |
| US7851486B2 (en) | 2002-10-17 | 2010-12-14 | Decode Genetics Ehf. | Susceptibility gene for myocardial infarction, stroke, and PAOD; methods of treatment |
| US7507531B2 (en) | 2002-10-17 | 2009-03-24 | Decode Genetics Chf. | Use of 5-lipoxygenase activating protein (FLAP) gene to assess susceptibility for myocardial infarction |
| GT200600158A (es) * | 2005-04-22 | 2006-11-28 | Cristales formados de clorhidrato de {[(2r)-7-(2,6-diclorofenil)-5-fluoro-2,3-dihidro-1-benzofurano-2-il]metil}amina | |
| AT502258B1 (de) * | 2005-07-22 | 2007-09-15 | Univ Wien | Cox-i-inhibitorverbindungen |
| NL2000351C2 (nl) | 2005-12-22 | 2007-09-11 | Pfizer Prod Inc | Estrogeen-modulatoren. |
| US7737145B2 (en) * | 2005-12-29 | 2010-06-15 | Estrellita Pharmaceuticals, Llc | Diamine derivatives as inhibitors of leukotriene A4 hydrolase |
| TW200932236A (en) * | 2007-10-31 | 2009-08-01 | Janssen Pharmaceutica Nv | Aryl-substituted bridged diamines as modulators of leukotriene A4 hydrolase |
| RS52712B (sr) | 2008-04-11 | 2013-08-30 | Janssen Pharmaceutica N.V. | Tiazolopiridin-2-iloksi-fenil i tiazolopirazin-2-iloksi-fenil amini kao modulatori leukotrien a4 hidrolaze |
| MX2011012190A (es) | 2009-05-14 | 2011-12-08 | Janssen Pharmaceutica Nv | Compuestos con dos porciones de heteroarilo biciclico fusionado como moduladores de la leucotrieno a4 hidrolasa. |
| EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
| CA2905340C (en) | 2013-03-12 | 2022-05-31 | Celtaxsys, Inc. | Low dose oral formulations of acebilustat |
| MX2015011677A (es) | 2013-03-14 | 2016-07-08 | Celtaxsys Inc | Inhibidores de leucotrieno a4 hidrolasa. |
| JP6534650B2 (ja) | 2013-03-14 | 2019-06-26 | セルタクシス，インコーポレイテッド | ロイコトリエンａ４加水分解酵素の阻害剤 |
| EP2968265A4 (en) | 2013-03-14 | 2016-12-28 | Celtaxsys Inc | INHIBITORS OF THE LEUKOTRIEN A4 HYDROLASE |
| CA3252823A1 (en) | 2016-06-13 | 2025-02-25 | Gilead Sciences Inc | Fxr (nr1h4) modulating compounds |
| SI3730487T1 (sl) | 2016-06-13 | 2022-08-31 | Gilead Sciences, Inc. | Azetidinski derivati kot modulatorji FXR (NR1H4) |
| JP6906626B2 (ja) | 2017-03-28 | 2021-07-21 | ギリアード サイエンシーズ， インコーポレイテッド | 肝疾患を処置するための治療的組み合わせ |
| WO2019232306A1 (en) | 2018-05-31 | 2019-12-05 | Celtaxsys, Inc. | Method of reducing pulmonary exacerbations in respiratory disease patients |
| US11225473B2 (en) | 2019-01-15 | 2022-01-18 | Gilead Sciences, Inc. | FXR (NR1H4) modulating compounds |
| EP3927683A1 (en) | 2019-02-19 | 2021-12-29 | Gilead Sciences, Inc. | Solid forms of fxr agonists |
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| JPS59196839A (ja) | 1983-04-21 | 1984-11-08 | Sankyo Co Ltd | フエニル酢酸誘導体 |
| US4873259A (en) | 1987-06-10 | 1989-10-10 | Abbott Laboratories | Indole, benzofuran, benzothiophene containing lipoxygenase inhibiting compounds |
| US5242940A (en) | 1987-05-29 | 1993-09-07 | Ortho Pharmaceutical Corporation | Pharmacologically active N-1 and C-5 heterocyclic pyrazoles and method for synthesizing the same |
| ATE109970T1 (de) | 1987-09-03 | 1994-09-15 | Univ Georgia Res Found | Cyclosporin-augenmittel. |
| US5234950A (en) | 1988-12-23 | 1993-08-10 | Imperial Chemical Industries Plc | Tetrahydrofuran derivatives |
| GB8927287D0 (en) | 1988-12-23 | 1990-01-31 | Ici Plc | Cyclic ether derivatives |
| US5220059A (en) | 1990-04-19 | 1993-06-15 | Abbott Laboratories | Lipoxygenase-inhibiting compounds derived from non-steroidal antiinflammatory carboxylic acids |
| WO1992001682A1 (en) | 1990-07-25 | 1992-02-06 | Abbott Laboratories | Acetylene derivatives having lipoxygenase inhibitory activity |
| IE913655A1 (en) | 1990-11-06 | 1992-05-22 | Zeneca Ltd | Synergistic agents |
| JPH06505239A (ja) | 1991-01-31 | 1994-06-16 | ワーナー−ランバート・コンパニー | 抗炎症剤として有用な４，６−ジ−第三ブチル−５−ヒドロキシ−１，３−ピリミジンの置換されたヘテロアリール類似体 |
| GB9215921D0 (en) | 1992-07-27 | 1992-09-09 | Wellcome Found | Anti-inflammatory compounds |
| US5354865A (en) | 1992-09-10 | 1994-10-11 | Abbott Laboratories | Phenylmethyl derivatives having lipoxygenase inhibitory activity |
| US5288751A (en) | 1992-11-06 | 1994-02-22 | Abbott Laboratories | [(Substituted) phenyalkyl]furylalkynyl-and [substituted) phenyalkyl] thienylalkynyl-N-hydroxyurea inhibitors or leukotriene biosynthesis |
| US5604260A (en) | 1992-12-11 | 1997-02-18 | Merck Frosst Canada Inc. | 5-methanesulfonamido-1-indanones as an inhibitor of cyclooxygenase-2 |
| CA2152792C (en) | 1993-01-15 | 2000-02-15 | Stephen R. Bertenshaw | Novel 3,4-diaryl thiophenes and analogs thereof having use as antiinflammatory agents |
| US5409944A (en) | 1993-03-12 | 1995-04-25 | Merck Frosst Canada, Inc. | Alkanesulfonamido-1-indanone derivatives as inhibitors of cyclooxygenase |
| AU6718494A (en) | 1993-05-13 | 1994-12-12 | Merck Frosst Canada Inc. | 2-substituted-3,4-diarylthiophene derivatives as inhibitors of cyclooxygenase |
| US5380738A (en) | 1993-05-21 | 1995-01-10 | Monsanto Company | 2-substituted oxazoles further substituted by 4-fluorophenyl and 4-methylsulfonylphenyl as antiinflammatory agents |
| US5474995A (en) | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5298521A (en) | 1993-08-30 | 1994-03-29 | Ortho Pharmaceutical Corporation | 1,5-diphenyl-3-pyrazolylalkyl-N-hydroxydithiocaramates, compositions and use |
| US5344991A (en) | 1993-10-29 | 1994-09-06 | G.D. Searle & Co. | 1,2 diarylcyclopentenyl compounds for the treatment of inflammation |
| ATE233245T1 (de) | 1993-11-30 | 2003-03-15 | Searle & Co | Substituierte pyrazolyl-benzolsulfonamide und ihre verwendung als cyclooxygenaseii inhibitoren |
| US5393790A (en) | 1994-02-10 | 1995-02-28 | G.D. Searle & Co. | Substituted spiro compounds for the treatment of inflammation |
| US5486534A (en) * | 1994-07-21 | 1996-01-23 | G. D. Searle & Co. | 3,4-substituted pyrazoles for the treatment of inflammation |
| US5700816A (en) * | 1995-06-12 | 1997-12-23 | Isakson; Peter C. | Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitor and a leukotriene A4 hydrolase inhibitor |
| CA2224517A1 (en) | 1995-06-12 | 1996-12-27 | G.D. Searle & Co. | Compositions comprising a cyclooxygenase-2 inhibitor and a 5-lipoxygenase inhibitor |
| DE69715382T2 (de) * | 1996-02-13 | 2003-04-30 | G.D. Searle & Co., Chicago | Arzneimittelkombinationen mit immunosuppressiven wirkungen welche cyclooxygenase-2 inhibitoren und leukotrien lta4 hydrase-inhibitoren enthalten |
| PT880362E (pt) * | 1996-02-13 | 2005-10-31 | Searle & Co | Composicoes compreendendo um inibidor do cicloxigenase tipo 2 e um antagonista do receptor do leucotrieno b4 |
-
1997
- 1997-02-11 DE DE69715382T patent/DE69715382T2/de not_active Expired - Fee Related
- 1997-02-11 ES ES97907545T patent/ES2183140T3/es not_active Expired - Lifetime
- 1997-02-11 AU AU19525/97A patent/AU1952597A/en not_active Abandoned
- 1997-02-11 PT PT97907545T patent/PT880363E/pt unknown
- 1997-02-11 AT AT97907545T patent/ATE223732T1/de not_active IP Right Cessation
- 1997-02-11 WO PCT/US1997/001421 patent/WO1997029774A1/en not_active Ceased
- 1997-02-11 JP JP52935897A patent/JP2001506574A/ja not_active Ceased
- 1997-02-11 CA CA002246336A patent/CA2246336A1/en not_active Abandoned
- 1997-02-11 DK DK97907545T patent/DK0880363T3/da active
- 1997-02-11 EP EP97907545A patent/EP0880363B1/en not_active Expired - Lifetime
-
2000
- 2000-01-21 US US09/489,311 patent/US6407140B1/en not_active Expired - Fee Related
-
2002
- 2002-05-02 US US10/137,231 patent/US20030004191A1/en not_active Abandoned
-
2004
- 2004-08-27 US US10/928,835 patent/US20050043355A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US6407140B1 (en) | 2002-06-18 |
| DE69715382D1 (de) | 2002-10-17 |
| ATE223732T1 (de) | 2002-09-15 |
| US20030004191A1 (en) | 2003-01-02 |
| US20050043355A1 (en) | 2005-02-24 |
| JP2001506574A (ja) | 2001-05-22 |
| AU1952597A (en) | 1997-09-02 |
| EP0880363A1 (en) | 1998-12-02 |
| DK0880363T3 (da) | 2003-01-20 |
| ES2183140T3 (es) | 2003-03-16 |
| WO1997029774A1 (en) | 1997-08-21 |
| PT880363E (pt) | 2002-12-31 |
| DE69715382T2 (de) | 2003-04-30 |
| EP0880363B1 (en) | 2002-09-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |