IL124801A - History of pyrazole, their preparation and pharmaceutical preparations containing them - Google Patents

History of pyrazole, their preparation and pharmaceutical preparations containing them

Info

Publication number: IL124801A
Authority: IL; Israel
Prior art keywords: formula; compound; compounds; hydrogen; preparation
Prior art date: 1995-12-08

Application number

IL12480196A

Other languages

English (en)

Hebrew (he)

Other versions

IL124801A0 (en

Original Assignee

Sanofi Synthelabo

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.)

1995-12-08

Filing date

1996-12-06

Publication date

2004-07-25

1996-12-06 Application filed by Sanofi Synthelabo filed Critical Sanofi Synthelabo

1999-01-26 Publication of IL124801A0 publication Critical patent/IL124801A0/xx

2004-07-25 Publication of IL124801A publication Critical patent/IL124801A/en

Links

238000002360 preparation method Methods 0.000 title claims description 216
239000008194 pharmaceutical composition Substances 0.000 title claims description 10
150000003217 pyrazoles Chemical class 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims abstract description 510
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 88
239000001257 hydrogen Substances 0.000 claims abstract description 88
150000003839 salts Chemical class 0.000 claims abstract description 58
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 33
150000002431 hydrogen Chemical class 0.000 claims abstract description 29
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 26
125000005843 halogen group Chemical group 0.000 claims abstract description 24
125000003545 alkoxy group Chemical group 0.000 claims abstract description 20
229910052731 fluorine Inorganic materials 0.000 claims abstract description 18
125000001424 substituent group Chemical group 0.000 claims abstract description 18
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 8
239000011737 fluorine Substances 0.000 claims abstract description 6
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 4
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 3
239000005977 Ethylene Substances 0.000 claims abstract description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 219
238000000034 method Methods 0.000 claims description 137
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 113
239000002904 solvent Substances 0.000 claims description 92
KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 claims description 86
125000000217 alkyl group Chemical group 0.000 claims description 49
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
230000008569 process Effects 0.000 claims description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
238000010992 reflux Methods 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 14
102000009135 CB2 Cannabinoid Receptor Human genes 0.000 claims description 13
108010073376 CB2 Cannabinoid Receptor Proteins 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
101100229907 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) GPP2 gene Proteins 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 2
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
230000000144 pharmacologic effect Effects 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
125000006715 (C1-C5) alkylthio group Chemical group 0.000 abstract 1
239000000243 solution Substances 0.000 description 207
239000000047 product Substances 0.000 description 179
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 138
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 138
239000000203 mixture Substances 0.000 description 134
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 132
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 117
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 114
229910001868 water Inorganic materials 0.000 description 112
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 100
239000011541 reaction mixture Substances 0.000 description 100
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 92
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
239000012074 organic phase Substances 0.000 description 63
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 53
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 46
239000003480 eluent Substances 0.000 description 45
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 44
239000002244 precipitate Substances 0.000 description 44
239000000377 silicon dioxide Substances 0.000 description 42
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 40
229910000104 sodium hydride Inorganic materials 0.000 description 38
238000005481 NMR spectroscopy Methods 0.000 description 36
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 36
-1 carbocyclic radical Chemical class 0.000 description 36
239000012312 sodium hydride Substances 0.000 description 36
239000006185 dispersion Substances 0.000 description 34
229920006395 saturated elastomer Polymers 0.000 description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
238000001816 cooling Methods 0.000 description 31
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical class NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
239000000706 filtrate Substances 0.000 description 26
229910052943 magnesium sulfate Inorganic materials 0.000 description 22
239000000725 suspension Substances 0.000 description 21
229910052801 chlorine Inorganic materials 0.000 description 18
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 18
239000002198 insoluble material Substances 0.000 description 18
239000007853 buffer solution Substances 0.000 description 17
229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 16
230000000694 effects Effects 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
125000001309 chloro group Chemical group Cl* 0.000 description 15
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 14
239000011734 sodium Substances 0.000 description 14
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
125000001153 fluoro group Chemical group F* 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 11
238000004128 high performance liquid chromatography Methods 0.000 description 10
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
102000018208 Cannabinoid Receptor Human genes 0.000 description 9
108050007331 Cannabinoid receptor Proteins 0.000 description 9
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
159000000000 sodium salts Chemical class 0.000 description 9
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
150000008064 anhydrides Chemical class 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
238000010908 decantation Methods 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
239000003826 tablet Substances 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 7
229940121376 cannabinoid receptor agonist Drugs 0.000 description 7
239000003537 cannabinoid receptor agonist Substances 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
238000003756 stirring Methods 0.000 description 7
IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 description 6
YNZFFALZMRAPHQ-SYYKKAFVSA-N 2-[(1r,2r,5r)-5-hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC=C1[C@H]1[C@H](CCCO)CC[C@@H](O)C1 YNZFFALZMRAPHQ-SYYKKAFVSA-N 0.000 description 6
PXEODPDCEHMCKE-UHFFFAOYSA-N 2-chloro-4-(iodomethyl)-1-methylbenzene Chemical compound CC1=CC=C(CI)C=C1Cl PXEODPDCEHMCKE-UHFFFAOYSA-N 0.000 description 6
XLWSBDFQAJXCQX-UHFFFAOYSA-N 4-(bromomethyl)-1,2-dichlorobenzene Chemical compound ClC1=CC=C(CBr)C=C1Cl XLWSBDFQAJXCQX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HQVHOQAKMCMIIM-HXUWFJFHSA-N WIN 55212-2 Chemical compound C([C@@H]1COC=2C=CC=C3C(C(=O)C=4C5=CC=CC=C5C=CC=4)=C(N1C3=2)C)N1CCOCC1 HQVHOQAKMCMIIM-HXUWFJFHSA-N 0.000 description 6
RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
239000007903 gelatin capsule Substances 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
229920000858 Cyclodextrin Polymers 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
239000001828 Gelatine Substances 0.000 description 5
235000019445 benzyl alcohol Nutrition 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
238000001035 drying Methods 0.000 description 5
229920000159 gelatin Polymers 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
229960001021 lactose monohydrate Drugs 0.000 description 5
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
235000019400 benzoyl peroxide Nutrition 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
WZRKSPFYXUXINF-UHFFFAOYSA-N 1-(bromomethyl)-4-methylbenzene Chemical compound CC1=CC=C(CBr)C=C1 WZRKSPFYXUXINF-UHFFFAOYSA-N 0.000 description 3
HUAAXEGWVZBZHR-UHFFFAOYSA-N 2,2,6,6-tetramethylcyclohexan-1-amine Chemical compound CC1(C)CCCC(C)(C)C1N HUAAXEGWVZBZHR-UHFFFAOYSA-N 0.000 description 3
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 3
JTMYLQKKQFLIGV-UHFFFAOYSA-N 2-chloro-4-(chloromethyl)-1-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1Cl JTMYLQKKQFLIGV-UHFFFAOYSA-N 0.000 description 3
OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
OCJBMQKQAOSSKM-UHFFFAOYSA-N 4-(bromomethyl)-1H-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1CBr OCJBMQKQAOSSKM-UHFFFAOYSA-N 0.000 description 3
YOACSNDETIDTAY-UHFFFAOYSA-N 4-(bromomethyl)-2-fluoro-1-methylbenzene Chemical compound CC1=CC=C(CBr)C=C1F YOACSNDETIDTAY-UHFFFAOYSA-N 0.000 description 3
101710187022 Cannabinoid receptor 2 Proteins 0.000 description 3
102100036214 Cannabinoid receptor 2 Human genes 0.000 description 3
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
102000043136 MAP kinase family Human genes 0.000 description 3
108091054455 MAP kinase family Proteins 0.000 description 3
108700012920 TNF Proteins 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
210000003719 b-lymphocyte Anatomy 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
229930003827 cannabinoid Natural products 0.000 description 3
239000003557 cannabinoid Substances 0.000 description 3
229940065144 cannabinoids Drugs 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
208000026278 immune system disease Diseases 0.000 description 3
229910003002 lithium salt Inorganic materials 0.000 description 3
159000000002 lithium salts Chemical class 0.000 description 3
QXUAFCKBYYPTPQ-ZWKAXHIPSA-L magnesium (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol octadecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O QXUAFCKBYYPTPQ-ZWKAXHIPSA-L 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
230000020477 pH reduction Effects 0.000 description 3
230000002093 peripheral effect Effects 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000002953 preparative HPLC Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
YYPPFEKHXPADAV-UHFFFAOYSA-N 1-(bromomethyl)-4-ethylbenzene Chemical compound CCC1=CC=C(CBr)C=C1 YYPPFEKHXPADAV-UHFFFAOYSA-N 0.000 description 2
NRZFKWDTQAFBBL-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-5-(2,6-dimethoxyphenyl)pyrazole-3-carboxylic acid Chemical compound COC1=CC=CC(OC)=C1C1=CC(C(O)=O)=NN1CC1=CC=C(Cl)C(Cl)=C1 NRZFKWDTQAFBBL-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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XXAHBQYWMMITFM-UHFFFAOYSA-N ethyl 3-fluoro-4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C(F)=C1 XXAHBQYWMMITFM-UHFFFAOYSA-N 0.000 description 1
POONIPCNSXVRNZ-UHFFFAOYSA-N ethyl 4-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxobut-3-enoate Chemical compound CCOC(=O)C(=O)C=C(O)C1=C(OC)C=CC=C1OC POONIPCNSXVRNZ-UHFFFAOYSA-N 0.000 description 1
KGRRAUCYPWOHCM-UHFFFAOYSA-N ethyl 4-(4-chloro-3-methylphenyl)-4-hydroxy-3-methyl-2-oxobut-3-enoate Chemical compound CCOC(=O)C(=O)C(C)=C(O)C1=CC=C(Cl)C(C)=C1 KGRRAUCYPWOHCM-UHFFFAOYSA-N 0.000 description 1
HIPIEFZTQUDKFS-UHFFFAOYSA-N ethyl 4-(4-chlorophenyl)-4-hydroxy-3-methyl-2-oxobut-3-enoate Chemical compound CCOC(=O)C(=O)C(C)=C(O)C1=CC=C(Cl)C=C1 HIPIEFZTQUDKFS-UHFFFAOYSA-N 0.000 description 1
DLMQAKHHSDBLEB-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)-1-[(3,4-dichlorophenyl)methyl]-4-methylpyrazole-3-carboxylate Chemical compound C=1C=C(Cl)C=CC=1C1=C(C)C(C(=O)OCC)=NN1CC1=CC=C(Cl)C(Cl)=C1 DLMQAKHHSDBLEB-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
210000002557 fixed macrophage Anatomy 0.000 description 1
239000012458 free base Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
229940080345 gamma-cyclodextrin Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
210000005095 gastrointestinal system Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
230000036541 health Effects 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
230000002519 immonomodulatory effect Effects 0.000 description 1
230000036737 immune function Effects 0.000 description 1
239000002955 immunomodulating agent Substances 0.000 description 1
229940121354 immunomodulator Drugs 0.000 description 1
230000001861 immunosuppressant effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000002372 labelling Methods 0.000 description 1
229960001375 lactose Drugs 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000000998 lymphohematopoietic effect Effects 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
230000002979 macrophagic effect Effects 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910001512 metal fluoride Inorganic materials 0.000 description 1
YGSXTWBSZQOARZ-UHFFFAOYSA-N methyl 1-[(2,4-dichlorophenyl)methyl]-5-(4-methylsulfanylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(Cl)C=C(Cl)C=1CN1N=C(C(=O)OC)C=C1C1=CC=C(SC)C=C1 YGSXTWBSZQOARZ-UHFFFAOYSA-N 0.000 description 1
XTHSCMYJSXLPHX-UHFFFAOYSA-N methyl 1-[(3-chloro-4-methylphenyl)methyl]-5-(3,4-dichlorophenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(C)C(Cl)=CC=1CN1N=C(C(=O)OC)C=C1C1=CC=C(Cl)C(Cl)=C1 XTHSCMYJSXLPHX-UHFFFAOYSA-N 0.000 description 1
ANMFGNQUYANPFL-UHFFFAOYSA-N methyl 1-[(3-chloro-4-methylphenyl)methyl]-5-(4-methylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(C)C(Cl)=CC=1CN1N=C(C(=O)OC)C=C1C1=CC=C(C)C=C1 ANMFGNQUYANPFL-UHFFFAOYSA-N 0.000 description 1
KKPGEGDSZHXWIC-UHFFFAOYSA-N methyl 1-[1-(3,4-dichlorophenyl)ethyl]-5-(4-methylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)N1N=C(C(=O)OC)C=C1C1=CC=C(C)C=C1 KKPGEGDSZHXWIC-UHFFFAOYSA-N 0.000 description 1
PXBTYSDXMSWQOU-UHFFFAOYSA-N methyl 3-(2,6-dimethoxyphenyl)-1h-pyrazole-5-carboxylate Chemical compound N1N=C(C(=O)OC)C=C1C1=C(OC)C=CC=C1OC PXBTYSDXMSWQOU-UHFFFAOYSA-N 0.000 description 1
KINFFVOVDYZUSF-UHFFFAOYSA-N methyl 3-(3,4-dichlorophenyl)-1h-pyrazole-5-carboxylate Chemical compound N1C(C(=O)OC)=CC(C=2C=C(Cl)C(Cl)=CC=2)=N1 KINFFVOVDYZUSF-UHFFFAOYSA-N 0.000 description 1
KKTZMJBNTHXASE-UHFFFAOYSA-N methyl 3-(3,4-dimethylphenyl)-1h-pyrazole-5-carboxylate Chemical compound N1N=C(C(=O)OC)C=C1C1=CC=C(C)C(C)=C1 KKTZMJBNTHXASE-UHFFFAOYSA-N 0.000 description 1
AWYAGOWXRPDDJE-UHFFFAOYSA-N methyl 3-(4-chloro-3-methylphenyl)-1h-pyrazole-5-carboxylate Chemical compound N1N=C(C(=O)OC)C=C1C1=CC=C(Cl)C(C)=C1 AWYAGOWXRPDDJE-UHFFFAOYSA-N 0.000 description 1
CJTXOTLTFMCCSV-UHFFFAOYSA-N methyl 3-(4-chlorophenyl)-1h-pyrazole-5-carboxylate Chemical compound N1C(C(=O)OC)=CC(C=2C=CC(Cl)=CC=2)=N1 CJTXOTLTFMCCSV-UHFFFAOYSA-N 0.000 description 1
SJAHLWMIVWUWKH-UHFFFAOYSA-N methyl 3-(4-fluorophenyl)-1h-pyrazole-5-carboxylate Chemical compound N1C(C(=O)OC)=CC(C=2C=CC(F)=CC=2)=N1 SJAHLWMIVWUWKH-UHFFFAOYSA-N 0.000 description 1
FJNMXQMHEIWMQI-UHFFFAOYSA-N methyl 3-(4-methoxyphenyl)-1h-pyrazole-5-carboxylate Chemical compound N1C(C(=O)OC)=CC(C=2C=CC(OC)=CC=2)=N1 FJNMXQMHEIWMQI-UHFFFAOYSA-N 0.000 description 1
QQBASWCUEOBWNQ-UHFFFAOYSA-N methyl 3-(4-methylphenyl)-1h-pyrazole-5-carboxylate Chemical compound N1C(C(=O)OC)=CC(C=2C=CC(C)=CC=2)=N1 QQBASWCUEOBWNQ-UHFFFAOYSA-N 0.000 description 1
VOVLXKYJEYNZPH-UHFFFAOYSA-N methyl 3-(4-methylsulfanylphenyl)-1h-pyrazole-5-carboxylate Chemical compound N1C(C(=O)OC)=CC(C=2C=CC(SC)=CC=2)=N1 VOVLXKYJEYNZPH-UHFFFAOYSA-N 0.000 description 1
BNSJOULIOYICPD-UHFFFAOYSA-N methyl 3-[4-(trifluoromethyl)phenyl]-1h-pyrazole-5-carboxylate Chemical compound N1N=C(C(=O)OC)C=C1C1=CC=C(C(F)(F)F)C=C1 BNSJOULIOYICPD-UHFFFAOYSA-N 0.000 description 1
ZOXOYEYLQJMYGC-UHFFFAOYSA-N methyl 4-(3,4-dichlorophenyl)-4-hydroxy-2-oxobut-3-enoate Chemical compound COC(=O)C(=O)C=C(O)C1=CC=C(Cl)C(Cl)=C1 ZOXOYEYLQJMYGC-UHFFFAOYSA-N 0.000 description 1
FWCHRTKJOLAJDE-UHFFFAOYSA-N methyl 4-(3,4-dimethylphenyl)-4-hydroxy-2-oxobut-3-enoate Chemical compound COC(=O)C(=O)C=C(O)C1=CC=C(C)C(C)=C1 FWCHRTKJOLAJDE-UHFFFAOYSA-N 0.000 description 1
SWCPGOROHFKDSO-UHFFFAOYSA-N methyl 4-(4-chloro-3-methylphenyl)-4-hydroxy-2-oxobut-3-enoate Chemical compound COC(=O)C(=O)C=C(O)C1=CC=C(Cl)C(C)=C1 SWCPGOROHFKDSO-UHFFFAOYSA-N 0.000 description 1
MZFJPAFGPHWXGR-UHFFFAOYSA-N methyl 4-(4-chlorophenyl)-4-hydroxy-2-oxobut-3-enoate Chemical compound COC(=O)C(=O)C=C(O)C1=CC=C(Cl)C=C1 MZFJPAFGPHWXGR-UHFFFAOYSA-N 0.000 description 1
KTWGXTGODIPYSX-UHFFFAOYSA-N methyl 4-(4-fluorophenyl)-4-hydroxy-2-oxobut-3-enoate Chemical compound COC(=O)C(=O)C=C(O)C1=CC=C(F)C=C1 KTWGXTGODIPYSX-UHFFFAOYSA-N 0.000 description 1
UYDHXRMQNDFZMY-UHFFFAOYSA-N methyl 4-hydroxy-2-oxo-4-[4-(trifluoromethyl)phenyl]but-3-enoate Chemical compound COC(=O)C(=O)C=C(O)C1=CC=C(C(F)(F)F)C=C1 UYDHXRMQNDFZMY-UHFFFAOYSA-N 0.000 description 1
WZWQAWMZYSJXRA-UHFFFAOYSA-N methyl 4-hydroxy-4-(4-methoxyphenyl)-2-oxobut-3-enoate Chemical compound COC(=O)C(=O)C=C(O)C1=CC=C(OC)C=C1 WZWQAWMZYSJXRA-UHFFFAOYSA-N 0.000 description 1
KAQIFZRTEIWJID-UHFFFAOYSA-N methyl 4-hydroxy-4-(4-methylphenyl)-2-oxobut-3-enoate Chemical compound COC(=O)C(=O)C=C(O)C1=CC=C(C)C=C1 KAQIFZRTEIWJID-UHFFFAOYSA-N 0.000 description 1
REVBPHYEYKCCSO-UHFFFAOYSA-N methyl 4-hydroxy-4-(4-methylsulfanylphenyl)-2-oxobut-3-enoate Chemical compound COC(=O)C(=O)C=C(O)C1=CC=C(SC)C=C1 REVBPHYEYKCCSO-UHFFFAOYSA-N 0.000 description 1
GMSZPSDOTVLJNC-UHFFFAOYSA-N methyl 5-(3,4-dichlorophenyl)-1-(4-methylphenyl)pyrazole-3-carboxylate Chemical compound C=1C=C(C)C=CC=1N1N=C(C(=O)OC)C=C1C1=CC=C(Cl)C(Cl)=C1 GMSZPSDOTVLJNC-UHFFFAOYSA-N 0.000 description 1
VZIBVGNWRRETHX-UHFFFAOYSA-N methyl 5-(4-chloro-3-methylphenyl)-1-[(2,4-dichlorophenyl)methyl]pyrazole-3-carboxylate Chemical compound C=1C=C(Cl)C=C(Cl)C=1CN1N=C(C(=O)OC)C=C1C1=CC=C(Cl)C(C)=C1 VZIBVGNWRRETHX-UHFFFAOYSA-N 0.000 description 1
FYJWJFIQUGFRQF-UHFFFAOYSA-N methyl 5-(4-chloro-3-methylphenyl)-1-[(4-ethylphenyl)methyl]pyrazole-3-carboxylate Chemical compound C1=CC(CC)=CC=C1CN1C(C=2C=C(C)C(Cl)=CC=2)=CC(C(=O)OC)=N1 FYJWJFIQUGFRQF-UHFFFAOYSA-N 0.000 description 1
WGCGWTCMMMRRFJ-UHFFFAOYSA-N methyl 5-(4-chloro-3-methylphenyl)-1-[(4-methoxyphenyl)methyl]pyrazole-3-carboxylate Chemical compound C=1C=C(OC)C=CC=1CN1N=C(C(=O)OC)C=C1C1=CC=C(Cl)C(C)=C1 WGCGWTCMMMRRFJ-UHFFFAOYSA-N 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
150000005172 methylbenzenes Chemical class 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
230000003641 microbiacidal effect Effects 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
239000003226 mitogen Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
RZWWYFLNOJPCNO-UHFFFAOYSA-N n-(2,2,6,6-tetramethylcyclohexylidene)hydroxylamine Chemical compound CC1(C)CCCC(C)(C)C1=NO RZWWYFLNOJPCNO-UHFFFAOYSA-N 0.000 description 1
RPFMGCRMNJQDOS-UHFFFAOYSA-N n-(propylideneamino)propan-1-imine Chemical compound CCC=NN=CCC RPFMGCRMNJQDOS-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
VXGGWVBRICYCGO-UHFFFAOYSA-N n-ethyladamantan-1-amine Chemical compound C1C(C2)CC3CC2CC1(NCC)C3 VXGGWVBRICYCGO-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
125000005485 noradamantyl group Chemical group 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000003199 nucleic acid amplification method Methods 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
ZHVULPDNOFUIML-UHFFFAOYSA-N octane;hydrochloride Chemical compound Cl.CCCCCCCC ZHVULPDNOFUIML-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000007170 pathology Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000009696 proliferative response Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
208000002574 reactive arthritis Diseases 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
201000000596 systemic lupus erythematosus Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
PCZOZSATUTWXIC-UHFFFAOYSA-N tetraethylazanium;cyanide Chemical compound N#[C-].CC[N+](CC)(CC)CC PCZOZSATUTWXIC-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
230000003442 weekly effect Effects 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
- C07D231/14—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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

IL12480196A 1995-12-08 1996-12-06 History of pyrazole, their preparation and pharmaceutical preparations containing them IL124801A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9514547A FR2742148B1 (fr)	1995-12-08	1995-12-08	Nouveaux derives du pyrazole-3-carboxamide, procede pour leur preparation et compositions pharmaceutiques les contenant
PCT/FR1996/001953 WO1997021682A1 (fr)	1995-12-08	1996-12-06	Derives de 3-pyrazolecarboxamide avec une affinite pour le recepteur des cannabinoides

Publications (2)

Publication Number	Publication Date
IL124801A0 IL124801A0 (en)	1999-01-26
IL124801A true IL124801A (en)	2004-07-25

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ID=9485291

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12480196A IL124801A (en)	1995-12-08	1996-12-06	History of pyrazole, their preparation and pharmaceutical preparations containing them

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US (1)	US5925768A (is)
EP (2)	EP0868420B1 (is)
JP (1)	JP3510270B2 (is)
KR (1)	KR100488610B1 (is)
CN (1)	CN1101813C (is)
AR (1)	AR004364A1 (is)
AT (1)	ATE191211T1 (is)
AU (1)	AU718763B2 (is)
BR (1)	BR9611986A (is)
CA (1)	CA2239489C (is)
CZ (1)	CZ294307B6 (is)
DE (1)	DE69607484T2 (is)
DK (1)	DK0868420T3 (is)
EE (1)	EE04674B1 (is)
ES (1)	ES2148820T3 (is)
FR (1)	FR2742148B1 (is)
GR (1)	GR3033626T3 (is)
HU (1)	HUP9901244A3 (is)
IL (1)	IL124801A (is)
IS (1)	IS4765A (is)
MX (1)	MX9804565A (is)
MY (1)	MY115228A (is)
NO (1)	NO310683B1 (is)
NZ (1)	NZ323962A (is)
PL (1)	PL186466B1 (is)
PT (1)	PT868420E (is)
RU (1)	RU2170230C2 (is)
SI (1)	SI0868420T1 (is)
SK (1)	SK283706B6 (is)
TR (1)	TR199801041T2 (is)
TW (1)	TW402594B (is)
UA (1)	UA44913C2 (is)
WO (1)	WO1997021682A1 (is)
ZA (1)	ZA9610299B (is)

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1995
- 1995-12-08 FR FR9514547A patent/FR2742148B1/fr not_active Expired - Fee Related
1996
- 1996-12-06 WO PCT/FR1996/001953 patent/WO1997021682A1/fr not_active Ceased
- 1996-12-06 CZ CZ19981775A patent/CZ294307B6/cs not_active IP Right Cessation
- 1996-12-06 UA UA98062944A patent/UA44913C2/uk unknown
- 1996-12-06 NZ NZ323962A patent/NZ323962A/xx not_active IP Right Cessation
- 1996-12-06 AU AU11010/97A patent/AU718763B2/en not_active Ceased
- 1996-12-06 RU RU98112606/04A patent/RU2170230C2/ru not_active IP Right Cessation
- 1996-12-06 SK SK758-98A patent/SK283706B6/sk not_active IP Right Cessation
- 1996-12-06 HU HU9901244A patent/HUP9901244A3/hu unknown
- 1996-12-06 CA CA002239489A patent/CA2239489C/en not_active Expired - Fee Related
- 1996-12-06 DE DE69607484T patent/DE69607484T2/de not_active Expired - Lifetime
- 1996-12-06 CN CN96199643A patent/CN1101813C/zh not_active Expired - Fee Related
- 1996-12-06 EP EP96941716A patent/EP0868420B1/fr not_active Expired - Lifetime
- 1996-12-06 AR ARP960105525A patent/AR004364A1/es active IP Right Grant
- 1996-12-06 ZA ZA9610299A patent/ZA9610299B/xx unknown
- 1996-12-06 PL PL96327177A patent/PL186466B1/pl not_active IP Right Cessation
- 1996-12-06 PT PT96941716T patent/PT868420E/pt unknown
- 1996-12-06 TR TR1998/01041T patent/TR199801041T2/xx unknown
- 1996-12-06 JP JP52178697A patent/JP3510270B2/ja not_active Expired - Fee Related
- 1996-12-06 KR KR10-1998-0704296A patent/KR100488610B1/ko not_active Expired - Fee Related
- 1996-12-06 SI SI9630209T patent/SI0868420T1/xx unknown
- 1996-12-06 EE EE9800171A patent/EE04674B1/xx not_active IP Right Cessation
- 1996-12-06 IL IL12480196A patent/IL124801A/en not_active IP Right Cessation
- 1996-12-06 EP EP98401565A patent/EP0885889A3/fr not_active Withdrawn
- 1996-12-06 US US09/077,767 patent/US5925768A/en not_active Expired - Lifetime
- 1996-12-06 AT AT96941716T patent/ATE191211T1/de not_active IP Right Cessation
- 1996-12-06 ES ES96941716T patent/ES2148820T3/es not_active Expired - Lifetime
- 1996-12-06 BR BR9611986A patent/BR9611986A/pt not_active IP Right Cessation
- 1996-12-06 DK DK96941716T patent/DK0868420T3/da active
- 1996-12-07 TW TW085115150A patent/TW402594B/zh active
- 1996-12-07 MY MYPI96005160A patent/MY115228A/en unknown
1998
- 1998-06-05 NO NO19982589A patent/NO310683B1/no not_active IP Right Cessation
- 1998-06-08 MX MX9804565A patent/MX9804565A/es not_active IP Right Cessation
- 1998-06-08 IS IS4765A patent/IS4765A/is unknown
2000
- 2000-06-07 GR GR20000401312T patent/GR3033626T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
CN1207731A (zh)	1999-02-10
WO1997021682A1 (fr)	1997-06-19
HUP9901244A2 (hu)	1999-08-30
PL186466B1 (pl)	2004-01-30
EP0868420B1 (fr)	2000-03-29
RU2170230C2 (ru)	2001-07-10
JP3510270B2 (ja)	2004-03-22
AR004364A1 (es)	1998-11-04
EE04674B1 (et)	2006-08-15
US5925768A (en)	1999-07-20
ES2148820T3 (es)	2000-10-16
EP0885889A3 (fr)	1999-01-27
MY115228A (en)	2003-04-30
SI0868420T1 (en)	2000-10-31
NZ323962A (en)	1999-05-28
FR2742148B1 (fr)	1999-10-22
PL327177A1 (en)	1998-11-23
TR199801041T2 (xx)	1998-08-21
CZ177598A3 (cs)	1998-10-14
ZA9610299B (en)	1997-06-18
MX9804565A (es)	1998-09-30
IL124801A0 (en)	1999-01-26
CA2239489C (en)	2006-05-09
NO982589D0 (no)	1998-06-05
PT868420E (pt)	2000-08-31
CA2239489A1 (en)	1997-06-19
AU1101097A (en)	1997-07-03
EP0885889A2 (fr)	1998-12-23
SK283706B6 (sk)	2003-12-02
HUP9901244A3 (en)	2000-12-28
JP2000502080A (ja)	2000-02-22
EP0868420A1 (fr)	1998-10-07
AU718763B2 (en)	2000-04-20
BR9611986A (pt)	1999-02-17
CZ294307B6 (cs)	2004-11-10
UA44913C2 (uk)	2002-03-15
DE69607484D1 (de)	2000-05-04
DE69607484T2 (de)	2000-10-26
GR3033626T3 (en)	2000-10-31
DK0868420T3 (da)	2000-08-21
KR100488610B1 (ko)	2005-09-26
NO982589L (no)	1998-08-03
EE9800171A (et)	1998-12-15
TW402594B (en)	2000-08-21
ATE191211T1 (de)	2000-04-15
NO310683B1 (no)	2001-08-13
SK75898A3 (en)	1999-01-11
CN1101813C (zh)	2003-02-19
KR19990072004A (ko)	1999-09-27
IS4765A (is)	1998-06-08
FR2742148A1 (fr)	1997-06-13

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EP1230244A2 (fr)	2002-08-14	Derives tricycliques d'acide pyrazolecarboxylique, leur preparation, les compositions pharmaceutiques en contenant
WO2000047558A1 (en)	2000-08-17	Amide compounds and medicinal use thereof
JPH09506350A (ja)	1997-06-24	炎症の治療のための置換ピラゾリルベンゼンスルホンアミド
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