CA2461128A1 - Pyrazole derivatives useful in the treatment of hyper-proliferative disorders - Google Patents
Pyrazole derivatives useful in the treatment of hyper-proliferative disorders Download PDFInfo
- Publication number
- CA2461128A1 CA2461128A1 CA002461128A CA2461128A CA2461128A1 CA 2461128 A1 CA2461128 A1 CA 2461128A1 CA 002461128 A CA002461128 A CA 002461128A CA 2461128 A CA2461128 A CA 2461128A CA 2461128 A1 CA2461128 A1 CA 2461128A1
- Authority
- CA
- Canada
- Prior art keywords
- c6alkyl
- substituted
- phenyl
- c6alkoxy
- halo
- 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
- 230000003463 hyperproliferative effect Effects 0.000 title claims abstract description 10
- 150000003217 pyrazoles Chemical class 0.000 title abstract description 7
- 238000011282 treatment Methods 0.000 title description 21
- 230000033115 angiogenesis Effects 0.000 claims abstract description 6
- 230000001419 dependent effect Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 126
- 125000001424 substituent group Chemical group 0.000 claims description 117
- -1 C1-C6alkoxy Chemical group 0.000 claims description 105
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 84
- 125000005843 halogen group Chemical group 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 60
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 57
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 35
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 32
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 30
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 26
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 23
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 10
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- MLBZTUSGUUBJLC-UHFFFAOYSA-N methyl 3-[1-[2-[2-chloro-4-(trifluoromethyl)phenoxy]ethyl]-5-ethoxypyrazol-3-yl]benzoate Chemical compound CCOC1=CC(C=2C=C(C=CC=2)C(=O)OC)=NN1CCOC1=CC=C(C(F)(F)F)C=C1Cl MLBZTUSGUUBJLC-UHFFFAOYSA-N 0.000 description 1
- AVOFSTAFWXOAFA-UHFFFAOYSA-N methyl 3-[4-bromo-1-[2-(1,6-dibromonaphthalen-2-yl)oxyethyl]-5-ethoxypyrazol-3-yl]benzoate Chemical compound N=1N(CCOC=2C(=C3C=CC(Br)=CC3=CC=2)Br)C(OCC)=C(Br)C=1C1=CC=CC(C(=O)OC)=C1 AVOFSTAFWXOAFA-UHFFFAOYSA-N 0.000 description 1
- AJABQVITPLDFAJ-UHFFFAOYSA-N methyl 3-[4-bromo-1-[2-(1,6-dibromonaphthalen-2-yl)oxyethyl]-5-propoxypyrazol-3-yl]benzoate Chemical compound N=1N(CCOC=2C(=C3C=CC(Br)=CC3=CC=2)Br)C(OCCC)=C(Br)C=1C1=CC=CC(C(=O)OC)=C1 AJABQVITPLDFAJ-UHFFFAOYSA-N 0.000 description 1
- UAPFXKYUYAGJRK-UHFFFAOYSA-N methyl 3-[4-bromo-1-[2-(4-bromo-2-methylphenoxy)ethyl]-5-ethoxypyrazol-3-yl]benzoate Chemical compound CCOC1=C(Br)C(C=2C=C(C=CC=2)C(=O)OC)=NN1CCOC1=CC=C(Br)C=C1C UAPFXKYUYAGJRK-UHFFFAOYSA-N 0.000 description 1
- SGUOUZGTQZYRLW-UHFFFAOYSA-N methyl 3-[4-bromo-1-[2-[2-chloro-4-(trifluoromethyl)phenoxy]ethyl]-5-ethoxypyrazol-3-yl]benzoate Chemical compound CCOC1=C(Br)C(C=2C=C(C=CC=2)C(=O)OC)=NN1CCOC1=CC=C(C(F)(F)F)C=C1Cl SGUOUZGTQZYRLW-UHFFFAOYSA-N 0.000 description 1
- XNIUUOPMOYYBAE-UHFFFAOYSA-N methyl 4-[1-[2-(1,6-dibromonaphthalen-2-yl)oxyethyl]-4-fluoro-5-propoxypyrazol-3-yl]benzoate Chemical compound N=1N(CCOC=2C(=C3C=CC(Br)=CC3=CC=2)Br)C(OCCC)=C(F)C=1C1=CC=C(C(=O)OC)C=C1 XNIUUOPMOYYBAE-UHFFFAOYSA-N 0.000 description 1
- ABQKTHHKZHCSIM-UHFFFAOYSA-N methyl 4-[1-[2-(1,6-dibromonaphthalen-2-yl)oxyethyl]-5-ethoxy-4-fluoropyrazol-3-yl]benzoate Chemical compound N=1N(CCOC=2C(=C3C=CC(Br)=CC3=CC=2)Br)C(OCC)=C(F)C=1C1=CC=C(C(=O)OC)C=C1 ABQKTHHKZHCSIM-UHFFFAOYSA-N 0.000 description 1
- ANRBBVNJLAHCMS-UHFFFAOYSA-N methyl 4-[1-[2-(2-chloro-4-ethylphenoxy)ethyl]-5-ethoxypyrazol-3-yl]benzoate Chemical compound CCOC1=CC(C=2C=CC(=CC=2)C(=O)OC)=NN1CCOC1=CC=C(CC)C=C1Cl ANRBBVNJLAHCMS-UHFFFAOYSA-N 0.000 description 1
- YEHCALSBHANECV-UHFFFAOYSA-N methyl 4-[1-[2-(2-chloro-4-methoxyphenoxy)ethyl]-5-ethoxypyrazol-3-yl]benzoate Chemical compound CCOC1=CC(C=2C=CC(=CC=2)C(=O)OC)=NN1CCOC1=CC=C(OC)C=C1Cl YEHCALSBHANECV-UHFFFAOYSA-N 0.000 description 1
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- IQWDFVCDMPMDPW-UHFFFAOYSA-N methyl 4-[1-[2-(2-chloro-4-naphthalen-2-ylphenoxy)ethyl]-5-ethoxypyrazol-3-yl]benzoate Chemical compound N=1N(CCOC=2C(=CC(=CC=2)C=2C=C3C=CC=CC3=CC=2)Cl)C(OCC)=CC=1C1=CC=C(C(=O)OC)C=C1 IQWDFVCDMPMDPW-UHFFFAOYSA-N 0.000 description 1
- LJNSGTXYJRVFTI-UHFFFAOYSA-N methyl 4-[1-[2-(2-chloro-4-thiophen-2-ylphenoxy)ethyl]-5-ethoxy-4-fluoropyrazol-3-yl]benzoate Chemical compound CCOC1=C(F)C(C=2C=CC(=CC=2)C(=O)OC)=NN1CCOC(C(=C1)Cl)=CC=C1C1=CC=CS1 LJNSGTXYJRVFTI-UHFFFAOYSA-N 0.000 description 1
- MJXYNBHMVNMCDU-UHFFFAOYSA-N methyl 4-[1-[2-(4-bromo-2-chlorophenoxy)ethyl]-5-ethoxypyrazol-3-yl]benzoate Chemical compound CCOC1=CC(C=2C=CC(=CC=2)C(=O)OC)=NN1CCOC1=CC=C(Br)C=C1Cl MJXYNBHMVNMCDU-UHFFFAOYSA-N 0.000 description 1
- VWUDHRMXCWVWEE-UHFFFAOYSA-N methyl 4-[1-[2-[2-chloro-4-(2-fluorophenyl)phenoxy]ethyl]-5-ethoxypyrazol-3-yl]benzoate Chemical compound CCOC1=CC(C=2C=CC(=CC=2)C(=O)OC)=NN1CCOC(C(=C1)Cl)=CC=C1C1=CC=CC=C1F VWUDHRMXCWVWEE-UHFFFAOYSA-N 0.000 description 1
- QJUJYPDOYKFEPT-UHFFFAOYSA-N methyl 4-[1-[2-[2-chloro-4-(3-chloro-4-fluorophenyl)phenoxy]ethyl]-5-ethoxypyrazol-3-yl]benzoate Chemical compound CCOC1=CC(C=2C=CC(=CC=2)C(=O)OC)=NN1CCOC(C(=C1)Cl)=CC=C1C1=CC=C(F)C(Cl)=C1 QJUJYPDOYKFEPT-UHFFFAOYSA-N 0.000 description 1
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- 238000004007 reversed phase HPLC Methods 0.000 description 1
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- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 239000008132 rose water Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
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- LLELVHKMCSBMCX-UHFFFAOYSA-M sodium 1-[(4-chloro-5-methyl-2-sulfophenyl)diazenyl]naphthalen-2-olate Chemical compound [Na+].Cc1cc(N=Nc2c(O)ccc3ccccc23)c(cc1Cl)S([O-])(=O)=O LLELVHKMCSBMCX-UHFFFAOYSA-M 0.000 description 1
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- 229960005055 sodium ascorbate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 229940105067 sodium chloride 9 mg/ml Drugs 0.000 description 1
- 239000008354 sodium chloride injection 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
- 239000001509 sodium citrate Substances 0.000 description 1
- 229960000999 sodium citrate dihydrate Drugs 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229960003339 sodium phosphate Drugs 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 229940100515 sorbitan Drugs 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 239000008227 sterile water for injection Substances 0.000 description 1
- 239000008229 sterile water for irrigation Substances 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
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- 239000002511 suppository base Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
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- 229920003051 synthetic elastomer Polymers 0.000 description 1
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- 238000009492 tablet coating Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000005751 tumor progression Effects 0.000 description 1
- 238000013414 tumor xenograft model Methods 0.000 description 1
- 238000007492 two-way ANOVA Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 206010046885 vaginal cancer Diseases 0.000 description 1
- 208000013139 vaginal neoplasm Diseases 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 201000005102 vulva cancer Diseases 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32457301P | 2001-09-25 | 2001-09-25 | |
| US60/324,573 | 2001-09-25 | ||
| PCT/US2002/029958 WO2003027074A1 (en) | 2001-09-25 | 2002-09-20 | Pyrazole derivatives useful in the treatment of hyper-proliferative disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2461128A1 true CA2461128A1 (en) | 2003-04-03 |
Family
ID=23264199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002461128A Abandoned CA2461128A1 (en) | 2001-09-25 | 2002-09-20 | Pyrazole derivatives useful in the treatment of hyper-proliferative disorders |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20040180891A1 (OSRAM) |
| EP (1) | EP1432689A1 (OSRAM) |
| JP (1) | JP2005504098A (OSRAM) |
| CA (1) | CA2461128A1 (OSRAM) |
| WO (1) | WO2003027074A1 (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200840566A (en) * | 2006-12-22 | 2008-10-16 | Esteve Labor Dr | Heterocyclyl-substituted-ethylamino-phenyl derivatives, their preparation and use as medicaments |
| CN104557711B (zh) * | 2014-12-26 | 2017-12-15 | 南通大学 | 含fts结构的吡唑肟类化合物的制备和应用 |
| CN116768797A (zh) * | 2022-03-16 | 2023-09-19 | 成都苑东生物制药股份有限公司 | 一种吡唑类衍生物、其制备方法及用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2526469A1 (de) * | 1975-06-13 | 1976-12-30 | Bayer Ag | 1-substituierte pyrazolderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4117145A (en) * | 1975-06-13 | 1978-09-26 | Bayer Aktiengesellschaft | 1-substituted pyrazoles |
| NL8201321A (nl) * | 1981-04-07 | 1982-11-01 | Bayer Ag | Werkwijze voor de behandeling van metastase en de groei van tumorcellen. |
| DE3312581A1 (de) * | 1983-04-08 | 1984-10-11 | Bayer Ag, 5090 Leverkusen | Verwendung von pyrazolonderivaten bei der bekaempfung des wachstums von tumorzellen und der metastasenbildung, arzneimittel hierfuer und verfahren zu deren herstellung |
-
2002
- 2002-09-20 WO PCT/US2002/029958 patent/WO2003027074A1/en not_active Ceased
- 2002-09-20 US US10/489,796 patent/US20040180891A1/en not_active Abandoned
- 2002-09-20 JP JP2003530665A patent/JP2005504098A/ja not_active Withdrawn
- 2002-09-20 CA CA002461128A patent/CA2461128A1/en not_active Abandoned
- 2002-09-20 EP EP02799600A patent/EP1432689A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP1432689A1 (en) | 2004-06-30 |
| US20040180891A1 (en) | 2004-09-16 |
| JP2005504098A (ja) | 2005-02-10 |
| WO2003027074A1 (en) | 2003-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |