NO314260B1 - Pyrazol-derivater og antitumormiddel - Google Patents

Pyrazol-derivater og antitumormiddel Download PDF

Info

Publication number: NO314260B1
Authority: NO; Norway
Prior art keywords: group; compound; methyl; nmr; added
Prior art date: 1997-01-27

Application number

NO19993628A

Other languages

English (en)

Norwegian (no)

Other versions

NO993628D0 (no

NO993628L (no

Inventor

Akio Ejima

Satoru Ohsuki

Original Assignee

Daiichi Seiyaku Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-01-27

Filing date

1999-07-26

Publication date

2003-02-24

1999-07-26 Application filed by Daiichi Seiyaku Co filed Critical Daiichi Seiyaku Co

1999-07-26 Publication of NO993628D0 publication Critical patent/NO993628D0/no

1999-09-22 Publication of NO993628L publication Critical patent/NO993628L/no

2003-02-24 Publication of NO314260B1 publication Critical patent/NO314260B1/no

Links

239000002246 antineoplastic agent Substances 0.000 title claims description 10
150000003217 pyrazoles Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 391
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 10
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000004306 triazinyl group Chemical group 0.000 claims description 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 166
239000000203 mixture Substances 0.000 description 138
239000000243 solution Substances 0.000 description 136
239000002904 solvent Substances 0.000 description 125
238000002360 preparation method Methods 0.000 description 123
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 99
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 98
238000005160 1H NMR spectroscopy Methods 0.000 description 96
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 82
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
239000011541 reaction mixture Substances 0.000 description 73
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 69
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
230000015572 biosynthetic process Effects 0.000 description 58
238000000354 decomposition reaction Methods 0.000 description 57
238000002844 melting Methods 0.000 description 57
230000008018 melting Effects 0.000 description 57
229920006395 saturated elastomer Polymers 0.000 description 57
238000003786 synthesis reaction Methods 0.000 description 55
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
238000001704 evaporation Methods 0.000 description 45
230000008020 evaporation Effects 0.000 description 45
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
238000005481 NMR spectroscopy Methods 0.000 description 42
239000011780 sodium chloride Substances 0.000 description 41
239000000047 product Substances 0.000 description 40
238000003756 stirring Methods 0.000 description 40
-1 lithium aluminum hydride Chemical compound 0.000 description 38
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 38
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 37
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 35
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
238000001914 filtration Methods 0.000 description 33
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 32
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 32
238000010992 reflux Methods 0.000 description 32
238000010898 silica gel chromatography Methods 0.000 description 32
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 26
239000012044 organic layer Substances 0.000 description 26
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
238000010438 heat treatment Methods 0.000 description 23
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 22
238000000034 method Methods 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 21
238000001816 cooling Methods 0.000 description 21
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 18
239000007864 aqueous solution Substances 0.000 description 18
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 18
NBELRSAJZMPNCR-UHFFFAOYSA-N 1-(3,5-difluorophenyl)piperazine;hydrochloride Chemical compound Cl.FC1=CC(F)=CC(N2CCNCC2)=C1 NBELRSAJZMPNCR-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
239000000706 filtrate Substances 0.000 description 16
229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
235000017557 sodium bicarbonate Nutrition 0.000 description 16
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 15
229910000027 potassium carbonate Inorganic materials 0.000 description 15
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
101150041968 CDC13 gene Proteins 0.000 description 13
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
150000002170 ethers Chemical class 0.000 description 11
239000012046 mixed solvent Substances 0.000 description 11
239000012299 nitrogen atmosphere Substances 0.000 description 11
238000006722 reduction reaction Methods 0.000 description 11
239000005909 Kieselgur Substances 0.000 description 10
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
150000007514 bases Chemical class 0.000 description 10
239000003638 chemical reducing agent Substances 0.000 description 10
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 10
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
239000012141 concentrate Substances 0.000 description 9
235000008504 concentrate Nutrition 0.000 description 9
230000018044 dehydration Effects 0.000 description 9
238000006297 dehydration reaction Methods 0.000 description 9
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 9
239000012279 sodium borohydride Substances 0.000 description 9
229910000033 sodium borohydride Inorganic materials 0.000 description 9
239000008096 xylene Substances 0.000 description 9
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 8
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 8
229960002949 fluorouracil Drugs 0.000 description 8
FIFOCEFOCMXMKA-UHFFFAOYSA-N 6-ethoxyhex-5-ene-2,4-dione Chemical compound CCOC=CC(=O)CC(C)=O FIFOCEFOCMXMKA-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 7
229930195733 hydrocarbon Natural products 0.000 description 7
150000002430 hydrocarbons Chemical class 0.000 description 7
150000007522 mineralic acids Chemical class 0.000 description 7
150000007524 organic acids Chemical class 0.000 description 7
235000005985 organic acids Nutrition 0.000 description 7
ZXSDBHQFJKRIEW-UHFFFAOYSA-N 1-[1-(3-chloropyridin-2-yl)-5-methylpyrazol-4-yl]ethanone Chemical compound CC1=C(C(=O)C)C=NN1C1=NC=CC=C1Cl ZXSDBHQFJKRIEW-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
230000000259 anti-tumor effect Effects 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
150000004885 piperazines Chemical class 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
238000006268 reductive amination reaction Methods 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
XAYCTBDPZIKHCW-UHFFFAOYSA-N (3-chloropyridin-2-yl)hydrazine Chemical group NNC1=NC=CC=C1Cl XAYCTBDPZIKHCW-UHFFFAOYSA-N 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000003814 drug Substances 0.000 description 5
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
150000008282 halocarbons Chemical class 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000007800 oxidant agent Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
GJASZYGGGRNXFT-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)piperazine;hydrochloride Chemical compound Cl.ClC1=CC(Cl)=CC(N2CCNCC2)=C1 GJASZYGGGRNXFT-UHFFFAOYSA-N 0.000 description 4
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
CCVNZKGBNUPYPG-UHFFFAOYSA-N 2-chloro-3-methoxypyridine Chemical compound COC1=CC=CN=C1Cl CCVNZKGBNUPYPG-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
239000002585 base Substances 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000013078 crystal Substances 0.000 description 4
229940043279 diisopropylamine Drugs 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
AVTYONGGKAJVTE-OLXYHTOASA-L potassium L-tartrate Chemical compound [K+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O AVTYONGGKAJVTE-OLXYHTOASA-L 0.000 description 4
239000001472 potassium tartrate Substances 0.000 description 4
229940111695 potassium tartrate Drugs 0.000 description 4
235000011005 potassium tartrates Nutrition 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
MHXPYWFZULXYHT-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazin-1-ium;chloride Chemical compound Cl.ClC1=CC=CC(N2CCNCC2)=C1 MHXPYWFZULXYHT-UHFFFAOYSA-N 0.000 description 3
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000007259 addition reaction Methods 0.000 description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
235000019445 benzyl alcohol Nutrition 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 3
LKUXUIDFIZIAIR-UHFFFAOYSA-N ethyl 2-(1,2,2-triphenylphospholan-3-ylidene)acetate Chemical compound C=1C=CC=CC=1C1(C=2C=CC=CC=2)C(=CC(=O)OCC)CCP1C1=CC=CC=C1 LKUXUIDFIZIAIR-UHFFFAOYSA-N 0.000 description 3
XDHWYQRLMSOZOP-UHFFFAOYSA-N ethyl 5-ethoxy-3-oxopent-4-enoate Chemical compound CCOC=CC(=O)CC(=O)OCC XDHWYQRLMSOZOP-UHFFFAOYSA-N 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
239000004533 oil dispersion Substances 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
150000004714 phosphonium salts Chemical class 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 3
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 3
GIOKIYJPVXGWME-UHFFFAOYSA-N 1-(5-methyl-1-pyridin-4-ylpyrazol-4-yl)ethanone Chemical compound CC1=C(C(=O)C)C=NN1C1=CC=NC=C1 GIOKIYJPVXGWME-UHFFFAOYSA-N 0.000 description 2
BYUALARVKBHBRF-UHFFFAOYSA-N 1-[5-methyl-1-(2,4,6-trichlorophenyl)pyrazol-4-yl]ethanone Chemical compound CC1=C(C(=O)C)C=NN1C1=C(Cl)C=C(Cl)C=C1Cl BYUALARVKBHBRF-UHFFFAOYSA-N 0.000 description 2
GGMDFPMASIXEIR-UHFFFAOYSA-N 1-bromo-3-chloro-5-fluorobenzene Chemical compound FC1=CC(Cl)=CC(Br)=C1 GGMDFPMASIXEIR-UHFFFAOYSA-N 0.000 description 2
BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 2
WAVYAFBQOXCGSZ-UHFFFAOYSA-N 2-fluoropyrimidine Chemical compound FC1=NC=CC=N1 WAVYAFBQOXCGSZ-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
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TXFLGZOGNOOEFZ-UHFFFAOYSA-N bis(2-chloroethyl)amine Chemical compound ClCCNCCCl TXFLGZOGNOOEFZ-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical group 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
NENALCQFBYSYCW-UHFFFAOYSA-N ethyl 1-(2-amino-6-phenylmethoxypyrimidin-4-yl)-5-methylpyrazole-4-carboxylate Chemical compound CC1=C(C(=O)OCC)C=NN1C1=CC(OCC=2C=CC=CC=2)=NC(N)=N1 NENALCQFBYSYCW-UHFFFAOYSA-N 0.000 description 1
JBPWPWJMFGSQNQ-UHFFFAOYSA-N ethyl 1-(2-chloropyrimidin-4-yl)-5-methylpyrazole-4-carboxylate Chemical compound CC1=C(C(=O)OCC)C=NN1C1=CC=NC(Cl)=N1 JBPWPWJMFGSQNQ-UHFFFAOYSA-N 0.000 description 1
NRYKUMQKKCIIKO-UHFFFAOYSA-N ethyl 5-methyl-1-(2-phenylmethoxypyrimidin-4-yl)pyrazole-4-carboxylate Chemical compound CC1=C(C(=O)OCC)C=NN1C1=CC=NC(OCC=2C=CC=CC=2)=N1 NRYKUMQKKCIIKO-UHFFFAOYSA-N 0.000 description 1
JNCVSCNGGNXMFI-UHFFFAOYSA-N ethyl 5-methyl-1-(4-phenylmethoxypyrimidin-2-yl)pyrazole-4-carboxylate Chemical compound CC1=C(C(=O)OCC)C=NN1C1=NC=CC(OCC=2C=CC=CC=2)=N1 JNCVSCNGGNXMFI-UHFFFAOYSA-N 0.000 description 1
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012091 fetal bovine serum Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
230000014509 gene expression Effects 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical compound OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 description 1
229960002064 kanamycin sulfate Drugs 0.000 description 1
VCPPTNDHEILJHD-UHFFFAOYSA-N lithium;prop-1-ene Chemical compound [Li+].[CH2-]C=C VCPPTNDHEILJHD-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical group COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
CPZBTYRIGVOOMI-UHFFFAOYSA-N methylsulfanyl(methylsulfanylmethoxy)methane Chemical group CSCOCSC CPZBTYRIGVOOMI-UHFFFAOYSA-N 0.000 description 1
230000017095 negative regulation of cell growth Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
OTYPIDNRISCWQY-UHFFFAOYSA-L palladium(2+);tris(2-methylphenyl)phosphane;dichloride Chemical compound Cl[Pd]Cl.CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C.CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C OTYPIDNRISCWQY-UHFFFAOYSA-L 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
TYZYRCHEVXXLSJ-UHFFFAOYSA-N phenylmethoxymethoxymethoxymethylbenzene Chemical group C=1C=CC=CC=1COCOCOCC1=CC=CC=C1 TYZYRCHEVXXLSJ-UHFFFAOYSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
WLHPCEJPGLYEJZ-UHFFFAOYSA-N prop-2-enyltin Chemical compound [Sn]CC=C WLHPCEJPGLYEJZ-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
229910001488 sodium perchlorate Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
230000006103 sulfonylation Effects 0.000 description 1
238000005694 sulfonylation reaction Methods 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
CPHKHDBHFJNODM-UHFFFAOYSA-N tert-butyl n-[(3-fluoro-5-piperazin-1-ylphenyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC(F)=CC(N2CCNCC2)=C1 CPHKHDBHFJNODM-UHFFFAOYSA-N 0.000 description 1
AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- 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
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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)

NO19993628A 1997-01-27 1999-07-26 Pyrazol-derivater og antitumormiddel NO314260B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP1211697		1997-01-27
PCT/JP1998/000300 WO1998032739A1 (en)	1997-01-27	1998-01-26	Pyrazole derivatives

Publications (3)

Publication Number	Publication Date
NO993628D0 NO993628D0 (no)	1999-07-26
NO993628L NO993628L (no)	1999-09-22
NO314260B1 true NO314260B1 (no)	2003-02-24

Family

ID=11796592

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19993628A NO314260B1 (no)	1997-01-27	1999-07-26	Pyrazol-derivater og antitumormiddel

Country Status (10)

Country	Link
EP (1)	EP1022270A4 (id)
KR (1)	KR20000070523A (id)
CN (1)	CN1105707C (id)
AU (1)	AU724394B2 (id)
CA (1)	CA2278677A1 (id)
EA (1)	EA002101B1 (id)
ID (1)	ID22017A (id)
NO (1)	NO314260B1 (id)
TW (1)	TW486478B (id)
WO (1)	WO1998032739A1 (id)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6169086B1 (en)	1997-01-27	2001-01-02	Daiichi Pharmaceutical Co., Ltd.	Pyrazole derivatives
AU4800299A (en) *	1998-07-24	2000-02-14	Daiichi Pharmaceutical Co., Ltd.	Pyrazole derivatives and salts thereof
EP2266973A1 (de)	2009-05-29	2010-12-29	Bayer CropScience AG	Pyrazinylpyrazole
AR078947A1 (es)	2009-11-11	2011-12-14	Bayer Cropscience Ag	Compuestos de diazinil-pirazolilo y procesos de preparacion de los mismos
MX2012005332A (es) *	2009-11-13	2012-10-15	Oscotec Inc	Inhibidores de cinasa.
DK3395801T3 (da)	2015-12-16	2021-05-10	Nippon Soda Co	Arylazolforbindelse og skadedyrsbekæmpelsesmiddel
TW202120478A (zh) *	2019-11-22	2021-06-01	美商富曼西公司	用於合成(3-氯-2-吡啶基)肼的新穎製程

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1510315A (fr) *	1966-02-03	1968-01-19	Ciba Geigy	Procédé pour la préparation de 4-diaza-cyclo-alcano-pyrazoles substitués en position 1 par des restes hétérocycliques bicycliques
JPS61129129A (ja) *	1984-11-28	1986-06-17	Kureha Chem Ind Co Ltd	抗腫瘍剤
EP0241053B1 (en) *	1986-02-27	1992-11-11	Duphar International Research B.V	Aryl-substituted (n-piperidinyl)-methyl- and (n-piperazinyl) methylazoles having antipsychotic properties
US4808621A (en) *	1986-07-07	1989-02-28	Warner-Lambert Company	Trans-6-[2-(N-heteroaryl-3,5-disubstituted)pyrazol-4-yl)-ethyl]- or ethenyl]tetrahydro-4-hydroxypyran-2-one inhibitors of cholesterol biosynthesis
TW312694B (id) *	1994-09-26	1997-08-11	Daiichi Seiyaku Co

1998
- 1998-01-26 CA CA002278677A patent/CA2278677A1/en not_active Abandoned
- 1998-01-26 EP EP98900736A patent/EP1022270A4/en not_active Withdrawn
- 1998-01-26 AU AU55771/98A patent/AU724394B2/en not_active Ceased
- 1998-01-26 KR KR1019997006768A patent/KR20000070523A/ko not_active Withdrawn
- 1998-01-26 EA EA199900600A patent/EA002101B1/ru not_active IP Right Cessation
- 1998-01-26 WO PCT/JP1998/000300 patent/WO1998032739A1/ja not_active Ceased
- 1998-01-26 TW TW087101177A patent/TW486478B/zh active
- 1998-01-26 ID IDW990743A patent/ID22017A/id unknown
- 1998-01-26 CN CN98803733A patent/CN1105707C/zh not_active Expired - Fee Related
1999
- 1999-07-26 NO NO19993628A patent/NO314260B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
CA2278677A1 (en)	1998-07-30
CN1105707C (zh)	2003-04-16
EP1022270A4 (en)	2002-01-30
NO993628D0 (no)	1999-07-26
EP1022270A1 (en)	2000-07-26
ID22017A (id)	1999-08-26
EA002101B1 (ru)	2001-12-24
EA199900600A1 (ru)	2000-04-24
WO1998032739A1 (en)	1998-07-30
AU5577198A (en)	1998-08-18
CN1251578A (zh)	2000-04-26
AU724394B2 (en)	2000-09-21
KR20000070523A (ko)	2000-11-25
TW486478B (en)	2002-05-11
NO993628L (no)	1999-09-22

Legal Events

Date	Code	Title	Description
2005-09-26	MM1K	Lapsed by not paying the annual fees

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KR100848067B1 (ko)	2008-07-23	아미드 유도체 및 의약
US6552018B1 (en)	2003-04-22	Pyrazole derivatives
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CA2547080A1 (en)	2005-07-28	Heterocyclic protein kinase inhibitors and uses thereof
NZ238624A (en)	1994-08-26	Pyridine derivatives, compositions, preparations and use thereof
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UA71535C2 (en)	2004-12-15	Corticotropine-releasing antagonists factor, methods for the preparation thereof, pharmaceuitical composition and a method for the treatment
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AU2005300733A1 (en)	2006-05-11	Novel anthranilamide pyridinureas as VEGF receptor kinase inhibitors
TW321639B (id)	1997-12-01
SK107797A3 (en)	1998-08-05	2,6-disubstituted pyridines and 2,4-disubstituted pyrimidines and use thereof, herbicidal agents and methods for inhibiting plants growth
NO314260B1 (no)	2003-02-24	Pyrazol-derivater og antitumormiddel
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EP1807416B1 (en)	2012-08-29	Nicotinamide pyridinureas as vascular endothelial growth factor (VEGF) receptor kinase inhibitors
Naito et al.	2005	Synthesis and antitumor activity of novel pyrimidinyl pyrazole derivatives. III. Synthesis and antitumor activity of 3-phenylpiperazinyl-1-trans-propenes
AU2004200420A1 (en)	2004-09-30	Inhibitor of cyclooxygenase
RU2261862C2 (ru)	2005-10-10	Замещенные пирролы
HK1027104A (en)	2001-01-05	Pyrazole derivatives
WO2015197188A1 (en)	2015-12-30	Pyrazolyl-based carboxamides as crac inhibitors