DE05028442T1 - W-carboxyaryl substituierte diphenyl Harnstoffe als raf kinase inhibitoren - Google Patents
W-carboxyaryl substituierte diphenyl Harnstoffe als raf kinase inhibitoren Download PDFInfo
- Publication number
- DE05028442T1 DE05028442T1 DE05028442T DE05028442T DE05028442T1 DE 05028442 T1 DE05028442 T1 DE 05028442T1 DE 05028442 T DE05028442 T DE 05028442T DE 05028442 T DE05028442 T DE 05028442T DE 05028442 T1 DE05028442 T1 DE 05028442T1
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- group
- phenyl
- halogen
- heteroatoms selected
- 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.)
- Pending
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- -1 diphenyl ureas Chemical class 0.000 title claims 71
- 235000013877 carbamide Nutrition 0.000 title claims 23
- 102000009929 raf Kinases Human genes 0.000 title claims 7
- 108010077182 raf Kinases Proteins 0.000 title claims 7
- 235000010290 biphenyl Nutrition 0.000 title 1
- 239000004305 biphenyl Substances 0.000 title 1
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 130
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 129
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 128
- 150000001875 compounds Chemical class 0.000 claims abstract 74
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 65
- 125000001424 substituent group Chemical group 0.000 claims abstract 61
- 125000003118 aryl group Chemical group 0.000 claims abstract 33
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 24
- 125000004122 cyclic group Chemical group 0.000 claims abstract 22
- 150000003839 salts Chemical class 0.000 claims abstract 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 12
- 239000001301 oxygen Substances 0.000 claims abstract 12
- 239000011593 sulfur Substances 0.000 claims abstract 12
- 125000005750 substituted cyclic group Chemical group 0.000 claims abstract 9
- 125000004429 atom Chemical group 0.000 claims abstract 4
- 125000005842 heteroatom Chemical group 0.000 claims 122
- 229910052736 halogen Inorganic materials 0.000 claims 97
- 150000002367 halogens Chemical group 0.000 claims 96
- 229910052799 carbon Chemical group 0.000 claims 85
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 61
- 125000000217 alkyl group Chemical group 0.000 claims 38
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 36
- 229910052739 hydrogen Inorganic materials 0.000 claims 33
- 239000001257 hydrogen Substances 0.000 claims 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 30
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 21
- 239000004202 carbamide Substances 0.000 claims 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 16
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 15
- 125000002877 alkyl aryl group Chemical group 0.000 claims 15
- 150000001768 cations Chemical class 0.000 claims 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 12
- 125000006654 (C3-C12) heteroaryl group Chemical group 0.000 claims 11
- 125000004076 pyridyl group Chemical group 0.000 claims 11
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 10
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 10
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 10
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims 8
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 6
- 230000010261 cell growth Effects 0.000 claims 6
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 5
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 5
- 239000005711 Benzoic acid Substances 0.000 claims 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 5
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 5
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 5
- 125000001931 aliphatic group Chemical group 0.000 claims 5
- 239000003513 alkali Substances 0.000 claims 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 5
- 239000002585 base Substances 0.000 claims 5
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 5
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 5
- 235000010233 benzoic acid Nutrition 0.000 claims 5
- 229960004365 benzoic acid Drugs 0.000 claims 5
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 5
- 229960004106 citric acid Drugs 0.000 claims 5
- 235000015165 citric acid Nutrition 0.000 claims 5
- 239000001530 fumaric acid Substances 0.000 claims 5
- 229960002598 fumaric acid Drugs 0.000 claims 5
- 235000011087 fumaric acid Nutrition 0.000 claims 5
- 229940093915 gynecological organic acid Drugs 0.000 claims 5
- 150000007529 inorganic bases Chemical class 0.000 claims 5
- 239000004310 lactic acid Substances 0.000 claims 5
- 229960000448 lactic acid Drugs 0.000 claims 5
- 235000014655 lactic acid Nutrition 0.000 claims 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 5
- 239000011976 maleic acid Substances 0.000 claims 5
- 229940098895 maleic acid Drugs 0.000 claims 5
- 239000001630 malic acid Substances 0.000 claims 5
- 235000011090 malic acid Nutrition 0.000 claims 5
- 229940099690 malic acid Drugs 0.000 claims 5
- 229960002510 mandelic acid Drugs 0.000 claims 5
- 150000007522 mineralic acids Chemical class 0.000 claims 5
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims 5
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims 5
- 150000007524 organic acids Chemical class 0.000 claims 5
- 235000005985 organic acids Nutrition 0.000 claims 5
- 235000006408 oxalic acid Nutrition 0.000 claims 5
- 229940116315 oxalic acid Drugs 0.000 claims 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 229960003424 phenylacetic acid Drugs 0.000 claims 5
- 239000003279 phenylacetic acid Substances 0.000 claims 5
- 229960004889 salicylic acid Drugs 0.000 claims 5
- 235000002906 tartaric acid Nutrition 0.000 claims 5
- 239000011975 tartaric acid Substances 0.000 claims 5
- 229960001367 tartaric acid Drugs 0.000 claims 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- KUJYWIMYUCLJRI-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(1,3-dioxoisoindol-5-yl)oxyphenyl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=C(C(=O)NC2=O)C2=C1 KUJYWIMYUCLJRI-UHFFFAOYSA-N 0.000 claims 2
- UDXPZWPTWCVPCT-UHFFFAOYSA-N 3-[4-(carbamoylamino)phenoxy]-N-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(OC=2C=CC(NC(N)=O)=CC=2)=C1 UDXPZWPTWCVPCT-UHFFFAOYSA-N 0.000 claims 2
- PZCQMBMLJHRIRJ-UHFFFAOYSA-N 4-[2-chloro-4-[[2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C(=CC(NC(=O)NC=3C(=CC=C(C=3)C(F)(F)F)OC)=CC=2)Cl)=C1 PZCQMBMLJHRIRJ-UHFFFAOYSA-N 0.000 claims 2
- JUFVEGCQLHSLLZ-UHFFFAOYSA-N 4-[3-(carbamoylamino)phenoxy]pyridine-2-carboxamide Chemical compound C(N)(=O)C1=NC=CC(=C1)OC=1C=C(C=CC=1)NC(=O)N JUFVEGCQLHSLLZ-UHFFFAOYSA-N 0.000 claims 2
- HRLTXHASHFPQAJ-UHFFFAOYSA-N 4-[3-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC(OC=2C=C(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)C=CC=2)=C1 HRLTXHASHFPQAJ-UHFFFAOYSA-N 0.000 claims 2
- QQZNUVIRTSPCLZ-UHFFFAOYSA-N 4-[4-[[2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]pyridine-2-carboxamide Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC(C(N)=O)=C1 QQZNUVIRTSPCLZ-UHFFFAOYSA-N 0.000 claims 2
- WWQRKFRUJIHXLV-UHFFFAOYSA-N 4-[4-[[4-bromo-3-(trifluoromethyl)phenyl]carbamoylamino]-2-chlorophenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C(=CC(NC(=O)NC=3C=C(C(Br)=CC=3)C(F)(F)F)=CC=2)Cl)=C1 WWQRKFRUJIHXLV-UHFFFAOYSA-N 0.000 claims 2
- DHMDTRVWYXIDFX-UHFFFAOYSA-N 4-[4-[[4-bromo-3-(trifluoromethyl)phenyl]carbamoylamino]-3-chlorophenoxy]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=C(Cl)C(NC(=O)NC=3C=C(C(Br)=CC=3)C(F)(F)F)=CC=2)=C1 DHMDTRVWYXIDFX-UHFFFAOYSA-N 0.000 claims 2
- UAEWBZYTKIMYRQ-UHFFFAOYSA-N 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 UAEWBZYTKIMYRQ-UHFFFAOYSA-N 0.000 claims 2
- MUMRZKBJQJIUDN-UHFFFAOYSA-N 5-[4-[(5-tert-butyl-2-methoxyphenyl)carbamoylamino]phenoxy]-2-methoxy-n-methylbenzamide Chemical compound C1=C(OC)C(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C(=CC=C(C=3)C(C)(C)C)OC)=CC=2)=C1 MUMRZKBJQJIUDN-UHFFFAOYSA-N 0.000 claims 2
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims 2
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 claims 2
- PRWMKAUQTZNYBE-UHFFFAOYSA-N [4-(4-acetylphenoxy)phenyl]urea Chemical compound C1=CC(C(=O)C)=CC=C1OC1=CC=C(NC(N)=O)C=C1 PRWMKAUQTZNYBE-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 150000003672 ureas Chemical class 0.000 claims 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
-
- 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
-
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- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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US11587799P | 1999-01-13 | 1999-01-13 | |
US115877P | 1999-01-13 | ||
US25726699A | 1999-02-25 | 1999-02-25 | |
US257266 | 1999-02-25 | ||
US42522899A | 1999-10-22 | 1999-10-22 | |
US425228 | 1999-10-22 |
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DE05028442T1 true DE05028442T1 (de) | 2007-02-22 |
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Application Number | Title | Priority Date | Filing Date |
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DE05028442T Pending DE05028442T1 (de) | 1999-01-13 | 2000-01-12 | W-carboxyaryl substituierte diphenyl Harnstoffe als raf kinase inhibitoren |
DE60044004T Expired - Lifetime DE60044004D1 (de) | 1999-01-13 | 2000-01-12 | Verwendung von Omega-Carboxyaryl-substituierten Diphenylharnstoffen als raf-Kinase-Inhibitoren |
DE60026822T Expired - Lifetime DE60026822T2 (de) | 1999-01-13 | 2000-01-12 | -g(v)-carboxyaryl substituierte diphenyl harnstoffe als raf kinase inhibitoren |
DE2000626822 Pending DE122006000059I1 (de) | 1999-01-13 | 2000-01-12 | -G(V)-Carboxyaryl substituierte Diphenyl Harnstoffe als Raf Kinase Inhibitoren |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
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DE60044004T Expired - Lifetime DE60044004D1 (de) | 1999-01-13 | 2000-01-12 | Verwendung von Omega-Carboxyaryl-substituierten Diphenylharnstoffen als raf-Kinase-Inhibitoren |
DE60026822T Expired - Lifetime DE60026822T2 (de) | 1999-01-13 | 2000-01-12 | -g(v)-carboxyaryl substituierte diphenyl harnstoffe als raf kinase inhibitoren |
DE2000626822 Pending DE122006000059I1 (de) | 1999-01-13 | 2000-01-12 | -G(V)-Carboxyaryl substituierte Diphenyl Harnstoffe als Raf Kinase Inhibitoren |
Country Status (40)
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JP (2) | JP3845792B2 (fr) |
KR (3) | KR20070020158A (fr) |
CN (2) | CN1219764C (fr) |
AR (1) | AR035310A1 (fr) |
AT (2) | ATE460398T1 (fr) |
AU (1) | AU2501600A (fr) |
BG (1) | BG65945B1 (fr) |
BR (2) | BRPI0017535B8 (fr) |
CA (1) | CA2359510C (fr) |
CU (1) | CU23213A3 (fr) |
CY (2) | CY2200149T2 (fr) |
CZ (2) | CZ299125B6 (fr) |
DE (4) | DE05028442T1 (fr) |
DK (1) | DK1140840T3 (fr) |
DZ (1) | DZ3004A1 (fr) |
EE (1) | EE04913B1 (fr) |
EG (1) | EG24407A (fr) |
ES (2) | ES2272203T3 (fr) |
GT (2) | GT200000002A (fr) |
HK (2) | HK1045504B (fr) |
HR (1) | HRP20010580B1 (fr) |
HU (2) | HU230863B1 (fr) |
IL (2) | IL144030A0 (fr) |
JO (1) | JO2373B1 (fr) |
LU (1) | LU91280I2 (fr) |
MA (1) | MA26038A1 (fr) |
ME (1) | MEP36908A (fr) |
MY (1) | MY138897A (fr) |
NL (1) | NL300242I2 (fr) |
NO (3) | NO321059B1 (fr) |
NZ (1) | NZ556598A (fr) |
PA (1) | PA8489701A1 (fr) |
PL (1) | PL215029B1 (fr) |
PT (2) | PT1690853E (fr) |
RS (1) | RS51497B (fr) |
SK (2) | SK287419B6 (fr) |
SV (1) | SV2001000004A (fr) |
TN (1) | TNSN00010A1 (fr) |
TR (1) | TR200102020T2 (fr) |
TW (1) | TWI269791B (fr) |
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ATE529406T1 (de) | 2002-02-11 | 2011-11-15 | Bayer Healthcare Llc | Aryl-harnstoffe als kinase inhibitoren |
TW200406374A (en) * | 2002-05-29 | 2004-05-01 | Novartis Ag | Diaryl urea derivatives useful for the treatment of protein kinase dependent diseases |
US20070161677A1 (en) * | 2004-01-30 | 2007-07-12 | Merck Patent Gmbh | Bisarylurea derivatives |
TW200530236A (en) * | 2004-02-23 | 2005-09-16 | Chugai Pharmaceutical Co Ltd | Heteroaryl phenylurea |
MY191349A (en) * | 2004-08-27 | 2022-06-17 | Bayer Pharmaceuticals Corp | New pharmaceutical compositions for the treatment of hyper-proliferative disorders |
BRPI0515944B1 (pt) * | 2004-09-29 | 2021-11-09 | Bayer Healthcare Llc | Processo para a preparação de 4-{4-[({[4-cloro-3-(trifluorometil)fe-nil]amino}carbonil) amino]fenóxi}nmetilpiridina-2-carboxamida |
DE102005015253A1 (de) * | 2005-04-04 | 2006-10-05 | Merck Patent Gmbh | Pyrazolderivate |
US8580798B2 (en) | 2005-12-21 | 2013-11-12 | Bayer Intellectual Property Gmbh | Substituted pyrimidine derivatives useful in the treatment of cancer and other disorders |
WO2008044688A1 (fr) * | 2006-10-11 | 2008-04-17 | Daiichi Sankyo Company, Limited | Dérivé de l'urée |
WO2008115263A2 (fr) * | 2007-03-20 | 2008-09-25 | Curis, Inc. | Inhibiteurs de la raf kinase contenant un fragment de liaison au zinc |
AU2008299703C1 (en) * | 2007-09-10 | 2013-09-05 | Cipla Limited | Process for the preparation of a RAF kinase inhibitor and intermediates for use in the process |
CN101372475B (zh) * | 2008-03-19 | 2012-01-04 | 南京工业大学 | 芳杂环取代的二苯脲类衍生物及其用途 |
CN101298427B (zh) * | 2008-06-26 | 2012-03-21 | 中国科学院广州生物医药与健康研究院 | 二芳基脲类化合物及其应用 |
TW201012467A (en) | 2008-09-16 | 2010-04-01 | Taiho Pharmaceutical Co Ltd | Antitumor agent containing 4-[[3,5-bis(trimethylsilyl)benzoyl]amino]benzoic acid |
CN103254126A (zh) * | 2008-09-19 | 2013-08-21 | 苏州泽璟生物制药有限公司 | 氘代的ω-二苯基脲及衍生物以及包含该化合物的药物组合物 |
CN101362717B (zh) * | 2008-09-28 | 2013-02-06 | 四川大学 | 4-(4-氨基苯胺基)-2-(甲基氨甲酰基)吡啶及其衍生物和它们的制备方法、用途 |
JO3101B1 (ar) * | 2008-12-02 | 2017-09-20 | Takeda Pharmaceuticals Co | مشتقات بنزوثيازول كعوامل مضادة للسرطان |
WO2010083649A1 (fr) * | 2009-01-22 | 2010-07-29 | 沈阳药科大学 | Dérivés de bisarylurée et leur utilisation |
US9181238B2 (en) * | 2010-02-05 | 2015-11-10 | Novartis Ag | N-(pyridin-2-yl)sulfonamides and compositions thereof as protein kinase inhibitors |
CN102219733A (zh) * | 2010-04-14 | 2011-10-19 | 上海医药工业研究院 | 索拉非尼的制备方法 |
CN101830847B (zh) * | 2010-05-18 | 2012-10-10 | 张南 | 抗癌用化合物及制备方法 |
CN102617458A (zh) * | 2010-05-18 | 2012-08-01 | 张南 | 抗癌用化合物的制备方法 |
WO2012041987A1 (fr) * | 2010-10-01 | 2012-04-05 | Bayer Pharma Aktiengesellschaft | Combinaisons contenant du n-(2-arylamino)arylsulfonamide substitué |
EP2661434A4 (fr) * | 2011-01-06 | 2014-07-09 | Beta Pharma Canada Inc | Nouvelles urées pour le traitement et la prévention du cancer |
CN102875460A (zh) * | 2012-05-17 | 2013-01-16 | 上海奥博生物医药技术有限公司 | 一种制备索拉非尼的方法 |
CN103508961B (zh) * | 2012-06-26 | 2015-07-22 | 中美冠科生物技术(太仓)有限公司 | 抗肿瘤药物 |
CN103408488A (zh) * | 2013-08-13 | 2013-11-27 | 张家港威胜生物医药有限公司 | 一种索拉非尼的优化合成方法 |
CN103435553A (zh) * | 2013-09-16 | 2013-12-11 | 中国药科大学 | 基于哌嗪结构的芳甲酰胺类Raf激酶抑制剂及其制备方法和用途 |
CN104672129B (zh) * | 2013-11-26 | 2019-06-25 | 广东东阳光药业有限公司 | 一种脲类化合物的制备方法 |
CN104974132B (zh) | 2014-04-08 | 2017-05-17 | 北大方正集团有限公司 | 多取代的吡啶化合物、制备方法、用途及药物组合物 |
CN104177292A (zh) * | 2014-08-08 | 2014-12-03 | 亿腾药业(泰州)有限公司 | 一种工业化生产甲苯磺酸索拉非尼多晶型ⅰ的方法 |
CA2998647A1 (fr) * | 2014-10-03 | 2016-04-07 | The Royal Institution For The Advancement Of Learning/Mcgill University | Uree et composes a base de bis-uree et analogues de ceux-ci utiles dans le traitement de maladies ou trouble a mediation par recepteur des androgenes |
CN105348186B (zh) * | 2015-10-15 | 2018-05-22 | 青岛海洋生物医药研究院股份有限公司 | 氘代双芳基脲类化合物及其制备方法和在制备抗肿瘤的药物中的应用 |
CN105753841B (zh) * | 2016-01-18 | 2018-01-05 | 西安交通大学 | 一种n‑吲唑取代硫脲类衍生物及其制备方法和应用 |
CN105924390B (zh) * | 2016-05-19 | 2018-07-10 | 广州南新制药有限公司 | 一种美他非尼的合成方法 |
CN106699652B (zh) * | 2016-11-07 | 2020-11-13 | 天津大学 | 一种索拉非尼α-氨基丁酸盐及其制备方法 |
CN108264510A (zh) | 2017-01-02 | 2018-07-10 | 上海喆邺生物科技有限公司 | 一种选择性抑制激酶化合物及其用途 |
CN107417604A (zh) * | 2017-07-25 | 2017-12-01 | 新发药业有限公司 | 4‑取代吡啶‑2‑甲酰胺化合物及其制备方法与应用 |
CA3132855A1 (fr) * | 2019-04-12 | 2020-10-15 | National Health Research Institutes | Composes heterocycliques en tant qu'inhibiteurs de kinase pour des utilisations therapeutiques |
CN113831491B (zh) * | 2021-09-30 | 2023-03-24 | 南昌大学 | 一种嘧啶唑共价有机框架的制备方法及吸附应用 |
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US4973675A (en) * | 1989-04-13 | 1990-11-27 | University Of Tennessee Research Center | Hybrid nitrosoureidoanthracyclines having antitumor activity |
US5447987A (en) * | 1993-12-24 | 1995-09-05 | Shin-Etsu Chemical Co., Ltd. | Organopolysiloxane compositions |
WO1995033458A1 (fr) * | 1994-06-02 | 1995-12-14 | Smithkline Beecham Corporation | Composes anti-inflammatoires |
US5447957A (en) * | 1994-06-02 | 1995-09-05 | Smithkline Beecham Corp. | Anti-inflammatory compounds |
JP2002500650A (ja) * | 1997-05-23 | 2002-01-08 | バイエル、コーポレイション | Rafキナーゼ阻害剤 |
DE69826695T2 (de) * | 1997-05-23 | 2006-02-02 | Bayer Pharmaceuticals Corp., West Haven | Arylharnstoffderivate zur behandlung von inflammatorischen oder immunomodulatorischen erkrankungen |
WO1999020617A1 (fr) * | 1997-10-21 | 1999-04-29 | Active Biotech Ab | Urees thiadiazoles anti-inflammatoires agissant comme inhibiteurs lfa-1 et mac-1 |
ES2153809T3 (es) * | 1997-12-22 | 2005-07-16 | Bayer Pharmaceuticals Corporation | Inhibicion de la cinasa raf por uso de difnil-ureas sustituidas simetrica y asimetricamente. |
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