CA2653872A1 - Novel heterocyclic compounds - Google Patents
Novel heterocyclic compounds Download PDFInfo
- Publication number
- CA2653872A1 CA2653872A1 CA002653872A CA2653872A CA2653872A1 CA 2653872 A1 CA2653872 A1 CA 2653872A1 CA 002653872 A CA002653872 A CA 002653872A CA 2653872 A CA2653872 A CA 2653872A CA 2653872 A1 CA2653872 A1 CA 2653872A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- phenyl
- methyl
- oxy
- 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
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
- 201000004792 malaria Diseases 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 265
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 45
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 27
- 238000011282 treatment Methods 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 18
- 241000223960 Plasmodium falciparum Species 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 241000282414 Homo sapiens Species 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 208000015181 infectious disease Diseases 0.000 claims description 11
- 230000002829 reductive effect Effects 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- QGQFNQWZHHSZIC-UHFFFAOYSA-N 5-chloro-2-(hydroxymethyl)-6-methyl-3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(CO)=C1C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 QGQFNQWZHHSZIC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- FPLYZPSLKQLYKK-UHFFFAOYSA-N 3-chloro-2-(hydroxyiminomethyl)-6-methyl-5-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1H-pyridin-4-one Chemical compound N1C(C=NO)=C(Cl)C(=O)C(C=2C=CC(OC=3C=CC(OC(F)(F)F)=CC=3)=CC=2)=C1C FPLYZPSLKQLYKK-UHFFFAOYSA-N 0.000 claims description 2
- PBBRXPIBBBJNSH-UHFFFAOYSA-N 3-chloro-2-(hydroxymethyl)-6-methyl-5-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound N1C(CO)=C(Cl)C(=O)C(C=2C=CC(OC=3C=CC(OC(F)(F)F)=CC=3)=CC=2)=C1C PBBRXPIBBBJNSH-UHFFFAOYSA-N 0.000 claims description 2
- YVUMFLJJKXPWIK-UHFFFAOYSA-N 5-chloro-2-(3-hydroxypropyl)-6-methyl-3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(CCCO)=C1C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 YVUMFLJJKXPWIK-UHFFFAOYSA-N 0.000 claims description 2
- OTKMQZNYPLNRQB-UHFFFAOYSA-N 5-chloro-2-(hydroxyiminomethyl)-6-methyl-3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1H-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C=NO)=C1C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 OTKMQZNYPLNRQB-UHFFFAOYSA-N 0.000 claims description 2
- OROGEAPBNAKLSB-UHFFFAOYSA-N 5-chloro-2-(methoxyiminomethyl)-6-methyl-3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound N1C(C)=C(Cl)C(=O)C(C=2C=CC(OC=3C=CC(OC(F)(F)F)=CC=3)=CC=2)=C1C=NOC OROGEAPBNAKLSB-UHFFFAOYSA-N 0.000 claims description 2
- 150000002081 enamines Chemical class 0.000 claims description 2
- 238000013160 medical therapy Methods 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- VBDWNBIKGCBULL-UHFFFAOYSA-N 3-chloro-2-(hydroxymethyl)-6-methyl-5-[4-[3-(trifluoromethyl)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound N1C(CO)=C(Cl)C(=O)C(C=2C=CC(OC=3C=C(C=CC=3)C(F)(F)F)=CC=2)=C1C VBDWNBIKGCBULL-UHFFFAOYSA-N 0.000 claims 1
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- QHNRLLYYTVFXLI-UHFFFAOYSA-N N1=CCC(C=C1)=O.N1=CCC(C=C1)=O Chemical class N1=CCC(C=C1)=O.N1=CCC(C=C1)=O QHNRLLYYTVFXLI-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 136
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 71
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 46
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 37
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 35
- 239000002585 base Substances 0.000 description 33
- 150000003839 salts Chemical class 0.000 description 31
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 235000019439 ethyl acetate Nutrition 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 238000003556 assay Methods 0.000 description 21
- 239000012043 crude product Substances 0.000 description 20
- -1 alkaline-earth-metal salts Chemical class 0.000 description 19
- 239000012300 argon atmosphere Substances 0.000 description 19
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 19
- 239000000725 suspension Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000012267 brine Substances 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
- 244000045947 parasite Species 0.000 description 17
- 229910052763 palladium Inorganic materials 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 15
- 229910000029 sodium carbonate Inorganic materials 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000007832 Na2SO4 Substances 0.000 description 14
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical class OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 235000017550 sodium carbonate Nutrition 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000872 buffer Substances 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
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- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
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- 239000002609 medium Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 239000012453 solvate Substances 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 7
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
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- 239000003960 organic solvent Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
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- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 description 5
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- OYVXVLSZQHSNDK-UHFFFAOYSA-N n-methoxy-n-methylacetamide Chemical compound CON(C)C(C)=O OYVXVLSZQHSNDK-UHFFFAOYSA-N 0.000 description 5
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- DIOHEXPTUTVCNX-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenyl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical group FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 DIOHEXPTUTVCNX-UHFFFAOYSA-N 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 4
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- 229910004879 Na2S2O5 Inorganic materials 0.000 description 4
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- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
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- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
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- 238000010511 deprotection reaction Methods 0.000 description 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
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- 239000000787 lecithin Substances 0.000 description 4
- 235000010445 lecithin Nutrition 0.000 description 4
- 229940067606 lecithin Drugs 0.000 description 4
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 201000002612 sleeping sickness Diseases 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007886 soft shell capsule Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 229960004673 sulfadoxine Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229950000856 tafenoquine Drugs 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 210000003812 trophozoite Anatomy 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06381025.3 | 2006-05-31 | ||
| EP06381025A EP1862459A1 (en) | 2006-05-31 | 2006-05-31 | Novel heterocyclic compounds |
| EP07380072.4 | 2007-03-08 | ||
| EP07380072A EP1967515A1 (en) | 2007-03-08 | 2007-03-08 | Heterocyclic compounds |
| PCT/EP2007/055188 WO2007138048A1 (en) | 2006-05-31 | 2007-05-29 | Novel heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2653872A1 true CA2653872A1 (en) | 2007-12-06 |
Family
ID=38480438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002653872A Abandoned CA2653872A1 (en) | 2006-05-31 | 2007-05-29 | Novel heterocyclic compounds |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7674808B2 (enExample) |
| EP (1) | EP2024332A1 (enExample) |
| JP (1) | JP2009538873A (enExample) |
| KR (1) | KR20090012342A (enExample) |
| AR (1) | AR060974A1 (enExample) |
| AU (1) | AU2007267093A1 (enExample) |
| BR (1) | BRPI0711783A2 (enExample) |
| CA (1) | CA2653872A1 (enExample) |
| CR (1) | CR10492A (enExample) |
| EA (1) | EA200870545A1 (enExample) |
| IL (1) | IL195158A0 (enExample) |
| MA (1) | MA30487B1 (enExample) |
| MX (1) | MX2008015291A (enExample) |
| NO (1) | NO20085087L (enExample) |
| PE (1) | PE20080453A1 (enExample) |
| TW (1) | TW200817331A (enExample) |
| WO (1) | WO2007138048A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8877178B2 (en) | 2003-12-19 | 2014-11-04 | The Iams Company | Methods of use of probiotic bifidobacteria for companion animals |
| US20050158294A1 (en) | 2003-12-19 | 2005-07-21 | The Procter & Gamble Company | Canine probiotic Bifidobacteria pseudolongum |
| EP2261323A1 (en) | 2005-05-31 | 2010-12-15 | The Iams Company | Feline probiotic lactobacilli |
| JP4938006B2 (ja) | 2005-05-31 | 2012-05-23 | ザ・アイムス・カンパニー | ネコ科動物プロバイオティク・ビフィドバクテリア |
| WO2008093303A2 (en) | 2007-02-01 | 2008-08-07 | The Iams Company | Method for decreasing inflammation and stress in a mammal using glucose antimetaboltes, avocado or avocado extracts |
| CN101932561A (zh) * | 2007-11-30 | 2010-12-29 | 葛兰素集团有限公司 | 抗疟疾化合物的晶型 |
| US9771199B2 (en) * | 2008-07-07 | 2017-09-26 | Mars, Incorporated | Probiotic supplement, process for making, and packaging |
| US9232813B2 (en) * | 2008-07-07 | 2016-01-12 | The Iams Company | Probiotic supplement, process for making, and packaging |
| EP2246329A1 (en) | 2009-01-19 | 2010-11-03 | Glaxo Group Limited | 4(1H)-pyridinone derivatives and their use as antimalaria agents |
| WO2010081904A1 (en) | 2009-01-19 | 2010-07-22 | Glaxo Group Limited | 4 ( 1h) -pyridinone derivatives and their use as antimalaria agents |
| TW201039834A (en) | 2009-02-20 | 2010-11-16 | Glaxo Group Ltd | Novel heterocyclic compounds |
| WO2010142741A1 (en) * | 2009-06-12 | 2010-12-16 | Glaxo Group Limited | Phenylpyridylpyridones for use as antimalarial agents |
| US10104903B2 (en) | 2009-07-31 | 2018-10-23 | Mars, Incorporated | Animal food and its appearance |
| US9801627B2 (en) * | 2014-09-26 | 2017-10-31 | Ethicon Llc | Fastener cartridge for creating a flexible staple line |
| JOP20180072A1 (ar) | 2014-09-11 | 2019-01-30 | Lilly Co Eli | علاج الأعراض المرتبطة بالعلاج بالحرمان من الأندروجين |
| WO2016169908A1 (en) * | 2015-04-21 | 2016-10-27 | Glaxosmithkline Intellectual Property Development Limited | Uracil derivatives for the treatment of malaria |
| GB201809627D0 (en) * | 2018-06-12 | 2018-07-25 | Biorelevant Com Ltd | Methods for preparing buffer solutions suitable for in vitro drug dissolution testing, drug solubility testing and/or drug profiling |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5403934A (en) * | 1990-03-12 | 1995-04-04 | Burroughs Wellcome Co. | Heterocyclic compounds |
| GB9005518D0 (en) * | 1990-03-12 | 1990-05-09 | Wellcome Found | Heterocyclic compounds |
| GB9100465D0 (en) * | 1991-01-09 | 1991-02-20 | Hider Robert C | Pharmaceutical compositions |
-
2007
- 2007-05-29 WO PCT/EP2007/055188 patent/WO2007138048A1/en not_active Ceased
- 2007-05-29 EP EP07729610A patent/EP2024332A1/en not_active Withdrawn
- 2007-05-29 PE PE2007000667A patent/PE20080453A1/es not_active Application Discontinuation
- 2007-05-29 US US11/754,382 patent/US7674808B2/en not_active Expired - Fee Related
- 2007-05-29 AU AU2007267093A patent/AU2007267093A1/en not_active Abandoned
- 2007-05-29 EA EA200870545A patent/EA200870545A1/ru unknown
- 2007-05-29 CA CA002653872A patent/CA2653872A1/en not_active Abandoned
- 2007-05-29 TW TW096119056A patent/TW200817331A/zh unknown
- 2007-05-29 MX MX2008015291A patent/MX2008015291A/es unknown
- 2007-05-29 BR BRPI0711783-3A patent/BRPI0711783A2/pt not_active IP Right Cessation
- 2007-05-29 AR ARP070102297A patent/AR060974A1/es not_active Application Discontinuation
- 2007-05-29 JP JP2009512577A patent/JP2009538873A/ja active Pending
- 2007-05-29 KR KR1020087029153A patent/KR20090012342A/ko not_active Withdrawn
- 2007-05-31 US US11/755,849 patent/US7629365B2/en not_active Expired - Fee Related
-
2008
- 2008-11-06 IL IL195158A patent/IL195158A0/en unknown
- 2008-12-01 MA MA31430A patent/MA30487B1/fr unknown
- 2008-12-05 NO NO20085087A patent/NO20085087L/no not_active Application Discontinuation
- 2008-12-10 CR CR10492A patent/CR10492A/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EA200870545A1 (ru) | 2009-12-30 |
| US20080021073A1 (en) | 2008-01-24 |
| IL195158A0 (en) | 2009-08-03 |
| BRPI0711783A2 (pt) | 2011-11-29 |
| US20070281977A1 (en) | 2007-12-06 |
| NO20085087L (no) | 2009-02-20 |
| KR20090012342A (ko) | 2009-02-03 |
| MX2008015291A (es) | 2008-12-12 |
| PE20080453A1 (es) | 2008-05-29 |
| AR060974A1 (es) | 2008-07-23 |
| MA30487B1 (fr) | 2009-06-01 |
| EP2024332A1 (en) | 2009-02-18 |
| US7674808B2 (en) | 2010-03-09 |
| TW200817331A (en) | 2008-04-16 |
| CR10492A (es) | 2009-01-27 |
| AU2007267093A1 (en) | 2007-12-06 |
| WO2007138048A1 (en) | 2007-12-06 |
| US7629365B2 (en) | 2009-12-08 |
| JP2009538873A (ja) | 2009-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20130529 |